Keep Going: No Founder Should Go to War Alone

This week on Keep Going, I sat down with Karl Alomar, Managing Partner at M13, and former COO of DigitalOcean.

Carl’s career, when you say it fast, sounds like a highlight reel. He came to the US from England with an engineering background, started his first company in California in the late 90s, sold it in 2000, got an MBA at Columbia, built a global fintech business to real revenue and exited in 2010, then joined DigitalOcean and helped take it from early product days to IPO. Now he invests at M13.

I pushed him on the part people skip, the moment where it almost breaks.

He told a story from his first company that still makes my stomach drop. They were raising a big round for the time, about $20 million. Closing day. Fire alarm. Everyone in the parking lot. He gets a call on a brick of a phone. The lead investor tells him the bottom just fell out, they cannot close, they do not know if they ever will. That is not a small problem. That is the whole floor giving way.

Carl had to make choices fast. Cut the team in half. Slash spend. Decide whether to try to patch the round together without a lead, which is close to impossible when the mood turns. He had been approached by potential buyers earlier, and in a hot market those talks feel optional, almost annoying. In a cold market, those talks are the only door that still opens. He took the door. In about two months they got an exit. Not the dream outcome, but a real outcome. People got returns, everyone lived to fight again.

What stuck with him was not the deal mechanics. It was the loneliness.

He said he had no deep bench. No real board support, no real advisor bench, no system around him when the air went out of the room. He was young, the pressure was on him, and he felt like an island. His lesson was blunt. Never go into battle without an army. In plain terms, build a support network before you need it. Investors, board members, mentors, peers, people who can tell you the truth, and keep you steady enough to make good calls.

I asked him what that looks like in real life. He was clear that it is not some magic fix. For him it is not a yogi. It is the people you choose to take money from, the board you build, the mentors you keep close, the peers you can call when you are scared and tired and tempted to lie to yourself. He also noted that the culture has changed. Coaching is normal now. Mental health is talked about more openly. In the late 90s, money was just money, and nobody asked what came with it.

Then we moved into the question sitting in the room with all of us right now. AI. Are we headed for another crash, another 2000.

Carl pushed back on the timing in a way I found useful. He thinks we are closer to 1996 or 1997 than 2000. Early. The “killer” product is not fully settled. He used the browser era as a frame. People thought browsing was the point, but search was the point, and Google won by solving that. His take is that AI still has not found its final shape, not in a way that locks the category down. We have chat tools and model access, but the big lasting system, the one that makes the next giants, is still coming into view.

He also pointed out something practical that founders feel every day. Building in AI is still expensive and hard. The tools and the cost curve have not flattened the way cloud did for web builders. If cloud made it cheap to ship software, what makes it cheap to ship AI. Better access to compute, better tools around data and GPUs, better infra. He is excited about the boring part, the picks and shovels that let more people build.

I asked the other side of it, the part people whisper about. If you are a regular worker and a wave is coming, what do you do. Carl did not pretend he could map the next 20 years. But he did say the labor market shifts, it does not just vanish. Some work gets automated, other work shows up, and the shift is not overnight. He brought up the growth of gig work, the rise of people building independent lives outside big firms, and the simple fact that lots more people now want to build things than they did decades ago. He sees that trend getting stronger as tools get better.

He is not an AI cynic. He thinks cynicism is a way to lose twice, first by missing what is real, then by refusing to adapt. He is optimistic, but he keeps a realist’s eye on the losers that come with any big wave.

As we wrapped, I asked what he looks for when he sees the fiftieth “Fitbit for dogs.” He laughed, because he has seen it. His answer was old school. He starts with the founder. Can he work with this person for years. Do they have vision, and can they explain it. Can they hire. Can they raise. Can they steer when the first plan fails. He brought up Slack’s origin story, a good reminder that a strong founder can turn a weak start into a real company.

That is the episode in a line. Big waves come, and they always feel obvious after. In the moment, they are confusing, loud, and full of bad copies. The way through is still the same. Keep your head. Build your people around you. Make choices you can defend in the morning.