So you want to be an angel investor. If you are a regular person with no edge and no connections, I don't think angel investing is worth the risk.
After 21 years of doing some angel investing, I believe you are much better off investing in an angel fund rather than investing in individual angel investments. Just say no to angel investing!
Let me share with you an angel investing example I had in a gin company back in 2010 and the outcome. To clarify, angel investing is the early stage of venture capital. However, the definition of angel investing has stretched from pre-see investing to seed investing to even Series A round investing.
Angel Investing Is Difficult
After 10 years, my $60,000 investment in a private gin company finally paid dividends.
Initially, given the company was sold for about $49M after expenses and I had invested in the company at a $10M post money valuation, I was thinking I had made a ~3X return ($180,000). Since over time shareholders get diluted with subsequent funding rounds, I thought that was a reasonable assumption.
Well it turns out I didn't come close. Instead, here's what I got:
Gross Proceeds: $98,425.88
Federal Withholdings: $0
State Withholdings: $6,523.82
Net Proceeds: $91,902.07
What the hell!? After almost 10 years, with $98,425.88 in gross proceeds, I only made a 64% return on my money (1.64X). Further, I had ZERO liquidity and lost hope for years that I'd ever get my $60,000 back.
Doing the math, I only made a 5.1% IRR, barely better than my guaranteed 4.1% 7-year CD that just expired.
So where did all the money go since the company was sold for 5X what I bought in for? Based on an internal document I received, we had to pay a lot of banker, lawyer, escrow, accounting, and general administration fees.
We also had to pay severance packages to all the employees (rightfully so) who were made redundant when the parent company took over. But there must be something else I'm missing, which I'll investigate further.
Got Away With A Close One
Despite the missing money, I consider myself LUCKY to get any money back because most startups fail miserably. Before the buyer announced the acquisition, I had already written off the $60,000 because shareholders had never gotten a dividend and the growth target dates kept on getting pushed out.
My concern was the company would turn into one of those zombie companies with just enough growth to maintain EBITDA break even, but never enough growth to become an attractive acquisition target.
When the purchase price was announced, my write-off expectation transformed into greed. And now with the payout, my greed has turned into selfish disappointment.
Why You Should Not Angel Invest
Now that the stock market has gone up every year since 2009 (except for in 2018 and 2022), everybody thinks they're investing geniuses. I've got so many people asking me whether they should invest in some random, moat-less private business. You just can't lose if you put money to work, especially if you're under the age of 35!
This is exactly what I thought in 2007 when I invested $60,000 in the gin company and bought a $715,000 condo in Lake Tahoe. Then the world came to an end.
Here are the reasons why you shouldn't angel invest:
1) You have ZERO edge.
The other day I had sashimi and sake with a Sequoia Capital partner. Sequoia Capital is one of the best VC companies in the industry. It has made billions backing Apple, Google, Oracle, Paypal, YouTube, Yahoo!, and Whatsapp.
The partner said Sequoia shoots for a one win, seven loss hit rate. In other words, to follow Sequoia's ratio you've first got to be willing to make eight bets of similar size. Further, you've absolutely got to be willing to lose money on 87.5% of your investments and hope that one deal is at least a 10 bagger!
The best VC firms get all the first looks. They have some of the brightest people spending 50+ hours a week reviewing company after company. Oftentimes they see information about competitor companies that enables them to evaluate who will likely come out ahead.
They also talk to their fellow VC industry colleagues about what other companies and other VCs are doing. In comparison, you and I get no looks. Instead, we only get the companies that have been rejected by the VCs. Talk about an unfair advantage.
2) Your money is more sacred than other people's money.
Being a VC is the best job ever because you get to make a $250,000 – $400,000 salary and make investments using OTHER PEOPLE's money! If your investments turn sour, who cares? You still get paid your base salary for the 8-10 year life of the fund. If your investments do well, you get to earn even more money off other people's money in the form of carry.
As an angel investor, you're putting your own money on the line. In order for me to follow Sequoia's model, I would have to personally make an investment total of $480,000 at $60,000 each in eight unproven companies. Other VCs with worse returns have a 1:9 win:loss target. In other words, I'd have to make a $600,000 investment to try and make money.
Even if we're allowed to invest only $25,000 per deal, most of us won't be willing to risk $250,000 worth of capital in venture.
3) Your stake will be diluted away.
As a minority investor, you have no say in management decisions or funding rounds. If the company starts getting desperate for cash, they may offer sweetheart deals to future investors at your expense. One such sweatheart deal is called liquidation preferences.
For example, assume a venture capital company has a 2X liquidation preference after investing $1,000,000 for a 50% stake in the company. The founders own 30%, and you, the angel investor, owns 20% after investing $100,000. If the company is sold for $2,000,000, you might think you'd be getting $400,000 back.
In reality, you'd get $0 back because the VC gets paid 2X their initial $1,000,000 investment during the liquidity event. Meanwhile, the founders also get $0 back as well!
Just realize that whenever your private company raises a new round of funding, your stake will get diluted by 20% on average. See my post on career advice for startup employees.
4) You have zero liquidity.
Goodness forbid you need the money to cover an emergency during a typical 8-10 year holding period. So sorry! You will never get your money back unless there is a sale or IPO. And given ~90% of companies fail, and 9% of companies end up barely staying alive, you will likely never get your money back even if you waited 50 years.
At least with public investments in stocks and bonds, you can get your money back within three business days.
Now in 2023, even accessing cash may pose problems after the bank runs Silicon Valley Bank, Signature Bank, Credit Suisse, and likely many others. Make sure you have enough big banking relationships to keep you safe and liquid.
it’s looking more and more like early stage start ups will have a very difficult time navigating the future going forward. Funding will be much slower and the startup terms will be tougher.
5) The returns aren't even that great!
For all the sexy talk about angel and venture capital investing, for the typical VC and angel investor, the return is truly dismal. We're talking median 0%-2% returns a year from 2001 until now. The mean (arithmetic average), however, is more like 8% during the same time period due to the massive success of the top VC firms.
Check out some great charts that demonstrate my point.
The top 20 firms (out of approximately 1,000 total VC firms) generate approximately 95% of the industry’s returns according to Betterment, the leading digital wealth advisor today. Further, nobody can participate because the funds are way oversubscribed.
Here's an old chart that shows how VC returns were awesome in the 1990s, and have since fallen to ~0% in the 2000s due to too much money chasing too few deals. The lines continue to hover around the 0% return level until 2017.
Here's another chart showing that 64.8% of US Ventures return just 0 – 1X your money over a 10 year period. In other words, best case scenario for 64.8% of the VC funds, you only get your money back (1X return)!
Micro-VC Performance
Here's another chart that shows the top quartile and bottom quartile performance of micro-VCs, funds that are $50 million and less. Notice the wide range of performance, with the median performance coming in closer to 10%.
Not bad, but nothing special compared to the S&P 500 return. With the global pandemic hitting in 2020, many more private companies will go bust due to a lack of cash flow and capital.
If you look at even “sure bets” like Uber, Lyft, and Airbnb, investing in these companies haven't turned out so well if you did after 2015.
Airbnb is the big shocker, when they had to raise money from Silver Lake Partners in 2020 at a $18 billion valuation after being valued over $50 billion at the end of 2019. Who would have thought there would be a global pandemic and months of lockdowns that would crush the travel and hospitality industry?
As investors, we just never know. Timing is so important.
Three Saving Graces For Angel Investing
Although my gross proceeds from my $60,000 investment is only $98,425.88, apparently I don't have to pay the full federal taxes on my $38,425.88 gain under the Qualified Small Business Stock (QSBS) Act.
Beginning in 2015, for the first time since its enactment in 1993, Sec. 1202 allows noncorporate taxpayers to exclude from federal income tax 100% of the gain on the sale of certain qualified small business stock (QSBS), limited to the greater of $10 million or 10 times the adjusted basis of the investment.
To qualify for the exclusion, five criteria generally must be met:
1. The stock must have been directly acquired via an original issuance from a U.S. C corporation (Sec. 1202(c)(1))
2. Both before and immediately after stock issuance, the C corporation's tax basis in gross assets did not exceed $50 million (Sec. 1202(d)(1));
3. The C corporation and shareholders must consent to supply documentation regarding QSBS (Sec. 1202(d)(1)(C));
4. The C corporation conducts certain qualified active trades or businesses (Sec. 1202(e)); and
5. The stock must have been held for more than five years (Sec. 1202(b)(2)).
Well what do you know? My investment in the gin company back in 2007 meets all these qualifications. All I have to do is pay California state tax, which I've done. But of course, there's a catch. My investment needed to have been made after 9/28/2010. So in reality, I only get about a 43% tax savings (see chart), which is better than a dumbbell on a toe.
The other saving grace of this deal is a performance bonus. If the gin company achieves several sales targets over the next several years, investors get to earn a 50% bonus on our returns equivalent. For me, that equates to an additional $49,213 of upside. I won't count on it, but it's nice to know it's there.
The final saving grace is that locking up $60,000 saved me from potentially wasting my hard earned money on something wasteful like a fancy car or an even more expensive vacation property. I had a lot more desires as a 29 year old than I do now.
