Burn It Down, Build It Better

The founder’s guide to quitting the wrong company (or relationship) before it quits you

Two years ago to the date, I shut down my first company. And it was not a graceful exit at all, we burned it to the ground. There was a lot of screaming. Threatened lawsuits. Aggressive emails. Refusal to handover logins or service customers. A total meltdown of eight months of hard work.

I was so embarrassed. I thought I’d never recover from my failed attempt to “build in public”, while my Stanford GSB classmates raised rounds and got promoted fast track.

Last night, over Thai food, a close friend told me she’s leaving a decade long relationship that just doesn’t feel right anymore.

Different arena, same feeling. You wake up one day and know you can’t keep living the life you’re living. It’s the quiet terror of saying: this absolutely cannot be my future.

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But you’re paralyzed on whether to do anything about this.

Because it’s so comfortable. Even when it’s wrong, you know the schedule, the cast of characters, the script.

Because the judgment is terrifying. You imagine a faceless Greek chorus whispering about wasted time, failed plans, how badly you misread your life.

Because of the sunk-cost fallacy.Years, energy, reputation — it feels like debt. So you keep throwing resources at it. Pivots. Therapy. Rebrands. You buy time because quitting feels like betrayal.

And women carry an extra layer of fear here. We’re trained to keep the ship steady, to value “stability” over change. We hear the clock ticking louder. That pressure makes it feel reckless to start over, and keeps many of us in things that quietly hollow us out.

But how do you know it’s time to torch it?

1. The joy is gone and hasn’t come back. Not a bad week. Not a tough quarter. MONTHS. If the spark is missing and you don’t even miss it, that’s data.

2. You’re bargaining with reality. “If we just launch this feature. If we just try one more round of therapy…” That’s not strategy. That’s stalling.

3. Your body knows before you do. Chronic Sunday dread. Sleeplessness. A stress cough that never leaves. Your nervous system files the paperwork before your brain signs it.

If those three boxes are checked, you already know. The hard part is admitting it out loud.

your not supposed to be successful the first time

If the train is headed the wrong way, no amount of tidy fixes will reroute the tracks. No startup pivot, no couples therapy, no heroic 3 a.m. work sprint will change its destination.

You need to get the hell off. As soon as possible, because the journey to your real destination is getting longer each second

And then what?

End it, and you get whiplash. Relief. Panic. The cold, wide silence of a blank page.

I nearly took a cushy PM job at Notion just to make the panic stop. That quick exit ramp is tempting.

5 strategies I used to go from broke and jobless (but like literally) to building a a16z funded company in 2 years.

1. You’re not alone. We all have a few exes before the husband.