In this episode, Oliver and Tom discuss:

• The Jenga tower explanation of why biodiversity loss threatens everything we've built as a civilization
• Why Oliver chose business over marine biology — and whether he regrets it
• How he built a community of tens of thousands on LinkedIn by being a messenger rather than a marketer
• The business model behind Wildya, from free LinkedIn content to paid bootcamps and one-on-one consulting
• Why the CSRD rollback and Trump's reelection killed his corporate pivot — and why the timing was just wrong
• What "rewilding your backyard" actually looks like, and the three steps any individual or business can take today
• Why biodiversity is a long-term business investment, not a cost — and how compounding returns apply to nature just as they do to capital
• The IUCN tool that shows you exactly what's threatening species within 50 kilometers of your home
• The butterfly that nested on his Berlin balcony and what it taught him about positive feedback loops
• Why personal branding isn't self-promotion — and why the messenger matters less than the message

Resources mentioned:

• 1% for the Planet directory: www.onepercentfortheplanet.org
• IUCN Red List species threat tool: www.iucnredlist.org
• Wildya community: wildya.com

AI is fundamentally changing how SaaS companies should think about pricing. When your software makes teams 70% more efficient, charging per seat means you're literally shrinking your own market. In this conversation, product management veteran Lee Bridges explains why seat-based pricing is a burning platform and what comes next.

Lee, returning to the podcast after five years, recently led a pricing transformation project that forced him to confront an uncomfortable truth: AI-driven efficiency gains directly reduce the number of seats customers need. His solution? Outcome-based pricing that aligns incentives between vendors and customers while future-proofing against AI disruption.

Guest

Lee Bridges - Cheif Product Officer at Inn-Flow, father, audio engineer, and vibe coder who recently completed a major pricing transformation project for a B2B SaaS company in the field service space.

Key Topics Covered

The Seat-Based Pricing Problem

• How AI efficiency reduces Total Addressable Market (TAM)
• The misalignment of incentives between vendors and customers
• Internal team conflicts created by per-seat models
• Why "reducing a team from 10 to 3" destroys 70% of your revenue potential

Outcome-Based Pricing Explained

• The difference between usage-based and outcome-based pricing
• How to identify and price meaningful outcomes
• The psychology of "you make money when your customer makes money"
• Avoiding the "nickel and diming" feeling of usage-based models

Real-World Implementation

• Case study: Field service sales teams (20 minutes to 90 seconds per quote)
• Tiered prepayment models with outcome "credits"
• Combining platform fees with outcome pricing
• When outcome-based pricing works (and when it doesn't)

The Future of SaaS and AI

• Why B2B SaaS isn't going anywhere despite AI hype
• The problem with expecting everyone to be a product manager
• Consistency, training, and the limits of LLM-generated experiences
• Vibe coding and no-code tools in practice

Notable Quotes

"If you create efficiencies that make a process so efficient that some number of people will no longer be necessary... you reduce the number of potential seats. You reduce the Tam."

"If I give you a dollar and you're going to give me $10 back, I'd be insane to not do that as many times as I can."

"You're really expecting everyone on Earth to be a product manager. That's just not going to happen."

"The most people don't have a high level of agency. They don't know what they want, when they want it, and they don't know how to describe it."

Practical Takeaways

1. Evaluate your pricing model now - If you're charging per seat and building AI features, you're creating a strategic vulnerability
2. Start with new products - Test outcome-based pricing with new offerings rather than risking existing revenue
3. Identify measurable outcomes tied to customer revenue - What metrics does your sales team already use when discussing ROI?
4. Consider hybrid models - Platform fees plus outcome pricing can balance predictability with value alignment
5. The complexity trade-off - Outcome-based pricing must remain simple enough to avoid litigation-inducing confusion

Key Takeaways:

• Leadership is more like parenting than marriage - guiding growth without coddling
• Every employee deserves empathy, clear vision, and understanding of their role
• The importance of preparation for difficult conversations, especially layoffs
• Creating psychological safety where team members can express emotions
• Leaders must recognize their power and influence over employees' lives