Despite these benefits, I still don't think anybody should angel invest. If you absolutely must, you can take 5% – 10% of your investable capital and make some unwise investments to help friends and family. Just expect your money never to return.
Related: Recommended Net Worth Allocation By Age Or Work Experience
Brushes With Angels Of Death
As I reflect upon my investment, I was foolish to invest $60,000 in a 28-year-old first-time founder with no experience in the spirits business. But he was my friend and I admired his drive and hustle.
He told a great story: “We'll do to gin what Skyy did to vodka and blow the category up!” A more risk appropriate amount for me at the time would have been $25,000.
Now my friend, who is 38, is worth $5,000,000 – $7,000,000 before taxes and is taking a well-deserved break before starting a new venture. If you are a founder, and people are throwing money at you, take it!
Just make sure there are no nasty covenants in place. It's so fun to get rich off of other people's money. No wonder I like real estate.
To conclude, here are a couple more venture investments I was so close to making, but didn't, thank goodness.
Triggit
Circa 2011, I could have invested $100,000 in a company called Triggit, a Facebook ad retargeting company that was growing like crazy. I played poker with the founder all the time and at one point, my investment would have been worth ~$1,000,000. I was kicking myself in 2014 for not taking the risk in a business I knew pretty well as an online media business owner.
Then out of the blue in 2015, Triggit got taken UNDER by Gravity4. Employees got zilch, and I'm not even sure the founders got anything. Facebook decided to change the rules and made third party ad exchange providers irrelevant. Then the founder of Gravity4 ended up getting kicked out due to domestic abuse.
Bento Now
Then there was a company called Bento Now, an Asian food delivery company I was considering investing $25,000, also in 2015. I wanted a deal in exchange for helping promote their product, but they said demand was too great for them to negotiate.
It was run by an ex-blogger I knew who ended up raising ~$1.5M from several well known angels. Then one day in the fall of 2016, I was listening to the Gimlet Media Startup podcast (which eventually sold for big bucks to Spotify) and heard they had spent $70,000 more than they realized in one month! How do you do that? A few months later, the company shut down.
Given I didn't lose $125,000, does that mean I gained $125,000 and can therefore splurge on whatever I want?! Please say yes! Venture investing is seriously risky business. Don't risk anything you can't afford to lose. With my gross “windfall” of $98,425.88, I plan to do some more landscaping and save the rest for my Hawaiian dream house fund.
Empower Personal Capital
I invested about $10,000 in Empower Personal Capital, my favorite free wealth management tool and popular digital robo advisor in 2015. At the time, the valuation was for $500 million. The firm sold for $825 million plus $175 million in incentives to Empower Retirement in 2H2020.
This investment really wasn't an angel investment because I invested during the Series C round. I ended up getting $49,500 back. Not bad!
If you want to invest in VC, try and invest with a top tier VC fund instead. Funds like Andreesen Horowitz, Sequoia, Kleiner Perkins (new vintages), Benchmark, and so forth. The difficultly will be getting an allocation. These guys have much better track records and much better access to capital.
Angel Investing Alternative
I'd much rather invest in real estate, a tangible asset that provides shelter and generates income. Real estate is stickier on the way down and is often a defensive asset class during times of uncertainty.
Fundrise is the leading real estate crowdfunding platform today that is free to sign up and explore.
Another good real estate crowdfunding platform to check out is CrowdStreet. CrowdStreet primarily focuses on real estate investment opportunities in 18-hour cities, those cities with lower valuations and faster growth due to demographic shifts.
Thanks to technology, remote work from home, and high cost of living on the coasts, I expect there to be a multi-decade demographic shift towards the heartland of America.
I have invested $810,000 in commercial real estate across the country and plan to continue investing more over time. I'm much more comfortable investing in real estate than angel investing.
Wealth Management Recommendation
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I’ve been using Personal Capital since 2012 and have seen my net worth skyrocket during this time thanks to better money management.
Updated for 2022 and beyond. Angel investing is still popular, but I would limit your angel investments to no more than 10% of your investable assets. Instead, I would invest in a private fund (VC, VD, PE, etc) instead. These funds have much greater access than you or I.
I’ve invested in two early stage venture funds here in Australia. The incentives are that gains are tax free and you get a 10% tax credit (i.e. cash back from the government) for your investment. I’ve been invested in the first fund for a couple of years – I wasn’t an initial investor but am up about 60% on my net AUD85k investment. This is based on a couple of exits and the interim valuations on the other investments. So, it could go worse from here, but it looks like it will end up making money even in the worst case. It was an AUD100k investment formally but they are using the proceeds of the exit for follow on investments in the more successful companies.
So, I invested in a second fund. AUD 250k, 25% called so far. So, I was only investing about AUD 10k in each of the companies in the first fund and will now be more like AUD 25k. These seem appropriate risks for me (family net worth near AUD 5 million).
If everyone had your beliefs, or mine we wouldn’t have a functioning economy.
Thank f*** for Sequoia Capital and other businesses.
You’re not wrong on poor investment, high risk, but just think of the privilege it speaks to that you had 60k in your 20’s to invest as well as buying a house
Curious, why do you discuss privilege when this is a discussion on angel investing? Is there some type of privilege you have that is making you feel guilty?
I think we’re all quite privileged and we have to make the most of it. See: https://www.financialsamurai.com/your-wealth-is-mostly-due-to-luck-be-thankful/
I agree with Sam. Angel investing is suitable for institutional money not for individual, as your money won’t be diversified enough to adjust with the risks. Its better to invest in a fund rather into one business directly thats the way you can still help the economy grow.
Sorry, but I have to disagree about “never invest in startups.” That’s foolish advice.
Of course, if you don’t know what you are doing, you will lose your money. And it seems the majority of commentators here really had no notion of how find, analyze and then invest in an early stage company.
I could just have easily written the same thing about stocks or real estate — plenty of people have lost money in all sorts of investments. But just because one person is foolish doesn’t mean everyone has to be as well.
First, you need good deal flow. If you think you are going to find a good company at your local incubator, or your nephew who started a cool tech company, then you get all the problems you deserve. Finding a stream of good companies is a skill itself, and no, the best deals do not get pasted on Angelist or Gust, or come from your local university. You have to be plugged into a solid, trusted network of actual angel investors.
Second, you need to know how to analyze a company. Honestly, I’ve known people who spend more time researching their next car then they do a $100K investment in a company! And it’s NOT about the product! If you invest because you think the product is great, you will probably lose all your money. Mostly, it comes down to the management team — if the founder or entrepreneur has a history of starting and selling companies, and has strong ties to the industry and knows how to sell, it’s probably a good company. it doesn’t matter if it’s ketchup or an app, or a biotech company — it’s about the business, not the product.
Third, you have to know how to negotiate an investment. If you think that you know everything about angel investing because you’ve watched Shark Tank, you are an idiot. You have to put your own valuation on a company (which means you have to analyze it), and then negotiate how much equity you get.
Fourth, once your investment is made, if you think you just sit around and wait until the company gets sold, again, you should be doing something else. As an investor, you are a partner. That means you need to communicate with management on a monthly basis at least, and you need to do what you can to open doors, find distributors, provide management expertise, or whatever.
It’s not about picking winners, it’s about making winners. I’ve operated an angel investment group for 9 years, and most of our angel investors have made money. Tons of it. Biotech companies may take longer, but you are looking at 30X returns. However, we routinely see investors getting 5X to 10X on their money within five years. You just have to know how to do it, and get access to good deal flow.
I made a small family investment in a start up and later made an even smaller contribution in another funding round. Have tied up $7000 for nearly eleven years. The tech marketing company is finally making a small profit but there are few rumblings of a buy out or any other way I’d ever get my investment back a profit. I’m glad I didn’t do more although the eventual payoff might be lucrative. I’m not an accredited investor so I certainly couldn’t afford to go higher than that.
Around that same time, I started to make some great stock investments that have averaged above a tripling of the initial value. One stock is approaching 5x value while the worst moneys is still up a few percentage points each year on average. Since the company valuation in further funding rounds went much higher, I still have hopes of a large payoff someday. But as each year goes on with seemingly little headway taking place, I realize it’s becoming more and more like a gamble than a real investment.
Good you didn’t invest too much!
The stock market has easily outperformed the vast majority of private investments since 2009.
I’m thankful I got my $70,000+ back after 10 years.
I’ve made a couple other private equity investments, but in funds instead.
I appreciate how you have had your brushes of trial and error in investing money. I even appreciate more that you share these events in your life to help others to handle investments frugally, my cousin would love to read about this. If I were to make a venture capital investment firm, I will need well-tenured individuals like you.
It looks like better to stay with an IRA account where you can actually manage your money and diversified as much as possible using the global market. Even with indexes alone following the charts going up and coming down i could make more money during the year. thank you.
I previously went through an accelerator program called Y Combinator that has invested in companies that have gone on to be very successful such as Airbnb, Dropbox, Instacart, the list goes on.
For those who are unfamiliar, an accelerator program can be described as a “boot camp” for startups and, as the name describes, it “accelerates” the trajectory of a startup’s growth by providing some initial funding (Y Combinator invested $120k in my company when I went through the program, now the investment amount has increased to $150k), as well as expertise, mentorship and other resources to help entrepreneurs be successful.
