Harry Stebbings
659 statements across 343 episodes · 164 bullish · 270 bearish · 16 people on the record · first statement Jun 4, 2015 by James Altucher · said 2 times in 1 episodes since 2025 · across every show →
On the record as a speaker too: Harry Stebbings's record, appearances and statements → this page counts the times other people say the name.
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Everything said about Harry Stebbings, oldest first
Jun 4, 2015 negative
Jul 3, 2015
Jul 3, 2015
Stebbings Discovered VC at Age 12 Watching The Social Network
“I was sitting in the cinema watching The Social Network with Jesse Eisenberg, and I saw Peter Thiel and Clarion Capital investing in Facebook in that film, and I thought, that looks like a pretty, pretty sweet deal. And, you know, actually I think I was about …”
Jul 3, 2015
Jul 3, 2015
Jul 3, 2015 bullish
Nov 13, 2015 neutral
Feb 15, 2016 positive
Sep 21, 2016
Apr 3, 2017 positive
Harry Stebbings Reports 64% Open Rate on Snapchat Versus 36% Newsletter Rate
“I think for me in particular, the conversion is better than any other channel that I've seen. So if you compare it to like my newsletter, whereby I will have, say, a I think currently it's about a 36% open rate. My Snapchat is currently a 64% open rate”
Apr 3, 2017
May 8, 2017
May 8, 2017 neutral
May 8, 2017 positive
May 8, 2017
May 8, 2017
May 8, 2017
May 26, 2017 positive
Jun 14, 2017 neutral
Feb 16, 2018 negative
Aug 6, 2018 bullish
Jan 25, 2019
Jun 3, 2019 bullish
Jul 15, 2019 neutral
Sep 9, 2019 negative
Early-stage VCs regularly deploy millions without doing reference checks
“Having invested now for the past two years, I'm astounded by the lack of diligence and referencing that goes on. But this is millions being deployed earlier, and you will sometimes speak to a five million pound investor during the round and they'll go, you kno…”
Oct 4, 2019 negative
Stebbings: The advice 'nobody knows what they're doing' creates false comfort
“I think the most annoying bit of advice that I hear is like, oh, no one knows what they're really doing. And to me, it's just creates this false sense of comfort. And actually some people do know what they're doing in certain things”
Dec 6, 2019
Dec 9, 2019
Jan 6, 2020 negative
Jan 10, 2020 negative
Jan 17, 2020 bearish
Jan 27, 2020
Jan 27, 2020 neutral
Mar 9, 2020
Mar 13, 2020 negative
Mar 16, 2020 negative
Apr 8, 2020
May 11, 2020 negative
Stebbings: Seed funds cannot reliably build ownership in breakout startups
“With data transparency now, they come in very aggressively on anything that's popping, and the theory that you can build ownership over time, to me, is actually quite false, and I don't actually see it, because in the companies that are obviously popping, mult…”
May 11, 2020 neutral
May 11, 2020 negative
Stebbings: 2008 startup success came from platform shifts, not macro downturn
“For me, I strongly push back on that because I think they're conflating the macro economy with the technology advancements of GPS, of the rise of the app store and of the iPhone with the macro environment that was also simultaneously happening at the same time…”
Jun 1, 2020 negative
Jun 8, 2020
Harry Stebbings lost two investment deals by moving too slowly
“I've lost a deal, and it's happened twice, and the feedback was actually the same for me, which was great relationship with me. Trouble was, I wasn't there quick enough, and so, although the relationship was great, they had deeper, more trusting relationships …”
Jun 15, 2020 positive
Jul 3, 2020 negative
Stebbings: Customer acquisition cost is an unreliable metric at the seed stage
“I always actually slightly diminish the importance of kind of analyzing CAC at seed because it's so transient. It changes so much. It's so platform dependent. And really, it's just such an unreliable metric in my eyes, especially at this early stage.”
Jul 20, 2020 negative
Jul 27, 2020 neutral
Jerry Colonna: Genuine choice in work behavior requires full awareness of trade-offs
“And once you have consciousness, then you have choice. And if you choose to never take a vacation, Harry, do so consciously. If you choose to derive all of your self-worth and meaning from your job, do so consciously and fully conscious of the cost and benefit…”
Jul 27, 2020
Aug 17, 2020 negative
Aug 17, 2020 bullish
Sep 11, 2020 neutral
Sep 21, 2020
Oct 1, 2020 bearish
Stebbings: Multi-Stage Funds Pay $40M Seed Valuations Versus Standard $15M
“Bluntly, if multi-stage funds right now is the way that I see it, it's like completely price insensitive. I'm doing deals now where I end up not doing them because bluntly, they'll pay forty million pre when everyone else is paying 15, because they just don't …”
Oct 1, 2020 negative
Oct 22, 2020
Nov 9, 2020 bearish
Stebbings: Accepting early-stage capital from hedge funds is bad for founders
“So I think this is fundamentally bad for entrepreneurs. I don't mean to speak out badly against anyone. I'm sure they're great people. It's just fundamentally bad for entrepreneurs. Entrepreneurs in the way that, like, bluntly, as you said, it's a rounding err…”
Nov 12, 2020 negative
Dec 21, 2020 bearish
Jan 25, 2021 negative
Jan 25, 2021 positive
Libin: Founders should be the worst person at every job function
“So never hire someone whose job you can do better than them. Only hire people, only surround yourself with people that are ridiculously better than you or that are superior to you in their job or other things as much as possible. Like always be the worst perso…”
Feb 4, 2021
Stebbings: A 23-company VC portfolio captures 84% of diversification benefits
“And I've kind of, you know, run the numbers with a Monte Carlo attached to it. And you're like, actually, you know, like 23 gets 84% of the benefits of diversification. I think it is. And, you know, you only get an incremental seven or whatever it is for 40 co…”
Mar 15, 2021
Apr 5, 2021 negative
Jun 10, 2021 neutral
Stebbings: Early-stage VC relies entirely on founders because product is transient
“Market timing, I'm not smart enough to predict it. The product is transient. So all I've got in front of me is Scott and Mike and Jay, and do I fundamentally believe that whatever may happen, they might be the ones to guide it to where it could be.”
Jun 24, 2021 negative
Jul 8, 2021 negative
Jul 15, 2021 negative
Stebbings: Childhood unpopularity caused adult struggle with overcommitting and people-pleasing
“I think one of the results of me being unpopular when I was younger was like, now I'm just like this inherent people pleaser, and I like to say yes to everything, but it's a real problem for me, Nick, because I let people down because I say yes to everything.”
Aug 2, 2021 negative
Stebbings passed on an $8B company at a $6M seed valuation
“It was because I listened to a reference From a former boss, and it said what a terrible employee they were, and what a terrible employee they were, and I was like, oh no, and I took that very seriously, and I didn't make the investment. Six million pre, now i…”
Aug 19, 2021
Nov 24, 2021
Jan 10, 2022 bearish
Feb 2, 2022
Stebbings passed on a $6B company due to a bad reference check
“I missed a company like a five million pre that's now a six billion dollar company because I listened to the reference on the founder, and they said he was a shit employee, and he was, you know, Opinionated and rude and all these things. And it was wrong. He w…”
Feb 5, 2022
Feb 14, 2022 negative
Feb 18, 2022 negative
Mar 1, 2022 bearish
Mar 11, 2022 bullish
Mar 16, 2022 positive
Apr 8, 2022
Apr 8, 2022 bearish
Apr 11, 2022 positive
Apr 11, 2022 negative
Apr 25, 2022
Stebbings: Sending VCs three relevant deals monthly for six months gets hires
“Show the freemium version of yourself. Like, choose five VCs that you want to work with. Like, all of our portfolios are very public. Understand the type of deals they like, and for six months, send them three deals every single month. And after six months, Di…”
Apr 25, 2022 negative
May 6, 2022 negative
May 16, 2022 negative
May 24, 2022 negative
Jun 6, 2022 negative
Jun 8, 2022 negative
Jun 10, 2022
Jun 17, 2022 negative
Jun 24, 2022 neutral
Jun 24, 2022
Stebbings: Collect feedback on Word docs to ensure unencumbered team opinions
“I make people comment on Word docs, not on Google docs, because then they send them back to me the night before, and then I can pick on them in the meeting and say, hey, in the Word doc you said this, and their opinion is unencumbered by others, where it would…”
Jun 27, 2022 negative
Jul 2, 2022 negative
Aug 8, 2022 positive
Aug 15, 2022 negative
Aug 15, 2022 negative
Stebbings: High GP Commitments Drain Management Fees and Harm Fund Quality
“I also find it moronically because you insist on a certain bar, the managers can't do it out of their own personal capital. And so then they pay for it out of fees. And then that means that they are fundamentally capped from reinvesting in their own teams, pla…”
Aug 15, 2022 negative
Stebbings Missed $25M in Liquidity by Following Sequoia's Advice to Hold Winners
“My biggest regret and my biggest lesson is that I didn't, because I believed in Sequoia's, hold on to your winners, never sell your winners, and I didn't, and I probably could have taken off about twenty five million dollars for an eight million dollar fund.”
