Starting a business with your friends can be a risky proposition. If things don't go well, the relationships may not last or, at least, become incredibly strained.

At the same time, starting a business is a challenge in its own right. Who better to have along for the ride than the people you trust? When things get tough, who else to have with you in the heat of battle than your friends?

I started my first company out of my dorm room at Stanford University with my roommate and great friend Ronnie. With a lot of hard work, that business grew and became successful and was eventually acquired. I look back on those years of my first startup with great fondness, and what I remember most clearly isn't the endgame but the journey--the late nights, laughs, and problems solved. Building a startup is such a commitment that if I'm to take time away from my family, I want to enjoy that process with people I genuinely like.

A decade later, when I set out to build my latest business, Porch.com, Ronnie was one of the first people I called. He was in from the first chat. He quit his job, worked out of my basement in the early days, and even went as far as skinning his entire car with our company logo. Ronnie still drives around in the Porch-mobile, even though we've since changed the colors of our brand. Now that is commitment!

Over the past year, Porch has grown from 20 people to more than 200. I've brought in a few other friends and made new great ones. The Kodak moments we have shared are countless, and I wouldn't trade them for anything.

As someone who has proactively worked to build businesses with friends, I'm here to tell you that when done right, it can be one of the most enjoyable and rewarding experiences of your life. For anyone on the fence, here are five reasons why you should invite your most capable friends to come on board when starting your business.

1. You have a foundation of trust

Trust is built from shared experiences, and when you start a business, trust needs to be a cornerstone of your culture. When things get tough and the pressure is on, you need people around you who will stick it out and have your back. When you make a mistake or are doing something dumb, you need people who will call you out. With trust, you can be fully transparent as you build your business, which I believe is critical for a team to operate at its best.

2. You know one another's strengths and weaknesses

When working with someone new, it takes time to really understand his or her strengths and weaknesses. One reason I like to start companies with friends is we already know where we each excel and struggle. I've played sports with them, gone to school with them, and have seen them in both the good times and the bad. That makes it very easy to get people into the right roles quickly and move as fast as possible.

3. You know how to disagree (and get over it faster)

In a fast-paced work environment, arguments and disagreements are inevitable. When you don't have a personal relationship with someone, there is a learning curve for understanding the right way to resolve disagreements. When you are working with your friends, you can get to the truth faster. Chances are you've already had countless arguments with your friend before; the best part is, you're still friends. When you do have tough disagreements, you can get over them faster and get back to executing on the business.

4. The successes are sweeter

The true joy in building a business is found in the journey, not the destination. But there is something to be said about reaching big milestones with friends. When you launch your website or get your first customer, you get to experience it with friends instead of just telling them about it after the fact. At the end of the day, you always have lots of reasons to celebrate with your co-worker friends.

5. It is more fun to work with people you like

Plain and simple: It's fun to work with people whom you actually like! We spend a significant amount of our lives working. Add in the quality time spent with our families and additional outside obligations, and we don't always get to see our friends as much as we'd like. The simple fact of just being able to spend more time together is more than enough motivation to look to a friend when starting up.

Published on: Sep 9, 2014