Plus: My interview with Oscar co-founder Mario Schlosser
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After 15 consecutive years of angel investing, I hit pause in 2024. It's now been a full 12 months without writing a check, marking the longest hiatus in my angel "career."
There isn't enough transparency in angel investing, and my past posts on the topic have been reader favorites. So I decided to share why I stepped back from angel investing after backing 54 companies and what I'm doing instead. Next week, I'll follow up with the cold, hard data on my portfolio performance.
A few years ago, people were trying to convince me to raise a fund. There was a lot of money going around for emerging fund managers, and I had enough of a track record to make a reasonable VC. I thought seriously about the opportunity and what it would mean for me personally and professionally. I talked to potential partners and colleagues. I did the math on what size fund we’d need to raise.
During this exercise, I reflected on why I began angel investing in the first place:
For fun: I really enjoyed working with founders
To learn: I wanted the unparalleled opportunity of being at the forefront of innovation and trends
For the money: I liked investing, and I wanted to put my money to work
Ultimately, I decided running a VC fund was not how I wanted to spend my time. In fact, I realized I didn’t even want to spend my time angel investing anymore. Through this exercise, it became clear to me that there were better ways to achieve those goals.
Angel investing follows basic portfolio theory principles—each individual investment carries extreme risk, so you need to build a diverse portfolio. The standard advice is that you need 20-30 investments minimum to have a statistically viable chance of finding a company that returns your entire fund.
But it’s this same diversification that spreads you too thin. My portfolio became too broad to meaningfully support. I couldn't provide the kind of value that initially drew me to angel investing: working closely with founders to help them succeed.
What started as a few hours a month quickly grew into a full-time (unpaid) job. When you back 50+ companies, even minor requests add up on a daily basis:
One company needs you to help close a key hire
Another is raising a bridge round and wants your input on the deck
A third is struggling with a co-founder conflict and needs advice
An investor calls asking you to vouch for a portfolio company they’re considering backing
All this happens while new pitches continue to flood your inbox. The result was increasingly shallow interactions with more and more companies, exactly the opposite of what drew me to angel investing in the first place.
When I started angel investing, one of my primary motivations was to learn. I convinced myself that being on cap tables would give me special insight and keep me current in the industry.
But when I really thought about it, I realized that angel investing provides surprisingly limited learning opportunities compared to other outlets. Following industry news, hosting a podcast, teaching, writing a book, starting companies, attending conferences, having coffee with founders (without the pressure to invest), and joining advisory boards were equally, if not more, effective ways to learn about the industry.
I still believe there’s something ✨ magical ✨ you soak in working alongside founders. I just don’t think investing is the only way to get that experience. In fact, I've found that advisory roles and board positions often provide deeper insights than passive investing because you're more actively involved. The reality is that most angel investors get sanitized quarterly updates (if that), which barely scratch the surface of what's really happening in a company. When you're more deeply engaged—even without a financial stake—you get to see the unfiltered challenges and strategic decisions that drive real learning.
The math simply stopped mathing – especially when weighed against my other priorities.
Unlike VCs, who are compensated for their work through management fees, angels do it for free while also taking 100% of the financial risk.
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.
The post-ZIRP era (2023-2024) created headwinds that even well-positioned startups struggled to navigate. Just since 2023, I have had:
One company that raised over $100M, with my shares at one point valued at over $1M on paper, acquired in a fire sale that returned zero to early investors
Two others that were also “acquired” with some fanfare in the media, but returned nothing to early investors
Four companies shut down after being unable to get to profitability or fundraise
Four others that raised money but with painful recapitalizations that effectively wiped out early shareholders
That last bullet was the nail in the coffin for me. For new investors to come in and wipe out early investors just because the market was in their favor was painful. It felt like opportunistic resets that enriched later investors at the expense of early supporters (not to mention early employees).
It’s also worth noting I've made more money building companies than I have investing in them. Some of that is luck, but founding a company provides something angel investing doesn't: the ability to directly influence outcomes.
