The Startup of Marriage: Why Founding a Company is Just Like Saying "I Do"

This past month, I officiated my cousin’s wedding, marking my debut in the world of matrimonial ceremonies.

No, I'm not a priest, a rabbi, or a justice of the peace. Just a regular guy with access to the internet (and AI) who was granted a one day license from the great state of Massachusetts to take part in the love story of two people I cared a ton about.

Whether it is the first AND last time...or if there are more to follow, I couldn't say, but feel free to reach out if you want to be my second :)

As I stood there, watching Matt and Devyn come down the aisle, I was nervous as hell! I couldn't help feeling emotional in seeing their excitement, anticipation and how their lives were unfolding into something beautiful. It took me a second, but I settled in and had an absolute blast performing the ceremony. I was overwhelmed with gratitude for the opportunity to play such a key role on the most important day of their lives to date.

Somehow, I managed to not ruin it.

After the wedding, it's impossible not to reflect on the moment. And as being a founder has played such an important role in my life, the metaphor of "mawwiage" and its applications to startup life became readily apparent.

I mean, getting married and founding a company are essentially the same thing. Sure, one involves a tuxedo and the other a hoodie, but at their core, they’re both about commitment, trust, and taking a giant leap of faith.

1. The Proposal: The Perfect Pitch

In both marriage and startups, everything kicks off with one key moment: the proposal.

Whether you're asking someone to spend their life with you or pitching to an investor, it's all about nailing that moment of truth. You’ve got to put yourself out there, be vulnerable, and hope the other side sees the value in your vision.

Founders might stress over crafting a perfect deck, while a future spouse is planning the perfect proposal. Regardless, you’re praying for a "yes" that changes everything.

And while you think that "yes" is the end of the journey, it is really only the beginning.

Getting married is the launch of a lifelong partnership and its important to know going in, that the most successful startups in this space take real work, compromise, and putting the needs of partnership above your own.

2. Building a Strong Team: No One Survives on Love Alone

Just like marriage can’t survive on love alone, a startup can’t run on passion alone. You need a strategy, financial planning, and, most importantly, a co-founder (or spouse) who shares your vision and will be there when things get rough. Because they will get rough. I know I certainly couldn't have projected how tough things would get for me as a company builder. For startups, fundraising, managing finances and human resources issues tend to rule the day and marriage can suffer from similar stresses.

For many founders the line between business and personal life gets pretty blurry when you are living your mission everyday. You survive through great culture building, team construction and seeking mission aligned partners who will be reliable and trusted contributors. The same should be true for your life partner, friends and the village who supports you post tying the knot.

I have had business partners that I thought were like family to me only to have them turn the other cheek when things got tough. It was flat out devastating. You find out real quick who has your back when it's against the wall and someone needs to do the right thing, especially when it is inconvenient for them or costs them real dollars.

I was grateful to have the enduring support of my amazing wife and kids, my YPO Forum and some very true friends (and a fair amount of therapy) to help navigate it. Being with a partner who understands the long game and is in it to win it with you regardless of the financial impact to them is worth its weight in...well...gold!

3. The Honeymoon Phase: It's All Roses…Until It's Not...And Then It Is Again...and Then its Not

Ah, the honeymoon phase—whether it’s the early months of a marriage or a startup, this is when everything feels exciting and full of promise. You’ve got momentum, people are cheering you on, and problems? What problems?

In reality, if you were going to graph a marriage or a startup, they are normally a series of upward sloping roller coaster rides where you launch or meet a milestone, are filled with energy and optimism, only to settle in and realize that daily life is hard. At Startup Health, we have always preached the importance of mindset and a founders ability to proactively managing that mindset as a critical factor in their success.

I have always said that its easy to run a company when everything is going well, but truly great companies and leaders are defined by their decision making in times of challenge. But for both startups and marriages, having intention and choosing every day to keep moving forward will eventually lead to more moments of achievement, growth and celebration.

