DiscoverI Make a Living
I Make a Living

I Make a Living

Author: 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’re nerding out with Thursday Nerdisodes: Not your typical business podcast episode. These mini-episodes focus on the technical aspects of running a business. Listen in for tactical strategies, tips and insights that you can action right away into your own business venture.

81 Episodes
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 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!
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-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.”
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 business practices. He’s 22, and he’s been in business for half his life. 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.”
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 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.
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 double-duty as a construction company project manager and an actor in San Francisco before taking the leap and moving to Hollywood in 1999. 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!
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.Raise Your Frequency- Snap out of your negative cycles by doing something creative!Identify Your 'Little Wins'- Do not overlook your small achievements, they are an important part of the journey, so CELEBRATE them! 
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 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.”ResourcesTo learn more about our guest, go to learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!
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 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?
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 was a foundational step in the lifelong process of becoming a fashion mogul. Now, in 2021, Rebecca Minkoff has flagship stores in LA, Hong Kong and New York City, among others; she’s also distributed by more than 900 companies worldwide. 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.ResourcesTo learn more about our guest, go to learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!
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 thirty minutes to come up with a plan, they decided to go for it. Aira was launched in 2015. 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.”ResourcesTo learn more about our guest, go to learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!
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 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. ResourcesTo learn more about our guest, go to learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!
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 history doesn’t show a lot of commitment to a role, company, or profession, investors might be less interested in committing to you.  Market research and proof of concept mean you’re coming in with knowledge and fans! Show your investors you’re armed with knowledge and customers.
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 and take on new projects. “I’m big on legacy building,” she says.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!  ResourcesTo learn more about our guest, go to learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!
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 help your audience absorb it in different ways!'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. 
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 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.” ResourcesTo learn more about our guest, go to http://labeautyologist.comTo learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!
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 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.  
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 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 flowIt 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.”ResourcesTo learn more about our guest, go to learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available! 
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 successively larger markets, finally landing at CBS News in Los Angeles. She was there for three years, working on-air in the second-largest TV news market in the country. 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. ResourcesTo learn more about our guest, go to learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available! 
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 laundry).  Listen to yourself! Literally, that is: Morgan uses Otter to verbalize her ideas and to keyword her ideas for easy tracking. Write about what makes you angry! That will help you get to the heart of what you care about. Start making a change there.ResourcesTo learn more about our guest, go to To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available!
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 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. ResourcesTo learn more about our guest, go to To learn more about FreshBooks and take advantage of an offer exclusive to our podcast listeners, go to Follow us on social @freshbooks, and remember to subscribe to get the latest episodes as soon as they become available! 
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