Business Advice: I Asked 100+ Founders of $1M-$1B Businesses
What does it take to start and grow a business to $1 million? Or even $1 billion?
If you’re among the more than six in 10 (62%) of U.S. adults who want to be their own boss, you might be familiar with the basics of entrepreneurship. Still, the prospect of leaving a secure 9-5 job to go all-in on a side hustle or business can be daunting.
Hearing from founders who have already traveled the path to business success — and learning from their mistakes made and wins achieved along the way — can help prepare you for your own entrepreneurial journey.
Related: I Wish I Received This Advice as a Young Entrepreneur
Over the past four years, I’ve interviewed more than 100 successful entrepreneurs who started businesses worth $1 million to $1 billion or more.
I’ve sat down with business luminaries like Richard Branson (Virgin Group), Martha Stewart (Martha Stewart Living Omnimedia), Alexis Ohanian (Reddit), John Mackey (Whole Foods Market) and Bobbi Brown (Bobbi Brown Cosmetics, Jones Road Beauty), among so many others.
No matter how well-known the founders or their particular industries, they, like all entrepreneurs, had to push through business ups and downs to reach success on the other side.
Related: 7 Critical Pieces of Business Advice for Entrepreneurs Just Getting Started
Needless to say, their entrepreneurial careers have taught them a lot, and even if you take just one lesson from their experiences, you could be one step closer to achieving your own business goals.
Read on to see some of their best advice.
Be curious and open-minded
Martha Stewart – Martha Stewart Living Omnimedia
Stewart stresses the value of curiosity — and explains how she uses it to expand her horizons every day.
“Curiosity is certainly a character trait that I think is very important if you’re trying to understand, ‘Where is the world going? What the hell are we doing here? What are we going to do?'” Stewart says. “So I’ve always been happy to be curious. I read a lot. I travel a lot. And one of the things I try very hard to do is never drive down the same street twice if there’s an alternative so that I might see something that I’ve never seen before. And when I travel, I try to do the same thing. I try to see as much as I can in a day.”
Melissa Ben-Ishay – Baked By Melissa
Ben-Ishay isn’t afraid to admit when she doesn’t have all the answers.
“I love to be wrong,” Ben-Ishay says. “I don’t think I know everything. In fact, the older I get and the more experience I have under my belt, the less I know. And that is something I know with certainty. And I think that is an incredibly important mindset for a leader and an entrepreneur.”
Related: 3 Ways to Foster a Culture of Curiosity (and Why You Should)
Arsha Jones – Capital City Mambo Sauce
Jones didn’t grow up in a family of entrepreneurs and says she was on her own when it came to figuring out how to grow her small, home-based business. Without outside money to fund her venture or an extensive network to tap into, she took a grassroots approach instead.
Jones scanned grocery shelves for small bottled brands, “like a local barbecue sauce,” and then sent their owners an email: “I would say, ‘How did you do X? And how did you get on the store shelf?'” Jones explains. “And they would just sit down and answer any kind of questions that I had. And that was really how I jumped over a few of those hurdles, at least in the beginning.”
Image Credit: Courtesy of Capital City Mambo Sauce. Arsha Jones.
Get clear on what you want and stay true to it
John Mackey – Whole Foods Market, Love.Life
Mackey suggests entrepreneurs first figure out if they want to be startup serial entrepreneurs or builder entrepreneurs. “If you’re the serial entrepreneur, then my advice is figure out when is a good time to sell so you can go on to your next thing,” he says.
Mackey’s advice for builder entrepreneurs concerns the critical issue of venture capital. He says most venture capitalists and those in private equity will automatically assume you’re a serial entrepreneur, and “they’ll be looking to replace you.”
“If you are going to be a builder, you should be very clear with the investors that you bring in that you’re not looking to sell the business: You’re looking to build it — you hope to grow it for many years, and the exit for them will not be a sale. It’ll be an IPO,” Mackey says.
Tom Baker – Mr Black Cold Brew Coffee Liqueur
Baker says it’s important to consider your business’s unique offering, even if it slows you down temporarily.
“[I wish we’d] spent a little more time upfront thinking about how we were actually going to recruit drinkers into our brand,” Baker explains. “What will we be better at than every other liquor company? How am I going to get into [customers’] repertoire? I think we probably could have saved millions of dollars and a few years had I just spent another three months thinking about that before we started Mr Black.”
Related: How to Turn Vision Into Reality — A Step-by-Step Approach to Achieving Your Goals
Jackie Summers – Sorel Liqueur
Summers recommends taking breaks to get an accurate accounting of your goals.
