Table of Contents
After a nine-figure exit, most founders assume their next venture will be easier—but Harvard research reveals 70% fail, and Anastasia Koroleva explains exactly why.
Anastasia Koroleva sold her bootstrapped company for nine figures, then watched her life unravel through divorce, business failure, and identity crisis—revealing why most post-exit founders struggle for a decade.
Key Takeaways
- Harvard research shows 70% of second businesses fail, despite founders having more experience, networks, and capital than ever before
- Post-exit founders typically struggle for 10 years on average before finding genuine fulfillment beyond their initial success
- Four major traps derail second ventures: rushing too quickly, entering unfamiliar industries, lacking self-awareness about strengths, and sudden wealth syndrome
- Cognitive dissonance between expectations and reality creates overwhelming psychological discomfort that most founders try to escape rather than resolve properly
- True financial freedom requires confronting money psychology first, then rebuilding basic needs like safety and belonging that the sold business previously provided
- Successful post-exit navigation involves three phases: rest and recovery, expanding life experiences, then rebuilding fundamentals using frameworks like Maslow's hierarchy
- Wealth management should prioritize cash flow over net worth, with portfolios designed for low stress rather than maximum returns
- The most fulfilled post-exit founders eventually use wealth as leverage for purpose-driven work that contributes meaningfully to society
Timeline Overview
- 00:00–00:53 — Introduction: The Big Picture Trap: Why most founders fall into predictable patterns and struggle for years after successful exits
- 00:53–03:07 — Meet Anastasia's Net Worth: From nine-figure exit to high eight figures through divorce and poor decisions, plus the psychology of wealth loss
- 03:07–05:13 — From Moscow to Silicon Valley: Anastasia's Early Career: Growing up during Soviet collapse, becoming a journalist at 13, law school, and meeting her startup co-founder
- 05:13–08:11 — Building and Selling Businesses: The Highs and Lows: Six years building a bootstrapped SaaS company to nine-figure exit while raising toddlers
- 08:11–18:09 — The Emotional Rollercoaster of Post-Exit Life: Immediate post-exit confusion, divorce, failed second venture, and the loneliness of sudden wealth
- 18:09–24:58 — Understanding the Common Pitfalls of Second Ventures: The four categories of failure including timing mistakes, naive industry jumping, and self-awareness gaps
- 24:58–30:22 — The Psychology Behind Post-Exit Challenges: Sudden wealth syndrome, cognitive dissonance theory, and why most founders take 10 years to adjust properly
- 30:22–31:09 — Resolving Cognitive Dissonance: How successful founders embrace paradox rather than seeking oversimplified solutions to complex emotional challenges
- 31:09–32:15 — The Paradox of Freedom: Why unlimited freedom creates decision paralysis and how to build meaningful structure around newfound autonomy
- 32:15–33:16 — Confronting Financial Freedom: The importance of creating genuine financial safety before pursuing holistic life upgrades and purpose-driven work
- 33:16–34:52 — The Three Levels of Wealth: From financial freedom to holistic life improvement to using wealth as leverage for meaningful purpose
- 34:52–35:27 — The P&L of Life Post-Exit: Understanding what exits give you (freedom, time, money, reputation) versus what they take away (business, social circle, identity)
- 35:27–38:09 — Maximizing Post-Exit Assets: How to get the most value from freedom, energy, and reputation rather than immediately jumping into new ventures
- 38:09–39:58 — The Baby Bear Solution: Finding the right timing between starting too early (Papa Bear) and waiting too long (Mama Bear) for your next venture
- 39:58–49:24 — Rebuilding the Basics: Using Maslow's hierarchy to reconstruct safety, belonging, and self-esteem that your sold business previously provided
- 49:24–55:43 — Managing Wealth Post-Exit: Anastasia's portfolio strategy with 65% liquid assets, 25% private credit, 10% private equity, plus spending $650K-$1M annually
- 55:43–END — Life After the Exit: How Anastasia found purpose helping other founders navigate post-exit challenges through her programs and podcast
The Shocking Reality of Second-Time Founder Failure
The conventional wisdom around entrepreneurial success couldn't be more wrong. We assume that founders who've already built and sold successful companies have massive advantages for their next venture—deeper networks, more capital, proven experience. Yet Harvard Business School research reveals a startling truth: 70% of second businesses fail.