Aug 15, 2022 negative
Aug 15, 2022 bearish
Aug 24, 2022 positive
Aug 24, 2022 positive
Aug 24, 2022
Aug 24, 2022 negative
20VC Abandoned 100,000 Snapchat Followers Due to Declining Engagement
“I invested heavily in Snapchat stories when they were big for business. We gained a 100,000 plus fans there, but with the reducing popularity of the platform for business, The audience declined, and it was no longer worth the investment for me over other platf…”
Aug 24, 2022
Aug 24, 2022
Aug 24, 2022
Aug 24, 2022
Aug 30, 2022 positive
Market conditions matter more than founder quality in startup success
“Mine was most importantly that actually the market is more important than the founder. And what I mean by that is if you are in an untenable market, Even the best founder will not be able to get out. Like, truly untenable. Social, political unrest. Currency de…”
Sep 7, 2022 negative
Stebbings: VCs give vague rejections to preserve optionality for future rounds
“The reason that investors aren't as directors, they should be most often in terms of the feedback is because they want to retain the optionality. If you're a multi-stage fund, You don't want to say, Mike, I'm turning you down at the seed because I really don't…”
Sep 7, 2022 negative
Sep 7, 2022 negative
Sep 7, 2022 bearish
Stebbings: Bearish on creator economy due to extreme 99/1 Pareto distribution
“I'm not bullish on the creator economy and I'm not bullish on the creator economy for the simple reason that I think it follows the most extreme version of Pareto's principle. Where 99% of revenues accrue to one percent of creators.”
Sep 7, 2022 negative
Stebbings: 20VC Fund I's biggest mistake was blindly following another investor
“I look back at the fund one in particular, 20 VC fund one, biggest mistake I made was one specific check went terribly wrong very quickly. And it went terribly wrong. And I blame myself. I relied so heavily on someone else who knew the market so well and just …”
Sep 12, 2022 negative
Stebbings: Market dynamics matter more than founder quality in startup success
“I lost money recently because I invested in a company And the founder was world class. Fantastic founder. But in a market that, hell or high water, you could not make money, and then the business was no longer able to exist. And I learned, actually, market win…”
Sep 12, 2022 negative
Sep 16, 2022 negative
Stebbings: Public visibility and politicization are the top challenges for modern leaders
“I think the hard thing now is actually being public is part of the job, actually. Do you know what I mean? And that's a big change that we've seen. That and the politicization of leadership, I think, is the biggest challenges that, that leaders face today.”
Sep 23, 2022
Oct 1, 2022 negative
Oct 1, 2022 positive
Stebbings: Seed founders should raise $4M over $2M for runway
“I disagree with you on the raised side, and I disagree with you, because bluntly, I feel that fundamentally, it's very rarely the first V-one that actually hits... I would always favor the four. As I said, it's worse for dilution, but I think for company build…”
Oct 7, 2022 negative
Oct 14, 2022
Oct 21, 2022 negative
Stebbings: Claiming "nobody knows what they're doing" in business is bullshit
“You know one of the biggest bits of bullshit advice I think there is, which is like, oh, don't worry, no one really knows what they're doing. To me, this is complete crap. People do know what they're doing, which is why they're often where they are, and you sh…”
Oct 21, 2022 neutral
Stebbings: Raising a $2B fund is easier than raising $200M
“It gets to a stage with also fund sizes, Kyle, where it's almost easier to raise two billion than it is two hundred million, and the reason I say that is because there is a pool of LPs, as you know, the pension funds of the world, Who need to move a hundred mi…”
Oct 31, 2022 negative
Harry Stebbings: Lost money on an investment for the first time in 2022
“So I lost money for the first time earlier this year, and my takeaway was actually that no matter how world class the founder, no matter how brilliant the team is, if they're in a market which is just inherently fucked, challenging, vulnerable, no team can get…”
Nov 4, 2022 negative
Nov 4, 2022 neutral
Stebbings uses isolated Word documents for committee feedback to prevent groupthink
“So the way I do it is I send out actually a Word doc, not a Google doc, because that's obviously collaborative. I sent out a Word doc the night before. So it's all in isolation. No one sees what other people put. And then they have this kind of free space to r…”
Nov 4, 2022
Stebbings forms custom three-founder investment committees for every 20VC deal
“Through the media, I meet the world's most brilliant founders, and with each deal, I create an individual investment committee of three leading founders in that specific space, and I bring their collective minds to make the best decisions together.”
Nov 19, 2022
Nov 19, 2022
Nov 21, 2022 negative
Stebbings: Hot seed rounds raised by executive founders consistently underperformed
“I looked at the seeds, and I looked at those that haven't really worked, and all of those that haven't really worked have often been head of product at Twitter, head of product at Twitch, head of product at amazing company, the hottest of hot seed rounds with …”
Nov 21, 2022 negative
Nov 21, 2022 negative
Stebbings: Board member value follows a barbell distribution, skipping mid-stage VCs
“The other truth is I think there's a utility value to board members that resembles a barbell, which is like Fenton, Gurley at the A you know, Alfred Lynn at the A, Roloff Botha at the A, amazing Pat Grady at the A, great, and then your pre-IPO people who are a…”
Nov 21, 2022
Nov 21, 2022 neutral
Nov 28, 2022
Nov 30, 2022 negative
Stebbings: Pakistani startup Airlift was his biggest fund loss
“My biggest fuck up in this fund cycle was a company called Airlift in Pakistan. I thought I knew better. I analyzed the market to the end of the world, the opposite of FTX. I did more diligence than anyone could have done, and actually, I'd never been to Pakis…”
Nov 30, 2022 positive
Dec 9, 2022 positive
Dec 21, 2022
Dec 21, 2022
Stebbings: Treat angel cap table assembly like building a sports team
“When planning your angel allocations, I always advise founders to assemble their angel cap Table as they would a sports team. Each person has a specific position which they are specialized to and have a world-class skill in. So you have someone for marketing, …”
Dec 21, 2022 negative
Stebbings: Limit initial pitch calls to two team members max
“If you're doing a Zoom call and it's a first meeting, do not have more than two people on the call from your team. It makes it tough to really get to the core of the discussion, and removes a lot of the relationship building with Too many people on a call too …”
Dec 21, 2022
Stebbings: Immediately align with new lead VCs on milestones for next round
“In preparation for the next round, the most important thing is investors invest in lines and not dots, and so I would sit down with your new leads and align in that first meeting on five names that would be ideal leads for the next round, and then also clearly…”
Dec 21, 2022 positive
Stebbings: Founders should pitch lower-priority VCs first to refine pitch
“They go to their priority names first. Do not do this. Your pitch both in delivery, style, and messaging will improve so much with each meeting. Start with a couple of investors where, respectfully, you would not be so sad if they said no.”
Dec 21, 2022
Stebbings: Give larger check allocations to fewer angels to maintain engagement
“A massive mistake I see often, is founders who try to cram down all their angels to their smallest allocation so they can fit in as many as possible. Do not do this. Give less people More allocation. It's really important that the check size that you give them…”
Dec 21, 2022 negative
Dec 21, 2022
Dec 21, 2022
Stebbings: Exit slides in pitch decks encourage short-term investment thinking
“Exit slides have no place in the slide deck. I do not see this so often now, but it really just attracts the wrong type of investor if they're looking for an exit on the day of their investment. It encourages short-term investment thinking.”