“Our culture says you must keep going at 100 miles an hour at all times,” Summers says. “If you don’t have a chance to reflect, you don’t get the opportunity to see what your strengths and weaknesses are and how you’re going to compensate for both. It’s important to cocoon on a regular basis — whether [that’s] 20 minutes of meditation a day or being able to get away once every few weeks and spend some time in nature and quiet your mind. Once you have clarity, all sorts of things can move forward.”
Irene Chen and Matthew Grenby – Parker Thatch
Parker Thatch makes handbags, but its “true mission” is about giving customers a confidence boost, Chen says — a guiding principle that helps other aspects of the business fall into place.
Finding that “why” helped supercharge the company and serves as a solid defense against inevitable industry challenges, like competitors that produce knock-offs, Grenby says.
“That ‘why’ is not something that’s not easily copyable,” he explains. “If it’s not authentic, people sense that, and they value authenticity.”
Image Credit: Courtesy of Parker Thatch. Matthew Grenby and Irene Chen.
Don’t wait forever to start — do take calculated risks
Jenny Just – PEAK6 Investments, Poker Power
Just emphasizes that strategic early risk-taking can pay off in spades.
“When we talk about women taking risks, it’s not about taking bigger risks,” Just explains. “It’s just taking more risks sooner, and what poker allows you to do is take those risks in a bite-sized way.”
Johanna Hartzheim – Wildgrain
Hartzheim recommends jumping in and learning as you go.
“Just go for it because it’s something you learn while doing,” Hartzheim says. “It sounds kind of cliche, but as long as you’re motivated and passionate, you can do anything. I knew nothing about tracking, importing, all these things, but it’s not rocket science. You can learn anything or find the right people who do know these things.”
Related: You Have to Take Risks to Succeed. Here Are 4 Risk-Taking Benefits in Entrepreneurship
Kathrin Hamm – Bearaby
Hamm suggests setting a definitive timeline to put your best foot forward.
“Once you believe in a product, just take a chance and give yourself a year,” Hamm says. “It’s much more manageable if you [have] a considerable time frame where it’s like, Okay, in that year, I’m giving everything I have, 100%. Because sometimes we second guess ourselves. After [a few] months or six weeks, we don’t see the success, [and] we start doubting ourselves. You say [I have] one year, and I’m not asking if this is working. Just have tunnel vision for one year, and then reevaluate after those 365 days.”
Image Credit: Courtesy of Bearaby. Kathrin Hamm.
Embrace failure and the learning-filled journey
Payam Zamani – Autoweb, One Planet Group
Zamani notes that entrepreneurial fulfillment doesn’t have to depend on a business’s success.
“The fact is the overwhelming majority of businesses don’t survive,” Zamani says. “So you want to make that journey worth experiencing, and not just seeking an exit, seeking an IPO that may never happen. Then you feel like, ‘Ah, that was a failure.’ But if you’re making that journey something that’s worth living, you will always feel fulfilled whether or not that climax comes about in your business.”
Bobbi Brown – Bobbi Brown Cosmetics, Jones Road Beauty
Brown suggests giving entrepreneurship a shot so you don’t have to wonder “what if.”
“If you don’t try, you’ll never know,” Brown says. “I don’t believe in failure because it’s just a message that if something didn’t work out, do it differently.”
Related: 7 Ways Companies Can Harness Failure to Drive Success
Ellen Bennett – Hedley & Bennett
Bennett cautions against aiming for overnight success because a slow and steady approach brings some of the biggest gains.
“I’m a huge believer in the long game,” Bennett says. “You can start something out of your house with no money and have a viable, profitable business that you are a majority owner of many years later. And that is awesome. There’s nothing wrong with taking longer to build something great. I know our whole lives are oriented towards speed and how quickly things grow and [becoming] a unicorn, but you can be a long-game unicorn, too.”
Missy Tannen – Boll & Branch
Missy Tannen emphasizes that aspiring entrepreneurs don’t have to have it all figured out from the start.
“You don’t have to know everything day one,” she says. “You’re going to learn so much along the way, and I think if we’d realized all the things we didn’t know, we would have never started.”
Image Credit: Courtesy of Boll & Branch. Missy and Scott Tannen.
Keep your priorities in check
Alexis Ohanian – Reddit
Ohanian wants to reframe the question of what it takes to achieve work-life balance.
“I don’t think it’s about work-life balance,” Ohanian explains. “I don’t think anyone can really accomplish that. It’s not about balancing. If you’re chasing balance, you’re implying, like Thanos, [that] you’d be able to create something perfectly balanced. And the reality is work-life [is] never 50/50. You’ll never achieve anywhere close to that — nor should you. There are times in your life where you will need to focus on the career, the work. There are times in your life when you need to focus on life. It’s on a spectrum that’s ever-flowing back and forth.”
