I’ve seen it time and again – entrepreneurs building incredible businesses, only to sell them to venture capitalists who extract value rather than create it. I know this pain personally because I sold my own business and joined the 75% of entrepreneurs who regret their decision.
The problem starts with a seductive narrative: grow your company and sell it for millions. But what happens after the champagne stops flowing? Many entrepreneurs discover an uncomfortable truth – they’ve traded their life’s work for a hollow victory.
When I sold my company, I felt disconnected from what I had built. What was once my canvas for creating value became just another corporate entity focused on KPIs and numbers instead of people. The new owners immediately went against my teaching philosophy, promoting ideas like “skip your coffee to save money” – exactly the kind of small thinking I had fought against.
The Value Creation vs. Value Extraction Problem
There’s a fundamental mismatch in our business ecosystem. Entrepreneurs are value creators while venture capitalists are typically value extractors. VCs often use a familiar playbook: they tell you how amazing your business is during courtship, then suddenly you’re “the ugliest girl at the ball” when negotiating price.
After acquisition, many businesses follow a predictable path – services get watered down, prices increase, and the soul of what made the company special evaporates. The original vision gets replaced with spreadsheet-driven decisions that prioritize short-term profits over long-term value.
What’s worse, the entrepreneur who built everything now finds themselves with a pile of cash but no purpose. They go from being an expert in their field to an amateur investor, putting money into markets and assets they don’t understand or control.
Design a Life You Don’t Want to Retire From
My entire philosophy now centers on creating a life you don’t want to retire from. This means:
- Delegate roles, not tasks – give team members autonomy over objectives
- Build a team you genuinely enjoy working with
- Create a vision that’s bigger than your problems
- Take breaks along the way instead of grinding until burnout
When your vision is compelling enough, you’ll handle the inevitable challenges. But when problems outweigh your vision, that’s when you start dreaming of an exit. The key is finding work that aligns with your values and allows you to contribute your unique talents.
After selling my first business, I took time to do comedy. While performing was fun, I felt adrift without a meaningful game to play. That’s why I created Multiplier – a financial education company I never want to sell because it represents my values and vision.
The Hidden Cost of “Success”
Consider what you’re really trading when you sell. Yes, you get a lump sum, but what does it cost you? Freedom? Peace of mind? Control over your life’s work?
Many entrepreneurs who sell end up in a worse position – working harder than ever in a system they don’t control, with values they don’t share, chasing a second payout that may never materialize. I’ve seen dentists sell to corporate practices only to watch patient relationships deteriorate and their promised second buyout become worthless.
Money without purpose is dangerous. It can lead to discontent and even destruction. But when money is a byproduct of living your values and creating value for others, it becomes meaningful.
Instead of focusing on an exit, ask yourself: What could you build that’s truly special? What vision is so compelling you could dedicate your life to it? How can you create an environment where everyone wins – you, your team, and your customers?
That’s the game worth playing. Not extracting every possible dollar, but building something that matters, something you’d be proud to keep nurturing for decades to come.
