Entrepreneurial Marriages

Happy Thursday!

Lets talk about significant others + business today. They make our lives immeasurably better, and we couldn’t launch or grow businesses without their support.

I’ve been reflecting on the single conversation that saved both my business and marriage 7 years ago. And I don’t mean to say we were about to divorce - it wasn’t anything that drastic. But it set us up for success that completely changed the dynamic between us.

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By the end of this email, I'll share the exact 3-question framework that transformed our entrepreneurial partnership - the same one that's helped dozens of founder couples avoid the silent marriage-killer affecting 78% of entrepreneurial relationships.

In our 17 years together, Jessie and I have launched businesses, moved across states, sold everything (twice!), and raised four kids through it all. We've been talking a lot lately about this wild ride we've been on, and I realized some of these insights are too valuable not to share.

The Scary Truth About Entrepreneurial Marriages

Let's get real. Entrepreneurs are about 10% more likely to divorce than couples with traditional jobs. The unpredictable income. The emotional rollercoaster. The mental absence even when physically present.

The scariest part for us was never knowing where next month's mortgage payment would come from. Those nights staring at the ceiling wondering if we'd make it aren't romantic. They're freaking terrifying. And they're shared by pretty much every entrepreneurial couple I know.

Back when we opened our first phone repair shop, we were scrambling for solutions. We had a six-month-old baby and needed income fast. Our brilliant solution? A hastily constructed drywall partition in the back of the store. We'd meet customers up front, then duck behind the wall to change a diaper between fixing cracked iPhone screens. Jessie would work shifts with the baby back there while I hustled for more business. Total chaos, but that store had to work because it was our only source of income. Talk about pressure!

Then there was that brutal 18-month stretch with another venture that never materialized. We were selling rental properties just to cover our mortgage. In retrospect, I should've known a business where I didn't have full say was a toxic setup, but we were all-in. Those were the times when the entrepreneurial path felt less like a choice and more like a trap.

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Trust: The Foundation Everything Builds On

Looking back, what amazes me is Jessie's unwavering belief that we'd figure it out. Not blind faith, but trust built through consistent actions. Working multiple jobs in college. Buying our first house when we were making $2.13/hour waiting tables. Showing up and grinding even when results weren't immediate.

For entrepreneurial couples, this trust is EVERYTHING because there will be seasons where you have to look at each other and say, "I don't know how, but we'll make this work." And mean it.

When I asked Jessie where that confidence came from, especially since we met as teenagers and married at 21, her answer was simple but profound. She said it was watching my work ethic in those early days. Not just my entrepreneurial excitement, but the follow-through. Like when we bought our first house seven months after getting married while still in college. Or working at the county jail while maintaining a full course load and a side hustle.

She could tell the difference between entrepreneurial daydreaming and actual execution. It's a distinction that matters! When I later proposed the phone repair business after seeing a kid fix a phone on campus, she backed me completely. Not because the business was guaranteed to succeed, but because she'd seen me put in the work before.

IF YOU WANT YOUR SPOUSE TO TRUST YOU, YOU CAN WARRANT THAT TRUST BY TAKING ACTION.

The Reality of Entrepreneurial FOMO

We've both had those moments looking at friends with normal jobs. Those steady paychecks. Those predictable hours. Those acual benefits. Who wouldn't occasionally wish for that stability?

But we've realized something profound over the years: you'll regret not going for it WAY more than you'll regret the struggle of doing it. That's the entrepreneurial mindset. Having a partner who gets that is pure gold.

Jessie gets envious sometimes of friends whose husbands have those corporate gigs with predictable monthly income. It's not about the money exactly - it's about knowing exactly what's coming in. The last time we had the same income two months in a row was back in 2017 during the LCDcycle days. Since then, it's been feast or famine. Fat quarterly distributions from one company paying for everything, then months of hustle.

Speaking of LCDcycle, the whole reason that business was successful is because I hired x3 overseas salespeople. My friend Nick’s company can help you do the same here.