When you account for the opportunity cost of capital, the extreme time horizon, the macro risks, and the possibility of having your ownership severely diluted, the potential returns need to be astronomical to justify the investment. And as my portfolio data shows (which I'll share next week), those returns simply aren’t materializing at the rate needed to offset these risks.
So what's filling the startup-shaped hole in my life now that I've stopped writing angel checks? I've pivoted to approaches that better align with my original goals:
Depth over breadth
For deeper founder relationships, I joined the board of growth-stage company Collective Health, a startup we invested in over a decade ago at Rock Health. I also helped start Cofertility, where I serve as Board Chair.
Learning out loud
For continued learning, I'm doing all the fun things like hosting a podcast and writing this newsletter/blog. I also teach two courses a year, one at Columbia Business School and one virtually at Harvard Medical School. As Phil Collins said, “In learning, you will teach, and in teaching, you will learn.”
Professional capital deployment
Lastly, I became a Limited Partner (LP) in a handful of VC funds, basically paying professionals to do the investing on our behalf. It's been three years, so it's still early, but it will be interesting to see if the VC returns are better than direct investing.
I haven't closed the door permanently on angel investing, but any return would look different from my previous approach. For now, I'm enjoying the clarity that comes from a more concentrated focus. Sometimes the best investment decision is deciding not to invest at all.
Next week, I'll share the complete data on my 54 startup investments over 15 years—including returns, losses, and current portfolio status.
Health insurance has a Net Promoter Score (NPS) of around 0-10 industry-wide, one of the lowest ratings of any industry. This is exactly why the founders of Oscar Health, with no background in healthcare and a distaste for the industry, started the company in 2012. Since then, Oscar has grown to 1.7 million members, gone public, and achieved profitability—all while receiving an NPS significantly higher than the industry average.
In this episode, I interviewed Mario Schlosser, co-founder and CTO of Oscar Health, about building a tech-first health insurance company in an industry notorious for poor customer experiences.
We cover:
🏥 Why outsiders without healthcare backgrounds decided to tackle the insurance industry
💰 How Oscar grew to 1.7 million members while maintaining a 60+ NPS score in a hard-to-please industry
📊 The balance between denying unnecessary care and empathetically supporting members
⚙️ How ICHRAs (Individual Coverage Health Reimbursement Arrangements) are disrupting traditional employer-sponsored healthcare
🧶 The beginning of the unraveling of the employer markets
💼 The changing employer healthcare market and why small businesses are seeking alternatives
Tune in wherever you listen to podcasts! Apple | Spotify
They say you’re not supposed to celebrate a fundraise. Just get back to work. But…
➡️ Women’s health companies get less than 5% of digital health funding.
➡️ Women-led companies get under 2% of venture funding.
So when a woman-led women’s health company breaks through these odds—let us do a little dance to celebrate before getting back to work.
Read the original article
Comments
By propter_hoc 2025-05-0315:0914 reply 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.
By alexeichemenda 2025-05-0317:196 reply >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).
By jll29 2025-05-0318:25 "...and run deep diligence"
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.
By throwaway2037 2025-05-0410:582 reply
Is HuggingFace public or acquired? I checked Wiki. It still looks pre-IPO/un-acquired. So, how exactly is this investment a "winner"?> with some winners like HuggingFaceBy michaelt 2025-05-0413:15 It might not have paid back the initial investment, but the company isn't bankrupt, and you've heard of it.
By the standards of people who invest in 100 start-ups at once, that's success.
You don't need to sell your stake for it to be a winner. It's a winner because his stake in the company is worth significantly more than when he bought it.
By robocat 2025-05-050:09 Plus the bragging rights: a lot of the angel and VC buzz seems to be about playing for status (versus playing for money).
You see this with celebrities investing, and with the intro "I was an early investor in ____" brag.
By onlyrealcuzzo 2025-05-042:08 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.
