Oct 20, 2021 · 36m · 20vc
20VC: Breaking News: Ankur Nagpal Raises $70M for Vibe Capital, What The Next Decade For Venture Will Look Like, Do VCs Actually Add Any Value & Pre-Emptive Rounds, When To Take Them and When To Reject Them
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of TwentyVC, host Harry Stebbings interviews Ankur Nagpal, Founding Partner at Vibe Capital, who announces the public launch of his $70 million Fund II. Nagpal shares insights on transitioning from operator to investor, portfolio strategy, market valuation traps, and emerging international venture opportunities.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 26.6% of the talking time here. How this is scored →
Harry as informed peer 5.1 Guest teaching 4.7 Guest disagreement 2.4 Harry pushing back 4.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 10:27 Despising Cap Table Collecting
Ankur strongly rejects the practice of option checks and cap table name-collecting, stating he despises transactional round construction that provides no true depth of relationship.
Hardest push from Harry ▶ 14:55 Disagreeing on Price DisciplineHarry directly pushes back against Packy McCormick's praise of Ankur's price discipline, stating openly that he disagrees and demanding Ankur justify his real stance on valuation.
Biggest teaching moment ▶ 16:00 The Pre-PMF Capital TrapAnkur articulates how multi-stage firms create dangerous signaling loops by following early hype and dumping tens of millions of dollars into startups before they have achieved product-market fit.
Harry holds his own ▶ 13:38 Pressing on Transactional VentureHarry challenges Ankur's optimistic take on founder-investor relationships by pointing out how compressed deal timelines have transactionalized the entire fundraising process.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Ankur Nagpal on Transitioning from Operator to Investor | 4 | 4 | 1 | 3 | Harry probes Ankur on transitioning from angel investing to institutional fund management, specifically asking how he balances rapid deployment expectations with fiduciary duty. Ankur explains how putting significant personal capital into his fund and charging zero management fees reframed his discipline around deploying capital. | |
| Breaking News: Public Launch of Vibe Capital Fund II | 5 | 4 | 1 | 4 | Harry asks sharp structural questions regarding portfolio construction, stage concentration, and whether mega-funds squeeze out smaller seed investors on pro-rata rights. Ankur breaks down his strategy of maintaining zero formal reserves and treating pro-rata participation as distinct SPV investments. | |
| Conviction Investing vs. Cap Table Collecting | 6 | 5 | 4 | 6 | Harry challenges Ankur on whether venture capital relationships have become purely transactional amid compressed fundraising timelines. Ankur forcefully rejects cap-table name collecting and option checks, emphasizing that he prefers deep compounding relationships built over decades. | |
| Navigating Market Pricing, PMF Traps, and Founder Secondaries | 7 | 6 | 3 | 7 | Harry directly disagrees with Packy McCormick's quote that Ankur is price disciplined, pressing him on market valuation levels and asking if Teachable was a middling outcome. Ankur acknowledges the middling outcome and educates on the trap of multi-stage funds over-capitalizing pre-PMF startups. | |
| Strategic Opportunities in Emerging International Markets | 6 | 5 | 4 | 5 | Harry presents his three-part evaluation framework for international investing and highlights the rapid valuation inflation in Pakistan. Ankur reframes Harry's framework by pointing out that local business models differ from Western ones and playfully teases Harry for sparking the market hype himself. | |
| Macro Trends in Venture Capital and Evaluating VC Value-Add | 6 | 6 | 3 | 6 | Harry asks point-blank whether VCs actually add value overall or if incumbent firms will acquire smaller operator funds. Ankur asserts that the majority of investors take away value, arguing that the primary rule for VCs should simply be to do no harm and offer emotional support. | |
| Quick-Fire Round with Ankur Nagpal | 2 | 3 | 1 | 1 | Harry runs through a quick-fire round covering books, personal weaknesses, and recent investments. Ankur rejects the idea that venture investing is hard compared to running a startup, calling investing an absolute dream. |
Statements from this episode (26)
Ankur Nagpal Invested in Roam Research, Eight Sleep, Circle, Hone Health, and Maven
“Anka has previously made investments in the likes of Rome Research, Ate Sleep, Circle, which we did together, actually, Hone Health, and Maven, to name a few”
Teachable Was Acquired by Hotmart for Reported $250M in 2020
“Anchor led the company until their reported two hundred and fifty million dollar acquisition to Hotmart in 2020.”
Nagpal: My First Two Angel Investments Are Now Worth Zero Dollars
“My first two investments, I'm not going to name them, but I'm pretty sure they're worth zero dollars today.”
Teachable Raised $13M and Sold With $10M Still in the Bank
“At Teachable, too, we raised thirteen million dollars in equity financing, which is pretty small for kind of where the company ended up. When we sold, we still had ten million in the bank.”
Nagpal Personally Funded 33% of Vibe Fund I and 25% of Fund II
“I put a large amount of capital into the fund myself. So for the first fund, it was, you know, a third of the fund for the second, probably 25% of the fund.”
