Alli spent her 20s in New York City, doing PR and styling hair until she met her ex-husband and pivoted to the stay-at-home-mom gig. “I thought it was the coolest thing ever: I get not to work? I thought I had hit the jackpot!” But after a half-decade of staying home with her two sons, she was bored. So she launched a mobile business called Straight At Home, pitching her blowouts on parental message boards and bringing a luxury that had been previously reserved for the glitterati to moms all over L.A. 

She quickly learned that her business model—which included paying for a babysitter and a lot of gas money—was barely breaking even. But when she tried to pull back, she found that her service wasn’t really available anywhere else; her clients would either skip the little luxury, or they would make do at an all-purpose salon that got the job done but lacked that special touch. She envisioned a hair salon that got straight to where the magic happens: those final moments of a haircut that really put the oomph in the style. From that vision came Drybar.

Instinctively, she knew that she wanted the Drybar experience to be predictable for clients, replicating the same style and services across the country. She even provided the salon tools, bucking the industry norm that stylists provide their own. “Aesthetically, I had this idea of what I wanted, which led to knowing that, whenever you go to a Drybar, you have the same experience.” This meant that clients could trust whoever was doing their styling, no matter what shop they were visiting. 

In the early days, clients pushed for Alli to expand her services. They asked for manicures and makeup services, and while Alli considered it, she ultimately decided against it. “We do one thing, and we do it really, really well.” Then, investors looked at her client volume and said they were crazy not to offer them more products, more services, more everything. Alli’s response? “I don’t want to.” To this day, Drybar offers a limited range of services that focus on great hairstyles, and they’ve grown to 150 shops nationwide. 

That doesn’t mean she never expanded her business. From the beginning, Alli wanted to develop a line of harmonized hair products that would all work together. So when she raised her first round of funding, she ensured that, while the stores remained the focus, some of the money was earmarked for hair products. Her first partnership, with Sephora, helped launch Drybar from a place women went to something they could use in their daily life. 

Alli’s gone on to launch other exciting brands, including Okay Humans, focusing on a “modernized talk therapy experience,” and Squeeze, a massage studio that is her brother’s passion project. Alli says that her own divorce and a chance meeting with a newly licensed family therapist inspired her to “create an experience around talk therapy.” She’s gone on to take an advisor-investor role with The Feel-Good Company, a collection of businesses aimed at making clients feel, you know, good. (She also helped launch the jewelry line Becket + Quill, proving that self-care comes in many forms.) While each business focuses on a single element of personal care, the Feel-Good umbrella takes care of HR, marketing, and other needs. 

This is our final episode of season four of I Make A Living, but don’t worry—we’ll be back soon with more stories of successful entrepreneurs and amazing business advice. We love to hear from you, so keep in touch on Instagram and Facebook and, and don’t forget to check out FreshBooks, the accounting software that’s perfect for small business owners like you!

Before she even got started, Natasha wanted to “change the game” when it came to ice cream and who it was for. Freya, Natasha’s wife and co-founder, is a woman of colour, and they were both tapping their identities as queer women and millennials.  “We saw this opportunity to be pioneering,” she says. Without much food experience—Natasha was fired from her one and only catering gig—they launched into the ice cream business headfirst, convinced that if they didn’t shoot their shot, someone else would. “The recession had just hit, it was just way too risky.” Their first “ice cream truck” was a “barely driveable” former postal vehicle they had towed (!!) to 2009 Coachella. Since the truck was more set dressing than operable business location, they gamely set up a tent beside it, and started serving. 

Natasha knew that Coachella’s crowd was who they wanted to focus on as their core audience: millennial, highly influenced by the desert heat and music fest vibe, armed with expendable income, and in a heightened state where “you might be buying a lot of ice cream and eating all of it.” For Natasha, she wanted to connect her product with people’s memories of their Coachella experience. 

Natasha and Freya started with a minimum-viable-product mentality, and knew that if Coolhaus flopped, it would be a fun experiment, not a financial catastrophe. They planned for a little bit of success—a website with some pictures, a Twitter handle, a logo, and they filed the business through LegalZoom (which turned around and named a conference room after them a few years later). Their low profile during the early days gave Natasha permission not to strive for perfection, but switch it up when something wasn’t working. “We are the audience, so we asked if this was something that we wanted.” 

After Coachella, they an exposure boost from CurbedLA, which highlighted their “weird flavours and “strange puns,” and helped get them to the next level: they gained more than ten thousand Twitter followers in the span of hours, and got requests from media outlets like Eater and Dwell. “You can’t plan for that,” Natasha says. “You can’t plan to go viral.” She and Freya had to make a decision: were they going to do this thing for real? 

They were. “We immediately got the truck fixed so it could drive,” she laughs. They focused on both street sales and catering, and their first catering customer was MySpace. Initially, they had forecast for more sales through the truck, but within a few months, the catering business was the primary component. “That was the problem we ended up solving.” Now, 95% of their truck business is through private catering, and they have two brick-and-mortar stores in Los Angeles. 

Natasha has been both a Disney Imagineer and an architect; add in ice cream, and she’s created “farchitecture.” She says it’s “food plus architecture,” a riff on her college professor’s criticism of a project that he said looked like a layer cake; her response was to bake her next model. Food and spaces are her “two passions,” and bringing them together to build special, memorable moments was not a business at first but a “passionate hobby.” Her experience at Disney helped her see how this outlook could be transformed into something more entrepreneurial: “I learned a lot from that experience.” But her “farchitecture” idea did get off the ground during her Disney days: while 2008’s recession was unfolding, she started making ice cream sandwiches to “lighten the mood” for her colleagues. 

Her future wife and business partner thought the sandwiches were an amazing, quirky idea, and they’ve been together since the earliest days of the company. Navigating both business and romance in the early days was romantic—they were travelling to weddings in Ojai!—but being together all the time also supercharged Coolhaus’s operations. While things haven’t always been smooth (“Freya and I have very different management styles”), things have generally been great. “I mean, yeah, spoiler alert: we’re married and have two kids. Things worked out.”

Ben has a passion for tech – he was the kid in primary school who would “be taking apart the printers,” and at a young age, he was tapped by a family friend to build her website. He brought some previous experience to the job, and filled in the gaps by watching YouTube tutorials on things like how to add contact forms. He netted himself $50 and was super jazzed. Like many youthful entrepreneurs, his first expenditure was candy. But he’d caught the bug. He freelanced for most of his teens, ultimately selling his digital agency Towers Design to Zest The Agency in 2017: a buyout before legal drinking age.

Growing the company meant growing out of his “craft,” which was coding, and into management and leadership. He stayed engaged in the work by allowing himself to sit in on client creative sessions, giving him a bird’s eye view and input in the creative ideation, without getting caught up in the nitty-gritty of the day-to-day. Ben managed 26 people by the age of 18, working with brands like Virgin Racing, and he credits his mentors with helping him get an array of skills. “For me, mentoring is not about having one person who is your mentor; it’s about having multiple mentors.” Ben started collecting his mentors when he was in his teens, calling on people to share their expertise in sales, marketing, finance, and other areas. Never having had a boss before, Ben knew he couldn’t rely on his own experience in the workforce to guide his management style, so he had to use his mentors’ inputs and opinions to help him lead his team. 

Before COVID, Ben maintained a robust speaking schedule, which he credits with helping him grow his client base. Clients included the inaugural Young Enterprise with the UK government, aimed at unlocking a Silicon Valley mindset in England, and working with the British Royal Family on their initiatives. He used COVID as a chance to reset a bit—”leave the laptop at home”—and travelled through India and Thailand, falling in love with the local focus on community.

This focus influenced his work on Tahora, his community and culture app that he started in 2020. Tahora is designed for employees and their psychosocial needs, aiming to enrich their work community through better connections. He says that 47% of people don’t have a close friend in the workplace, leaving many folks without a sense of camaraderie and connection for long hours of the day. He shares the story of two employees who had trained for the same half-marathon without ever talking to each other about their hobby; his POV is that people’s well-being at work can be supported through friendships. Tahora comes from the Maori concepts of health and togetherness. “So often, we see community as just a group of people. In the Maori community, everyone has a part to play. Everyone belongs.”

When Erin Bagwell decided to turn to Kickstarter to get her movie off the ground, she didn’t expect to raise over $100K in 30 days, but that’s exactly what happened. Erin’s movie, Dream, Girl, is about the real-life experiences of ten New York City-based female entrepreneurs, and it turns out audiences were hungry for this type of story. Erin watched as women who were longtime experts in their field would have to prove themselves to boardrooms full of men in order to secure funding. “Wanting to be seen as an expert, wanting to be taken seriously, that’s still a big one,” she says. She needed to tell their stories.

So she pitched it on Kickstarter, and supporters were here for it. Erin credits her “really fabulous video” as the prompt that got people on board. “I spent a lot of money and I had a gorgeous video because I wanted people to look at it as a trailer. A glimpse of what the film would look like.” Erin invested in audio mixing, color correcting, and all the standard-issue Hollywood things to ensure that it looked amazing. “If you’re investing in a documentary, you want it to look, you know, like a film.” 

Dream, Girl went on to premiere at the Obama White House in 2016. Erin was able to design a successful afterlife for her film. In her first full year of filmmaking, she made over $100K in sales and employed a team of two. She worked directly with her Kickstarter backers to bring the film in front of audiences and supplemented the screening income with a robust speaker’s schedule on top of that. 

Erin’s twin inspirations for her first documentary had been her own experience being sexually harassed at work, and the collection of anonymous stories she collected into a storytelling blog called Feminist Wednesday. She was seen as a member of the entrepreneurial community, “because I had started this little WordPress blog,” and she had contact with women who were raising capital and launching start-ups. A lot of Erin’s audience was female founders and entrepreneurs who “really wanted to create spaces for connection.” She also linked up with influencers who promoted the film—and themselves—for their audiences. “People want to know your why. Why are you passionate about something, what is it that excites you? People are really attracted to that.”