Key Topics Discussed

Building a Sustainable Business and Life Balance

• Managing a 15-employee company while raising two young children (ages 4 and 6)
• Finding joy in simple pleasures: working out, good food, and family time
• The reality of being a working mom in a small community where she's often in the minority

What Clear Star Creative Does

• Boutique marketing/growth agency focused on venture-backed health tech startups
• Two main service phases:
  • "Crawl Phase": Helping companies validate their target audience and go-to-market strategy
  • "Walk Phase": Building scalable marketing and sales systems beyond founder-led sales

The Evolution of Venture Capital

• Shift from investing in "dreams and ideas" (2015-2020) to requiring tangible results
• VCs now demand sustainable, repeatable business models rather than relying on individual founders
• Importance of building "moats" and differentiation in crowded markets

Marketing Philosophy

• Three ways CEOs typically view marketing:
  1. Core revenue driver
  2. Sales enablement ("make things look pretty")
  3. Brand awareness generator
• Focus on impacting business outcomes, not just creating content
• Taking a whole customer lifecycle approach from acquisition to renewal

AI's Role in Marketing

• Using AI as an efficiency tool, not a replacement for human relationships
• Current tech stack includes ChatGPT for ideation and image generation, AI note-taking tools
• Emphasis on maintaining human oversight and the relationship-driven nature of business

The Transition from Founder-Led Sales

• Common challenge for companies in the $10-50M range
• Difference between lifestyle businesses and venture-scalable companies
• Building repeatable systems that don't depend on the founder's personal relationships

Product-Led Growth in Healthcare

• Healthcare traditionally being sales-led but slowly adopting PLG approaches
• The complexity of implementing PLG - requires buttoned-up systems and user experience
• Warning about pulling product resources away from core development

Recent Business Challenges

Ashley candidly shared experiencing her "hardest six months ever":

• Lost entire core team within two weeks
• Lost major clients within two months
• Had to rebuild while maintaining operations and caring for family
• Learning to balance investment in clients' success with her own company's needs

Hiring and Team Management

• Focus on behavioral interviews and work ethic assessment
• 90-day probationary period to ensure good fit
• Emphasis on preventing burnout in high-paced startup/agency environment
• Importance of setting clear expectations and boundaries

Parenting and Business

• Exposing her daughter to the business world and strong working women
• Balancing being present for family while running a demanding business
• Teaching children about the value of hard work and financial independence

Key Quotes

"I'm in the people business. We are in the services business where we are building relationships."

"If we turned [marketing] off tomorrow, would it really impact our business? Probably not... We have to make sure that we are impacting the business in every single thing we're doing."

"The strategic person climbs to the top of the ladder, looks over the trees and says, 'guys, we're in the wrong forest.'"

"Don't let the facade fool you. It is hard as hell to do this and it will push you in every single capacity."

Resources Mentioned

• Clay (AI-enabled sales outreach tool)
• Apollo (sales outreach platform)
• ChatGPT (AI for ideation and content)
• Clear Star Creative website

Episode Takeaways

1. Focus over busy work: Strategic thinking means identifying the one thing that will truly move the needle
2. Relationships drive business: Especially in B2B services, human connections remain irreplaceable
3. Transparency builds trust: Being honest about capabilities and limitations creates stronger client relationships
4. Systems enable scale: Moving beyond founder-dependent operations requires intentional system building
5. Resilience through adversity: Even successful entrepreneurs face major setbacks - persistence and support systems are crucial

Fortune's Path podcast helps service and technology businesses address root causes that prevent rapid growth. Music and editing by Ted Noser.

Topics Discussed:

• Anderson's role leading talent and leadership development initiatives at Shore Capital Partners
• How Shore Capital works with micro-cap businesses (typically small, family-run businesses) to help them scale
• The Shore Leadership Academy's approach to developing leaders at different stages
• How Anderson's background in fine arts influences his approach to business and education
• The importance of trust and communication as foundations for leadership
• The connection between art, education, and business leadership
• How Shore Capital evaluates potential business partnerships
• The growth strategy of consolidating small businesses to create mid-market companies

Key Takeaways:

1. Shore Capital Partners invests in micro-cap businesses with the goal of helping them scale, focusing on companies where the founders want to remain involved and grow with a strategic partner.
2. The Shore Leadership Academy focuses on developing leadership at all levels, from first-time managers to executives, with a curriculum that progresses from self-development to team leadership to strategic business thinking.
3. Anderson attributes much of his approach to business and leadership to his background in fine arts, particularly how it taught him to see differently, accept feedback, and continually iterate.
4. Trust is described as foundational to leadership, with three distinct dimensions: personal trust, organizational trust, and strategic trust.
5. The best teachers (and leaders) combine authentic passion for their subject with the ability to make content relevant to learners' real-world experiences.
6. Anderson describes education as being about delivery, while learning is about what people do with knowledge - applying it in new and interesting ways.
7. Shore Capital's investment strategy looks for "barbell industries" where there are many small players and a few large ones, creating opportunity to build in the middle through strategic acquisition.
8. Business success ultimately comes from human relationships: "We're humans working together with other humans and human-created systems to provide products and services to solve problems for other humans. And we call it a business."

Guest Bio:

Anderson Williams serves as Principal for Talent Development at Shore Capital Partners, leading their talent and leadership development initiatives. With a diverse background as a classroom teacher, entrepreneur, sculptor, painter, writer, and corporate advisor, Anderson brings a unique perspective to leadership development. He holds a Master's in Fine Arts from Cranbrook Academy of Art and has been with Shore since 2021.

• Tom: Setting up today's discussion points: establishing new standards in software, using tech for effective learning, and the possible conflict between educational system administrators and students.
• Guest: David Ells, Managing Director of Open LMS, an open-source learning management system provider.
• Overview of David's background in online learning with over 15 years of experience, including work with the Department of Defense on the Experience API (XAPI).

[00:01:09] - Early Career and Entry into Learning Tech

• David: Shares his accidental entry into the learning tech field after earning a master's degree from MTSU.
• Initial job at Rustici Software leading to a career in educational technology.
• Discusses the meaningful impact of developing educational tools and the transformative power of education.

[00:03:53] - Importance of Experiential Learning in Hiring

• Tom: Probes the significance of certifications versus experience in hiring.
• David: Emphasizes experience and practical application of knowledge as primary hiring factors over certifications.

[00:05:35] - Introduction to XAPI

• Tom: Attempts to describe XAPI.
• David: Explains XAPI's basics—data format and communication protocol for learning events, allowing detailed tracking of learning activities across various platforms and contexts.

[00:07:37] - XAPI's Vision and Development

• Tom: Shares initial skepticism about XAPI but appreciates its potential.
• David: Discusses the broader vision of XAPI, including data mobility and creating verifiable credentials for lifelong learning records.
• Insights on corporate and academic applications and interoperability with different forms of learning content.

[00:10:52] - Industry Adoption and Impact of Standards

• David: Describes efforts to establish XAPI, parallels with existing industry standards, and the critical role of adoption.
• Historical context of SCORM and the unique challenges and opportunities it presented.

[00:15:00] - Rustici Software’s Contribution to XAPI

• Tom: Questions about Rustici’s role in developing SCORM and transitioning to XAPI.
• David: Details Rustici’s research and industry contributions leading to XAPI’s development and its collaborative approach.

[00:21:00] - Launching and Promoting XAPI

• David: Discusses the practical and marketing challenges in launching a new standard and gaining adoption.
• Realizations and reflections on what might have been done differently for better adoption rates.

[00:28:10] - XAPI’s Broader Applications and Limitations

• Tom: Explores XAPI’s potential beyond learning contexts.
• David: Outlines XAPI’s flexibility, acknowledging both its strengths and weaknesses, and practical applications in data-driven contexts.

[00:38:08] - Managing Data with Watershed

• Tom: Discusses the potential overwhelming amount of data XAPI could collect.
• David: Describes the importance of filtering data to extract meaningful insights and the role of tools like Watershed in this process.

[00:43:42] - Transition to Open LMS

• David: Talks about his move to Open LMS and the shift in focus to higher education.
• Differences between corporate and academic markets and the commonalities in learning management needs.