My angel investments have been made exclusively in Y Combinator companies. The quality of companies that get accepted into Y Combinator (1%-2% acceptance rate) and go through the program is much higher than the average startup, and the failure rate is much, much lower. Like the returns in VC, it is still very much a winners driven business, but instead of a 1 win and 7 losses at Sequoia, with Y Combinator companies it is more like 1 win, 6 companies that end up doing OK, and 1 loss.
Also, as a Y Combinator alumni, I get to have a first look (even before VCs) of all new companies that graduate from the accelerator program at an event called “Alumni Demo Day” (a sort of dress rehearsal before the real “Demo Day” in which the graduating class of Y Combinator entrepreneurs will pitch to a huge audience of VCs, Angels, and other investors)
The issues of zero liquidity and dilution remain – although most investments made in Y Combinator companies during or shortly after Demo Day are done on instruments that have pro rata rights built in, so as an Angel investor, if an investment I make ends up being a winner, I have the right – but not the obligation – to invest more to maintain my stake.
Would I do better if I reallocate the money I put towards Angel investments into a broadly diversified index fund? Yes, most likely, but the Angel investments are only a small part of my overall portfolio, and the index fund is never going to have the chance (albeit very small) to turn a $50,000 investment into $50 million. You never know… if lightning strikes and I get in early into a company that ends up becoming “the next Airbnb,” that one investment will more than justify the 75% of $50,000 investments that end up doing OK (e.g. not Unicorn status) or 12.5% that fail outright. Plus, there are other benefits such as being the first to learn about new / innovative businesses and interacting with smart people.
If I was an alum and had access like you, I’d invest too no doubt.
But for most people reading this post, we don’t have the same access. So it’s best not to gamble.
What’s going on with your start up? And how many years do you foresee it taking to reach a positive liquidity event? Thanks
This article actually just came across my feed as I’m considering making an angel investment in a medical tech company. At least I have some familiarity with what they’re building. It’s a unique situation where I’ve been given an opportunity to invest in a seed round alongside legitimate VC’s. There’s something comforting about that, and not an opportunity I’ll get often I’m sure.
I’ve invested in a few companies with capital I could “lose” however, I wish I had done so with smaller amounts so I could spread out the risk. I thought I’d make a couple big bets on a few, but thinking about it again, it may have been better to make 8-10 smaller bets.
Thanks for sharing your experience. No success or failure stories yet, but I’m sure I’ll have some to tell over the next 3-5 years.
It is always interesting to see what investments highly educated people don’t feel good making. Thanks for sharing this insight. The allure is so strong with these companies. The only way I got “close” to this was investing under $1000 in a friend’s company. It seemed very strong and that the market wanted it, but the friend had family and health issues that destroyed the company.
A levelheaded and insightful analysis of why angel investing is a bad idea for Average Joe (or Average Joan). There’s generally so much that ordinary folks don’t understand about the company, the industry, or both–it’s unwise (and very risky!) to invest money in startups; you only hear about the winners like Google and Facebook but not the hundreds or thousands of companies that don’t take off and end up folding.
Thanks for the detailed and supremely helpful article, Sam!
Thanks for sharing your advice, Sam! Angel investor discussions are still too rare on personal-finance sites– I’m glad to see this one make Rockstar Finance.
I joined Hawaii Angels in 2008, and I just made my 11th investment. Each was the default $25K and I’ve added my pro-rata in most follow-on rounds. My first three investments received 100% state tax credits, although that law shut down in 2010.
No exits yet. Four startups are no longer with us. Two are too close to call. One was two months ago. Three are doing well and should exit within the next five years. (They’re all negotiating offers or at least “building value”.) The 11th investment is the accelerator Blue Startups.
Angel investors do have an edge in their local community. VCs might get “all the first looks”, but angel investments are a waste of their time. Pitches under $2M should be ignored by VCs because it’s not worth their due-diligence expenses. Local startups appreciate the social proof of local angel investors, and founders actively network for their advice & support. If you’re running a smaller accelerator then your applicants are almost universally ignored by VCs… until the founders pitch at demo day.
I started angel investing in my late 40s (near the hypothetical peak of my cognition) to immunize myself against temptation in my 70s (when I’ll probably be past my cognitive peak). I’ve thoroughly deglamorized it– it’s hard work– but it’s made me better at business and investing. I’ve met dozens of incredible people (just like FinCons and Mustachian meetups) and I’ve made a number of new local friends. I very much enjoy volunteering at Blue Startups. Personally, I’d rather help founders create jobs than donate my money to charities.
I’ve stopped making new angel investments (and this time I really mean it). I plan to wind down this part of our asset allocation instead of using the (potential) exits to fund new startups. We’ll see whether I feel differently by 2020.
Just curious, what’s your data source for the VC return charts? I was also wondering if you think the same return patterns hold for angels, as I was under the impression that the average angel returns are pretty good.
I personally don’t plan on investing in any start-ups, because I don’t have the time to spend evaluating the businesses nor do I have the capital to invest in enough different businesses to limit my risk. However, it’s an interesting topic and perhaps sometime down the road I’ll give it further consideration.
Great article. I’m sending it to my friends who do this type of investing.
To your points I’d add one more–“follow on investments.” Often there’s pressure to add money in subsequent rounds to prevent failure and/or dilution. So you up your bets in the losers and tilt the odds even more against.
I’m not sure how angel investing ever became glamorous but to me there’s nothing sexy about losing money.
It’s a good lifestyle move (but probably not investment) for people who’ve had major cash outs, and who want to employ some of their money and expertise to mentor others.
For everyone else, it’s a likely loser, and one that can dog you for decades, as in your opening example.
Another problem with angel investing is that the start up company often comes back to you to ask for more money beyond the initial investment or face dilution assuming the company can even raise more money. Not attractive options.
Sam- on your gin investment, from the numbers you’ve shared with us, there is a lot of unaccounted for money as you said. What kind of covenants could there be that the shareholders didn’t know about?
At least you got your initial investment back vs a total write off which often happens in angel investing.
Yeah, I’ve been concerned about that ever since Sam wrote about it a year or so ago, but some of the crowdfunding portals provide anti-dilution protection contracts so you can argue that is in fact better than direct angel investing where it’s caveat emptor.
I don’t think we’re at that point yet were follow-ons have happened for the CF and A+, so it will be interesting to see how that plays out. Most A+’s that have commented that they plan to do only one raise from the general public, then go straight to VC thereafter (presumably for the rest of the Series until the acquisition or IPO exit). VC’s do not typically invest during early or seed rounds due to their gorilla-sized liquidity issues. BTW, the failure rate between early and middle rounds is essentially same but the magnitude of the payoff is orders higher with early. So there’s really not much point in doing middle unless you’re a VC (or a D fund).
Great article on VC investing. This blog is like business school, but for free.
I would say that some of those conclusions also apply to stocks from bigger companies. In the end, we don’t know what they are doing with our money. Others have an edge that individual investors don’t.
That’s why I prefer ETF or even a mutual fund.
I was in a angel group in the Midwest for a number of years starting 13 years ago. Only participated in one deal, it turned into nothing. Saw lots of interesting projects – probably 50 pitches. Decided I could blow $10-$30k on my own projects just as easily and stopped participating. Since then they have had two deals do ok out of 12 I think. Great place to learn not a great place to invest in my case.
FS Founder VC and friends
$60,000 ?
? ? percentage of whole company owned
.6% 20% wild guess
at a $10 million valuation. If I understand, the founder’s value at this $10 million valuation stage is 60,000 x 33.3 = $2 million. Am I understanding the selling a company process?
$150,000 $5,000,000 $49 million
? ? ? percentage of whole company owned
0.3% 10% almost 90%
at a $49 million valuation.
Not sure I understand the structure of your questions. Can you clarify? There’s dilution, post and pre-money valuation, expenses, and things I just can’t figure out because I’m still trying to figure it out before I ask them where all the money went.
I’m trying to understand whether we can indeed figure out where all the money was budgeted in a single page. But this assumption could be entirely wrong, and we might need ten pages to truly see how the numbers actually change. Sorta along the lines of trying to summarize a many paged contract into a single page doesn’t end well ever.
I was trying to ask..
at a $10 million valuation. Your $60,000 was worth what percentage of this company? The founder had the equivalent dollars worth of how much, and what was his percentage of the company?
at a $49 million valuation. Your $150,000 is now worth what percentage of the company? The founder has $5,000,000 to $7,000,000 company worth, and what percentage of the company did he own now?
I don’t have enough money for Angel Investing but this post reminds me of my previous job. I joined a start-up with a big paycut and worked very hard (60-80 hours) hoping that I would get lump-sum when the company grows and a big player comes in and buy out. There were 20 people when I first joined but it grew very fast. I didn’t get any raise but continued working very hard but failed. Everyone blamed the 2007-08 Financial Crisis but who knows what? After realizing that there is nothing that I can control no matter how hard I work, that was it for me. I decided to change my career and became Pharmacist.
Been there as I also learned the hard way.
My only question would be – did you get anything out of it outside of cash? Like 10 years of sample tastings and product? Sometimes it is those payments and experiences which make it worth it.
