Real-Life Angel Investing Returns 2012–2016

I have been doing angel investing since 2012 after the Facebook IPO. Since then I have invested in more than 150+ startups. 50+ of them are direct investments where my name is on the cap table and 100+ are through SPV (special purpose vehicles) and crowd funding platforms like AngelList, FundersClub and MicroVentures. When I first started, there was not a lot of public data about the returns of angel investing. 8 years later, there is still not a lot of public data about angel investing returns. Chances are returns vary a lot since the top 10% of the investments determine the performance of an angel portfolio. Therefore, the variance of the returns is quite high.

After all these years, I believe stronger that angel investments as an investment class is worth pursuing if you have the money and the time. When you invest in a startup, the money directly goes to the economy to build up a business, to create jobs and to actually contribute to the trickle down economy. On the contrary, investing in the public market is simply buying stocks from other investors. The money doesn’t directly go into the economy. In addition, I believe angel investors can earn better returns than the public market through diversification. We will get to that later but let me start with sharing my real-life angel investing returns.

The Methodology

For the return calculation, I am including the investments made between 2012–2016 to give enough time for the companies to mature. It typically takes a company at least 5 years from founding to really snowball and break out. Every company I invested during 2012–2016 is at least 5 years old now.

I am only including companies that I either directly invested or invested at least $20K through SPV or crowdfunding platforms. I am not including the large number of small investments (average <$5000) because they are passive investments mostly through AngelList syndicates. I do intend to write another post about my syndicate and fund investments. All the investments listed here are investments I spent at least two hours vetting.

The following is the complete list of 39 companies (according to the criteria mentioned above) I invested during 2012–2016 and their current multiples. I am publishing the list here for transparency and accountability. I also want to demonstrate that people don’t have to invest in Uber or Coinbase to get good enough returns. I am lumping companies into groups if they haven’t achieve at least 5X markup. I just don’t feel it’s the right thing to do to point out in public that a company lost or is likely to lose 100% of my investment. Loss is part of the game. For companies that have been around for a long time but are not in a good trajectory to succeed (or failure), I marked them down to 10% of my investment amount. Chances are they are probably worth more than that from the revenue or EBITA perspective. But I am being super conservative for this study. I am assuming the same amount is invested for each company. In reality, it varies a bit but the overall return remains the same.

Breakout Companies

9 out of the 39 investments could be considered breakouts. They all generate $10M+ annual run rate. KiwiCo and Reddit generate more than $100M annual revenue already. Iterable and MatterPort are probably reaching $100M in the next couple of years. I didn’t have any insider information here. I looked up these revenue numbers through clever googling. Their aggregate multiple is 12.5 based on the valuation from the most recent financing round but they are all still growing like weeds with good unit economics so the more realistic multiple of 26.3 is probably still an underestimate.

My Breakout Investments

Other Companies

14 of the remaining 30 companies are still active. The aggregate multiple is 1.49 based on very aggressive markdown. The companies are:

WonderSchool(Soldsie), BackTotheRoots, Volta, PicCollage, Postmates, FundersClub, Indinero, Hapara, Women.com, BountyHunter, BoxC, Change.org, Microventures, Onera Commerce

16 of the 30 companies are realized. The aggregate multiple is 0.61 realized. The companies are:

Moxxly, meetup, Balanced, pic6 Studios, Flurry, Evertoon, MightySignal, Blue Bottle Coffee, LoveWithFood, LaunchTrack, Beepi, SlidePay, Freshplum, Shopgenius, Bento, Munchery

If you prefer to see the numbers in spreadsheets, please visit this google sheet for more number crunching.

The Investment Returns

It’s a bit hard to give one number for the returns as if they are factual. The reality is these investments are illiquid and it’s hard to pinpoint the exact outcome. But here are some estimates:

Using the conservative multiple of the breakout companies, the overall return multiple will be (12.5*9 + 1.49*14 + 0.61*16)/39 =~ 3.67

Using the realistic multiple of the breakout companies, the overall return multiple will be (26.33*9 + 1.49*14 + 0.61*16)/39 =~ 6.86

We don’t know where the final return is going to land but I will be personally satisfied with a 3X return and based on the estimate, it’s very likely the return will actually be much higher than that.

An interesting exercise will be to compare this return to public market returns. In particular, to compare this return to SPY and QQQ. To do that, I decided to calculate the public market multiple based on the return from January 1st, {Investment Year} to Dec 31st, 2019. The basic idea is that if I were to invest in the money in SPY or QQQ instead of company X at the time, what’s my expected investment multiple from SPY or QQQ? For example, the investment multiple of SPY and QQQ from 2012 would be 3.01 and 4.15 respectively and the investment multiple of SPY and QQQ from 2016 would be 1.71 and 1.91 respectively. Using this, the blended multiple of SPY and QQQ based on my investment timing will be 2.29 and 3.04 respectively. In any measure, my angel investments still do better. Again, if you are interested in crunching the number please visit the spreadsheet.

The Takeaways

I consider myself a pretty average angel investor. I don’t keep a high profile so my deal flows are probably not amazing. I didn’t invest in super hot companies like Uber or Coinbase. I was also really naive when I first left Facebook and really had no idea about running a startup or sales or marketing. I was an engineer so I know infrastructure, machine learning and full stack engineering. But that’s all I knew when I left Facebook. I have come a long way since then. I am somewhat amazed despite all these, I am still generating acceptable returns.

If you look through the breakout list, they are also pretty well distributed. It’s not like I only invested in breakout companies in a short timeframe. Every single year between 2012–2016 I invested at least one breakout. From the second half of 2015, I did slow down my angel investment pace due to a new child and a new job I took in late 2016. I picked up the pace again in 2020 and I have made 16 direct investments this year. I am pretty sure that at least one of them will become a breakout. But I will report back in 2025.

So why did it work? I am not going to pretend I knew Justin Zhu was going to be a startup superstar when he was pitching me about the idea of Iterable. I only chatted with him for an hour before deciding to invest. I also had no clue that KiwiCo could become so ubiquitous and my kids love them. When I invested in HealthSherpa, they were called rent.io and they needed to pivot the company to make it work. My point is I don’t think I have amazing judgment or anything. In general, I attribute the good returns to diversification and proximity to good startup founders. Diversification is achievable by investing in 10+ companies a year. Proximity to good startup founders is easier to get these days since everyone is making investment decisions through zoom. My definition of good startup founders is also pretty straightforward. I like founders who can clearly communicate, whose progress to invested capital ratio is high(aka scrappiness), who know what they are doing and who are super vigilant about their spending. I shy away from founders who don’t seem to be sober and who seek attention and external validation too much. I can confidently say all the founders I directly invested made earnest effort to make their company work regardless of the outcome.

It’s also worth noting that 6 out of the 9 breakout companies I invested have female, immigrant or diverse founders vs 21 out of 39 all investments. It’s well documented that the FID founders outperform the non-FID founders. But I could tell you that systemic bias still exists very strongly today and I see my willingness to invest in FID founders as an edge.

Recommendations

Would I recommend angel investing as part of your portfolio strategy? If you can put in the time and money to invest in a large number of investments and don’t need liquidity, I highly recommend it. In addition to generating good returns and investing money directly into the economy, the satisfaction of seeing the hardworking entrepreneurs building amazing companies from scratch is unparalleled.

I listed all direct investments since 2020 at brightercapital.com If you are a startup founder looking for investments or a fellow investor wanting to exchange notes, do reach out!

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