Five Things I Wish I'd Known Sooner About Selling My Company

Amy VanHaren is a founding partner of The Northbound Company, where she helps founders prepare for and navigate their exits. She spent a decade building Pumpspotting, a Maine Venture Fund-backed maternal health company, before selling it, and she's now the exit wingwoman she wishes she'd had. We are excited to welcome Amy back to our newsletter to share more about her new path.

The day I decided it was time to sell my company came about two years late. I began the journey from a place of burnout instead of a place of strength. I knew what we'd built better than anyone, but not how a buyer would see it, and all of that set me up for a very hard road.

I remember the day I saw where I stood. We had just gotten off the phone with a potential buyer we thought would be an ideal fit, woman-led, in maternal health, our technical offering a complement to their physical one, a direct line to the customers they wanted. Yet they passed. I saw all the small decisions I could have made differently over the past few years that would have changed the value they saw in what we were building. What mattered to them was the number of mothers. What we'd built for was the number of employers.

I sold Pumpspotting, the maternal health company I'd built for a decade, in two pieces, over two years. I'm proud of what we built, serving over 100,000 mothers and transforming breastfeeding support in the workplace from NASA to the State of Maine, and yet it wasn't the financial win we'd hoped for, partly because I started too late with too little information.

There is so much support around us for starting a company, growing it, and financing it, yet very little about how to get to the other side.

Here are the five things I wish I'd known sooner.

1. Know the numbers the buyer will care about, and grow those

Most of us track the numbers that tell us how the company is doing, but a buyer is likely looking at different ones.

Most buyers work from EBITDA, your earnings before interest, taxes, depreciation and amortization. Most offers are built on it, so every dollar of profit you add can be worth several dollars at the table.

What I wish I'd known sooner is that EBITDA doesn't move at the eleventh hour. It moves through the ordinary decisions you make over years: what you charge, which customers and product lines actually make money and which ones you've been carrying, the costs that crept in, and how much of the profit depends on you being in it every day. The changes you make this year show up in the number you'll be valued on later.

For a venture-backed company still investing in growth, profit often isn't the number at all. We were building reach, and any buyer we'd end up talking to was going to be a strategic, most likely bringing us in as a bolt-on.

What a strategic buyer wanted to see was mothers, coming in month over month, and proof that they stayed. If I had spent those last two years growing that number instead, I would have walked into every one of those conversations with something they were already looking for.

So the question worth sitting with long before you're ready to sell is who your likely buyers are and what they'd actually be paying for. Once you know that, you know which number to grow.

2. Make friends who will buy you

As my partner at Northbound, Alisa Marie Beyer, says, "Business gets done fast, but only among friends."

I had more than 50 conversations to find the right buyers, and in the end, the ones that got furthest were with people I already knew. We sold the events side of the business to an organization I'd gotten to know years before, and the buyer for our technology came through someone on my team. I knew the people, but I didn't know which lens they'd use to value us, and I hadn't gotten to know the teams and boards around them.

So start now. Make a map of your likely strategic buyers and your dream partners. Reach out, have coffee, and look for small ways to work together that prove your value and build trust.

3. The LOI is not the finish line: it's where it gets harder

I assumed getting to a letter of intent would be the biggest lift. The LOI was where the real work began.

We had one deal fall apart over Thanksgiving. I got the call on a beach in Punta Cana, on vacation with my family, and we had to start over.

Diligence asks more of you than most founders expect. Every financial record, contract, and document has to be in order and accurate, and pulling it together takes real time from you and your team, all while you're still running the business.

What I wish I'd done sooner is decide what I wanted before I ever signed an LOI. That means knowing the deal structure that works for you, whether you'll stay on or step away, and the numbers you need to walk away with.

4. Get ready for the day after

The deal wasn't the hardest part. The hardest part was figuring out who I was once it was done.

I'd built for nearly a decade and spent almost two years on the exit, and it closed with a whisper, not the bang I'd dreamed of. I expected relief and joy, and what I felt first was the empty space where the company used to be. I swung between pride and loss, regret and excitement.

Whether your company feels like part of who you are or simply the thing you've spent years building, selling it will stir something up. Know what enough looks like for you financially, so you recognize a good outcome when it's in front of you. Picture what your days will look like once the business isn't filling them, and give yourself a season before jumping into the next big thing.

Looking back, if I had been truly honest with myself during those two years, I might have accepted what we'd built and wound it down, instead of pushing myself toward an exit that took so much out of me. A sale isn't the only good ending, and it helps to know that before you're in the middle of one.

It took two years to sell. It also gave me two years to make peace with my ending.

5. Don't go it alone

Selling a company takes a team, and who's on it matters more than I understood at the start. You need people who can run a strong process and get the best outcome for the business: advisors who have been through an exit themselves, the right bankers or brokers, a good attorney, and a board that's with you.

Early on, I brought in brokers who didn't know how to tell the story of what we'd built to the strategic buyers we were talking to, and it cost us time and money.

Our board and our investors at Maine Venture Fund stood with us through the whole process. Alisa, who was our fractional COO for several years and had been through exits herself, kept me grounded and clear-headed through the toughest stretch. And for myself, I hired a friend to sit on Zoom with me through all the technical hand-offs and transitions.

Build that team before you need it. And make sure at least one person on it is there for you, not the deal.

Getting to the other side

I know this road from the inside, and I've become the exit wingwoman I wish I'd had.

Alisa and I started The Northbound Company to help founders and owners, especially women, prepare earlier, navigate the exit journey, and walk away with the wealth they've earned for themselves and their stakeholders. We're founder-operators, and between us we've been through seven kinds of exits, including some that didn't go the way we hoped.

We focus on women because they often carry more into this process and walk away with less. One UK study found that women exit their businesses for 25 percent less than men on average.

We talk about starting and scaling all the time. We rarely talk about how it ends. I'm out to change that, so we can change the outcomes.

Great exits don't happen by accident. They're architected.