Anastasia Koroleva learned this statistic the hard way. After bootstrapping and selling her software-as-a-service company for nine figures, she immediately jumped into a health tech venture that she eventually had to shutter. The failure left her crying for two months, feeling like she was "burying a baby."
Her story challenges everything we think we know about entrepreneurial success. Despite having more resources than most founders ever accumulate, she found herself making what she now calls "very stupid decisions" that eroded both her wealth and her confidence.
The pattern is devastatingly common. Most founders who exited during the 2021 boom are now three to four years post-exit—exactly when the cracks typically start showing. As Anastasia notes, "We tend to pay for our early mistakes in year five and six."
The timing creates a particularly cruel irony. Right when these founders should be enjoying the fruits of their labor, they're often discovering that their assumed advantages have become hidden liabilities.
From Soviet Collapse to Silicon Valley Success
Anastasia's journey to that nine-figure exit began in an unlikely place: Moscow during the collapse of the Soviet Union. Her parents, university professors and former dissidents, threw themselves into the country's transformation. At just 13, Anastasia was already working as a journalist, reporting for Russian radio from Berlin and Prague.
The early exposure to rapid change and uncertainty shaped her entrepreneurial instincts. "Looking back I realized it was very challenging and dangerous in many ways and hard and there were times when we had to rely on humanitarian aid for food but it didn't matter," she recalls. "At the time it was exciting."
Her path to Silicon Valley wound through law school in Moscow, then NYU for an American law degree, and finally working for American law firms. The pivot to entrepreneurship came through marriage—she joined her husband's startup when he moved from Silicon Valley to open a New York office.
What started as handling legal affairs evolved into co-founding their own company. They experimented extensively before finding product-market fit, eventually becoming one of the early software-as-a-service companies when that model was still novel.
The six-year journey to exit wasn't glamorous. Like classic bootstrappers, they paid themselves "hardly anything" while building the business. Even as they started having children—toddlers aged one and three at the time of exit—they maintained their lean approach.
When a private equity firm finally acquired the company for nine figures, Anastasia found herself with "more money than we knew how to handle." The irony wasn't lost on her that the PE firm later resold the company for much more, making her wonder what potential they'd missed.
The Emotional Earthquake of Sudden Wealth
The immediate aftermath of the exit created an unexpected psychological crisis. While Anastasia was initially too busy with young children and patent litigation from their second company to fully process the change, her husband struggled more immediately with the transition.
"For my husband there was actually harder because he really sold this company and he was obviously involved in kids and other things as well but in a way being less busy maybe harder," she explains.
The social dynamics shifted in uncomfortable ways. Friends didn't know how to behave around them, creating awkwardness even though "for me nothing really changed." The isolation compounded as their social needs evolved in ways they didn't understand.
Research backs up their experience. Studies show that when net worth drops even 10%, our bodies have a physiological response similar to a heart attack—regardless of absolute wealth levels. The psychological impact of sudden wealth can be equally jarring, even when positive.
Unfortunately, the exit's impact on their marriage proved devastating. The combination of sudden wealth, changed social dynamics, and individual processing styles led to divorce. Anastasia is candid about the connection: "I really do think that exit had a lot to do with it."
The divorce wasn't just emotionally painful—it was financially costly. Combined with poor investment decisions, it reduced her net worth from nine figures to "high eight figures." Despite rationally knowing she was still incredibly wealthy, the psychological impact was severe. "For a while I was very stressed," she admits.
The Four Traps That Derail Second Ventures
Through extensive research and interviews with hundreds of post-exit founders, Anastasia identified four primary categories that explain why 70% of second businesses fail. Understanding these patterns can help founders avoid predictable mistakes.
Trap One: Timing Failures The most obvious trap involves starting either too early or too late. Early starters typically jump into new ventures driven by momentum, social pressure, or psychological escape rather than genuine motivation.