While I would be reluctant to do it again as I walked away with about a 10% return (expected 4X due to purchase price but now consider myself lucky to have gotten the 10%), I do have a full set of the product lineup (manual gardening tools like rakes, hoes, shovels, etc).
Indeed. Some free product. Lots of parties. An amazing trip to Mallorca with the founder and friends.. priceless fun!
Thanks for the first hand comments – I’ve only been asked about more local startups (or a friend’s startup). And who want’s to invest in a chain of internet pizza by the slice stores that don’t deliver?
The other lesson learned probably for everybody is you try to do enough due diligence before you invest (i.e., go long) in a company’s stock, and hope it will increase in value over time. However, hope is NOT a viable strategy, and one has to have a contingency plan for every of his/her investment in case the investment does not go his/her way. There is no way you can even run a risk mitigation plan if your investment in the start-up goes South. Angel investing is analogous to buying lottery tickets. Everybody know the probability of winning a lottery is very low and that of angel investing pretty low as well. I understand the logic of not investing money in a start-up that you can’t afford to lose. But then why even bother wasting your money and time in a start-up if there are better investments with better risk-adjusted returns unless you don’t mind losing your money. Yeah, there is a potential of making 10 to 100 times your money but the probability is too low and the risk is too high.
I agree that the illusion of control is just the law of averages (where a small sample is assumed to be the same as a very large sample.)
However, your math is bad. The win probability and expected payoff of a lottery is so bottom of the barrel abysmal, angel investing looks relatively great in comparison. As does most anything else. Even cash. However, there’s a proper method for playing the lottery just as there is a proper method to succesfully angel investing. If you don’t know what it is, stay out. Math always wins in the end.
I just quoted the lottery as a somewhat exaggerated example as an illustration of the risk-reward is disappointing. I have a PhD in electrical engineering from the University of California and hence of course I know my maths. I have a proven method of making money and I am already a multi-millionaire because of my market proven and tested skills and methodology. There is zero reason for me to waste my time and money on any investments in start-ups! Buying their stocks despite all your due diligence and hope the stocks would go up just doesn’t make any financial sense.
I might be wrong on this. If any of you who have made anywhere between $10million to $100 million in your angel investments over the last 10 years, please share your stories as there is apparently something for me to learn.
Sam,
You live and learn. I have known for years the probability of win rate of all the VCs is in the range of 1 out of 8 to 1 out of 10. The risk to reward ratio just doesn’t make any financial sense. If their average annual return is in the low single digit percentage even with an army of analysts working for them after 2000, I wonder why people are still giving moneys to those VC firms.
I have been running an option based long-short hedge fund myself for the last 5.5 years. It is a self-funded hedge fund with lower risk than just buying and holding S&P 500. My average annual return over the last 5.5 years is 26%, better than that of 97% of all the professional mutual fund or hedge fund managers. I don’t live in the Bay area and hence I do have the real estate investment vehicles like those in SF bay area that appreciated at a crazy steep rate.
VC’s are the hedge funds of Silicon Valley. Lots of B.S., mystique, catchet and hyperbole, but little in the way of real world results for the vast majority. It’s just the nature of life; only a small elite, driven few can outperform a composite average consistently and they will naturally attract and hire all the top talent, so any competitors are just a bunch of me too inferiors. It’s just that in the hedge fund/VC case the average happens to be near 0% or negative compared to the public equity market, although the latter is now priced to be near 0% in the future as well. This is what always happens when too much money chases an asset class.
VC’s have huge overheads in maintaining their operations and talent, so that narrows their potential investment universe by 99% because they absolutely need unicorns to be able to survive as a financially-viable entity. They cannot accept lower return payoffs — they don’t even waste their time. If you have too much money that investing minimum amounts over hundreds of companies over a decade won’t be worth the payout, find another asset class.
Do you know what hedge fund really means? Hedge often means you would have a short position against a long position as a means to mitigate tail risks. Please do enlighten me as to how a VC could hedge his/her investments in start-ups.
@Sam: I agree the data on VC was comprehensive; I disagree that it was “comprehensive” for reflecting angel investing. VC is not even remotely the same as angel investing and you are conflating the two. VC is to Blue Chips as angel investing is to Small Caps. They have completely different different return streams.
@multimillionaire: Of course I know what “hedge fund” means — do you know what it represents in reality? Hint: It’s not all long-short.
@multimillionaire: Well, yes, I do think you need another sandbox to play in. You’re too rich and you’re gonna have the same thorny issues as the VC’s do. Not every $100 invested is going to tun into $1.25 million as it did with that rascally Uber outlier. No, it’s all downhill from there.
I view angel investing as a early around subset of venture investing. There are plenty of venture capital companies that do not invest in “blue chip” companies. Just look at crunchbase or all the companies any number of venture capital firms have made. By definition, most are not blue chip, highly coveted companies because most fail.
What are some angel investment deals you have made and how have they turned out?
I view the crowd D as a different segment than CF or A+… mostly due to the timing (crowd D is well seasoned by this point, to say the least). So I haven’t been too interested until the latter came on the scene last year, so I guess you will just have to wait the 5-10 years to find out how I’ve done. I expect that we’ll get about three years out of CF and A+ before it all goes to pot like D has, so that’s when I’ll pull the plug. The way I see it, there’s a limited window of opportunity here and I don’t want any regrets.
Some of the type of funds you’ve mentioned have reported nice IRR’s even if there’s been no exits yet. Angel investing in the traditional non-crowd D’s also has nice yearly returns going back decades. Like I’ve said several times already, if you’ve got too much money that you have to play like a VC in this space, it’s just not worth it because there’s just not enough quality opportunities to make a significant difference to your wealth. So I think you’d be better off leveraging quality real estate which can handle larger sums easily.
Machineghost,
I am not sure you have answered my question how VCs could hedge their investments in their funded companies. For people who don’t know much about it, we just use a simple term like long-short to simplify the discussion. It is not just simply to go long or to go short. To go one layer deeper, one could run option positions with negative correlation to hedge their long or short positions to have either net positive or net negative delta for all positions, or neutral delta, depending on market conditions.
I don’t have to change sandbox. I never want to play in Angel investor sandbox to begin with. I never have wanted and will never want to be an Angel investor or let VC invest my money. The risk reward ratio is not good enough to be worth my time and my money. If I can run my own funds with hedging positions with average annual return equal to 26% for the last 5.5 years. I fail to see why I would at all try angel investing that carries much higher risk and much lower return. Like I said before and I say it again, it just doesn’t make financial sense to me.
I didn’t because I felt it wasn’t germane to the conversation. I said “VC’s are the hedge funds of Silicon Valley” or something to that effect. Use the expansive definition of “hedge fund” and not the method you personally use in your own hedge fund, since that seems to be what you would like to do to deal with the high failure rate. That would be nifty, I admit. Maybe that will be possible some day with an startup index and derivatives on it.
If you look at the CAGR for angel investing, you’ll probably realize that you’re making a bad conclusion here. But then again, not everyone can handle the risk. If you’ve got a higher probability method for making roughly the same or higher return, the answer about which door to open should be obvious. In my case, I prefer to diversify.
MachineGhost,
Let me address the high failure rate you stated in your statement. The methods and mathematical models I and others use have very high probabilities of profits, usually in the range of 85% to 90%, and we have contingency plans to mitigate the risks for the remaining 10 to 15% in case the investments go against us. We don’t leave anything to chances and hence resulting in successful investing and trading years after years. The key of investing is to first not to lose your principal. We have methods in derivatives to turn losing trades to either breakeven or winning trades, and hence we have a formula for success. Like what I have said earlier, I don’t buy or go long on stocks and hope they will go up as hope is not a viable money making strategy.
I have looked at all the trades I have done in 2017 and only 5% of those trades that require my mitigation strategy and the portfolio is already up more than 13% year to date, which is more than twice than that of DJIA or S&P 500. When it comes to investing, it is all about how much Alpha one could deliver, and I am confident that I have been doing a reasonably good job for my own.
I have been approached by many about investing their startups over the years. As you can see, there is zero reason for me or the folks who are very fluent in derivatives trading to even touch Angel investing as there is no reliable method for us to manage or mitigate the risks. We are not risk averse as long as we can manage and mitigate the risks. Even though one might have done all the due diligence necessary before investing in a start-up, giving someone with or without proven track records money and hope for the best is sheer nonsense.
Sam, No pun intended just sharing my 2 cents about my successful methods.
“VCs are the hedge funds of Silicon Valley” is a very true statement. The most amazing thing is when a VC who has never built a company is advising companies on how to build a company.
I truly believe being a VC is one of the best jobs in the world.
No doubt! I invested in a startup that was trying to disrupt how heavy equipment was rented on construction sites.
As a buyer for my company we were using the app which was like an Expedia/Price Line finding the best rate.
They were going for 2nd round of financing. I even took calls speaking to the venture capitalist (David Sach’s, Social Capital,etc) wanted to know from the customer experience what I thought.
I asked the CFO if I could invest an he said YES! 4 million from the VC and 1 mill from friends/family.
I invested the minimum 10k. Within a few weeks major changes started happening. They fired my company contact who was a Chief of sales a great marketer an go-getter to go strictly web based. I stopped receiving quarterly updates.
