How To Grow Your Startup Without Wrecking Your Marriage

How to leave a senior corporate job, launch a startup, and not kill your marriage is probably the most frequently shared challenge among the members of Punks & Pinstripes. No one likes to talk about it, but scratch the surface of any post-corporate entrepreneur, and it’s universally true. When you leave corporate to build a new venture your spouse becomes your CFO. You’re no longer using the money of a huge corporation. Now, your money is your checking account, your retirement, your home, your kids’ college fund - at least in the beginning. David Sullivan and I both left senior jobs in finance to launch new ventures. And we had to learn a new language to talk about money with our spouses. Our marriages are stronger because of it - but it took a few tries to get it right. (David was COO of Unqork, a $2.5 billion no code platform.) We are hosting a Jam Session on how to navigate your startup and your marriage for 40 people on October 1 at our secret bar in NYC. RSVP here.

Every late-in-life entrepreneur has had this happen: You’re out for dinner talking about how excited you are about your new venture, the people you’re hiring, the product you’re building, the customers you’re winning, how you feel invigorated about work for the first time in a long time. And the only thing coming back is, “But how much will that cost?” Your excitement is your partner’s fear. Your investment is their cost. You want them to feel as excited as you are. They want you to be as cautious as they are. You spend the rest of the dinner trying to find something else to talk about, silently seething that you’re not being heard.

When you leave a corporate job to launch a startup, your spouse becomes your CFO. 

Except now you’re not playing with the money of a billion-dollar corporation that calls profit “EBITDA”. Now your money is your savings, retirement, house, and kids’ college fund. And it’s all at risk if you screw up. At least it feels that way in the beginning. Facts and feelings about money are tangled, messy, and emotional. And a married couple’s conversations about money can become explosive if not handled with care.

Of all the conversations we have among the members of Punks & Pinstripes, how to grow your startup without killing your marriage is the most recurring theme. The statistical evidence shows that entrepreneurs aged 45-55 are consistently more successful than younger entrepreneurs. But the data doesn’t show how hard it is to reconcile your new, entrepreneur life with the marriage that is your rock. By the time you hit your prime entrepreneur age, you’ve grown accustomed to a steady paycheck, healthcare, retirement contributions, professional prestige. And then you threaten to piss it all away because of this inner voice that keeps getting louder: “You need to leave and build your vision right now.” 

There is great advice about how to build a startup. There’s great advice about how to have a happy marriage. But no one likes to talk about how to do both at the same time.

Until now. Let’s dive in. 

(And, if you need more, David and Greg are hosting a Jam Session for 40 people on this topic at our secret speakeasy in NYC on 10/1. RSVP here).  

The economics of being a post-corporate founder are extremely promising

Let’s start with some good news. It’s a logical, sensible, rational economic decision to launch a startup later in your career. The average founder age of the .1% fastest-growing startups is 45. In 2023, the average unicorn startup founder was 52 when they launched their startup. A 59 year old founder has a 300% higher probability of a successful exit than a 25 year old founder. 

When you reach that age you see why older founders outperform. At age 45, you’ve been through some sh*t. You’ve gone through a few cycles of boom, bust, and rebuild. You’ve seen billion dollar problems that no one else sees. You’re less daunted by things that are terrifying to others. You know what problems are best solved by big companies, and what problems aren’t. You’ve built an extended network of people who went through hard things with you and know you’re solid and trustworthy. You have a deep understanding of what you’re uniquely good at (and bad at). You’ve probably already paid off some of your mortgage, saved for college, and funded your retirement.

Equally, the argument for staying stifled by stability becomes flimsier as you get older. We both worked in finance during the financial crisis, and realized that we were perhaps more loyal to them than they were to us. Big is sometimes riskier than small, and takes a huge emotional toll. By the time we were 45 it felt like more of a risk to stay, then to leave. 

There are certain arguments you need to have before you get married (to your startup).

Our significant others are allergic to math and react to spreadsheets like a rat on a subway platform. And they’re (rightfully) concerned about money and want to be informed. It’s taken a long time, and many difficult conversations to align around what numbers matter most. The answer is our checking, college savings, and retirement accounts. There’s a number that we agreed our checking account should never dip below, and a minimum contribution to our retirement and college savings funds that we make each year.

How we hit those numbers is up to us. It took a long time and many tense arguments to figure that out. Have that argument as early as possible. It makes everything easier afterward - especially when it gets scary.

Pivot Responsibly 

Once you know the numbers that matter most, when you’re concerned you might not hit those numbers, you need to talk about it. You should have a pre-mortem of what you’ll do if the startup doesn’t make enough money. How will you supplement your income if you need to? When will you abandon the effort? What resources can you draw on to remain tenacious when you need to? Those moments when you’re running out of money and time, are terrifying. But your odds of survival are better if you’ve planned for the friction ahead of time. 

In it together

On some level, your new entrepreneur life can infuse your marriage with happiness that was never there before. You feel an incredible sense of joy when you know you’re doing the work you were meant to do. And there’s an incredible sense of ownership when you start making real money from it. The new sense of invigoration you feel about work infuses your relationship with new energy.

We are hosting a Jam Session on how to navigate your startup and your marriage for 40 people on October 1 at our secret bar in NYC. RSVP here.