If I Started My Company Over

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.

My "technically impossible" company

120 VCs told me no over four years. They said it was technically impossible. They said it wasn't venture-backable and I should just make it a lifestyle company at a million a year. They said finance was an art, not a science, and AI couldn't apply to it the way I was describing. Four years later, one of them came back asking me to pitch him. I said no. This is the story of those 120 rooms. Of being four years early. Of the texture of building when none of the people who call themselves AI investors can see it yet. And of the honest middle of this story I haven't told before. That I was the kind of stubborn founder I would have told to quit if I'd been advising me from the outside. Being early and being delusional look the same from the inside. I'm not telling anyone to keep going. I'm telling you the math is real, I'm an outlier, and the responsible advice would have been to stop. For anyone who's ever been told "this isn't possible" by someone who turned out to be wrong, this one is for you. Especially the part where they come back. The Real Slim Fady Show: Apple → https://podcasts.apple.com/us/podcast/the-real-slim-fady-show/id1640522523 [https://podcasts.apple.com/us/podcast/the-real-slim-fady-show/id1640522523] Spotify → https://open.spotify.com/show/33udmtFwjLFt48pWSViwUz [https://open.spotify.com/show/33udmtFwjLFt48pWSViwUz] YouTube → https://www.youtube.com/playlist?list=PLW5rJOCqHMcDbHDCb5NZ693m7unzbUmGj [https://www.youtube.com/playlist?list=PLW5rJOCqHMcDbHDCb5NZ693m7unzbUmGj] TikTok → @therealslimfadyshow Fady: X → https://x.com/FadyHawatmeh [https://x.com/FadyHawatmeh] LinkedIn → https://www.linkedin.com/in/fadyhawatmeh/ [https://www.linkedin.com/in/fadyhawatmeh/] Clockwork → https://www.clockwork.ai/ [https://www.clockwork.ai/]

Why I Quit Boeing at 27

At 27, I was on the people-to-watch list at Boeing. Six months later, I walked out because I wouldn't accept the corporate game. This is the full story, the financial model my manager killed in 10 minutes despite never having built one, the performance review that turned out to be a math problem, and the phone call I got nine months after I quit that I still think about. It's also an honest answer to the question I get asked most: what's actually different about corporate vs. founder life? The short version, in corporate, you're a number. In a startup or small business, you ARE the number. The bell curve doesn't disappear when you become a founder. It just changes denomination. If you've ever sat through a calibration meeting wondering what was really happening to your career, this one is for you. Chapters: 00:00 The phone call I'll never forget 01:35 From Seattle to St. Louis 05:20 Building the model 08:30 Killed in 10 minutes 12:05 A meets-expectations review out of nowhere 14:35 The bell curve confession 17:35 Refusing to sign anything 23:00 "Maybe if you'd listened to him, he'd still be here" 25:30 The bell curve doesn't disappear when you raise 28:50 In corporate you're a number. In a startup you ARE the number. 30:00 Closer Connect: X — https://x.com/FadyHawatmeh [https://x.com/FadyHawatmeh] LinkedIn — https://www.linkedin.com/in/fadyhawatmeh/ [https://www.linkedin.com/in/fadyhawatmeh/] Clockwork — https://www.clockwork.ai/ [https://www.clockwork.ai/] If this hit, share it with one person who's stuck in their review cycle right now.