For her next project, Erin’s own pregnancy was the catalyst and inspiration. “I was really interested in how people mother,” she explains. Her own experience with postpartum depression changed her expected filmmaking trajectory. “We don’t get to see a lot of great authentic stories about what it means to become a parent;” in making this film, she set out to change that. She felt “called” to share the truths and vulnerabilities of her first year of motherhood, and it became a way of healing her experience with PPD. Reviewing the footage gave her a sense of grace and compassion for her own story. Her goal is to let other mothers see themselves in the messy, ill-fitting parts of the early days of motherhood, and our own Damona Hoffman shares her insights into balancing motherhood and entrepreneurial momentum. Year One is now available to stream on YouTube.

When he arrived in LA, he didn’t do the usual waiting tables gig: instead, he kept on with construction work. “As I hustled for work, I also learned more and more about construction.” He worked across many trades—HVAC, plumbing, tiling—and while he “was cheap,” he taught himself new skills by reading up on the subject. When home-improvement shows started to gain traction, Josh suddenly found himself uniquely positioned: he was an actor who knew about contracting. “I was literally, like, I don’t know which zebra I am: black stripes or white stripes?”

Since then, Josh has acted on sitcoms like Curb Your Enthusiasm, hosted competition shows, and been the resident contractor on HGTV and DIY Network home-renovation programs. He’s also been the head of his own contracting firm, so he knows all about what the camera doesn’t show. 

Josh is very aware that, like many other industries, contracting has its fair share of what he calls “scam artists:” people who fail to deliver or deliver bad products. While shady operators hurt in every industry, when it’s a home renovation, “the scars run really deep.” Building trust between a contractor doing the work and the client employing them is a major step. As contractors, he says, “we have to look at the other side: it’s their house, their lives, their security.” While the drama might be played up for TV viewing audiences, Josh knows that there’s an inherent imbalance in the relationship. “You might have one chance every twenty years to remodel your kitchen, and you’re talking to someone who remodels them daily.” It’s a lesson in trust-building that entrepreneurs across industries can learn from: how do you prove to your clients on day one that you can be trusted? 

2020 was a whirlwind of competing priorities that “smacked me in the face.” Josh isn’t immune from second-guessing his directions and decisions, and his experiments aren’t always successful. From trying to renovate a house by himself instead of with his usual eight-person crew (“brutal”) to the decision to pause his own contracting firm, it’s been a season of change. 

But it’s not all tough news: Josh has leaned into his passion for Boys Town, a residential organization serving at-risk youth. He works with their Trade Life program to help connect young graduates of the Boys Town facility with careers in the trades. (Josh explains that for at-risk kids who can keep clean records between the ages of 18 to 22, “their chance in life skyrockets. So this was a real easy one for me.”) He’s been involved with the organization since 2012 when he did a PSA for the Boys Town, and he fell in love with the mission. Josh helped them re-launch the Trade Life program and expand it to new industries, including car mechanics, welding, and culinary training. Starting as young as thirteen, kids can try different programs and figure out what works for them. Josh himself donates tools, helps connect the program to tool manufacturers, and raises money. 

Josh’s overarching philosophy isn’t a new one, but it’s a reminder of what can be accomplished through good communication. “Good, fast, and cheap: you can have two, but you can’t have three.” Josh is willing to work with clients on the parameters they set—budget, timeline, scope—but he brings decades of expertise and is able to gently guide them when they want all three. We love this philosophy, and we know we can use it in our own business relationships!

But a few months in and they were already getting ads. A little while later, they casually launched getaway events like the Being Boss Vacation and signed a book deal. The podcast was taking on a life of its own. 

Emily was already a successful web designer: she had gotten her start with her Etsy store, having fallen in love with the idea of selling handmade things online. It was during this time that she became “enamored with branding,” and diving deep into who she was serving and why they should care about her business. Eventually, she took her expertise and passion to other business people. She graduated from offering pointers on online banners to running Indie Shopography, her web design agency for more than a decade.

So when it came time to launch Being Boss, it was a bit of a lark. “We had no business plan. We were just starting a podcast.” Emily and Kathleen went through the usual steps they’d take with any client—from the name, branding, website, and content buckets—but initially, they didn’t plan to monetize their passion project. 

Their sudden success may sound amazing, but Emily cautions that it was “actually overwhelming.” The two of them experimented with a lot of different business tactics when they were building up the podcast, looking to see “what would stick.” Things weren’t always easy-breezy: their foray into Facebook Ads was a colossal failure, so bad they didn’t even do their customary postmortem. (Emily files aspects of their experiments under “what worked, what kind of worked, what didn’t work,” taking lessons from each. “It’s how we iterate and do the work we need to do to make the next time we do it even better.”)

And then: burnout struck. Emily says that the rush of opportunities on the podcast side, plus some setbacks in her personal life and other business, led to a feeling of burnout. For Emily, burnout felt like “Ew.” She found herself getting angry and listless when it came to work topics. “I was very much not myself.” 

“For a while, we thought we were going to shut Being Boss down. We were both so tired.” She set a date, and promised herself that if her homebrew remedies didn’t work by then, she’d get a therapist (and she did); she learned to recognize the way she felt leading up to a depressive episode (“a very deep tiredness”), and she shifted her priorities, giving herself more time. But the major solution for Emily wasn’t to walk away—it was to invest more deeply. While her co-host and partner Kathleen wasn’t ready to leave her day job, Emily wanted to go all-in. “Our solution for mutual burnout wasn’t the same solution.” 

Almanac Supply Co. started in 2018 because she found her podcast convos were starting to verge on the meta. “It didn’t sit well for me to show up as someone who knows business, but the only business I’m running is this podcast.” She thought back to her time as a web designer; she always “really envied” the folks who were working on product businesses. Pivoting to something nature-focused, hands-on and family-oriented—she even makes the candles with her partner—gives her a sense of purpose, and offering beautiful handmade items brings her back to her Etsy days, albeit with a major glow-up. “I get to show up and be the CEO.”

Resources

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Of course, you don’t know Sanjay because he’s a failed pizza emperor: you know him as the head of Mirage Data, a start-up that protects your data without sacrificing usability, as well as a founder of TogetherLetters. In his past, he co-founded Digital Envoy and Prototype Prime, and ran events like 2015’s Startup Riot. He’s also a host of Tech Talk Y’All, a biweekly comedy tech podcast. Is there anything this guy can’t do? (Besides running a pizza company...but we’ll forgive him for that.)

Like many entrepreneurs, Sanjay got his start in middle school. He was a candy-bar broker: buying piles of the sweet stuff and then selling to his peers. “If you ask a room of 100 entrepreneurs, more than 50 of them will say they did something like that.” He turned his early earnings into comic books, some of which he still has today.

In 1999, after graduating from Georgia Tech, Sanjay had an idea that would “make the internet better.” He noticed that the FedEx and IKEA websites were still relying on customers to select their countries before they could begin shopping, but suspected there was a tech workout-around that would smooth out that step. At work the next day, his colleague told him, “It’s either impossible to do, or somebody’s already done it,” but nope: Sanjay found that it was possible and he was first. Digital Envoy was born of this idea, and Sanjay left that colleague behind in 2000. Digital Envoy raised 1.5M in 2000, and 10.5M the following year; selling that first company in 2007 has let Sanjay “continue on this crazy entrepreneurial journey ever since then.”

A lot has changed since those heady early-internet days, and Sanjay isn’t nostalgic. For one, “You didn’t have the infrastructure stuff that we have now. You don’t need to buy servers. You don’t need to buy storage space.” While Sanjay’s early tech needs often gobbled up his large investments, “A lot of companies are able to start now without having to raise much money or any money at all.” Folks can now get in without huge initial investments, relying on quick, cheap, and global solutions like the cloud. 

Being a tech-minded entrepreneur hasn’t always been champagne and gala events. Holding patents means that Sanjay has had to sit through “excruciating” sessions in order to explain the nitty-gritty of his products, but doing so “builds a moat to protect the company.” He doesn’t go for the NDA mindset—Sanjay figures that, with seven billion people on the planet, someone else probably has the same idea as him, somewhere—and he says that talking about his ideas is one way of finding out who else is solving that problem, or even why the problem can’t be solved in the first place. 

He extends that philosophy to the way he approaches all his projects. “You’ve gotta become an extrovert when you’re an entrepreneur, at least in terms of business.” He credits his relationships with strengthening his business: from loyal connections to getting the support staff on board, and from funding events, to board service, relationships are where “good things happen” as an entrepreneur. Where are your best connections?

While Rebecca has enjoyed early boosts to her brand—Jenna Elfman wore her “I Love New York” shirt on The Jay Leno Show in 2001—Rebecca has also worked hard to cultivate her business’s profile. For example, when she launched the Morning After Bag (also known as the M.A.B.) in 2005, she leveraged her industry connections, working relationships with Hollywood agents and stylists to ensure that the highly photographed celebrities of the early aughts all had a Rebecca Minkoff bag on their arm. 

But getting there wasn’t easy: she’s navigated debts, doubts, and setbacks along the way. For example, Rebecca tells us she was once fired from a job after the CEO pulled her aside and told her that  if she didn’t start channelling the passion she was putting into her own side hustle into the CEO’s fashion business, she’d be let go. Rebecca countered with, “I don’t honestly think I can do that.” At the time, Rebecca had small collections in only a handful of New York City stores, but her dedication to her own vision meant letting go of her main gig. “There was no safety net,” she recalls. Rebecca has since been in the CEO’s position, and she’s made the same tough call. “When you’re half-assing two things, you’ll never be able to fully focus on either.”

When the M.A.B. took off, Rebecca sensed her company’s reputation was starting to hinge on a single product. So she quickly escalated production on a range of offerings, from jewelry to clothing. “We knew we wanted to be a lifestyle brand, and the only way to do that was to go full-force and launch these other categories.” Her company president at the time was from the apparel world, and Rebecca herself had experience with women’s clothing design. She also brought on a shoe expert who could take them from design to manufacture. “We kept finding best-of-breed partners.” Unwilling to do a licensing agreement, she entered into manufacturing agreements—very normal in fashion—and she encourages people to explore different types of partnerships for themselves in their own businesses. 

One of her most important partnerships is with her brother, who joined the company full-time in 2011. He had loaned her seed money for M.A.B. launch years earlier, and their partnership over the years has had ups and downs. Rebecca tells us that when things get really intense, she and Uri “hired a business mediator to help us when we get those critical impasses:” someone to “unsnarl the tangles” when the business and personal relationships become complicated. 

