Selling your business is a major life decision and the questions you ask early can shape the entire journey. Here’s what most sellers ask first and what they should be asking instead:

If you’re thinking about selling your software business, knowing what the typical sale process looks like can make the journey a lot less overwhelming. Here’s the path I walk with every founder, from the first conversation to closing day:

Every founder eventually faces the decision: keep building or sell and start a new chapter. If you’re starting to think about selling, the right buyer matters just as much as the right offer. Here’s what I’ve learned from being on both sides of the table:

Most buyers talk about growth, alignment, and care for your team. But if you’re a founder selling your company, what really matters is who’s actually going to run it—and what they’ve done before. Here’s why I operate differently than Private Equity, Strategic buyers, or traditional search funds:

Anyone can look good when a deal is clean and things are going well. But how do they show up when something breaks, a customer churns, or a team member leaves? Here’s what I’ve learned about evaluating a buyer, especially when the pressure’s on:

Not all offers are created equal. Cash, equity, earnouts, and debt all shape how you get paid, how much risk you carry, and what your future looks like. Here’s how I suggest sellers think about deal structure beyond just valuation:

Most founders picture the day after selling their business as a clean break. But what actually happens when the emails stop, the decisions aren’t yours, and the pressure lifts? Here’s what I’ve learned about that space and how to make the most of it:

Most founders obsess over valuation and then get surprised when post-sale life feels off. The truth? The real mistake happens earlier: not understanding the buyer, the deal dynamic, or what really matters in the long run. Here are the common pitfalls and how to avoid them:

Every owner/CEO I’ve talked to after selling their company says the same thing: “I wish I had known how much of a journey it would be.” Here’s what I’ve learned from those conversations and what I’d tell any founder who’s considering a sale:

Most sellers focus on the deal itself. But what happens after it closes? Who’s leading the company? How do you stay involved? What does that relationship look like? Here’s what I commit to when I acquire a business and how I work with founders post-sale:

After selling SuperSalon, I didn’t step away, I joined the acquiring company. I wish I had asked deeper questions so I could’ve stepped into that next chapter with more clarity. Here’s what every founder should think through before closing: