https://simplecast.com Startup Wisconsin Podcast Discover the untold stories of innovation across Wisconsin's growing tech startup ecosystem. From Madison to Milwaukee and everywhere in between, we go behind the scenes with the founders, investors, and community builders shaping Wisconsin's entrepreneurial future. Each episode features in-depth conversations with entrepreneurs who are leveraging Wisconsin's unique advantages to build sustainable, impactful companies across industries like healthcare, manufacturing, and agriculture. You'll hear from ecosystem builders creating opportunities statewide, investors backing the next generation of Wisconsin companies, and community leaders connecting talent, resources, and ideas. Whether you're an aspiring entrepreneur, seasoned founder, or simply curious about Wisconsin's startup scene, this podcast showcases the real stories of innovation happening right in our backyard. 2025 Startup Wisconsin en Tue, 31 Mar 2026 10:00:00 +0000 Tue, 31 Mar 2026 10:00:13 +0000 https://www.startupwi.org/podcast Startup Wisconsin Podcast https://image.simplecastcdn.com/images/96f7ddca-ab7d-40d2-8550-e4b18e16657a/948d8c2a-eb89-4891-b28c-0bf468e08f2e/3000x3000/startup-wisconsin-podcast-cover-3k.jpg?aid=rss_feed https://www.startupwi.org/podcast episodic Discover the untold stories of innovation across Wisconsin's growing tech startup ecosystem. From Madison to Milwaukee and everywhere in between, we go behind the scenes with the founders, investors, and community builders shaping Wisconsin's entrepreneurial future. Each episode features in-depth conversations with entrepreneurs who are leveraging Wisconsin's unique advantages to build sustainable, impactful companies across industries like healthcare, manufacturing, and agriculture. You'll hear from ecosystem builders creating opportunities statewide, investors backing the next generation of Wisconsin companies, and community leaders connecting talent, resources, and ideas. Whether you're an aspiring entrepreneur, seasoned founder, or simply curious about Wisconsin's startup scene, this podcast showcases the real stories of innovation happening right in our backyard. Startup Wisconsin, Jacob Miller false https://feeds.simplecast.com/35LLbbel startups, wisconsin startups, milwaukee, madison, startup wisconsin, green bay, tech startups, software, wisconsin, tech Startup Wisconsin jacob@startupwi.org 85f052d1-8f13-4cfe-9a09-0e88a1f7460c Building Belonging in Startup Communities with Angela Damiani “Every entrepreneur in Wisconsin has a place in this community.”

In this episode, I chat with Angela Damiani, CEO and Co-founder of NEWaukee, a brand engagement agency that has been making waves with its innovative activations, events, and community-building efforts. Angela shares the story of how NEWaukee, initially a social club for entrepreneurs, evolved into a thriving agency and a leader in fostering Wisconsin’s startup culture. She discusses the creation of the Midwest Founders Community (MFC), a decentralized network connecting founders across the region, and the inspiring work of elevating the Wisconsin tech scene through collaboration and mutual support.

From building a brand experience agency to leading an influential community of founders, Angela reflects on the importance of connection, mentorship, and a culture of belonging. She also shares the challenges of balancing multiple businesses and how she's helping others navigate the ups and downs of the entrepreneurial journey.

Tune in to learn

• How the Midwest Founders Community connects founders to capital, customers, and fellow entrepreneurs
• The role of brand activations in building meaningful relationships within a community
• Insights into the challenges of Wisconsin’s startup ecosystem and why it's crucial to foster risk-taking and innovation through community support

Jump into the conversation

(00:00) Introduction
(03:50) NEWaukee’s social club origins
(04:49) Discovering revenue models
(07:22) Night market's staying power
(13:15) Proudest project expansions
(15:28) The social architecture concept
(20:21) Belonging through warm invitations
(25:17) Midwest founders community building
(26:17) Finding the right founder crowd
(28:22) Growing beyond NEWaukee’s boundaries
(29:55) Real-time founder support calls
(31:07) Funding and sponsorship challenges
(33:54) Safe spaces for founders' doubts
(42:14) Milwaukee's startup ecosystem pulse
(44:30) Risk, capital, and customer sandboxes
(47:30) Vision for a founder fund

Connect with Angela Damiani: https://www.linkedin.com/in/angeladamiani/
Check out NEWaukee: https://www.newaukee.com/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Tue, 31 Mar 2026 10:00:00 +0000 jacob@startupwi.org (Jacob Miller, Angela Damiani) https://www.startupwi.org/podcast “Every entrepreneur in Wisconsin has a place in this community.”

In this episode, I chat with Angela Damiani, CEO and Co-founder of NEWaukee, a brand engagement agency that has been making waves with its innovative activations, events, and community-building efforts. Angela shares the story of how NEWaukee, initially a social club for entrepreneurs, evolved into a thriving agency and a leader in fostering Wisconsin’s startup culture. She discusses the creation of the Midwest Founders Community (MFC), a decentralized network connecting founders across the region, and the inspiring work of elevating the Wisconsin tech scene through collaboration and mutual support.

From building a brand experience agency to leading an influential community of founders, Angela reflects on the importance of connection, mentorship, and a culture of belonging. She also shares the challenges of balancing multiple businesses and how she's helping others navigate the ups and downs of the entrepreneurial journey.

Tune in to learn

• How the Midwest Founders Community connects founders to capital, customers, and fellow entrepreneurs
• The role of brand activations in building meaningful relationships within a community
• Insights into the challenges of Wisconsin’s startup ecosystem and why it's crucial to foster risk-taking and innovation through community support

Jump into the conversation

(00:00) Introduction
(03:50) NEWaukee’s social club origins
(04:49) Discovering revenue models
(07:22) Night market's staying power
(13:15) Proudest project expansions
(15:28) The social architecture concept
(20:21) Belonging through warm invitations
(25:17) Midwest founders community building
(26:17) Finding the right founder crowd
(28:22) Growing beyond NEWaukee’s boundaries
(29:55) Real-time founder support calls
(31:07) Funding and sponsorship challenges
(33:54) Safe spaces for founders' doubts
(42:14) Milwaukee's startup ecosystem pulse
(44:30) Risk, capital, and customer sandboxes
(47:30) Vision for a founder fund

Connect with Angela Damiani: https://www.linkedin.com/in/angeladamiani/
Check out NEWaukee: https://www.newaukee.com/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Building Belonging in Startup Communities with Angela Damiani Jacob Miller, Angela Damiani 00:50:06 Angela Damiani is the CEO of NEWaukee and one of the founding members of Midwest Founders Community. We talk about why belonging requires repeated warm invitations, the loneliness that sparked MFC, and her critique that Wisconsin's investor class needs higher risk tolerance. Angela Damiani is the CEO of NEWaukee and one of the founding members of Midwest Founders Community. We talk about why belonging requires repeated warm invitations, the loneliness that sparked MFC, and her critique that Wisconsin's investor class needs higher risk tolerance. false full 17 de130d3a-704d-4a24-8d27-0aec38355917 Your Cell Phone is Already Using This Tech (You Just Don't Know It) with Russell From of WayFi Wireless “There’s no reason every small business in Wisconsin shouldn’t use this.”

In this episode, I chat with Russell From, President and Co-Founder of WayFi Wireless, a company revolutionizing connectivity for businesses and nonprofits across Wisconsin and the world. He shares the inspiring journey of how WayFi Wireless uses cutting-edge technology to fix cellular dead zones by leveraging wifi, without the hefty costs traditionally associated with infrastructure.

From working at Verizon to tech founder, Russell discusses WayFi Wireless' 10,000+ global deployments powered by PassPoint technology, bridging the digital divide by offering free connectivity to users that’s funded entirely by carriers. He also  shares their recent "Best Open Roaming Deployment" award, their work with the Coverage Across America Program in Wisconsin, and the hard-earned lessons he’s gathered while building a startup from the ground up.

Tune in to learn:

  • How cell phone carriers pay for Wi-Fi to reduce churn and enhance customer experience
  • How Passpoint/Hotspot 2.0 ensures seamless, secure connections without popups or apps
  • What it takes to go from MVP to scale through partner strategy, support, and distribution

Jump into the conversation:

(00:00) Intro

(00:36) Meet Russ of WayFi Wireless

(02:03) From Verizon engineer to founder

(06:38) Why Passpoint and open roaming took off

(12:40) Pivoting to Wi-Fi and scaling to 1,200 locations

(22:22) The business of Wi-Fi monetization

(28:41) How blockchain speeds up carrier payments

(35:57) Lessons from corporate to startup life 

(42:05) The transition from funding to self-sustaining growth

(46:08) Big wins and international expansion

Connect

Connect with Russell From: https://www.linkedin.com/in/russfr/
Check out WayFi Wireless: https://wayfiwireless.com/

Follow

Follow us on LinkedIn: https://www.linkedin.com/company/startup-wisconsin/
Subscribe to the Startup Wisconsin Newsletter: https://www.startupwi.org
Check out Headway: https://www.headway.io

Connect with Jacob Miller: 
https://www.linkedin.com/in/kineticbear

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Tue, 10 Mar 2026 10:00:00 +0000 jacob@startupwi.org (Jacob Miller, Russell From) https://www.startupwi.org/podcast “There’s no reason every small business in Wisconsin shouldn’t use this.”

In this episode, I chat with Russell From, President and Co-Founder of WayFi Wireless, a company revolutionizing connectivity for businesses and nonprofits across Wisconsin and the world. He shares the inspiring journey of how WayFi Wireless uses cutting-edge technology to fix cellular dead zones by leveraging wifi, without the hefty costs traditionally associated with infrastructure.

From working at Verizon to tech founder, Russell discusses WayFi Wireless' 10,000+ global deployments powered by PassPoint technology, bridging the digital divide by offering free connectivity to users that’s funded entirely by carriers. He also  shares their recent "Best Open Roaming Deployment" award, their work with the Coverage Across America Program in Wisconsin, and the hard-earned lessons he’s gathered while building a startup from the ground up.

Tune in to learn:

  • How cell phone carriers pay for Wi-Fi to reduce churn and enhance customer experience
  • How Passpoint/Hotspot 2.0 ensures seamless, secure connections without popups or apps
  • What it takes to go from MVP to scale through partner strategy, support, and distribution

Jump into the conversation:

(00:00) Intro

(00:36) Meet Russ of WayFi Wireless

(02:03) From Verizon engineer to founder

(06:38) Why Passpoint and open roaming took off

(12:40) Pivoting to Wi-Fi and scaling to 1,200 locations

(22:22) The business of Wi-Fi monetization

(28:41) How blockchain speeds up carrier payments

(35:57) Lessons from corporate to startup life 

(42:05) The transition from funding to self-sustaining growth

(46:08) Big wins and international expansion

Connect

Connect with Russell From: https://www.linkedin.com/in/russfr/
Check out WayFi Wireless: https://wayfiwireless.com/

Follow

Follow us on LinkedIn: https://www.linkedin.com/company/startup-wisconsin/
Subscribe to the Startup Wisconsin Newsletter: https://www.startupwi.org
Check out Headway: https://www.headway.io

Connect with Jacob Miller: 
https://www.linkedin.com/in/kineticbear

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Your Cell Phone is Already Using This Tech (You Just Don't Know It) with Russell From of WayFi Wireless Jacob Miller, Russell From 00:55:14 Russell From spent years at Verizon before co-founding WayFi Wireless, a company that fixes cellular dead zones using wifi funded entirely by carriers. We talk Passpoint technology, 10,000+ global deployments, and the hard lessons of going from corporate to startup life. Russell From spent years at Verizon before co-founding WayFi Wireless, a company that fixes cellular dead zones using wifi funded entirely by carriers. We talk Passpoint technology, 10,000+ global deployments, and the hard lessons of going from corporate to startup life. corporate to founder, passpoint, startup ecosystem, wifi monetization, blockchain payments, cellular dead zones, startup funding, b2b saas, wisconsin startup, wifi connectivity, telecom startup, digital divide, wayfi wireless, madison startup, connectivity solutions, bootstrapping, wireless technology, carrier wifi, coverage across america, startup lessons, scaling a startup, open roaming, infrastructure technology, hotspot 2.0, verizon, russell from false full 16 1de298f5-016e-4c67-b6cb-bbfef4797780 Follow What Feels Alive: Building Two Mission-Driven Startups with Jillian Bichanich Podcast Sponsor

The Startup Wisconsin Podcast is presented by Valency Fund.

