How did I break into Investing with no experience and no network? How can new Angel investors get started?

I dug into these topics and more in a new interview with the team at PIN. Here are a few of my favorite moments…

How I Became an Angel

I learned about Angel Investing from a wonderful book:

I came across the concept of angel investing, and after reading Jason Calacanis’s book ‘Angel,’ which offers a practical guide to investing in startups, angel investing didn’t feel like a ‘mystery’ anymore. 

Jason’s book tells you everything you need to know about angel investing, in plain English. If you’re interested in investing, your first job is to read this book.

One, Small Problem

After I read Jason’s book, I was itching to place some bets. One, small problem: I didn’t know any startup founders or investors!

In the beginning, I lacked connections in the startup world, but I gradually expanded through syndicates and online networking. 

I started with Jason Calacanis’s syndicate, and from there, my network grew over time. While I occasionally engage in cold outreach, most of my investments come from inbound sources – whether directly to me, through other investors, or investment groups.

Building a Network

For any angel, Jason’s syndicate is the best place to start. I wound up joining almost 100 other syndicates as well.

I haunted just about every New York City startup event. You can usually find me near the free food.

Each person I met introduced me to 3 more. Soon, my contacts were sending me great deals.

A trickle of deals became a flood.

How Can I Deliver More Than Money?

Anyone can write a check to a startup. I stand out by being as helpful as possible without getting in the way:

I review their investor updates closely and address their specific asks. Occasionally, I’m able to provide assistance, like connecting them with resources or experts.

Recently, I even helped one of my successful companies find a head of marketing, which is a crucial hire for them. It’s gratifying to contribute in a meaningful way.

What I’ve Learned: Markets and Diversification

Now that I’ve been investing for 2.5 years, I’m beginning to understand what makes an investment successful. Above all, I focus on the market:

One important lesson is the significance of focusing on the market. A great product in a suboptimal market can limit growth potential. It’s crucial to choose business models that can scale effectively…

No matter how good the founder or vast the market, most startups fail. This is why I never bet more than I can afford to lose.

If you’re new to angel investing, start small. Invest as little as possible in as many companies as you can.

My advice would be to avoid putting all your capital into a single startup. Instead, spread your investments across multiple opportunities to reduce risk. Angel investing is a long game, and building a diversified portfolio increases your chances of success.

Wrap-Up

Finally, as we exit one hype cycle and head into a new one, I urge you to think for yourself. Don’t just do what someone else is doing — not me, not Jason, not anyone.

…one trait I value is the ability to think independently. It’s essential to avoid the herd mentality and make decisions based on your own judgment.

Thanks so much to the team at PIN for getting this amazing conversation together!

What questions do you have about angel investing? Leave a comment and let me know!

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