Dec 21, 2022
Jan 9, 2023
Jan 11, 2023
Jan 11, 2023 negative
Stebbings: Late-stage angel checks fail to prove seed investment capability
“This does not prove you are a good seed investor, but it merely shows you have access to series B and series C investments. These are very different things, and actually can only serve to discredit you often, as it shows a little bit of naivety.”
Jan 11, 2023 positive
Jan 11, 2023 bearish
Jan 11, 2023
Stebbings: I meet two new LPs weekly and email quarterly updates
“In terms of how I think about relationship building with LPs, I always meet two new LPs every week. Two new LPs every week. I then ensure with every quarter, I have a check-in with them, and ensure that they each have a quarterly update. I email them personall…”
Jan 23, 2023 negative
Jan 23, 2023 bullish
Jan 31, 2023
Jan 31, 2023 neutral
Stebbings: Vintage diversification was irrelevant for VC returns over the past decade
“I think vintage diversification, you'll really see the benefits of in this next cycle. Yeah, I look at mine now, and it's like, I'll have some 20, 21 pricing in there, but I'll always have 23, 24 pricing in there. And I think that's really where you see it, be…”
Feb 13, 2023 positive
Feb 13, 2023 negative
Feb 13, 2023 bearish
Feb 13, 2023 negative
Feb 18, 2023 neutral
Harry Stebbings: VCs focus on incremental milestone de-risking between funding rounds
“I think the other thing that people forget with VCs is we think in increments, people often think they want to see like the twenty billion dollar outcome. And yes, we absolutely do, but we also want to see where the next round comes from.”
Feb 18, 2023 negative
Feb 27, 2023 negative
Feb 27, 2023 positive
Stebbings: Active reserve management separates 0.7x funds from 2x funds
“In the bad, bad times, when you do the studying, actually the intense portfolio managers are the difference between one x, or naught .7 x, and two x, because they've religiously managed a huge amount from reserves, liquidity, and everything in between”
Feb 27, 2023 bearish
Stebbings: Big tech spinouts raising $5M-$7M seeds are my worst investments
“And so they're my single worst investments. Those are my worst ones when they've spun out of any great company and they've raised five to seven. Because they're inherently slower because they're used to the processes of Twitter, of Facebook, the HR, the polici…”
Mar 8, 2023 positive
Mar 17, 2023 positive
Stebbings advocates forming formal startup boards at pre-seed and seed stages
“The conventional wisdom is that you shouldn't have boards too early, but the more I do pre-seed and seed, the more I think you should have them as early as humanly possible, and I do, and it's not an arrogance, it's just like, as an investor, you see hundreds …”
Mar 24, 2023 negative
Stebbings: Partner churn at multi-stage funds hinders Series A fundraising
“The one thing I think does make a difference is when you have partner churn at multi-stage funds, so if you can be orphaned at multi-stage funds, even if you do well, if there's no real owner, it can be a lot more difficult to have your internal champion to le…”
Mar 24, 2023
Mar 24, 2023
Mar 24, 2023 negative
Apr 7, 2023 positive
Apr 17, 2023 positive
Braun: LPs Back Young VCs Based on Character, Not Achievements
“They're betting on you because they like you and they want to see you win. That's the truth. That's the part you're missing. They're betting on you because of who you are, not necessarily what you've achieved, because there's a lot of other people who are much…”
Apr 28, 2023 negative
Apr 28, 2023 negative
Apr 28, 2023 negative
Apr 28, 2023
Stebbings: $250 Diet Coke promotion pushed 20VC to #2 in UK
“I remember going with three friends to a football stadium, and having 500 Diet Coke cans strapped in, like, drinks, rucksacks, and saying, we'll give you a free Diet Coke, if you'll give us your phone for a review. And we spent, like, the 50 P each, so like, a…”
Apr 28, 2023 bearish
May 9, 2023 bullish
May 10, 2023 positive
May 22, 2023 bearish
May 22, 2023 bullish
May 22, 2023 negative
May 22, 2023 negative
May 22, 2023 negative
Stebbings passed on Riverside because he doubted podcasters would pay
“I really regret Riverside. Oh, fuck me. Ah. Fucking Oran Zeve, who I love. Yeah, he's great. Amazing dude. Brought it to me, and I said, no one will do this. You know why? Because like, 90% of podcasters don't earn more than a hundred dollars a month. It's 50 …”
May 24, 2023 bearish
May 24, 2023 negative
May 24, 2023 positive
Jun 5, 2023
Jun 19, 2023 negative
Jun 21, 2023 negative
Jun 21, 2023 negative
Jun 23, 2023
Jun 23, 2023
Jun 23, 2023 negative
Harry Stebbings: Smaller LPs Require Disproportionately More Time to Manage
“I find the smaller checks more painful to manage. They're less educated, but often this is not unison, but often they can be less educated, less informed on venture. And actually they take a lot more time and care than almost the bigger LPs who are much more i…”
Jun 26, 2023
Jun 26, 2023 negative
Stebbings: The younger generation of workers is lazy and expects high compensation
“I think this generation is fucking lazy. They do not work, sorry, I'm on a rant now. They do not want to work hard, they do not want to come into the office, they get paid top dollar, and actually, they want great package, they want all of this, and they don't…”
Jun 26, 2023 positive
Stebbings: Startups must focus on brand, PR, and diversity early on
“I think that PR and brand, often it's a bit like culture, and it's a bit like hiring diversity, which is people go, at a stage of time, I will focus on it. But at that stage of time, you're 50 white dudes in an office, and it's really hard to layer on diverse …”
Jun 26, 2023 negative
Jun 28, 2023 negative
Jul 10, 2023
Jul 10, 2023
Stebbings: A massive tax bill halved his wealth and shattered his self-worth
“I had a tax bill not long ago, and it was horrifying, and yeah, I felt a lot less of a person. I always identified as bluntly the rich one in my family, or the rich one in my friend group, and suddenly I was halved in that one half, and I felt significantly le…”
Jul 17, 2023 negative
Jul 21, 2023
Jul 21, 2023 negative
Jul 21, 2023 negative
Jul 21, 2023 positive
Jul 26, 2023
Jul 26, 2023
Stebbings: Angels need uniform check sizes and at least 25 investments
“Lesson one, you don't have conviction at the early stage. Just do 25 K, 10 K, 50 K, I don't care, but same check size. Number two, you need 25. This idea that you're a genius picker, you're not. No one is. Five is not enough. You need 25.”
Jul 26, 2023 negative
Stebbings: Operating experience decays faster today than ever due to AI
“I also think like the rate of decay on operating experience has never been greater, like specifically on two, which is like, if you haven't operated in the world of AI, it's fundamentally different thinking kind of AI first and with AI as part of your stack th…”
Aug 9, 2023 positive
Stebbings: Older and repeat founders avoid blase attitudes toward fundraising
“That's why I prefer one older founders and two serial entrepreneurs. I find with both, you do not get both of those situations. You don't get the blase. Oh, I'll raise it a 106 months time. And you don't get the flippant. Why do you care? Kind of moody.”
