With much love for my angel investors, angel investing is absolutely a mug's game.
If the company doesn't get off the ground (vast majority of investments) you lose all your money.
If the company does get off the ground, you are the lowest on the pref stack, and you have no ability to follow on to protect your position.
You're not a contributing employee or meaningful future source of capital so your piece of the pie is just dead weight on the cap table. This means every single subsequent investor (and the founders, if they care more about money than their relationship with you) has an incentive to cram you down.
So net net the chances of success from passive angel investing are only slightly better than playing the lottery.
Best approach would be to make very few investments, where you're able to build a special relationship with the founder, and ideally get a board seat to defend your stake.
===
Edit - to be clear, I don't think startups should be giving board seats to angel investors. It does happen in exceptional cases where the angel is uniquely valuable to the company, and those are the cases where the angel can defend themselves. But they are rare, which is why it's mainly a bad game to play.
>Best approach would be to make very few investments
Top VCs—who see the best deals and run deep diligence—still only have a 1–5% hit rate. As an angel, you don’t have that level of access or time. Even if you get strong referrals, you’d need to be 10–15x better than elite VCs to pick winners in a small portfolio. Unless you’re investing in at least 10 companies, it’s statistically a losing game.
My experience: I invested in ~200 companies early stage (with some winners like HuggingFace, Checkr & more).
I've not seen that much but what I've seen is "Let's ask a few buddies and google a bit".
The takeaway that I agree with is the parent's and OP's point that you will need to invest in a lot of companies, perhaps 30-50, and you will nee to be in for the long term.
A lot of angel investors are not investing particularly large sums, and a lot of what they're doing is buying someone that's going to use services other people they're connected to are selling.
When you're multiples are 10,000x revenue, a lot of people will shell out $10k to get you onto a few startup services...
That's the investment itself. Not getting paid back.
As an angel you do have a few advantages over VCs. There is no pressure to invest a certain amount within a certain time frame, so you can wait as long as you like until something comes along you really like. You can also do very small tickets, whereas a VC cannot afford to waste time on small stuff.
But I agree making money should not be the focus. I like to think of it as a "giving back to society" hobby. I enjoy supporting entrepreneurs, society needs more of them. I enjoy talking with the other investors, most of them other entrepreneurs like me. By contrast, other people my age buy a boat or a Porsche, angel investing makes me feel more useful.
For reference: I've only made 6 investments as an angel over the last decade, mostly SaaS, one exited at 12x, one died, four are still going at various levels of success but all healthy. So making money is possible, even if it's not the goal.
I'm not sure I'm following how anyone can target the angel investors specifically? Aren't all common share holders have the same fate? So if they screw the common share holders, early employees will get the same treatment as the angels? (dilution for example impacts all share holders). I understand that key employees can receive extra shares along the way, but most probably don't in their first 4 years.
The way I've heard it is that later investors collude (descriptive, academic term, not value judgment) with founders via liquidation preferences, dilution, etc., and effectively wipe out all common shareholders (particularly employees) and all earlier rounds, and then give the founders some additional terms to compensate them specifically. How exactly that works, what they're giving the founders, and how this isn't hugely illegal are all details that I don't understand. I put a top-level comment asking exactly that.
Yea the founders also have majority common stock. So there's not a normal scenario where the founders and other investors get paid out in an exit, but the angels don't.
The bigger fear is a non-exit scenario, where the company becomes profitable, possibly pays out large investors to maintain the relationship, and founders just take massive salaries. So no liquidation event that benefits angel investors.
This, and I'd add that one underrated upside of angel investing (and being LP of funds) is access to real, unfiltered information about the startup and the market. That's often far more insightful than the "everyone is crushing it" narrative you see in the media. In the article, the author mentions that she found other ways to get that info.
Is it a thing for angels to exit in the early rounds?
Instead of being shoved down the cap table by a giant tranche of series A preferred stock, might it not be appropriate to give the angel a payday instead?
I guess some angels want to keep their fingers in the pie? And, more likely, it’s just not a reasonable expectation to see an exit like that way before anyone else does?
It’s just the same thing as a take profit in the stock market. Intellectually it seems reasonable but because a lot of the bets go straight down (never raise another round for that take profit opportunity) you need a higher multiple of the ones that win.
You end up taking profit at a 1.1 return and in 10 years it ends up being uber.
Positive skew strategies (lose a little on a lot of bets and win big on a few) are impossible to use take profits on because you need those big winners.
early exits probably won't get the type of return that an angel investor would be interested in monetarily, since you need more than fu-money to motivate them.
