Every business you build is a family business
Our thoughts on how to thrive at both.
[A Couple Minutes] Press play to hear a few minutes about our week, financial news, and the inspiration for this week’s newsletter. Let us know what you think!
Hi, Doug again.
In our upcoming book, we have a chapter that explores the intersection of entrepreneurship and relationships. It's a place where big dreams collide with big love, and I can tell you from personal experience, it's not always a smooth ride. Running a business while meeting the needs of your family can feel like carrying a torch and a lantern at the same time: both need your focus, both are mission critical, and dropping either feels completely unacceptable. So, how do you keep burning it on all ends?
Becoming an entrepreneur, you tend to fall down a bit of a rabbit hole. It’s very easy to become obsessed with your business, working through the weekend, muting your group chats, and saying "no" to friends because you’re convinced that there’s too much to do. It's not arrogance—it's focus. But being so focused can turn you inward very easily. That looks like skipping date nights to relax at home instead of connecting with your partner or missing your kid’s softball game to answer some not-so-urgent e-mails. You start acting like you’re the main character in every story, and the people you love begin to feel like support staff. All the while, you’re lonely as hell.
Before we started officially working together, Heather can tell you how many business decisions and client interactions I’d run by her in a given week. I always thanked her for her help, but on top of her own corporate law job and everything for the girls, my work was burning her out. Gratitude couldn’t make up for how much she was sacrificing for my dream. I regret ever making her feel that what I was building was more important that what she was doing. I wasn't trying to be selfish; it simply came with the territory.
Entrepreneurship often demands intensity, especially in the early years and when make-or-break moments arise. But these moments are slippery and risk straining the very relationships that keep you grounded.
At the same time, you're not just building a business: you're building a life. Every stale cup of coffee, every risk, every dollar you pour into your venture is, at its core, about creating something that endures for your family. Maybe it's financial security, a legacy, or just the freedom to live on your terms. That's the entrepreneur's paradox: the same drive that pulls you inward is fueled by love for the people you're doing it for. You want to give your partner and kids a future; theoretically, one with less constraints than if you did things the corporate way.
But here's the catch: your family can’t feel that future if they're not part of your present. If you're always "on" for the business, your partner might start wondering if they're second fiddle. Kids notice, too. My daughters don't care about how many clients signed up this month. They just want me at their dance recitals and at the bus stop and on the couch watching SpongeBob after dinner.
Chasing your business dreams without sidelining your family isn’t about finding the perfect balance (that doesn't exist). It's about intentional choices that honor both your goals and your loved ones.
Here’s what works for us these days.
Set immovable priorities. Entrepreneurship comes with periods of intensity: product launches, new business partners, or that one client who needs everything yesterday. Those sprints are real, and your partner has to accept that. But you also need non-negotiable moments that say, "You come first." Heather and I have this longstanding ritual: Friday night sushi on the couch. It's our time to connect, laugh, decompress from the week, and catch up on our favorite shows. Maybe for you, it's a weekly coffee date, a movie night with your kids, or never, ever missing a holiday no matter what. Pick one or two things that are sacred and stick to them like they're a deadline for your number one client.
Communicate the why. Your partner isn't a mind reader. If you’re at or approaching a time of peak intensity, explain why this moment matters for the business and your family's future. Share the vision: maybe it's paying off debt, funding the kid’s college plans, or upgrading your house. When your partner sees the bigger picture, they’re more likely to cheer you on, even if you’re temporarily a little absent. Be honest about the intensity periods, too. Say, "This month is nuts, but by June, I'll have come up for air. Let’s put some dates on the calendar now so we have something to look forward to." Transparency builds trust and limits resentment. This works with the kids, too.
Create small moments of connection. You don't need to make grand gestures to show your family they matter. Small, consistent acts go a long way. For example, I love walking my kids to school. We all get a chance to connect and start the day off right. And on the walk home, when Heather joins us, we both get to level set and map out our days before we get to work. These moments cut through the loneliness of entrepreneurship and remind your family they're in your heart, even when you're in the weeds.
Acknowledge that your ambition is collective. Entrepreneurship is a team sport, even if only one of you is the founder. You need to acknowledge what your partner's giving up: time, energy, maybe their own dreams for a bit, to support you. They need to have their voice heard, too. Is there something they’ve always wanted to do that your career is preventing them from doing? You need to talk about that. There is a world where you might need to throttle down your own work to create the space for them to accomplish what they want to. This is one of those tough moments supporting our point that an investment in one thing is oftentimes a sacrifice in another.
In Money Together, we dive deeper into stories of couples who've faced these tensions head-on, from founders staring down financial uncertainty to partners who've learned to see risk as an opportunity. But right now, you can pick an immovable priority this very week—a dinner, a walk, a no-work-talk night—and commit to it.
Do you have a story about balancing your hustle with your home life? We’d love to hear it.
If you listened to this week’s A Couple Minutes, you already know our kids have been off for what has to be the longest Memorial Day Weekend ever. Six days. Six WHOLE days! I am not sure whose idea it was add three unused snow days to MDW, but whoever it is, you’re on my s—t list. Just end the school year a few days earlier. This isn’t hard. Okay, rant over.
The good news is that we did a fantastic job of staying busy and having fun. We trekked down to the Jersey Shore for a few nights (as one does) and enjoyed much better weather than expected. There was some beach, a pool, hibachi, and lots of ice cream! But no shore weekend is complete without a round of family mini golf at Congo Falls. As you can see, I not only shot par, but I dismantled my entire family in the process. They were very happy for me.
TJA in the news
Over at Investopedia, I wrote about how millennials can optimize their their savings strategies for retirement.
I then made my regular appearance on CNBC’s World Wide Exchange to talk bitcoin, Trump’s tax bill, and this year’s market volatility. Also for CNBC, I shared some evergreen advice on how to approach investing in new technologies (like robotaxis). Check them out!
Shameless plugs
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And don’t forget, our forthcoming book, Money Together: How to find fairness in your relationship and become an unstoppable financial team, arrives in October 2025. You can pre-order your copy now!
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The content shared in The Joint Account does not constitute financial, legal, or any other professional advice. Readers should consult with their respective professionals for specific advice tailored to their situation.
I deeply relate to this post, thank you for sharing. I grew up in a family of entrepreneurs and now run a business with my husband. It’s hard! I appreciate the advice for staying grounded.