"When we jump into a new business like I did, usually for our own reason because we just follow this momentum because everybody else is doing it because we want our founder identity back," Anastasia explains. The problem emerges when motivation inevitably wanes during difficult periods, and the founder questions why they're working so hard when they already have financial freedom.
She witnessed this recently with a friend who invested almost $30 million over six years before finally walking away, admitting he'd lost motivation three years earlier but couldn't face admitting failure.
Late starters face different challenges. After years of comfortable living and chasing experiences, their business skills atrophy and crucial relationships disappear. When they finally feel ready to build again, they've lost competitive advantages they once held.
Trap Two: The Naive Industry Jump Boredom drives many successful founders into completely unfamiliar industries. The excitement of learning something new temporarily masks the reality that they've abandoned all their competitive advantages.
"We get bored and we jump into a completely different industry which we don't understand and for a while it's okay. It's very exciting and then we realize that we have no competitive advantages whatsoever," Anastasia notes.
The combination of overconfidence from previous success and ignorance about new industry dynamics creates a dangerous cocktail. Founders assume their general business skills will transfer, not realizing how much their success depended on deep domain expertise.
Trap Three: Self-Awareness Gaps Successful founders typically develop skills across three functions: creating, operating, and investing. However, they often don't understand which of these represents their natural strength versus learned competency.
"Often times we don't quite know which of these functions we became good at because we had to and which of these functions we are naturally good at," Anastasia explains. This misunderstanding leads to poor partnership choices and role selections in new ventures.
A friend's former business partner crystallized this perfectly, telling him: "You were very very useful in the beginning but you were pretty useless after 3 years because you're so creative that we wouldn't have started this business without you. But then you were kind of annoying later on because you were too creative and I needed to build systems."
Trap Four: Sudden Wealth Syndrome The deepest trap involves psychological and cognitive biases triggered by sudden wealth. Founders become emotionally overwhelmed by their new financial reality, leading to stress, panic, and irrational decision-making.
"We get very emotional about the wealth and we get very stressed about it and we start focusing on it a lot and panicking," Anastasia describes. This emotional state drives hasty decisions, like rushing into new businesses because passive investing feels insufficient for wealth creation.
The irony is that founders who were once rational and methodical become reactive and impulsive precisely when they have the most resources to be patient and strategic.
The Psychology Behind Post-Exit Struggles
The deeper explanation for why founders struggle for an average of 10 years post-exit lies in cognitive dissonance theory. Developed by psychologist Leon Festinger in 1957, this framework explains what happens when reality conflicts with deeply held beliefs and expectations.
Post-exit founders experience "overwhelming cognitive dissonance" as their new reality clashes with fundamental beliefs about success, freedom, and wealth. The psychological discomfort is so intense that most people instinctively try to minimize rather than resolve it.
"We basically go through not just a simple cognitive dissonance but an overwhelming cognitive dissonance where lots of things don't match lots of our ideas don't match the reality," Anastasia explains.
The two primary escape routes both create long-term problems. Some founders jump back into business immediately, telling themselves the psychological discomfort isn't important. Others chase experiences as a reaction against wealth's failure to bring happiness, but this "different kind of consumerism" eventually feels equally empty.
Successful founders learn to embrace paradox instead of seeking oversimplified solutions. They accept conflicting truths: wealth didn't bring happiness but remains valuable and important. Freedom was worth pursuing but requires additional structure to be meaningful.
This nuanced approach allows them to say, "I'm okay with two conflicting truths. I'll reconcile them" rather than swinging to extremes.
The Three Levels of Wealth Development
Understanding wealth as a multi-stage journey helps founders navigate post-exit psychology more effectively. Anastasia identifies three distinct levels that most successful founders eventually traverse.
Level One: Financial Freedom The first stage focuses on creating genuine financial safety. Despite popular assumptions, founders don't automatically achieve this regardless of exit size. Many start pursuing holistic life upgrades before establishing true financial security, creating ongoing stress and anxiety.
"We don't get it regardless how much money we get from our exit," Anastasia notes. The psychological work of confronting money relationships and building systematic financial safety takes dedicated effort.
