3 Lessons Learned from Going into Business with Your Friends

Hai Truong
4 min readApr 23, 2015

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A visual sampling of our work trip held at a cabin atop a mountain in Ramona, CA.

All the challenges, the hardships, the good and the bad — all of it came out in a deep conversation in a cabin atop a mountain in Ramona.

It wasn’t quite a Waiting to Exhale moment, but it was a turning point for us as 3 friends who've been living and working together on a business we took over about a year and a half ago. Going into business with your friends can be fun, exciting, and rewarding when things go right and also a large source of stress and conflict when you’re not on the same page.

I’ll share a few things we learned on this trip in the mountains. It’s something we do at least once a quarter for a change of pace and variety. These things may be helpful to provide some perspective the next time you encounter challenges that come along with working with your friends and especially if you’re going into business with them.

1. ) Honest communication on a regular basis is healthy, even when it’s initially uncomfortable.

2. ) Growing both individually and collectively as friends is important.

3. ) Have a good balance between work and play.

When you live and work together, talking about work often precedes the conversations you’d regularly have as friends if you didn’t have a business you share together. Over time, you don’t realize that the conversations you have as friends become more infrequent and you become more colleague than compadre.

We realized this was happening and something needed to be done about it. So we had a long conversation that encompassed the 7 year friendship we’ve had with one another.

It was hard and uncomfortable at first but when these are friends you care about, and people you trust enough to stake your financial future on them, it’s worth working through it.

Some unexpected truths were a little tough to hear at first — but ultimately, we’re better friends and also more aware of each person’s situation in relation to the business now too.

The foundation of trust begins with deep roots. The longer you know someone, the more likely that some of the small details may fall through the cracks.

Going into business and sharing the same roof as your friends is essentially marriage in many ways including the shared bank account. And in any relationship, once you stop noticing and keeping up with the little things that make the relationship work and stop growing, you’re bound for rocky waters.

We’re not immune to that either which is why we figured out over the course of this trip that we need to take a step back sometimes and look at how we’re affecting each other for the better. In the times that it’s for the worse, then it’s time to recalibrate and figure out how to encourage continual growth — otherwise, we’re doing a disservice to ourselves and the people we care about.

The wise words of Dr. Seuss

The whole reason we go into business with our friends is to build something you can share with people you respect and care about. You also hope that you’ll have fun. So how is it that in the hustle of it all we sometimes forget that the people we’ve gone into business with were first friends whom we’ve built a body of memories with? What is supposed to be fun instead turns into a source of stress and concern.

It has happened to us at times and it’s because we sometimes forget to step back and see this opportunity for what it is — an opportunity to have more balance between work and play than we’d otherwise have in a job. Hustle is necessary, but when you’re not enjoying what you’re doing with the people you’re doing it with, you can quickly turn a passion based, self employment gig into something you eventually loathe.

There’s no secret sauce to making it work when you enter in a venture with your friends, but these three lessons we’ve garnered have helped us get perspective on what we’re doing, where we’re going, and who we’d like to become. Some laughter, some necessary honesty from time to time, and a whole lot of humility can get you through some of the conflicts that seem impossible to overcome.

What kind of challenges have you experienced or lessons have you learned working with your friends?

Cheers and Thanks for Reading,

Hai Truong

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Hai Truong

Writer and marketer exploring vulnerability and self-acceptance one conversation at a time. www.haifidelitypodcast.com