Frequently Asked Questions

What is In Small, Out Big, exactly?

A plain-English, slightly snarky Substack for everyday investors who want to understand the startup game before they decide to play. “In Small” means investing with $500 or less. “Out Big” means getting back 50, 100, 500 times your money or more. (No guarantees, btw.)

Most of the posts are short, some are very short, and some have math. But give it a shot, I think you’ll like it even if you have no intention of ever putting a dime into a startup.

Why invest in startups at all?

Because the returns can be life-changing. And because individual stock picking and market timing with your buddies and your broker can be just as risky. Ditto the bets you make on FanDuel or Kalshi. Unless of course you have inside information, in which case I don’t judge you for using it. But the Feds might.

And yeah, even the mutual fund investing you do in your 401K or IRA has risk – the market could be taking a crap, for example, right around the time you want to retire.

On top of all of that, everyday investors have zero influence over the outcome of publicly-traded or institutionally-managed investments. Angel investing groups like AngelList, StartEngine or 99% Angels, on the other hand, can typically get an audience with the founders and managers whose private companies they placed their faith (and money) in.

If I don’t want to invest in startups, is there any reason to subscribe?

Yes. Because thanks to recent regulatory changes, at some point someone is probably going to try to sell you a private company investment - if they haven’t already. And unless they’ve been in that business for at least the last 10 years, your broker, even your financial advisor, has no idea how to do it right.

Why should I NOT invest in startups?

Everyone wants to make f-u money on their investments, right? But look, DON’T invest in startups if all the money you make right now goes toward rent and food. I suggest you need a better job or at least a cheaper place to live, so I would work on that first.

And DON’T invest in startups if you’re under age 40 say, and aren’t maxing out your 401K. I know that’s bo-ooring but it’s still the best way to take advantage of the tax benefits you get from Uncle Sam and your employer.

Finally, DON’T get into angel investing if you’re out to make a quick buck. The startup game requires patience, because you may not know if you’ve made a good investment for 3-5 years.

Isn’t startup investing only for the wealthy?

They’d like you to think that, but it’s simply not true. Startup investing is more accessible for everyday investors than ever before.

Yes, the 1% see most of the moon-shot opportunities first, and yes, the 1% have friends in private equity who keep their research to themselves. But the big guys don’t have a lock on promising startups, and if you read In Small, Out Big, that’ll give you a friend in private equity.

If I just want to just start investing, what are my choices?

Sign up for AngelList or WeFunder or Kickstarter or any of the dozens of other platforms offering entry into the startup world. Just remember that for the most part, they serve companies first, because that’s who pays them, and investors second.

If you’re looking for a truly independent group that serves only its fellow investors, take a look at the 99% Angels, a growing community of regular folks pooling their funds and brain power to make smart startup investments together. People who believe the next unicorn shouldn’t be reserved for the 1%.