Level Two: Holistic Life Optimization Once financial security is genuinely established, motivation naturally shifts toward improving health, relationships, and lifestyle. This stage involves the classic post-exit activities: travel, family time, personal development, and exploring previously neglected interests.
However, many founders get stuck here, thinking this comfortable lifestyle represents the ultimate goal. While pleasant, this stage alone doesn't provide long-term fulfillment.
Level Three: Wealth as Purpose Leverage The most fulfilled post-exit founders eventually reach a third level where they use wealth strategically to amplify their contribution to the world. This isn't traditional philanthropy but rather applying their resources toward meaningful problems they're uniquely positioned to solve.
"When we use wealth as leverage for our purpose" represents the culmination of the post-exit journey. However, this typically happens years after the initial exit, requiring founders to complete the earlier stages first.
Rebuilding Life's Foundation After an Exit
Selling a company creates what Anastasia calls a "new kind of P&L"—not profit and loss, but gains and losses across all life areas. Understanding both sides helps founders respond more strategically to their new reality.
What Exits Take Away:
- The business that provided structure and meaning
- Social circles built around the company
- Clear identity and purpose
- Sources of self-esteem and belonging
What Exits Provide:
- Freedom to choose how to spend time
- Financial resources for new opportunities
- Enhanced reputation and credibility
- Energy previously consumed by business demands
The tragedy occurs when founders fail to maximize their gains while systematically addressing their losses. "10, 20, 30 years later, people look back and they say, 'Oh, I had these amazing gifts given to me and I just wasted them,'" Anastasia observes.
The solution requires rebuilding life's foundation using frameworks like Maslow's hierarchy of needs. During the business-building phase, the company satisfied every level of the pyramid: safety, love and belonging, self-esteem, and self-actualization all flowed through the business.
Post-exit, everything collapses simultaneously. Founders must consciously rebuild each level with new sources—a process most find boring but absolutely essential. Skipping this foundation work leads to failures in investments, relationships, and subsequent ventures.
The Baby Bear Approach to Timing
Like Goldilocks seeking the perfect porridge temperature, post-exit founders need to find the right timing for their next major move. Starting too early (Papa Bear) or waiting too long (Mama Bear) both create problems.
The Baby Bear solution involves a three-phase approach:
Phase One: Rest and Recovery First, founders must release the momentum that carried them through their previous venture. Many resist this step, fearing they'll lose their drive permanently. While this risk exists, it's manageable with proper planning.
"I think it's extremely important to let go and just recover and relax and let the emotions do their job," Anastasia advises. This phase allows psychological adjustment and prevents momentum-driven poor decisions.
Phase Two: Experience Expansion Many successful founders built their businesses young and missed broad life experiences. This phase involves deliberately exploring activities, places, and perspectives they never had time for previously.
The goal isn't permanent lifestyle inflation but rather ensuring founders know what options exist beyond business building. Those who skip this phase often return to entrepreneurship simply because "the only thing I know is how to build a business."
Phase Three: Foundation Rebuilding Only after rest and exploration should founders begin reconstructing their basic needs pyramid. This involves developing new sources of safety, belonging, self-esteem, and purpose that don't depend on a single business.
With proper execution, this process typically requires 1-2 years rather than the 10-year struggle most founders experience. The key is approaching it systematically rather than hoping time alone will solve underlying issues.
A Stress-Free Approach to Wealth Management
Anastasia's post-exit financial strategy prioritizes stress reduction over maximum returns. After trying various wealth managers and complex strategies, she simplified her approach around three core principles.
Portfolio Structure:
- 65% relatively liquid, low-risk assets (public equities and cash)
- 25% cash-generating investments (private credit)
- 10% high-growth potential investments (private equity)
Her definition of "relatively liquid" acknowledges behavioral reality: when markets decline, she won't sell equities, making them temporarily illiquid despite technical liquidity. However, her cash-generating assets provide steady income during these periods.
Private Credit Focus: Anastasia's largest holding is Chicago Atlantic, the largest credit organization for the cannabis industry. She specifically seeks investments with zero correlation to equity markets and minimal leverage, generating 16-20% annual returns including equity kickers.
