The Benefits of Starting a Family Business — and How to Do It Successfully

(This article was initially featured on Entrepreneur.com on March 16, 2023)

There’s a classic expression that one shouldn’t mix family with business; However, some of the most powerful entrepreneurial duos were related in some way, shape or form.

So in 2014, when I decided to co-found a company with my brother, I wasn’t entirely sure what to expect. We’d shared a bedroom for almost 10 years, but could we share a cap table? The last time we had to split anything it was a personal pizza, and I obviously deserved the bigger half because I was the older brother.

In all seriousness, I knew that we had an incredible relationship and we trusted one another, but I was also worried that this venture might royally screw up that relationship. In the end, it all worked out and became one of the most rewarding experiences of my life. 

This article builds the case for starting a family business and suggestions on how to mix the two for the best possible outcome.  

You know each other’s moves

Growing up, my brother and I would play one-on-one basketball in our front yard. We’d complain about the fact that each of us had a “move” that neither of us could stop. However, when we played two on two, we always seemed to figure out how to use these moves together to play better.

As entrepreneurs, we entered the game knowing what our strengths were and could more easily defer to one another in different situations.  This process wasn’t perfect in the beginning. It did take some time to drop some of our prior expectations, specifically, which roles we’d play based on things that really didn’t matter like our age, title, and years of experience. 

However, we had spent decades establishing trust whereas our competitors might only have ten or fewer years of working experience together. This allowed us to make better decisions on day one versus having to spend years laying the foundation of trust.

The fights are intense but the resolution is quicker

My brother and I had some epic throw downs over the years. We’re still not allowed back in my mom’s hairdresser after the “Connie’s Corner Cuts” melee. 

As related founders, our feedback tends to flow more freely and our fights are more emotionally charged.  This forced us to be more conscious of and sensitive to the impact that these fights had on our other co-founders and employees. Don’t have the blowout fights in front of your employees. While this interaction between siblings may feel normal, it might suggest that there’s dysfunction in an otherwise healthy and thriving organisation.

On the positive side, with 30 years of experience fighting with one another, we’re able to come to a resolution quicker and gain alignment on key issues because we know how to have direct conversations without taking things personaly. That has also become a major strategic advantage to move our business forward more quickly.

The stakes are higher and the wins mean more

My brother and I founded our company the year that my daughter Laura was born. I wanted to create a better life for her and my family, and my brother shared that level of accountability to build something that could provide financial independence for our immediate families.

When things were rocky and our bank accounts were empty, we couldn’t quit on one another. Failure would not only make holidays awkward, but based on what we had both personally invested in the company, it would take years to recoup that loss.

When we sold our company in 2021, it was a life changing event for each of our families. Aside from the days my kids were born, I don’t think there has been a higher moment in my life when we closed on the sale of our company. Not because of the financial impact, although that helped, but more because I knew we had taken care of the people that we love most in the process and set an example for our kids on what it means to fight for something and the people that matter most.

Would I do it again?

Without question. Our time on earth is limited. On average, we spend 90,000 hours of our lives working. I want to spend that time with the people I love and trust, at least until one of us taps out and says “uncle”.

A couple of takeaways

• Working with family is awesome. You have established trust that can often take years for non-related founders to build, which becomes a major strategic advantage.
• You’re already good at fighting and you know each other's moves. Bury your egos and work in a way that aligns with your natural strengths and abilities. 
• The stakes become higher, so you’re accountable to one another to not screw it up. 
• Make space outside of your venture to focus on maintaining your personal relationship with your relative-co founder.