Episode Notes

“It shouldn’t be this hard to do good in this world.”

In this episode, I sit down with Jillian Bichanich, a Wisconsin-born founder and builder, to discuss how she is growing two mission-driven startups at the same time. Jillian shares her journey as the co-founder of Cubbi, an app designed to support families navigating disabilities, and as the founder of Pocketchange, a platform dedicated to helping consumers shop based on their values. 

Jillian explains why following what feels alive has guided her entrepreneurial path and how facing rejection and chaos shaped her drive. We explore the unique partnership she shares with her co-founder and her experience of bootstrapping both companies. Jillian also reflects on the importance of aligning business with personal values, and her vision for revolutionizing industries with purpose-driven ventures.

Tune in to learn:

  • Why building two startups at once can fuel growth and creativity
  • How following what feels alive can guide founders through chaos and uncertainty
  • Why aligning your business with your personal values creates lasting impact

Jump into the conversation:

(00:00) Introduction

(00:33) Meet Jillian Bichanich of Cubbi and Pocketchange

(01:40) Cubbi’s mission to support families

(06:42) How Cubbi transitioned to sponsor funding

(09:38) Jillian's path to founding Cubbi and Pocketchange

(12:16) Building a strong co-founder partnership

(15:42) How Jillian balances two startups

(19:24) Why ego-free collaboration is essential for success

(22:46) Building a values-driven shopping app

(25:37) From branding to MVP the hard way

(28:03) Why Madison is ideal for entrepreneurs

(37:28) Cubbi’s new "pay what you can" model

Connect with the Guest

Connect with Jillian Bichanich: https://www.linkedin.com/in/jillianphyllis/
Check out Cubbi: https://www.cubbiapp.com/
Check out Pocketchange: https://pocketchangethe.world/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Thu, 26 Feb 2026 11:00:00 +0000 jacob@startupwi.org (Jacob Miller, Jillian Bichanich) https://www.startupwi.org/podcast Podcast Sponsor

The Startup Wisconsin Podcast is presented by Valency Fund.

Episode Notes

“It shouldn’t be this hard to do good in this world.”

In this episode, I sit down with Jillian Bichanich, a Wisconsin-born founder and builder, to discuss how she is growing two mission-driven startups at the same time. Jillian shares her journey as the co-founder of Cubbi, an app designed to support families navigating disabilities, and as the founder of Pocketchange, a platform dedicated to helping consumers shop based on their values. 

Jillian explains why following what feels alive has guided her entrepreneurial path and how facing rejection and chaos shaped her drive. We explore the unique partnership she shares with her co-founder and her experience of bootstrapping both companies. Jillian also reflects on the importance of aligning business with personal values, and her vision for revolutionizing industries with purpose-driven ventures.

Tune in to learn:

  • Why building two startups at once can fuel growth and creativity
  • How following what feels alive can guide founders through chaos and uncertainty
  • Why aligning your business with your personal values creates lasting impact

Jump into the conversation:

(00:00) Introduction

(00:33) Meet Jillian Bichanich of Cubbi and Pocketchange

(01:40) Cubbi’s mission to support families

(06:42) How Cubbi transitioned to sponsor funding

(09:38) Jillian's path to founding Cubbi and Pocketchange

(12:16) Building a strong co-founder partnership

(15:42) How Jillian balances two startups

(19:24) Why ego-free collaboration is essential for success

(22:46) Building a values-driven shopping app

(25:37) From branding to MVP the hard way

(28:03) Why Madison is ideal for entrepreneurs

(37:28) Cubbi’s new "pay what you can" model

Connect with the Guest

Connect with Jillian Bichanich: https://www.linkedin.com/in/jillianphyllis/
Check out Cubbi: https://www.cubbiapp.com/
Check out Pocketchange: https://pocketchangethe.world/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Follow What Feels Alive: Building Two Mission-Driven Startups with Jillian Bichanich Jacob Miller, Jillian Bichanich 00:41:36 Jillian Bichanich shares her journey of building two mission-driven startups at the same time. Jillian gets real about following what feels alive, the power of a great co-founder relationship, and why entrepreneurship is just a mirror of who you already are. Jillian Bichanich shares her journey of building two mission-driven startups at the same time. Jillian gets real about following what feels alive, the power of a great co-founder relationship, and why entrepreneurship is just a mirror of who you already are. cubbi, following what feels alive, entrepreneurship mindset, wisconsin founders, running two startups, social impact, pocketchange, values-based business, disability support, conscious consumerism, women founders, mission-driven startups, madison startups, co-founder relationships, jillian bichanich, bootstrapping, resilience, special education technology false full 15 00d68b7b-1cdd-46c7-b3a3-7bbf59c54bdc Helping Founders Get Out of Their Own Way with Michael Ceely In this episode, I sit down with Michael Ceely, a high-performance coach for executives, entrepreneurs, and athletes, to talk about why founders get stuck in fear, anxiety spirals, and self-sabotage. He brings a rare perspective to the founder mindset because he knows when someone needs coaching and when they actually need therapy.

Michael reframes imposter syndrome as a normal response to new situations, explains why anxiety is often an action signal rather than a problem, and shares how getting the focus off yourself and onto your customer can quiet a lot of the noise. We also talk about Madison’s startup ecosystem, what he learned from StartingBlock’s Level Set program, and his ambitious goal to scale into a $10M/year business.

Tune in to learn:

  • Why imposter syndrome is a normal insecurity and what to do with it
  • Why anxiety is often an “action signal,” and the simple habit that breaks the spiral
  • How the 80% rule + real delegation help founders regain momentum

 

Jump into the conversation:

(00:00) Intro

(00:37) Meet Michael Ceely

(01:41) A Wisconsin story of becoming a coach

(05:04) How Michael balances psychotherapy and coaching work

(10:39) Why coaching’s lack of regulation matters

(18:13) Common patterns founders struggle with

(27:24) Where does anxiety come from

(29:43) The 80% rule for decision making

(31:58) How self-sabotage shows up

(33:28) Madison’s impact on founder mindset

(36:14) Inside Madison’s StartingBlock experience

(38:48) What makes Madison a good place to build

(44:10) Why accountability beats another workshop

(48:21) Scaling with intention, not shortcuts

 

Connect with Michael Ceely: https://www.linkedin.com/in/michael-ceely/

Follow Michael Ceely on Instagram: http://instagram.com/michael_ceely/

Check out Michael Ceely’s official website: https://www.michaelceely.com/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Tue, 17 Feb 2026 11:00:00 +0000 jacob@startupwi.org (Michael Ceely, Jacob Miller) https://www.startupwi.org/podcast In this episode, I sit down with Michael Ceely, a high-performance coach for executives, entrepreneurs, and athletes, to talk about why founders get stuck in fear, anxiety spirals, and self-sabotage. He brings a rare perspective to the founder mindset because he knows when someone needs coaching and when they actually need therapy.

Michael reframes imposter syndrome as a normal response to new situations, explains why anxiety is often an action signal rather than a problem, and shares how getting the focus off yourself and onto your customer can quiet a lot of the noise. We also talk about Madison’s startup ecosystem, what he learned from StartingBlock’s Level Set program, and his ambitious goal to scale into a $10M/year business.

Tune in to learn:

  • Why imposter syndrome is a normal insecurity and what to do with it
  • Why anxiety is often an “action signal,” and the simple habit that breaks the spiral
  • How the 80% rule + real delegation help founders regain momentum

 

Jump into the conversation:

(00:00) Intro

(00:37) Meet Michael Ceely

(01:41) A Wisconsin story of becoming a coach

(05:04) How Michael balances psychotherapy and coaching work

(10:39) Why coaching’s lack of regulation matters

(18:13) Common patterns founders struggle with

(27:24) Where does anxiety come from

(29:43) The 80% rule for decision making

(31:58) How self-sabotage shows up

(33:28) Madison’s impact on founder mindset

(36:14) Inside Madison’s StartingBlock experience

(38:48) What makes Madison a good place to build

(44:10) Why accountability beats another workshop

(48:21) Scaling with intention, not shortcuts

 

Connect with Michael Ceely: https://www.linkedin.com/in/michael-ceely/

Follow Michael Ceely on Instagram: http://instagram.com/michael_ceely/

Check out Michael Ceely’s official website: https://www.michaelceely.com/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Helping Founders Get Out of Their Own Way with Michael Ceely Michael Ceely, Jacob Miller 00:52:43 Michael Ceely is a high performance coach who helps founders get out of their own way. We talk about reframing imposter syndrome, using anxiety as an action signal, and why Madison founders shouldn't shrink their ambitions. Michael Ceely is a high performance coach who helps founders get out of their own way. We talk about reframing imposter syndrome, using anxiety as an action signal, and why Madison founders shouldn't shrink their ambitions. founder anxiety, startup ecosystem, wisconsin entrepreneur, business coaching, entrepreneur mental health, michael ceely, high performance coaching, founder insecurity, startup therapy, startup mindset, madison startup, founder coaching, entrepreneur mindset, self-sabotage, executive coaching, imposter syndrome false full 14 f9cacb53-f77e-4582-8534-606d649659d1 How This Website is Helping Solve the Mental Health Crisis with Ben Camp of Recovery.com "Everyone's recovering from something."

Millions struggle to find the treatment they need, often unsure where to begin.

That’s where Ben Camp, CEO and co-founder of Recovery.com, comes in.

Ben is leading a revolution in how people access addiction and mental health care, making it easier and more trustworthy than ever before.

In this episode, Ben discusses how Recovery.com built a patient-first platform in an industry where trust is paramount, scaled it using unconventional strategies, and successfully navigated a major brand pivot. From his marketing background to testing their model in India and raising Series B funding, Ben’s journey is one of overcoming significant challenges with a bold, patient-centered approach.

Tune in to hear how Recovery.com is reshaping the mental health recovery landscape and what’s next in the fight for better care.

Tune in to learn:

  • How testing the company’s platform in India before the U.S. helped fine-tune their freemium model
  • What it looks like to balance mission and business incentives without compromising patient trust
  • Why buying the Recovery.com domain became a turning point

Jump into the conversation:

(00:00) Intro

(00:38) Meet Ben Camp of Recovery.com

(01:50) How Recovery.com got started

(06:09) A freemium model that converts

(08:33) Fundraising lessons from their first investor

(11:48) How to scale with purpose

(15:37) Why Recovery.com was a game changer

(21:16) The early days of hiring and growing the team

(25:56) When to step back and let the team lead

(29:24) The strategy behind acquisitions and funding choices

(37:03) What growth looks like in the year ahead 

Connect with Ben Camp: https://www.linkedin.com/in/benjamincamp/

Check out Recovery.com: https://www.recovery.com

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Tue, 10 Feb 2026 12:00:00 +0000 jacob@startupwi.org (Ben Camp, Jacob Miller) https://www.startupwi.org/podcast "Everyone's recovering from something."

Millions struggle to find the treatment they need, often unsure where to begin.

