Finding the Right Co-Founder for a Tech Startup

I’m a serial entrepreneur and sold my previous startup to PayPal. My current company has already raised nearly $20M. Here’s my advice on how to pick a co-founder. / Complementary skills It’s tempting to pick someone just like you, with the same background and skillset. But that’s a trap. You need some overlap – but not duplication. If you're great at engineering, find someone who lives and breathes GTM, design, or fundraising. Two tech guys? Fun for side projects, but not for scaling a company. / Comparable experience It doesn’t matter if one of you is older or comes from a different industry. What matters is that you’ve both built stuff before. If one person still needs mentoring, the balance breaks. My co-founder Victor Gane and I have ten years between us, but we're equal partners. We’ve both raised money, hired teams, closed deals, and bootstrapped products – that shared scar tissue matters. If one of you needs coaching, you’re not co-founders anymore. You're a mentor and an apprentice. / NOT your best friend Any high-performing team won’t work without total candor. And with close friends, it becomes harder to be candid. Feedback gets filtered. You hold back to avoid conflict. You don’t need your best buddy as a co-founder. You need someone you can argue with at 11 p.m., still show up the next morning, and trust to own their part. With Victor, I knew he was smart, honest, and reliable. That’s what counted.

Finding the right co-founder is the single most important thing that can make or break a startup. But so many people rush into it without thinking too hard about it or truly trying to understand compatibility. Before starting Gem, I spent almost a year trying to find the right cofounder. It sucked. I almost gave up twice. I tried a number of month-long “co-founder dating” arrangements with folks I hadn’t worked with, which were hit or miss, and reinforced the importance of teaming up with someone I knew and trusted. I’m so glad I stuck with it, because I finally teamed up with Nick Bushak‎, and I couldn’t have asked for a better co-founder. With that said, it took me almost a year to find Nick. Here are the 3 things I would have done differently having gone through this: 1️⃣ ‎ Make a short-list of the 5-10 folks where I’d drop everything to work with them as soon as I was even considering the possibility of starting a company.   2️⃣ ‎ Catch up regularly (e.g., every 1-3 months) with everyone on the short-list well before either of us is ready to take the plunge (coffee, dinner, walks, drinks, etc.). In my experience, finding the right co-founder is a non-linear process and can’t be forced, so it’s a good idea to be planting seeds early. 3️⃣ ‎ If someone’s timing lines up, drop everything and dive right in, even if it’s inconvenient. So much of finding the right co-founder is about timing, so seize the moment when it presents itself. I feel like this part of the startup journey is often overlooked and not talked about. For those of you who found an awesome cofounder, how did you do it? How did you know they were the right one?

Finding a co-founder is like dating, but with way higher stakes. Startups rarely fail because of the idea. More often, they die because the co-founders don’t work out. Here’s the checklist to go through with your co-founder, beyond just “complementary skills”: 1. Talk equity, early. Have the awkward conversation — how much, why, and what it signals. Don’t postpone it. 2. Align on vision. Early exit? Long-term grind? Willing to go 2 years without a salary? Talk ambition and timelines. 3. Talk finances. What salary do you need vs what you want? What happens if one needs more? Frugality mismatches lead to tension. 4. Location flexibility. What if you need to move cities or countries? Can both of you? Willingness to relocate matters more than you think. 5. Conflict resolution. Disagreements will happen. Decide now who gets the final say when there’s a deadlock. 6. Division of boring work. Admin, finances, contracts, CA calls, and lawyer coordination. Who’s doing it? Someone has to — and it’s rarely fun. 7. Understand their defaults. How do they deal with stress? Spend money? Travel? Party? Live? These small things hint at big compatibility gaps (or alignment). Founders love to plan for scale. But before that, plan for the first 100 days - who’s doing what, how you’ll make decisions, and whether you work well together. You can’t afford to get this wrong.

There's a 65% chance your startup will fail because of co-founder conflict. Here's what I've learnt after working with the same co-founder for 6 years. 1. don't look for a co-founder at some accelerator, it’s a stupid trend imo. Co-founders should have more history than just starting a company (no arranged marriage). 2. keep a ‘dating period’ before you sign the ‘marriage certificate’ (even with friends). Break it off if it isn’t working out- I tried making it work with 5 people before finding Aman. 3. don’t find a ditto copy of you, get complimentary skills + attitude on board. 4. over-communicate, talk about everything - even stress, don’t try to act a hero and keep it to yourself. 5. don't fight over equity, keep the distribution as close to equal as possible, it builds long term trust- which you'll need because your first startup will most likely not survive. 6. know each other’s ambitions, interests and life outside work. Self-interest-driven transactional relationships often end up in conflict. Finding the right person can be challenging, but you’ll spend significant years of your life with them, so might as well get it right. What do you think? #startups #founders #entrepreneurship #startupjourney

80% of startup co-founder relationships fail within the first 3 years. But it's rarely about skills. Most founders pick cofounders based on technical abilities - the best engineer, the smartest salesperson, or the most experienced operator. Big mistake. Because in a startup, it's not skills that break teams - it's misalignment. Here's the truth: ▶︎ 1. Skills won't save you when things go sideways Every startup hits a wall. And in those moments, it's not your CTO's tech stack that matters - it's whether they take accountability or point fingers. ▶︎ 2. Misaligned values create silent resentment I've seen cofounders fight over small decisions. Not because of the decisions - but because one cared about impact, the other cared about money. That difference doesn't show up in pitch meetings. It shows up in year 2, when one wants to raise, and the other wants to exit. ▶︎ 3. Communication styles make or break momentum One founder I worked with made every decision via Slack. His cofounder wanted to talk through everything in person. Same vision. Same goals. Total friction. Startups die from miscommunication, not market failure. ▶︎ 4. Habits matter more than resumes Early bird vs. night owl. Builder vs. brainstormer. Chaos vs. structure. None of these are wrong - until they collide in a 14-hour sprint to get a demo ready. ▶︎ 5. Vision drift is real - and dangerous Your cofounder isn't just helping you build a product. They're helping you build your life. If you don't agree on what that life looks like, you're heading toward a split. So yes, skills are important. But when I work with early-stage founders, I always say: Pick someone you can survive hard days with. Because those are the days that actually test your company. What's one non-negotiable you'd look for in a cofounder - beyond skills? #entrepreneurship #startup #funding