The Ledger
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Akkina: MITIMCo Passed on an Early Opportunity to Invest in OpenAI
“I mentioned we're investors in YC, and when Sam left YC, around then we also had an opportunity to invest in OpenAI, and we didn't do it. So that's definitely an error of omission that I think about a lot.”
Akkina: MITIMCo will scale out of VC funds that become too large
“If a firm gets too big and we're no longer confident that we can make exceptional returns over time, we're going to have to scale out.”
Akkina: MITIMCo writes $1M checks to emerging managers without track records
“And then the, a third bucket we have now is things where basically we'll write a million dollar check because maybe it's extremely early and the person had no track record, not even an angel track record, let's say, or we're doing it to work with them to sourc…”
Akkina: MITIMCo commits $50M–$150M across 6–8 core U.S. venture funds
“So today, at least in the U.S. Venture portfolio, we probably have Maybe six to eight core relationships we would refer to them as where we're writing checks of like 50 to a hundred fifty million per fund.”
Akkina: MIT Endowment Remains Liquidity-Constrained Until Major Unicorns Like Stripe Exit
“We're less liquidity constrained now than we were say at the beginning of last year, but the major issue still continues to be that there's all these big companies like Stripe, for instance from the last cycle that have not had liquidity events yet. And so unt…”
MITIMCo approved a Rippling co-investment within hours on a Friday night
“Within a few hours, Friday night we made the decision to back that deal.”
Akkina: Direct co-investments offer higher conviction than blind-pool fund commitments
“I personally find it easier in a lot of cases to write a big check to a co-invest than to a blind pool fund, right? Because no matter your conviction in someone, when you're writing them a blank check, you know, we don't know what's gonna happen, right? And as…”
Akkina: MITIMCo almost never sells fund stakes on secondary markets
“We'll certainly think about it. We almost never do it because we're not willing to do it at a low price, right? I mean, the reason these secondary funds exist is obviously to get high IRRs themselves, right? And so, generally speaking you know, if we're sellin…”
MITIMCo Biases Toward New Fund Managers With Angel Track Records
“Although, I would say when we back a new fund, we do probably have a bias towards people who at least have some kind of angel track record.”
MITIMCo invested $120M in Coupang, returning 7-8x at distribution
“So in, you know, in the case of Coupang, that was a hundred twenty million co-investment for us. We made, I think, a distribution price is seven to eight X or something like that.”
Akkina: MITIMCo supports strategy shifts if communicated early and purposefully
“I mean, we want people to do what they say, but if they discover the original strategy is not likely to work, then obviously we want them to evolve, right? So I think it's about, You know, communicating that early if you are gonna shift your strategy and doing…”
MITIMCo Declined Co-Investments From Respected GPs at Peak Tech Bubble
“I would give ourselves some credit for, at the peak of the bubble, we said no to several co-investments where, ah, you know, people that we really respect and still respect were pounding the table to do these things, and we said no.”
Akkina: Venture fund evaluation requires assessing see, pick, win, and service
“It's see, pick, win, right? We need people who can see the best deals or at least a very large volume of deals, right? Hopefully the best deals are inside that set. Then we want them to be able to pick the best ones to try and invest in. And then finally they …”
MITIMCo evaluates GPs primarily on winning deals and servicing portfolio companies
“I would say we tend to spend the most time thinking about the winning and servicing angle, which kind of feed on each other. Because I think, you know, look, there's at least several hundred people in the industry at any given time, GPs I'm talking about, who …”
Few University Endowments Can Execute Large Direct Investments Quickly
“We're probably one of the few LPs, certainly one of the few university endowments who can react to one of these things very quickly in, in big size.”
Akkina: VC fund success cannot be judged in first three years
“Honestly, I would say in the first three years, you usually can't tell. Right. It would be some time between three and five years where we start to see whether they're, some of their companies really inflected. And we don't necessarily care whether something h…”
Akkina: MITIMCo's default strategy is loyalty to existing fund managers
“Our default is always to be loyal to the people who we're already invested in, right?”
Akkina: Green Oaks is one of MITIMCo's top fund relationships over 10 years
“And I remember actually, you know, my boss, Seth, and I decided, you know, let's, let's leave this and look at fund two or something. And the next, but I slept on it, and then the next day I decided to call my boss, Seth, back and say, you know, I think we sho…”
Akkina: Peak valuation of failed oil investment exceeded $1 billion at 5-7x
“I mean, this thing was worth, I think over, you know, well over a billion dollars at peak. And at peak it was probably like a five to seven X for us.”
MITIMCo backs Sequoia, Andreessen Horowitz, Green Oaks, Y Combinator, and Initialized Capital
“So we're lucky to be in a lot of the big names you would expect, you know, Sequoia, Kleiner Perkins, Andreessen, et cetera. And then, you know, there's some newer things as well that we've done in the past 10 or 15 years, like say, Green Oaks or Y Combinator i…”
Akkina: MITIMCo recovered roughly one-third of capital on worst direct deal
“I think on that particular deal, we still recovered about a third of our capital or something like that, so it wasn't a zero”
Akkina: MITIMCo structured most of its Coupang investment as senior notes
“Most of the money we invested in that was in this special structured note where we felt it had very protected downside, but managed to keep a lot of the upside as well.”
MITIMCo was constrained to a small Snowflake pre-IPO allocation
“I mean, there's another opportunity where we co-invested in Snowflake before it IPO'd, and in that case, we were only able to get a few million bucks allocation, even though, given what we knew about the company, we would have invested a lot more if we had the…”
Akkina: MITIMCo writes $10M–$20M checks for mid-tier venture funds
“And then after that, we have another bucket where the check sizes are typically 10 to twenty million per fund.”
Akkina: MITIMCo deliberately minimizes time demands on portfolio fund managers
“And of course, something we try to do as LPs is not be overly demanding in, The time we take from people, right? You know, we're always very conscientious of the fact that we want most of these people to be spending most of their time out on the field, right? …”