I get jealous of those people too! But here's the trade-off those steady jobs often come with: schedules that aren't great and limited freedom. Most of our friends are also 6-10 years older than us, so they're in a different phase of their careers. That perspective helps when comparison starts creeping in.

Creating Boundaries That Work

One thing research consistently shows is that entrepreneurial couples need what experts call "privacy set-asides" - intentional time apart to recharge.

In our marriage, Saturday date nights are non-negotiable. We go to bed at the same time every night. And I'm learning to leave my laptop in the office rather than carrying it around the house like it's a freaking extension of my arm.

These boundaries didn't happen naturally. We created them deliberately after realizing how easily entrepreneurship consumes everything.

Some of our best memories came during forced breaks from business. Like the six months we spent in Houston for our daughter's lung transplant where I worked remotely. Or that incredible summer when we visited all 50 states with nothing but a T-Mobile hotspot for occasional work check-ins. Best. Decision. Ever! Those weren't just vacations - they were perspective shifts that made both our marriage and my businesses stronger.

Jessie rates me a 6 out of 10 at compartmentalizing work stress. Not terrible, but definitely room for improvement. I struggle with this. When something stressful happens at work, I find it nearly impossible to just flip a switch and be fully present at home. Talking about it sometimes makes it feel more real to me, not less. But I'm learning that short-term discomfort in addressing issues head-on creates long-term peace for both of us.

The 3-Question Framework That Saved Our Marriage

This framework emerged during our darkest period - 18 months with no income, selling rental properties just to pay the mortgage. I was physically present at home but mentally in my business 24/7.

One night at our kitchen table, after another failed investor meeting, we had the conversation that changed everything. Three simple questions became our lifeline:

1. "What are you optimizing for?" Not just in business, but in life. Fame? Fortune? Freedom? Family? Getting clear stopped me from chasing contradictory goals and helped us align on what actually mattered.

2. "What does success cost?" Not in dollars, but in life currency. What are we willing to sacrifice, and what's non-negotiable? This created our first real boundaries.

3. "How will we know we're winning together?" The game-changer! We realized we were using different scorecards for success. Once we created a shared definition of winning, everything changed.

These questions led to our first "Partnership Agreement" - not a legal document, but a real commitment to how we'd run our entrepreneurial marriae. Seven years later, we still revisit it quarterly.

The transformation was immediate. Our communication improved. The same cyclical arguments disappeared. I became more effective in my business because I wasn't constantly justifying my choices. And most importantly, we found joy in the journey together again. Life-changing stuff!

The Entrepreneur Marriage Playbook: How to Win Together!

To make this super practical, here's the framework we've developed after helping dozens of entrepreneurial couples transform their relationships:

Four Power Moves for a Rock-Solid Partnership

1. GET CLEAR: Know What You Both Want

• Write down your big dreams together (beyond just business)

• Pick 3-5 things you'll never compromise on

• Check in every few months to make sure you're still aligned

2. TALK SMART: Stay Connected (For Real)

• Every day: 10 minutes of no-phone talk time

• Every week: Half-hour chat about how business affects home life

• Every three months: Big-picture check-in on your partnership

3. BUILD WALLS: Protect Your Marriage Zone

• Create no-work spaces in your home

• Set firm work hours (and stick to them!)

• Ban business talk during special times (date nights, family dinners)

4. CELEBRATE EVERYTHING: Cheer for Each Other

• Throw mini-parties for wins in BOTH business and marriage

• Create a bounce-back ritual for when things go wrong

• Point out when your partner grows (not just when the business does)

Red Flags That Scream "Fix This Now!"

When these pop up, it's time to pause and reset:

1. Business talk takes over more than 4 out of 10 conversations

2. Date nights keep getting canceled for "important" business stuff

3. You feel bitter about who's giving up more

Try it this week. Set aside 30 minutes with your spouse. Ask those three questions and start building your own Partnership Agreement.

I am so freaking grateful for my rockstar wife and her unwavering trust! I couldn’t do any of this without her.

Chris

You can listen to the actual interview with my wife here: YouTube (will be live on YT in a day or two) - Apple Podcasts - Spotify - Other Podcasts