Greg Isenberg is a multi-exit Silicon Valley entrepreneur and owner of Late Checkout product studio. He has:
- Headed Product Strategy at WeWork
- Been an advisor to Reddit
- Founded a startup, Islands, which was sold to WeWork
- Founded 5by, which was sold to StumbleUpon
Guest Author: Greg Isenberg
I’m looking for business partners. People who want to build a portfolio of cash-flowing internet businesses. But first, some context. 4 years ago, I walked away from WeWork. I had sold my company to them, watching as they raised and then incinerated $20 billion.
It was unbelievable. Painful.
I vowed never to be part of something like that again.
In the aftermath, I found myself at a crossroads. This was 2020 and the tech world was obsessed with chasing unicorns, but I wanted something different.
Something sustainable.
I spoke to the people I respected in Silicon Valley. And declared I wanted to build cash-flowing businesses and raise $0 of VC.
They looked at me like I had three heads.
“You’re going backwards,” they said.
“You’re wasting your time,” they warned.
“You’ll startups will eventually get crushed by VC-backed competition.”
Damn, lol.
But I was tired of my fate hanging on a “yes” from VCs in Palo Alto. I craved control over my destiny.
So, against all advice, I started Late Checkout, my holding company.
It was profitable from day one – a stark contrast to my WeWork experience and a rarity in VC land.
My goal – scale internet businesses powered by community, and on our own terms.
The journey wasn’t easy. We burned through millions and made more mistakes than I care to admit.
But we persisted, and gradually, we cracked the code on scaling SaaS, marketplaces, and agencies.
We discovered that the real power lies in building engaged audiences, fostering tight-knit communities, and finding creative ways to grow.
Take our agency, latecheckout.agency for example. You’ve probably never heard of it, but we’re pulling in clients at an average of $1 million per year creating the interfaces for lots of the AI products and non-AI products you use everyday.
We did it all without a dime of VC money. Just one little funnel that works every single day.
So, who am I looking for in a business partner:
Maybe you’re a solopreneur, and it’s getting lonely. You’ve built something great, but you’re hitting a ceiling.
Or, you’re running a VC-backed startup, but you’re dreaming of turning it into a cash-flowing powerhouse. (And maybe buying out your VCs – I can help with that.)
If any of these sound like you, here’s what I’m offering:
For businesses doing $500k-$5M, we could acquire a stake and scale it together.
This isn’t a distant, “call me quarterly” arrangement. We’re in the trenches with you, day in and day out, helping you build something truly remarkable.
This is the type of thing that sounds fun to me.
And might sound fun to you.
So here’s my ask of you:
1) If this sounds like you DM me on X (not LinkedIn it’ll get lost) and comment to this post. Ill respond to the most interesting ones
2) If this isn’t you, all good. Like always, I’ll share my learnings along the way.
It feels like internet startups are at a crossroads.
More and more are choosing the non-VC route.
Id love to work with you.
