Why Selling Your Startup Might Not Be the Success You Think

Jan de Vries · 2026-10-19

In the startup world, founders and investors learn to ask certain questions almost instinctively. How big can this become? How much capital will it take to get there? And, sooner or later, when do I get my money back, and at what multiple? These aren't cynical questions. They reflect the logic of venture capital, where investors put capital at risk expecting substantial returns and founders pursue growth, scale, and eventually liquidity. But there's a question we ask far less often: Are we building the companies we actually want to own, or the companies our funding models encourage us to build? ### When Success Changes Meaning At an event recently, I found myself in a conversation with experienced tech entrepreneurs who had already built, scaled, and exited companies. One founder told the room that, knowing what she knows today, she would never have sold her first company. Another described how differently he is building his next venture after taking external capital and scaling rapidly the first time around. These were successful entrepreneurs by conventional measures. Yet their experiences had changed how they thought about ownership, ambition, and what they ultimately wanted from building a business. Their reflections revealed an interesting 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 illustrates 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. It raises a broader 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 also 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 necessarily 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 aren't, 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. As one founder put it: "I wish I had asked myself not just how much I could sell for, but what I actually wanted to build and why." When you're considering your next funding round or an acquisition offer, take a step back. Ask yourself: - What does success look like for me in 10 or 20 years? - Am I optimizing for a quick exit or for long-term ownership? - Do my investors' time horizons match my own? - What would I build if I never planned to sell? There's no single right answer. But being intentional about the kind of company you're building—and why—can save you from a success that feels like a loss.