Aug 11, 2023 bearish
Stebbings: $50M to $100M funds are too small to lead seed rounds
“Say if you have a fifty million dollar fund size, you've got forty million investable, you want to do seed today with the average seed being three to four, you can't lead seed rounds with that and have enough diversification. You got twenty two million dollar …”
Aug 14, 2023
Aug 14, 2023 positive
Aug 14, 2023 bullish
Stebbings: AI verification challenges will drive value to existing media brands
“Verification as a layer becomes one of the most valuable, but I think value accrues to existing media brands because verification becomes more and more challenging. And so the authentic followership that we have, Becomes more valuable because it becomes more a…”
Aug 14, 2023 positive
Stebbings: Winning at modern content is purely a game of volume
“Volume is everything today. It is purely a game of output. You need YouTube shorts, you need Instagram reels, you need TikToks, you need podcast episodes, you need blog posts, you need Twitter threads, you need to be everywhere because attention is currency, a…”
Aug 14, 2023 bullish
Aug 23, 2023 neutral
Aug 23, 2023 negative
Sep 6, 2023 negative
Stebbings: European AI seed rounds are heavily misreported by the media
“I think the funding rounds are very misreported. And what I mean by that is like, there's definitely been some in Europe where like, you know, a hundred dollar, a hundred million dollar rounds are reported on two fifty million dollar valuations. If you actuall…”
Sep 6, 2023 negative
Stebbings: High-valuation pre-seed rounds by former VPs are my worst investments
“But like, my worst performing, and I've done a 150 investments now, the worst performing ones are always the stellar VP that comes out of the stellar company and raises 10 on 40 as the pre-seed. They are always the ones which slowly meander to either a bad hac…”
Sep 6, 2023 negative
Sep 13, 2023 bearish
Sep 13, 2023 negative
Stebbings: Passing on Riverside and Descript were my biggest investment misses
“You've articulated why I've missed my biggest misses in investing, which is Riverside and it's Descript. And I miss them both because I said, the only thing creators care about is do you bring me more cash or more fans?”
Sep 18, 2023 neutral
Sep 18, 2023 negative
Sep 18, 2023 negative
Stebbings: Not knowing basic SaaS metrics like LTV is unacceptable for founders
“With the freedom of information today, with the transparency of podcasts like this, the availability of SaaS materials, basically, That's not an acceptable thing, I think, if you're gonna start building a SaaS company. This is the core mechanics of any busines…”
Sep 20, 2023 bullish
Stebbings: Series A currently offers better risk-adjusted value than seed
“I think that's why Series A is actually the most attractive place to be investing right now, because actually many of them have been significantly de-risked, but because of the markets today, the price inflection is actually significantly lower and less than i…”
Sep 20, 2023 neutral
Sep 20, 2023 bullish
Sep 20, 2023
Sep 27, 2023 neutral
Sep 27, 2023
Sep 27, 2023 negative
Stebbings: Success across multiple founder and investor roles is zero-sum
“I constantly feel guilty, because I constantly feel like I'm failing as a son, as a brother, as a boyfriend, as a fund manager, as an entrepreneur. There's so many different fucking hats. That if I'm winning in one, I'm by nature failing in another.”
Sep 29, 2023 negative
Oct 2, 2023
Stebbings: My Main Investment Flaw Is Falling for Smooth Salespeople
“If I reflect on my own as an example, I fall for the brilliant salesperson, the one who is incredibly smooth and articulate and can present that three chapters, but their operational execution ability is Not as good as actually their sales ability. And then th…”
Oct 2, 2023
Oct 2, 2023 negative
Stebbings: 20VC Lost Focus by Interviewing Non-Venture Guests Like Pop Stars
“I've never actually spoken about this, but I think actually I lost my way with the content that we did about a year ago. I was overly focused on growth, bluntly, and I started doing things with different guests that weren't venture, and you would have a pop st…”
Oct 2, 2023 negative
Stebbings: Peak Venture Achievement Requires Relentless Solo Focus Without Family
“You can always go further alone without another half, without kids, when it is just you at your desk, meeting founders, focusing, focusing. You can do so much more. It is a young person's game of grind and hours, is what I've come to realize.”
Oct 2, 2023 bearish
Stebbings: Venture Capital Platform Talent Teams Are Largely Ineffective
“Talent teams are largely BS unless you really invest in them because the diversity of roles that people will come to you for means that essentially you just become a job description writer, because if you're hiring a CMO, it's totally different to a head of de…”
Oct 2, 2023 positive
Stebbings: Market Structure Matters More Than Founder Quality in Venture Capital
“No matter how good the entrepreneur is, fuck it, sorry, if the market is so challenged, which emerging markets are right now. There are great businesses in emerging markets, which will never raise because all us cash is golf for anywhere in the majority of eme…”
Oct 6, 2023 positive
Stebbings prefers backing repeat founders to avoid funding first-time mistakes
“I, as a result, favor second time or serial entrepreneurs Because I believe that there are so many things that you fuck up the first time that you will not do the second and third, and I then won't have to stay for those learnings.”
Oct 16, 2023 negative
Oct 18, 2023 bearish
Oct 18, 2023 bullish
Oct 18, 2023
Oct 18, 2023 bearish
Stebbings: Tech IPO market will not re-open until H2 2025
“But I think it's going to be longer. Like, you know, it, you'll see it in the update coming out this weekend, but it's like, you know, data breaks, stripe, it's not going to be enough to actually crack open the IPO markets like we think it will be, I don't thi…”
Oct 18, 2023
Oct 18, 2023
Oct 20, 2023 negative
Oct 20, 2023 positive
Oct 20, 2023 positive
Top VCs Succeed by Strategically Trimming Best Positions, Not Doubling Down
“The best actually strategically lent out of their best positions, and so I think we'll see a movement away from the momentum, portfolio management, liquidity management doesn't matter, to actually the best returning managers being incredibly disciplined around…”
Oct 20, 2023 neutral
Oct 23, 2023 negative
Oct 23, 2023
Oct 23, 2023 positive
Oct 27, 2023
Oct 27, 2023 negative
Oct 30, 2023 bearish
Nov 1, 2023
Stebbings: I might have quit early if I knew audience growth took years
“It's hard, but I didn't know, actually, that it would take years and years to build a following to the millions. If I had have done, I might have quit earlier. I thought it would come much sooner, and actually, it was just fun, and so I went along with it.”
Nov 3, 2023 negative
Nov 6, 2023 positive
Nov 8, 2023 bullish
Nov 8, 2023 positive
Nov 8, 2023 positive
Nov 8, 2023 bearish
Nov 15, 2023 positive
Stebbings: Early investors should take secondary liquidity when valuations peak
“Actually, regardless of how well the company's doing, regardless of trajectory, who's joining rounds, if you are in early enough, and the prices get high enough, just take some off the table. And actually be much more active around it. Like, you know, be a rea…”
Nov 17, 2023 negative
Nov 17, 2023
Nov 20, 2023 negative
Stebbings: Candidates staying 1.5–2 years only deliver six months of actual work
“I hate bouncers, I call them, which is, as you said a couple of times, five, six jobs. I'm like, if you're somewhere for a year and a half, and another for two years, and another for a year and a half, with ramp time and leaving time, You basically did six mon…”
Nov 22, 2023 negative
Stebbings: Complete startup failures going to zero are rarer than believed
“Actually, I think this is a gross over exaggeration on the mortality rate of startups, which is like going to zero is actually rarer than people give credit for. It could be half your money back. It could be a one X, whatever it is, but it's actually rarer tha…”
Nov 22, 2023 negative
Nov 22, 2023
Stebbings turned down a 50x angel return offer in Fast
“I had this offer and I was like, ah, it's like, it was like a 50 X on an angel check. And I was like, no, I buy it. Like I'm going to stay in here. Stripe have just come in. There's going to be a partnership agreement there. No, I should have fucking been fear…”
Nov 22, 2023
Nov 29, 2023 negative
Stebbings warns against customer concentration in high-growth startups
“I hate companies. Whereas I, we're just selling to like high-grade startups. And I'm like, yeah, there's that thing called a macro recession that's going to impact spending and funding. You know, I don't like concentration on customers basically.”
Nov 29, 2023 negative
LTV is a useless metric for early-stage startups, argues Harry Stebbings
“The assumption that we can have eight to nine years as an LTV in the first two years of a company, I get it more if you're Visa, where we've got 50 years of data, but like for a startup, I just think LTV is bullshit. You've got no freaking idea.”
Nov 29, 2023
Nov 29, 2023
Dec 1, 2023 positive
Dec 1, 2023 positive
Dec 4, 2023
Stebbings originally created 20VC for personal learning, not public release
“That's actually why I started it, by the way. I didn't actually intend to release them. People don't know that. Yeah, I just wanted to learn from great people and realize that it was the best way to people to give me time.”