Aside from a t-shirt an a cheap bottle of whiskey all my money was lost.
Will never do that again. Wish I would have read your post earlier.
Phew! At least it was only $10K!
Want to run my money? I’ll take just a 20% annual return net of fees any day.
But then again, it has been a bull market for the last 5.5 years, and I’ve had some similar returns in some of my funds.
Sam,
Nobody knew it was a bull market until you see it in a rear view mirror. If we had known that it would be a bull market for the last 6 or 7 years with occasional corrections, we would have used super bull strategy, and the return would have been very spectacular. We only trade and invest with what the market gives us based on our technical and fundamental analysis. What I and others running similar strategy will have some short delta positions from time to time to hedge against any downturns, depending on the projected market directions. The hedge does indeed some what costs us in terms of total annual return and hence the annual return is only 26% which is still better than most professional managers.
Sam, what are your thoughts on investing in an “index fund” of startups like AngelList’s Access Fund ( ) to diversify risk?
Their minimum investment is $100k and it’s invested into 150-200 startups.
Don’t do it unless you can afford to do it each and every year (or every new fund) consistently until you hit the jackpot. You have to smooth out the lumpy sequence of returns risk.
Let’s say you invested $100K in the fund now and then we went into a recession within six months; the failure rate of the holdings will skyrocket and certainly not be anywhere near what a long-term composite average result would be. You need to be able to do time weighted dollar cost averaging.
Or lets say you invested $100K all into P2P consumer loans within one quarter. That will expose you to tremendous economic risk compared to investing the $100K over 36 or 72 months to smooth the risk out.
The concept is a good idea, bringing indexing to VC investing.
But still issues with:
– High fees
– Lack of liquidity (which is not just about being able to put money in and out, it’s about constant accurate pricing of assets, many unlisted asset funds have been caught out when you try to ‘cash in’ your ‘paper gains’, you’re actual returns will probably end up heaps less when the fund struggles to sell assets)
– Lack of transparency
Bigger issue is that the AngelList Access Fund has underperformed the NASDAQ index in every period.
VC investing is still for suckers.
If you go indexed/low cost route, you don’t get the fantastic outlier results and underperform many cheap ETFs. Why not just get a tech ETF, micro/small cap ETF, a factor ETF or a levered ETF to get the same return exposure with much less risk/cost, higher transparency and liquidity? Countless studies showing a simple 2x levered small cap ETF blows out any VC fund with a fraction of the cost/risk. Leverage is not a bad thing considering VC funds are levered up much more and you don’t know about it.
Otherwise, you pick the VC funds or be a VC yourself to try and get the outlier results. But then why not just do stock picking and trading? You’re odds are better.
Sam, I haven’t read through all the comments yet, so I apologize if this has already been covered.
Honestly, I was surprised at the tone of your post. Usually you’re looking at the positive side of things rather than the negative. Beyond that, you’re fantastic about doing your due diligence before taking a stance on an investment class. Your angel investing record contains one mediocre outcome and two dodged bullets… not exactly a huge sample size.
I’d be curious to know what kind of progress Bulldog had made at the time of your investment. Also curious what the pre-money valuation was during the time of your investment. $10MM-post seems rich unless they had some serious traction back in 2007 (but without knowing the pre-money valuation it’s impossible to tell). Valuations were far more reasonable then than they are today. What I’m getting at here is perhaps you invested at a sub-optimal price. I wonder what things would have looked like for you at a $3MM valuation or even $1MM valuation. You might be singing a different tune!
Comparing VC returns to angel returns isn’t really apples to apples. But I completely agree that the individual, part-time angel is at a severe disadvantage to the professional.
Have you considered checking out platforms like AngelList to do angel investing? You generally pay a 20% carry (like any LP would), but you’re investing alongside a professional VC or angel. I started making very small bets last year (about $2k each) in a planned, multi-year evaluation process of the investment class.
You can also invest in their funds for a more hands off approach. Their 2013 fund has a current IRR of 46%:
https://blog.angel.co/returns/
Still early, but that’s a heck of a start!
I’ve made 13 investments in the last 12 months. None of them have exited yet, but that’s expected (still very early in the cycle), but I did actually get a notification today for a company I invested in last year that’s now raising an equity round at a $6MM valuation. I initially came in at a $3MM cap with a 20% discount, so my money is going in at a $2.4MM valuation. I can now put a bit more in for my pro-rata rights and I’ll likely do so.
All the deals I’ve participated in have been below $10MM pre-money except one (did it at $12MM), and most have been at or below $5MM. I obviously don’t have data on how well this asset class will perform, but I plan to keep making at least 1.5 investments per quarter to hopefully build a decent sample size.
I think the failure rate will be a lot lower considering I’m not sourcing the deals myself, they have proven traction, and I’m investing alongside professional angels and VCs. But hey, we’ll see!
I’ve probably dodged 30 bullets like Neo. I just didn’t write them all out. Another one was OpenTreatment, a tennis acquaintance’s startup. He hounded me like crazy, wanted $50K, sold me hard. But I resisted. That was also 2 years ago. STILL in private beta.
Do you notice something from the comments? Usually people brag about their successful investments. Not ONE person has said they’ve had a successful angel investment yet. It’s still early, but I don’t think many will. And if they do, they won’t say exactly what the company is.
EVERY angel investor is hopeful until the lights turn off for good. Yes, investing via Angel list and other source deals is fun. The guy from Triggit basically puts together a syndicate on Angel list, invests a tiny $1,000, but gets carry on the hundreds of thousands of dollars he gets rounds up.
Being a VC w/ other people’s money is much better than investing your own money directly.
Get back to me in 5 – 10 years and let us know how you do. I don’t know your net worth/income, but $2,000 investments should make you or anybody lose any sleep. I hope you get a 10 bagger, but that’s still just $20,000 before tax, and before dilution. Better than a poke in the eye, but is it really worth it? I don’t think so.
There’s a problem with waiting 5-10 years as opposed to looking at the relevant historical data now.
The noise to signal ratio is going to get worse and worse and worse over time as every me too flunky tries to cash in on CF or A+. So in 5-10 years 99% of startups won’t be worth investing in — at least for high returns rather than middling, so you wind up with the same problem as VC’s have now. Its also my impression that the D space is already full of way too much me-too junk. That isn’t exciting at all, especially via a fund investing in 100+ of them. Diworsification doesn’t help get you unicorns.
Of course it also doesn’t help that the IPO exit has radically decreased too due to Sarbanes-Oxley, but the secondary exchanges opening up should help with that problem.
So, if you can’t find a way to make it at least work with enough A+’s, then you gotta find another sandbox to play in and not regret it.
Thanks for the reply, Sam. We just have different views on the topic is all. My startup went through the 500Startups accelerator a few years back, so I have quite a bit of first hand experience with the whole startup scene. Many of my friends’ companies have had “soft landings”, some are zombies, but some are really killing it. The average person’s network (or even the non-average like yourself) just isn’t conducive to finding decent bets in the startup land.
In terms of AngelList, you can join whatever syndicate you’d like. I tend to back folks I know and trust. That certainly wouldn’t be Mr. Triggit. And still curious on your thoughts on the 2013 AngelList fund that has a 46% IRR to date.
I’m at the point where $2k per bet isn’t a big deal to me. I’m treating this as an experiment until I see some capital come back and can get an idea for the returns. Eyes are fully open here.
I’ll definitely keep you in the loop as things develop over time.
Ah, congrats on making it into the 500 Startups accelerator! How’s your company doing now?
Regarding your friends who are really killing it, have they had liquidity events yet? I’m curious to know what your definition is of doing well in startup land. And just to clarify, I love the startup scene. How can I not, living here in SF since 2001? But it’s also b/c I’ve lived here so long that the people I meet in the industry are corroborating much of the data that shows there will only be a few winners.
I can’t argue with a 46% IRR Angelist fund. Angelist itself is an incredible platform, and Nav has provided a great service. When does that particular fund return money to shareholders?
I never questioned the idea of you loving the startup scene. Being a property owner in SF… how can you not? :-)
My friends that have had successful exits have been in the range of $60MM and $200MM. So not huge $1B+ but still significant. Of those still doing well but without exit, they’ve all raised recent Series B rounds of $30MM – $50MM. So still potential there to hit the big ‘B’.
That said, of all these folks, my buddy that exited for $60MM is the one I think has maximized happiness. He built his company over 12 years but took zero outside funding. He’s locked up for another year and a half, which is never fun for any true entrepreneur, but he’s had the least amount of stress and most fun building his company. Not to mention being set for life.
Our company is doing ok. We’ll do love 7-figures in revenue this year, we’re profitable, and growing ~100% y/y. So we’re not the rocket ship that would be attractive to further VC funds. We’ve only raised ~$600k from Angels over the last few years and don’t plan to raise any more. I’d be very pleased selling for $50-$100MM in the next 3-5 years rather than trying to aggressively scale and sell optionality by raising a large round seeing as I still own ~70% of the company.
Most people don’t realize that once you take VC money your optionality for a small (<$100MM) exit is gone. But that's a completely separate topic.
If you sell for $50M – $100M w/ 70% ownership, can you buy me a kobe beef steak dinner?! That would be huge!