That’s where Ben Camp, CEO and co-founder of Recovery.com, comes in.

Ben is leading a revolution in how people access addiction and mental health care, making it easier and more trustworthy than ever before.

In this episode, Ben discusses how Recovery.com built a patient-first platform in an industry where trust is paramount, scaled it using unconventional strategies, and successfully navigated a major brand pivot. From his marketing background to testing their model in India and raising Series B funding, Ben’s journey is one of overcoming significant challenges with a bold, patient-centered approach.

Tune in to hear how Recovery.com is reshaping the mental health recovery landscape and what’s next in the fight for better care.

Tune in to learn:

  • How testing the company’s platform in India before the U.S. helped fine-tune their freemium model
  • What it looks like to balance mission and business incentives without compromising patient trust
  • Why buying the Recovery.com domain became a turning point

Jump into the conversation:

(00:00) Intro

(00:38) Meet Ben Camp of Recovery.com

(01:50) How Recovery.com got started

(06:09) A freemium model that converts

(08:33) Fundraising lessons from their first investor

(11:48) How to scale with purpose

(15:37) Why Recovery.com was a game changer

(21:16) The early days of hiring and growing the team

(25:56) When to step back and let the team lead

(29:24) The strategy behind acquisitions and funding choices

(37:03) What growth looks like in the year ahead 

Connect with Ben Camp: https://www.linkedin.com/in/benjamincamp/

Check out Recovery.com: https://www.recovery.com

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> How This Website is Helping Solve the Mental Health Crisis with Ben Camp of Recovery.com Ben Camp, Jacob Miller 00:39:54 Ben saw people in crisis turning to the internet for help, and finding websites taking advantage of them. So he built something better. But he didn't start in the US. Ben saw people in crisis turning to the internet for help, and finding websites taking advantage of them. So he built something better. But he didn't start in the US. bootstrap vs vc, patient-first business, startup ecosystem, startup acquisition, founder mode, domain name strategy, co-founder relationship, revenue-based financing, wisconsin startup, freemium business model, recovery.com, healthx ventures, redfox ai, madison startup, series a funding, healthcare technology, ben camp, series b funding, mental health treatment, startingblock madison, startup funding alternatives, healthcare startup, startup rebrand, addiction recovery false full 13 e0eae296-d303-42cf-bd1e-685ba564cbee Turning UW Milwaukee Research Into Startups with Jessica Silvaggi of UWM Research Foundation University research is generating breakthrough ideas, but who's turning them into companies? Jessica Silvaggi of the UW Milwaukee Research Foundation explains why inventors become entrepreneurs by default and what Wisconsin's ecosystem is missing.

Key Topics

→ How the UW Milwaukee Research Foundation commercializes university research
→ The Catalyst Grant: $6.27M deployed, $49M in follow-on funding ($7.80 per dollar)
→ Why inventors typically become founders when no one else steps up
→ Wisconsin's conservative investor culture and the wait-for-traction problem
→ Building stronger founding teams and the case for fractional executives
→ Panther Partnering: the "easy button" for industry research partnerships
→ Featured startups

Segments

00:00 Intro
01:45 What the UW Milwaukee Research Foundation does
04:30 Types of inventions coming from the university (54% engineering)
07:15 Reaching students and faculty who don't realize they have inventions
09:45 The Catalyst Grant: 18 years of seed funding results
13:20 Bridge Grant and Panther Partnering programs
17:00 Express licensing for university startups
18:45 The upcoming Panther Leap philanthropic venture fund
21:30 Jessica's journey from Harvard PhD to tech transfer
26:00 Why inventors become entrepreneurs by default
29:15 Connecting external entrepreneurs with university tech
32:40 Working with corporate innovation teams
35:20 What would make the biggest impact with unlimited resources
39:00 Startup highlights
43:30 Milwaukee's evolving startup ecosystem
46:15 Gaps that still need attention
49:00 Building stronger founding teams
52:30 The case for fractional executives
55:00 Latest research going to market
58:30 How to connect with the Research Foundation

 

Resources & Links Mentioned

UW Milwaukee Research Foundation

Lubar Entrepreneurship Center at UWM

Catalyst Grant Program

Bridge Grant Program

Panther Partnering Program

Panthers Connect Platform / Pounce Network

Wisconsin Tech Council

‍I-Corps Program

 

Connect with Jessica Silvaggi

Jessica Silvaggi on LinkedIn

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Fri, 23 Jan 2026 12:00:00 +0000 jacob@startupwi.org (Jessica Silvaggi, Jacob Miller) https://www.startupwi.org/podcast University research is generating breakthrough ideas, but who's turning them into companies? Jessica Silvaggi of the UW Milwaukee Research Foundation explains why inventors become entrepreneurs by default and what Wisconsin's ecosystem is missing.

Key Topics

→ How the UW Milwaukee Research Foundation commercializes university research
→ The Catalyst Grant: $6.27M deployed, $49M in follow-on funding ($7.80 per dollar)
→ Why inventors typically become founders when no one else steps up
→ Wisconsin's conservative investor culture and the wait-for-traction problem
→ Building stronger founding teams and the case for fractional executives
→ Panther Partnering: the "easy button" for industry research partnerships
→ Featured startups

Segments

00:00 Intro
01:45 What the UW Milwaukee Research Foundation does
04:30 Types of inventions coming from the university (54% engineering)
07:15 Reaching students and faculty who don't realize they have inventions
09:45 The Catalyst Grant: 18 years of seed funding results
13:20 Bridge Grant and Panther Partnering programs
17:00 Express licensing for university startups
18:45 The upcoming Panther Leap philanthropic venture fund
21:30 Jessica's journey from Harvard PhD to tech transfer
26:00 Why inventors become entrepreneurs by default
29:15 Connecting external entrepreneurs with university tech
32:40 Working with corporate innovation teams
35:20 What would make the biggest impact with unlimited resources
39:00 Startup highlights
43:30 Milwaukee's evolving startup ecosystem
46:15 Gaps that still need attention
49:00 Building stronger founding teams
52:30 The case for fractional executives
55:00 Latest research going to market
58:30 How to connect with the Research Foundation

 

Resources & Links Mentioned

UW Milwaukee Research Foundation

Lubar Entrepreneurship Center at UWM

Catalyst Grant Program

Bridge Grant Program

Panther Partnering Program

Panthers Connect Platform / Pounce Network

Wisconsin Tech Council

‍I-Corps Program

 

Connect with Jessica Silvaggi

Jessica Silvaggi on LinkedIn

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Turning UW Milwaukee Research Into Startups with Jessica Silvaggi of UWM Research Foundation Jessica Silvaggi, Jacob Miller 00:53:48 Jessica Silvaggi, President of the UW Milwaukee Research Foundation, shares how her team transforms university research into real-world products and startups. With 16 years in tech transfer and a background spanning molecular biology to Parkinson's research, Jessica offers candid insights about the gaps in Wisconsin's startup ecosystem and what it takes to commercialize breakthrough innovations. Jessica Silvaggi, President of the UW Milwaukee Research Foundation, shares how her team transforms university research into real-world products and startups. With 16 years in tech transfer and a background spanning molecular biology to Parkinson's research, Jessica offers candid insights about the gaps in Wisconsin's startup ecosystem and what it takes to commercialize breakthrough innovations. tech transfer, lubar entrepreneurship center, panther partnering, startup funding, jessica silvaggi, seed funding, fractional executives, university entrepreneurship, university licensing, early-stage investing, angel investing wisconsin, startup wisconsin, inventor entrepreneur, research commercialization, faculty founders, uw milwaukee research foundation, wisconsin venture capital, milwaukee startups, commercializing research, bridge grant, university startups, startup teams, uwmrf, milwaukee innovation, wisconsin tech ecosystem, wisconsin tech council, catalyst grant, wisconsin startups false full 12 c82d1e40-b2a7-4f8f-8c49-695c149c8913 Funding Alternatives and Growth Capital for Wisconsin Startups with Laura Strong of Valency Fund Not every good business needs venture capital. Laura Strong of Valency Fund breaks down funding alternatives for Wisconsin startups in tech, manufacturing, and agribusiness.

Key Topics

→ Alternative financing: revenue-based financing, redeemable equity, structured exits
→ Why not every good business fits the venture capital model
→ The math behind VC fund expectations (10x returns in 3-5 years)
→ Wisconsin's extended exit timelines and what it means for founders
→ How to match your capital type to your business model
→ Madison startup ecosystem dynamics

Segments

00:00 Intro
02:12 Laura's journey from chemistry PhD to fund manager
04:45 Moving from biotech to health tech career
06:16 Why scientists rarely get into entrepreneurship
07:43 Why her investors would back her again after failure
09:21 The moment she realized Wisconsin needed different funding
11:03 2017 research on Wisconsin exits
12:17 How venture fund math actually works
13:49 Valency Fund's multiple financing models explained
15:42 Advice for founders without revenue yet
18:31 Best fit companies for Valency
19:55 Most misunderstood aspect of raising funding
20:23 "Success is sale of the company. Hard stop."
22:03 Do exited founders become angel investors?
23:49 Ad break
24:50 Challenges Wisconsin founders face raising capital
27:52 The "not enough ideas vs not enough capital" debate
31:06 Wisconsin's lead investor problem
33:38 What founders should consider before taking capital
35:09 Wisconsin's 15-year investment lifecycle
35:59 What else could change the funding landscape
37:22 Madison's startup ecosystem strengths
39:11 Individuals as the real ecosystem catalysts
40:39 Opportunities in manufacturing and agribusiness
43:39 Teaching at UW Madison's biotechnology program
44:36 Entrepreneurship lessons: "Nobody will pay you to solve that"
47:42 Future of innovation at UW Madison
48:43 UW Madison's new entrepreneurship initiative
50:18 What's next for Valency Fund
51:27 How to connect with Valency

Resources & Links Mentioned

Valency Fund

UW Madison Master's in Biotechnology Program

Forward Festival

Connect with Laura Strong

Laura Strong on LinkedIn

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Fri, 12 Dec 2025 12:00:00 +0000 jacob@startupwi.org (Laura Strong, Jacob Miller) https://www.startupwi.org/podcast Not every good business needs venture capital. Laura Strong of Valency Fund breaks down funding alternatives for Wisconsin startups in tech, manufacturing, and agribusiness.

