The Top 5 Things I’ve Learned from Angel Investing

Some day, I want to look up at a big billboard in Times Square and say, “I knew that company when it was three people. And I saw what it could be.”

But how do I get there?


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I’ve been investing in early stage startups for 15 months today. I went from knowing absolutely nothing about the field to a portfolio of 13 companies.

Here are my top lessons so far:

1) Pay close attention to margins and scalability. Pure software businesses can scale easily.

For businesses that sell physical products, it’s much harder. It’s tough to sell 10 times as many physical goods as you did last year.

In today’s supply chain hell, it may be hard to even find the goods!

But strong software businesses can grow at warp speed. It’s no wonder that all the biggest winners in startupland are pure software businesses.

2) Build relationships with top investors. I don’t know for sure who will find the next billion dollar business.

But I have a pretty good guess of who it might be: someone who has found one before!

Build relationships and co-invest with investors whose track record is strong. They have the great dealflow you need.

3) Look at lots of deals. I look at 100-200 deals a month.

I choose one.

Look at lots of deals from top investors. This will give you a good idea of what the best companies in the market are right now.

Those are the companies you want to be in.

4) Help founders. This not only helps your existing investments, it builds your reputation in the industry.

The stronger your reputation is, the more good deals will come your way. Plus it’s fun!

What each investor has to offer is different.

I’m best at finding new investors for startups. But other angels might excel at marketing advice, product design or something else.

5) Always keep learning. More than anything, I learn by looking at deals and making investments.

There’s no substitute for actually doing deals, even if you make a few mistakes.

Consider them tuition! It’s a lot cheaper than business school.

I also talk to smart people, read books, and listen to podcasts that teach me more about the industry.

There’s always more to know, and it’s always changing!

Here are some great resources:

Angel by Jason Calacanis

This Week in Startups Podcast

The Power Law by Sebastian Mallaby

Venture Deals by Brad Feld and Jason Mendelson

Bottom Up by David Sacks

Lenny’s Newsletter

This is a field that can be learned. Dig in, find great information, and learn from experience!

If you’re interested in technology and business, you’ll find it very rewarding! You have a small hand in helping create the future.

What questions do you have about angel investing? And how can I improve my process?

Leave a comment at the bottom and let me know!

More on tech:

The Power Law (Part One)

Talking Startups and Today’s Fundraising Pullback

How to Write Investor Updates

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Photo: “If God Will Send His Angels” by just.Luc is licensed under CC BY-NC-SA 2.0.

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