"I only pick things that are completely not correlated with the equity market and use either no leverage, but that's super hard to find. Sometimes low leverage because this is how I make sure it's actually low risk," she explains.
Cash Flow Priority: Rather than fixating on net worth fluctuations, she focuses on reliable cash flow. "Cash flow is so much more important than any theoretical net worth number," she notes. This approach provides psychological stability during market volatility.
The portfolio structure reflects hard-won wisdom about her own behavioral patterns. She learned that being "locked up" in illiquid investments actually helps her avoid impulsive decisions that could damage long-term wealth.
Life Design for High Net Worth Families
Anastasia's current lifestyle reflects deliberate choices about how to deploy her wealth for family happiness rather than status optimization. She spends $650,000 to $1 million annually with three children, splitting time between homes in London and southern France.
Her spending philosophy avoids common post-exit traps. The French beach house, purchased during her early "what else can I buy" phase, has proven valuable for family cohesion but isn't something she'd recommend universally.
"When you have three kids, it's good to have a second home where they all love to go," she explains, while cautioning that "I would never tell anyone that you need to have a second home."
The variable spending range ($350,000 difference) primarily reflects travel decisions. Some years involve more family trips, others focus on local experiences. This flexibility allows lifestyle optimization without rigid budgeting constraints.
Living with "four men in the house" (three sons plus her current husband) creates a high-energy environment that shapes their space and activity choices. The logistics of managing teenagers plus a six-year-old across multiple countries requires significant coordination but provides experiences none of them could access individually.
Finding Purpose Beyond Personal Fulfillment
Fifteen years post-exit, Anastasia has reached what she considers the ultimate stage of post-exit development: using wealth and experience as leverage for meaningful contribution to society.
"When I sold my business, it was all about me me. I felt so much pain from losing that world I loved, losing the relationships, all my basic needs being not satisfied anymore. I was very focused on myself," she reflects. "Today I'm really genuinely driven by how I can give my very very best to the world."
Her current work focuses exclusively on helping other post-exit founders avoid the decade-long struggle she experienced. Through her Post-Exit Playbook program, Post-Exit Academy, and Exit Paradox podcast, she provides the framework and community support she wishes had existed during her own transition.
The mission feels personally urgent because she sees the broader societal cost of talented founders getting stuck in psychological traps. "The society is missing so much because these talented people are stuck in this psychological traps for a decade or more."
Her approach differs from traditional coaching by focusing on predictable patterns rather than individual circumstances. By understanding why 70% of second ventures fail, founders can navigate around common traps rather than learning through painful trial and error.
The work provides the deep fulfillment that eluded her during earlier phases of her post-exit journey. Unlike her failed health tech venture, which she attempted as psychological escape, her current mission emerged from genuine passion developed over years of research and personal experience.
Common Questions
Q: How long does it really take to feel normal again after a major exit?
A: On average 10 years, but it can be reduced to 1-2 years with proper planning and systematic approach to rebuilding life foundations.
Q: Should I start my next company immediately after selling?
A: No. Take time to rest, expand experiences, and rebuild your personal foundation first. 70% of second businesses fail partly due to rushing.
Q: How do I know if I'm naturally creative or operational?
A: Channel focused energy into processing your business experience and ask former partners for honest feedback about your strengths and weaknesses.
Q: What's the biggest mistake post-exit founders make with money?
A: Focusing on net worth instead of cash flow, and trying complex strategies instead of simple, stress-reducing portfolio structures.
Q: Why do I feel empty despite having everything I thought I wanted?
A: Your business previously satisfied all levels of Maslow's hierarchy. You need to consciously rebuild sources of safety, belonging, and purpose outside business.
Conclusion
Anastasia Koroleva's journey from nine-figure success to personal failure and eventual fulfillment reveals the hidden challenges that derail most post-exit founders. Understanding these patterns provides a roadmap for avoiding the decade-long struggle that affects 70% of second-time founders.
The path forward requires patience, systematic planning, and willingness to rebuild life's foundations rather than rushing into the next venture.