Key Topics

→ Alternative financing: revenue-based financing, redeemable equity, structured exits
→ Why not every good business fits the venture capital model
→ The math behind VC fund expectations (10x returns in 3-5 years)
→ Wisconsin's extended exit timelines and what it means for founders
→ How to match your capital type to your business model
→ Madison startup ecosystem dynamics

Segments

00:00 Intro
02:12 Laura's journey from chemistry PhD to fund manager
04:45 Moving from biotech to health tech career
06:16 Why scientists rarely get into entrepreneurship
07:43 Why her investors would back her again after failure
09:21 The moment she realized Wisconsin needed different funding
11:03 2017 research on Wisconsin exits
12:17 How venture fund math actually works
13:49 Valency Fund's multiple financing models explained
15:42 Advice for founders without revenue yet
18:31 Best fit companies for Valency
19:55 Most misunderstood aspect of raising funding
20:23 "Success is sale of the company. Hard stop."
22:03 Do exited founders become angel investors?
23:49 Ad break
24:50 Challenges Wisconsin founders face raising capital
27:52 The "not enough ideas vs not enough capital" debate
31:06 Wisconsin's lead investor problem
33:38 What founders should consider before taking capital
35:09 Wisconsin's 15-year investment lifecycle
35:59 What else could change the funding landscape
37:22 Madison's startup ecosystem strengths
39:11 Individuals as the real ecosystem catalysts
40:39 Opportunities in manufacturing and agribusiness
43:39 Teaching at UW Madison's biotechnology program
44:36 Entrepreneurship lessons: "Nobody will pay you to solve that"
47:42 Future of innovation at UW Madison
48:43 UW Madison's new entrepreneurship initiative
50:18 What's next for Valency Fund
51:27 How to connect with Valency

Resources & Links Mentioned

Valency Fund

UW Madison Master's in Biotechnology Program

Forward Festival

Connect with Laura Strong

Laura Strong on LinkedIn

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Funding Alternatives and Growth Capital for Wisconsin Startups with Laura Strong of Valency Fund Laura Strong, Jacob Miller 00:53:58 Laura Strong, founder and CEO of Valency Fund, discusses Wisconsin's capital gap and her mission to create flexible financing alternatives for growth-stage companies that don't fit the traditional venture model. Drawing from her extensive experience in biotech, health tech, and teaching entrepreneurship at UW Madison, Laura shares insights on why Wisconsin companies take longer to exit, what founders misunderstand about equity investment, and how the ecosystem is evolving. Laura Strong, founder and CEO of Valency Fund, discusses Wisconsin's capital gap and her mission to create flexible financing alternatives for growth-stage companies that don't fit the traditional venture model. Drawing from her extensive experience in biotech, health tech, and teaching entrepreneurship at UW Madison, Laura shares insights on why Wisconsin companies take longer to exit, what founders misunderstand about equity investment, and how the ecosystem is evolving. venture capital alternatives, structured exits, valency fund, bootstrap vs vc, startup ecosystem, revenue based financing, midwest entrepreneurship, should i take venture capital, startup wisconsin podcast, alternative startup funding options, startup funding, revenue based financing for startups, how to raise funding wisconsin, startup advice, startup podcast, startup funding without equity, wisconsin innovation, uw madison entrepreneurship, why startups fail to raise capital, alternative financing, midwest tech, madison startups, founder advice on raising money, midwest tech startup scene, early stage investing, growth stage startup financing, manufacturing startups, wisconsin business, founder stories, founder funding, biotech wisconsin, agribusiness investing, milwaukee startups, redeemable equity, madison wisconsin startups, wisconsin startup ecosystem, small business funding, angel investing, growth stage funding, laura strong, bootstrap vs venture capital, wisconsin startups, venture capital alternatives for founders false full 11 c3aa8ca0-20c0-4e1e-a035-e53f5863fa83 Building Autonomous AI for Legal Contract Review with Shantanu Singh of Obviate.ai Shantanu Singh didn't follow a straight path to becoming a founder. Cell biology researcher → prosecutor → AI startup co-founder. But every "dot" he dropped along the way prepared him for this moment. When ChatGPT launched, it felt like discovering fire.

In this episode of the Startup Wisconsin Podcast, Shantanu breaks down what makes Obviate.ai different from typical AI wrappers, why most AI products are automated rather than truly autonomous, and how Milwaukee's small but mighty AI founder community creates disproportionate impact.

Episode Topics

  • The founding story of Obviate.ai
  • How autonomous AI agents differ from traditional Gen AI
  • Patent-pending legal reasoning technology
  • The "Guided Autonomy™" approach to contract management
  • Challenges of building AI for the legal industry
  • Enterprise security and data privacy in legal tech
  • The future of AI in contract negotiation
  • Lessons for founders building specialized AI tools

Segments

00:00 Introduction
01:33 Meet Shantanu Singh & Obviate AI
02:45 From Cell Biology to Law to AI Founder
05:24 "Discovering Fire" - The ChatGPT Moment
08:03 The "Dropping Dots" Philosophy
12:34 How Obviate Works - Beyond AI Wrappers
18:41 Automated vs. Autonomous AI Explained
24:38 Building Trust & Going to Market
29:35 Co-Founder Dynamics & "Move Fast and Break Things"
36:35 Wisconsin's Ecosystem Growing Pains
46:04 Margin of Safety vs. Margin of Error
49:58 Milwaukee's AI Founder Community
55:20 The 3-Day Prototype Challenge
01:03:06 What's Next for Obviate AI

Connect with Shantanu

Shantanu on LinkedIn

About Obviate.ai

  • Obviate.ai Website
  • Contract negotiation platform powered by autonomous AI agents
  • Provides detailed contract review, risk analysis, and precise redlining

Inspiration Mentioned

  • Voyager Paper - Minecraft + Nvidia research on autonomous AI agents

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Wed, 19 Nov 2025 12:00:00 +0000 jacob@startupwi.org (Shantanu Singh, Jacob Miller) https://www.startupwi.org/podcast Shantanu Singh didn't follow a straight path to becoming a founder. Cell biology researcher → prosecutor → AI startup co-founder. But every "dot" he dropped along the way prepared him for this moment. When ChatGPT launched, it felt like discovering fire.

In this episode of the Startup Wisconsin Podcast, Shantanu breaks down what makes Obviate.ai different from typical AI wrappers, why most AI products are automated rather than truly autonomous, and how Milwaukee's small but mighty AI founder community creates disproportionate impact.

Episode Topics

  • The founding story of Obviate.ai
  • How autonomous AI agents differ from traditional Gen AI
  • Patent-pending legal reasoning technology
  • The "Guided Autonomy™" approach to contract management
  • Challenges of building AI for the legal industry
  • Enterprise security and data privacy in legal tech
  • The future of AI in contract negotiation
  • Lessons for founders building specialized AI tools

Segments

00:00 Introduction
01:33 Meet Shantanu Singh & Obviate AI
02:45 From Cell Biology to Law to AI Founder
05:24 "Discovering Fire" - The ChatGPT Moment
08:03 The "Dropping Dots" Philosophy
12:34 How Obviate Works - Beyond AI Wrappers
18:41 Automated vs. Autonomous AI Explained
24:38 Building Trust & Going to Market
29:35 Co-Founder Dynamics & "Move Fast and Break Things"
36:35 Wisconsin's Ecosystem Growing Pains
46:04 Margin of Safety vs. Margin of Error
49:58 Milwaukee's AI Founder Community
55:20 The 3-Day Prototype Challenge
01:03:06 What's Next for Obviate AI

Connect with Shantanu

Shantanu on LinkedIn

About Obviate.ai

  • Obviate.ai Website
  • Contract negotiation platform powered by autonomous AI agents
  • Provides detailed contract review, risk analysis, and precise redlining

Inspiration Mentioned

  • Voyager Paper - Minecraft + Nvidia research on autonomous AI agents

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Building Autonomous AI for Legal Contract Review with Shantanu Singh of Obviate.ai Shantanu Singh, Jacob Miller 01:04:57 Shantanu Singh, Co-Founder of Obviate.ai in Milwaukee, shares how their autonomous AI platform is transforming legal contract review, saving teams time and costs. Shantanu Singh, Co-Founder of Obviate.ai in Milwaukee, shares how their autonomous AI platform is transforming legal contract review, saving teams time and costs. startup founder interview, legal operations, ai implementation, legal efficiency, startup ecosystem, lawyer entrepreneur, enterprise ai, contract automation, legal startups, autonomous ai, ai legal tech, small business legal, legal tech startups, legal innovation, legal ai tools, contract redlining, wisconsin innovation, b2b saas, ai wrappers, in-house counsel, legal ai, wisconsin tech, ai security, attorney ai, ai applications, solo practitioners, prompt engineering, ai transformation, contract management, legal compliance, ai vs automation, obviate.ai, autonomous agents, legal technology, contract intelligence, legal software, milwaukee startups, milwaukee tech, contract negotiation, legal practice automation, law tech, ai founder, generative ai, tech podcast wisconsin, legal industry disruption, ai for lawyers, contract review, chatgpt legal, law firm technology, ai agents, legal data privacy, wisconsin startups, tech entrepreneurship, shantanu singh false full 10 5673b1c4-2f97-4f87-9d63-91f222e95f9c Solving the Healthcare Housing Problem - Christina Henderson, Founder, Reliable Residence Key Topics Covered

→ The housing crisis facing healthcare travelers and medical students

→ Midterm rental market opportunities and challenges

→ Balancing medical residency with startup entrepreneurship

→ Building partnerships with Madison real estate companies

→ Creating startup communities within healthcare systems

→ Property vetting and quality control processes

→ The unique advantages healthcare professionals have as entrepreneurs

Segments

00:00 - Introduction and launch day excitement

02:20 - Why Christina never expected to be a founder

03:17 - Residency housing story

05:11 - Why hospitals don't solve housing for travelers

07:37 - How Reliable Residence works vs Airbnb/Zillow

11:49 - Balancing medical residency with startup building

12:53 - Sponsor break (Headway.io)

14:24 - Walking into Terrence Wall's office unannounced

16:22 - Madison startup ecosystem support and mentors

18:34 - Building healthcare entrepreneurship community

21:12 - What's next for Reliable Residence

22:18 - Advice for healthcare professionals considering startups

24:33 - Finding technical co-founders and resources

Resources Mentioned

Reliable Residence

Christina Henderson on LinkedIn

Merlin Mentors

BioForward

About Christina

Christina Henderson, D.O., is an anesthesiology resident at UW Health who earned her medical degree from Rocky Vista University College of Osteopathic Medicine in Parker, Colorado. Born and raised in Broomfield, CO, she has always embraced the outdoors and brings that same energy and focus to patient care & entrepreneurship. Outside the hospital, she’s an avid biker, skier, hiker, and angler.

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Thu, 25 Sep 2025 11:30:00 +0000 jacob@startupwi.org (Christina Henderson, Jacob Miller) https://www.startupwi.org/podcast Key Topics Covered

→ The housing crisis facing healthcare travelers and medical students

→ Midterm rental market opportunities and challenges

→ Balancing medical residency with startup entrepreneurship

→ Building partnerships with Madison real estate companies

→ Creating startup communities within healthcare systems

→ Property vetting and quality control processes

→ The unique advantages healthcare professionals have as entrepreneurs

Segments

00:00 - Introduction and launch day excitement

02:20 - Why Christina never expected to be a founder

03:17 - Residency housing story

05:11 - Why hospitals don't solve housing for travelers

07:37 - How Reliable Residence works vs Airbnb/Zillow

11:49 - Balancing medical residency with startup building

12:53 - Sponsor break (Headway.io)

14:24 - Walking into Terrence Wall's office unannounced

16:22 - Madison startup ecosystem support and mentors

18:34 - Building healthcare entrepreneurship community

21:12 - What's next for Reliable Residence

22:18 - Advice for healthcare professionals considering startups

24:33 - Finding technical co-founders and resources

Resources Mentioned

Reliable Residence

Christina Henderson on LinkedIn

Merlin Mentors

BioForward

About Christina

Christina Henderson, D.O., is an anesthesiology resident at UW Health who earned her medical degree from Rocky Vista University College of Osteopathic Medicine in Parker, Colorado. Born and raised in Broomfield, CO, she has always embraced the outdoors and brings that same energy and focus to patient care & entrepreneurship. Outside the hospital, she’s an avid biker, skier, hiker, and angler.

