The sale closed three weeks ago. The calendar, once packed with board meetings, product reviews, and investor calls, sits empty. The Slack channels that demanded attention every waking hour have gone quiet. The phone is still checked reflexively before the reminder hits - nothing urgent is waiting.
Relief was supposed to come. Maybe euphoria. Instead, there's something unexpected and hard to name.
Research on founder exits tells a counterintuitive story. The emotional aftermath rarely matches the financial outcome. Most people who achieve what entrepreneurs dream about don't feel better for it. The money lands. The satisfaction doesn't.
Nobody mentions this at the closing dinner.
What comes next varies wildly, but patterns exist. Most founders stumble through the first year or two, testing things that don't fit, before finding their footing. The pressure to have an immediate answer makes it worse. Investors move on to their next deal. The former team is navigating the acquisition. Everyone assumes the newly liquid founder is off living their best life.
The expectation is happiness. The reality is often a hard question: what the hell comes next?
Six Paths People Take
After talking to dozens of post-exit founders and digging into the research, six distinct paths emerge. Most founders try more than one before settling somewhere. Some combine several into a portfolio approach. None is inherently better.
1. Angel and Venture Investing
The most common first move. Founders know startups, have capital, and other founders want their money and their network. What could go wrong?
A lot, actually.
A 2007 study by Robert Wiltbank and Warren Boeker found that 52% of angel investments fail to return the initial capital. The average return was 2.6x over 3.5 years, but that average obscures enormous variance. A handful of big winners carry portfolios; most individual bets lose.
The operator-to-investor transition trips up most founders because the skills are fundamentally different. Running a company requires deep involvement, rapid decision-making, and constant course-correction. Investing requires patience, portfolio thinking, and the discipline to write a check and step back. Naval Ravikant built AngelList and invested in over 200 companies, including Uber and Twitter, but he had the advantage of seeing thousands of deals before deploying serious capital. Most first-time angels don't have that context.
The trap is assuming that success as an operator translates directly to success as an investor. It doesn't. The pattern recognition that helped build a company can work against a new investor. Every pitch deck is a version of the founder's own journey, leading to overvaluing founders who seem familiar and missing those who don't fit the mental model.
After the Slack sale, Stewart Butterfield was direct about his intentions: "I'm not going to do anything entrepreneurial." Yet even he has since engaged in selective angel investing, focused on workplace tools and collaboration software where his expertise runs deep.
For those drawn to this path, starting small makes sense. Modest checks in the first year. Joining an angel group to learn from experienced investors. Treating early investments as tuition, not portfolio construction. And being honest about whether the work itself is enjoyable or just the idea of it.
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2. Board Seats and Advisory Roles
This path offers something many founders miss after exit: a reason to show up. Board meetings, strategy sessions, a team that values input. It scratches the itch without demanding the all-consuming commitment of building.
Independent board roles typically require significant prior experience. Companies usually need independent directors when they approach an IPO or sale, not earlier. Advisory roles are more accessible. Three or four early-stage companies, trading expertise for equity and a regular reason to engage.
Compensation varies widely. Independent directors at public companies might receive $200,000 to $400,000 annually in cash and equity. Private company boards pay less but can include meaningful equity upside. Advisory arrangements typically involve 0.1% to 0.5% equity, depending on the stage and level of involvement.
The danger is underestimating the commitment. A board seat at a growing company demands real attention, and multiple board seats can become a full-time job in disguise. One or two meaningful engagements beat five superficial ones.
Some founders discover advisory work feels hollow. The problems aren't really theirs. They give advice. Someone else decides whether to take it. For people used to making the call, watching from the sideline can feel like slowly starving.
3. Acquiring Businesses
Build one company. Buy another. Apply what was learned.
Entrepreneurship through acquisition has exploded. Stanford's 2024 Search Fund Study reported a record 94 new search funds launched, with an overall IRR of 35.1% and ROI of 4.5x. The model works: buy a company with proven cash flows, apply professional management, and create value through operational improvements rather than product-market risk.
For founders who miss operating but don't want to start from zero, acquisition offers a middle path. Day-one revenue, an existing team, and problems to solve immediately. The learning curve involves managing an established organisation rather than building one from scratch. Different skill set, but often a natural extension of what operators already know.
The "silver tsunami" of retiring baby boomers creates ongoing deal flow. A significant majority of privately held businesses are owned by boomers, many of whom need succession solutions. For those who enjoyed the operational challenges of the last company more than the fundraising and product discovery, this path might fit.
Target companies typically range from $5 million to $50 million in enterprise value, requiring $2 million to $10 million in equity capital alongside debt financing. Traditional search funds raise $400,000 to $500,000 to cover the search period. Self-funded searchers use their own capital and take on personal guarantees in exchange for larger ownership stakes.