Dec 8, 2023
Stebbings: 98% of multi-billionaire founders worry about raising ambitious kids
“And I've, again, spoken to something crazy, like a hundred multi-billion dollar founder CEOs with children. And 98 said that essentially teaching children to have the same level of hunger and ambition Despite being brought up in a much more affluent family is …”
Dec 8, 2023 negative
Dec 11, 2023 negative
Stebbings: Founders Who Do Not Know Market Competitors Are Poor Quality
“Do you know, I think that's a poor quality founder. I'm like, if you don't know your market, if you were to ask me about fund or media competition, I could tell you everyone break them down by pros and like, that's just a bad founder.”
Dec 11, 2023 negative
Dec 11, 2023
Stebbings: Incremental title and salary increases are key to talent retention
“Little and often is my secret to retaining great talent. And what I mean by that is you have title and salary, and I increase them separately, but little and often to create that kind of feeling of forward momentum more frequently.”
Dec 11, 2023 negative
Dec 11, 2023
Dec 11, 2023 positive
Dec 13, 2023 negative
Dec 15, 2023
Dec 18, 2023
Dec 18, 2023 positive
Stebbings: Indirect reference questions reveal a manager's key weaknesses
“I always ask, like, you know, if we were hiring someone underneath Peter to support him, what skills would they have? And they go, oh, well, that'd be super organized, that'd be very rigorous and analytical. That's right. And you're like, huh, okay, you just t…”
Jan 4, 2024 bearish
Jan 12, 2024 negative
Jan 12, 2024
Jan 19, 2024
Jan 22, 2024 positive
Jan 22, 2024 positive
Jan 22, 2024 positive
Stebbings: All great entrepreneurs show entrepreneurial drive in early childhood
“The greatest entrepreneurs I find of all time when I look at pattern recognition on the people we've had on the show is all the best entrepreneurs made money or showed entrepreneurial signs in some way in their childhood. I made websites. I sold lemonade. I so…”
Jan 24, 2024
Jan 26, 2024 negative
Jan 29, 2024 negative
Stebbings: In-house VC IR teams weaken GP-LP relationships and direct deals
“I find IR teams respectfully, and there's nothing against them, but they just create a layer that removes from the human relationship with the GP. I think it also impedes your ability to get good directs, because you lose that messaging with Neil, or messaging…”
Feb 2, 2024 neutral
Feb 7, 2024 bearish
Feb 7, 2024 negative
Feb 26, 2024
Stebbings: Decouple title and salary raises to boost employee retention
“I think little and often is my biggest lesson. And what do I mean by that? It's like break apart, like title and then salary or finances and then increase one of them little and often. So they continuously have hits. And this is like once every six months, con…”
Feb 26, 2024
Mar 4, 2024 negative
Mar 11, 2024 negative
Mar 18, 2024
Mar 18, 2024 negative
Mar 20, 2024 bearish
Mar 22, 2024
Mar 25, 2024 neutral
Mar 29, 2024 negative
Stebbings refuses to hire or invest in people with unbroken track records
“There's a reason why I would never hire them or invest in them. Those guys are the ones that break the minute something breaks. They never ever have experienced being bullied, being the fat kid in the corner with no friends.”
Mar 29, 2024 negative
Stebbings: Great ambition stems from childhood, not top consulting firms
“It's why whether I'm hiring you or I'm investing in you, I will always go back to your early childhood. No great person who was hugely ambitious fell out of McKinsey and Bain and thought, oh, now I'm going to be really ambitious and courageous.”
Mar 29, 2024
Apr 3, 2024 negative
Stebbings: Raising $2M at $20M Valuation Excludes Top-Tier VCs
“When I see like two on 20 YC rounds and I'm like with two on 20, you're automatically excluding any top venture firm because really the 1.6 is going to be available for a lead, which is what? 7.8%. You're not going to do something for 7.8%. It's not worth your…”
Apr 3, 2024 negative
Stebbings: Prefers Legacy Sectors Over Competing With AI Giants
“For me, it's like a non-competitive industry. I never want to compete against fucking Sam Altman doing foundation models and Dario from Anthropic and Satya at Microsoft. I want, like, legacy architecture. I want, like, high pricing power. I want really, really…”
Apr 5, 2024
Apr 5, 2024 negative
Apr 5, 2024
Harry Stebbings: Top entrepreneurs always show early signs of exceptionalism
“The best entrepreneurs show early signs of exceptionalism always. It could be in sport. It could be in a business. They start very, very young. It could be in designing websites for local businesses, but there's always a sign of exceptionalism early.”
Apr 12, 2024 negative
Stebbings: Enterprise Sales Teams for $10K ACV Products Rarely Scale
“And the ACV is a 10 K and it's like, ah, and they're like, ah, but it'll scale. It'll scale, Sam. It rarely scales. And so we're layering on this enterprise cost base for this very SMB PLG revenue base, which has really been born out of the PLG motion. And I'm…”
Apr 15, 2024 bearish
Apr 17, 2024
Apr 17, 2024 bearish
Stebbings: Software developer tools is an inherently terrible venture market
“Dev tools. What a shit market. Devs like to build their own tools. Like, they don't believe anything you tell them, and so they just are inherently skeptical. They expect insane product. They're very cynical. The margins are generally quite crap. The CS is req…”
Apr 17, 2024 bearish
Apr 17, 2024
Apr 22, 2024 neutral
Apr 24, 2024 positive
Stebbings: Serial Entrepreneurs Are Better Investments Than First-Time Founders
“I don't like first-time founders like I like serial entrepreneurs, because you've just seen it, you know how to do hiring processes, you know what great looks like, you've avoided, you've seen the mistakes, you've made them.”
Apr 24, 2024 negative
Apr 24, 2024 negative
May 8, 2024
May 8, 2024 positive
May 8, 2024
May 8, 2024 negative
May 22, 2024
May 31, 2024
Stebbings: Pay job candidates for a one-week stealth trial before hiring
“I always think, actually in most roles, it's about a week, which is why I try and pay people to take a week off their job beforehand. I say, hey Matt, it's a big decision for you. Let's pay you for a week, join for a week in, in kind of quiet, and we'll see if…”
May 31, 2024 neutral
Jun 3, 2024 positive
Stebbings: 20VC holds a $60M stake in a $3B foundation model startup
“I was laughing with our CFO this morning, because we've got a company where we did the first round for when it was a SaaS company, pivoted to a foundation model, and now it's worth three billion. You can't get fucking liquidity on it, Jason. So like, we own tw…”
Jun 7, 2024 positive
SDRs should host podcasts interviewing target buyer personas to generate leads
“You choose your ICP. Start a podcast interviewing the world's biggest and best in that ICP. If I worked for you, this is what I'd do. You'd give me a segment. I'll start a podcast interviewing the biggest, I don't know, CHROs in software companies between 505,…”
Jun 7, 2024 positive
Jun 12, 2024 bullish
Jun 17, 2024 negative
Jun 19, 2024 neutral
Stebbings: Fund 1's top drivers were mediocre-seeming startups, while rocket ships failed fastest
“I look at my fund one, which is a tiny, yeah, eight million fund. Actually, our best value drivers today were all in the meh. And the worst performing companies were all in the rocket ship category. They're the ones that went to zero quickest.”
Jul 1, 2024 positive
Jul 3, 2024 positive
Jul 8, 2024 negative
Stebbings: Exceptional founders never come straight from McKinsey or Bain
“One of the most clear signs for me of an exceptional entrepreneur is they always start early. They always sold Nokia mobile phones on eBay. A lemonade stand at school, you know, whatever that may be. You never came out of McKinsey or Bain and made your first e…”
Jul 10, 2024 negative
Stebbings: Delaying 20VC's YouTube launch for six years was my biggest mistake
“The biggest strategic mistake that I made was I waited six years to go to video. I thought that actually people felt much less comfortable on video. I felt that they would close up more and we didn't do YouTube for six years as a result.”
Jul 10, 2024
Jul 10, 2024 negative
Jul 15, 2024 positive
Jul 15, 2024 positive
Jul 15, 2024 positive
Jul 15, 2024
Jul 15, 2024 positive
Jul 15, 2024 negative
Jul 17, 2024 negative
Jul 22, 2024
Stebbings: Pre-seed angel investors should write uniform check sizes for every deal
“Write the same size check every deal. Like, everyone thinks, oh, I get different conviction levels. I'll write a hundred K check, and I'll write a 25. You're not that smart at pre-seed. Just write 50 K checks every time.”
