If you wish to spend money on enterprise capital, I imagine it is extra useful to spend money on a enterprise capital fund than in particular person non-public firms. By investing in a enterprise capital fund, you’ll not solely lower your probabilities of shedding cash but in addition enhance your probabilities of incomes a constructive 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, while you lose, you’re prone to lose all of your cash invested within the non-public firm.
Over time, my conviction in avoiding investments in particular person non-public firms has elevated. The principle cause is my expertise as a restricted associate in a number of closed-end enterprise capital funds.
I’ve seen the outcomes of which firms succeed and which fail. The chances should not in favor of the person non-public firm investor. As a personal firm investor, you will need to diversify. And the simplest approach to diversify is thru a enterprise fund.
Lengthy Odds Of Hitting A Enterprise Funding Winner
As a restricted associate, I just lately considered 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 want to be fully hands-off as soon as I commit and submit capital. Not having to consider how my cash is being invested is without doubt one of the explanation why I spend money on non-public funds and am keen to pay their charges.
The enterprise capital fund invests principally in seed rounds and a few Collection A rounds. These funding rounds usually happen inside 1-3 years of an organization’s inception, which implies larger danger. Nonetheless, if the businesses succeed, the returns could possibly be huge. The founders all have spectacular resumes, and the issues the businesses purpose to unravel appear promising.
Simply know that earlier than investing in something, the advertising materials all the time makes an funding sound promising. However after all, not all investments work out, which is why diversification is vital.
Enterprise Capitalists Know the Odds of Profitable Are Low
Through the replace, I used to be proven a slide, which I can not share right here as a consequence of 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 will 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 supply 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 profitable non-public firm is way lower than the ten% chance for skilled enterprise capitalists. Moreover, the prospect of you shedding all of your cash in a person firm is way larger than the 40% chance for skilled enterprise capitalists investing in duds.
Skilled VCs Compete Aggressively For Entry
Most particular person non-public firm buyers lack an edge, experience, and a sturdy community in comparison with the skilled enterprise capitalists who run funds. Subsequently, the non-public firms a person investor will get to spend money on are possible these handed over by all different skilled VCs. This is named hostile choice, the place particular person buyers solely see the businesses that no one else desires.
Skilled VCs, then again, have a lot larger entry to one of the best non-public firm investments. Even the professionals typically must combat tooth and nail simply to get an allocation into one of the best firms. This entry to prime non-public firms is what restricted companions pay for.
Taking a step additional, people typically compete to realize entry to prime enterprise capital funds!
Instance of a Failed Enterprise Capital Funding That I Thought Would Succeed
Take, for instance, an organization known 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.
Through the pandemic, Cameo’s reputation soared as individuals had been caught at dwelling. As a substitute of assembly pals for a party or going out to dinner for a marriage anniversary, individuals discovered methods to present digital presents. It was an amazing thought!
I obtained various enjoyable cameos from tennis gamers I adopted, gifted by a good friend. A publication reader even reached out to see if I would be keen to report a one-minute message as a present for his good friend’s marriage ceremony. I did, and I received paid a number of hundred bucks.
The enterprise mannequin was easy: get attention-grabbing individuals to enroll in the platform and create video and audio recordings. These people would receives a commission a market charge, 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 varied funding rounds for Cameo, the dates, and its buyers.

I invested in a prime enterprise capital fund that raised $600 million in 2018. In 2019, it began deploying capital, and one in every of its investments was in Cameo. The fund invested 4% of its capital, or $24 million, in Cameo throughout its Collection B spherical. The post-money valuation was roughly $250 million.
Two years later, in 2021, Cameo raised a $100 million Collection C spherical at a post-money valuation of $1 billion! Hooray! My enterprise capital fund had made a minimum of a triple on its funding in two years, even after dilution.
Then, on March 13, 2024, Cameo raised a $25.1 million spherical, additionally known as a Collection 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 Collection C spherical at a $1 billion post-money valuation, I in all probability would have stated sure to the tune of $25,000.
We had been nonetheless in COVID on the time, I did a Cameo myself on the platform, and felt {that a} $1 billion market cap was nothing this present day. Moreover, I knew good and linked VCs who had totally 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 fireplace, and buyers simply could not lose. Ultimately, buyers misplaced large because the 2022 bear market hit, bringing everyone again all the way 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 Collection C funding is taken into account a “crackdown” funding spherical. For brand new buyers, a $100 million post-money valuation for Cameo appears engaging.
Nonetheless, 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 earn a living. 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 50 investments. Out of the 50 investments, 7, or 14%, are grand slams value 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 every of them. In complete, the $600 million fund that started deploying capital in 2019 is now value about $2 billion on the finish of 2023. That is a couple of 5-year compound annual development charge of 27%. Not unhealthy!
The principle winner of the fund is its $25 million funding in Rippling, an HR enterprise software program firm, which was value $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 value 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 along 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 Personal Firm Investing
Most of us should not skilled buyers or investing lovers. Regardless of getting my MBA and dealing in equities for 13 years at GS and CS, there’s solely a lot time I wish to spend investing in shares.
With two younger youngsters and different pursuits, I shouldn’t have the bandwidth to do due diligence on particular person non-public firms. Furthermore, if there’s a sizzling non-public firm I wish to spend money on, I will not be capable to get entry until I make investments with a longtime enterprise capital agency.
Subsequently, I’ll gladly pay a payment and a proportion of income to personal fund managers spending 40+ hours per week attempting to spend money on firms I’ve no entry to. As you become older, it feels higher to farm out cash administration duties to release 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 when it was valued at $500 million, a design firm. But, Figma grew right into a $10 billion valuation simply three years later. The issue with solely investing in what you perceive is that you would be able to miss out on so many different alternatives.
Letting My Personal Investments Journey
My preliminary capital dedication of $140,000 on this fund in 2018 is now value about $406,000 as of 4Q 2023. It might have been value $462,000 if all $140,000 of the capital had been known as. However, solely $123,900 has been known as in any case these years. It often takes 3-5 years for 100% of your dedicated capital to be known as.
I am joyful to have met the capital calls over time and locked up the cash in these non-public 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 over time. All I needed to do was carry on assembly capital calls, thereby dollar-cost averaging by way of good and unhealthy years.
If you wish to spend money on particular person non-public firms, please do not. Solely achieve this in case you are keen to construct a portfolio of a minimum of 20 firms with related funding sizes. Bear in mind, skilled enterprise capitalists construct portfolios of fifty or extra firms, anticipating solely 10% of them to offer outsized returns. I believe that chance drops to five% or much less as a person investor.
With as much as 20% of my investable capital, I would a lot slightly spend money on enterprise capital and different non-public funds yearly. It feels significantly better understanding that skilled non-public buyers are targeted on making worthwhile investments so I haven’t got to.
Reader Questions
Do you could have any non-public firm funding winners? What’s your observe report been like with investing in particular person non-public firms? If you happen to spend money on enterprise capital funds, how have they performed?
If you happen to’re inquisitive about investing in non-public development firms, take a look at the Innovation Fund. It’s an open-ended enterprise capital fund with a minimal funding of solely $10. Not like closed-end enterprise capital funds, you may see what the Innovation Fund is investing in after which determine how a lot to speculate. You even have liquidity when you want it.
My private purpose is to speculate $500,000 in non-public synthetic intelligence firms throughout the yr. I am doing so partially by way of the Innovation Fund as a result of I need publicity to AI firms similar to OpenAI, Anthropic, and Databricks. The AI revolution is right here, and I wish to be part of it. Fundrise can be a sponsor of Monetary Samurai.