Business

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.

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.

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.

Table of Contents

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.”

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.”

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.”

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.”

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.”

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.”

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.”

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.”

1740607859 LoloiFamilyPortrait2023 Final

^{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.”

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.”

Intellectual Insider

+ posts

A blog which focuses on business, Networth, Technology, Entrepreneurship, Self Improvement, Celebrities, Top Lists, Travelling, Health, and lifestyle. A source that provides you with each and every top piece of information about the world. We cover various different topics.

Business

Trying Your Best When There’s Little To No Chance Of Succeeding

If you knew that no matter how hard you tried, success was impossible or practically impossible, would you still push yourself to the limit? Or would you rationally pivot to another endeavor with a real chance of success? Personally, if the odds were overwhelmingly against me, I’m not sure I’d bother trying so hard.

Since my kids were born, I’ve noticed a growing trend: highly academic Asian American students with stellar GPAs and top SAT scores getting rejected from most of their top-choice colleges. This is common for many students, especially as admissions rates plummet due in part to the ease of applying through the Common App. However, the challenge seems even more pronounced for Asian applicants.

Although Asian Americans make up only about 7% of the U.S. population, they aren’t considered a minority group eligible for preferential treatment in college admissions, jobs, or promotions. Instead, based on average SAT and ACT scores by race, it appears they must score higher than other groups just to have an equal chance of acceptance. The Supreme Court acknowledged this disparity when it ruled against affirmative action on June 29, 2023.

When diversity, equity, and inclusion (DEI) became a dominant movement after George Floyd’s killing in 2020, Asian Americans were largely left out of the racial justice conversation—even though they, too, have faced discrimination and hate. I get it—Asians have the highest median income among all racial groups, so why prioritize a group that’s perceived as doing well?

But what if you’re a poor Asian from a broken family? In that case, you might just be out of luck. Your only solution is to just try harder.

Table of Contents

Students Could Have Enjoyed Life More

During the pandemic, I had an epiphany: What’s the point of my kids studying so hard if their chances of getting into a top college—and landing a promising job afterward—are slim to none?

Instead of stressing over straight As, top SAT scores, varsity sports, club leadership, and curing cancer, why not let them fully enjoy their youth? All this intense stress to get into a top college doesn’t seem healthy.

The rise in depression and anxiety among high school students is alarming, with many feeling relentless pressure to excel. Some even take their own lives because they don’t feel good enough academically. We cannot let that happen. I refuse to let my daughter and son suffer under the weight of status and money at the expense of their well-being.

Youth mental health and the rise of major depressing among teens and emergency room visits for self-harm - Trying Your Best When You Have No Shot Of Succeeding

A Better, Happier Childhood When You Have No Chance

Imagine waking up excited to go to school—not for grades, but for the sake of learning. You’d focus on subjects you care about and do just enough to pass the ones you don’t like the quiet quitters today. Since the odds of getting into a top 25 university are so low, you’d be content with a B-average and a sub 1,200 SAT score. With lower expectations, you’d feel grateful for whatever college you do get into.

What a fantastic K-12 experience! I was all in on this idea—no Tiger Dad pressure, no pushing my kids to grind for a top-tier university just to buy an expensive house close to work to become bankers working under fluorescent lights for 60 hours a week. I’ve been there, and it’s not fun, even if the money was good.

Instead, they could go to community college, save a fortune, and pursue careers they actually enjoy. And with the $700,000+ each that would have otherwise gone to private university tuition, I’d find a way to gift them financial security early.

Then things changed in 2025. Intense merit-based rewards came back into focus under the new administration.

SAT scores by race from 1941-2020 - Trying Your Best When You Have No Shot Of Succeeding

The Analogy Of Lower Taxes Hurting Your Lifestyle

To help explain the negative of merit-based reward, let’s look at tax policy as an example.

When taxes are cut, people work harder because they get to keep more of their earnings. In theory, this is great—especially if the government has been wasting taxpayer dollars.

But the problem with working harder and longer is that money is addictive. Many people don’t know when to stop, even after they have enough. Fast-forward 40 years, and the rich banker or techie might wonder why they spent so much time chasing money when they could have been doing something more fulfilling.