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Solving the Healthcare Housing Problem - Christina Henderson, Founder, Reliable Residence Christina Henderson, Jacob Miller 00:27:15 Join us for an incredible conversation with Christina Henderson, a third-year anesthesia resident at UW-Madison who just launched Reliable Residence on the day we recorded this interview! Christina's journey from a nightmare housing experience during medical school to building a platform that solves housing challenges for healthcare travelers is both inspiring and instructive. Join us for an incredible conversation with Christina Henderson, a third-year anesthesia resident at UW-Madison who just launched Reliable Residence on the day we recorded this interview! Christina's journey from a nightmare housing experience during medical school to building a platform that solves housing challenges for healthcare travelers is both inspiring and instructive. uw madison, medical resident life, healthcare solutions, startup ecosystem, medical technology, midterm housing, resident physician, medical student housing, medical resident entrepreneur, startup journey, hospital staffing, traveling nurses, real estate startup, healthcare system, healthcare travelers, property management, healthcare professionals, madison entrepreneur, wisconsin startup, entrepreneurship, wisconsin tech, medical field innovation, madison startups, residency, healthcare innovation, furnished housing, physician entrepreneur, christina henderson, physician founders, anesthesia resident, short term housing, healthcare housing, terrence wall, healthcare business, healthcare industry, property rental, reliable residence, medical school, healthcare startup, medical entrepreneurship false full 9 2c4acb48-71d0-4497-84ac-0e6940774e94 Automating the Paper Trail in Manufacturing - Lonni Kieffer, Co-Founder & COO, Aramid Technologies SmartCert tackles the complex world of manufacturing documentation - every bolt that goes into an airplane needs a complete "birth certificate" proving its origins, manufacturing process, and compliance standards. For decades, this critical process has been manual and paper-based, creating bottlenecks and errors throughout supply chains from small manufacturers to Boeing and Airbus.

🔻 Key Topics Covered

→ Digitizing decades-old manufacturing documentation processes

→ Building a network of 3,000+ companies across supply chains

→ The strategic decision to relocate from Phoenix to Wisconsin

→ Change management when transforming traditional industries

→ AI integration in document processing and compliance checking

→ TitletownTech partnership and Green Bay's manufacturing ecosystem

→ Scaling from individual companies to enterprise supply chain solutions

🔻 Segments

00:00 - Introduction

00:22 - SmartCert's Mission: From Paper Chaos to Digital Efficiency

02:56 - Multi-Departmental Workflows and Implementation Challenges

07:30 - Origin Story: Living the Problem in Sales

10:00 - Building the Right Team and Finding Talent

12:52 - Phoenix to Green Bay: The Reverse Migration Story

15:54 - Work-Life Balance and Midwest Advantages

19:49 - Titletown Tech Partnership and Ecosystem Support

24:23 - Manufacturing Proximity and Customer Relationships

28:23 - AI Implementation and Industry Education

33:16 - Customer Success Stories and Paper Savings

36:45 - The Future: Enterprise Adoption and Supply Chain Transformation

38:00 - Advice for Founders Considering Smaller Tech Hubs

🔻 About Lonni Kieffer

As Co-Founder and COO of Aramid Technologies, Lonni is focused on transforming traceability, documentation, and collaboration for every company across critical supply chains. She leads operations and the customer experience, ensuring that SmartCert — the company’s flagship platform — delivers measurable value and solves real-world challenges. With expertise spanning data analytics, onboarding, support, and strategic growth, Lonni is committed to building seamless, scalable solutions that help businesses thrive in a complex and competitive landscape.

🔻 Connect with Lonni on LinkedIn

https://www.linkedin.com/in/lonni-kieffer/

🔻 About SmartCert

SmartCert is a SaaS platform that digitizes and automates supply chain documentation for manufacturing industries. The company creates networks that eliminate bottlenecks, reduce errors, and automate critical compliance processes for aerospace, electronics, and manufacturing companies.

https://smartcert.tech/

🔻 Resources Mentioned

Titletown Tech
https://titletowntech.com/

Microsoft Co-Innovation Lab
https://news.microsoft.com/2023/11/15/microsoft-announces-new-co-innovation-lab-in-milwaukee/

Wisconsin Economic Summit
https://www.wedc.org/programs-and-resources/business-development/wisconsin-economic-summit/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Fri, 19 Sep 2025 11:30:00 +0000 jacob@startupwi.org (Lonni Kieffer, Jacob Miller) https://www.startupwi.org/podcast SmartCert tackles the complex world of manufacturing documentation - every bolt that goes into an airplane needs a complete "birth certificate" proving its origins, manufacturing process, and compliance standards. For decades, this critical process has been manual and paper-based, creating bottlenecks and errors throughout supply chains from small manufacturers to Boeing and Airbus.

🔻 Key Topics Covered

→ Digitizing decades-old manufacturing documentation processes

→ Building a network of 3,000+ companies across supply chains

→ The strategic decision to relocate from Phoenix to Wisconsin

→ Change management when transforming traditional industries

→ AI integration in document processing and compliance checking

→ TitletownTech partnership and Green Bay's manufacturing ecosystem

→ Scaling from individual companies to enterprise supply chain solutions

🔻 Segments

00:00 - Introduction

00:22 - SmartCert's Mission: From Paper Chaos to Digital Efficiency

02:56 - Multi-Departmental Workflows and Implementation Challenges

07:30 - Origin Story: Living the Problem in Sales

10:00 - Building the Right Team and Finding Talent

12:52 - Phoenix to Green Bay: The Reverse Migration Story

15:54 - Work-Life Balance and Midwest Advantages

19:49 - Titletown Tech Partnership and Ecosystem Support

24:23 - Manufacturing Proximity and Customer Relationships

28:23 - AI Implementation and Industry Education

33:16 - Customer Success Stories and Paper Savings

36:45 - The Future: Enterprise Adoption and Supply Chain Transformation

38:00 - Advice for Founders Considering Smaller Tech Hubs

🔻 About Lonni Kieffer

As Co-Founder and COO of Aramid Technologies, Lonni is focused on transforming traceability, documentation, and collaboration for every company across critical supply chains. She leads operations and the customer experience, ensuring that SmartCert — the company’s flagship platform — delivers measurable value and solves real-world challenges. With expertise spanning data analytics, onboarding, support, and strategic growth, Lonni is committed to building seamless, scalable solutions that help businesses thrive in a complex and competitive landscape.

🔻 Connect with Lonni on LinkedIn

https://www.linkedin.com/in/lonni-kieffer/

🔻 About SmartCert

SmartCert is a SaaS platform that digitizes and automates supply chain documentation for manufacturing industries. The company creates networks that eliminate bottlenecks, reduce errors, and automate critical compliance processes for aerospace, electronics, and manufacturing companies.

https://smartcert.tech/

🔻 Resources Mentioned

Titletown Tech
https://titletowntech.com/

Microsoft Co-Innovation Lab
https://news.microsoft.com/2023/11/15/microsoft-announces-new-co-innovation-lab-in-milwaukee/

Wisconsin Economic Summit
https://www.wedc.org/programs-and-resources/business-development/wisconsin-economic-summit/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Automating the Paper Trail in Manufacturing - Lonni Kieffer, Co-Founder & COO, Aramid Technologies Lonni Kieffer, Jacob Miller 00:40:46 Lonni Kieffer moved her startup SmartCert from Phoenix to Green Bay and has been able to tap into Wisconsin's manufacturing ecosystem and build deeper relationships with customers. As Co-Founder and COO, she's leading the digitization of supply chain documentation for over 3,000 registered companies across aerospace, electronics, and manufacturing industries. Lonni Kieffer moved her startup SmartCert from Phoenix to Green Bay and has been able to tap into Wisconsin's manufacturing ecosystem and build deeper relationships with customers. As Co-Founder and COO, she's leading the digitization of supply chain documentation for over 3,000 registered companies across aerospace, electronics, and manufacturing industries. supply chain management, manufacturing documentation, manufacturing software, titletown tech, startup ecosystem, paper to digital, midwest entrepreneur, green bay startup, supply chain digitization, digital transformation, supply chain technology, change management, entrepreneur podcast, saas startup, startup advice, wisconsin podcast, phoenix to wisconsin, startup podcast, b2b saas, wisconsin startup, traditional industry innovation, aerospace manufacturing, document automation, entrepreneur interview, green bay wisconsin, business automation, manufacturing innovation, business podcast, smartcert, founder interview, founder story, lonni kieffer, wisconsin tech ecosystem, startup founder, tech startup interview, manufacturing tech startup, industrial digitization, manufacturing automation, startup relocation false full 8 1d99561b-6750-4e80-8e11-bcb5801020df Healthcare AI Exit: RedFox AI Success Story with Nick Myers, Director of AI Innovation at Recovery.com Nick Myers recently sold his Madison-based AI startup RedFox AI to recovery.com, where he now serves as Director of AI Innovation. In this episode, Nick shares the complete journey from founding his healthcare AI company to successfully exiting after five years.

RedFox AI tackled one of the most critical challenges in artificial intelligence: preventing hallucinations when AI systems guide patients through medical processes. Nick's personal experience as a childhood leukemia survivor drove his mission to make healthcare more accessible through conversational AI that could walk people through home lab tests and medical devices.

Key Topics Covered

→ Building AI systems that don't hallucinate in healthcare settings
→ The technical architecture of constrained RAG systems
→ Navigating accessibility challenges for elderly and first-time tech users
→ How proximity and relationships drive startup success in Wisconsin
→ The acquisition process and knowing when to "get out of your own way"
→ AI's potential impact on the labor market and policy implications
→ Resources for Wisconsin startup founders and mentorship programs

Segments

00:00 - Introduction
00:27 - The RedFox AI Story: Making Healthcare Accessible
02:25 - Technical Deep Dive: Preventing AI Hallucinations
06:08 - Building for Accessibility: Elderly Users and Language Barriers
09:02 - The Exit Strategy: Building to Be Acquired
12:28 - How Proximity Led to Acquisition at StartingBlock
19:12 - Wisconsin Startup Ecosystem and Networking Advice
28:28 - Mentorship Resources and Programs in Wisconsin
32:26 - Life After Exit: Director of AI Innovation Role
39:14 - The Future of Work: AI's Impact on Jobs

About Nick Myers:

Nick Myers is the Director of AI Innovation at recovery.com and former cofounder/CEO of RedFox AI. He's been working in conversational AI since 2016 and has spoken globally about AI technology and policy. Nick is also an advocate for AI regulation and has worked with lawmakers on Wisconsin startup funding initiatives.

Connect with Nick on LinkedIn

https://www.linkedin.com/in/nick-myers-0794/

About Recovery.com:

Recovery.com (formerly Rehab Path) is a behavioral health platform that connects patients with treatment resources. The company helps hundreds of thousands of people find addiction and mental health treatment options.
https://recovery.com/

Resources Mentioned

StartingBlock Madison: https://www.startingblockmadison.org/
Merlin Mentors Program: https://merlinmentors.org/
Wisconsin Technology Council: https://wisconsintechnologycouncil.com/
UW Small Business Development Clinic: https://business.wisconsin.edu/initiatives/small-business-clinics/
Law and Entrepreneurship Clinic: https://law.wisc.edu/uwle/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Wed, 10 Sep 2025 16:00:00 +0000 jacob@startupwi.org (Nick Myers, Jacob Miller) https://www.startupwi.org/podcast Nick Myers recently sold his Madison-based AI startup RedFox AI to recovery.com, where he now serves as Director of AI Innovation. In this episode, Nick shares the complete journey from founding his healthcare AI company to successfully exiting after five years.

RedFox AI tackled one of the most critical challenges in artificial intelligence: preventing hallucinations when AI systems guide patients through medical processes. Nick's personal experience as a childhood leukemia survivor drove his mission to make healthcare more accessible through conversational AI that could walk people through home lab tests and medical devices.

