The 4 Most Important Things About Your Co-Founder

What I’ve learned from starting a company with my brother

Jon Sadow
6 min readJun 17, 2016

There are tons of posts about How/Where To Find a Co-Founder. But I haven’t seen a whole lot of content about what actually makes for a great co-founder relationship. Finding a co-founder is hard work. It takes a long time. So entrepreneurs are liable to make convenient or expedient choices — and risk under-evaluating whether that grouping can lead an entire company.

Rob (left) and I, thinking inside the box since the 90s

A year and a half since starting Scoop with my brother Rob, I’ve learned a lot about the dynamics of co-founder relationships. The way you lead together with your co-founder is fundamental to your ability to grow your company successfully and make sense of the journey of being an entrepreneur.

Here are what I believe are the 4 most important considerations for a successful co-founder pairing.

1. You’re going to fight.

But can you make up?

Being a founder is at least 95% emotional. The stress is unlike anything else you’ve ever had to deal with. The pressure never goes away. And when you have that kind of tension, you’re going to fight. You’re going to argue. You’re going to disagree. All the time.

What matters is being able to make up. With Rob and me, our advantage is that we’ve had years of practice! We’ve been fighting (like any siblings do) for decades, and so it’s second-nature for us to be able to take things in stride and not take them personally. I can’t count the number of times we have argued about something Scoop-related — serious, yelling-laden arguments — just to grab dinner that night or have totally moved on from it by the next morning.

So, if you’re going to start a company with someone, you better be ready to fight — and be able to make up. If you think your potential co-founder is the passive-aggressive type even with you, beware. If you’re not sure they will be able to recover from disagreements and might hold grudges, that may be a red flag. If they’re non-confrontational and you’re aggressive (or vice versa) will you be able to handle the conflict? If you won’t be able to make up, find someone else.

2. 80/20 + 100%

Complementary skills + philosophical alignment

One of the biggest mistakes I see and hear about with co-founders is too much overlap in their skill-sets. This is especially true for all-technical or all-business founding teams. In my opinion, the ideal ratio is 80/20–80% of your skills should be complementary and 20% should be overlapping.

Rob and I have very different backgrounds. He spent years as a consultant/manager at Bain and Company. His expertise is in strategy, market analysis, and customer segmentation. He knows how to break down problems and find solutions.

I was a PM at Google (and before that, Sales and BD). My experience is in building products, understanding user experience and delivering what customers and users want.

These very different skills serve our business needs effectively. Most importantly, the complementarity ensures that we can comfortably defer to each other on specific topics. I know what he’s an expert at and vice versa.

But, we also have valuable overlap. We’re both incredibly analytical. We’re Excel (or now, Google Sheets) gurus. We’re very data-driven and some of our most collaborative moments have been when we can dissect data together to turn it into strategy.

Having that balance in skill sets — and a small bit of overlap — accelerates our decision making and makes us better partners. Our honesty with ourselves and each other about those skills has also helped us build out a 15+ person team of smart, capable people that complement us as a co-founding pair. (I’ll share more about this in an upcoming article about hiring the right people quickly).

But most importantly, while we have 80/20 skill overlap, we have 100% philosophical alignment. Before we started Scoop, Rob and I wrote up a document that outlined the guidelines we had to agree to if we were going to start a company together. It talked about everything from market size requirements to personal timelines to company culture. We knew from the beginning that we were totally aligned when it came to our philosophies about becoming founders & entrepreneurs. This is one of the reasons we started a mission-driven company.

Our north stars are always identical. We know exactly what we’re trying to achieve, what matters to us, and what we want for Scoop — personally, professionally, and as a company. If you don’t already have this with your current or potential co-founder, find it immediately or find someone else.

3. Trust, trust, trust.

Rob is smarter than me (don’t tell him I said that). He is the best person I’ve ever worked with and I have more faith and trust in his ability to get things done — and make the right decisions — than anyone I’ve ever worked with. That makes it easy to trust him unequivocally.

Being brothers obviously makes this trust more natural. But that doesn’t mean it’s any less important — or possible — for other founders. If you doubt your co-founder — even just the smallest degree — you’re in serious trouble. You’re going to need to trust them to talk to investors without you, manage team members without you, and make thousands of critical decisions without you.

You learn quickly when starting a company that you can’t — and shouldn’t — do everything. It’s hard enough work to build a team you can trust. If you don’t trust your co-founder to do the right things and make the right decisions, you’re in for a long, long road ahead. The instant you feel or express doubt about your co-founder — as a fit for you or your company, or about their overall competence — it’s imperative to do something about it. Either clear it up, talk it out, or find someone else.

4. You better like them.

I’m always taken aback when people describe the competence or intelligence of skills of their co-founders — and say very little about their personalities. Attention future founders: in case this wasn’t already obvious, you’re going to spend an insane amount of time with your co-founder. I spend more time with Rob than my wife. Or anyone else in my life, for that matter. We’re at work together all day. When we’re not working, we’re on the phone constantly. And, we socialize.

That last part isn’t just because we’re brothers. You SHOULD socialize with your co-founder. You need to build that relationship. You need to have fun together. You need to push each other to see the world outside of the business.

If you don’t want to grab a beer with your co-founder…yikes. If you don’t think it’s fun to sit down to a nice dinner together…yikes. Every investor or partner or employee will look at your relationship — not just the professional one, but the personal one. Do you joke together? Do you support each other? Do you understand each other? If not — you guessed it — find someone else.

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Rob (right) and I, standing in traffic

Co-founders are the backbone of your company. Your personal and professional relationship influences everything that happens from day 1 to day N. Your whole lives will be entangled and intertwined in ways you can’t imagine. So, find someone you like; someone you trust. Find someone who will make you stronger, and who complements your skills — but not all of them. Don’t start a company with someone just because they can do something you can’t, like code a website or bring on enterprise partners.

Start a company with someone who wants to change the world the way you do.

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Jon Sadow is the Co-Founder and Chief Product Officer at Scoop, the fully-automated carpooling solution for your daily commute. Prior to founding Scoop, Jon spent 5 years at Google in both Product Management and Business Development. Jon is a graduate of the George Washington University in Washington DC, and now lives in San Francisco with his wife, Michelle, and their dog — and Scoop mascot — Kugel.

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Jon Sadow

Co-founder and CPO @ Scoop | Previously PM @ Google | sports & politics junkie | husband and dad