Since 2018, Rebecca has also been channelling her creative leadership energy into the Female Founder Collective, a network for female business owners that offers education and resources. She’s also recently published a book, Fearless, that walks readers through her 21 steps for bravery in the face of business uncertainty. “My goal with the book is to throw out the rules: know you’re going to be scared, but do those things anyway.” She knows, from long personal experience, that taking risks is not a fearless endeavor, but moving through fear is a key step for success.

Resources

To learn more about our guest, go to https://www.rebeccaminkoff.com/

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The early days took some adjustments. In the first six months, Paddy and his partners tried to divide up their roles and responsibilities, with Paddy taking on the marketing, sales, and raw strategy, while his co-founder focused on delivery and operations. But they soon discovered that divvying up the job didn’t mean better work. “Because we split our roles, we didn’t actually work together all that much, the way we had for the first nine months. We did our best work when we were working together.” Bucking convention, they got the band back together and decided to keep their business roles much looser. 

It’s this not-quite-conventional approach that helps keep Aira at the top of its game. While other shops might do SEO because a client asks for it, Paddy and his team slow the process down and dig deeper into how the client wants to grow.  He makes a point of pinpointing their client’s actual needs—ranging from content marketing to paid media—and how they interact with the business’s pain points (including tricky spots like investor pressure and pitch meetings). Aira takes a collage approach, offering a buffet of short- and long-term solutions that will both quiet a nervous investor and actually, you know, grow the business.

Paddy reminds us that SEO is not instant gratification: it actually takes six to twelve months to pay off. “As a company, the thinking has to be in years, not months.” For faster results, he suggests investing elsewhere, like in paid media or paid search in advertising. But he also reminds us to look at what we’ve already got: do you have a big email list that’s just sitting there? One-time customers who could be convinced to return? “What have you already got that you can leverage?”

Paddy’s ultimate goal is to create a work culture that lets people and businesses be themselves. He encourages his team members to watch their personal triggers—anything from skipping meals to not getting enough exercise—that can lead to crummy decisions or bad moods. He also recognizes that for some, Aira will be a stepping stone along a long career; he does his best to be a springboard, not a gate. Ultimately, he says, “We wanted to build somewhere where, if we were employees there, we would be happy to work.”

Resources

To learn more about our guest, go to https://www.aira.net/

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Before launching GoodPods, JJ—who was already a podcaster herself, with Been There, Built That—talked to more than 700 people about their experiences with podcasts. Those folks ranged from established producers and hosts to the casual listeners who tuned in a few times a month. At the end of those conversations, she had a wealth of knowledge and used it to release something special. “We launched a product that people liked. These were people who really enjoyed the app and realized that there was nothing else out there like it.”

JJ’s focus has long been on products that improve your life, but also give back. GoodShop, another project of hers, combines coupon codes for more than 7000 popular retailers with a chance to donate the difference to national and international charities (they’ve raised over $70K for the ASPCA alone). And SearchKibble’s mission is to feed pets living in shelters—each search on the site is worth two bites of kibble. JJ startedSearchKibble in large part because of the COVID-19 pandemic, when shelters saw a serious dip in donations. “It’s a way for people to do good while they’re doing what they’re already doing, which is search the internet.”

Her early days hosting Your Business made her a trailblazer in the small-business world. “Back then, there was nothing else like it. There was no Shark Tank.” She helped bring  stories of entrepreneurship into people’s living rooms and shared the good, the bad, and the ugly with viewers. “I was hosting the show at the same time that I was building my other company, and I was as much the audience as I was the host.” Over the years, she saw patterns of successes and missteps.

Which leads us to failure, an entrepreneur’s biggest worry. “The number-one thing that successful people can do is deal with failure.” She tells us the story of a soapmaker who saw half his business disappear overnight, and how he dealt with it. We know that failure, by itself, is not fun; it’s the moving-forward process that brings in the learning. 

Speaking of learning, JJ’s entrepreneurial education has taken some unexpected swerves. Sure, she’s a Stanford MBA graduate, but she’s also learned a lot from her family, many of whom started and grew businesses of their own. Her mother was a special inspiration: she capped a long stint of staying home by launching her own successful business with JJ’s brother in her 40s. “I watched, firsthand, how incredibly fun it could be.” JJ has since taken up the mantle, and partnered with her brother on both of her companies. “It seemed natural, when we had this idea, to try it.” Their previous experience dovetailed and diverged in interesting ways: she knows the media and marketing side, and he brings the tech expertise.. She says the fact that they care deeply about each other’s lives—outside and inside the business—”makes it all work for us.”

JJ is now passing on her entrepreneurial spirit to the next generation with her children’s book The Start-Up Club. She likes the idea of familiarizing her kids with the language and ups and downs of the business world. “They can see sometimes things work brilliantly, and sometimes things do not work as you’d planned them to be.” She wants to see them experiment, try new things, and yes, fail, with her same fearless approach. 

Resources

To learn more about our guest, go to https://www.goodpods.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast 

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You may know Lisa from her 2014 stint as Miss Nevada. Lisa’s mother is a former Miss Korea who encouraged her to go the pageant route. Lisa got a late start in the pageant scene, making her debut at 29 (right before she aged out of the competition altogether). As part of her training, she worked with established pageant coach Bill Alverson, who focused less on what she looked like in a bathing suit and more on what she had to say. “By the time I competed, I was done with grad school. I was a business owner by then. I had a different lens and perspective on the title.” Lisa saw her time as Miss Nevada as a way to step up her involvement in the local community. “Why not get further ingratiated?”

After the crown comes the community service: Sutton made nearly 500 appearances as Miss Las Vegas and Miss Nevada. She volunteered in schools, read in hospitals, and made personal connections with people in her community. “It was an incredible experience.” 

Her knack for connecting to others has made her a natural at business partnerships. She took on her first founding role in 2012 with Sin City Cupcakes, a business she launched with a friend while still working as a lawyer. Lisa is a fan of teaming up with her friends. “There’s value in partnering with someone you really know. You know what they’re like when they’re angry when they’ve had a bad day when they’re stressed out. You know what happens.” (And Sutton’s partners know her personality as well!) Her advice for a successful partnership is to “make sure everything is papered up.” But treating business agreements like a living document is also key because as the company grows, your roles will change. 

Lisa is currently on the board of StartUp Nevada, an incubator supporting entrepreneurs in that state. As an angel investor, her advice to female entrepreneurs is simple: ask for the money! “It’s never perfect, but you have to take action.”  She suggests female entrepreneurs give themselves a boost by following successful business leaders like Sarah Blakely (the founder of Spanx), who share resources and encouragement with their followers. “Who are you following? What kind of data and messaging are you consuming as a woman, a female founder and an entrepreneur?” Unfollow the accounts that don’t add value, and chase the ones that give info and encouragement. She also encourages female entrepreneurs to familiarize themselves with their local networks of female angel investors, who are often eager to work with women. But, she says, think carefully about where your business is going: do you have an exit strategy to ensure your investors get paid? 

In the nitty-gritty, she encourages women to focus on metrics when pitching—storytelling is a bonus, but focusing on OKRs gives investors a peek at your gameplan. Taking a business’s goals quarter by quarter communicates a long-term vision in a way that is concrete and accessible to the folks considering a pitch. She says that, compared to male entrepreneurs, women wait longer and are further down the pipeline before they start pitching for investments. “We talk ourselves out of being ready. We have to get out of our own way.” As she puts it: closed mouths don’t get fed. Especially not cupcakes! 
 

Resources

To learn more about our guest, go to https://www.lisasongsutton.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast 

Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!

1. Choose a social media avenue that plays to your strengths, and make sure you enjoy it. Want to blow up on Twitter? “You have to like tweeting! You have to talk a lot.”
2. When the creative juices are flowing, do a brain dump; stash your great ideas for a day when you’re not in the mood to create.
3. Repurpose your content to help your audience absorb it in different ways!
4. 'Mine' other data sources for content ideas: when you search your topic ideas online, make sure you answer those Google auto-fill questions in your video or on the blog. 

When she left college, she joined a salon as a nail tech but has aspirations of becoming an esthetician—a licensed professional who does facials and other skin-care treatments, usually at a spa. “I was good at nails, I liked doing it, and I felt kind of stifled by that.” But her hometown shop was full of estheticians, and they were unwilling to add Nai to their roster. She debated bringing her skills onboard cruise ships before realizing she would likely find work anywhere that was beautiful—Jamaica, Hawaii, Miami, or her new hometown, Los Angeles.

In LA, Nai was “broke,” but she knew the demand was there: she could stand on a busy street corner and see three spas on a single block. As she launched her business, she made a strategic decision to grow her social media presence as well. “I knew I had to reach people who weren’t just right in front of me.” She launched her YouTube channel as soon as she moved to LA. “Being on social media has completely advanced and changed my career trajectory;” she now has almost a half-million subscribers. 

Sometimes entrepreneurs get tripped up on how to translate online impressions to actual sales, but Nai has a knack for it. When she started, Nai would demo her treatments on Twitter and YouTube and encouraged LA locals to book in with her; at the time, 45% of her clients came from that sales funnel. She examined her analytics for out-of-town interest—like the viewers watching from Atlanta and New York—and headed to those cities for pop-up skincare treatments. “Fifteen people made it worth the trip,” especially after she factored in word-of-mouth promotion and local hype. 

It might seem counterintuitive to give away knowledge that she could be charging for, but Nai says it’s actually a sales driver when she does. Maya Elious taught Nai that if she wasn’t able to give away her knowledge for free, “you’re not even knowledgeable enough to be an expert in what it is you’re doing.” Nai estimates that, though she’s shared plenty across various platforms over the last five years, it only represents about 10% of her body of expertise, and her interactions with fans and clients make the trade-off worth it. 

She’s also a master of the thoughtful pivot. When COVID forced her to shutter her spa last summer, her collaborations with brands like Fenty and Target became much more important. She also launched her own line of merch, a spa-inspired line of garments including robes, turbans, and scrunchies. “I’m still talking to the same people.” Her third line of defence against COVID losses was launching a virtual consulting stream. 

Nai sees herself as filling an important gap in esthetics: as a darker-skinned Black woman, she brings knowledge about melanated skin and its unique needs to an industry that doesn’t always cater to them. “When I went to esthetics school, there were very few women of colour who went to the school.” Working with different skin tones and types is a key factor in successful treatments, and Nai says, “I felt like my presence made the other estheticians better.” Through some of her content and partnerships, she’s started filling the gaps in esthetic’s typical service and knowledge. “I’m here to talk to people who weren’t spoken to before.” 

Resources

To learn more about our guest, go to http://labeautyologist.com

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast 

Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!

• Which questions do you need to ask to get your client’s real budget? David uses his knowledge about wedding dress designers and DJs to strategically (and diplomatically) figure out how much his clients are willing to spend.
• Keep your clients in the loop on expenditures! Going over budget isn’t a surprise for David’s clients.
• Compartmentalize your projects. A messy desk can lead to client mix-ups!
• Stay on top of your staff and vendors—since delays can be hard to overcome, David keeps an eye on deadlines and deliverables, and steps in where he needs to: “I know when someone’s not about to meet the goal.”
• When mistakes happen, don’t punish your staff: look for productive, positive solutions that fast-track success.

David Tutera is best known as an event planner for the stars and reality TV show host. His full business is much more diverse, including industry training events, a partnership with Macy’s, a bridal boutique, and more. David’s work focuses on “the art of celebrations. Any celebration should be about joy, and that’s how I make a living.”

David is the grandchild of an Italian immigrant, an entrepreneurial flower shop owner who taught David some of the basics of running a business. At the age of thirteen, David worked the phones at the shop, listening in as his grandfather ran the show. “He was giving me these nuggets of information” about the importance of respecting staff, profitability, and paying attention to details. His grandfather also invited David to watch the floral designers at work, sparking his interest in creative industries. 

After a brief foray into law school, David took an unexpected detour into singing telegrams (!!), where he decided, “If I was going to leave school, I knew I needed to make money.” Dressed in anything from a gorilla suit to a barbershop quartet, he wrote and performed ditties for clients. When the telegram business owner decided to sell, David was first in line with an investment from his grandfather. 

His first event-planning client was a woman who had passed his office window display—very silver lame and ostrich feathers—and asked him to “do” her son’s bar mitzvah. Despite not being 100% sure what a bar mitzvah was, he said sure, a moment he credits as teaching him “the power of yes.”  He slowly transitioned from telegrams to “little parties,” and ultimately found his footing in events. 

While he initially passed when reality TV came calling in the early 2000s, David has now been a media personality for more than 17 years. One twist to the early days of his fame was that his biggest and most lucrative clients didn’t want to deal with David’s busy TV schedule, leading to an unexpected business drought. “I literally thought, did someone cut my phone line?” He eventually started to attract new clients interested in both his fame and his skills. The experience made him very aware that all projects have their own life cycle, and will have the best moment to launch; anticipating those ups and downs will help smooth out turbulence in cash and client flow

It wasn’t always easy and luxurious: he danced with the IRS, couldn’t meet payroll, and grappled with some pretty serious business setbacks. He made a point of protecting the people he worked with, and fixing his mistakes. While it was fifteen years ago, he says “when you go through those large problems, significant amounts of them, you learn quickly what to do.” After those hurdles, he put his support network in place—the folks who can do his taxes while he takes care of the creative side. “You build this puzzle around you. Those people allow anyone in this business to elevate themselves.” By freeing up his administrative tasks, he can focus on keeping his creativity juicy. 

During COVID shutdowns, he started rethinking events and his business. He did a COVID-safe live event in March where the aim was to figure out a future for the events industry, which he sees reviving in full in 2022. “We have to figure out a way to continue our livelihoods.” He also recently discovered that his grandmother was a seamstress, and great-aunt owned a bridal boutique, adding a sense of destiny to his own bridal atelier inspiration. “Sometimes, the things that you do are really laid into the roots of your family.”

Resources

To learn more about our guest, go to https://davidtutera.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast 

Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!
 

But Erica’s passion wasn’t just the news—it was the news in a whole new way. In 2017, she left CBS to launch The NewsWorthy, a daily news podcast that offered a “fair, fast and fun” look at the day’s top stories, all delivered in fifteen minutes or less. When she started, audiences were tuning out the news altogether, saying it was too biased, time-consuming, depressing, and overwhelming. “Those were the four words everyone kept saying,” she says. She decided to solve the problem for people who didn’t want to be left out of the current-events loop altogether, but who needed a different avenue to consume it. 

She knew she was on the right track when the heavy hitters started launching their own podcasts. From the time she conceived the idea to the day she finished her contract with CBS New, Erica watched a number of big players enter the arena with their own news podcasts. After a brief crisis of confidence, she decided to forge ahead. “I realized that the whole point of me starting this was that I brought something new to the table. I offered something unique, which was the vibe of the show.” Her credibility as a journalist allowed her to cultivate a more independent viewpoint on current affairs, allowing folks to trust her unbiased POV and her approachable voice. 

Instead of competition, Erica now sees the bigger producers like NPR as allies. The big shops are an entry point for listeners, who might start with the biggest news shows, but then look around for what else is out there. That’s where The NewsWorthy lives.

After her first year, she looked back and asked two questions: “Did I start to make money? And am I moving in the right direction?” She had made her first dollar, and listeners were reaching out to say they felt more informed and more able to participate in civil life— she even inspired some new voters! 

She’s also expanded her team so she can focus on growing the podcast “as a business,” taking a data-driven approach to advertising, as well as partnering with investors who bring not just money, but also visibility, credibility, and the ability to hire additional staffers. “Some of those resources that I got from the investment, were more important than the funding.” Her focus has switched from delivering daily content to the long-term, broad-scope vision for the show, and it was “so nice” to have time freed up for other parts of her business. 

Lately, Erica’s pregnancy has underscored the need to ensure her business can run without her day-to-day involvement, including hiring a temporary host for the podcast. “It doesn’t have to be me all the time,” she says; it just proves that being a smaller player just means there’s always room to grow. 

Resources

To learn more about our guest, go to https://www.ericamandy.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast 

Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!

 

Resources

To learn more about our guest, go to https://morganharpernichols.com/ 

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast 

Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!

In 2016, she put her frustration into words, shared her personal poem on Pinterest, and then forgot about it. But in a few short weeks, that poem had been repinned over 100,000 times. She had gone viral without really trying to. 

From there, she’s launched herself as a visual artist and poet, been picked up by publishing company Zondervan, amassed more than 1.7 million Instagram followers, done collaborations with Coach, Adobe, Vogue and Aerie, and launched The Storyteller App, where, for $2.99 a month, subscribers receive a daily infusion of her poetry and art. 

She credits her followers for the push that got her where she is today.  Back in 2017, a DM in her inbox requesting an illustrated poem netted her fifty dollars—her first commission—and the sense that this was something she should pursue. 

Coming from the music world, a “gig” often meant shelling out her own money to perform: a flight here, a venue rental there. Of course, Morgan would get paid eventually, but she discovered that poetry doesn’t have that same cash-flow issue. She continued to share online, and her audience grew. That first commission had given her the confidence to believe, “There’s gotta be at least a few other people out there who are willing to support me in this way.”

She was also, for the first time in a long time, able to experiment. She is delicate in saying so, but the Christian music world doesn’t always reward innovation. Channelling her creativity into these new outlets was something she could do from home, and that didn’t cost her money to produce. “I was investing time, but I wasn’t losing thousands of dollars by sharing something on Instagram. If it didn’t work, try something else the next day.” It gave her permission to craft her own voice and the freedom to explore. 

Morgan was also diagnosed with autism in her early 30s. Understanding neurodivergence as a creative working with other brands has been tough but necessary. “I’ve had to ask for a lot of help in areas where I was pushing myself.” (She admits to getting bogged down in admin tasks because she believed that she had to do it on her own.) Her diagnosis forced her to grapple with the parts of her day where she struggled (that inbox, for instance), and pass those over to her business partner and husband so he could support her more effectively. 

While the traditional work world might reward the most neurotypical, entrepreneurs get to create their own work settings and figure out what makes them really thrive. For example, Morgan’s hypersensitivity to colour and stimulation might make grocery shopping a problem, but it makes her artwork richer and more resonant. She then shares that with her collaborative partners and followers. She’s created a work-life that supports her entire life—a way of operating that makes the world more beautiful indeed. 

Resources

To learn more about our guest, go to https://morganharpernichols.com/ 

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast 

Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!

1. Building community isn’t something you check off a list: it requires a commitment and a purpose to keep it going.
2. Communities evolve to reflect their members’ needs: what you start with might not be what you end up with.
3. When you’re scaling an intimate group into thousands of members, insist on a strong code of conduct.
4. Don’t be scared of your communities taking off without you: you wanted a group of people to get together and do something, so let ‘em!
5. Meet your community where they live: for Bureau of Digital, it was Slack. Where is yours?  

The first Bureau of Digital event was a couple of dozen digital shop owners talking about what worked and what didn’t. And, as Carl says, “We fell in love with each other.” Their mission was to provide community to the digital space. 

But from the beginning, it was clear that some folks weren’t in the room. In 2012, there were only a handful of women and BIPOC people at the table, and gender diversity became a bigger issue as the Bureau took off. Carl shares that women often didn’t sign up for owner-focused events, sticking with ones designed for operators. After another gender-unbalanced event, Margaret Lee, who ran Google Maps for nearly a decade, pulled him aside for a chat. She suggested they offer a women’s leadership camp. His response? “Yes, ma’am.” 

It turned out to be a half-solution. At one event, he was approached by a participant who said, “White women’s leadership camp is going great.” When he flinched, she reminded him, “It’s going to be work, Carl.” He knew he had to figure out where to go from there, but he couldn’t do it on his own. 

Enter Project Inkblot. Co-founders Boyuan Gao and Jahan Mantin work with organizations as coaches to build diversity—the real stuff, not trendy hashtags—into their operations. For Carl, it meant taking a step back and asking them to lead the Bureau of Digital through a process of designing Beyond Diversity: an event, a fund, and a mindset that is honest about why BIPOC people and women often feel sidelined in digital communities and is working to change that. “When there are people who can do it correctly because they’ve lived it, I need to get the hell out of the way.”