Jul 22, 2024 negative
Jul 24, 2024 bullish
Jul 24, 2024 bullish
Jul 31, 2024 negative
Aug 2, 2024 positive
Aug 5, 2024 negative
Aug 5, 2024
Aug 7, 2024 negative
Aug 9, 2024 positive
Aug 16, 2024 negative
Aug 16, 2024 negative
Aug 16, 2024 negative
Aug 21, 2024 positive
Sep 6, 2024 negative
Stebbings: $5M on $25M seed rounds are my worst investments
“The worst category of seed investments that I've made have been five on 25. They are slower. They lose urgency. They try and do too much too soon because they can do more than one thing at once. The founders lose proximity to customers. They're the worst.”
Sep 6, 2024 negative
Stebbings: I should have sold secondary positions in Clubhouse, Hopin, and BeReal
“Truth be told, honestly, Nick, I've been in some rockets that then turned out to not be rockets. Your clubhouse to your hop in to your be real. And they are portfolios with assets in, whether you like it or not in terms of naming. And I should have been much m…”
Sep 6, 2024 bullish
Stebbings: Downside liquidation preferences can add half a turn to fund returns
“Those provisions exist for a reason, which is because in harder times, being able to get back one X, not 0.2 X actually across several companies, which is often the case makes a big difference. It can make a half turn on a fund.”
Sep 11, 2024 positive
Stebbings: Competitive athletes make great salespeople due to pain tolerance
“I actually like it when you find competitive athletes who turn into sports Reps and sales reps or salespeople. They can endure great pain for long periods of time for delayed gratification. It's like a core trait, I think, of sales.”
Sep 13, 2024 positive
Sep 16, 2024
Stebbings: Investors fail by copying others instead of leaning into unique strengths
“After 2700 shows, I've learned that one of the biggest mistakes people make is they try and copy someone's style that's not authentically theirs, and think that's the right one. And actually, it's about finding where you are uniquely great in the three pillars…”
Sep 16, 2024 positive
Sep 18, 2024 negative
Sep 20, 2024 negative
Stebbings: Tinder does poor product marketing for its subscription tiers
“I would argue that Tinder do bad product marketing on their different packages. I have seen them, and I don't really get what I'm getting for each of them, and so I'm like, ah, I'll go to Bumble. That, so, so the way that you described it, I go on and I'm like…”
Sep 20, 2024
Stebbings: Growth teams should optimize seats per contract, not top-line revenue
“The biggest mistake that I see as an investor today, you know, with the investing hand, it's like focus on revenue and it's actually like actually seats per contract drives the total revenue size. And so the growth team should be focused on what product change…”
Sep 20, 2024 positive
Sep 20, 2024 bearish
Stebbings: Consumer Subscription Is Not a Venture-Backable Category
“But I don't think consumer subscription as an asset class, as a subcategory or category, is a venture-backable large enough category. There might be one like Duolingo, and maybe a couple more? But that make it to venture scale returns.”
Sep 23, 2024 negative
Oct 4, 2024
Framing product questions around MrBeast or Jony Ive unlocks distinct ideas
“So I'll say, what would Mr. Beast do if he was running our product today? And then what would Johnny Ive do if he was running our product today? And from the same person, you will get multiple different answers with that image of that person in mind.”
Oct 14, 2024 negative
Oct 14, 2024
Oct 14, 2024
Oct 14, 2024 bearish
Oct 14, 2024 negative
Oct 16, 2024 positive
Oct 21, 2024
Oct 23, 2024
Oct 23, 2024 negative
Harry Stebbings: Truly sharp people avoid tech sales account executive roles
“If you, if you're a really sharp, insightful person, you're not going to be an AE. I'm going to get killed by a whole AE audience. But like, if you're really sharp, I can make money in so many better industries. It's tough. Sales is fucking hard.”
Oct 23, 2024 negative
Oct 25, 2024 bullish
Stebbings: VCs in AI era should take low-ownership brand deals
“Don't be afraid to do brand deals where you do get into brand names with tiny ownerships. The most important thing is that you align yourself with incredible founders and incredible companies in this new era, especially in this new era of AI, just get into som…”
Oct 25, 2024
Oct 25, 2024
Oct 25, 2024
Oct 25, 2024
Stebbings: Forcing 3x growth projections lowers seed valuation asks
“Smaller. Cause they're like, oh shit, the 25, I don't know if we'll be 75 when we're one million in ARR. And so, especially at seed, I'm seeing the 25 go to 15. Cause they're like, I could do 45, but really confidently predicting 80. It's quite hard.”
Oct 25, 2024 negative
Stebbings: Passing on Suno and ElevenLabs were my biggest mistakes
“So I look at like my biggest mistakes this year have been Suno, And 11 labs, and both of them I didn't do because they were small checks, probably like one percent each, and that didn't fit the model, and that was my lack of mental plasticity.”
Nov 1, 2024 positive
Stebbings: Frequent childhood relocation is top commonality among successful founders
“I've interviewed 800 of the best founders over the last decade, and the single biggest commonality in the most successful founders is a high frequency of moving in childhood. You're forced to assimilate with different environments, different cultures, differen…”
Nov 15, 2024
Nov 15, 2024
Nov 18, 2024
Stebbings: Working every weekend for a decade caused severe health issues
“I do think, like, I have heart palpitations, I have psoriasis, I'm aging as a 28 year old, because I've worked every weekend for 10 years, and I've given it my unwavering life, while everyone else has had holidays and time off.”
Nov 18, 2024
Nov 20, 2024 neutral
Nov 20, 2024 negative
Nov 20, 2024 negative
Dec 6, 2024 bullish
Stebbings: $50B tech acquisitions will happen as acquirers hit $3T valuations
“By the way, people are like, you've never seen a fifty billion dollar acquisition. Yes, actually you will do when companies are worth three trillion as a percent of market cap. It's absolutely aligned to what, you know, traditional acquisitions were.”
Dec 13, 2024
Dec 13, 2024 negative
Jan 6, 2025 positive
Jan 8, 2025
Jan 8, 2025 positive
Jan 10, 2025 neutral
Stebbings: Consumers won't pay extra for newer AI models in five years
“I don't, I tweeted this yesterday actually because of this, sorry but I don't think in the future we will pay more for access to newer models. I think that is just a stage of the development cycle that we're in. In five years time we won't pay more for a bette…”
Jan 20, 2025 positive
Jan 29, 2025 bullish
Feb 3, 2025
Feb 3, 2025 positive
Feb 14, 2025 negative
Feb 14, 2025 negative
Feb 14, 2025 neutral
Feb 14, 2025 positive
Feb 14, 2025 bearish
Stebbings: Infinite AI content supply will make discovery inherently harder
“I'm worried that AI will create an infinite supply of content. And what happens obviously if you, As an economist, which, you know, I'm not for sure but as a venture investor I proclaim to be one it reduces the cost reduces, like, price. Infinite supply will a…”
Feb 14, 2025 negative
Mar 3, 2025 neutral
Mar 5, 2025
Mar 7, 2025 positive
Mar 10, 2025 negative
Stebbings: Having associates conduct reference calls is a major VC mistake
“I think one of the biggest mistakes that firms make is when they get associates to just go and do the, Reference course. I mean, I'm nothing against associates, but there's so much in tonality, in the pause, in the facial expression.”
Mar 14, 2025 bearish
Mar 17, 2025 negative
Mar 17, 2025 neutral
Mar 19, 2025 bullish
Stebbings: Google is one of the most unappreciated AI opportunities
“Well, this is why actually I think Google is one of the most, like unappreciated companies right now. When you look at the distribution endpoints that they have to consumers and what they can do with AI, they are by far one of the most exciting opportunities.”
Mar 21, 2025 negative
Stebbings: Having a Family Prevents Founders From Operating at Peak Performance
“When you have the kids and the wife, suddenly, you are no longer the most important thing. That sleep schedule goes to shit. And your ability to inspire in that meeting is completely off. Your ability in fundraising, it's all, you're not performing at peak.”