What percentage of the companies did your founder friends own in the various exits?
Also, why entitle your site “Drowning American” with such a bullish financial picture for yourself and your company?
Looks like we broke the comment stream here (can’t reply to your last comment). But it’d be my pleasure to treat you to a kobe beef steak dinner, Sam. You have my word.
Ownership for my founder friends varied between 5-15% except for the $60MM exit that didn’t take outside funds. He owned substantially more (obviously). I don’t recall the exact figure, but it was more than 50%.
The blog was started (later rebooted) as I was in the earliest phases of starting my company. I’d been through a bankruptcy, a DUI, and some other stupid decisions. The title name was more appropriate then I suppose.
That said, I still feel like I’m struggling because so much of my net worth is completely illiquid, tied up in the company. And even that… it’s not guaranteed.
People envy these entrepreneurs that are seemingly overnight successes, but they have no idea how hard the road is. It’s been so, so challenging and insanely taxing on not just me but my relationship. Luckily that part has gotten much better.
Gotcha. Nice job turning things around!
And here’s another thing, even with all your described issues, you still were able to build a company to it’s probably state with good growth and a good amount of funding. This is a great example of how people who persevere can bounce back, no matter what type of setback they have!
I love those stories and if you want to share with a guest post one day, you’re welcome to do so.
Related: Can Financial Samurai Be The Next $1B Fintech Company? – This article goes through the motions of trying to grow FS into a bigger company with fundraising, product, etc.. or just keep it as a lifestyle business. I chose the ladder! I think you’ll enjoy this read if you haven’t read it, and wonder which you would choose if you could do it over again.
Cheers
I think for most of the readers here, I agree with this post. Angel investing is a high risk/high reward (hopefully) type of investment. I think there is certainly a time and a place for angel investing, depending on where you are at financially. If you are still in the beginning and growth stages of your wealth accumulation… angel investing should be avoided. You need every dollar of capital you have to invest in your own assets to ramp up growth.
However if you get to a point where you have massive amounts of excess cash coming in on a regular basis, generated from solid, safe and secure assets, angel investing could be a lucrative, speculative way to make additional fortunes.
Not only can you make extremely high returns, but you are helping other investors realize their dreams. One of my original “WHYs” on why I wanted to get rich was so that I could help more people more often. Angel investing can hit 2 birds with one stone in my view; helping other investors get their business up and running and potentially offering a good return on my investment. The game of angel investing is all about doing due diligence… also, as an angel investor it is smarter to go heavy on solid prospects rather than spread your investments thin across many business ventures (put all your eggs in one basket and watch that basket!).
Watch several episodes of shark tank. Notice that each individual shark does not invest in a business venture on each episode. I have watched several episodes in a row where Kevin O’Leary (or any of the other sharks) have not made a single investment.
This goes along the lines that less than 3% of new startups seeking an angel investor actually get funded. That’s because the angel investors only want to invest in ones they are confident will be a home run!
So as I said, once you get to a point of financial ABUNDANCE, a point where your wealth begins to multiply upon itself at an extremely fast pace, continuing to gain velocity each year without any effort on your part, then maybe angel investing could be an option for you (if you know your stuff on business of course).
One other point I want to make. If you want to know who the people are who make the BIG money investing in stocks, I can tell you it’s not the people buying stock in a company at the initial public offering (IPO). By the time a company holds an IPO the insiders (early investors, angels, VCs etc) are selling their shares for many times their original investment. Just my 2 cents…
I agree with your last point. By Series C or Series D, it becomes a pile on. But again, those angels and early series investors are experiencing their 1 out of 7-10 investments that are actually going to be a home run and make up for their losses.
Folks just believe that all these huge growth companies are out there for everyone. Even if you could identify one, it’s UNLIKELY you can ever get in b/c you need to have connections to be invited to invest.
I have very strong cash flow (invested $40,000 a month in 1Q), and I have ZERO interest in angel investing. It’s the wrong move for me and I believe it is the wrong move for 95% of investors out there.
Feel free to take some risks and let me know how it goes. Just use money you are OK losing.
I am an angel investor in the S&P 500.
Seriously, thanks for this perspective. It’s a bit hard, FOMO-wise, to not want to get in on this game. Thankfully I have not tried to hard to do so.
Yes..the SPY and QQQ…Most of those angel companies don’t last…but you really have to do GOOD research and have GOD-Like connections in order to find the best.
Hey Sam, great article! Figured I’d add my experience here as someone that has only invested in 1 private company but I did it with A HELL OF A LOT OF INFORMATION. So back in November of 2014, I had been working at a startup (the same company I’m at now) and they went to do a small fundraising round. I was a high level employee at the time and was largely responsible for a lot of the growth we had seen over the past 6 months (I had started in April of that year). Because I was inside the company, I had a level of knowledge that other people outside the company were not privy to. I myself was running the sales department so I had a very intimate pulse on the company. Additionally, I felt as if I was buying more equity in a company that I was in large part running. Anyway, I invested 30k in the round (our minimum buy in was 5k for that round). Fast forward to now when we just closed a round with a private equity firm. The company invested 2.5MM in new stock and then they bought up stock from any existing investor that wanted to sell shares. So I could have just sold my original shares from that investment for $113,515 but I elected to sell none of my shares. The PE firm now owns about 20% of the company and they may continue to offer off ramps in the future. We still believe there is a lot of growth ahead for the company but the plan is to sell the full company within 3-5 years. I didn’t sell any shares because I still have an incredible amount of inside knowledge and I still impact the business a great deal so in a lot of ways, this isn’t too far off from me owning my own company. The other thing I’ll add is that this is the 2nd company the founders of this company have started. They sold their first company to Amazon so they’re certainly more experienced than your average young pup that starts a company. All this being said, I’m in favor of investing cash where you have an actual edge.
Very interesting! As the head of sales, that certain does privy you to great financial information. May I ask how old you are and how diversified your investments are?
One of the best ways to get rich is to take concentrated bets…. you’ve essentially gone ALL-IN with your career, and your additional stock purchase in your company.
I just have fear b/c nobody thought they could lose in 2000, and they lost. And nobody thought they could lose in 2007, and they lost.
And even if you WIN, like w/ this sale to Gruppo Campari, it doesn’t feel like a win b/c the multiple return wasn’t there, even though logic said it was. There’s always these random expenses and covenants that screw shareholders it seems. There is actually a growing group in SF that is fighting for their shareholder rights b/c so many employees have gotten screwed so far!
Hey Sam, so I’m 28 and I’m highly concentrated/non diversified in my investments right now. Based on the valuation from the PE company buying in, my total shares from grants and purchases at the company are worth 504k right now. Aside from that, me and the wife (also 28) have 150k in index funds and 160k in equity in our house. So total net worth is a little over 800k right now. I totally hear what you’re saying about the risk here and I agree that it is risky. But I believe it’s a calculated risk much in the same way running your own business is. I’m a high ranking employee at the company (the only people above me are the founders) so I do feel that I get to influence and have a say in policy here. I also think that because I’m higher up on the food chain, I’m less likely to get screwed. All that being said, there’s certainly tremendous risk. But I’m a risk taker and my aim is to amass a healthy nut over the next few years so I think this is my best path to do that. As far as covenants go, you’re right those can potentially be problematic. We do have a few covenants that could trigger that would be less than ideal for shareholders. However, as long as we don’t seriously get off course here, those covenants won’t trigger at all.
Cool. Good luck! When I was 28, I was taking mad risk in everything! Mostly things worked out, but sometimes I blew myself up so badly. Just don’t count your chickens before they hatch. Pretend that $504,000 is nothing.
Related: Growth Stocks > Dividend Stocks For Younger Investors
I think this piece applies to the vast majority of your readership Sam. Take heed, folks!
I am a part time angel using a small % of my total net worth but a pretty substantial raw sum. I also do equity-only advising where I trade advice, intros and other stuff for equity that vests like an employee (monthly for 2-3 year terms). I have amassed a decent size portfolio.
I stay focused mostly on the sector that I work in and have a reputation, network and knowhow.
I work hard marketing myself, networking with other investors, doing due diligence etc. to try to get into the best early stage deals. Like anything else, it takes time and work. Unlike anything else, so much of it is out of your hands.
I think maybe one of my current deals will end up being a huge hit which will make the whole experience worthwhile and maybe help me raise a fund. Or just add to the portfolio for a nice passive income bump.
Keep up the great work as always Sam.
Howdy Eric,
Always good to hear from you. Hope the new year is treating you well?
I like the strategy of advising for equity, especially if you like the company and want to be a part of the growth. Feels like you’re getting a 2:1.
Keep me posted on whether any of your private companies hit!
Sam
Been angel investing for over 10 years and you make some great points. A couple additional comments –
1. If you are going to do it, invest with someone you have directly worked with during your career. No amount of diligence can get you up to speed on a stranger who seems bright but you don’t know him. Basically a “invest in what (who) you know” adage.
2. Another huge frustration – I’ve had a few of my companies bought out by larger private companies with stock. So now I’m in some companies I know nothing about and my investment hold just lengthened by another 5-10 years. So awesome.
Cool. Any nice returns you can share? I’m looking for some nice windfalls to prove my anti-angel investing thesis wrong.
