investor stories

Hustle Fund's Co-Founder shares lessons learned from 700 deals

For first-time investors looking to get their foot in the door, angel investing (small checks of your own money, rather than a fund of other people’s money) can be a great way to get started.

And there’s no better brain to pick for advice than Hustle Fund Co-Founder and General Partner Elizabeth Yin. Over her years as an investor, she has backed over 700 companies and looked at a whopping 40,000. And prior to that, she was a founder herself who successfully exited.

A while back, she sat down with Haley Bryant, a pre-seed investor at Hustle Fund, to take questions from a community of aspiring angel investors. Here are some nuggets of wisdom from that chat.

When is the right time to start angel investing, even if it’s just one check a year?

There are two camps of angels. One camp is people who want to be super active, get better at investing, and raise a fund some day. Another camp is people who have a bit of money, want to make an impact, or pay it forward.

If you’re in the first camp, you need to have a concerted pool of money—5 or 10K a year is enough—and you need a lot of time. Angel investing or VC is a comparison game. Every company looks great in isolation, but if you have 100 companies, who are the 5-10 you’re going to pick? You need to have the time to look at at least 1,000 deals per calendar year so you can write a 1K check in 5-10 companies that year.

On the flip side, if you’re doing it more passively, you may not get good at it. But it could be a strategic choice: you may lose a couple thousand a year, but you can say you’re an angel investor and meet the right people.

What if you want to be active but 5-10K is still too much?

A cheaper option if you’re in the serious camp is to volunteer to mentor at an accelerator. Accelerators always want mentors, and nobody has the time. Mentoring allows you to see a lot because every batch is pretty huge. If you do a few batches, you get a lot of reps. You don’t have to signal that you’re an angel investor, but if you do see a really great company out of the 50 in a batch, you can write that small check.

What attributes in founders correlate with actual investment returns?

What I have noticed is that up and down markets happen every decade. Every founder has an up part and a down part of their journey that they have to navigate. The founders who are frugal, scrappy, and focused on putting resources on one thing tend to do very well. People who are spendy, don’t make the cuts they need to make, or are not scrappy or creative in how to pay for things tend to be ok in an upmarket, but in a downmarket, that’s just tough...

What’s your take on investing in hype markets such as AI?

It’s really important for companies to be differentiated, not just from competitors, but all the other solutions out there. When I’ve invested in companies in crowded spaces, even with great founders, it’s really hard. The cost of customer acquisition is high, because you have to combat all the alternatives. I tend to look for greenfield ideas. This tends to mean areas that are new, geographies that are new, or demographics that are new. If you’re early in the hype cycle, the CAC is low. But if you’re two years too late, it's just too expensive.

How has your investment criteria changed over time?

I used to believe as an investor that the founding team is all that matters. I no longer believe that. Of course, a great team matters, but an amazing idea matters way more. There are a number of companies that have a really strong product-market pull that are run by people whom I would not consider to be the best founders. But they do extremely well because customers love their product. They can make a ton of missteps and people love it so much that they’ll continue to stick with it. For example, there was a lot of management changeover at everyone’s favorite social media app, and yet that app continues to run. Companies that have a lot of market pull also attract a lot of investment naturally. You have a lot of capital to work with and can afford to make mistakes.

How do you approach playing the numbers game and making a lot of investments?

You do need to make enough investments—I would say 50 minimum. When I think of my initial investments, they weren’t all great. So you need to make a lot, but they don’t have to be this year. They can be over the next 10 years. If you have a handful you’re doing each year, that gives you enough data points, and you have time compounding on other investments so you can learn from those. On the flip side, you do want to build up your dealflow such that you are making the best handful of investments that you can. So you should be seeing at least 100 companies a year—and ideally more than 100—and back into no more than a handful. I’ve done 700 deals, but I’ve also seen more than 40,000 companies.

With so many companies, how do you manage the fear of missing out on the next unicorn?

You accept that you will miss some. You have to see a lot to do some. If you didn’t see it, you never had that opportunity, and you need to improve your dealflow. Ultimately you’re going to miss out. That’s just life.

This article was written by Elizabeth Yin, our Co-Founder, General Partner, and lead hippo enthusiast at Hustle Fund.