I see this addiction to wealth every day through Financial Samurai. People worth millions of dollars struggling to be happy. It’s extremely hard to quit making money, even if you hate your job. That’s why I started writing about FIRE in 2009—to give people the courage and financial framework to walk away from work they despise and do something they love.

Yes, making a lot of money and investing wisely is great. But if you keep sacrificing time for more money when you already have enough or are on track to die with plenty, it’s a damn shame.

I left work in 2012, partly because I didn’t want to pay ~40% of my income to the government for the privilege of working 60 hours a week and feeling constantly stressed. So in a way, I’m thankful for President Obama for raising my federal marginal income tax rate to 39.6% and giving me the incentive to break free. Paying another 12.3% tax to California plus another 7.2% in FICA tax was simply not worth it anymore.

Screen time's affect on U.S. teenagers on anxiety and depression - Trying Your Best When You Have No Shot Of Succeeding — The less screen time for our children, the better

Merit-Based Reward Can Also Hurt Your Lifestyle

On the surface, rewarding people based solely on merit sounds fair. But it could also be a trap for the most ambitious among us.

When people realize they can get ahead by outworking their peers, they’ll do just that. A 60-hour workweek turns into 70 hours. Then 80. Then 90. The arms race for more never ends until we make it stop.

Just like money addiction is hard to quit, merit-based competition is, too. When you know effort directly correlates with reward, it’s tough to hold back. If I was paid based on performance at my old job at Credit Suisse, I would have for sure lasted for at least another 5-10 years.

Today, if I knew I could outpace AI from stealing my content just by writing more, I’d keep going indefinitely. But I recognize my window of opportunity may be closing fast. That’s why I’ve invested in the very companies working to make me obsolete. If they’re going to take away my retirement dream, at least I plan to profit in the process!

MCAT and GPA scores by race = Trying Your Best When You Have No Shot Of Succeeding

Rejected Asian American Goes Straight To A Dream Job

Take Stanley Zhong. He had a 3.97 unweighted GPA, a 4.42 weighted GPA, and a near-perfect 1590 SAT score at Gunn High School. He even founded his own document-signing startup and tutored underserved kids in coding.

Yet, he was rejected by 16 colleges, including MIT, Carnegie Mellon, Stanford, UC Berkeley, UCLA, UCSD, UCSB, UC Davis, Cal Poly San Luis Obispo, Cornell University, University of Illinois, University of Michigan, Georgia Tech, Caltech, University of Washington and University of Wisconsin.

UC Davis has a 42% acceptance rate for goodness sake! Did Stanley write something offensive in all his essays? That would be hard to believe given he has such a thoughtful father and helpful school counselors.

When I first heard the news in 2023, I was stunned. Stanley could have been my son. And if he wasn’t good enough, what chance did my kids have? Less than 1% of students can achieve the academic scores Stanley achieved. For a moment, I felt defeated. Why bother trying? Top universities will simply use subjective reasons such as personality scores to explain why a student was rejected.

But then something remarkable happened.

Instead of going to college, Stanley landed a PhD-level engineering role at Google—a job most computer science grads from the very schools that rejected him would kill for. Making $200,000+ right out of high school is a dream come true.

Stanley proved his naysayers wrong. Although, his dad also works at Google, so maybe dad was able to help out in some way.

Building Skills Becomes En Vogue Again

His story made me reconsider. Merit won out in the end—not in college admissions, but in the job market, the ultimate end goal. Businesses, unlike universities, need the best workers to create the best products and maximize profits.

If the most elite employers with the largest balance sheets like Google and Meta can no longer afford to ignore merit, the same will happen across smaller companies. Merit is even more important if you are an entrepreneur. There is nowhere to hide if you’re the one doing most of the work.

Then, in February 2025, Stanley and his father sued the University of California for racial discrimination. Despite all the hate they received, they pressed forward for future Asian American students who might face the same bias. Personally, I don’t think they will win since Asians make up around 36% of the student population at the UC system, yet account for 19% of California high school graduates who met UC admission requirements.

Stanley Zhong, a school grad rejected from 16 top schools, landed a job at Google right after high school. Now he and his father are filing a lawsuit against University of California and five campuses, alleging that there is racial discrimination in its admissions process. pic.twitter.com/DMsp2Of2qc

— ABC7 News (@abc7newsbayarea) February 21, 2025

But if they win, it could mean more qualified Asian Americans will get into public universities that receive government funding. Can you imagine paying property taxes for 18 years only for your straight-A kids to get rejected? Ultimately, a lawsuit victory should benefit the best students of all races as they wouldn’t have to be worried as much about subjective factors dying them anymore.