I am a entrepreneur, in 11 years into my project, I’ll pay 11 to one for any one that buys what I need to get in production every year with no problem i have 5 investiors that total 53 thousand all people I grew up with . I4065604444 I need less than 50 grand to b in production kno any one that can help me out my name is walt I dont need cash I need materials please help if Iyou can call me ill fill you in on the details
Congrats on the windfall! 5.1% is better than than nothing, which it seems like you thought you were going to get. I’d treat myself to a nice steak dinner, do the landscaping and invest the rest!
Thanks for sharing this complete story!
The fact that it is a friend’s company makes it hard. I have a number of friends who do the friends and family round, with the chance of participating with as low as $10k. I haven’t done it because a $10k gamble is a lot for me right now. As you said, you’d have to make 10-20 of them like Sequoia to cover the losses with 1 big win.
The easy part of the decision for me is I know my friends don’t NEED my money. There is so much other money out there for startups, if they can’t get it, I don’t want to get involved!
Love this post Sam!!
I too did some Angel Investing awhile ago. I invested in 2 companies directly (10k seed, 25k, series B) directly and 1 fund (500 startups) 10k. This was over 4 years ago. So far the results are hit and miss. The 2 companies I directly invested in are executing on their plan but likely at least another 5 years out until a liquidity event or bankruptcy. The 500 Startups investment I got my first distribution in December of $200, so at least it won’t be a complete loss, lol. I liked 500 Startups because the risk was spread across multiple companies. That being said the 500 Startup Fund update was less then encouraging and the iRR has turned negative. 500 startups had been valuing there companies too aggressively and changed to being based off of previous rounds. (Not sure why it wasn’t like that to begin with). Frankly, I expected a better run fund from 500 startups and so far they are all hype, poor execution.
Tim Ferris is a must read and eye opener too on Angel investing!! Having 45k deployed, I too am done until I see a positive result, which I am not expecting.
Troy
Fascinating insight about 500 Startups fund revaluing down their book so the IRR is negative. 2015 was a ridiculous time for capital raising and valuations in the startup industry. A lot of these valuations today are now 30% – 50% lower.
Keep us posted about the 500 Startups fund! Maybe you can even share a guest post? I love this stuff. Figure out WHO is the one getting richer? There always is at someone else’s expense.
Good luck w/ the $45K in invested capital!
Laziness to the rescue! The sheer amount of work I’d need to do to be an angel investor has always put me off this path. Based on the numbers you have here, maybe that is a good thing.
I’m invested in 9 startups here regionally. Not sure what the return will be – if any. You really need to go into it with the mindset that you will likely lose all your money. I did it mainly because I love small business and startups. With a nice exit on my own business I wanted to help support some local entrepreneurs. That said, I consider myself fully deployed… I’m not investing in any more until/unless I see some returns within the next few years.
What was the total amount invested in the start ups and how long ago did you invest in them? How many of the nine do you think will actually provide a return? Investing in nine start ups is pretty good based on the advice of the Sequoia capital partner provided me. Hope one hits!
I’m of the diversification mindset, so I did smaller checks in a larger number of companies. My investment checks ranged from $5k to $25k.
According to my K-1s, 2 are doing really good, 4 are treading water, and 3 are struggling.
I think Proterra is going to be my best bet.
Sam,
Despite the admonition in your post’s title, you’ve done a nice job of articulating both a responsible and prudent approach to angel investing as well as the consequences of doing it incautiously.
First though, you are lumping “Angel Investor” in with “VC”, and they’re not quite the same thing (you included a graph from Paul Graham, who articulated the distinction nicely: “Only a fraction of VCs even have positive returns. The rest exist to satisfy demand among fund managers for venture capital as an asset class.”) VCs do indeed spend a lot of time researching and reviewing companies, but (a) they’re doing their investing with other people’s money, and (b.) they are looking for a particular pattern and profile that only a teeny tiny fraction of startups will fit into. If you try and compete with Sequoia to find the next Facebook of *course* you’ll be at a disadvantage (though the bloom is certainly coming off the rose for firms looking for the next Facebook too.
You pointed out that someone interested in angel investing should limit it to a small portion of their investable capital, and shouldn’t plan to get their money back (at least not from any specific investment), and that’s excellent advice, to which I’d add that unless you’re relying on luck, you also need to spread that investable amount across multiple companies over time. I know that there weren’t as many options to do this when you made your “ginvestment”, but perhaps if you’d put that $60,000 into 12 different companies in $5,000 increments over a period of several years, you’d see a different outcome.
It also sounds like you invested in a business you (and the founder!) didn’t fully understand. Yet one of the great things about the emerging ecosystem of Reg CF funding sites in particular is that investors have access to really diverse range of industries and geographies, improving the chances that they’ll be able to find something within an industry they already understand, and quite possibly in a space that traditional VCs (or Silicon Valley angels) aren’t looking at.
For me, it’s less about the money, and more about the control: instead of a few wealthy angels deciding what “deserves” to get funded, anyone gets to help pick. And just like the way many angels have long done it, the point isn’t to make a great return (since most angel investments do not return anything), the point is that with crowdfunded investing you get to help pick who gets the funding.
Hi Andrew, thanks for sharing your thoughts. I’m having a hard time finding deals that allow me to invest just $5000. The lowest I’ve seen is usually $25,000. Many of the deals are $50,000 and $100,000.
Can you share with us what type of early-stage private deals you have made for $5000 and what has been the results (not crowdfunding)? I love to get real examples from the community. What have you learned along the way?
One of the post you wrote was regarding the Safari acquisition by O’Reilly. Can you talk about whether that deal made you and employees well off? I continue to see weird outcomes that don’t really reward the people build the company of your acquisition. It seems like venture-capital us are getting asymmetric returns.Thanks
Hi Sam,
I’ve done individual company deals via FundersClub, Wefunder, and AngelList, as well as a late-stage fund with MicroVentures. All have been $5,000 or less, and all of them Reg D investments (so arguably not true “crowdfunding”, but personally I put Reg D platforms like that — along with many of the Reg D real estate platforms like RealtyShares — into the same “crowdfunding” bucket). I also put $5,000 into a number of venture funds via Hedgeable’s “alternatives” feature (open only to accredited investors, but IMO a great value for getting very broad venture/angel diversification for a really low amount).
My first investment was with FundersClub back in 2013, and I’ve done about 1-2/year since then, and none have had any liquidity events yet (which is as expected). When I first start with a new kind of investment, I limit it to an amount I would be OK with losing entirely (not that I’d be *happy* about it, but willing to chalk it up to a learning experience), and it’s fair to say that neither of my first two investments (BoostedBoards and Goldbely) were done with a well-articulated thesis, and were done within industries I didn’t really understand that well. I’ve learned from that and since become a lot more deliberate about picking either (a) companies that are operating in an industry I personally understand so can evaluate, (b) investments in syndicates led by someone I know and trust, or (c) funds that let me diversify with a low dollar amount.
Right now I’m digging deep into Reg CF and Reg A+ opportunities, as I think they’re really important in opening up new forms of financing to a lot of categories of small and mid-size businesses that won’t ever show up on the radar of traditional angel/VCs. I intend to keep posting my results for those (and the Reg D ones if/when they have liquidity events) on my site (I know you like Real Estate, and I do too, and have written a bit about my experience with those as well yieldtalk.com/baby-steps-getting-started-with-crowdfunded-real-estate/ )
As for your question about Safari and O’Reilly, that one’s a bit different, as O’Reilly was already a 50% owner in Safari (which itself was a Joint Venture between Pearson Education and O’Reilly). In that case it was just one JV partner buying out the other (quite common — I think I remember reading that the average life of a JV is 7 years, and the buyout happened after ~13 years).
OK, so you are investing via crowdfunding platforms. Not quite the same as cutting a check directly to the company you’re investing in, but that’s fine. I’m really talking about investing directly in private companies where you have to do the due diligence from the ground up, instead of via crowd funding platform, which I’m a fan of.
I’d love to know more about the JV acquisition if you can dilvuge. Was there any sort of nice windfall for you and the employees? There’s always this media hype that talks about a company getting acquired and the founders and employees getting rich. But I consistently see this not to be the case. As an investor in this Gin company, I’m thinking the founder and CEO has $5-$7M pretax now, but maybe not since my windfall was so much smaller than I had expected as well.
So it would be insightful to share whether you were able to get a nice windfall as the CEO of the acquired co. You did mention that he decided to be a stay at home dad. So surely there was something decent? Unless your partner is doing well.
Thx!
Well, in fairness with Reg CF you are essentially writing a check to the company, as SPVs are not allowed. Maybe it’s just a semantics issue, but I don’t see investing in, say, an AngelList syndicate through an SPV as meaningfully different from a direct investment in terms of the due diligence required. I guess you could make the case that I’m giving up more direct access and control by not being personally listed on the cap table, but at these dollar amounts I’m willing to make that sacrifice.
An investment platform does help simplify the process (by aggregating company financials and other information in one place, and giving me an easy way to get at tax docs, etc,), but I wouldn’t rely on the platform for assessing the company. And using AngelList, FundersClub, and others has been a great chance to review hundreds of different companies and their pitches, which is really useful due diligence practice.