Mar 26, 2025 negative
Stebbings: Lost seed deal to $8M on $100M uncapped offer
“I did three on 15. Handshake was the founder. It was pre-product, pre-revenue, pre-everything, but amazing founder. And he called me up and said, I would never walk out on a handshake. But I got offered eight on a hundred, and it's uncapped.”
Apr 10, 2025
Apr 10, 2025
Stebbings: Founders should not enforce minimum check sizes for valuable angels
“Never have a minimum check size for amazing angels. There's some who can only do five K, or, I mean, some are one K, and you can do that with angel or syndicates. Like, it's just as valuable, and often they'll give more because it means more to them.”
Apr 10, 2025 bullish
Apr 11, 2025 positive
Apr 14, 2025 negative
Stebbings: UBI destroys purpose and drives human addiction and vice
“I don't buy UBI, by the way. I think that is fundamentally lacking. You don't? No, humanity requires purpose. If you remove, if you add UBI, you remove purpose. And people say, oh, we're going to fish and we're going to paint. I promise you that is not how hum…”
Apr 14, 2025 bullish
Stebbings: Consumer brands succeed by filling the void left by traditional religion
“I say, actually, that the death of religion is the thesis for CPG and consumer brand investors today. And you're like, what? Thesis? Because we've shifted cult-like worshipping from God, Buddha, and these deus figures to High Rocks and CrossFit and Taylor Swif…”
Apr 14, 2025 neutral
Apr 17, 2025 bullish
Apr 18, 2025 bearish
Apr 24, 2025 negative
Stebbings: Passed on ElevenLabs at $25M valuation, missing a fund return
“11 labs at twenty five million. I could have had one percent of the company. And I was like, one percent. And like, no way. It was a twenty five million dollar fund. It's a three billion dollar company now. I would have been a fund return.”
Apr 24, 2025 positive
May 1, 2025 negative
May 2, 2025 negative
May 5, 2025 negative
May 5, 2025 neutral
Stebbings: Domain specialization helps VCs win deals, not pick founders
“I don't think domain specialization particularly helps you pick. I think generational defining founders are quite obvious respectfully. That said, I think to your point, they choose you because you're the smartest. So it doesn't help you pick. It helps you win”
May 8, 2025
May 9, 2025 positive
May 16, 2025 negative
Stebbings: Avoiding video podcasting on YouTube was a major strategic mistake
“A good example for me, say, would be I was very much a fan of not doing video. We don't do YouTube. No, we are constrained on audio because we do a lot of shows, but they're very, very good. People don't feel as comfortable on video. The constraint of channel …”
May 23, 2025
May 23, 2025
May 23, 2025 positive
May 23, 2025
May 29, 2025 negative
Stebbings: The general London population is 'relatively mediocre'
“The greatest founders that I know are motivated by the internal fire and being in London. I push myself every day to be better. Yeah, everyone around me is relatively mediocre in terms of London, generally speaking, generally group population wise. I didn't ne…”
Jun 2, 2025 positive
Jun 2, 2025 negative
Jun 6, 2025 positive
Jun 12, 2025 positive
Jun 12, 2025 negative
Stebbings: Hopin, BeReal, and Clubhouse failed to be 20VC's top returners
“With my first fund, after 18 months, I predicted my top five fund returners, and you had your hop-ins, you had your B-reels, you had your clubhouse, and none of the five outperformers ended up being the outperformers, and the five outperformers I always had in…”
Jun 23, 2025 negative
Harry Stebbings claims 95% of non-founding VC partners leave within 10 years
“They will not, like, 95% will not be there in 10 years. That's why most VCs are not rich, actually. It's because they're not there long enough for the carry to hit. That's why you go with people who founded the firm, because they're fucking stuck. They're neve…”
Jun 26, 2025
Jun 27, 2025
Stebbings: Top venture investors benefit from having prior interviewing experience
“I actually think that the best investors started life in some form of interviewing capacity because you have this similar dynamic where you have three to five minutes at the beginning of each show where you have to make the guests feel very comfortable.”
Jun 30, 2025 positive
Jul 10, 2025 negative
Jul 11, 2025 bullish
Jul 14, 2025 positive
Jul 17, 2025 bullish
Jul 17, 2025 bullish
Stebbings invested $12M in Lovable, citing consumer brand leadership
“Why did I write a twelve million dollar check into Lovable? I think very much in the same way that ChatGPT owns the consumer brand for that front end OS for the modern consumer, I think Lovable's reached escape velocity with the consumer brand in this space”
Jul 17, 2025 bullish
Jul 17, 2025 bullish
Stebbings: 20VC German AI startup grew from $200k to $1M in weeks
“We just did one in Germany peak when we did it. Two, 200 K when we did it is now at a million, like three weeks, but fucking nuts. The customer adoption that one of the fastest polls that I've seen in terms of consumer demand or customer demand,”
Jul 21, 2025
Stebbings: Building a $10B+ company requires working seven days a week
“You must work seven days a week if you want to build a ten billion dollar plus company, and the ability to put your phone on the side and not check an email does not exist anymore if you want to build a ten billion dollar plus company.”
Jul 24, 2025 positive
Jul 27, 2025 bearish
Jul 27, 2025
Jul 27, 2025
Aug 11, 2025 bearish
Stebbings: Series A is currently the worst venture stage to invest in
“I think Series A is the worst place to be investing today. Obviously we do Series A. Not promoting ourselves. It's a very truthful exposure. It's like, hey, the price inflection point is so high, often three to five X, and the company progression is often less…”
Aug 14, 2025 bullish
Aug 14, 2025 positive
Harry Stebbings: 20VC's $2M-$3M high-valuation 'Yolo' fund pool is up 7x
“Do you know, the funny thing is we have a like Yolo segment of our fund, which is like, yeah, which is a tiny pool of cash, whatever, like two million or three million, whatever. But it's basically, we have amazing access because of the shows and people will g…”
Aug 15, 2025 negative
Stebbings: European founders received $30M and $12M US term sheets within 72 hours
“But I had two companies that basically for six months had not been able to raise in Europe. And then in the U S they got a thirty million pound term sheet and a twelve million pound term sheet within 72 hours of landing.”
Aug 15, 2025 bearish
Aug 15, 2025 neutral
Aug 18, 2025
Aug 29, 2025
Sep 18, 2025 neutral
Stebbings: Decacorn CEOs spend aggressively on AI but switch easily
“The only interesting take I'll take is that I interview, honestly, three to four Dacacorn CEOs every week, and on this topic, two interesting elements, completely price insensitive as to how much they spend on Anthropic, and Claude Code in particular. I was th…”
Sep 18, 2025 negative
Sep 19, 2025 positive
Sep 19, 2025 positive
Sep 19, 2025 negative
Sep 25, 2025 neutral
Sep 26, 2025 negative
Oct 9, 2025 positive
Stebbings: Investors can identify best and worst investments within 60 days
“I also think that you can tell your best and your worst within the first 60 days. The messy middle, you don't know. There's a TBD, but the ones where you're like, shit, we regret that one. That, you tell pretty quickly, and same with the god, they're on it. Th…”
Oct 16, 2025
Stebbings: Early Venture Winners Rarely Predict Long-Term Enterprise Value
“When I look back on, like, fun one where there's, like, a meaningful timeline to actually look back on the six years now, the best performers, your linears of the world, were not obvious early, and the early out performers did not signify enterprise value in t…”
Oct 16, 2025 bullish
Oct 17, 2025 negative
Oct 20, 2025 bearish
Oct 20, 2025
Oct 20, 2025 positive
Oct 23, 2025 bullish
Stebbings: Productive capital will not leave AI for three years
“Like we will not have productive capital leave AI and data centers for more than three years. And so everyone that's like, oh, we're in an AI bubble, we're in an AI bubble and it's going to bust. I don't think so, because if we're in a bubble and you're antici…”
Oct 23, 2025 bullish
Stebbings: Top mega-fund partners will make over $1B in distributions
“Well, I think if you are one of the top one to three carry participants in one of the large mega platforms, be it Andreessen, be it Thrive, be it GC, I would argue that you will have more than that in distributions in the next few decades.”
