There's a lot of content out there on how to sell a business. What's harder to find is someone who's actually done it, more than once, willing to talk honestly about what the process really feels like from the inside.

That's why we sat down with Alisha M. Pennington, a multi-time exited founder who now runs Exette, where she helps other female founders navigate their own exits. Alisha didn't give us a polished pitch-deck version of the process. She talked candidly about the financial mechanics, sure, but also the identity questions, the grief, and the practical steps that most founders don't think about until they're already mid-negotiation.

Couldn't make it in person? Here's what stood out from our conversation. 

Key highlights from the conversation

Start with your why, and write it down. Before anything else, Alisha pushes founders to name the real reason they're selling. Maybe your heart isn't in it anymore. Maybe you need liquidity now. Maybe you simply want to maximize what you've built. Whatever it is, know it and write it down. It's what keeps you grounded when the process gets hard, and it's what should inform your timeline.

Don't underestimate the emotional weight. Alisha compared selling a business to buying a house, falling in love with it, and then getting the inspection report. For women especially, identity gets tightly bound to the business. She shared that rewriting her email signature to drop "founder" was a bigger moment than she expected.

The reframe: your business is an asset, not your identity. You don't identify as a homeowner; you identify as someone who owns an asset. Alisha's point was that founders can hold their business the same way: something they built and own, not something that defines them.

Not knowing your business's worth is like not tracking your 401k. Get ready before you feel ready. Alisha noted that women in particular tend to wait, often because life gets in the way: caregiving, caretaking, all of it. Her advice: the best time to prepare is before you think you need to.

Earnouts can be liberating and hard at the same time. You lose some of the autonomy you're used to as an entrepreneur. But you also get to focus purely on hitting your performance metrics, which, if you're prepared for the shift, can actually be freeing.

Have specialists in your corner. Specifically, an M&A lawyer, not just general counsel. This is not the moment to save money on expertise; you need people around you who can call BS when it counts.

Final thoughts

A good exit is something you prepare for long before you're ready to admit you're thinking about it. Knowing your why, knowing your number, and having the right people in your corner all take time to get right.

If you're a founder starting to wonder what selling might look like for you, don't wait for the "right" moment to find out. Talk to an expert who can walk you through your options, give you an honest read on where your business stands today, and help you build a plan on your timeline, not someone else's.