If you wish to spend money on enterprise capital, I imagine it is extra helpful to spend money on a enterprise capital fund than in particular person personal firms. By investing in a enterprise capital fund, you’ll not solely lower your possibilities of shedding cash but additionally improve your possibilities of incomes a optimistic return.
I have been a enterprise capital investor since 2001, and I strongly discourage angel investing. As a rule, you’ll find yourself shedding the overwhelming majority of the time. Moreover, whenever you lose, you’re prone to lose all of your cash invested within the personal firm.
Over time, my conviction in avoiding investments in particular person personal firms has solely elevated. The primary cause is my expertise as a restricted companion in a number of closed-end enterprise capital funds.
I’ve seen the outcomes of which firms succeed and which fail. The percentages usually are not in favor of the person personal firm investor. As a personal firm investor, you will need to diversify. And the simplest option to diversify is thru a enterprise fund.
Lengthy Odds Of Hitting A Enterprise Funding Winner
As a restricted companion, I not too long ago seen a quarterly replace from a small early-stage enterprise capital fund. I hadn’t attended one for over a yr as a result of I desire to be fully hands-off as soon as I commit and submit capital. Not having to consider how my cash is being invested is among the the reason why I spend money on personal funds and am prepared to pay their charges.
The enterprise capital fund invests largely in seed rounds and a few Sequence A rounds. These funding rounds sometimes happen inside 1-3 years of an organization’s inception, which implies better threat. Nevertheless, if the businesses succeed, the returns could possibly be monumental. The founders all have spectacular resumes, and the issues the businesses intention to unravel appear promising.
Simply know that earlier than investing in something, the advertising materials at all times makes an funding sound promising. However in fact, not all investments work out, which is why diversification is vital.
Enterprise Capitalists Know the Odds of Profitable Are Low
Throughout the replace, I used to be proven a slide, which I am unable to share right here resulting from privateness considerations. It depicted a bubble chart of 60 firms the fund had invested in. One small bubble represented the 6 anticipated winners, a medium-sized bubble represented 30 firms that may survive with insignificant exits, and one other bubble represented 24 firms forecasted to not succeed.
What amazed me was that, regardless of the fund managers’ willingness to spend money on 60 promising firms, they already anticipated to lose 100% of their funding in 40% of the businesses (24 out of 60), and 50% of the businesses (30 out of 60) to provide little returns or lose cash. Solely 10% of the businesses had been anticipated to be worthwhile.
As a person investor, the prospect of you investing in a successful personal firm is much lower than the ten% likelihood for skilled enterprise capitalists. Moreover, the prospect of you shedding all of your cash in a person firm is much better than the 40% likelihood for skilled enterprise capitalists investing in duds.
Skilled VCs Compete Aggressively For Entry
Most particular person personal firm traders lack an edge, experience, and a sturdy community in comparison with the skilled enterprise capitalists who run funds. Due to this fact, the personal firms a person investor will get to spend money on are possible these handed over by all different skilled VCs. This is called opposed choice, the place particular person traders solely see the businesses that no person else desires.
Skilled VCs, however, have a lot better entry to one of the best personal firm investments. Even the professionals usually must battle tooth and nail simply to get an allocation into one of the best firms. This entry to high personal firms is what restricted companions pay for.
Taking a step additional, people usually compete to realize entry to high enterprise capital funds!
Instance of a Failed Enterprise Capital Funding That I Thought Would Succeed
Take, for instance, an organization referred to as Cameo. Cameo is a web-based platform that permits customers to e-book customized video messages from celebrities, athletes, influencers, and different public figures. Based in 2017, the corporate goals to create distinctive, memorable interactions between followers and their favourite personalities.
Throughout the pandemic, Cameo’s recognition soared as folks had been caught at house. As an alternative of assembly mates for a birthday celebration or going out to dinner for a marriage anniversary, folks discovered methods to provide digital presents. It was an ideal concept!
I obtained a variety of enjoyable cameos from tennis gamers I adopted, gifted by a pal. A publication reader even reached out to see if I might be prepared to report a one-minute message as a present for his pal’s marriage ceremony. I did, and I received paid a number of hundred bucks.
The enterprise mannequin was easy: get attention-grabbing folks to enroll in the platform and create video and audio recordings. These people would receives a commission a market fee, and Cameo would acquire a proportion of the income. The enterprise appeared simply scalable—all Cameo needed to do was create {the marketplace}.
Cameo Historic Funding Rounds
Under highlights the assorted funding rounds for Cameo, the dates, and its traders.

I invested in a enterprise capital fund that raised $600 million in 2018. In 2019, it began deploying capital, and one in all its investments was in Cameo. The fund invested 4% of its capital, or $24 million, in Cameo throughout its Sequence B spherical. The post-money valuation was roughly $250 million.
Two years later, in 2021, Cameo raised a $100 million Sequence C spherical at a post-money valuation of $1 billion! Hooray! My enterprise capital fund had made not less than a triple on its funding in two years, even after dilution.
Then, on March 13, 2024, Cameo raised a $25.1 million spherical, additionally referred to as a Sequence C for some cause, at a reported valuation of solely $100 million! Supposedly, present shareholders have seen as much as a 99% decline in valuation after the brand new funding phrases.
Would Have Invested In Cameo If I Had The Alternative
If my enterprise capital fund had requested its restricted companions to co-invest with them through the Sequence C spherical at a $1 billion post-money valuation, I in all probability would have mentioned sure to the tune of $25,000.
