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The brightest entrepreneurial minds discuss all that it takes – the grit, the money, the obstacles, the passion, and the humor – to build a company from launch to exit. Join in with hosts and renowned leaders, Erin Patinkin (CEO & Founder of Ovenly) and Natasha Case (CEO & Founder of Coolhaus) every Thursday for fascinating conversations about the journey to succeed in business. Produced by Eater and the Vox Media Podcast Network.
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I Make a Living

FreshBooks, Damona Hoffman, Francisco Arizmendi

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What does making a living mean to you? Every entrepreneur answers this question differently, and we want to hear them all. On this show, our host Damona Hoffman talks to today’s most successful entrepreneurs about what it means to carve your own path, define success on your own terms, and build a business that brings you satisfaction. We’re interested in every aspect of being your own boss: The upsides, the downsides, and everything in between. This season, on top of full-length episodes, we ...
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Kate and Scott debrief the whole first season, through the lens of doing something for the first time in your business — in this case, a podcast! Producing our first season of Less Than Likely together brought a lot of lessons, discomfort, new experiences, surprises, and above all, amazing conversations. We dive into what it feels like to commit to…
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Our first Less Than Likely "expert episode" features Sybil Grieb, digital marketing expert, Founder of 100 Hats, and SVP of Brand Partnerships at Whalar. It was so fun hearing Sybil’s less than likely story of starting her own agency and then pivoting to where she is most excited to grow her expertise. We get into the nitty gritty of all things soc…
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Natasha Case and Freya Estreller had just started dating when they founded Coolhaus, a truly delicious ice cream company that quickly became a favorite brand of this generation. They walk us through their many times over less-than-likely story and how they’ve navigated building their business, starting a family, creating another business - Future G…
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Eva Woolridge is an award-winning Queer, Black & Chinese portrait photographer, public speaker, and social activist based in Brooklyn, NY. In this conversation, we hear about her artistic process and how she navigates the integration of artistry and entrepreneurship, and how her career has shifted as her work becomes more visible. Eva offers her pe…
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Kerstin Martin, Squarespace Educator and Creator of the Calm Business Movement calls herself an accidental entrepreneur. Her experimental nature and commitment to anti-hustle has helped her to build a business she loves to run and grow, providing online courses and community for thousands of solo business owners and their own growing businesses. We…
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Susie Sarich, Founder and CEO of SusieCakes, created a whole new industry before there were any multi-unit from-scratch bakeries in the US. She shares the many challenges she went through to bring dozens of stores to California and Texas (and expanding) over the past 20 years, including the naysayers along the way who questioned the viability of he…
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Saving the planet was the furthest thing from Deanna Taylor-Heacock’s mind when she got the idea to open Good Bottle Refill Shop, the first refill shop in New Jersey. What started out as a way to save time and money as a mom became a zero waste mission and business model to meet it. In a society where convenience is king, Deanna talks about how she…
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Erin Loos Cutraro is the Founder of She Should Run, a non-partisan nonprofit organization working to dramatically increase the number of women running for office, promoting leadership and encouraging women from all walks of life to run for public office. While women are elected at the same rate as men - when they run for office - they are less like…
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It’s fitting that our first guest is our good friend and mentor, Sas Petherick, Founder of the Self-Belief School and Self-Belief Coaching Academy, from which both Kate and Scott are certified. Sas is radically changing the course of the coaching industry and humanity’s relationships with self-doubt through evidence-based tools and techniques that …
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Welcome to Less than Likely, a podcast about the honest, behind-the-scenes stories of real entrepreneurs and their less than likely journeys of creating successful businesses. Hosts Kate Jaeger-Thomas and Scott Robson tell their own entrepreneurial stories in this episode, what makes them and their business “less than likely” and reveal some of the…
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Alli Webb was always interested in beauty, starting from her roots as a curly-haired kid growing up in South Florida. She says that going to beauty school was “one of the best decisions I ever made,” and Drybar, her ultra-popular chain of hairstyling studios, definitely proves her point. While she says she spent her childhood as a people-pleaser—”a…
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If your memories of ice cream are mostly from childhood, Natasha Case would like a word. Her company, Coolhaus, is bringing sweet icy desserts into the millennial mindset: she launched at Coachella back in 2009, and Coolhaus’s 2021 lineup includes mouth-watering flavours like cereal milk, cannoli, and churros, all delivered in cute illustrated pack…
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Chances are that your entrepreneurial idols were born after the turn of the millennium, but Ben Towers is here to change that. He’s been working since before his twelfth birthday, getting his start on web design projects for friends and family before launching into the stratosphere: we’re talking British Royal Family, angel investment, and consulta…