Bureau of Digital has experienced an explosion of growth since January 202—membership is up a mind-boggling 750%—and while membership hadn’t been a priority before the pandemic, the Bureau’s 500+ members have changed that. They have a robust and active Slack channel full of people sharing frustrations and solutions on topics as diverse as navigating the Paycheck Protection Program to how to hire remotely. Carl regularly mines the Slack channel for topics to write about in the Bureau’s newsletter. 

And while the Bureau may have started in a single room, Carl recognizes that online communities are here to stay. They’re not planning anything in-person until 2022, and “We’re going to have an online equivalent to the in-person events as well.” Score one for accessibility. 

Most of all, Carl wants leaders (especially those without formal leadership training) to rid themselves of the mindset that being in charge means they need to know everything. He says there’s “this fear that someone will find us out,” speaking to the imposter syndrome often found at high levels. But not knowing is part of building the right team and the right culture. “Your job is not to contain a team behind a fence; it’s to create a place that is a magnet,” he says. Creating a diverse, authentic, safe place for leaders to actually get the skills they need to lead the way—now there’s a legacy.

Resources

To learn more about our guest, go to Bureau of Digital

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast 

Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!

1. Bake in your marketing strategies from the earliest days of your business and plan on getting your solution out to your customers.
    
2. Spend time experimenting with marketing techniques, from organic SEO to social media channels, and figure out what works best for you.
    
3. Be honest: are people willing to pay for what you’re doing? Are they coming back for more?
    
4. Be impressive to potential mentors: show them your hustle and how far you’ve come!
    
5. Tune into passive mentorships like YouTube channels and (ahem) podcasts for key insights from your favourite thought leaders. Only take advice from folks who have been where you’re going! 

But going big meant that they were leaving behind the little guys. Peach Tree was past the point of taking on $30 homeowner jobs, but frequent calls from potential clients proved the demand still existed. Taking inspiration from Uber, Lyft, and Airbnb, his app GreenPal was designed to connect customers with lawn care companies who operate on a smaller scale.

GreenPal’s business has doubled every year in the last eight years. His initial value proposition has stayed mostly the same—referring customers to companies—but 300,00 people use the app, and he’s bringing in $20M in revenue each year. By cutting out the legwork of researching company names and reviews, organizing payment, and setting up a lawn care schedule, the app goes way beyond the typical “neighbour kid with a lawnmower” set-up and ties up loose ends for both customers and the companies they work with.  

That’s not to say the early days weren’t tough, but never underestimate how far a little naivete can take you. “If I had known how hard it was going to be, I would have gotten scared and never started,” Clayton laughs about the app’s early days. With two co-founders and no one knowing how to code, they put $150K into the first version of GreenPal, and it was...a failure! The next three years were spent supercharging their tech skills and developing a robust customer service feedback loop that continues to this day. When they relaunched, the grass was indeed greener on the other side. 

It also helped that Clayton’s partners were well-chosen thick-and-thin types, a relationship that he compares to a marriage. One of our listeners, Gabby from Austin, asks about the value of a co-founder, and Clayton recommends careful consideration. “Don’t just go get a co-founder because you think you have to,” he says. Though there is start-up wisdom behind having both the hustler and the hacker on your team, Clayton reminds us that a co-founder partnership may last longer than some marriages (and be messier to dissolve if the day ever comes). 

They keep themselves default alive, so their profits don't outweigh business expenses, and they keep their burn rate low. Taking a practical, sustainable, slow-and-low approach—which he recommends for nearly all small businesses—meant that they could keep going when things get tough. GreenPal also inadvertently tapped into our society's “contactless” needs during a pandemic, a consumer mode that people now use for everything from clothing to groceries.

Clayton credits his personal and business growth with a surprising Super Mario mindset. “Look at your business like a video game,” he says. “You only have to beat level one, throw up the flag, and get through a level at a time.” By focusing on just one or two key things at a time, Clayton says, entrepreneurs can be heroic about setting goals and moving their businesses forward. “I really wanted to make something of myself, and I felt like business was the vehicle for me to do that.” 

Resources

To learn more about our guest, go to: https://www.yourgreenpal.com/

To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to freshbooks.com/podcast 

Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!

In this week’s episode, we talk to Crystal about her experiences as a woman of color in the funding world—Kiira has counts Bumble Fund and Serena Ventures as investors—and her journey through pitch competitions, client acquisition, and how COVID changed (and supercharged) her business: “Our entire corporate strategy is to increase access for underrepresented people.” We also hear from Bumble's Strategy and Social Impact Associate Director Cybil Zhang of Bumble Fund's work funding Black and Latinx female entrepreneurs. 

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

We know you’re awesome—what entrepreneur isn’t?—but do you know how to transform your awesome skills into a viable business? Danny Kerr is the co-founder of Breakthrough Academy, where he teaches tradespeople to scale up their business. They offer lessons on financial management, setting goals, recruiting and managing staff—all the beautiful administrative work you don’t see during a construction project. 

A former “lost university child,” Danny got started as a College Pro franchisee, where he learned the basics of small business ownership, and then worked for the company directly. He eventually oversaw a corps of over 400 painters while still in his 20s. He co-founded Breakthrough Academy in 2015 to help contractors bridge the gap between “grassroots” level entrepreneurship and more enterprise-level business management. We talk to Danny about what makes a business partnership like a marriage, how to balance active and passive marketing strategies, why we shouldn’t be afraid to delegate, and the one skill every entrepreneur should be developing in 2021. Check out Breakthrough Academy’s Business in a Box webinars for ideas for growth and sustainability in the new year. 

Get free BTA resources here: https://trybta.com/imal

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Join us next week for our Season Finale in a special collaboration with Bumble Bizz.

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“There’s no one path to success, and that’s what's really exciting.” If you’ve ever watched a YouTube video from a dedicated content creator and wondered exactly how they got there, you’re not alone. Julie Nolke is one such creator—a theatre school graduate who hustled at her day job and originally used her YouTube channel as a workshop space. She’s committed six years to her channel, doing everything from the acting and writing to the editing and ad selection. Her journey to viral stardom includes a variety of partnerships, plenty of diverse income streams, and a lot of scrappiness. 

On this week’s episode, we talk to Julie about why content creators should focus less on fancy gear set-ups and more on emotional resonance, how she partners with outside brands, and why creator-driven platforms like YouTube can help skirt the traditional gatekeepers in creative industries. Nolke, who was named one of YouTube’s Top Breakout Canadian Creators in 2020, has maintained her distinct POV as the view count ticks up.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs

We talk to Inessa about the surprising ways our values influence our clutter, why home-edit shows are so huge, and how an open window can change the energy of your space. She also walks us through a quick ritual for dual-use spaces—if you’re working in your bedroom or living room, this one’s for you. 

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Guest- Inessa Freya- Website

 “I knew that at some point in my life, I wanted to be part of an organization that advocated for creatives and freelance workers,” says Rafael, and the Freelancers Union does exactly that: they got started by offering insurance to workers outside traditional employment set-ups. They’ve since grown to include a networking hub, a popular blog, a directory of Black Freelancers, and service discounts for members. This week, we talk to Rafael about why COVID-19 hits them especially hard, why freelancing is an unexpected youth movement, and why freelancers definitely have power in numbers. 

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Ruth Elnekave knows what stress is. After all, she’s got five different degrees and diplomas, ranging from an MBA to her chef’s papers. Her business Joya combines her far-ranging professional experience (including business and marketing) with her life-long passions (cooking and holistic nutrition); the end result is wellness-oriented products that bridge the gap between soothing stressed-out customers (hello, paging 2020!) and being totally delicious. 

In this episode, we talk to Ruth about connecting with her grandmother through childhood family feasts, how her personal experience with stress led her to create Joya, and the silver linings of launching a business during a pandemic—turns out it’s pretty good for connecting with customers on social media. We also dive deep into the effects of stress on the body and why food is a “beautiful way to experience other cultures.” 

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Bryan doesn't believe he's put in an honest day's work unless he gets his hands dirty! A natural-born teacher, the Gemini-award winning host has been educating and entertaining viewers across Canada and the US for over seven years on the hit shows House of Bryan, Disaster DIY, and Leave it to Bryan.

Learning valuable tricks of the trade from his father, a meticulous aircraft engineer, Bryan spent his childhood summers building his family's cottage from the ground up. His entrepreneurial spirit emerged at the age of 14 when he opened his own handyman business doing odd jobs for neighbors.

After earning a dual degree in Political Science and Business, Bryan was headed towards a career of practicing law. Realizing he'd rather be renovating than be chained to a desk, his innate passion for building took over and he traded in his tie for a tool belt and founded his contracting company Baeumler Quality Construction. Bryan has now built the 'Baeumler Brand' to include Baeumler Construction, Baeumler Approved, Baeumler Productions, Baeumler Media, and the newly launched Baeumler Family Foundation for Kids. Each and every one of his companies prides itself on professionalism, respect, and quality workmanship. A few years and several hit TV seasons later, Bryan's tackling even more projects than ever - and loving every moment of it!

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Our Guest- Bryan Baeumler

Oh and remember, if you are planning your next getaway, consider visiting Bryan's newest project, Caerula Mar in the Bahamas.  In a world of endless stimulation, Caerula Mar Club is a hideaway; grounded by the island’s rhythm. Visit www.caerulamar.com to make your escape!

Only half of all small businesses use accounting professionals, but they’re now more efficient and affordable than ever before. Today, Twyla talks to us about some of their lesser-known benefits, like helping you craft a powerful 90-day forecast, and finding efficiencies when you feel squeezed. We also talk about why your relationship with your accountant should be great (not just good): you should feel like your business would flop without your accounting professionals.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

“We’re better together, and we go further together.” This is Kalani Hubbard talking about one of the perks of working with his wife Stefanie at their video production company Galaxy Visuals. Together, Kalani and Stefanie have worked on projects ranging from commercials to training videos; their most recent win was developing View and Chew, their own series with Amazon Prime.

On this week's episode, we talk to the Hubbards about how they merge their work-life with their marriage, how Stefanie's former role as a hairstylist still serves her when she's making media and the power of Google Hangouts. We also go high-level: why a big vision doesn't always need a big budget, and how optimism can sometimes mean asking yourself the right questions: how can I make that happen?