Key Topics Covered

→ Building AI systems that don't hallucinate in healthcare settings
→ The technical architecture of constrained RAG systems
→ Navigating accessibility challenges for elderly and first-time tech users
→ How proximity and relationships drive startup success in Wisconsin
→ The acquisition process and knowing when to "get out of your own way"
→ AI's potential impact on the labor market and policy implications
→ Resources for Wisconsin startup founders and mentorship programs

Segments

00:00 - Introduction
00:27 - The RedFox AI Story: Making Healthcare Accessible
02:25 - Technical Deep Dive: Preventing AI Hallucinations
06:08 - Building for Accessibility: Elderly Users and Language Barriers
09:02 - The Exit Strategy: Building to Be Acquired
12:28 - How Proximity Led to Acquisition at StartingBlock
19:12 - Wisconsin Startup Ecosystem and Networking Advice
28:28 - Mentorship Resources and Programs in Wisconsin
32:26 - Life After Exit: Director of AI Innovation Role
39:14 - The Future of Work: AI's Impact on Jobs

About Nick Myers:

Nick Myers is the Director of AI Innovation at recovery.com and former cofounder/CEO of RedFox AI. He's been working in conversational AI since 2016 and has spoken globally about AI technology and policy. Nick is also an advocate for AI regulation and has worked with lawmakers on Wisconsin startup funding initiatives.

Connect with Nick on LinkedIn

https://www.linkedin.com/in/nick-myers-0794/

About Recovery.com:

Recovery.com (formerly Rehab Path) is a behavioral health platform that connects patients with treatment resources. The company helps hundreds of thousands of people find addiction and mental health treatment options.
https://recovery.com/

Resources Mentioned

StartingBlock Madison: https://www.startingblockmadison.org/
Merlin Mentors Program: https://merlinmentors.org/
Wisconsin Technology Council: https://wisconsintechnologycouncil.com/
UW Small Business Development Clinic: https://business.wisconsin.edu/initiatives/small-business-clinics/
Law and Entrepreneurship Clinic: https://law.wisc.edu/uwle/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Healthcare AI Exit: RedFox AI Success Story with Nick Myers, Director of AI Innovation at Recovery.com Nick Myers, Jacob Miller 00:58:30 Nick Myers discusses selling RedFox AI to recovery.com, building constrained AI for healthcare, and the future of work. Nick Myers discusses selling RedFox AI to recovery.com, building constrained AI for healthcare, and the future of work. healthcare ai, startup ecosystem, startup networking, workforce automation, artificial intelligence, wisconsin startup ecosystem guide, wisconsin entrepreneur, ai workforce impact discussion, startup acquisition, madison tech community, entrepreneurship networking wisconsin, ai policy, wisconsin innovation, madison entrepreneur, wisconsin startup, startup acquisition process, ai healthcare, healthcare ai startup exit story, wisconsin tech, entrepreneur interview, startup mentorship, healthcare technology innovation, redfox ai, business acquisition, ai hallucination prevention, madison startup, wisconsin business, constrained ai, healthcare technology, startup exit, startup founder, midwest startup, tech entrepreneurship, wisconsin tech scene false full 7 f7340301-b918-4137-9591-21af8f44d507 The Wisconsin Lab Using Evolution to Fight Obesity and Disease with Ben Sajdak of Fauna Bio In this episode, we explore:

→ How evolution guides modern drug discovery
→ Why ground squirrels are going to space with NASA
→ The surprising advantages of doing biotech in Wisconsin
→ Building academic-industry partnerships outside major hubs
→ Creating scientific community in the Fox Valley

What is Fauna Bio?

Fauna Bio leverages millions of years of evolution by studying animals that naturally avoid diseases humans struggle with—from cancer-resistant elephants to hibernating ground squirrels that survive without eating for six months.

Connect with Ben

LinkedIn
https://www.linkedin.com/in/ben-sajdak/
Fauna Bio
https://www.faunabio.com/
Fox Valley Science Society
https://www.tardigradesbookshelf.com/fv-science-society

Segments

00:00 - Intro
00:40 - What Fauna Bio Does: Using Evolution to Fight Disease
02:03 - Ben's Journey from Construction Worker to Biotech
03:08 - Why Study Disease-Resistant Animals vs Disease Models
04:16 - The Ground Squirrel Colony at UW-Oshkosh
05:35 - Hibernation Biology: From 300 to 3 Heartbeats Per Minute
07:02 - Academic-Industry Partnership Model
08:23 - NASA Space Mission: Sending Squirrels to Space
10:07 - Machine Learning and the "Convergence" Platform
13:04 - Sponsor Break (Headway)
14:10 - Spiny Mouse Research: Regeneration and Scar Prevention
16:44 - Wisconsin's Underrated Biotech Potential
18:11 - Breaking Down University Research Silos
19:57 - Community Building and Networking Challenges
23:14 - Showcasing Hidden University Research

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Tue, 2 Sep 2025 11:30:00 +0000 jacob@startupwi.org (Ben Sajdak, Jacob Miller) https://www.startupwi.org/podcast In this episode, we explore:

→ How evolution guides modern drug discovery
→ Why ground squirrels are going to space with NASA
→ The surprising advantages of doing biotech in Wisconsin
→ Building academic-industry partnerships outside major hubs
→ Creating scientific community in the Fox Valley

What is Fauna Bio?

Fauna Bio leverages millions of years of evolution by studying animals that naturally avoid diseases humans struggle with—from cancer-resistant elephants to hibernating ground squirrels that survive without eating for six months.

Connect with Ben

LinkedIn
https://www.linkedin.com/in/ben-sajdak/
Fauna Bio
https://www.faunabio.com/
Fox Valley Science Society
https://www.tardigradesbookshelf.com/fv-science-society

Segments

00:00 - Intro
00:40 - What Fauna Bio Does: Using Evolution to Fight Disease
02:03 - Ben's Journey from Construction Worker to Biotech
03:08 - Why Study Disease-Resistant Animals vs Disease Models
04:16 - The Ground Squirrel Colony at UW-Oshkosh
05:35 - Hibernation Biology: From 300 to 3 Heartbeats Per Minute
07:02 - Academic-Industry Partnership Model
08:23 - NASA Space Mission: Sending Squirrels to Space
10:07 - Machine Learning and the "Convergence" Platform
13:04 - Sponsor Break (Headway)
14:10 - Spiny Mouse Research: Regeneration and Scar Prevention
16:44 - Wisconsin's Underrated Biotech Potential
18:11 - Breaking Down University Research Silos
19:57 - Community Building and Networking Challenges
23:14 - Showcasing Hidden University Research

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> The Wisconsin Lab Using Evolution to Fight Obesity and Disease with Ben Sajdak of Fauna Bio Ben Sajdak, Jacob Miller 00:26:05 Ben Sajdak is leading breakthrough biotech research in Oshkosh, Wisconsin. As Director at Fauna Bio, he studies hibernating ground squirrels that could revolutionize treatments for obesity, heart disease, and even help astronauts survive space missions. Ben Sajdak is leading breakthrough biotech research in Oshkosh, Wisconsin. As Director at Fauna Bio, he studies hibernating ground squirrels that could revolutionize treatments for obesity, heart disease, and even help astronauts survive space missions. wisconsin entrepreneurs, fauna bio, startup ecosystem, scientific research, hibernation biology, startup wisconsin podcast, startup funding, biomedical science, heart disease, pharmaceutical development, obesity research, midwest biotech, wisconsin innovation, regional innovation, spiny mouse research, wisconsin startup, research partnerships, fox valley science, ground squirrels, life sciences, ben sajdak, healthcare innovation, regeneration medicine, biotech investment, animal research, medical breakthrough, biotechnology, biotech startup, bone density research, mammal studies, drug discovery, biotech community, evolution medicine, uw oshkosh, hibernation research, therapeutic development, wisconsin tech scene false full 6 801570a3-0255-408a-98d3-43d6fb96f01d From Hacker to Cybersecurity CEO: Building Continuous Security Testing with Casey Cammilleri of Sprocket Security We chat with Casey Cammilleri, CEO and founder of Sprocket Security, a Madison-based cybersecurity company that's revolutionizing how businesses approach penetration testing. Casey started as a solo penetration tester - essentially getting paid to legally hack into companies to find vulnerabilities - but realized he could help more organizations by building software to scale that expertise.

What makes Sprocket Security different is their continuous approach. Instead of testing once a year like traditional security firms, they monitor organizations continuously, testing whenever there are changes or new threats emerge, so companies always know what their risks are.

We explore Casey's journey from individual consultant to leading a team of cybersecurity experts, his approach to building company culture with both local and remote employees, and his thoughts on growing a tech business in Madison versus coastal markets. You'll also hear his practical advice for founders about when to focus on building versus pitching, and insights for anyone interested in getting started in cybersecurity.

Segments

00:00 - Intro
01:32 - What Sprocket Security Does: Continuous Penetration Testing
02:57 - Casey's Background as a Penetration Tester
04:44 - Building Software to Scale Security Testing
06:03 - Early Go-to-Market Strategy and Local Network
07:14 - Early Challenges of Scaling from Solo to Team
08:26 - Learning Leadership and Using Mentorship
11:51 - Hiring Strategy: Local vs Remote Talent
13:42 - Building Company Culture Across Distributed Teams
15:04 - Sponsor Break (Headway)
16:46 - How the Vision Has Evolved Over 8 Years
20:04 - Running MadSec: Madison Security Community
21:06 - Getting Started in Cybersecurity Career Path
23:04 - Advice for Breaking Into Cybersecurity
24:36 - Hardware Security vs Software Security Focus
25:49 - What Casey Loves About Building in Madison
26:53 - What Wisconsin's Tech Scene Needs More Of
28:23 - Pitch Contests and Capital: Casey's Perspective
32:43 - Build First, Then Sell: Casey's Bootstrap Philosophy
34:57 - Balancing Innovation with Customer Commitments

Key Topics Covered

→ Building continuous penetration testing from the ground up

→ Scaling expertise through software and automation

→ Early challenges of hiring and building company culture

→ Local vs. remote hiring strategies for specialized talent

→ Growing a tech business in Madison's startup ecosystem

→ When to bootstrap vs. seek investment funding

→ Getting started in cybersecurity and penetration testing

About Sprocket Security:

Sprocket Security is an expert-driven offensive security platform that provides continuous penetration testing. Instead of testing just once a year, they monitor organizations continuously and test whenever there are changes that impact security or new threats emerge.

Resources Mentioned:

Sprocket Security:

https://sprocketsecurity.com

Casey Cammilleri on LinkedIn: https://www.linkedin.com/in/caseycammilleri/

MadSec - Madison Information Security Group

https://www.meetup.com/madsec/

TryHackMe - Cybersecurity challenges and training

https://tryhackme.com/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Mon, 25 Aug 2025 14:12:12 +0000 jacob@startupwi.org (Casey Cammilleri, Jacob Miller) https://www.startupwi.org/podcast We chat with Casey Cammilleri, CEO and founder of Sprocket Security, a Madison-based cybersecurity company that's revolutionizing how businesses approach penetration testing. Casey started as a solo penetration tester - essentially getting paid to legally hack into companies to find vulnerabilities - but realized he could help more organizations by building software to scale that expertise.

What makes Sprocket Security different is their continuous approach. Instead of testing once a year like traditional security firms, they monitor organizations continuously, testing whenever there are changes or new threats emerge, so companies always know what their risks are.

We explore Casey's journey from individual consultant to leading a team of cybersecurity experts, his approach to building company culture with both local and remote employees, and his thoughts on growing a tech business in Madison versus coastal markets. You'll also hear his practical advice for founders about when to focus on building versus pitching, and insights for anyone interested in getting started in cybersecurity.