But the search process demands patience. Stanford's data shows a median search time of 23 months. That's years of sourcing and diligence before finding the right target. Not everyone has the temperament for it.
To learn more about this path, read The Entrepreneur's Acquisition Playbook.
4. Starting Again
Jyoti Bansal sold AppDynamics to Cisco for $3.7 billion in January 2017, the day before the company was supposed to go public. He took six months off, travelled, and worked through his bucket list.
"In six months, my bucket list was done," he told CNBC. "What I realised is that building companies is what I enjoy."
Nine months after the sale, he started Harness. He also founded BIG Labs, a startup studio, and co-founded Unusual Ventures, an early-stage investment firm. Later came Traceable, a security company. In 2025, Harness and Traceable merged into a company valued at roughly $5 billion. His investor at Menlo Ventures compared him to Elon Musk, though noted he's "not super weird, or extreme."
Bansal is a rare case. Founders who build back-to-back unicorns can probably be counted on two hands. Lew Cirne sold Wily for $375 million and then founded New Relic, now worth over $4 billion. Auren Hoffman sold LiveRamp for $310 million, watched it IPO at a $4 billion+ valuation, then built SafeGraph to hundreds of millions in value.
The serial founder path works for people who genuinely love the early chaos of building. Not everyone does. Some founders romanticise the startup phase until they're back in it, grinding through the same problems they thought they'd escaped. If exit felt like liberation from operational stress, starting fresh might recreate the trap.
There's a darker version of this path: starting again because the silence can't be tolerated. Jumping immediately into another company without processing what happened often means running from something rather than toward it. The distinction matters. Running toward a genuine opportunity creates energy. Running from an identity void leads to exhaustion and, frequently, failure.
5. Stepping Back Entirely
Stewart Butterfield, who co-founded both Flickr and Slack, announced his departure from Salesforce (which acquired Slack for $28 billion) in late 2022. In a message to employees, he wrote: "I fantasise about gardening. So, I'm going to work on some personal projects, focus on health, and try to learn as many new things as I can."
He and his wife subsequently purchased significant real estate, including designer Tom Ford's ranch. Reports suggest he's focused on family, philanthropy, and creative projects. He remains engaged intellectually but hasn't launched another company.
Stepping back sounds simple. It isn't. The void hits hard.
A French founder named Louis Debouzy launched "The Exit Club" in 2023 after experiencing severe anxiety following his own exit. Within five months, 200 founders had joined. Most were showing symptoms of depression. "People say: 'I don't understand, you have everything you need, you have money, a family, you're happy.' But there is real pain there," he told Sifted.
Markus Persson created Minecraft, sold it to Microsoft for $2.5 billion in 2014, and was publicly candid about struggling with the aftermath. The creator of something loved by hundreds of millions of people found that financial freedom didn't translate to happiness.
The risk with complete withdrawal is losing structure and purpose simultaneously. Some founders thrive with unscheduled time. Many don't. For those considering this path, building some scaffolding first helps: a weekly routine, ongoing commitments that provide accountability, community of people who understand the transition.
6. Philanthropy and Impact
MacKenzie Scott has given away over $26.3 billion since 2019. Her approach involves unrestricted grants to nonprofits working on systemic issues. She signed the Giving Pledge, committing to donate the majority of her wealth during her lifetime, and in 2025 alone announced $7.1 billion in donations to roughly 225 organisations.
Her methodology is distinctive: trust-based philanthropy with no strings attached. Organisations receive large grants and decide for themselves how to deploy the funds. This contrasts with the more common model of restricted giving with extensive reporting requirements. Whether one approach is more effective remains debated, but Scott's scale is undeniable.
Philanthropy at this level isn't accessible to most founders. But the underlying impulse—applying resources and skills toward problems that matter—works at any scale. Funding local organisations, joining nonprofit boards, and dedicating time to causes that matter.
The key is intentionality. Philanthropy done well requires the same rigour applied to building businesses. Throwing money at problems feels good momentarily, but often accomplishes little. For those serious about this path, investing time in understanding the ecosystems matters. Learning what works and what doesn't. Treating impact like a product worth building.
How to Think About Choosing
Choosing a path isn't about finding the objectively best option. It's about finding the one that fits who someone actually is, not who they think they should be.
Start with an honest assessment of what created energy in the previous role. Was it the early chaos of building something from nothing? The operational complexity of running at scale? The strategic thinking at the board level? The moments of helping a struggling team member figure something out? Different answers point toward different paths.
