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.

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.”

^{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.”

Business

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Business

The Most Common Tax Planning Mistakes For High Earners

If my posts on the mistake of chasing value stocks or the need to invest big money to make life-changing money don’t resonate, consider hiring a financial professional to manage your portfolio. You may not be obsessed enough to consistently invest the amount needed to retire comfortably. Offloading the burden of investing frees up your time and energy to focus on work, family, and hobbies.

At this moment, I’m preparing to do my taxes again. Every year I file an extension (Oct 15 deadline) because of delayed K-1s from private fund investments. So when Empower reached out about highlighting tax planning mistakes for high earners, I agreed. It’s a topic I know all too well.

What I didn’t realize is that Empower offers tax planning as part of its standard client service. No extra invoices, no $300/hour CPA bills. Just integrated advice, included in the management fee. Considering that taxes are often the single largest expense for high-income earners, having proactive strategy baked in is a big deal.

The Importance Of Tax Planning For High Income Earners

When you’re a high earner—think $250,000+ income or the potential to get there—you’ve probably got a lot on your plate: investments, real estate, maybe a business or two. What you might not be paying enough attention to? Tax planning.

It’s not sexy like a moonshot AI stock, but the compounding effect of smart, consistent tax moves can rival investment returns over time. As Empower Personal Wealth specialist Scott Hipp, CPA, CFP® explains, for high-income, high-net-worth clients, tax planning isn’t about chasing one-off loopholes, it’s about proactive, coordinated, year-round strategy.

Let’s dive into four key questions Scott answered that reveal just how much value smart tax planning can deliver. If you’re searching for a financial professional to manage your wealth, choosing one that integrates tax planning into their service is essential, not an add-on.

Empower has been a long-time affiliate partner of Financial Samurai, and I personally consulted for Personal Capital (later acquired by Empower) from 2013 to 2015. I’ve seen firsthand how incorporating tax strategy into wealth management can meaningfully boost long-term returns.

1. Why is tax planning critical for high earners?

When you’re in the top federal tax brackets—32%, 35%, or 37%—every strategic move counts more. Saving 1% on taxes for someone making $100K is nice. Saving 1% for someone making $800,000? That’s four first-class tickets to Hawaii with a couple thousand left over.

Scott says most people think of tax planning as a once-a-year scramble or a hunt for magical loopholes (“I heard Uncle Bob pays zero taxes because he made his dogs employees…”). The truth: the biggest gains come from small, consistent, legal moves year after year.

It’s like The Shawshank Redemption: pressure and time. Maxing out a health savings account, backdoor Roth contributions, charitable “bunching,” and tax-loss harvesting may seem minor in isolation, but over 20 years, they can carve a serious tunnel toward financial freedom.

Here’s the danger: by the time you file in April, most opportunities are gone. If you’re filing 2025’s taxes in April 2026, your deadline for most strategies was December 31, 2025. That’s why Empower’s team works year-round—advisors and tax specialists meet regularly to tweak and optimize before the clock runs out.

2. What’s the deal with the SALT deduction changes?

The State and Local Tax (SALT) deduction cap got a temporary boost after the passage of The One Big Beautiful Bill Act on July 4, 2025. It’s $40,000 in 2025 (up from $10,000), rising slightly each year until 2029, before reverting in 2030.

Who benefits? Mostly taxpayers with AGI under $500K in high-tax states. Hit $600K AGI, and the expanded cap phases out completely.

But even high earners over $600K aren’t out of luck—if you own a pass-through business (S-corp, partnership, LLC taxed as such), you might use the Pass-Through Entity Tax (PTET) workaround. Here, the business pays state taxes, making them fully deductible federally, and you get a state tax credit. As of 2025, 35+ states have a PTET option.

For the right clients, SALT changes + PTET can unlock deductions worth tens of thousands—money that stays in your portfolio instead of the IRS’s coffers.

3. How does Empower approach complex high-earner situations?

Let’s say you’re a business owner with significant investment income, passive rental income, and real estate holdings.