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Trigger Warning: this episode discusses postpartum depression and briefly mentions suicidal thoughts. 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…
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Most contractors get their big break with a high-profile job or a great referral. For Josh Temple, his breakthrough moment was going national on Mazda’s first-ever “Zoom-Zoom” commercial. Josh was a contractor by day, but when a receptionist at his first construction company told him he should try out sketch comedy, he fell in love with improv. His…
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Make Rejection Fun- Turn the icky feelings into a game and change your mindset about the negative approach to them. Get Comfortable with Yourself - Define what confidence means to you, identify your personal values and live them daily! Check Your Vibes- What relationships are you surrounding yourself with, what decisions are you making about work, …
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Emily Thompson’s experience starting the Being Boss podcast in 2015 is a strong argument for why you should always plan for success. She and her “business bestie” Kathleen Shannon started the podcast as a way of taking the conversations they were having about their businesses and being entrepreneurs into the public realm—and if they happened to pro…
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If your business ideas have ever been more of an airball than a total slam dunk, take heart: you are not alone. Sanjay Parekh is known for being ahead of the game as an entrepreneur, but even he’s had off-days. Take Pizza Impulse, his idea for pizza delivery that relied on random demand, random supply, and push messaging. His sales total on that pr…
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For Jewish girls, the bat mitzvah is a pivotal moment of becoming a young adult and joining the adult community. For Rebecca Minkoff, who had been designing and sewing clothes since she was eight years old, the celebration was also a chance to showcase her fashion skills—and her “newly budding rack.” Pulling inspiration from the 1700s (think Bridge…
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Most people go to Las Vegas hoping to shrug off the demands of work, but for Paddy Moogan, a trip with mates turned into a life-changing business opportunity. On a trip to Sin City, his friend approached him with a proposal: why not take Paddy’s expertise in digital marketing and launch their own agency, a shop where they could call the shots on ev…
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If you’ve ever started your exercise time by standing there for 20 minutes choosing a podcast, know that you are not alone. You are in the company of JJ Ramberg, who launched GoodPods to help curb that endless search for great podcasts by tapping into what your friends and favourite influencers are already listening to. “It’s like Goodreads for pod…
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Everyone’s story matters! Lisa wants to know everything about the people pitching to her, from their business background to how many pets they have. And if you’re not the one running the day-to-day business, make sure to bring that person into your pitch strategy: she wants to meet them too. Where do you want to end up? From passing on the business…
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Lisa Song Sutton describes herself as a “serial entrepreneur,” and her portfolio is proof. From Sin City Cupcakes—a boozy bakery she co-founded in 2012—to Ship Las Vegas, her mailbox and shipping stores across the city, Lisa’s portfolio is a truly diverse set of business assets. Add in her real estate sales team, not to mention a women’s swimwear a…
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On this week’s Nerdisode, Nayamka Roberts Smith, aka Nai, the labeautyologist, gives us her tried-and-true methods for building an authentic and engaged social media audience. 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.” When t…
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Nai Roberts-Smith might be the mega-popular skincare expert labeautyologist these days, but like many entrepreneurs, she started in a dorm room. She was an amateur nail technician, complete with a wall of polish colours, and she would do nails for less than the price of lunch. “I had a group of friends who all did beauty services,” she says a barbe…
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Earlier this week, mega-event planner and reality TV host David Tutera talked to us about his path to success; in our Nerdisode, he gives us the nitty-gritty on keeping his clients and team happy. 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…
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We know that certain industries thrived during COVID—home renovations and online shopping, anyone?—but there’s no denying that some sectors took a major hit. We got a call from Eve, an event planner wondering how she can move forward post-pandemic. Well, we brought in the capital-E expert to answer Eve’s question. David Tutera is best known as an e…
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If you think television journalism is glamorous, Erica Mandy is here to set you straight. She started as a “one-woman band” in a small TV news market, where reporting on location often meant that she was the photographer, camera operator, writer, editor...all while also being the on-air journalist. “That weeds out the people who are in it just to b…
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Mine your own life for inspiration! We bet you have at least a few photos on your phone that can prompt you to dig deeper into your own experiences. What’s in your notes? Check your written records on WordCounter to reveal which ideas you keep coming back to. (Morgan checks her phone’s notes app monthly!) Write your to-do list by hand. It’s an auth…
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Morgan Harper Nichols might be the rarest bird in the entrepreneurial aviary: she was actually looking for a nine-to-five job when she started as an internet sensation. After a half-decade on the contemporary Christian music scene, she was tired of hustling. “It’s a hard industry to be in,” she says. She was looking for something more stable, but, …
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