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 wallflower, if I’m honest”—she’s grown into herself as a business owner and service expert. Alli spent her 20s in New York City, doing PR and styling...
Aug 23, 2021•28 min•Season 4Ep. 17
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 packaging. 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-fo...
Aug 16, 2021•29 min•Season 4Ep. 16
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 consultancies with companies like GSK and IHG. In 2015, he was named to The Time’s Superteens list, and since then, he’s only gotten more polished in his busi...
Aug 09, 2021•23 min•Season 4Ep. 15
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-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 f...
Aug 03, 2021•28 min•Season 4Ep. 14
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 path then became a bit wilder than your average home renovator. “If you get a national commercial, you’re at least buying a car,” he laughs. Josh did...
Jul 26, 2021•29 min•Season 4Ep. 13
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, life and the space that surrounds you. All of these elements directly impact your mood and your confidence when dealing with negative feelings. Rais...
Jul 23, 2021•6 min
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 promote their respective branding agency and web design shop in the meantime, well then, hey: that’s a bonus! But a few months in and they were already g...
Jul 19, 2021•32 min•Season 4Ep. 12
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 project was a whopping two pizza pies. “There have been stinkers like that over time, but with the stinkers, you learn a lot,” he laughs. Of course, you...
Jul 12, 2021•24 min•Season 4Ep. 11
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 Bridgerton ), Rebecca designed a square-necked, Empire-waist number that checked her boxes (and her parents made sure it stayed PG-13). For Rebecca, this wa...
Jul 05, 2021•25 min•Season 4Ep. 10
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 everything from work culture to clients. “It felt like a good idea at the time to talk about starting a business together,” he says, and after taking th...
Jun 28, 2021•20 min•Season 4Ep. 9
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 podcasts,” she explains, channelling the energy of the popular book recommendation site. Before launching GoodPods, JJ—who was already a podcaster herse...
Jun 21, 2021•23 min•Season 4Ep. 8
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 to your kids to selling in five years, make sure every co-founder is working towards the same long-term goals. Stability is attractive. If your work ...
Jun 17, 2021•5 min
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 and accessories e-commerce store , and we are wowed. Her goal is to build up lifestyle businesses to eventually graduate from running the day-to-day ...
Jun 14, 2021•25 min•Season 4Ep. 7
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 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. Repurpose your content to hel...
Jun 10, 2021•4 min
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 barber, a few pals who did hair, and a league of friends acting as low-key brand ambassadors across campus. When she left college, she joined a salon as a ...
Jun 07, 2021•25 min•Season 4Ep. 6
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 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 surpri...
Jun 03, 2021•5 min
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 event planner for the stars and reality TV show host. His full business is much more diverse, including industry training events, a partnership with Ma...
May 31, 2021•30 min•Season 4Ep. 5
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 be on TV,” she laughs, comparing her small-town news experience to “grad school” for TV journalists. Over the next seven years, she worked in successiv...
May 24, 2021•29 min•Season 4Ep. 4
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 authentic record of what you’re thinking about, and sharing that with your community helps folks recognize themselves in you (and your four loads of laund...
May 20, 2021•8 min
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, she laughs, with an English degree, “there aren’t a ton of Indeed posts out there.” In 2016, she put her frustration into words , shared her personal ...
May 17, 2021•36 min•Season 4Ep. 3
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 you start with might not be what you end up with. When you’re scaling an intimate group into thousands of members, insist on a strong code of conduct....
May 13, 2021•6 min
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 leader, you probably didn’t go to school for that,” he says and gave himself the goal of figuring out how to help people in leadership roles unlock their...
May 10, 2021•27 min•Season 4Ep. 2
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 media channels, and figure out what works best for you. Be honest: are people willing to pay for what you’re doing? Are they coming back for more? Be...
May 06, 2021•6 min
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 than $10M annually. But going big meant that they were leaving behind the little guys. Peach Tree was past the point of taking on $30 homeowner jobs,...
May 03, 2021•32 min•Season 4Ep. 1
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 telemedicine took another leap forward, Kiira and Crystal were on the cutting edge. In this week’s episode, we talk to Crystal about her experiences as a woman...
Dec 21, 2020•28 min•Season 3Ep. 15
Get free BTA resources here: https://trybta.com/imal 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,” Dan...
Dec 14, 2020•30 min•Season 3Ep. 14
Guest- Julie Nolke “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 ...
Dec 07, 2020•32 min•Season 3Ep. 13
“Is your space feeding you? Or is it getting in the way?” These are the kinds of questions Inessa Freya asks her clients. As both a psychotherapist and a feng shui expert, Inessa taps into her knowledge of how our spaces affect our mood and vice versa. In a year when we’re all spending more time than ever in our house, creating nourishing and fulfilling work-from-home environments are an investment in business success and good mental health. We talk to Inessa about the surprising ways our values...
Nov 30, 2020•29 min•Season 3Ep. 12
Rafael Espinal knows freelancing. His parents both moonlighted—as a photographer and a baker—and as part of the New York City Council, he helped pass the “Freelance Isn’t Free Act,” which allows NYC-based freelancers to tap into city support in resolving delinquent client payments. He’s also the youngest person to be elected to the New York State Assembly, and a former teacher. Now, as Executive Director of the Freelancers Union , he spends his days helping freelancers get organized, big picture...
Nov 23, 2020•28 min•Season 3Ep. 11
Join #IMakeALiving alum Elaine Pofeldt for our next webinar “ Building A High-Revenue One-Person Business In Challenging Times ” on November 19! Elaine and her four expert guests will walk us through fail-proofing your business and scaling revenue. The first 100 attendees will receive a free copy of Elaine’s book “The Million-Dollar, One-Person Business.” Sign up today ! Ruth Elnekave knows what stress is. After all, she’s got five different degrees and diplomas, ranging from an MBA to her chef’...
Nov 16, 2020•27 min•Season 3Ep. 10