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs! 

Guest- Stefanie and Kalani Hubbard

Galaxy Visuals

Fishkin started as a college dropout who went into business with his mom. From these unconventional roots, he's grown into an SEO expert who has kept on top of the shifting trends and best practices. He shares with us how thoughtful market research helps boost small businesses, how un-creepy audience tracking really is, and how a bowl of bolognese helped him bounce back from losing a $13M deal.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs! 
 

GUEST-

Rand Fishkin- Website

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Villaneuva takes a complementary approach to Ash Studio in Dallas, where his work has gradually shifted from corporate gigs to community-based projects. “I look at being an artist in this world as an area that’s full of opportunities.” He's also working towards improved equity and representation in the art world. We talk to Sosa and Villanueva about why their communities are one of their biggest business assets, why cultural representation matters, and how to take a practical approach to admin work and self-care.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Guests-

Farah Sosa- Farah Stop Website

Fred Villanueva - Ash Studios Website

In this week's episode, Mimi tells us about how an unshakeable sadness helped her realize her days in film and TV were behind her, and why she still schedules time for her hobbies—including sewing—despite being immersed in the business of it all day. We also talk about her Puerto Rican family's influence on her entrepreneurship, how she keeps tight relationships in business and life, and how offering a free service helped boost her income. Though her path to success might be full of unexpected loops, Mimi says, “it gave me a view of what I needed to do.”

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Guest- 
Mimi G.- Website

DIY Mask Video-LINK

Sew It Academy- Link
 

Carroll gives us the background on what white supremacy actually is (and why you don't have to be white to perpetuate it), and why companies need to start paying for DEI work in their organizations. We also talk about code-switching, the importance of lived experience, and what makes a good ally. This episode is for all our listeners: we want to unpack the assumptions we make in business and in daily life to help create a more equitable society. As Carroll says, "I am continuing to learn and unlearn, and my discomfort is a good thing."

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

Guest- Antionette D. Carroll- https://www.antionettecarroll.design/ 

In this week's episode, Gibbons gives us behind-the-scenes access to how she landed an on-air hosting gig soon after leaving her day job (hint: it involves a lot of networking!), and how she used that opportunity to get VC funding and launch Clare as a brand. We also talk about the unexpected visibility of being a Black entrepreneur in 2020, how the pandemic enabled online shopping for unexpected products, and why networking and creating relationships really is that important. Clare is now taking aim on an industry dominated by legacy brands with nine-digit valuations, and Gibbons feels prepared. “A lot of time was put in before it was actually successful,” and she's now ready to go global.

Join the conversation on Facebook in our #imakealiving group, where you can chat about challenges, find resources for success, and stay connected with other entrepreneurs!

• Encourage use of pronouns - not just for queer employees but for everyone
• Revise company policies - act in accordance with the law and your values on everything from workplace dress codes to hiring and firing practices 
• Rethink how you categorize your customers. Should you be making gender binary products or would your customers and business benefit from being more fluid.

This isn’t a one and done kind of thing - we’re all learning and growing together and so should our company policies. So keep thinking about diversity and inclusion and how you can be a leader and not a follower in business.

GUEST

Mina Gerges - Website

Guest

Terry O'Reilly- Website

The Apostrophe Podcast Company- Website
 

Thank you to our guests Phylecia an Oona and the 3 entrepreneurs who shared their experiences with us. Find them all below. 

GUESTS-

• Phylecia Jones - https://www.keepupwithmrsjones.com
• Oona Rokyta, CEO and Co-Founder, Lance - https://www.justlance.co/covid19

ENTREPRENEURS

• Julia Kline, Host of Solving Me Too Podcast - https://solvingmetoo.com
• Meegan Czop, Owner of Great Lakes Yard - https://www.greatlakesyard.com
• Ben Yee, Co-Owner of The Camera Department - https://www.thecameradept.com

Guest-

Allis Markham- https://www.preytaxidermy.com/pages/about-prey

Guest- Dr. Sahar Yousef - Website

When Pat Flynn was laid off from his architecture job in 2008, he wasn't sure what to do next. On a hunch, he developed a test-prep course for architects in training; over the next year, his course brought him over $200,000 in revenue. Flynn had seen the power of passive income. Instead of developing more courses, though, Flynn started training others on how to do the same.

"Truly passive income pretty much doesn’t exist," says Flynn, but he knows from experience that designing products that reward you for investing in and building them—and pay out time and time again—comes pretty close. In this week's conversation, we talk to Flynn about his three P's of mapping the market, why entrepreneurs should cultivate their superfans, and how bringing your human side into your business can improve everything from work-life balance to audience relationships. He also takes questions from past #IMakeALiving live-event audiences about interviewing guests on podcasts (and why you should ask “why?”), making the most of your passion-project time in a day-job world, and how to maintain our learning mindset even as we grow into our roles as thought leaders.

Guest- Pat Flynn 

Website- http://smartpassiveincome.com/toolkit

Podcasts

SPI- https://www.smartpassiveincome.com/shows/spi/

Ask Pat- https://www.smartpassiveincome.com/shows/askpat/

Guest- Lisa Canning

Resources:

Stages of Grief- https://psychcentral.com/lib/the-5-stages-of-loss-and-grief/

Guest:

John Kim's Website- Texts from the Angry Therapist

Guest

Elaine Pofeldt- Website

Nagpal, whose background includes both real-life teaching and tech development, was a Forbes’s 2019 30 Under 30 Education honoree. This week, we talk to him about how to keep a relatively sane work-life balance (no all-nighters is a personal rule for him), how to hire and retain great employees (including an unorthodox stable of engineers), and how he’s come to recognize what Teachable really offers its clients. “We always say, No one wants your course,” he explains. “What they want is the outcome. They want the transformation. Your course is a way for them to get there.” He shares some of his knowledge with us, free of charge.

--

Guest

Michael Kass- https://www.storyandspirit.org/michaels-story.html

Guest- Jeni Wren Stottrup

Join Jeni for a free workshop- http://grittybirds.com/freefridays/

We know you like podcasts, but have you ever thought about starting one? On this week's episode, we talk to two women with ample experience in the field. Jeanine Wright is the COO of Simplecast, which helps launch podcasts, and has a special focus on analytics. Fatima Zaidi co-founded Quill, which connects podcasts professionals to folks with a dream in order to get a project off the ground. We get the inside story on what goes into podcasting after the microphone is turned off: podcasts are one of the most powerful marketing tools available to companies, but they also need to find their own path to success. As Zaidi asks, “What kind of brand do you want to be seen as?”

We also talk to Wright and Zaidi about their experiences on opposite ends of the investor spectrum. Zaidi weighs on the value of running a bootstrap operation, while Wright shares her three criteria for considering an investment opportunity. Both also offer insight into their experience as women in a male-dominated sector, where there are opportunities to break new ground and create a work-life balance that works for you.

Guests-

Jeanine Wright- Simplecast

Fatima Zaidi- Quill

Bricia Lopez - Bricia Lopez is an entrepreneur, cultural ambassador, and a key figure in Los Angeles’ gastronomic scene. The New Yorker called Bricia the “Queen of Mezcal.” This year she opened Vegas’s first ever mezcal bar – ‘Mama Rabbit” inside The Park MGM. Launched the Super Mamas Podcast with Paulina, that has become a lifestyle media company, complete with annual events, and corporate partnerships with major brands. Bricia Lopez was appointed by the Mayor of Los Angeles to the Board of Convention and Tourism Development on March 2019. 

Paulina Lopez-Velazquez - CFO and Director of Catering and Special Events. Super Mamas Social, a parenting festival that takes place yearly in Downtown Los Angeles. Paulina currently sits on the Board of Directors of City Charter Schools, a K-12 Los Angeles Based School organization that promotes diversity, culture, and bilingualism. Most recently, Paulina was awarded Women of The Year in the Council District 54, by Assembly Member Ridley-Thomas.

Carmelia Ray is an internationally acclaimed matchmaker for high achieving men and the quality women they’re searching for. She’s also a renowned TV personality from Mom Vs. Matchmaker, The Real Housewives Of Toronto, and A User’s Guide to Cheating Death (Fall 2018).

A frequent media contributor, Carmelia’s advice and expertise have been featured in notable outlets including AskMen, Variety, The Hollywood Reporter, OK! Magazine, Global News, Cupid’s Pulse, The Marilyn Denis Show, CHCH News, Elle, Playback, and countless others. Her wealth of wisdom and experience has also attracted in-demand partnerships with major dating companies including Match.com, Lava Life, Instant Chemistry, and more.

Carmelia is a great example of selling confidently and being bold about getting paid for the value she offers others.

Here’s a summary of what Carmelia taught us today:

• Focus your sales pitch on the value proposition for your clients rather than minutia of the product or service and try not to sound desperate even if you are
• Get organized and plan as much as you can
• Always incorporate time with family and loved ones into your schedule, no matter how busy your business gets
• Network like you would make friends - the more relationships you build, the more robust your sales network
• Collaborate, Collaborate, Collaborate

See what Carmelia is up to at CarmeliaRay.com or on social media @carmeliaray.

Guest

Carmelia Ray- Website

Jewel’s dream is transforming so many realities for new innovators in entrepreneurship, and we can’t wait to see what Google for Startups does under her leadership. 

Here are a few big takeaways from Jewel’s story:

• Don’t wait for people to believe in your idea and fund it - if you build it (and it’s good), they will come.
• Be smart about networking - put your ideas in front of the right people and nurture relationships with them
• Selling your company is not always the fantasy it’s made out to be, map out what your life would be like after you’re acquired and see if that’s what you really want
• Surround yourself with other people who are doing the kind of work you want to be doing and who’ll inspire you to keep going
• Most of all - don’t let your story, the place you live, or the color of your skin, define what’s possible for you

In honor of Black history month, we thank Jewel and the many black entrepreneurs who have paved the way for other innovators to be brilliant and brave.

Guest

Jewel Burks Solomon- https://www.inc.com/magazine/201904/yasmin-gagne/partpic-amazon-jewel-burks-solomon.html

The company was started by Tony Muia, a proud native Brooklynite who always loved showing people around his beloved hometown.

