Why Selling Your Startup Might Not Be the Success You Think

Jan de Vries · 2026-10-19

In the startup world, we're trained to ask certain questions almost on autopilot. How big can this get? How much capital will it take to get there? And eventually, when do I get my money back, and at what multiple? These aren't cynical questions. They're the language of venture capital, where investors put money at risk expecting substantial returns, and founders chase growth, scale, and liquidity. But there's a question we ask far less often: Are we building the companies we actually want to own, or the ones our funding models push us to build? ### When success changes meaning At a recent event, I got talking with seasoned tech entrepreneurs who had already built, scaled, and exited companies. One founder admitted that, knowing what she knows now, she'd never have sold her first company. Another described how differently he's building his next venture after taking outside capital and scaling rapidly the first time around. These were successful entrepreneurs by conventional measures. Yet their experiences had shifted how they thought about ownership, ambition, and what they ultimately wanted from building a business. Their reflections revealed a tension: the decisions that help founders achieve one definition of success can sometimes take them further away from another. In Vienna, the sixth and seventh generations of A.E. Köchert, the former Imperial Court jeweler founded in 1814, offer a strikingly different time horizon. Their focus on craftsmanship, customer relationships, and continuity shows how ownership across generations can shape business priorities. It's a mindset familiar in many multigenerational companies: the determination not to be the last generation. That raises a bigger question: how profoundly does a company's definition of success shape what it builds, protects, and passes on? ### Capital is never just capital For startup founders, choosing a funding model is one of the earliest and most consequential strategic decisions. Venture capital can accelerate international expansion, product development, and market leadership. In sectors where speed and scale are decisive, it can be the difference between building a category leader and being overtaken by competitors. But venture capital comes with an economic logic. Fund lifecycles, return expectations, and portfolio dynamics can influence the growth strategies, financing decisions, and exit opportunities that investors favor. A business that could generate attractive profits for its founder over decades may not deliver the scale or liquidity a venture fund requires. That doesn't make it a bad business. It may simply be the wrong business for that particular capital. The reverse is equally true. A founder determined to retain complete control may underinvest in a market where rapid expansion is essential, sacrificing long-term competitiveness for short-term independence. The real strategic challenge is aligning the company's economics, the investors' expectations, and the founder's ambitions. An investor may favor an acquisition that delivers an attractive return within the fund's investment horizon, while the founder sees greater value in remaining independent. Both can be acting rationally, yet pursuing fundamentally different outcomes. When those interests are aligned, capital can be a powerful accelerator. When they're not, even a growing and successful business can become a source of conflict. ### The ownership decisions that shape your future In his research at Harvard Business School, Noam Wasserman explored a related tension through the founder's "Rich versus King" dilemma: the choices that help build a more valuable company can require founders to surrender ownership and control. But I think the question extends beyond wealth versus control. It's also about time horizon. > "Are we building the companies we actually want to own, or the companies our funding models encourage us to build?" As the EU Inc proposal gains momentum, these questions become even more relevant for European startups. The push for a unified incorporation framework could make it easier to scale across borders, but it also raises the stakes on choosing the right capital partners. Founders need to think carefully about what success means to them—and whether their funding strategy aligns with that vision. Ultimately, selling your startup isn't the only measure of success. Sometimes, the most successful outcome is building a company you're proud to own for decades.