[00:45:03] - Comparing Corporate and Higher Education LMS Needs

• David: Discusses the evolving needs of universities to prepare students for careers and the corporate focus on skills-based training.

[00:50:14] - Conflict Between Learners and Administrators

• Tom: Expresses views on the inherent conflict between learners and administrators.
• David: Compares this to IT departments versus end-users, discussing the potential synergy with modern SaaS and cloud-based solutions.

[00:58:16] - Future of EdTech and Learning Systems

• David: Envisions a future where learning is skills-based and highly personalized, breaking the traditional degree format.
• Discusses the potential for more granular and modular learning experiences.

[01:00:10] - Collaborations Between Academia and Industry

• Tom: Asks about formalizing partnerships between universities and industries.
• David: Discusses the potential for these partnerships, acknowledging existing informal pipelines and the mutual benefits.

[01:02:17] - Personal Goals and Vision for Open LMS

• David: Shares his aspirations for the growth and success of Open LMS.
• Emphasizes the adaptability of Open LMS and its potential leadership in emerging educational trends.

[01:02:54] - Conclusion

• Tom: Thanks David Ells for the conversation.
• David: Expresses enjoyment and appreciation for the dialogue and Tom's writing.

• “Applying to college is a series of tasks where you need information, guidance, and you need support through your own discernment process. It doesn’t have to be terrible. It doesn’t have to be scary.”
• “I use the word discern a lot. And I do that intentionally to discern who they are. Because when you start a college as a freshman, you're not the same person you are when you finish as a senior. And we need to get that right environment where it can be flexible and support that kind of academic, social, and emotional growth.”
• “…what's your philosophy of education? Do you view it as a means to an end, or is higher ed kind of this banquet table, you go and you feast and you try things, and it's just important to know what you don't like as it is to find out what you do like and what you're passionate about. We need to be strategic and intentional with choices for our students.”
• On her pro bono clients: “Helping them realize their potential, but to also broaden…horizons…look at it through this lens.”
• “If someone starts off a conversation, I want my child to go to a really competitive school. There's a lot to unpack in that statement. Once we start teasing out those factors…what I'm really hearing is I just want the best for my child. I don't know what that means. I don't have language around this, so I'm going to say an Ivy, I'm going to say, the best, the most competitive and what the most competitive for I'd say the majority of people isn't always the best decision.”
• If you work with Beth, you’re getting a process, not an outcome. It’s sometimes hard for parents to understand.
• “Children learn what they live. When they're shown another way. They're always receptive. I always said I can work with any student - parents: That's a different story. Kids are not the issue.”
• “Sometimes people just need to be reminded that they can do hard things.”

9:22 - How to navigate self-pay by removing fear-based thinking (I must have health insurance) and negotiate with every single healthcare service you pay for. 

11:02 - The freedom that comes with leaving health insurance behind and embracing self pay.

11:58 - How hospital foundations and patient pay advocates have emerged to embrace (somewhat) self-pay.

12:49 - As a high earner, she does not use these foundations, but negotiates to pay her bill. She's also a member of Christian Healthcare Ministries (CHM),  a health cost sharing ministry. 

13:20 - How CHM works - you become a member, pay a monthly fee. When a healthcare episode arises, you access CHM to get your healthcare bills paid, or shared. 

15:14 - Sloane details the self-pay patient journey, how self-pay doesn't trickle through to all areas of the healthcare industry, and how to educate each sector about self-pay.

22:50 - How to ask for the self-pay rate as a patient.

25:00 - Where Sloane negotiated for care from one provider that was 75% less than what another provider quoted. 

26:35 - How physicians are fairly  knowledgeable about self pay, but those in their business offices are not. They are trained to work with insurance. She packs her "patience and grace" to ask them to do something that is unusual. 

29:25 - Tom pivots the conversation to how Sloan copes with a diagnosis of a terminal illness (at age 23). She doesn't let it define her, and looks at her condition as a chronic illness. 

30:23 - How Sloane and Tom agree that it is the dying person's responsibility to prepare the living  for their own death. 

34:14 - Why doctors ignore DNRs (hint: it has to do with litigation). 

35:10 - Tom laments that modern Stoics don't talk suicide the way the original Stoics did - it is the last vestige of our wills. 