I was the CEO of the company, but I was a hired manager (the company was a 50/50 JV LLC), so not quite the same as being a founder CEO. (Indeed, one of the challenges with running a company like that is competing for talent against companies that are able to offer stock options, even though in many cases the likelihood of meaningful payout on those options for a regular startup employee are quite low; we were more successful in going after folks looking for more stability and a better work-life balance than the startup world).
There are Angel Investment groups and networks out there which allow smaller check sizes (5k) and allow you to spread risk in 10-15 companies. Most cities have one. If you’re accredited, ask around. Transactional attorneys know them well.
I invested about $10,000 in my friend’s start up and got about $800 back. It’s just not for me. You’re right about having no edge. That’s the biggest factor. Live and learn.
Sam, you’ve laid out some excellent points here. I think the most important one to consider is no one values your money like you do. That’s why it’s so important to expand your knowledge when it comes to investing and not rely on an advisor whose priorities are not in line with yours.
The potential to have your investment diluted is also a big risk when it comes to VC. And as you’ve pointed out, the big dogs will get preferential treatment over you.
Fascinating experience you had. I bet those employees were elated to get severance packages. However, not as much fun to pay for them, though?
I think angel investing is hard and you better have a whole lot of capital to risk in order to get the rewards. Like you said, 1 in 7 isn’t exactly a high percentage of big wins.
Except for a few individual stocks we already own (tobacco and PG), I don’t even invest in individual stocks anymore. it’s too easy to invest in stock index funds and very thoughtless and effortless as well. Heck, I still beat most actively managed mutual funds doing this ,and the returns, compounded, are quite high.
Love seeing posts like this sharing a first hand experience with a “lesson learned” aspect to it.
My parents who worked hard all their life and still does, always ask my opinion on whether they should look for high return (and risky) investments so they can bolster their retirement savings for the last 10 years or so before the get to the typical retirement age. They romanticize being the “uncle” in the friends and family stage of investing in a start up, luckily I have been able to talk them out of it … so far.
With all the points you had made about why you and me should not be an angle investor, hopefully I will have more convincing arguments to explain to them why investing in a start up isnt they way to go for the average investors, and even less suitable for someone who should be protecting their nest egg in the later stages of their career.
Thanks for writing this post. Several times over the years I’ve contemplated something like this with small portions of my cash. I’ve always held myself back. I think I somewhat suspected what you have in this post. It’s good to see the data to backup the decision.
That’s pretty rough- I’m feeling pretty bad about my investing in start-ups now.
Please tell me you have another post in the works that looks at the argument from the other side…
The data tells a pretty ugly story! And as an investor I should have been all over the data.
-Mike
Hi Mike, unfortunately, the numbers don’t look good. I hope your private investment as well that you leave a comment or write a guest post about your experience when it hits big!
I wouldn’t have minded and the best thing in the gin company again. But my wrist parameters were completely off. I invested too much money based on my income and net worth at the time, and I didn’t invest in multiple different companies to spread out the risk.
I could have afforded to lose the $60,000, but it would have felt pretty bad at the time. Now, my net worth is multiple times higher, but I would feel terrible terrible terrible if I lost $60,000 today.
Sometimes, ignorance can help you get lucky. But over the long run, it tends to hurt.
“Sometimes, ignorance can help you to get lucky. But over the long run, it tends to hurt.”
That’s a great quote, there, Sam. The start up I invested in 3 years ago is still around and growing EBITDA at a good clip. But all the growth is going back into more R&D of the team and the revenue is concentrated in one customer while the second product line is under evaluation. So it’s still a very risky proposition.
The other start up looks to be more promising as a food and nutritional product with good sales traction. I probably invested too much in the first company but I learned a lot in the process. A lesson that may prove to be very expensive but only time will tell. If there is a successful exit I’ll be happy to write a guest post.
What you’ve said is very important b/c Triggit, one of the companies I would have invested at least $50K, if not $100K had customer concentration risk: Facebook. And they changed the rules on their ad exchange, and Triggit basically lost the majority of its revenue over night. Can you imagine having a 10 bagger that goes to ZERO b/c of one customer decision? Need to diversify the clientele, which is exactly why I’m always hustling for new partnerships with FS that I believe in.
The second thing you said was my screw up too. $60,000 was a ridiculous amount for me at 29 yo. $25K would have been more appropriate. But I was stupid, and greedy, and didn’t understand risk well when things were going so well.
Keep me posted! I hope you have a nice windfall!!
He’s not using comprehensive data, so don’t sweat it. Just over-diversify so you can handle the losers which will be a super majority percentage. It’s not about how often you win; its about making more than you lose. You only need one unicorn and you’re set. You don’t know what or when that will be, so take the long-game.
Worrying about whale or VC challenges is like worrying about Wall Street portfolio managers. 95% are all below average or suck — they’re all me too, not trailblazers — but you’re still funding their six figure lifestyle that isn’t based on above average performance. You wouldn’t invest in me too startups, so don’t invest like a me-too VC. If you’re too rich of a whale for payoffs to make a material difference to your wealth (without acting like a me-too VC), I strongly suggest finding another sandbox to play in.
I’m pretty sure the charts in the section about returns is pretty comprehensive data analyzing 1,000+ VCs.
If you have any more comprehensive data, let me know. If we think we can outperform VCs as non VCS, where the majority of VCs underpeform, I’m not sure what to think.
This type of thinking generally happens in a bull market. What are some of your angel investing wins?
Related: Are You Delusional? Let’s Talk Dunning Krueger
Thanks for sharing your personal experiences with angel investing Sam! I’d read some pieces by Tim Ferris and Tucker Max warning about the dangerous of early-round investing. But your stories really help hammer home the point. In particular, the lack of liquidity would be a good concern for me (especially considering the low average returns). For now I’ll plan to stick to the public markets where I have a little more competence!
Tucker Max? The author of “I Hope They Serve Beer In Hell”? He wrote a book about this topic!? Yet he couldn’t make the movie version of “I Hope They Serve Beet In Hell” not suck!?
Maybe one shouldn’t judge an author by his book (or by the garbage movie adaptation).
Sincerely,
ARB–Angry Retail Banker
I think it is safe to say that unless you are prepared to spend a lot, and I mean a lot, of time doing research and conducting due diligence, angel investing is an opportunity best left on the table. I like that you provided the numbers to back up the fact that, even among the professionals, most people don’t really make enough to justify the costs. You’re pretty self-confident if you believe that you’re the special one who is going to hit the jackpot with early stage investing, when almost everyone else, regardless of the resources at their hands, don’t.
A few years back I was lucky enough to participate in a class at a US University lead by a couple of VC investors, and my takeaway back then was more or less the same back then. There’s a reason why the three F’s, the most common early stage investors, are referred to as F’s (Friends, Family and Fools) ;-)
I feel like with Shark Tank today everyone wants to be an angel investor. Shark Tank hardly shows the risk since they hardly want to make the Sharks look bad on TV. So they highlight only the successful companies afterwards, which in turn makes it seem like it’s pretty easy.
Your post also reminds me of some of the dumb money floating out there. Like the $400 juicer that is being mocked around the internet :)
don’t mock my Juicero! It’s magical and saving lives of people everywhere! ;)
Startup World (and Silicon Valley in particular) holds big virtual parades for the mega-winners and then dump the bodies of the losers off the back of Tony Soprano’s boat at sea in the middle of the night. There are a lot of bodies down there.
There are some contact clauses, that I’m sure you know. Like anti-dillusion of share ration. If you come first/early, startup owners might just take it.
Yet it’s true, you have to aim, have a solid know-how and hit big. Otherwise it’s just bottom feeding..
Anti-dilution and no liquidation preference are important clauses that protect minority investors. I insist on both in all my angel deals. Where you can still get screwed is that a future VC investor may value existing small angel investor at a discount to the next round valuation, which if a startup CEO is desperate to raise funds, will accept. Your best option is to stay put and not accept if you believe in the company as it is better to get liquidated at 30% off a 5X future round than a 2X present round.
Good post Sam on a topic that doesn’t get a lot of attention in the PF community. I intend to write an article soon on my own experience as a direct angel investor and as a small shareholder in a boutique VC fund.
The thing is, you can have all those conditions for your round, but subsequent new rounds may have different conditions based on the demand of new investors.
yes– to echo this, mgmt will always go with the money, so future investors with deeper pockets will always out-negotiate the little guy.
even if you held a trump card (right to veto a deal), what’s your alternative? let the co go under if it doesn’t get $$? then you lose. continue to fund it yourself or with other smaller angels? the well runs dry eventually and you’re in a worse position then. i’ve seen it play out a thousand times over as both a VC and Founder, bottom line is the angels get crushed when deep pockets move in and the co can’t meet its lofty expectations.
Can you talk about your VC experience? What were your returns like as a VC and how about as a founder? Thanks!
This will be fun. Shortly we’ll have someone do an elongated post on why Angel Investing works.
Essentially angel investing cannot be compared to just one investment a person made. Sure your return in this case of 6% compound wasn’t great. Are all angel investments like this? No.
Angel investments should be compared to 100s and there are a handful that work resulting in outsized returns!
When the article drops we’ll be sure to circle back!