Things I Wish I Knew Before Selling My 8+ Figure Company (And What I'm Learning Now)

I wanted to share some reflections on my journey as an entrepreneur, selling my company, and what I’ve learned since. I hope it resonates with anyone building something meaningful or thinking about an exit. Here’s my story and a few hard-earned lessons. My Story I’m a registered nurse who bootstrapped and scaled a home health company from scratch. In just three years, I grew the business to 200 employees and was the sole owner. Last year, I sold the company to a publicly traded corporation. At first, it felt like the ultimate milestone. But after a few months without a daily work routine, I’ve realized selling your business changes a lot—but not everything. Here’s what I wish I knew before the exit and what I’m learning after. 5 Things I Wish I Knew Before Selling My Business 1. Selling doesn’t change who you are. You built your business because you had a vision, a mission, and a relentless drive. Selling doesn’t suddenly switch off that entrepreneurial fire. If anything, you’ll miss the satisfaction of building something meaningful. A sale won’t magically feel like a vacation for life. That drive to build something great will still be there—but it won’t feel the same as creating your first successful company. 2. Learn about C Corps and the QSBS tax exemption. This one’s huge. If you set up your company as a C Corp and hold the equity for more than 5 years, you can potentially save millions by avoiding capital gains tax under the Qualified Small Business Stock (QSBS) rules. I wish someone had told me this earlier—it’s life-changing advice for founders. (I had an LLC sitting around 2 years prior that I used when I started my former company, which I could have made it applied but couldn't due to QSBS rules) 3. Have a clear plan for what’s next. Before selling, get brutally honest with yourself. Why are you selling? What will you do after? Would it make sense to keep growing the company, hire more help, and aim for a higher EBITDA multiplier later? Or are you truly ready to move on? Without a clear plan, the post-sale “freedom” can feel disorienting. 4. Hire more help instead of maxing profits. In hindsight, I should’ve prioritized my mental health and hired a strong leadership team to reduce my day-to-day stress. This would’ve allowed me to take an actual break, recharge, and return with fresh energy. Instead, I focused on staying as profitable as possible, which came at a personal cost - selling the business due to this stressful atmosphere in combination with a nice payout. 5. Selling isn’t the finish line—it’s the start of something new. Make sure you’ve thought about what life after the sale looks like. The “end” of your company is really just the beginning of a new chapter for you. --- 5 Things I’m Learning Now Post-Exit 1. Slow down and embrace the unknown. For years, I was in full-on hustle mode, with every day planned out. Now, I’m learning to enjoy the freedom of not knowing what each day holds. It’s a weird adjustment, but it’s also a chance to rediscover yourself. 2. Find a community of like-minded people. Few people understand what it’s like to build and sell a business. Find a group of other entrepreneurs or post-exit founders who’ve walked a similar path. You’ll need people who get it. 3. Meet as many interesting people as possible. This is my current goal. Building relationships with other curious, ambitious, and thoughtful people is enriching in ways I didn’t expect. 4. Be slow to invest your money. You don’t need to chase maximized returns right out of the gate. Right now, I’m learning to take it slow, develop a thoughtful plan, and steward the proceeds from the sale responsibly. You worked too hard to blow it on risky moves. 5. It’s okay to just be. For years, I was wired to achieve, build, and optimize. Now, I’m learning that it’s okay to pause, reflect, and simply be in the moment. --- I hope this helps anyone thinking about selling or navigating life after an exit. If you’ve gone through something similar, I’d love to hear what you’ve learned! In the meantime, I'm calling this weird phase I am in a "family sabbatical". I'm married with 3 kids, and another on the way. Send me a DM - I love meeting fellow entrepreneurs. Cheers to a great 2025 and thanks for reading.