37:50 - Sloane shares her grandmother's advice about friendship: you really only need 6 friends in life; 3 on one side of the casket, and 3 on the other. 

38:10 - The extreme rarity of having one really close friend. 

40:00 - Shifting to business, how she found herself in Nashville's health tech scene. Pre-pandemic, it was crowded, healthy and vibrant. Backed by Nashville and nationwide private equity and venture capital firms, and also supported by local institutions like the Nashville Entrepreneur Center, Nashville Healthcare Council, local family funds, and others, founders were getting a lot of support. 

41:13 - When founder-led companies become responsible for creating shareholder value. The trajectory to create shareholder value is a big change, and she learned how sales and marketing played such a significant role in creating that value. 

42:35 - Creation of her secret sauce: the strategy/methodology/execution of marketing to build to exit, and understanding how to make quick pivots as needed. 

44:02 - What healthcare doesn't talk about post-pandemic: the rise in chronic disease, chronic care. Fortunately, many tech companies have come forward to begin to address this issue, but the exits are not as speedy as they once were.

45:29 - The role of a strategic story in an exit, and how your fly paper is still whether or not you created shareholder value. But healthcare needs to re-think intellectual property.

47:00 - The other way to re-frame and look at shareholder value: the customer relationships you create. If you can own a swim lane in the market, and really own it well, that has enormous value. 

48:16 - How mergers often destroy value by devaluing the brand and the culture. 

51:24 - Who shaped her marketing philosophy, Marty Neumeier, who was Steve Jobs' brand mentor. She believes, as Marty maintains, that a brand isn't what you say it is, it's what your customer says it is. 

54:17 - How she loves founder-led companies, and how she gets so much more out of it than what she put into it. Her emotional paycheck gets cashed every time she sees someone get a check they never thought they would get.  

• Selling into healthcare takes a long time - for good reason.
• Having worked in both the education and healthcare market selling software, both are difficult markets. While healthcare has more budget than education, both take forever to make a decision.
• Young entrepreneurs should think about getting some enterprise-level experience before starting a company.
• How entrepreneurship is like parenthood: you don't know it until you try it.
• Early technical decisions can have an outsize downstream impact, and is perhaps more important than go to market activity.
• Moore's most important job as CEO was first to drive revenue, then later to set the company vision and cultivate its culture.
• In his current role as an advisor, he stresses operational discipline over founders habits.
• The number one attribute for entrepreneurial success? Being able to work through ambiguity.
• Managing customers and raising kids both involve cultivating their independence from you.
• Jason's favorite saying? "People gonna people." It's not just negative - people also do amazing things. But just know that folks will disappoint you at some point.
• Advice to his 23 year-old self: Push through the hard times and keep people close; don't lose your focus on them.

• Why it's not so much that Eric is a believer in alternative assets, but that he believes in a diversification of investment portfolios. 
• That illiquidity of alternative assets is a feature, not a bug. 
• The legal challenges of getting Alto started took longer than the anticipated technical challenges of simplifying the workflow processes of alternative investments.
• The 'greater fool' theory in investments.
• How public markets are no longer being driven by the fundamentals of investing and operating.
• Alto's three levels of operation: a software business which owns a trust company and also owns a securities company.
• 'Historically good returns' in alternative investments = returns that exceed public market returns.
• Bitcoin, like money, is an invention based on faith.
• What comprises 'luck' in business: hard work, opportunity, and a third vector: remaining open to what's happening in the market.
• The cost - and there is one - to entrepreneurship.

• Understanding the basics of circuits and quantum computing is essential in comprehending the potential of AI.
• Transparency and explainability are crucial in AI decision-making to ensure accountability and mitigate bias.
• Data curation is a critical step in developing AI models to avoid unintended biases and improve accuracy.
• The application of AI in mortgage and loan decisions requires careful consideration of fairness and ethical implications. Higher education is correlated with earnings, but its correlation with credit worthiness is uncertain.
• Being completely blind to factors like race and gender in the hiring process may be challenging, but efforts can be made to represent everyone equally.
• Considering each subpopulation separately and simplifying the hiring process can help ensure fair representation.
• Ethical dilemmas arise when ignoring correlations that have a strong statistical relationship with outcomes.
• The application of AI in the hiring process can be effective when combined with human decision-making and a structured, data-informed approach.