Same author talks about Angel investors getting screwed by later rounds.
Here’s an example of a portfolio company that not only converted angel investor ownership to common stock, but also drastically decreased the number of shares.
I started asking for pro-rata side letters in 2017. But I recently found out (the hard way) that it’s common for follow-on investors to completely disregard any pro-rata rights of angel investors.
Founders, like entry-level workers, are closer to an option than a stock. There's a good chance that the payoff will be negative (in the sense that sometimes a company going to zero is a significant time-consuming process to investors). Someone who continuously buys out-of-the-money options will bleed money over time,
A general rule of thumb is that you have 3 board members at the seed (1 non-CEO founder, the CEO which is typically another founder, and the lead investor). So you have 1 seat available for investors, whereas you may take 5-20 checks. Not everyone is getting a seat.
At the A you usually expand to 5, adding the lead of the A round and an independent board member. Beyond that, it’s common for the earlier investors to get replaced on the board in future rounds and maintain observer rights.
> So net net the chances of success from passive angel investing are only slightly better than playing the lottery.
Is this right? An organization running a lottery—their whole job is to run a lottery, they’ve staked their reputation on the fact that they pay out to winners. The one with a reputation to defend is the one paying out.
The company angel investor is dealing with a company that, ultimately, wants to either get into position to sell some service, or wants to get bought. Their raison d'etre isn’t being a reliable payer-out of winners. I’d expect the lottery to be much more honest.
Take a couple years to learn how the industry works, make connections, maybe even get lucky with some bets. Then use all that to either start your own fund or get a job at a big Silicon Valley VC firm.
Hell, investing in general is a "mug"'s game (never heard this phrase before) if you go by per-capita return. It's the exceptionsl performers that make an outsized contribution to revenue that floats the whole boat.
I've heard variations on this sentiment repeated a lot. The exact message varies, but it's usually some variation of: early investors always lose, small investors always lose, and/or non-preferred shareholders always lose. I've seen and lived a small number of personal anecdotes that seem to back this up, and I'd like to better understand what underlying pathology causes this.
I understand that early investors are taking the most risk, and clearly there's a lot of downside. But what prevents them from being able to realize or capture the upside?
I've heard a theory, a few different times now, that bigger, later investors effectively collude (descriptive term, not value judgment) with founders to squeeze out early founders and employees (common shareholders) via unfair terms, such as excessive dilution (accepting too low a valuation for larger investment), excessive liquidation preferences (2x or more), etc., and then topping the founders up via side deals. I've heard that, by virtue of squeezing out passive participants, they're able to offer more to the founders, and that incentivizes the founders to take their deal over other alternatives. Does anyone know more specifics about how this happens? In particular, how is this not a breach of fiduciary duty to passive participants?
It's definitely possible to write anti-dilution clauses, etc. But, I've heard that more or less no one writes them, and more importantly no one accepts them. If this is a pretty well-known game, why haven't countermeasures become popular?
For my personal anecdote, I was once an early engineer - the first hire after their Series A - at a small startup that never found product-market fit. The economy was bad, and they were running out of money, and they took - as I understood it - a dubious Series B led by a dubious investor. The founders were very vague about the terms of the round. In particular, the founders revealed that the investors took liquidation preference, that it was greater than 1x, but absolutely refused to say how much. That always left a bad taste in my mouth. When I left, I didn't exercise my options. In the end, the company floundered, and is a zombie to this day. In that regard, I suppose that the particulars of that round don't really matter - none of us were seeing anything regardless.
I'd really appreciate if anyone closer to the money part of this industry could weigh in.
> later investors effectively collude with founders
> a small startup that never found product-market fit. The economy was bad, and they were running out of money, and they took - as I understood it - a dubious Series B led by a dubious investor
The unfortunate reality is that if a startup cannot survive for long on its own, the economy is bad, and investment interest is low - then past invested effort from founders and employees and money from early investors is a sunk cost. They have together created something with almost no independent economic value.
The later investors can buy the assets created so far at near zero cost (the alternative is a bankruptcy auction). They can reasonably argue that the future value of the business is all from their investment, together with a deal to hire the founders and current employees to invest future effort into it.
I mean, yes, that's exactly the argument that the bigger, later investors make, and their lawyers are happy to back them up on that for money.