With Empower, you basically have a “tax specialist on demand” baked into your fee – no surprise bills. The process starts with:

Reviewing the past three years of returns for missed opportunities. (You’ve got three years to amend and claim a refund.) Empower can spot thousands in overlooked deductions.
Holistic planning based on your goals. Tax strategy isn’t in a vacuum—it’s tied to your investment plan, estate goals, and cash flow needs.

Common missed opportunities for self-employed clients:

Not deducting health insurance premiums.
Missing the Qualified Business Income (QBI) deduction.
Ignoring home office deductions.

More common errors Empower can help catch:

Capital loss carryforwards lost when switching preparers/software
Incorrect Backdoor Roth processing
Missed Foreign Tax Credit
Wrong cost basis for stock sales (ESPP, options)
HSA distributions taxed in error

From there, Empower looks forward—maybe setting up a solo 401(k), timing income, or planning capital gains. The idea is to create an ongoing tax playbook, not just fix past mistakes.

4. What real-world tax savings have clients seen?

Missed health insurance deductions are surprisingly common—and costly.

S-Corp owner: CPA added health insurance premiums to W-2 wages (correctly) but never told the client they could deduct those premiums above the line. Amending three years’ returns saved ~$6,000 in federal taxes.
Sole proprietor: Deducted health insurance as a Schedule A itemized deduction, but couldn’t benefit due to medical expense thresholds and not itemizing at all. Amending saved ~$7,500.
Medicare premiums: Many don’t know they qualify as self-employed health insurance deductions. Catching this can save $1,000+ per year.

These aren’t flashy hedge-fund-like wins—but they’re guaranteed returns via tax savings, often compounding over years.

Key Strategies Empower Uses for High Earners

Scott shared a few proactive moves that come up again and again:

Bunching Charitable Contributions

Standard deduction in 2025: $15,750 (single) / $31,500 (married). By combining two or more years of donations into one tax year, you can exceed the standard deduction, itemize that year, and take the standard deduction the next—resulting in a bigger total deduction over time.

Bonus: Donate appreciated assets or use a Donor-Advised Fund for even more efficiency.

Tax Loss Harvesting

Selling investments at a loss to offset gains elsewhere—then reinvesting in similar (but not “substantially identical”) assets—can lower your current-year tax bill while keeping your portfolio allocated. All Empower Personal Strategy clients ($100K+) minimize your tax burden with proactive application of tax-loss harvesting and tax location.

Roth Conversions

Moving funds from a traditional IRA to a Roth IRA lets you lock in today’s tax rate if you expect to be in a higher bracket later. Future withdrawals? Tax-free. This is especially powerful in lower-income years before RMDs kick in.

Saving Money On A Good CPA

A good CPA might charge $150–$400/hour just for tax consultations. Meanwhile, many don’t offer proactive planning at all, focusing instead on compliance and filing.

Empower builds tax planning into its overall wealth management service for clients with $100K+ in investable assets. That means:

One fee, one integrated plan.
Advisors and tax specialists in the same room (or Zoom) all year.
Proactive calls before the deadlines—not “we’ll see you next April.”

The Bottom Line

Big investment wins get the headlines, but year after year, quiet, boring, proactive tax moves can be worth just as much, sometimes more. For high earners, ignoring tax planning is like leaving compounding on the table.

If you’ve got $100K+ in investable assets, Empower is offering Financial Samurai readers a free consultation. Even if you’re confident in your current plan, a second opinion could uncover thousands in missed opportunities.

For a limited time only, book your free, no obligation session here. An Empower professional will review your investments and net worth, and offer some suggestions on where you can optimize, all for free.

Empower’s Tax Optimization Services

Tax optimized investing (tax loss harvesting, tax location, tax efficiency): available to clients investing $100K+.

Tax planning guidance (analysis and recommendations – identify gaps and opportunities in your tax strategy before you file with your advisor and tax specialist): available to $250K+.

At $1M+, clients receive the above, in addition to access to a CPA, at no additional cost.

Disclosure: This statement is provided by Kansei Incorporated (“Promoter”), which has a referral agreement with Empower Advisory Group, LLC (“EAG”). Learn more here.