Chapters

00:00Introduction and Recording Confirmation

00:38Background in Physics and Engineering

03:13Research in Material Design and Quantum Physics

04:26Understanding Circuits and Quantum Computing

06:37Transition from Research to Business

11:14Impact of Ideas and Einstein's Equation

13:14Ethics and Risks of Artificial Intelligence

17:15Applications and Limitations of AI

20:39Ethics and Bias in AI Decision-Making

25:24Transparency and Explainability in AI

29:29Data Curation and Bias in AI Models

34:07AI in Mortgage and Loan Decisions

38:15Fairness and Ethics in Lending

38:41Correlation between Higher Education and Earnings

39:21Challenges of Being Blind to Race and Gender

39:49Considerations for Representing Everyone Equally

40:24Ethical Dilemmas of Ignoring Correlations

41:08Product Development and Answering Ethical Questions

41:29Simplifying the Hiring Process

42:02Data-Informed Recruiting and Hiring

43:14Using Data to Find the Right Match

44:24Simplifying the Workflow for Recruiters

45:16Focusing on Skill-Based Factors in Hiring

46:31The Validity of Resumes in Predicting Performance

47:25Factors in Deciding a Good Hire

48:15The Tricky Nature of Job Descriptions

49:05The Importance of Skills and Job Descriptions

50:03The Value of Experience and Starting a Business

51:09The Role of Emotion in Decision-Making

54:02Introducing Scientific Process into Hiring

55:53The Application of AI in the Hiring Process

56:58The Human Element in Decision-Making

58:16Applying the Scientific Method to Business Problems

59:18Learning from Past Research and Being Skeptical

01:00:45Checking Assumptions and Being Discerning

Every new material and material supplier is tested, based on internal standards. Once it moves to being manufactured on the production line, further testing and checking take place. 

Some analogies and differences - software vs. manufacturing: 

• multiple suppliers and producers are comparable to software engineers writing code all over a complex system
• the value of eliminating variation
• unlike software, there's no opportunity to "fix it later" in manufacturing, which makes it essential to build a highly functioning quality process
• quality and compliance can't be an afterthought in manufacturing 
• software and manufacturing need to focus on root cause analysis to build the most robust quality management process
• risk analysis is all about error tolerance 

Chris joined the Fortune's Path podcast recently from Stanford University, where he was attending a venture capital workshop for promising early stage businesses, to touch on a variety of issues like:

• What’s the best way to incentivize workers? How does Trunk Tools provide immediate financial benefits to them?
• How do you bring technology to construction and improve outcomes for everybody?
• What is it like to build a technology company from scratch?

These are some of the question Tom asks sales and product management veteran Amin Haidar, a six year veteran of Asurion, one of the largest and most profitable private tech companies in America. Tom first met Amin while he was still in college, working full-time at Healthstream while getting his degree. His intelligence, ambition and work ethic made a great impression on every one in leadership, To, included.

Amin and Tom discuss how the Shape Up methodology works, how to choose what ideas to invest in as a product manager. Amin discusses how Asurion time-boxes work into five week chunks and focuses their teams work on one thing at a time with seven person teams. Amin talks about how avoids client commitments and manages his now timeline, how he manages urgent requests, how he judges the effectiveness of his product managers, and how he gives feedback in the moment. Amin describes product management as the art of creating a process that creates great products. Amin talks about his transition from a start-up to a large mature organization like Asurion. Amin talks about his style as servant leader and when he knows he needs to be directive and what he does to support his reports when that happens. Amin talks about how he encourages his reports to question him how he tries to have no ego with his teams. Amin talks about leadership’s job is to make everyone else successful and how he creates a context for making decisions by keeping things objective as much as he can. Finally, Tom andAmin talk abut the meaning of success and raising kids.