Segments

00:00 - Intro
01:32 - What Sprocket Security Does: Continuous Penetration Testing
02:57 - Casey's Background as a Penetration Tester
04:44 - Building Software to Scale Security Testing
06:03 - Early Go-to-Market Strategy and Local Network
07:14 - Early Challenges of Scaling from Solo to Team
08:26 - Learning Leadership and Using Mentorship
11:51 - Hiring Strategy: Local vs Remote Talent
13:42 - Building Company Culture Across Distributed Teams
15:04 - Sponsor Break (Headway)
16:46 - How the Vision Has Evolved Over 8 Years
20:04 - Running MadSec: Madison Security Community
21:06 - Getting Started in Cybersecurity Career Path
23:04 - Advice for Breaking Into Cybersecurity
24:36 - Hardware Security vs Software Security Focus
25:49 - What Casey Loves About Building in Madison
26:53 - What Wisconsin's Tech Scene Needs More Of
28:23 - Pitch Contests and Capital: Casey's Perspective
32:43 - Build First, Then Sell: Casey's Bootstrap Philosophy
34:57 - Balancing Innovation with Customer Commitments

Key Topics Covered

→ Building continuous penetration testing from the ground up

→ Scaling expertise through software and automation

→ Early challenges of hiring and building company culture

→ Local vs. remote hiring strategies for specialized talent

→ Growing a tech business in Madison's startup ecosystem

→ When to bootstrap vs. seek investment funding

→ Getting started in cybersecurity and penetration testing

About Sprocket Security:

Sprocket Security is an expert-driven offensive security platform that provides continuous penetration testing. Instead of testing just once a year, they monitor organizations continuously and test whenever there are changes that impact security or new threats emerge.

Resources Mentioned:

Sprocket Security:

https://sprocketsecurity.com

Casey Cammilleri on LinkedIn: https://www.linkedin.com/in/caseycammilleri/

MadSec - Madison Information Security Group

https://www.meetup.com/madsec/

TryHackMe - Cybersecurity challenges and training

https://tryhackme.com/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> From Hacker to Cybersecurity CEO: Building Continuous Security Testing with Casey Cammilleri of Sprocket Security Casey Cammilleri, Jacob Miller 00:37:31 From solo penetration tester to cybersecurity CEO: Casey Cammilleri shares how he built continuous security testing software and scaled expertise over 8 years with a growing team of nearly 40 employees in Madison, Wisconsin. From solo penetration tester to cybersecurity CEO: Casey Cammilleri shares how he built continuous security testing software and scaled expertise over 8 years with a growing team of nearly 40 employees in Madison, Wisconsin. continuous security testing, cybersecurity platform, cybersecurity, startup journey, cybersecurity business, startup advice, startup podcast, cybersecurity careers, startup community, security automation, madison startup scene, wisconsin tech, penetration testing, startup founders, security consultant, technical services business, tech founder, wisconsin business, bootstrapping, madison entrepreneurs, business scaling, remote hiring, penetration tester, wisconsin startups, tech entrepreneurship false full 5 1f3ce68c-97c6-419e-8991-f1db3c757a93 What's Wrong with Thought Leadership and How to Fix It Join us for an in-depth conversation with Dan Fogarty, a thought leadership strategist who helps founders and executives tell their stories authentically through content that drives real business results. Dan brings a fascinating background - he started as a journalist at major outlets like USA Today and the Boston Globe, but a boxing-related concussion led him to leave traditional media and build his own business around content strategy.

What makes Dan's approach different is how he brings journalistic rigor to thought leadership. He's not about generic LinkedIn posts or AI-generated content. Instead, he helps people find what's happening "in the room" - those insights and perspectives that only come from being deeply embedded in your industry and the conversations you have every day.

We explore what's fundamentally broken about thought leadership today, Dan's process for helping clients discover what's actually worth talking about, and his perspective as a recent transplant to Madison's startup community. You'll also hear about his new AI tool TalkBox and his thoughts on what founders should be doing more of to tell Wisconsin's innovation story.

 

Key Topics Covered

→ Why most thought leadership content fails (and how to fix it)

→ The three-circle framework for authentic content creation

→ Finding your unique insights: "what's happening in the room"

→ Personal brand vs. authentic storytelling

→ Building TalkBox: AI tool for scaling expertise

→ Moving from East Coast to Madison's startup scene

→ The future of AI in creative work and content strategy

 

🔗 Connect with Dan Fogarty

Dan Website

https://imdanfogarty.com

LinkedIn

https://www.linkedin.com/in/danfogarty1/

 

👉 Resources Mentioned

Starting Block Madison

https://www.startingblockmadison.org/

Level Set Program

https://www.startingblockmadison.org/levelset

 

Segments

00:00 - Intro and Dan's Background

01:19 - From Journalism to Content Strategy

07:48 - The COVID Turning Point

15:19 - What's Broken About Thought Leadership

20:22 - Finding What's Worth Talking About

31:34 - Sponsor Break (Headway)

33:03 - Personal Brand vs Company Brand

38:16 - Building TalkBox AI Tool

44:28 - AI and Creative Work Philosophy

48:58 - Moving to Madison Experience

57:36 - Advice for Wisconsin Founders

1:04:23 - Contact Information and Wrap-up

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Thu, 14 Aug 2025 12:00:00 +0000 jacob@startupwi.org (Dan Fogarty, Jacob Miller) https://www.startupwi.org/podcast Join us for an in-depth conversation with Dan Fogarty, a thought leadership strategist who helps founders and executives tell their stories authentically through content that drives real business results. Dan brings a fascinating background - he started as a journalist at major outlets like USA Today and the Boston Globe, but a boxing-related concussion led him to leave traditional media and build his own business around content strategy.

What makes Dan's approach different is how he brings journalistic rigor to thought leadership. He's not about generic LinkedIn posts or AI-generated content. Instead, he helps people find what's happening "in the room" - those insights and perspectives that only come from being deeply embedded in your industry and the conversations you have every day.

We explore what's fundamentally broken about thought leadership today, Dan's process for helping clients discover what's actually worth talking about, and his perspective as a recent transplant to Madison's startup community. You'll also hear about his new AI tool TalkBox and his thoughts on what founders should be doing more of to tell Wisconsin's innovation story.

 

Key Topics Covered

→ Why most thought leadership content fails (and how to fix it)

→ The three-circle framework for authentic content creation

→ Finding your unique insights: "what's happening in the room"

→ Personal brand vs. authentic storytelling

→ Building TalkBox: AI tool for scaling expertise

→ Moving from East Coast to Madison's startup scene

→ The future of AI in creative work and content strategy

 

🔗 Connect with Dan Fogarty

Dan Website

https://imdanfogarty.com

LinkedIn

https://www.linkedin.com/in/danfogarty1/

 

👉 Resources Mentioned

Starting Block Madison

https://www.startingblockmadison.org/

Level Set Program

https://www.startingblockmadison.org/levelset

 

Segments

00:00 - Intro and Dan's Background

01:19 - From Journalism to Content Strategy

07:48 - The COVID Turning Point

15:19 - What's Broken About Thought Leadership

20:22 - Finding What's Worth Talking About

31:34 - Sponsor Break (Headway)

33:03 - Personal Brand vs Company Brand

38:16 - Building TalkBox AI Tool

44:28 - AI and Creative Work Philosophy

48:58 - Moving to Madison Experience

57:36 - Advice for Wisconsin Founders

1:04:23 - Contact Information and Wrap-up

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> What's Wrong with Thought Leadership and How to Fix It Dan Fogarty, Jacob Miller 01:05:07 We explore what's fundamentally broken about thought leadership today, Dan Fogarty's process for helping clients discover what's actually worth talking about, and his perspective as a recent transplant to Madison's startup community. We explore what's fundamentally broken about thought leadership today, Dan Fogarty's process for helping clients discover what's actually worth talking about, and his perspective as a recent transplant to Madison's startup community. founder storytelling, business content, founder journey, startup advice, startup podcast, startup community, journalism, content marketing, madison startup scene, content creation, entrepreneurship, startup founders, digital marketing, content strategy, linkedin marketing, wisconsin business, b2b marketing, social media strategy, business storytelling, thought leadership, madison entrepreneurs, authentic marketing, personal branding, wisconsin startups false full 4 3004b984-53cd-4663-9b68-b22d6da9866f AI-Powered Sales Training: Syrenn Cofounders Share Their Journey - Nati Solomon Fett and Colin Guest Join us for an in-depth conversation with Nati Solomon Fett and Colin Guest, the cofounders of Syrenn, a Madison-based AI-powered sales training platform that's revolutionizing how sales teams practice high-stakes conversations.

In this episode, we explore Syrenn's unique approach to sales training - moving beyond traditional role-playing to create AI-powered scenarios that actually help sales reps improve their conversational skills. Both Nati and Colin bring strong technical backgrounds to this challenge, and their journey from multiple pivots to finding product-market fit offers valuable lessons for any entrepreneur.

We dive deep into their hands-on customer discovery process, including walking into gyms and car dealerships to understand how sales training really works. You'll hear about their experience in the Madworks Accelerator Program, their thoughts on building with AI coding tools like Cursor, and what they've learned about Madison's tight-knit startup ecosystem.

Key Topics Covered

→ Building AI-powered sales training from the ground up

→ The pivot journey: from solution seeking problem to market fit

→ Real-world customer discovery strategies

→ Co-founder dynamics with two technical founders

→ Madworks Accelerator experience and mentorship value

→ Madison startup community pros and cons

→ Leveraging AI tools for faster development

 

About Syrenn

Syrenn helps sales managers remove themselves as bottlenecks in training by providing AI-powered role-play scenarios for their sales reps.

 

Resources Mentioned

Syrenn: https://syrenn.co/

Cursor AI coding tool: https://cursor.com/en

Madworks Accelerator: https://www.startingblockmadison.org/madworks-business-accelerator

Starting Block Madison: https://www.startingblockmadison.org/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Wed, 6 Aug 2025 11:30:00 +0000 jacob@startupwi.org (Colin Guest, Nati Solomon Fett, AI sales training, B2B SaaS startup, Wisconsin entrepreneurs, Madison startups, startup cofounders, technical founders, customer discovery process, startup pivot stories, MathWorks accelerator, AI coding tools, product-market fit, startup mentorship, Madison startup ecosystem, technical cofounder relationship, sales enablement, conversational AI, StartingBlock Madison, Midwest entrepreneurs, Syrenn cofounders, Jacob Miller) https://www.startupwi.org/podcast Join us for an in-depth conversation with Nati Solomon Fett and Colin Guest, the cofounders of Syrenn, a Madison-based AI-powered sales training platform that's revolutionizing how sales teams practice high-stakes conversations.

In this episode, we explore Syrenn's unique approach to sales training - moving beyond traditional role-playing to create AI-powered scenarios that actually help sales reps improve their conversational skills. Both Nati and Colin bring strong technical backgrounds to this challenge, and their journey from multiple pivots to finding product-market fit offers valuable lessons for any entrepreneur.

We dive deep into their hands-on customer discovery process, including walking into gyms and car dealerships to understand how sales training really works. You'll hear about their experience in the Madworks Accelerator Program, their thoughts on building with AI coding tools like Cursor, and what they've learned about Madison's tight-knit startup ecosystem.

Key Topics Covered

→ Building AI-powered sales training from the ground up

→ The pivot journey: from solution seeking problem to market fit

→ Real-world customer discovery strategies

→ Co-founder dynamics with two technical founders

→ Madworks Accelerator experience and mentorship value

→ Madison startup community pros and cons

→ Leveraging AI tools for faster development

 

About Syrenn

Syrenn helps sales managers remove themselves as bottlenecks in training by providing AI-powered role-play scenarios for their sales reps.