But consider this. If that were truly the case, why would the later investors work so hard to maneuver their way into this allegedly worthless startup? Why not hire an entirely separate team to build an entirely separate app, and they can own the whole thing with no fuss? If they value the founding team, why not tempt them away to a new venture, and shed all the baggage? Economics has an idea called "revealed preferences" - that words can be deceiving, but costly behaviors are honest - and this does look to be the revealed preferences of the investors.
In other words, just because the later investors can use the threat of insolvency to get their way doesn't mean what's already there doesn't have value.
It's people who lose, which is most, complaining about structural issues when actually they just suck at investing. It's a competitive game, they lost.
I mean, multiple things can be true at once, no? They could have made bad choices or had bad luck. Simultaneously, the system could be rigged for and against certain categories of participants. From what I've heard, there's a lot of both of these going around; startups are highly volatile, but also a lot of the people in the space not only don't play fair, but actively deride playing fair.
>Angel investors also face the longest time horizon for liquidity of any investor. Private equity aims for 3-5 year returns, and VCs typically run 7-10 year fund cycles, but angels usually wait 10+ years for exits. This means angels aren’t just taking company-specific risk, but also the risk of facing more macroeconomic cycles.
>Think about all that's happened since 2009 when I started: multiple presidential administrations, a global pandemic, zero interest rates, and now high inflation and higher interest rates. My investments have had to withstand all of these shifts, and many didn't make it through.
Really interesting stuff (for me, as an outsider).
Can anyone comment if VCs are looking for shorter fund cycles or are the macro economic shifts what's capping it at 10 years?
I once read one reason why startups take so long to IPO is so private investments can benefit longer from the growth
My LPs want liquidity now, always. 2021 was hot and it’s been relatively quiet since. Mega funds are keeping companies private longer. Capital is tied up which hurts emerging managers trying to raise. My LPs want returns in 6 years which only works if everything goes perfectly which almost never happens; that’s how long $100M+ rev takes if you triple yearly. IPO requires more rev than before, everything’s larger.
As an LP, I would be excited for liquidity in 10 years at this point.
It seems like even for successful companies, there isn't a clear path to an exit for many of them. Add to that the increase in late-stage investors, and there isn't much of an incentive to exit.
I always assumed angel investing (at least as it emerged originally) was essentially philanthropy with the motivation being it gave very rich people a way to nudge things they liked into existence and provided them with a semi-cheap way to keep their network fresh with young, hungry, interesting new people. Bonus it might very occasionally turn in to a lottery ticket (but that wasn't the primary driver of making the investment).
This seems to be a big part of it, but is there a separate word for it? It’s definitely not philanthropy because it’s not directed at public good.
Economics must have made a term for this part of the venture ecosystem. “Seed capital” misses the significant social and class aspects of the behavior.
Historically, the term you're looking for might have been "patronage". Wealthy individuals supported artists, scientists, or explorers not purely for financial return, but because they believed in the person, the cause, valued the association, enjoyed the influence, or whatever else.
From chatgpt: “ In summary, Halle Tecco’s personal portfolio comprises about 34 direct investments, of which 24 have at least one female founder (as detailed above). This means roughly 70% of these companies were co-founded or founded by women. Notable female-founded companies in her portfolio include Everly Health (Julia Cheek), Cityblock Health (Dr. Toyin Ajayi), Kindbody (Gina Bartasi), Tia (Carolyn Witte/Felicity Yost), Hued (Kimberly Wilson), and many others listed in the first section. Halle Tecco’s investment focus has clearly encompassed a large number of startups with women on the founding team, aligning with her advocacy for female entrepreneurs in health tech ”
Call it charity or call it buying gal-pals with hubby’s money but primarily investing based on identity seems like a bad idea
If she’s rich and married a successful tech founder, I don’t understand why she didn’t get a lawyer to draft these investment papers to keep herself from getting fleeced. Like the amount she was dropping could probably have been recouped from a buyout without much fuss if the contracts were a bit more assertive.
My first thought when I opened the article: I wonder if s/he would have been better in a low cost S&P500 tracker ETF instead of angel investing. Conclusion: Yep. Google AI tells me: <<Since 2012, the S&P 500 has returned about 424.72% or 13.33% annually, assuming reinvestment of dividends.>>
I think there's just too much money chasing too few good businesses. Early days of tech boom with lots of opportunities is over. Any promising startups nowadays get crazy valuation very quickly, so stop making financial sense to invest in.
In a tale as old as time, the mega-rich get richer. It used to be that early stage VCs and angels could see tremendous upside for taking an early risk. It’s utterly unsurprising that giant VCs have found a way to cram them down once the startup is successful and realize all the upside.