Vibe Capital Charges Zero Management Fees to Invest 100% of Capital
“We also charge zero management fees. So a hundred percent of the capital we raised ended up being invested.”
Ankur Nagpal Launches Vibe Capital Fund II With At Least $70M
“We're now excited to launch fund two, which will be, you know, an At least seventy million dollars, maybe a little bit more.”
Nagpal Admits Vibe Capital Fund I Was Overly Diversified With 80 Companies
“So, you know, we ended up with almost 80 companies in fund one, which was very clear that it was too many and it was a little bit too diversified.”
Vibe Capital Fund II Targets 40 Core Positions Up to $4M
“So for fund two, our goal is to concentrate a little bit more. I think we'll end up with roughly Four D-ish core positions, and by core positions, I would define them, you know, average of one and a half million dollars per position, but there'll be a range, I…”
Vibe Capital Does Not Set Aside Formal Fund Reserves for Follow-Ons
“So we never kept formal reserves just because I want to have the flexibility downstream to adapt to new information, right?”
Teachable Maintained a Two-Person Board for Its Entire Existence
“We had a two-person board for the entirety of Teachable, which is, which I highly recommend.”
Accomplice's Jeff Fagnan Is Vibe Capital's Largest LP
“He went from that to the starting Spearhead, giving me an angel fund, to now developing into our largest LP, where we're co-investing in deals together”
Founders Should Optimize for Median-Case Outcomes, While VCs Optimize for Best-Case
“I think founders should optimize for the median case outcome, like a case where the company could do relatively well and you can still end up wealthy versus the very, very best case outcome while investors should always optimize the very, very best case outcom…”
Nagpal Considers Teachable's $250M Acquisition by Hotmart a Middling Outcome
“I think the teachable outcome was a middling outcome. I mean, I'm obviously very proud of, you know, what the team accomplished and all of that, and big fans of the company Hotmart that we ended up being acquired by. But yeah, I would classify as very much as …”
Founders Should Accept Preemptive Series A Rounds but Reject Series B
“I think a preemptive A, you do it. A preemptive B, you don't. Because I think at an A, you already have a roughly infinite amount of money. Like, you're pre-product market fit, and you have five million dollars in the bank, that's more than enough. The differe…”
Founders Should Target 85th-90th Percentile Valuations Rather Than Maximum Pricing
“So as an example, as a founder, I always wanted, I don't know, the 85th, 90th percentile price, and I would still give people advice to do the same. Not the hundred percentile price, not the single best price.”
Nagpal Advises Founders to Take Secondary Liquidity When Offered
“But as a founder, I've multiple times given multiple of my companies, the advice, the founders rather advice that Go ahead, take the secondary, because if I was in your position, I would have done that.”
Emerging Market Startup Deals Require Higher Integrity Screening and Local Diligence
“I do think you sometimes have to screen for integrity a little bit higher and I'm Indian, so I can say that, but like, I do think, you know, like from a diligence perspective and stuff, the one thing I try and do is a little bit of local diligence because ther…”
Vibe Capital Will Slow Down Investments in Overheated Markets Like Pakistan
“But yeah, so right now, a lot of those markets are too heated, and we're going to slow down a little bit.”
Middle 80% of VC Funds Will Get Squeezed Out by Top Firms
“I think there's, like, this, like, 80% of everything else in the middle, I think, is who I think will compete it against from both sides. Like, if you're not amongst the best firms, or if you're not an operator that thinks like a founder, moves at the speed of…”
Mega VCs Should Back Operator Funds as LPs Instead of Acquiring Them
“I don't think it would be prudent of them to acquire these operator funds. They may choose to anyways, but it won't be prudent because I think what makes these funds special is the fact that they're independent, and that independence is what allows them to be …”
Nagpal Asserts That the Majority of VC Investors Detract Value From Startups
“I think the majority of investors take away value, not a ton, take away value.”
Venture Capital and Public Market Investing Will Blur Together
“With that, what I personally think will happen is I think venture and public marketing will kind of, right now, they seem like two distinct things. I think they'll keep sort of happening on a continuum where the differences will start becoming less and less.”
Vibe Capital Turned Down Recent Secondary Liquidity Offers From Large Firms
“I mean, just in the last two months, we've had the chance to sell out of positions. We're not going to because that would be stupid at this stage from large firms coming in and offering that kind of liquidity”
Venture Capital Investing Is Vastly Easier Than Operating a Company
“Having operated a company for seven years, there is nothing that we do as investors that is even remotely close to, you know, how hard actually running and operating a company is, which is why I know it's a cop out of an answer, but like literally nothing I do…”
Good Businesses at Cheap Prices Are Often the Worst Venture Investments
“My worst early investments were things that were frankly good businesses at great prices, and as a founder, you know, get trapped into being like, wow, this is actually a really solid business or profitable, the price is incredible, but then you realize this m…”