Tony slowly starting doing informal tours for those same folks when they came to visit NYC, driving them around in his car. Soon, their friends and families would visit NYC and ask Tony to do tours for them so he did them as a side hobby while still working his regular job.

In 2004 Tony decided to switch careers after watching NYC tourism increase. However, it mostly focused on Manhattan and Tony felt that Brooklyn had enough amazing foods, neighbourhoods, landmarks and movie locations that it needed its own tour. And that’s when he decided to launch A Slice of Brooklyn Pizza Tour in 2005 with other tours that followed.

What started as a hobby turned into a family business and today he has 3 popular tours that run year round and have proudly introduced over 90,000 people to Brooklyn.

Some people say don’t make your passion your business, but you’re in a business that is inspired by your passion, you have to dive in with both feet.

Tony designed this business around his life, brought in the people who were closest to him and got them invested in his idea, and never looked back.

Here are the key takeaways from Tony’s Story:

• Go to where your audience is - If you want to entice people come to Brooklyn, you might need to pick them up in Manhattan. Which figurative borough are your customers hanging out in right now? Get it? 
• Don’t be afraid to ask questions - your mentors and supporters can help steer you in the right direction.
• Delegate, delegate,  delegate - you don’t need to do it all!
• Leverage press to grow your business
• Make friends with your customers

That’s what’s kept Tony in business for 15 years.

Guest

Tony Muia and Ronnie from A Slice of Brooklyn -https://asliceofbrooklyn.com/

Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'

We sat down with Angie Myung and Ted Vadakan, a husband-and-wife team who have artfully mastered the feat of finding their tribe through their brand Poketo.

The name Poketo (pronounced "poh-keh-toe") stems from the mispronunciation of "pocket" by Angie's grandmother. It tied in perfectly with the first product ever created under Poketo: a series of artist wallets that fit right in your pocket—and Ted and Angie just loved the way it sounded.

Poketo has worked with brands and companies like Nike, MTV, Disney, Target, Nordstrom and MailChimp, museums like MOCA, the Guggenheim, the de Young, and SFMOMA, and has collaborated with over 200 international artists, creating exclusive products that reflect its philosophy of "Art for Your Every day."

Ted and Angie are a great example of two partners who set the tone for their business. Poketo is all about collaboration, community, and partnership - something that is ingrained in their personal lives and amazing love story.

They gave us a lot to keep in mind:

• Find your community and keep them close
• Play to the strengths of your partnership
• Stop worrying so much about your business’ competition and instead, focus your energy on collaboration and staying ahead of the game

Guests

• Ted Vadakan and Angie Myung from Poketo- https://www.poketo.com/

Resources

• Maslow's Hierarchy of Needs- https://www.simplypsychology.org/maslow.html

Courtney Nichols and Gordon Gould- Smarty Pants

Resources:

INC Magazine on hiring a business coach- https://www.inc.com/young-entrepreneur-council/8-convincing-reasons-you-should-hire-a-business-coach.html

In our first Masterclass episode of the season, we are delighted to talk with Peter Shankman. He has been a vocal advocate for neurodiversity in the workplace, he is the founder of the journalism tool HARO, and is a successful writer, speaker, podcast host, and entrepreneur.

In our conversation, we cover a wide ground - not surprising, given that Shankman has leveraged his own ADHD into a better understanding of his complex body chemistry and physical needs. (He tells us how to write a book in 34 hours - it involves booking a flight to Tokyo!) He also answers questions from our #imadealiving live events about why authentic social media is best, why listening to your audience will help grow your business, and why you - yes, you - should charge more in 2020. We take our advice from a man who says that jumping out of a plane gets him into work mode, don't you?

Guest:

Peter Shankman- Website

Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'

Resources

To learn more about Tina and her services go to:
https://tinaessmaker.com

Word of Mouth Marketing- Article
https://www.bigcommerce.com/blog/word-of-mouth-marketing/

Nielsen Report
https://www.nielsen.com/us/en/insights/article/2012/consumer-trust-in-online-social-and-mobile-advertising-grows/

If you like our show, please let us know by rating and reviewing it on whatever platform you listen to it. 5* reviews help us grow our audience and reach!

To learn more about FreshBooks and receive an exclusive offer go to
www.freshbooks.com/imal

As a television producer, Brant Pinvidic has pitched a lot. Like, a lot. In his 15 years in the entertainment industry, Pinvidic has had the chance to get his pitching practice down to a science. In his new book, The 3-Minute Rule, he lays out the basics of what makes a great pitch, and where folks fail. His challenge to readers is to get their pitches down to a crystal-clear three minutes, and on this week's episode, we get the inside scoop on how to nail that process.

"They don’t want to hear any of the fluff and pageantry. They just want to get to the point," Pinvidic says. He gives us some simple ground rules for pitching, including how to avoid too much promotional energy, how to separate opinions from facts, and how to come back from 99 rejections to nail that 100th pitch. His approach has allowed him to become a pitching guru outside the entertainment industry, and he now provides support to a broad range of businesses. "Simple is the new sexy," he says; sounds like three minutes in heaven to us.

Guest: Brant Pinvidic

Book: 3 Min Rule

References:

FreshBooks exclusive offer: www.freshbooks.com/imal

Damona Hoffman: www.damonahoffman.com

Tony Robbins Cold Plunge- https://www.youtube.com/watch?v=_6YtmPo9pxg

Resources:

Transcript- https://www.freshbooks.com/podcast/pitch-your-business-brant-pinvidic

The entrepreneurs that we talk to on this episode have all something in common; their business ideas broke the paradigms of conventionalism and defied the odds of 'success'.

Robert Samuel from Same Ol' Line Dudes found inspiration while waiting in line for a new iPhone; Iris Scott had a dream of being a full-time artist, so she dropped everything and moved to Thailand where she could sell her art online while solely focusing on her craft. Justin Gignac felt challenged by a former colleague on the importance of packaging when selling any product. He took that challenge by literally selling 'nicely packed garbage' to people over 140 countries. We also talk to several NYC street performers, from subway musicians like Leonel Lorador to the very popular street troupes that stop pedestrians in Times Square to a journalist by trade but Batman impersonator by passion.

Throughout this season we have learned that being an entrepreneur is not an easy job, it can be an isolating and life-consuming journey for many, but we also met incredible people that have found a way to make it work. To achieve success, whatever success means to you, you must understand the ins and outs of being self-employed and the very particular sets of challenges that will arise when you are your boss.

We hope that throughout these episodes, we have left something valuable and meaningful to you by sharing the stories of real-life entrepreneurs who have figured out how to balance life and work, be a little more productive or dealt with very particular issues that many of you shared with us as we traveled the country with the live event.

Stay tuned as we gear up for a new season. We will be back soon with more stories, more inspiration, and useful tips from real-life entrepreneurs.

Happy Summer!

Guest Speakers (in order of appearance)

Robert Samuel- Same Ol Line Dudes (also Jeff and Jerry who waiting in line for us, thanks!)

Iris Scott- Finger-Paint Artist

Leonel Lorador- Subway Musician

Batman of the People- Instagram

Joshua Reyes- Times Square Acrobat Troupes

Justin Gignac- Working x Working & The Garbage Project

Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'

Sometimes our past failures haunt us and the fear of our future failures paralyzes us. These obstacles that get in the way of moving forward are in our head. This is the reason why metal health really is an important topic and is actually the bulk of this conversation. You have to acknowledge these obstacles are real in order to begin dismantling them and face your fears. Doing this requires vulnerability which brings this conversation full circle. And, in the words of Brene Brown “Vulnerability is not weakness, and the uncertainty, risk, and emotional exposure we face every day are not optional. Our only choice is a question of engagement. Our willingness to own and engage with our vulnerability determines the depth of our courage and the clarity of our purpose”

Guest Speakers

Sam Rosen- Founder and Entrepreneur

Michelle Horton- Professional Therapist

Center Stage
Trained by Trell - Instagram

“To be featured on Center Stage, send us a voice message!”

Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'

1. Defining the problem
2. Confirming that it actually is a viable problem.

The biggest take away from this whole conversation is to start at the beginning, with the problem—and spend a lot of time there. The last thing you want to do is create a solution that no one wants or is willing to buy into. We also discover that starting a startup is not out of reach.
The steps that Seth gives us are actionable. While it will take a lot of hard work and diligence, you don’t necessarily need a big budget to start. You really just need a group of people who have a problem.

Guests

Seth Radman- Co-Founder at Crescendo | Tech Entrepreneur | Startup Advisor

Center Stage

Charla Ruschelle- CR Clothing Co.

“To be featured on Center Stage, send us a voice message!”

Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'

Zoey Masters- Instagram

Jeremy Bailey- LinkedIn

Center Stage
Christopher Jones- SeeJonesWork

“To be featured on Center Stage, send us a voice message!”

Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'

This season, we've seen that it takes a lot to start a business from the ground up. Not everyone is cut out to be an entrepreneur. It takes a lot of diligence and hard work to get any business off the ground. It's not for the faint of heart. There are a lot of ups, downs, failures, and successes. Sometimes, it's so important to hear what the journey has been like for others, especially, from those who are a little further along on the journey than we are. That's the reason for today's episode. The journey for any entrepreneur can be a complicated one, but, we learn from the growing pains that we encounter. And, hopefully, they make us better business owners.

The growing pains of building your business are real. Determination is one of the main themes that we recognize in Kristen's story. She sacrificed a lot to get the company off the ground— time, money, comfort. But, to her, the business was worth it. And, it's paid off so far. Being your own boss takes determination and grit. Kristen is an excellent example of who will make it in this competitive world of entrepreneurship,someone who is smart and eager to learn. If you're willing to learn, sacrifice, and put in the hard work, then that might be you too. Knowing the road is going to be rough can be discouraging. But, try taking a page from Kristen's book. Let the challenge be what fuels your determination to keep moving forward.

Episode Guests
Kristen Pumphrey- PF Candle CO.

Center Stage
Torin Regier- Keg Shoe

“To be featured on Center Stage, send us a voice message

Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'

So, back to the story of us choosing someone from the IMAL event. We didn’t know how it was going to go but the whole process in finding this one person to feature sounded fascinating and definitely worth recording.

