Seeing Eye-to-Eye with your Cofounder

There are many reasons why startups fail. One of the most common reasons is team/founder issues. The comparisons with dating and marriage are trite and not particularly helpful. Noam Wasserman in The Founder’s Dilemmas has shared what research shows about outcomes from various founding decisions. (I strongly recommend reading the book , but you should at least watch his lecture at Stanford recorded 10 years ago)

However, very little has been written about how to actually make the cofounder relationship work. The day in, day out of building something with a cofounder; the ups, downs and not-even-sure-which-way-is-up of fundraising, hiring, firing, closing deals, writing code; the macro shocks, pandemics and geopolitical conflict you can do nothing about but are still expected to respond to with absolute certainty – all of these combine to make starting a company with someone else a unique experience.

I started InOrbit.AI with my co-founder Julian Cerruti 5 years ago. At least, that’s what the incorporation papers say. In reality, it was formed over a number of conversations: kicking ideas back and forth over coffee, going out to dinner, having long conversations on the phone while we each went for a walk 6,000 miles apart.?

When we started the company, we were told repeatedly by well-informed and well-intended people that it wouldn’t work.

We were told that every robotics company had to build their own -- that sounded like reinventing the wheel to us, so we set out to eliminate waste in the industry. We were told this wasn't a business that could attract venture capital -- we have closed multiple rounds with major investors. We were told nobody would buy from us -- we now have some of the largest and best-regarded companies working with us.?

Most critically, we were told that having co-founders who are not co-located would never work. Since then, we have not only proven them wrong, but were already well prepared by the time the pandemic hit and other companies struggled to adjust to remote work. A (perceived) weakness became a strength.?

According to the Bureau of Labor Statistics, fewer than 50% of new businesses make it past the 5-year mark. Beyond the statistics, 5 years means over 1,800 days of working together. So I wanted to capture some key lessons learned during that time.

1. Building trust is critical; you can fast-forward if you start with a foundation of trust

Trust takes time and time is something that all startups have in short supply. If you can start from a solid base of trust from prior experience working together, that will increase your chances of success. You’ll often hear advice against starting a company with a friend. I think it’s true that choosing a co-founder who may be unqualified just because they’re a friendly face is not a recipe for success. However, keep in mind that you may end up working together every day for 10 years – that will be a long slog if you don’t get along.

Julian and I learned early on that, while we have deeply shared values, we are very different in how we handle uncertainty, ambiguity and planning. We have managed to turn this into a sort of super-power: together we are much stronger, thanks to rather than despite our differences. However, this would have been impossible without a strong basis of trust.

2. Being remote requires focus on F2F (founder-to-founder) communications

We all have a myriad technical means for communication – Zoom, Slack, Whatsapp, whatever. But it’s also very easy, especially as the team grows, to give up the founder-to-founder space to make room for other meetings. Being in a virtual room with a bunch of other people with different roles is not the same as connecting directly. Make the space to keep this up. My cofounder and I make it a point to meet weekly 1:1, travel as frequently as business and personal lives allow, and go on long walks together when we get a chance to talk through the deeper stuff.

3. You will make a myriad decisions, figure out how to do that effectively

Especially during the early days, you will need to make decisions daily. As you grow, the team will keep looking to the founders for many decisions, large and small. Even if you push out the day-to-day decisions (eg which tasks to prioritize) there’s just too much that falls outside of that. In some cases, you will not be qualified or have prior experience, but the decision needs to be made anyway – not choosing something is a form of choosing.?

Need business insurance? Somebody has to find a broker. Lease office space? Negotiate contracts? Even with attorneys and realtors at your disposal, somebody at the company has to drive. Need to fine tune the copy on the website? This is both the joy and the burden of being a founder. You wanted independence? You got it. Over time, you will build more capacity and will be able to delegate more, but the responsibility doesn’t really go away. Founders can support each other by having clear responsibilities but also consulting frequently with each other. Julian and I regularly do “rubber-ducking ” sessions.?

4. Keep each other balanced

One of my mentors shared some advice that I’ve taken to heart: don't get too high on the highs, avoid the lowest of the lows. Everyone will tell you that a startup is a rollercoaster. What they usually don’t mention is that as you’re sitting there on the long, slow way up to the top of the roller coaster, you’ll realize that the restraints aren’t working, and you can see that a piece of the track is missing right after the loop. That’s what it actually feels like in the early days.

So as founders, make sure that you check in on each other, not just about tasks but about feelings. There, I said it. The F word. We’re supposed to be deal-closing, code-writing, shareholder-value-creating machines, but founders are people, too. Like two drunks keeping each other upright, founders can support each other by understanding what’s going on at home, sharing the wins and lessons of work, and allowing yourselves to be vulnerable with each other. As we work on InOrbit, our lives carry on and we get a chance to share them.

5. Build the right culture

There’s only so much that founders can do on their own. Their main responsibility is building a culture that matches the values, goals and aspirations of the founders. The right culture can attract the best talent (especially those that have been burned before), retain the right people (those who are committed to the success of their peers) and help get stuff done (ideally with a minimum of drama.)?

Experienced founders who have been around the block and have tasted different company cultures have an advantage here: they know what they don’t want in their own company, and can try to steer things in the right direction, with every hire, every all hands and every Slack message. Something Julian and I are very proud of is that we’ve been able to build a positive, collaborative and healthy culture at InOrbit.

When the points above aren’t working, you’ll see many failure modes: backstabbing (I prefer my stabbing in the chest), avoiding conflict until it blows up, fiefdoms with non-overlapping teams. Conflict is inevitable, but it only becomes toxic if you let it fester.

Ultimately, the litmus test of the co-founder relationship is that you care for each other’s well-being, respect each other's lives outside of the startup and share the lessons as well as the wins.