Risk tolerance matters. After an exit, many founders become more conservative. They've seen firsthand how much can go wrong and have something to lose now. Others find that financial security makes them more willing to take swings. Neither approach is wrong, but risk tolerance should inform direction.
Time horizon matters too. Some paths demand multi-year commitments. Starting a company or acquiring one locks someone in. Advisory work and investing offer more flexibility. Uncertainty about what's wanted suggests favouring optionality.
And partners deserve a say in the conversation. The last company probably had strained relationships. Whatever comes next will have its own demands. The people closest to a founder deserve input on decisions that affect them.
Testing Without Over-Committing
Most founders take two to three years to find their footing post-exit. The mistake is jumping into a major commitment before knowing what's actually wanted.
Treat the first year as exploration. Curious about investing? Make a few small angel checks and see how the work feels. Interested in boards? Take an advisory role first and test whether the dynamic is satisfying. Thinking about starting again? Spend time on the idea before raising money or hiring.
Some founders find that a portfolio approach works permanently. Sitting on one or two boards, making occasional investments, advising a handful of companies, dedicating time to philanthropic work. No single activity defines them, but the combination provides variety and purpose.
Others need the focus of a singular pursuit. The portfolio approach feels scattered. Only the individual can determine their type, and that determination might take longer than expected.
Identity Question
Underneath the practical questions about what to do next lies a harder one: who is someone without their company?
For years, identity was intertwined with the business. When someone asked what they did, the answer was obvious. Now that identity has been severed, and the question of what someone "does" has no clean answer.
A thoughtful piece on A Smart Bear describes the phenomenon: "Almost all startup founders experience a deep and prolonged sadness after selling their company, even when the sale is an outrageous success." The author compares it to post-Olympic depression—the emotional crash athletes experience after years of singular focus culminate in a finite event.
Research consistently shows entrepreneurs face elevated rates of mental health challenges. The post-exit period can intensify existing vulnerabilities.
Don't skip this work. Before deciding what to do, it might be necessary to determine who someone is becoming. Therapy helps. So does time with people who understand the transition. The Exit Club and similar peer groups exist for a reason.
Geographic Considerations
Location affects what paths are practical. Silicon Valley offers dense networks for investing and starting companies, but comes with a particular intensity that some founders want to escape post-exit. Smaller ecosystems might lack deal flow but offer different qualities of life.
Geographic arbitrage becomes possible with liquidity. Moving to a lower-cost-of-living area, better tax treatment, or simply an environment more aligned with the desired life becomes an option. Several founders have relocated internationally after exit, using the transition as an opportunity to redesign everything.
For board or advisory work, proximity to target companies matters less than it used to, but it still matters. Remote board service is possible but not equivalent to in-person engagement.
Timeline Reality
Year one is often harder than expected. The adrenaline fades, the calendar empties, and the identity questions surface. A period of disorientation lasting six to twelve months is common before any direction starts to emerge.
Year two typically involves experimentation. Trying things, some of which work and some of which don't. Investments that seemed exciting lose their appeal. Advisory relationships that started well fizzle. A seemingly certain company idea reveals fatal flaws.
By year three, most founders have a clearer sense of their direction. Not necessarily a final answer, but a working hypothesis about what the next chapter looks like.
Those who fare best tend to share certain characteristics: they maintain relationships that aren't dependent on their company, have interests outside of work, and engage in some form of reflection on what the exit means. Those who struggle tend to have over-indexed on the company as their primary source of identity and community.
Questions Worth Sitting With
Before committing to any path:
What actually created energy during the company-building years? Not what produced results or earned praise, but what felt genuinely satisfying day to day.
What's the pull toward the next thing—genuine interest or avoidance of something uncomfortable?
How much self-worth is tied to professional achievement? If the answer is "most of it," that's worth examining before major decisions.
What do the people closest see? Their perspectives often reveal blind spots.
What would feel like regret in five years? Sometimes the fear of regret points more clearly toward the right path than analysis.
How does the ideal three-years-from-now feel? Not what's been accomplished, but what emotional state is inhabited.
Way Forward
There's no formula for what comes after exit. The six paths here are starting points, not prescriptions. Most journeys will touch several of them and may eventually land somewhere unmapped.
The pressure to have it figured out immediately is misguided. Founders who handle this transition well give themselves permission to not know for a while. They experiment, fail at some things, and discover unexpected interests. They trust clarity will come.
They also recognise that the skills that made them successful as operators don't automatically transfer to other domains. Humility matters. So does curiosity. The founders who struggle are often those who assume previous success has equipped them for anything.
Clarity usually does come.
Just not as quickly as anyone wants.
I write when there’s something worth sharing — playbooks, signals, and patterns I’m seeing among founders building, exiting, and managing real capital.
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