Want to Do a Startup? Consider a Job at a Rocketship First.
After doing 10 startups, I'm not sure I could go back to working for someone, but working at a "rocketship" company like @OpenAI or @Figure is a great option for someone just starting out.
Why?
Great experience
Great money
Super fun
Resume builder (especially for raising)
Network / Friends for life
Here's a quick story of working for the hottest .com from the 90's tech bubble that no one has heard of. You think WeWork on Netflix was crazy? Trilogy was that on steroids.
The Interviews
As a senior graduating with a CS degree in 2000, there were 4 hot companies: Microsoft, Amazon, Microstrategy (yes, THAT Microstrategy), and a company in Austin called Trilogy.
My interviews were a spectacular failure.
At Microsoft, a guy named Tuna asked me to design an alarm-clock for the blind. I heard him say "blinds," so I proceeded to describe a Rube Goldberg-style machine to let the sun shine in at the right moment. I tried a quick recovery by joking the same thing could work for the blind. Oh yeah, blind, not deaf.
Trilogy had recently been banned from Stanford because they were giving away lavish ski vacations & even sports cars to top recruits. For my interview, you know those comma-separated lists people put at the bottom of their resume? Skills: SQL, Javascript, etc. They took each word and asked me PhD-level questions about each.
At dinner, a hulking 6'9" manager asked me if I played basketball. "A little." He said if I could beat him in 1-on-1, the job was mine, but if I lost, I'd be out of consideration. The level of my interview disaster tempted me, but I had to pass.
I was lucky enough to have one of my classmates who was a star at Trilogy vouch for me post-interview, and I snuck in.
The Training
For three months they crammed 120 top grads into a giant open office. We drank insane amounts of Starbucks Frappuccino's and pop tarts from the free kitchen (unheard of at the time) and many people literally slept under their desk as a sign of dedication.
The projects were intense. We all had to pitch the CEO, 40 under 40 richest man— Joe Liemandt, on a new $5M+ business idea (which seemed impossible in those days). We considered a digital wallet but landed on "the Box", an AI companion that sat in your house and you could chat with & ask questions about the weather. (Zack, we were just a few years too early).
But the real intensity came from the culture. With an emphasis on cult.
We were graded not just on our technical skills but on our ability to drink the kool-aid. For example, the trip to Vegas— all expenses paid plus a gambling budget that I had to either lose or double. This culminated in L2K (lose $2,000), where 36 of us had to cover every spot on a roulette table and 1 person won $72k. I passed, but 3 of my buddies won, secretly splitting the risk.
Or the time I watched my CEO gamble his Jaguar against $50k on who could chug a beer the fastest. The employee, a giga-chad, won and proceeded to slam down the beer glass, breaking both it and his hand, while telling Joe to go F himself. This was a typical Thursday.
The Company
So what did this company actually do? More or less it would go into Fortune 500 companies and ask them what they needed, then tell them we could build it for less money and in less time.
Then we would scramble to make the damn thing & prevent it from breaking all over the place. Quality & customer service was non-existent.
Unsurprisingly, the company kept making bigger and bigger bets with spinoffs like CarOrder.com. And even less surprisingly it collapsed when the .com bubble burst about 8 months after I joined.
The End
If you can manage to land a job at one of these types of places, like early FB / Google or OpenAI / Figure, I would 100% recommend it.
Not only for the intensity but also for the people you meet—the best of the best. You'll make lifelong friends & go off and start new companies with them afterwards. You'll build your resume. And also have a great time.
Epilogue
Trilogy is long forgotten. But there's an interesting twist...
Eventually the 1,500 people at Trilogy all had their jobs outsourced until it was left with only Joe & 2 other people. They now buy & gut enterprise software companies and quietly still make boatloads of money.