So, that crazy dream I had—of Asian American kids enjoying a low-stress, joyful childhood—might have to wait. For now, merit is back in focus, which means long hours of studying, intense competition in extracurriculars, and enormous pressure. If we decide to go this route, parents must always be encouraging and supportive.

Treat Your Parents Well

Regardless of what happens, one truth remains: be good to your parents.

Colleges and employers may reject you, but your parents likely never will. They’ll do whatever it takes to give you opportunities and, ultimately, ensure that you’re happy.

And if they’ve been smart with their money—investing through a mostly bull market—they might have more wealth than you realize. When the time comes for college, a car, or even a house, they might just cover everything for you.

As a parent myself, I constantly battle the urge to give my kids everything. But I know that if I do, I risk making them entitled and soft.

Still, if my son and daughter grow into responsible, kind adults who choose careers that genuinely help others, it’ll be tough not to give them financial support when they need it.

When Your Best Is Not Good Enough: Keep On Going

So no matter your race, your best bet is to keep striving even if you have little-to-no chance of succeeding. Your pride is at stake. Even if you face rejection after rejection, remember—rejection is just the price of success.

Keep pushing. Keep grinding. This is a million-dollar mindset worth adopting. Recognize the world will never be fair. Accept it! Even when the odds are stacked against you, your hard work will eventually pay off in ways that are hard to forecast.

Readers, how do you feel about trying your best despite the long odds of success? Are you disappointed about the hyper focus on merit, or do you welcome the increased incentive to work hard? Why do you think students like Stanley Zhong, with near-perfect academic records, get rejected by so many top colleges? Does this prove the importance of writing good essays?

To build more wealth than 90% of the population, order a copy of Millionaire Milestones: Simple Steps to Seven Figures. I’ve distilled 30+ years of financial wisdom into one book to help you achieve financial freedom sooner. But success requires action—don’t wait! In 10 years, you will wish you had taken the appropriate financial steps today.

Millionaire Milestone - Bestseller On Amazon — Click to order a copy on Amazon today

To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter. Financial Samurai is among the largest independently-owned personal finance websites, established in 2009. Everything is written based on firsthand experience and expertise.

Intellectual Insider

+ posts

Business

Hi, Thanks for Reading My Column in the March/April Issue!

Thanks for reading my column! I’ve been thinking a lot about how to connect better with audiences, and wanted to share some thoughts with you here.

As I promised in the video above, here are a few other ways to connect: You can connect with me on LinkedIn, where I post daily, or subscribe to my weekly newsletter full of success tips. Replies go directly to my inbox!

See you in the next issue of Entrepreneur magazine.

Intellectual Insider

+ posts

Business

Starbucks Is Cutting 13 Drinks From Its Menu Next Week: List

Starbucks has been making a slew of changes in recent months as new CEO Brian Niccol tries to turn around the coffeehouse’s lagging sales. It has revamped the code of conduct, added ceramic mugs, and capped mobile orders. On Monday, the company announced it was laying off 1,100 corporate jobs.

Now, the coffee giant is also cutting its menu.

In an announcement posted to the company’s website, Starbucks said it would eliminate 30% of its menu by the end of fiscal year 2025 in the U.S. The cuts begin next week on Tuesday, March 4.

“We’re simplifying our menu to focus on fewer, more popular items, executed with excellence,” the statement says. “This will make way for innovation, help reduce wait times, improve quality and consistency, and align with our core identity as a coffee company.”

Despite the cuts (see full list below), Starbucks is still adding new items. The announcement touts its recently launched “premium” Cortado espresso beverage, which “has already performed beyond our expectations.”

Starbucks will also bring back its Lavender beverages lineup this spring and introduce an “Iced Cherry Chai” and “Jalapeño Chicken Pocket” sandwich.   

“We’re helping to create a more intentional, thoughtful experience for our customers — one where every drink is handcrafted with precision and care,” the company said.

Starbucks shared the full list of the drinks that will be eliminated with The Associated Press. Here’s what is being cut next week.