The Three Types of Founders
Insiders, Storytellers, and Redeemed Crashouts.
After years of building startups and meeting thousands of fellow founders— one thing’s for sure: founders are interesting.
But over time, you begin seeing patterns—not just personalities, but archetypes.
There are 3 types of founders that almost every founder can be consistently grouped into: Insiders, Storytellers, and Redeemed Crashouts.
And knowing which one you are (and who your co-founders are) can mean the difference between startup magic and total misalignment.
1. The Insiders
Insider founders come from stable families, elite schools, and high-prestige jobs.
They know the jargon, the unspoken rules, the pipeline from sales to support, and often have deep networks within tech and venture capital.
But every superpower has a catch. Insiders sometimes believe too strongly in chasing “hype”.
See: e-commerce in the 1990s, green-tech in the early 2010s, AI agents in the 2020s.
Yet don’t underestimate their value.
Insider founders will often close deals that other teams can’t even pitch — simply because they “get it” and have the right background.
Whenever you hear about a “Stanford dropout prodigy who’s now building AI climate tech,” you’re looking at an Insider founder. Investors love betting on them because they’ve already passed the “IQ filter” elite universities have in place, and these founders speak the right language.
Famous Insider Founders include:
Larry Page & Sergey Brin – Built Google while finishing PhDs at Stanford. Their academic credibility and insider knowledge helped them raise money and recruit early talent.
Mark Zuckerberg – Harvard dropout who created Facebook. Used elite connections to raise early capital and gain credibility.
Bill Gates – Dropped out of Harvard to build Microsoft. Already deeply embedded in the computer science scene and well-connected within early computing circles.
Patrick & John Collison – Irish-born founders of Stripe. Both dropped out of MIT and Harvard after gaining traction. Came from a background of success in academic competitions and early tech ventures.
Most YC Founders – Many are alumni of top-tier universities and tech companies, well-versed in startup culture, and trained to pitch cleanly and build fast.
2. The Storytellers
Storyteller founders are hype machines, vision-crafters, and live off attention.
They dominate Twitter, TikTok, stages, newsletters, and podcasts. Storytellers aren’t usually technical, but they’re master communicators who bring excitement and rally support. Even in crowded markets, they make companies stand out and bring in tons of customers.
But they also come with risk.
Storytellers can overpromise, underdeliver, and burn their audience if the product doesn’t match the pitch. If a TikToker promotes a broken product to their massive audience— the backlash can be swift and brutal.
World-class Storyteller founders include:
Adam Neumann – Co-founder of WeWork. Turned a commercial real estate company into a “tech unicorn” through raw charisma and bold vision. Raised billions without sustainable fundamentals.
Naval Ravikant – Co-founder of AngelList. Grew a cult following with tweet-sized philosophy and sharp writing. Positioned himself as the sage of Silicon Valley.
Peter Levels – Indie hacker behind Nomad List and Remote OK. Turned solo building into a media brand by sharing his journey in real time.
Roy Lee – Creator of Interview Coder and Cluely. Built a massive social media presence teaching how to cheat software engineer interviews and now building Cluely.
3. The Redeemed Crashouts
Then there’s the third type of founder — the Redeemed Crashouts.
They often come from untraditional backgrounds and are fiercely independent— often “dropping out” of traditional society for years at a time.
Crashouts are tinkerers, risk-takers, and obsessives.
They may have missed the Ivy League pipeline, but they make up for it with pure grit and technical depth— these founders don’t care about anything but building products people love with their bare hands… and often spend years doing so “off the grid”.
Their technical knowledge is deep— but they often spend so much time building alone, they forget they are building for other people.
These founders tend to be high-risk, high-reward. They make up the smallest percent of VC-funded companies, but when they hit, they hit hard.
Famous Redeemed Crashouts founders include:
Palmer Luckey – Built Oculus VR out of a trailer at 16 after dropping out of Cal State Long Beach. Sold to Facebook for $1B. Now runs Anduril, a $30B+ defense tech company.
George Hotz – Known as the first person to jailbreak the iPhone. Later founded Comma.ai, an open-source Tesla rival, and TinyCorp, a GPU optimization company. Brilliant, eccentric, and totally self-made.
Jan Koum – Co-founder of WhatsApp. Grew up poor in Ukraine, dropped out of San Jose State, and built one of the most successful messaging apps ever. Sold to Facebook for $19B.
Markus “Notch” Persson – Creator of Minecraft. A self-taught programmer who dropped out of high school and later released Minecraft as a side project— eventually sold Mojang to Microsoft for $2.5B.
Chris Wanstrath – Co-founder of GitHub. Dropped out of college, worked odd jobs, and eventually helped build the backbone of open source software. GitHub sold to Microsoft for $7.5B.
Why It Matters
After years of building startups and meeting thousands of founders — one thing’s clear: people build companies, not pitch decks.
And when you zoom out far enough, almost every founder falls into one of three archetypes: Insiders, Storytellers, or Redeemed Crashouts.
Each type has different advantages — not just in personality, but in fundraising, team building, go-to-market, and even which business models are viable for them.
Some founders can raise a $5M pre-seed on a slide deck. Others have to ship a working deep-tech product and grind their way to revenue. That’s not about fairness — it’s about founder positioning.
Insiders win trust.
Storytellers generate attention.
Redeemed crashouts build from technical depth.
If you don’t understand your type, you might pursue a strategy or idea that simply doesn’t fit you.
Because in the end, startups aren’t just about product-market fit.
They’re about founder fit too.