Episode Guests

RM Harrison- our business coach for this episode. RM is a career and business coach based in Austin, TX. She has helped a lot of people "snap out of frustration and burnout and get them fired up again about the work they do." To learn more or get in touch with RM here.

Meesha Farzaneh
Thank you to Meesha for sharing her story with us and being part of this experiment. To find more information about her business go to her website here.

Center Stage
Thanks to Juan Bendana for submitting his story! If you want to learn more about this incredible entrepreneur, visit his website here: https://www.juanbendana.com/. To be featured on center stage, send us a voice message!

Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of 2ndSite.INC dba FreshBooks, its employees or affiliates.

Our featured guests Lisa Canning and Espree Devora share with us their insights, motivations and tips and tricks to accomplish a more balanced work routine so they can have more time for life.

Our Guests Links

Lisa Canning's website and book page:
https://lisacanning.ca/my-book2/

Espree Devora's podcasts:
http://podcast.womenintechshow.com/

http://podcast.wearelatech.com/

**Resources: **

Work-Life Balance research studies
https://www.ustravel.org/research/state-american-vacation-2018

https://www.ted.com/topics/work-life+balance

https://www.forbes.com/sites/forbestechcouncil/2018/01/25/entrepreneurs-need-to-pay-more-attention-to-work-life-balance-heres-how/#47780ded46b3

https://www.entrepreneur.com/article/311414

https://www.tci-thaijo.org/index.php/IJBS/article/view/521/pdf

http://businessresearcher.sagepub.com/sbr-1863-102641-2779724/20170508/short-article-more-companies-offering-unlimited-time-off

Episode 05“It’s all about the money....and taxes.”

Today’s episode is about one of the most dreaded yet necessary pains every entrepreneur has to endure...tax season. No matter how big or small your business is, taxes are always going to be somewhat complicated, confusing and could create a lot of troubles if not dealt with appropriately. We are here to help!

Our featured guest, Paco de Leon is a self-proclaimed ‘money nerd,’ she founded “The Hell Yeah Group” to help small creative entrepreneurs better manage their finances. Paco shares valuable advice and tips on how to organize your finances, so you are always in control of them and not them in control of you.

As we were developing this episode, we realized that Darbi was not exempt from the familiar “wait till the very last minute” attitude that a lot of freelancers or new business owners have when it comes to taxes, so we decided to document her journey into filing taxes as an entrepreneur. For that, we invited Chicago based accountant Yolanda O’Neal, to sit down and help Darbi figure out her tax situation for 2018.

As you will hear from both Paco and Yolanda, taxes are indeed complicated, the tax code is confusing and its always changing but they both agree that it is not your job to keep up with it, that is what your accountant is for. Accountants are a vital role in every small business owner and a solid piece of advice...find a good one!

Your job is to stay on top of your daily transactions, your bookkeeping, your invoices, expenses, and other day-to-day operations. Doing that in an organized and consistent form will alleviate a lot of the pain and paperwork when tax season arrives.

We genuinely hope this episode is helpful and you find some tips on how to better manage your finances so that future tax seasons are as painless as possible. 

Happy Tax Season!

Guests Paco de Leon- The Hell Yeah GroupYolanda O’Neal- O’Neal Consulting 

Episode 04 "Being a Female Entrepreneur PT. 2"

Welcome to the second episode of our 2-part series in honor of “Women’s History Month.” On this episode, we explore the role of equity in the female entrepreneurial world. We hear from 2 female business owners who share their experiences and journies to success.

Equality. This is the conversation we’re having during women’s history month. However, to give this topic justice, we need also to consider what part equity plays. Equity is the varying levels of support need to obtain true equality for people from different backgrounds.

Based on how you self-identify, the amount of equity needed to accomplish equality may vary. In our last episode, we covered a pretty broad view of what it’s like to be a woman in the entrepreneurial world. However, what we didn’t include is how the experience can vary from person to person.  

Join us as we listen to the stories behind two successful female business founders: Kweighbaye Kotee and Laura Laban. They share their experiences honestly and openly, and the role their particular intersections had on their path to becoming successful entrepreneurs. 

To close off this series, we are excited to include award-winning poet, writer, and activist Staceyann Chin’s, "Equality Now"; a spoken word piece she wrote for the National Equality March in 2009.

Episode Guests

Kweighbaye Kotee- Founder and CEO of the Bushwick Film Festivalhttps://www.bushwickfilmfestival.com

Laura Laban- Co-Founder and CEO of Infinite Flight LLChttps://infiniteflight.com/

Citations and Resources

Kimberle Crenshaw’s TED Talk on Intersectionality

https://www.youtube.com/watch?v=akOe5-UsQ2o

Equality and Equity- Context and Differencehttps://www.ywcalgary.ca/news/equity-v-s-equality-whats-difference/

https://www.forbes.com/sites/ellevate/2017/09/14/why-we-need-gender-equity-now/#74eff0577a24

Disclaimer

The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'

Episode 03- "Being a Female Entrepreneur PT1"

Welcome to a special 2-part series in honour of Women's History Month. We take a look at the entrepreneurship world from a female perspective.

Being a woman in the small business world isn’t easy. Even if you don’t self-identify as a woman, because of recent media movements, you can probably gather that it’s not exactly a walk in the park for females. There’s been a shift, on a large scale, in society recently. The #metoo and #timesup movements have brought some incredible awareness to the issues of inequality through mass media. It’s no longer taboo to discuss experiences. There is a power behind the voices that speak up. But, these developments are relatively new when you think about it. 

How is the gender gap being addressed and how can women learn to negotiate equal pay in the freelancing world. We also look at the role of men in the fight for a more equalitarian and inclusive society.

**Episode Guests**

Rubina Shaikh

Thanks to Rubina Shaikh for sharing her experience as a female entrepreneur and freelancer. To learn more about Rubina go to https://www.linkedin.com/in/rubinashaikh/ 

Kathlyn Hart

Thanks to Kathlyn for a genuinely insightful conversation on how women can build confidence and negotiate equal pay in the freelancing and entrepreneurship world. To hear more about Kathlyn, her coaching services and all the fantastic work she does, check out her Podcast: "The Kathlyn Hart Show."

http://www.kathlynhart.com/podcast/ 

Rachel Wynn

Thank you to Rachel for her insights on feminism and the role of men in the fight for equality. Rachel is a "self-proclaimed feminist" who leads The Feminist Founder group. To learn more and join the ongoing conversations go to https://www.feministfounder.com/

Rachel is also the CEO of Starlight Social. If you need Social Media management for your site or business, go to https://www.starlightsocial.com/ 

** Episode Citations**

Here are the links to some of the citations we had and resources on feminism, gender gap and women's rights.

1) CBS and Refinery 29 poll on feminism amongst Millenials https://www.refinery29.com/en-us/midterm-election-women-dont-identify-as-feminists

2) the #metoo Movement

https://en.wikipedia.org/wiki/Me_Too_movement

3) Time'sUp Movement

https://en.wikipedia.org/wiki/Time%27s_Up_(movement) 

4) https://www.telegraph.co.uk/women/life/1918-vs-2018-13-things-women-couldnt-do-100-years-ago/

5) https://www.huffingtonpost.ca/entry/rights-women-have-gained-since-earning-the-right-to-vote_us_57e9ed33e4b0c2407cd93434

6) https://www.freshbooks.com/press/data-research/women-in-the-workforce-2018 

Center Stage

Thanks to Martha McCallum for submitting her story! If you want to learn more about this incredible entrepreneur go to https://marthashelihikes.com/ 

If you want to apply to be featured on Center Stage go to www.freshbooks.com/podcast 

Disclaimer

The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of 2ndSite.INC dba FreshBooks, its employees or affiliates.

We also talk to 3 different entrepreneurs who work from different places: home, coffee shops and co-working spaces. What is the difference? What are the pros and cons of each of them? Join us as we take a deep look at how the space surrounding you can help you become a more productive individual.

** Center Stage**

Thank you Michael Der for sharing your center stage story. To find more about Michael go to, https://www.michaelderphotography.com/]( https://www.michaelderphotography.com/) To be featured on center stage go to: [www.freshbooks.com/podcast](www.freshbooks.com/podcast)

Episode 2—Citations

1. What & What Not to Avoid. #7 Productivity Hacks for Entrepreneurs href="https://www.entrepreneur.com/article/323404">https://www.entrepreneur.com/article/323404</p> <p>

2. 8 Essential Productivity Tips for the Busy Entrepreneur

   https://www.inc.com/john-discala/8-essential-productivity-tips-for-busy-entrepreneur.html

3. Is Noise Always Bad? Exploring the Effects of Ambient Noise on Creative Cognition

   https://www.jstor.org/stable/10.1086/665048?seq=1#metadata_info_tab_contents

4. It has been my observation that most people get ahead during the time that others waste. -Henry Ford

   brainyquote.com

5. Entrepreneurs work over 60+ hours a week (infographic)

   https://www.entrepreneur.com/article/285079

    

Our next episode will be a very special episode in honor of International Women's Day! Make sure to subscribe to get the latest episodes as soon as they become available.

Episode 01- Present and Future of Entrepreneurship

Why are people turning to self-employment in the current economy?

Alex, a freelancer who thought jumping ship and starting her journey would be a lot simpler than it turned out to be. A whole new set of challenges arise once someone decides to venture into entrepreneurship and a lot of times, those challenges are not-so-common knowledge.

We talk to some FreshBooks folks who share some interesting numbers and data on the present and future of entrepreneurship.

All these experiences, insights and pain points collectively motivated us to create this podcast, and they set the tone to all the incredible conversations we are about to share with you.

Welcome to #imakealiving!

Thanks to Alex Rathbun for sharing her experiences in such an honest and vulnerable form. For more on her go to https://www.brightlyalex.com/ 

Thanks to Carly Moulton and Dave Crosgrave from FreshBooks for sharing their data and reports insights with us. To find more about the Annual Reports FreshBooks publishes on self-employment go to https://www.freshbooks.com/press/data-research 

Center Stage Each episode, we will devout the last few minutes to highlight entrepreneurs and freelancers from our audience who are doing great and/or unique things out there. 

For our inaugural Center Stage, meet voice-over actress Debbie Irwin AKA "The voice of the Statue of Liberty" amongst others.

To learn more about Debbie go to: https://www.debbieirwin.com/