To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter. Financial Samurai is the leading independently-owned personal finance site today, established in 2009.

Business

How To Eliminate That Intense Financial FOMO You’re Feeling

Back in 2012, I thought I had finally conquered financial FOMO after walking away from a well-paying finance job. But after having children, I’ve noticed more and more relapses. If you’ve found yourself battling the desire for more money than you truly need, this post is for you.

Ever since returning to San Francisco from our 36-day trip to Honolulu, I’ve been feeling a greater sense of FOMO. The first week back hit especially hard when Figma IPOed and surged 333% on its first day. Suddenly, we were right back to frenzied markets, with retail investors piling in at sky-high prices.

In Honolulu, my focus was on mainly three things: 1) family, 2) exercise, and 3) remodeling my parents’ in-law unit. Those three priorities consumed all my bandwidth. Between supercommuting and construction, I was spent most days, with little time left to think about chasing investments.

Pickleball and then the beach were my escape. While waiting for the next game, conversations revolved around recapping rallies, kids, or which store sold the best Pirie mangoes. Careers and investments never came up, except when I asked a couple players about Honolulu’s cost of living. The vibe was refreshingly present, grounded, and calm.

The Return Back Was Somewhat Jolting

I had never taken my family on such a long trip before, so the contrast with life back home was especially clear.

With just the four of us at home, family logistics became simpler, familiar camps smoothed out childcare every other week, and the remodeling burden was finally lifted. With all that mental headspace freed up, my mind inevitably drifted back to the markets and to the unsettling realization that the AI boom was racing ahead without me.

On the pickleball courts here, the chatter couldn’t have been more different. Nearly everyone was talking about tech stocks, the bull market, and the next big AI play. Why? Because nearly everyone either works in tech or invests heavily in it. There was no escaping the mania. I found myself longing for the calmer rhythm of Honolulu again.

The Moment That Reduced My FOMO Tremendously

Then something unexpected happened that broke my financial FOMO fever. The first weekend back home, I went to a neighborhood gathering at a local park. Familiar faces were everywhere, including one dad I occasionally hang out with. He works in venture, so I asked whether he ever felt the same financial FOMO I’d been struggling with since returning.

He shrugged. “Kinda, but not really.” Why would he? He spends his days looking for the next big winner, so opportunities are always flowing across his desk. Though he did mention once passing on a company that went on to be a huge success.

That surprised me. If anyone should feel FOMO, it’s investors who had the chance and said no, far worse than never getting a look at all, which is the reality for most of us. If I never had the opportunity, then there was no missing out in the first place. But it also made sense he didn’t feel much financial FOMO since he was already immersed in the hunt for more.

We kept chatting. He asked how my summer had been, so I shared some stories from our time away. Naturally, I asked about his summer too, expecting to hear about some big trip since his family had traveled a lot before. But instead, he told me they hadn’t gone anywhere. He’d been too busy working. Two months into summer, and he was still grinding away.

That was my “ah hah” moment. Suddenly, my financial FOMO evaporated. Here was someone, at least twice as wealthy as me, stuck at home because of work. It reminded me of my banking days, when I had to ask for permission to take vacation—like a kid asking his parents for pocket money. What a crock!

I’m sure his hard work this summer will make him millions more. But he’s already rich. At our age, I don’t want to sacrifice too much time with my kids for incremental wealth that won’t materially change our lifestyle. 18 summers isn’t a lot. I’ve got enough passive income to cover our family’s basic needs. That freedom, I was reminded, is worth more than chasing the next big score.

The Six Steps To Reducing Your Intense FOMO

Financial FOMO comes from comparison, insecurity about our own progress, and the fear of missing a once-in-a-lifetime opportunity. It tends to peak during bull markets, when it feels like everyone else is getting rich except you.

I’m not sure anybody is truly immune to financial FOMO. You can be wealthy, financially independent, retired, or even work in venture capital, and still feel it. But FOMO left unchecked can push you into bad investment decisions, such as buying at peaks, overextending on margin, or constantly second-guessing yourself.

