I doubled down on angel investing over the past 6 months.

Invested $600k in the past 6 months into 8 startups... for anyone interested in startup investing - a few standout companies and spaces

INDIA - 2 of the co's were in India, I believe both will be $1B+

@mydukaanapp is building shopify for india (3M+ stores created in 5 months)

@wiseapplive gives teachers a digital classroom (to teach & earn money) that works even on 2G phones. 5x'd growth since we invested.

Remote Work -

I think there is both a huge opportunity AND a ton of garbage in this space right now.

Because 30M engineers all simultaneously experienced the pain points of remote work, and started building tools to solve it.

Lots of crap, but a few gems..

Remote Work

@usebubbles - I take like 1000 screenshots a day, and then do 10 steps to show it to my team.

It's janky and requires a ton of back & forth. Bubbles makes this experience so smooth. It's one of those tools like Figma.. once you use it, it's hard to go back.

@DashworksAI - put a big check ($250k) into this one. Every remote co needs an intra-net (to easily search for files, people, or read announcements).

Idea been tried a million times, but nobody's cracked it. Like every work chat tool before slack. I think they have a shot.

At Home Fitness is also blowing up due to COVID.

@myYogaTeacher is a company we found that is doing at home yoga instruction. Super clever. They match you with yogis in india so you can get 1:1 classes from an expert, at half the cost of a group class. Better + Cheaper = Win.

@FitnessAI_ is a co I invested in because @jakemor is a A+++ founder. It's an app for people who want to build muscle faster.

Personal Trainer = $100 per HOUR
Fitness AI = $100 per YEAR

Uses whatever equip you have at home.

Better + Cheaper = Win.

For both of those companies, they're already doing 7 figures a year in recurring revenue...How do they get to $100m+/year?

They need roughly 1M customers.

65M americans have gym memberships.

Will 2% of those people have a membership to a digital fitness app? I think so.

And sometimes I just close my eyes and invest:

eg. Bet on serial founders who've built $1b companies before (eg. @gaganbiyani 's new ed tech company)

or

Join later stage deals of co's that have escape velocity and the founder is friendly & lets me in (eg. @italic)

Now lets do some Good Decisions / Bad Decisions:

GOOD = TEAM

@zlwaterfield the guy is a monster! great scout. I think he referred like 20% of this year's YC batch

@RomeenSheth super deep, strategic thinker. I'm impulsive & gut driven. He is logical & analytical. Great balance

BAD Decisions. I've got 4

1/ I took a "wait and see" approach a few times, and ended up investing later, at a 2-3x higher price point.

Better to be early & be OK w/ being wrong more often.

2/ I wish I owned more of each company. Right now avg ~0.8% , going to aim for 1.5-2%

3/ I created a rolling fund so any accredited investor can invest alongside me.

We hit $2.5M really fast (3 weeks) so I panicked and cut it off at 75 investors.

I shoulda kept it open to get to the 99 max cap allowed.

Going to re-open in Jan to fill the last 24 spots!

4/ SECONDARIES - I really wanna own secondary shares in @stripe, @coinbase , etc.. But haven't ever done this before and need to learn how to do it properly. plz teach me if you've done this a bunch.

thank you to all the founders who let me invest in your companies. Startups are one of the only asset classes where it's not just the investor who picks the asset...the asset also picks the investor.

The game theory of that ^ dynamic is fascinating.

At the end of the day, startup investing is like an MBA that pays you.

You get to learn about business & technology, while making money (aiming to ~4-5x our money in 10 years)

MISSES & WISHES:

Companies or spaces I want to be in - but was late to the party:

- Collectables: @OnRallyRd , @RealWhatnot , @MasterworksIO

- FinTech: (eg. @pipe)

- ClimateTech

- Vertical Labor Market ( @rigup, @JoinIncredible

- AI Girlfriends ( @MyReplika )