Teja has been a CEO for ten years, though he’s less than 40. Teja loves working with people and solving problems. Teja describes how business is a canvas for solving problems, and that solving problems and making money are the most fun parts of being a CEO. “People assume I’m smart because I’m a CEO, so I’m challenged less because I have this silly job title,” says Teja. Teja talks about Brazilian Jiu Jitsu and how he enjoys it as a domain where nothing is expected other than respecting others. Practicing Jiu Jitsu helps Teja get space away from work to improve his problem solving. Teja talks about how he obsesses about problems even though he knows intellectually that getting away from a problem for a while sometimes helps solve the problem. Tom talks about how meditation helps him when he’s stuck even though he can never quiet his mind. Teja tells Tom what’s the right cycle on which to update his clients about the progress of their engagement and how gun.io prevents surprises and avoids conflict with its clients. Teja discusses the psychology of raises and how no matter how much we’re paid, we get aggravated if we go a year and don’t get a raise. The conversation gets cut off when Teja loses power because of tornado winds in Nashville, but everybody ends up OK.

Eric discusses his daily work rituals, how he reviews goals with cross-discipline teams, and the joy of creating a product that solves users’ problems. Tom asks Eric whether he would prefer to have a good boss or be a good boss. Eric explains that constantly asking “why” is the key to building up your curiosity muscle. Tom wonders if you can apply product management principles to family life and Eric gives living proof by sharing his family roadmap for 2021. Eric talks about scoping your goals to fit your means. And Tom casually mentions reading some Seneca.

Tom asks Bill how you decide where to focus your energy as a leader. Bill says that the key is to start with five disparate data points before you make any decisions. But it’s crucial to dial in and really listen to what you’re being told - don’t listen to see what fits the story that you’re looking for. Tom and Bill discuss the limits of what you can control as a leader. Tom asserts that investors don’t talk about customers enough in board meetings. And Bill explains that you have to tell the customer story in a language that expert money managers can understand. Bill talks about how hard it is to fire people and Tom confirms that you can’t fire your kids when they fail at the tasks you’ve assigned them to do.

Tom asks Anne if the purpose of marketing is to generate sales. She calls “total bullsh*t” and leads a conversation on building love, trust, and consistency through marketing, making connections to dating apps and parenting. Anne explains why gambling with trust is such a dangerous game. Tom and Anne talk about empathy in corporate governance, the three rules of parenting, and why Diversity, Equity, and Inclusion make some people so uncomfortable. Tom asks Anne the impossible question: How do you define love? And then he asks her about God. In the end, Anne brings it all back to a few simple rules: shut up; listen to what people need; and help them achieve it if you can.

Tom and Shannon talk about how to listen to customers and why customers sometimes misrepresent their needs, why healthcare delivery was upended even before COVID-19, and why good marketers need to understand their customer's business model inside and out. Tom and Shannon also talk about scaling a market and do some on-the-fly product development for one of Shannon's favorite products. Shannon tells how the annoying habits of co-workers may be evidence of their superpower, what outcomes marketing can guarantee, and what operational and technical challenges prevent accurate marketing attribution in healthcare. Finally, Shannon tells Tom how her interest in stoicism and religion has influenced her as an executive.

Tom and Chris talk about Chris's transition from project manager to product manager and play a game of "spontaneous product development" to create a product to disrupt the U.S. education market. They also talk about the signs of a healthy product and how Built Technology is creating an ecosystem for construction finance and lending by automating manual processes and consolidating data. Finally, Tom and Chris talk about the profession of product management and where it's going, why business savvy is a growing need for the best candidates, and how Chris views getting inspiration from competitors.

Joshua Oakes, twenty years veteran of client services, product management, and marketing talks with Tom about the Who First framework and how it helps businesses create and sell products effectively. Josh believes understanding your customer is always the most important thing. Who First is a structured methodology for getting verifiable data about who your audience is, what they care about, and what they think about you. Josh shows Tom what a customer interview is like using Who First and how he's working to turn his professional service into a more scalable product. Josh also talks about creating business metrics that reflect who your business is trying to serve and why he hates marketing personas. Tom and Josh then go on a run about how getting past personas is like a post-racial world, how the reality of why buyer's make purchases is often different from the demographic theory, and why Simon Sinek's Start with Why might be wrong that having a higher purpose for your business translates into measurable results.