Here are six tactical yet practical steps that may help you manage FOMO better:

1) Build a Core Portfolio You Rarely Touch

One of the best ways to combat FOMO is to remind yourself that you already own a piece of the future. If you’re invested in equities, real estate, Bitcoin, or venture, you’re covered. Even holding something as simple as the S&P 500 means you’re participating in the ongoing growth of our economy. The exact mix of your asset allocation is up to you. What matters most is having a stake in assets that can carry you forward, so you don’t feel pressured to chase every hot new opportunity.

I keep the bulk of my public equity investments in broad index funds. Meanwhile, about 40% of my net worth in real estate, and 15% in private companies.With a solid core, it becomes much easier to tune out the noise and ignore the hype cycles.

For example, if AI truly sparks a wave of IPOs, new startups, and thousands of newly minted millionaires, at least my San Francisco real estate should benefit. I recently experienced a rental bidding war for one of my properties and that’s before the AI IPO wave has even arrived. Investing in the picks and shovels helps ensure you will financially benefit, no matter what.

2) Allocate a “FOMO Fund”

Instead of trying to suppress the urge to participate, give yourself permission, but with guardrails. Roughly 40% of my public equities are in individual growth names, mostly tech. This way, when I see headlines about breakthroughs, like quantum computing, I feel like I’m part of the story rather than left on the sidelines. Of course, during the next correction, I will also lose more than the average index fund investor too.

I’ve also carved out a dedicated “FOMO Fund”—about 5% of my overall portfolio—for speculative money. That’s where I can dabble in individual private companies, new venture funds, or even short-term trends. If it pays off, great. If not, it won’t derail my financial plan. By containing the risk, you scratch the itch while protecting your long-term wealth.

3) Systematize Your Investing With Automation

One reason FOMO hits so hard is because investing often feels optional and emotional. A simple antidote: automation. Dollar-cost averaging into index funds, ETFs, individual stocks, or funds removes the decision-making stress. When money flows into the market on a schedule, you don’t sit around debating whether to chase the next hot stock. Instead, you’re already steadily invested, no matter what the headlines say.

For example, after opening a new personal Innovation Fund account earmarked for my kids with $26,000 ($500 bonus if you invest over $25,000), I enrolled in auto-invest at $2,500 a month. It’s enough out of my cash flow to feel involved without feeling strain. One year later, that’s $30,000 invested; after 10 years, $300,000.

Without automation, it’s easy to fall off track because life gets busy. I have over 30 investment accounts to manage between the four of us. Inevitably, I’m going to miss something, which is why automation is so important to free up mental bandwidth.

I’m concerned my kids may have little chance of becoming financially independent on their own in an AI-driven, hyper-competitive world. Therefore, every dollar I automate for them helps reduce that concern, while ensuring their money is working even if I get distracted.

Make investment contributions automatic through monthly auto-investing to help you reduce financial FOMO

4) Use Opportunity Cost as a Filter

Before jumping on the next hot idea, I try to ask: What am I giving up if I do this? Am I sacrificing cash flow, peace of mind, or time with family? Am I risking capital I’ll need in five years for housing, education, or flexibility? During bear markets, I certainly get a little more moody. By forcing yourself to weigh trade-offs, you realize some FOMO-driven decisions don’t actually pass the test. I

As someone who enjoys investing more than spending, this opportunity cost exercise often flips for me. I tend to think instead: What is the opportunity cost of spending money on something I don’t really need versus the potential returns if I invested it? Buying this unnecessary $120,000 Range Rover could turn into $300,000 in five years if invested well!

Still, the reality is that not all investments work out, especially the most speculative ones. Corrections and bear markets are a natural part of investing. Which is why it’s worth asking a different version of the question too: What are the joys I’m giving up today in exchange for an investment that may never pan out? That balance helps keep you grounded, whether you lean toward spending or investing.

Losing Money Quickly

Just look at the Figma IPO. I suspect FOMO drove many investors to pile in on day one, paying $100–$133 a share. Fast forward just a few weeks, and the stock is already down about 40% from its peak. I would much rather have spent $25,000 on a memorable family vacation than invested it in Figma and watched $10,000 vanish in two weeks. YOLO!