 

Resources Mentioned

Syrenn: https://syrenn.co/

Cursor AI coding tool: https://cursor.com/en

Madworks Accelerator: https://www.startingblockmadison.org/madworks-business-accelerator

Starting Block Madison: https://www.startingblockmadison.org/

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> AI-Powered Sales Training: Syrenn Cofounders Share Their Journey - Nati Solomon Fett and Colin Guest Colin Guest, Nati Solomon Fett, AI sales training, B2B SaaS startup, Wisconsin entrepreneurs, Madison startups, startup cofounders, technical founders, customer discovery process, startup pivot stories, MathWorks accelerator, AI coding tools, product-market fit, startup mentorship, Madison startup ecosystem, technical cofounder relationship, sales enablement, conversational AI, StartingBlock Madison, Midwest entrepreneurs, Syrenn cofounders, Jacob Miller 00:39:46 As cofounders, Nati and Colin from Syrenn share how they built an AI-powered sales training platform, their pivot journey, and lessons from Madison's startup scene. As cofounders, Nati and Colin from Syrenn share how they built an AI-powered sales training platform, their pivot journey, and lessons from Madison's startup scene. false full 3 4f803ad9-21b6-4796-8369-f693f860434b Evolving the Path to Entrepreneurship at StartingBlock in Madison - Beth Ott, Director of Entrepreneurial Programming Join us for an in-depth conversation with Beth Ott, Director of Entrepreneurial Programming at StartingBlock in Madison, as we explore the evolution of entrepreneurship education and community building in Wisconsin.

In this episode

Beth shares her unique journey from educator to entrepreneur, co-founding House on Jenny Street and teaching the innovative "Clark Tank" program. We dive deep into Starting Block's comprehensive program offerings, including their groundbreaking LEAP Year initiative - a "third option" for young adults beyond the traditional college-or-work binary.

Discover how Starting Block is transforming entrepreneurship education through practical, hands-on programs like Level Set (their 6-week pre-accelerator) and Next Level (12-week accelerator), plus industry-specific accelerators with partners like American Family Insurance. Beth reveals the key "light bulb moments" founders experience and shares insights about Madison's vibrant entrepreneurial ecosystem.

We also explore the challenges and opportunities in Wisconsin's startup landscape, the importance of community collaboration, and how the Midwest can develop solutions tailored to regional problems.

 

Topics Covered

→ Beth's transition from education to entrepreneurship

→ StartingBlock's program portfolio and impact

→ LEAP Year: Creating a third option for young adults

→ Founder success stories and breakthrough moments

→ Madison's entrepreneurial ecosystem strengths

→ Building effective startup community networks

→ The future of entrepreneurship education

 

Segments

00:00 - Intro

01:24 - Beth's Education Background and Teaching Philosophy

02:37 - From Furniture Flipping to Entrepreneurship

03:56 - Clark Street Community School and Clark Tank Program

08:41 - Joining Starting Block Madison

10:46 - Starting Block's Program Overview

14:17 - Introducing LEAP Year - The Third Option

22:53 - LEAP Year Application Process and Structure

27:25 - Sponsor Break

28:59 - Founder Success Stories and Light Bulb Moments

35:06 - Madison's Entrepreneurial Community Strengths

40:26 - Startup Wisconsin's Vision and Ecosystem Challenges

45:49 - Building Midwest Startup Collaboration

49:47 - Advice for Aspiring Entrepreneurs

51:43 - Shout Outs and Contact Information

 

Resources Mentioned

StartingBlock Website

Leap Year Program

Events at StartingBlock

The Mom Test

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Wed, 6 Aug 2025 11:15:00 +0000 jacob@startupwi.org (Beth Ott, Jacob Miller) https://www.startupwi.org/podcast Join us for an in-depth conversation with Beth Ott, Director of Entrepreneurial Programming at StartingBlock in Madison, as we explore the evolution of entrepreneurship education and community building in Wisconsin.

In this episode

Beth shares her unique journey from educator to entrepreneur, co-founding House on Jenny Street and teaching the innovative "Clark Tank" program. We dive deep into Starting Block's comprehensive program offerings, including their groundbreaking LEAP Year initiative - a "third option" for young adults beyond the traditional college-or-work binary.

Discover how Starting Block is transforming entrepreneurship education through practical, hands-on programs like Level Set (their 6-week pre-accelerator) and Next Level (12-week accelerator), plus industry-specific accelerators with partners like American Family Insurance. Beth reveals the key "light bulb moments" founders experience and shares insights about Madison's vibrant entrepreneurial ecosystem.

We also explore the challenges and opportunities in Wisconsin's startup landscape, the importance of community collaboration, and how the Midwest can develop solutions tailored to regional problems.

 

Topics Covered

→ Beth's transition from education to entrepreneurship

→ StartingBlock's program portfolio and impact

→ LEAP Year: Creating a third option for young adults

→ Founder success stories and breakthrough moments

→ Madison's entrepreneurial ecosystem strengths

→ Building effective startup community networks

→ The future of entrepreneurship education

 

Segments

00:00 - Intro

01:24 - Beth's Education Background and Teaching Philosophy

02:37 - From Furniture Flipping to Entrepreneurship

03:56 - Clark Street Community School and Clark Tank Program

08:41 - Joining Starting Block Madison

10:46 - Starting Block's Program Overview

14:17 - Introducing LEAP Year - The Third Option

22:53 - LEAP Year Application Process and Structure

27:25 - Sponsor Break

28:59 - Founder Success Stories and Light Bulb Moments

35:06 - Madison's Entrepreneurial Community Strengths

40:26 - Startup Wisconsin's Vision and Ecosystem Challenges

45:49 - Building Midwest Startup Collaboration

49:47 - Advice for Aspiring Entrepreneurs

51:43 - Shout Outs and Contact Information

 

Resources Mentioned

StartingBlock Website

Leap Year Program

Events at StartingBlock

The Mom Test

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Evolving the Path to Entrepreneurship at StartingBlock in Madison - Beth Ott, Director of Entrepreneurial Programming Beth Ott, Jacob Miller 00:55:16 Beth Ott shares how StartingBlock in Madison, WI is creating new pathways to entrepreneurship through LEAP Year, a community-focused programs for young founders and more. Beth Ott shares how StartingBlock in Madison, WI is creating new pathways to entrepreneurship through LEAP Year, a community-focused programs for young founders and more. midwest innovation, third option after high school, what is the leap year program in madison, startup community building, how educators are transforming startup education., early-stage startup support wisconsin, wisconsin entrepreneurial network, madison entrepreneurship, how startingblock helps founders grow, entrepreneurial programming, entrepreneurship education wisconsin, startup programs and accelerators in wisconsin, leap year program, clark tank program, startup founder journey, american family accelerator, startup education madison, startingblock madison, wisconsin startup ecosystem, educator to entrepreneur, alternative to college for entrepreneurs, hands-on entrepreneurship programs, startup mentorship madison, advice for early-stage entrepreneurs from beth ott, how to support young entrepreneurs in the midwest, midwest startup community, youth entrepreneurship madison, alternatives to college for aspiring founders false full 2 5ee99faa-3a5f-4e15-9374-d9ab5d85779a Building Startup Connections Across Wisconsin's Growing Tech Scene Welcome to the Startup Wisconsin Podcast! Join hosts Jacob Miller and Andrew Verboncouer as they share their vision for building a thriving statewide tech startup community across Wisconsin.

In this first episode:

🏛️ How we're supporting founders from Green Bay to Milwaukee to Madison

🎯 Our approach to year-round community building beyond just Startup Week

🤝 Plans for supper clubs, mentorship programs, and meaningful networking experiences

📅 What to expect from Startup Wisconsin Week 2025 (November 10-14)

 

Featured Topics:

→ Wisconsin startup ecosystem

→ Tech entrepreneurship in the Midwest

→ Community building for founders

→ Startup networking and mentorship

→ Wisconsin venture capital and funding

→ Green Bay, Milwaukee, and Madison startup scenes

 

Upcoming Guests Include:

→ Founders from Siren (Madison sales simulation platform)

→ Beth Ott from Starting Block Madison

→ Dan Fogarty on thought leadership

→ Casey Cammilleri, Sprocket Security

→ Ben from Fauna Bio (space hibernation research!)

→ Nick Myers, Red Fox AI exit story with Recovery.com

 

Segments:

00:00 - Intro & Welcome

00:39 - Meet the Hosts

04:03 - Startup Wisconsin Mission & Vision

05:40 - Why We're Doing This Podcast

11:08 - Types of Guests & Conversations

15:29 - Sponsor Message

16:56 - Government & Policy Discussions

17:41 - Community Building Philosophy

27:07 - Startup Wisconsin Week 2025

33:40 - How to Get Involved & Support

34:03 - Upcoming Guest Previews

37:07 - Outro & Contact Info

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Mon, 4 Aug 2025 23:07:12 +0000 jacob@startupwi.org (Jacob Miller, Andrew Verboncouer) https://www.startupwi.org/podcast Welcome to the Startup Wisconsin Podcast! Join hosts Jacob Miller and Andrew Verboncouer as they share their vision for building a thriving statewide tech startup community across Wisconsin.

In this first episode:

🏛️ How we're supporting founders from Green Bay to Milwaukee to Madison

🎯 Our approach to year-round community building beyond just Startup Week

🤝 Plans for supper clubs, mentorship programs, and meaningful networking experiences

📅 What to expect from Startup Wisconsin Week 2025 (November 10-14)

 

Featured Topics:

→ Wisconsin startup ecosystem

→ Tech entrepreneurship in the Midwest

→ Community building for founders

→ Startup networking and mentorship

→ Wisconsin venture capital and funding

→ Green Bay, Milwaukee, and Madison startup scenes

 

Upcoming Guests Include:

→ Founders from Siren (Madison sales simulation platform)

→ Beth Ott from Starting Block Madison

→ Dan Fogarty on thought leadership

→ Casey Cammilleri, Sprocket Security

→ Ben from Fauna Bio (space hibernation research!)

→ Nick Myers, Red Fox AI exit story with Recovery.com

 

Segments:

00:00 - Intro & Welcome

00:39 - Meet the Hosts

04:03 - Startup Wisconsin Mission & Vision

05:40 - Why We're Doing This Podcast

11:08 - Types of Guests & Conversations

15:29 - Sponsor Message

16:56 - Government & Policy Discussions

17:41 - Community Building Philosophy

27:07 - Startup Wisconsin Week 2025

33:40 - How to Get Involved & Support

34:03 - Upcoming Guest Previews

37:07 - Outro & Contact Info

Podcast Sponsor

Valency Fund

Flexible funding solutions designed for sustainable growth of Wisconsin companies.

Learn more at https://www.valencyfund.com/

🔻 Connect With Us 🔻

Subscribe to the Startup Wisconsin Newsletter

https://www.startupwi.org/

Upcoming Tech and Startup Events in Wisconsin (400+ every year)

https://www.startupwi.org/events

Follow us on LinkedIn

https://www.linkedin.com/company/startup-wisconsin/

Connect with Jacob Miller:

https://www.linkedin.com/in/kineticbear

Interested in being a guest? Reach out!

jacob@startupwi.org

Startup Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.

This podcast is made by your friends at Headway.

https://www.headway.io

]]> Building Startup Connections Across Wisconsin's Growing Tech Scene Jacob Miller, Andrew Verboncouer 00:38:04 Meet the hosts behind the Startup Wisconsin Podcast, Jacob Miller and Andrew Verboncouer. Learn about our mission to connect Wisconsin tech startups, upcoming Startup Week 2025, and how to get involved in building the state's entrepreneurial community. Meet the hosts behind the Startup Wisconsin Podcast, Jacob Miller and Andrew Verboncouer. Learn about our mission to connect Wisconsin tech startups, upcoming Startup Week 2025, and how to get involved in building the state's entrepreneurial community. startup stories, tech startup stories, tech startup advice, startup wisconsin, midwest startups, madison startups, tech, milwaukee startups, wisconsin startups, startups false full 1