The guide for people who weren’t born into the club.
In Small, Out Big explains startup investing in plain English, for people who want to understand the game before deciding to play. The wealthy have always had access to this info, while everyone else gets buzz words and the impression that the startup world is for insiders only. It isn’t.
A soup-to-nuts primer for new angel investors.
Written by a real human being, with real investing experience—not a chatbot. Read it and you’ll know more than what most 1 Percenters know about how the startup game works.
In Small, Out Big explains startup investing in plain English: how opportunities are evaluated, how deals are structured, why most startups fail and what can make the rare winners so valuable.
It's not required reading before you can join the 99% Angels. It's just deeper education for folks who want to understand the game before they decide whether or not to play.
Not your typical finance textbook.
“…startup investments belong in your portfolio, right alongside your stocks, bonds and X-Men comics. Not just for shots on goal for huge, tell-your-boss-to-shove-it returns. For optimal diversification.”
“Startup ideas are like buttholes. Everyone has one, and no one thinks theirs stinks.”
“As I thought more about what qualities make a great startup founder, I had an uncomfortable realization: The best founders have a lot in common with serial killers.”
“Yes, repeat founders are lower risk. But in my experience, first-time losers are better bets than first-time winners. If you’re never burned, you never learn.”
Someone who's spent decades around the game.
Rich Ingrassia started his working life consulting to AT&T, Disney, Sony and the like. After that, he became an off-Wall Street, Wall Street analyst, writing research for more than 20 years on entertainment companies like Netflix, IMAX and WWE.
In 2013, he helped launch Digital Offering, one of the first equity crowdfunding platforms, where he was involved in the early rounds of micro-investing app Acorns and others.
In 2018, Rich co-founded Wheelhouse Digital Studios, a services-for-equity venture fund. Today, companies in the Wheelhouse portfolio are together worth more than $10 billion.
He is a graduate of the University of Notre Dame and got a master’s degree in journalism at Northwestern. He splits his time between the Minnesota lakes country and Charleston, South Carolina.
$40 annual Substack subscription after the first few posts.