By kjkjadksj 2025-05-0416:29 Can’t you just deploy 1/10th the capital and get the same hit rate?
By iwontberude 2025-05-0317:441 reply Developing a network of people who do favors for each other and learning about other people’s businesses and industry. Angel investing usually isn’t that capital intensive, so it’s sometimes worth pursuing. I don’t do it to get rich.
By code_biologist 2025-05-0320:59 At my last startup, I think our board and observers liked hanging out more than they liked talking about the company. It wasn't perfect, but it's their money so I wasn't going to complain.
By speleding 2025-05-0416:31 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.
By RainyDayTmrw 2025-05-0318:031 reply 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.
By propter_hoc 2025-05-0318:132 reply That's exactly the approach. Seen many deals where the (remaining) founders get a big slice of new vesting options or reverse vesting shares as part of a recap or semi-distressed round.
Nothing illegal about it when the company needs the money, just one investor can write the terms they want, and the founders are on board with the plan.
By RainyDayTmrw 2025-05-0318:171 reply I understand that, particularly in a down round, investors can push to get more. What I don't understand is what allows founders to get a side deal. It seems like that would go against fiduciary duty to common shareholders and earlier rounds.
By propter_hoc 2025-05-0318:561 reply It's because the investors still need the founders to run the business, usually.
By RainyDayTmrw 2025-05-0319:111 reply More bluntly, why wouldn't/can't the other common shareholders sue?
Because then they'd be left with their original stake, but in a worthless, bankrupt company.
By newsclues 2025-05-0320:59 But it sounds like the ford v dodge brothers cases that most abuse as an excuse for corporate profit maximization.
A company should not work to enrich some shareholders at the expense of others
By themanmaran 2025-05-0317:12 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.
By ummonk 2025-05-044:38 Yes, being an early employee is a sucker's game in much the same way as being an angel investor.
By pea 2025-05-045:33 You can do a pay to play where anyone who can’t follow on at a certain price gets wiped out
By paulddraper 2025-05-0416:46 Founders/employees can receive additional grants.
By pfannkuchen 2025-05-0319:24 Isn’t angel investing more about networking and feeling like some elder statesman than about returns? That’s my impression anyway, as a non-angel.
By wslh 2025-05-0316:12 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?
By motoxpro 2025-05-049:19 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.
By DrAwdeOccarim 2025-05-0318:15 Yea, I’ve seen cashing out the principal+next investment and letting the rest ride.
By chii 2025-05-0317:53 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.
By paulddraper 2025-05-0416:45 No Angel investor is looking to 2-3x their money.
That’s not why they do it.
By robocat 2025-05-050:00 Same author talks about Angel investors getting screwed by later rounds.
https://www.halletecco.com/blog/angel-investing-part-iii#:~:...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.Perhaps also relevant:
From: https://capitalgains.thediff.co/p/the-favor-trading-economyFounders, 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.
By algo_trader 2025-05-0316:431 reply What happens if your "lead" angels want to put money but not a board seat?
If you are taking truly no institutional capital, it's a party round -- and unless you have a repeat founder that knows exactly what they're doing (and often even then!), it's a huge red flag.
A board seat? Absolutely not, you’re a minor investor.
A pro rata opportunity? Maybe but why wrangle 50 angels when you can have 2 firms cover it?
By BlandDuck 2025-05-0315:18 Too many investors, too few seats
By codezero 2025-05-0315:20 Very few of the startups I’ve worked for have given board seats before Series B.
> 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.
> Is this right?
OP made an unbacked assertion and that can be ignored as such.
Eh, this is a site for chit-chatting, so I don’t expect perfect proofs generally. Assertions that are backed only by personal experience and hard-to-verify anecdotes are fine IMO.
> Eh, this is a site for chit-chatting, so I don’t expect perfect proofs generally. Assertions that are backed only by personal experience and hard-to-verify anecdotes are fine IMO.
Source? Footnotes?
By bee_rider 2025-05-0417:26 Lol, right?
