What it's like to be venture backed

What it's like to be venture backed

I bootstrapped Clockwork for four years out of my own checking account before a single investor put in a dollar. Then I spent a year getting more than a hundred nos on a $2M round before a group in Boston finally said yes. This one is about what nobody tells you: what it's actually like to be venture-backed after you've bootstrapped. Why nobody would fund AI in 2018. Why I had to leave the midwest to raise money at all, deep pockets and short arms. The three tells that make me walk out of an investor meeting. And what really changes the day the money hits, the performing every quarter, the constant updates, the value-add you learn you can't count on. The raise is the photo. This is the part nobody films. New episodes wherever you listen. If it hit, share it with a founder who needs to hear it.

The Time I Almost Sold My Company

I never wanted to sell Clockwork. Started it in 2018 with one plan: build something that lasts and take it all the way. No exit strategy, no flip. So when a company came sniffing around, then ghosted, then came back and actually put a real acquisition process in motion, I found myself somewhere I never thought I'd be: at the table, lawyers drafting docs, tech diligence done, talking dollars and cents about life-changing money. Then a corp dev guy got dropped into the deal and blew the whole thing up. This is the full story of how it fell apart, why I walked, and how the entire organization that wanted to buy me imploded about a month later. "The process is the diligence." It always works out. And no job title is an excuse to be an asshole.

The Most Dangerous Person In The Room

Three stories from back when I was running an outsourced CFO firm and getting pulled into other people's messes. The first one is a "CFO" who told a startup they had nine months of runway when they actually had three. The second is an exec with a perfect resume who locked me out of my own email, Slack, and bank account overnight. The third is a founder who was quietly skimming his own company while a partner at the fund covered for him. The thing all three had in common is that the most impressive guy in the room, the one with the best title and the best resume, was the actual problem. And the title is what kept everyone from looking too hard. I kept being the outside guy who got brought in to say the real number out loud, and the number itself was almost never the surprising part. It was always a person who knew and had a reason to stay quiet. These are wild and they're all true. And the people who blew up those companies mostly walked away fine. I'm not building to some ending where they get what's coming to them, because that's not what happened. If you're a founder, or you're about to hand your company off to somebody who tells you they've got it handled, this one's for you. Stop hiring the resume. Listen on Apple, Spotify, YouTube, Amazon, or wherever you get your podcasts.

If I Started My Company Over

Five things I would do differently if I were starting Clockwork from scratch tomorrow. None of them original. Almost none of them what any first-time founder actually does, including the version of me who started Clockwork. Hire a technical cofounder before you incorporate. Spend the first year on marketing, not on product. Stop overbuilding past the version the market would already buy. Stop hiding inside the codebase to avoid the part of the job you're not as good at, which is selling. And the contrarian one — admit that being too early is a problem unless you have the perseverance and the cash to outlast the wait. I made every one of these mistakes building Clockwork. Some of them cost me years. This episode is the honest version of what I'd tell year-one-me, not the LinkedIn version that flatters everybody involved. The cofounder admission is the most self-implicating. The "building was the easy part for me" lesson is the one I keep relearning. And the "we were too early" beat is the one I think founder media is dishonest about. Most companies that were too early died. Survival is what made the ones who didn't look like they had vision. If you're a founder, or you're thinking about becoming one, this is the advice I wish somebody had given me before I started. Listen on Apple, Spotify, YouTube, Amazon, or wherever you get your podcasts.

My Most Viral Stories

What if the posts you almost don't publish are the only ones that actually work? I went into my LinkedIn analytics and pulled my top ten posts of the last year. The result was uncomfortable. Three of the ten were confessions about what building Clockwork has cost me — 100 pounds lost, four years going broke, three years sober. One was me publicly picking a fight with the industry I came from. The thought-leadership posts I'm proudest of? Tier four. In this episode I walk through each of the top ten. Not by reading them back. By drilling into what was actually going on when I wrote them, what I left out, and what I think about them now that I've seen the data. The Outsourced CFO post that did ninety-one thousand impressions and broke into a comment-section war I wasn't sure I could survive. The hundred-pounds-lost post that became the highest-reaction post of the year. The "I went broke building Clockwork" post that sat on my drafts for two days before I hit publish, that almost didn't go up at all. And the question the data forced me to ask. Are you posting for the version of yourself you want to project, or for the version of you that's actually doing the building? Because at least in my case, the audience isn't interested in the projection. They want the build. A meditation on confession, self-implication, and the gap between the founder you're trying to be and the founder your audience keeps voting for. Listen on Apple, Spotify, YouTube, Amazon, or wherever you get your podcasts.