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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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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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In this week’s episode, we talked to Carl Smith from Bureau of Digital. In our I Make a Living Nerdisode, he gives us his top tips for building organic and authentic communities. Building community isn’t something you check off a list: it requires a commitment and a purpose to keep it going. Communities evolve to reflect their members’ needs: what …
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When Carl Smith’s eleven-year-old daughter started getting into classic rock like Joan Jett, she asked her dad how he wanted to be remembered. Carl had run his own digital agency nGen Works for twelve years, but his daughter’s questions about legacy made him realize his true passion was boosting other leaders into the stratosphere. “If you’re a lea…
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Bryan Clayton, CEO and Founder of GreenPal and small-business mentor, gives his five best ideas for entrepreneurs and small-business owners: Bake in your marketing strategies from the earliest days of your business and plan on getting your solution out to your customers. Spend time experimenting with marketing techniques, from organic SEO to social…
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In 1998, Bryan Clayton was one more 18 year old with a lawnmower, keeping his neighbour’s outdoor spaces nice and tidy. His marketing strategy wasn’t much more than a photocopied flyer. But over the next 15 years, his landscaping business—by then called Peach Tree—took on major corporate clients and grew to employ over 150 people and bring in more …
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For anyone who’s ever Googled a symptom, this episode goes out to you. Crystal Evuleocha, founder and CEO of Kiira, is a kindred spirit, but her self-diagnoses landed her in surgery after she didn’t know when to get help. Her experience led her to develop an app that connects college-age women with doctors they can trust. In a year where telemedici…
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