Chasing hot IPOs at extraordinary valuations is dangerous, so please be careful. Instead, consider investing in these companies before they go IPO so you can sell to investors who experience maximum FOMO.

Always remind yourself that you can and will lose money when it comes to investing in risk assets. Sometimes, this fact is easy to forget during a bull market.

How to reduce financial FOMO and not chase hot IPO stocks like Figma

5) Define “Enough” Clearly

FOMO often creeps in when you don’t have a clear baseline for what success actually means to you. If your target is always a vague “more,” then no matter how much progress you make, someone else will always appear to be ahead – whether it’s their bigger house, higher net worth, or latest hot investment. That mindset makes contentment impossible.

What helps is defining enough. For me, that’s when passive income reliably covers our family’s basic living expenses. Once that box is checked, every dollar beyond is truly optional. I can put it toward growth investments, donate it, or try to spend it guilt-free on experiences.

After I hit a passive income target, I try and shift my mindset back toward an early retirement lifestyle. This means less striving, more enjoying. Anchoring to “enough” quiets the noise, and reminds me that I’ve already got enough.

Once you know your number and can sustain your lifestyle, you realize chasing endlessly isn’t freedom, it’s another form of bondage.

6) Change Your Environment

Finally, FOMO isn’t just about the markets, it’s about the people around you. Living in go-getter cities like San Francisco or New York means you’re constantly surrounded by the most ambitious and competitive people. Many of whom are making big money in tech, finance, or startups. The conversations, the headlines, even the birthday gatherings, it all feeds into a sense that you’re in this constant battle where you’re often falling behind.

One way to dial that back is to physically change your environment. Moving to, or even spending extended time in, a slower-paced city or town gives you space to breathe. Suddenly, not everyone is talking about the latest IPO or AI fundraise. Conversations shift to family, community, or quality of life.

It doesn’t mean giving up ambition or opportunity, you can still build wealth anywhere. But by lowering the ambient noise of competition, you reduce the constant comparison game that fuels financial FOMO.

Final Thoughts On Getting Rid Of FOMO

Markets will always swing from euphoria to despair, and there will always be someone making more money than you. But with a sound core portfolio, a small space to take punts, and a clear definition of enough, you can stay disciplined while still scratching the investing itch.

FOMO doesn’t disappear, but with the right systems, it can be managed so it doesn’t manage you.

Readers, do you experience financial FOMO? If not, how do you manage it so you don’t feel like you’re constantly missing out on financial gains? Interestingly, the vast majority of people I speak with in real life say they don’t really struggle with financial FOMO. That makes me curious — what strategies do you use to tame this beast?

Invest in AI So You Don’t Get Left Behind

AI is set to disrupt the labor market in a massive way, for you and for your kids. One way to hedge against that disruption is to invest in AI itself.

With Fundrise’s venture capital product, you can gain exposure to leading private AI companies like OpenAI, Anthropic, Databricks, Anduril, and more. The minimum investment is just $10, and new accounts currently get a $100–$200 bonus.

I recently opened a new account for my children with $26,000 and will auto-invest $2,500 a month for the foreseeable future. My hope is that by riding the AI wave, they’ll benefit from the very disruption that might otherwise work against them.

Fundrise is a long-time sponsor of Financial Samurai, and Financial Samurai is an investor in Fundrise products. Our investment philosophies are aligned. Overall, I’ve invested more than $350,000 in Fundrise Venture.

Fundrise Innovation Fund Financial Samurai investment amount and dashboard - Overcoming FOMO in AI by investing in AI — My current Fundrise Venture investment dashboard, excluding the $26,000 I recently invested for my children

Pick up a copy of my USA TODAY national bestseller, Millionaire Milestones: Simple Steps to Seven Figures. I’ve distilled over 30 years of financial experience to help you build more wealth than 94% of the population and break free sooner. When you’re ahead, that FOMO starts to disappear.

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