Related: 5 Priorities for Young Entrepreneurs
Do good and do well
Wemimo Abbey – Esusu
Abbey stresses that responsible entrepreneurship doesn’t have to be a zero-sum game.
“We need to find ways where we can create a win-win-win construct across the board,” Abbey says. “We really believe in this idea of justice capitalism: We can do good and do well — and it’s by no means mutually exclusive.”
Cason Crane – Explorer Cold Brew
Crane acknowledges that not every customer will support Explorer Cold Brew because of its LGBTQ+ partnerships, but he’s committed to running a business that reflects his values.
“It certainly helps keep me going every day,” Crane says. “There are things that you do as a business owner to position your business for financial success, and then there are the things you do to keep yourself excited to get out of bed every morning. And I think it’s important as a business owner to do both.”
Related: How to Make Giving Back Part of Your Brand’s DNA
Randy Goldberg and David Heath – Bombas
Goldberg and Heath say founders must ensure the mission is “fully integrated into the business.”
“Every team at Bombas is responsible for the mission in either a direct or an indirect way,” Heath says. “And I think having that so intertwined makes our employees feel good about our mission. But it also makes it so that the mission shows up in everything that we do, from customer experience interactions, to the website, to the creative, to the product. It’s so much a part of our DNA that you could never separate the mission. It’s not an afterthought.”
Image Credit: Courtesy of Bombas. David Heath and Randy Goldberg.
Lead with intention and encourage creativity
Chris Kirby – Ithaca Hummus
Kirby explains what it takes to build a company culture that promotes ideation, risk-taking and learning.
“I’ve learned that true leadership is about empathy, clear communication and creating an environment where people feel valued and empowered,” Kirby says. “So I’ve worked hard to build a culture that’s the complete opposite of what I experienced in a lot of those kitchens. I want my team to feel safe to share ideas, take risks and learn from mistakes without fear of being punished.”
Scott Tannen – Boll & Branch
Tannen says that a business leader is only as good as the people with whom they surround themselves.
“I am not the most talented person in this company by miles,” Tannen explains, “and I think that’s a mark of a great company when I can say that.”
Related: What Makes a Good Leader? Here’s What I’ve Learned After 20-Plus Years as a CEO.
Jocelyn Gailliot – Tuckernuck
Gailliot says Tuckernuck leaders strive to learn from their team members, which means listening to them.
“We constantly ask [them] questions,” Gailliot says. “I’ve been in industries before where it’s very much: ‘This is the role you play at these different hierarchical levels.’ And for us, it’s always been: ‘You’re on the team — you have amazing ideas to contribute, and we want to hear them.’ And we really do.”
Richard Branson – Virgin Group
Branson cites Virgin Unite’s The Elders, a group of independent global leaders working for peace and human rights that has included leaders like Nelson Mandela and Jimmy Carter, as an example of strong leadership.
“They’re all great listeners,” Branson explains. “They know what they’re thinking. They don’t need to hear themselves saying it out loud, and the only way they can learn is by listening to other people talk.”
Work hard to achieve the results you want
Amir Loloi – Loloi Rugs
Loloi says that the only person standing in the way of your business success is yourself.
“If you dream big and work hard, no one is there to stop you,” Loloi explains. “It’s not about the color of your skin. It’s not about your background. It’s not about your religion. It’s not about anything except about you personally: What are you willing to do? When you are given a task, how much more are you willing to add to it to deliver so much more? If you want to be someone in life, step out of the boundaries.”
Image Credit: Courtesy of Loloi. Amir Loloi and his sons.
Adriana Carrig – Little Words Project
Carrig suggests a three-pronged strategy to realize your biggest dreams.
“If you want it bad enough that you’re willing to work for it and believe in yourself, and all those things come together in this perfect trifecta, then there’s nothing you can’t achieve,” Carrig says. “So go for it.”
Related: 7 Elements of a Strong Work Ethic
Fawn Weaver – Uncle Nearest Premium Whiskey
According to Weaver, entrepreneurs need to give the business their all — or rethink it altogether.
“If you’re not going to do it with excellence and with consistency, bow out and get a job,” Weaver says. “Period. If you are going to do it with excellence and with consistency over time, don’t let anybody slow you down — no one. Just keep going after it, because the only people that fail doing it with excellence and with consistency are those who give up before they succeed.”
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A Joann store in Miami, Florida. Photo by Joe Raedle/Getty Images
JPMorgan CEO Jamie Dimon. Photographer: Kent Nishimura/Bloomberg via Getty Images
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