Between this and giant PE coming downmarket, we should all just bootstrap and say “f off” to outside capital. With AI coding models, you don’t need that money to build anyway.
>In a tale as old as time, the mega-rich get richer
no, they don't. what is mega-rich keeps price inflating, but who is mega-rich are always new names.
if you are young, afauk Brin and Page have always been mega-rich, but just a little older and you remember when nobody knew who they were, nor had anybody heard of Zuck, or Musk, etc. and Jobs was a washed up has-been
Readit News
If the company doesn't get off the ground (vast majority of investments) you lose all your money.
If the company does get off the ground, you are the lowest on the pref stack, and you have no ability to follow on to protect your position. You're not a contributing employee or meaningful future source of capital so your piece of the pie is just dead weight on the cap table. This means every single subsequent investor (and the founders, if they care more about money than their relationship with you) has an incentive to cram you down.
So net net the chances of success from passive angel investing are only slightly better than playing the lottery.
Best approach would be to make very few investments, where you're able to build a special relationship with the founder, and ideally get a board seat to defend your stake.
===
Edit - to be clear, I don't think startups should be giving board seats to angel investors. It does happen in exceptional cases where the angel is uniquely valuable to the company, and those are the cases where the angel can defend themselves. But they are rare, which is why it's mainly a bad game to play.
Top VCs—who see the best deals and run deep diligence—still only have a 1–5% hit rate. As an angel, you don’t have that level of access or time. Even if you get strong referrals, you’d need to be 10–15x better than elite VCs to pick winners in a small portfolio. Unless you’re investing in at least 10 companies, it’s statistically a losing game.
My experience: I invested in ~200 companies early stage (with some winners like HuggingFace, Checkr & more).
I've not seen that much but what I've seen is "Let's ask a few buddies and google a bit".
The takeaway that I agree with is the parent's and OP's point that you will need to invest in a lot of companies, perhaps 30-50, and you will nee to be in for the long term.
When you're multiples are 10,000x revenue, a lot of people will shell out $10k to get you onto a few startup services...
That's the investment itself. Not getting paid back.
Deleted Comment
But I agree making money should not be the focus. I like to think of it as a "giving back to society" hobby. I enjoy supporting entrepreneurs, society needs more of them. I enjoy talking with the other investors, most of them other entrepreneurs like me. By contrast, other people my age buy a boat or a Porsche, angel investing makes me feel more useful.
For reference: I've only made 6 investments as an angel over the last decade, mostly SaaS, one exited at 12x, one died, four are still going at various levels of success but all healthy. So making money is possible, even if it's not the goal.
The bigger fear is a non-exit scenario, where the company becomes profitable, possibly pays out large investors to maintain the relationship, and founders just take massive salaries. So no liquidation event that benefits angel investors.
Instead of being shoved down the cap table by a giant tranche of series A preferred stock, might it not be appropriate to give the angel a payday instead?
I guess some angels want to keep their fingers in the pie? And, more likely, it’s just not a reasonable expectation to see an exit like that way before anyone else does?
You end up taking profit at a 1.1 return and in 10 years it ends up being uber.
Positive skew strategies (lose a little on a lot of bets and win big on a few) are impossible to use take profits on because you need those big winners.
That’s not why they do it.
Perhaps also relevant:
From: https://capitalgains.thediff.co/p/the-favor-trading-economyAt the A you usually expand to 5, adding the lead of the A round and an independent board member. Beyond that, it’s common for the earlier investors to get replaced on the board in future rounds and maintain observer rights.
A pro rata opportunity? Maybe but why wrangle 50 angels when you can have 2 firms cover it?
Is this right? An organization running a lottery—their whole job is to run a lottery, they’ve staked their reputation on the fact that they pay out to winners. The one with a reputation to defend is the one paying out.
The company angel investor is dealing with a company that, ultimately, wants to either get into position to sell some service, or wants to get bought. Their raison d'etre isn’t being a reliable payer-out of winners. I’d expect the lottery to be much more honest.
OP made an unbacked assertion and that can be ignored as such.
Take a couple years to learn how the industry works, make connections, maybe even get lucky with some bets. Then use all that to either start your own fund or get a job at a big Silicon Valley VC firm.
The best use of angel investing if anything is building a track record, for VC.
But it’s Facebook.
I understand that early investors are taking the most risk, and clearly there's a lot of downside. But what prevents them from being able to realize or capture the upside?