We had been nonetheless in COVID on the time, I did a kind of Cameo myself straight, and felt {that a} $1 billion market cap was nothing at the present time. Moreover, I knew sensible and linked VCs who had completely vetted the corporate for me.
If I had invested in Cameo, I’d have misplaced all my cash. Phew.
Why Did the Enterprise Capital Funding Bitter?
Bear in mind, 2021 was a increase yr. Meme shares had been going loopy, tech shares had been on hearth, and traders simply could not lose. Ultimately, traders misplaced massive because the 2022 bear market hit, bringing all people again right down to Earth.
Cameo in all probability did not develop its valuation as a result of it raised an excessive amount of cash at too excessive a valuation, the pandemic ended, demand waned, and the corporate overhired.
Cameo’s 2024 Sequence C funding is taken into account a “cramdown” funding spherical. For brand spanking new traders, a $100 million post-money valuation for Cameo appears enticing.
Nevertheless, it stinks for me and different restricted companions who invested on this enterprise capital fund, proper? Not so quick! As I indicated above, VCs count on about 90% of their investments to not generate income. Cameo will possible be a part of that 90% on this fund.
The Profitable VC Investments Made Up For The Losses
This fund that invested in Cameo made about 50 investments. Out of the 50 investments, 7, or 14%, are grand slams price about $1.5 billion primarily based on a ~$175 million funding. Round 12 of the fund’s investments are within the inexperienced, totaling about $530 million primarily based on a $300 million funding.
It simply so occurs that Cameo is not one in all them. In complete, the $600 million fund that started deploying capital in 2019 is now price about $2 billion on the finish of 2023. That is a couple of 5-year compound annual progress fee of 27%. Not unhealthy!
The primary winner of the fund is its $25 million funding in Rippling, an HR enterprise software program firm, which was price $542 million within the fund on the finish of 2023. Given Rippling raised one other spherical of funding in 2024 at a $13.4 billion post-money valuation, I assume the fund’s stake in Rippling is price much more.
As a person investor, would I’ve invested in Rippling at a decrease valuation? Most likely not. The founder left on unhealthy phrases together with his earlier firm, Zenefits. Moreover, I did not perceive HR administration software program and its potential. However the normal companions did and knew the founder, so I used to be saved.
Particular person Traders Have No Edge in Non-public Firm Investing
Most of us usually are not skilled traders or investing fanatics. Regardless of getting my MBA and dealing in equities for 13 years at GS and CS, there’s solely a lot time I need to spend investing in shares.
With two younger youngsters and different pursuits, I should not have the bandwidth to do due diligence on particular person personal firms. Furthermore, if there’s a sizzling personal firm I need to spend money on, I will not have the ability to get entry until I make investments with a longtime enterprise capital agency.
Due to this fact, I’ll gladly pay a charge and a proportion of earnings to non-public fund managers spending 40+ hours per week attempting to spend money on firms I’ve no entry to. As you grow old, it feels higher to farm out cash administration tasks to unencumber time to do what you need.
Not solely would I’ve invested in Cameo and never invested in Rippling, I’d have additionally handed on Figma, a design firm, when it was valued at $500 million. But, Figma grew right into a $10 billion valuation simply three years later. The issue with solely investing in what you perceive is you can miss out on so many different alternatives.
Letting My Non-public Investments Trip
My preliminary capital dedication of $140,000 on this fund in 2018 is now price about $404,000 as of 4Q 2023. It will have been price $462,000 if all $140,000 of the capital had been referred to as. However, solely $123,900 has been referred to as in spite of everything these years. It often takes 3-5 years for 100% of your dedicated capital to be referred to as.
I am completely satisfied to have met the capital calls through the years and locked up the cash in these personal firms. So long as these firms are executing, they need to proceed to develop in worth. It is also been good to not must expertise visibility volatility through the years. All I needed to do was carry on assembly capital calls, thereby dollar-cost averaging by good and unhealthy years.
If you wish to spend money on particular person personal firms, please do not. Solely accomplish that if you’re prepared to construct a portfolio of not less than 20 firms with comparable funding sizes. Bear in mind, skilled enterprise capitalists construct portfolios of fifty or extra firms, anticipating solely 10% of them to offer outsized returns. That likelihood drops to five% or much less as a person investor.
With as much as 20% of my investable capital, I might a lot moderately spend money on enterprise capital and different personal funds yearly. It feels significantly better realizing that skilled traders are targeted on making worthwhile investments so I haven’t got to.
Reader Questions
Do you might have any personal firm funding winners? What’s your monitor report been like with investing in particular person personal firms? If you happen to spend money on enterprise capital funds, how have they carried out?
If you happen to’re eager about investing in personal progress firms, take a look at the Innovation Fund. It’s an open-ended enterprise capital fund with a minimal funding of solely $10. In contrast to closed-end enterprise capital funds, you possibly can see what the Innovation Fund is investing in after which determine how a lot to speculate. You even have liquidity for those who want it.
My private aim is to speculate $500,000 in personal synthetic intelligence firms throughout the yr. I am doing so partially by the Innovation Fund as a result of I would like publicity to AI firms corresponding to OpenAI, Anthropic, and Databricks. The AI revolution is right here, and I need to be part of it. Fundrise can be a sponsor of Monetary Samurai.