4. Strategic Planning: Building an OS for Your Relationships

There are some many great tools and frameworks to run businesses. From OKR's to EOS and beyond, these frameworks give you something to lean on and put a littany of problems into smaller boxes so you can attack them in an organized fashion. They provide an operating system on which you can rely to help you run your business and execute. We all know that execution is what really matters at the end of the day.

I have found that most people (including me) do NOT apply this type of systems thinking to their relationships or families and I think its a big missed opportunity. I have always been very impressed when people apply these types of tools and frameworks in a personal setting. This level of thoughtfulness, instead of just being reactionary, forces couples to communicate proactively and with an agreed upon set of rules to find some common ground about their individual and shared expectations and goals. This is important as I had a great business coach tell me, "The root of all unhappiness is uncommunicated expectations," which I buy into wholeheartedly. What these frameworks allow for is better communication and an alignment that we normally would take for granted. But, by being prescriptive in applying these models, we can avoid pitfalls in both our business and personal lives.

As an example, I went ahead and developed a possible relationship flywheel which looks something like:

The Relationship or Marriage Flywheel

• Love & Respect: Consistent expressions of affection, admiration, and appreciation.
• Communication: Open and honest dialogue, active listening, and clear expression of needs and emotions.  
• Quality Time: Dedicated time for shared experiences, meaningful conversations, and fun activities.  
• Trust & Commitment: Unwavering faith in each other and dedication to the relationship's growth.
• Intimacy: Physical & emotional closeness, fostering connection.  

You could see that if we started with love and respect, openly communicated, and staked out quality time, those shared experiences would drive more trust and commitment, leading to more intimacy and therefore building more love and respect!

If you wanted to apply this same flywheel to business relationships it could really be about building a great culture...just without the love and intimacy. Maybe, substitute caring and vulnerabilty instead to keep it more professional ;)

5. Conflict Resolution: Fight Fair

Every founder (and every married couple) quickly learns that conflict is inevitable. Whether it’s about how to allocate funds or how to stack the dishwasher, disagreements will happen. The key isn’t avoiding conflict but handling it with grace and with each others mutual interest in mind.

In a startup, this means figuring out how to disagree with your co-founder without threatening to pull funding. In a marriage, it’s about learning that sometimes your relationship doesn't need to be a zero sum game. I mean, the toothpaste tube can be squeezed from the middle without it being the end of the world, can't it? Either way, the best relationships (business or personal) are built on compromise, respect and a willingness to do act for the greater good.

6. Shared Wins: Celebrate the Small Stuff

Whether it’s hitting a revenue milestone or finally deciding on the wedding registry, it’s important to celebrate small wins. They add up building on one another to keep you motivated. They are like lego pieces of positivity.

In a startup, getting that first paying customer feels like you just landed on the moon. In a marriage, it starts with the wedding, then to career success and then to starting a family and beyond.

Recognizing these moments—whether it’s success in the market or bringing home your first pet—is what keeps the love (and hustle) alive.

7. The Long Haul: It’s a Marathon, Not a Sprint

Both marriage and startups are long-term commitments. Those who go into either thinking it’s going to be a quick success are in for a rude awakening. The real test of endurance isn’t in the proposal or the honeymoon phase, but in the years of sustained effort that follow.

You’ll face setbacks. But, much like a founder sticking through a tough market or a married couple weathering their first big challenge, success comes to those who push through the tough times and do it with compassion and empathy for their team or significant other.

Conclusion: At the End of the Day, It’s All About Partnership

The biggest similarity between marriage and being a founder? It's all about the partnership. The best co-founders—like the best spouses—know that it’s not just about the wins but how you handle the losses together. It’s about picking each other up when things go sideways, laughing through the chaos, and keeping the shared dream alive, whether that dream is disrupting an industry or just making it through a really busy and hectic week trying to balance family and career.

So, whether you’re thinking about founding a company or tying the knot, remember: both are rollercoasters, and the only way to get through is by holding on tight and enjoying the ride.

Now go ahead, say “I do”—to either one, or both!