I've heard a theory, a few different times now, that bigger, later investors effectively collude (descriptive term, not value judgment) with founders to squeeze out early founders and employees (common shareholders) via unfair terms, such as excessive dilution (accepting too low a valuation for larger investment), excessive liquidation preferences (2x or more), etc., and then topping the founders up via side deals. I've heard that, by virtue of squeezing out passive participants, they're able to offer more to the founders, and that incentivizes the founders to take their deal over other alternatives. Does anyone know more specifics about how this happens? In particular, how is this not a breach of fiduciary duty to passive participants?
It's definitely possible to write anti-dilution clauses, etc. But, I've heard that more or less no one writes them, and more importantly no one accepts them. If this is a pretty well-known game, why haven't countermeasures become popular?
For my personal anecdote, I was once an early engineer - the first hire after their Series A - at a small startup that never found product-market fit. The economy was bad, and they were running out of money, and they took - as I understood it - a dubious Series B led by a dubious investor. The founders were very vague about the terms of the round. In particular, the founders revealed that the investors took liquidation preference, that it was greater than 1x, but absolutely refused to say how much. That always left a bad taste in my mouth. When I left, I didn't exercise my options. In the end, the company floundered, and is a zombie to this day. In that regard, I suppose that the particulars of that round don't really matter - none of us were seeing anything regardless.
I'd really appreciate if anyone closer to the money part of this industry could weigh in.
> a small startup that never found product-market fit. The economy was bad, and they were running out of money, and they took - as I understood it - a dubious Series B led by a dubious investor
The unfortunate reality is that if a startup cannot survive for long on its own, the economy is bad, and investment interest is low - then past invested effort from founders and employees and money from early investors is a sunk cost. They have together created something with almost no independent economic value.
The later investors can buy the assets created so far at near zero cost (the alternative is a bankruptcy auction). They can reasonably argue that the future value of the business is all from their investment, together with a deal to hire the founders and current employees to invest future effort into it.
But consider this. If that were truly the case, why would the later investors work so hard to maneuver their way into this allegedly worthless startup? Why not hire an entirely separate team to build an entirely separate app, and they can own the whole thing with no fuss? If they value the founding team, why not tempt them away to a new venture, and shed all the baggage? Economics has an idea called "revealed preferences" - that words can be deceiving, but costly behaviors are honest - and this does look to be the revealed preferences of the investors.
In other words, just because the later investors can use the threat of insolvency to get their way doesn't mean what's already there doesn't have value.
Deleted Comment
>Think about all that's happened since 2009 when I started: multiple presidential administrations, a global pandemic, zero interest rates, and now high inflation and higher interest rates. My investments have had to withstand all of these shifts, and many didn't make it through.
Really interesting stuff (for me, as an outsider).
Can anyone comment if VCs are looking for shorter fund cycles or are the macro economic shifts what's capping it at 10 years?
I once read one reason why startups take so long to IPO is so private investments can benefit longer from the growth
As an LP, I would be excited for liquidity in 10 years at this point.
It seems like even for successful companies, there isn't a clear path to an exit for many of them. Add to that the increase in late-stage investors, and there isn't much of an incentive to exit.
I would imagine that building these smaller companies looking for smaller exists would be easier and more predictable.
Economics must have made a term for this part of the venture ecosystem. “Seed capital” misses the significant social and class aspects of the behavior.
Call it charity or call it buying gal-pals with hubby’s money but primarily investing based on identity seems like a bad idea
If
> Tecco is married to Jeff Hammerbacher, cofounder of Cloudera
https://en.wikipedia.org/wiki/Halle_Tecco
https://substack.com/home/post/p-162623790
1. Investors choosing poorly
2. Investors not managing relationships well after they invest.
Maybe we can open up the discussion to involve the other design decisions that go into how funders structure deals and involvement.
- Other investment assets have seen higher inflation rates in the US in the last decade
- Buffet et al are holding cash, ostensibly for lack of qualified opportunities
But it would be interesting to compare with China, Europe, LatAm...
Between this and giant PE coming downmarket, we should all just bootstrap and say “f off” to outside capital. With AI coding models, you don’t need that money to build anyway.
no, they don't. what is mega-rich keeps price inflating, but who is mega-rich are always new names.
if you are young, afauk Brin and Page have always been mega-rich, but just a little older and you remember when nobody knew who they were, nor had anybody heard of Zuck, or Musk, etc. and Jobs was a washed up has-been