Getting away from the original posts, but: The reflex to ask for sources probably comes from a good place. But, it has become too immediate nowadays online, to the point where (in my opinion) it gets in the way of discussion.
The request for a source should generally include a note on how the fact being questioned will impact the overall argument. Friendly conversations shouldn’t become asymmetrical homework generating exercises.
By paxys 2025-05-0315:30 At best it’s a stepping stone to a “real” VC job.
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.
By peterlada 2025-05-0320:30 Way off. Angel investing is betting on people you know well enough.
By paulddraper 2025-05-0416:40 Correct.
The best use of angel investing if anything is building a track record, for VC.
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 read the point as being that angels can't really afford to invest broadly enough to hit those exceptional performers.
By jay_kyburz 2025-05-0322:00 >Four others that raised money but with painful recapitalizations that effectively wiped out early shareholders
I think its the recapitalizations that make the investments unfair. To buy a stake in a company then have it diluted by the bigger fish once a lot of the risk has been mitigated is BS if you ask me.
By jxjnskkzxxhx 2025-05-0415:491 reply How come Peter thiel wasnt diluted in Facebook?
By paulddraper 2025-05-0416:41 He was.
But it’s Facebook.
By RainyDayTmrw 2025-05-0317:573 reply 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.
By ProblemFactory 2025-05-045:271 reply > 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.
By RainyDayTmrw 2025-05-046:52 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.
By danielmarkbruce 2025-05-040:541 reply 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.
By RainyDayTmrw 2025-05-041:201 reply 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.
By danielmarkbruce 2025-05-044:531 reply You are hearing the voices of failed investors. There are successful angel investors. There are guys in the NBA finals getting paid $50m a year. There are movie stars.
In extremely competitive pursuits with insanely good outcomes, you are going to find an enormous number of people trying to make it and fail.
By RainyDayTmrw 2025-05-0418:431 reply I'm not sure your examples make the point you intend. Isn't Hollywood famously rigged, to the point where the term "Hollywood accounting" exists?
By danielmarkbruce 2025-05-0420:57 If hollywood was really truly rigged, how does Brad Pitt make it?
Some things are rigged - most competitive "winner takes all" or close to it are just insanely difficult. Startup investing is probably the least rigged thing in the world, it's just crazy difficult.
>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 $100M+ rev takes if you triple yearly. IPO requires more rev than before, everything’s larger.
6 years?
As an LP, I would be excited for liquidity in 10 years at this point.
It seems like even for successful companies, there isn't a clear path to an exit for many of them. Add to that the increase in late-stage investors, and there isn't much of an incentive to exit.
A bit hyperbolic but yeah. It also depends on the industry / stage. I’m always looking for creative ways to get liquidity out given the exit issues you mention.
I wasn't trying to be hyperbolic actually. I really would be happy if an exit would happen in 10 years.
Thankfully, I can be patient, but I wonder sometimes if some of these companies will ever exit.
By bix6 2025-05-0317:39 Sorry, I meant my statement was a bit hyperbolic at 6 years.
Waiting for a few as well, good luck!
Would smaller ventures not be an option? Say investing 500k$ and selling for 10M roughly 5 or 6 years later?
I would imagine that building these smaller companies looking for smaller exists would be easier and more predictable.
By bcantrill 2025-05-0317:02 It would be helpful to run out the math on the $500K investment: what's the post-money on that investment when it was made? How much capital did this mythical sold-for-$10M in 5-or-6 years company raise? (Or did it survive for a half decade on a total investment of $500K?) What was the headcount and the revenue and the burn? (And to whom does it sell for $10M?) Assuming that it wasn't a wipeout, you'll quickly find that the math doesn't... math: if you have somehow conjured a successful outcome in your mind, what you likely have is not a venture-scale business.
By bix6 2025-05-0316:55 That’s not necessarily venture returns so LPs might not be interested. Selling secondaries is also a pain as you generally have to pay fees and sell at a discount.
