Not tax or legal advice. This article is general information based on my own experience selling a business. Every business and deal is different. Talk with your own CPA, attorney and financial advisor before acting on anything here.
The short answer
Selling isn't the end of something, but it can feel that way if you haven't planned what comes next. Your time, identity and sense of purpose were tied to the business. Plan for them as carefully as you plan the deal. And if part of your price is an earnout, think hard about what your transition year will realistically look like, because the work of being acquired can crowd out the growth that pays it.
Why I sold
After I stopped working nights and weekends and the business became more scalable, I had built the company I set out to build: a real retirement plan and a place where people could build a career. We were making more money than ever, and the excitement started to wear off. I wanted to build the next thing, bigger, and solve real problems for more people.
The transition year, and the earnout lesson
I sold to a private equity buyer and stayed on for a year. My buyer was great, and that year was honestly pleasant. What I didn't see coming: part of my price was an earnout tied to growth, and that year I was busy with everything that changes when you're acquired. New accounting software, a new operating platform, new administrative processes. All necessary, all distracting. Growth paid my earnout, and growth was what I had the least time for.
If you sign an earnout, ask how the buyer's integration plans will affect your ability to hit the targets, and negotiate accordingly. (See what's negotiable besides the price.)
What came next
When the year ended, I got hooked on building software with AI, project after project. I also started investing in angel deals and secondaries: a couple of real winners and a lot of duds, which is how it's supposed to work.
About a year later, I had lunch with Saumil, someone I'd met at an investment club. He had spent two decades in M&A at EY, PwC and large consulting firms. I had just been through a sale as an owner, as a rookie, and I remembered not even knowing who to call when I needed an M&A attorney. We saw a way to bring the whole deal team to owners (accountants, attorneys and advisors) and let technology and AI handle the back-office work, so people can focus on what matters. Selling a business is a high-trust, very human process. That lunch became RealDeal360, and Saumil is my co-founder.
One thing to try this week
Write down what a Monday looks like the week after you sell. Where are you? What are you doing? If the page is blank, that's your first project.
Related questions
This article is for general information only and is not tax, legal, investment or financial advice. RealDeal360 is not your attorney, accountant, tax advisor or investment advisor.