Oct 23, 2025 positive
Stebbings: Early investment in Poolside founder's previous startup returned 50x
“I was actually one of the first investors. I don't know if you guys knew this. I invested in ISO, the founder of Poolside's business. Which pivoted into poolside. And so I got rolled in very luckily into like the first round, which is great. I'm very grateful …”
Oct 27, 2025 bearish
Stebbings: Defense tech is not a broad market category like SaaS
“I don't think defense is a category. And you're like, what? A category is enough that can support an ecosystem with its breadth and depth. I don't think defense is. I think there is your andrills and maybe two to three more in the U.S., and I think there's, yo…”
Oct 27, 2025 bearish
Oct 27, 2025 positive
Oct 31, 2025 negative
Nov 3, 2025 negative
Nov 10, 2025 negative
Nov 13, 2025 neutral
Stebbings: VC Winners Will Be Mega-Platforms or Specialized Boutiques
“To me, I think it's like a specialization in leadership that's kind of correlated to actually the winners and losers in venture in the next 10 years, and I think the winners are Walmart, which is your mega platforms, it's your Thrive, it's your Lightspeed, it'…”
Nov 13, 2025 positive
Nov 13, 2025 negative
Stebbings: SaaS Startup Needed 120 Meetings for One Term Sheet Despite 10x Growth
“We had a company that went from 400 K to three million Naira, classic enterprise SaaS business, bread and butter enterprise SaaS that would have had five term sheets from five good firms, 120 meetings, one term sheet and it was ten million round on a 40 post.”
Nov 17, 2025 positive
Nov 21, 2025 neutral
Altman: Seed VCs have a 15-year window before being replaced
“Yeah, we have to compete with them, we have to do better than them, there's not room for all of us, and Frankly, I kind of think, Harry, you were younger when you started, so you might have a little more time. I got, like, 15 years of this until I'm really goo…”
Nov 28, 2025 bullish
Stebbings: Athletes make great founders due to comfort with delayed gratification
“I love athletes, and I love investing in athletes, and the reason I do is because you are willing to sacrifice time and yourself for no immediate reward or gratification. It comes in the future, and you have to have this continuing belief that if you do do thi…”
Dec 1, 2025 bearish
Dec 8, 2025
Stebbings: I regret not providing a longer transition leaving my old fund
“When I left my old fund, you know, I was very quick in leaving and I really left no time for transition. I was quite thoughtless in my old partner. And I really regret that. I'm like, I should have given more time, been more thoughtful and caring. And with the…”
Jan 9, 2026 positive
Stebbings: Enterprise Implementation Fails Without Forward Deployed Engineers
“I honestly think the biggest lie in enterprise is that you're going to see implementation and adoption without FDs. Like you will need FDs and you will need implementation if you want to sell into the largest companies in the world, of course.”
Jan 9, 2026 positive
Jan 11, 2026
Jan 12, 2026 bearish
Jan 16, 2026 bearish
Stebbings: Tech leaders face unprecedented demonization by 2026 over AI job losses
“I think another prediction of mine for 2026 is I think we're going to see like the demonization of tech and tech leaders like never before, as you see the first real instantiation of job losses and job displacement in, in large parts of the economy, like in lo…”
Jan 16, 2026 bullish
Stebbings: Most knowledge workers will use 24/7 background AI inference by 2026
“I think one thing that we're going to see in 2026 that no one's talking about is 24 seven inference that everyone is going to have inference running all the time, not just on input into chat GPT, but consistently for the majority of people, especially in knowl…”
Jan 19, 2026 negative
Jan 22, 2026 bearish
Stebbings: Competing in Series A and B Rounds Is a Dummy's Game
“The dummies game, I think, right now, is playing the super competitive series A, B's in venture, where we're paying up super early for little signs of product market fit in intensely competitive markets, a hundred X ARR. I'd way rather have 15, 20% of a pitch …”
Jan 24, 2026 positive
Stebbings: Uses "What Would Sequoia's Pat Grady Do?" as Decision Framework
“Think of someone who you deeply respect and admire and you want their life. For me, it's Pat Grady at Sequoia. Three reasons. Great father, great investor, Great husband. And whenever I'm faced with a tough decision, I ask, what would Pat do in this case? And …”
Jan 24, 2026 positive
Stebbings: Move business contacts off email onto WhatsApp to build genuine rapport
“What people don't see is the 10 years of relationship building before that, but the most important lesson from that, actually, is I always want people off email. Get people off email. People want to work with people who they like”
Jan 24, 2026 neutral
Jan 24, 2026
Stebbings: Raised 20VC Capital via WhatsApp Between Gym Sets
“When we fundraise, we raise from very rich individuals, we raise from, you know, institutions, and I would, in between sets in the gym, walk around in my two-minute breaks, and I would message individuals, this was, and say, hey, I'm going out to raise the new…”
Jan 24, 2026
Jan 24, 2026 bullish
Jan 24, 2026 positive
Jan 24, 2026
Jan 24, 2026
Jan 24, 2026 positive
Jan 24, 2026
Stebbings: Improving an existing model by 10-20% yields successful businesses
“Very often you can just take something that works and make it 10 or 20% better. Oh, I love that cafe, but I've always wondered why they don't do really Instagrammable cakes, because the coffee is great. And the location is great. Why don't they do more? Making…”
Jan 24, 2026
Jan 24, 2026
Jan 24, 2026 positive
Jan 24, 2026 positive
Jan 24, 2026
Stebbings: Befriend a Target's Spouse to Influence Their Final Decision
“At the end of the day, a partner's statements about someone will very often impact their decision. So whenever I go to a dinner or a drinks party or whatever, the partner of the person that I want to influence will be my best friend, because the power of the c…”
Jan 24, 2026
Jan 24, 2026 positive
Stebbings: Hires Family and Friends to Bypass Work-Life Balance Trade-Offs
“My business partner always tells me very correctly, life is like a cooker in a kitchen. There's four hobs, you know, that you turn on. There's family, there's friends, there's work, and there's fitness, ok? Family, friends, work, and fitness. And the trouble i…”
Jan 24, 2026 negative
Jan 31, 2026 bearish
Harry Stebbings says multi-million dollar celebrity endorsement deals rarely work
“The big celebrity payments, they never work out well. I've been in so many companies where like, honestly, just like, five million bucks to like Ronaldo to do an Instagram post. I promise you, it does not work the way you think it will.”
Feb 2, 2026 negative
Feb 2, 2026 positive
Feb 2, 2026
Feb 7, 2026 negative
Feb 9, 2026 negative
Stebbings: Series A is currently the hardest stage for venture investing
“And I say that Series A is the hardest place to be investing right now. Because essentially you have a million in revenue, very little signs of product market fit, honestly, at a million in revenue. You're paying a hundred to 200 XAR and it's incredibly compet…”
Feb 9, 2026
Feb 16, 2026 bearish
Stebbings: 20VC will not invest in per-seat software pricing models
“If they sell per seat, we're not doing it. We need to replace jobs. Like labor displacement is what we're investing into. And that's the only way that we can actually return the amount of money that we need to now to make funds worth it.”
Feb 16, 2026 negative
Feb 16, 2026 neutral
Feb 16, 2026 negative
Feb 19, 2026 neutral
Stebbings: $8M-$20M ARR portfolio startups are stepping off the venture track
“I just see a realization in my portfolio now of companies that are in the eight to twenty million ARR range, not benefiting massively, but growing 80 to a hundred percent that are basically like, okay, we've raised our last venture dollars and we're going to h…”
Feb 19, 2026 positive
Feb 21, 2026 bearish
Feb 23, 2026
Feb 23, 2026 positive
Feb 26, 2026 bearish
Mar 7, 2026 negative
Mar 9, 2026 positive
Mar 16, 2026 bullish
Mar 26, 2026
Mar 30, 2026 negative
Stebbings: Passed on ElevenLabs seed round over 1% ownership
“My biggest regret or omission experience is one of your companies, actually, it's 11 Labs. We could have invested at the seed round, but we would have only got one percent mark, and naturally, as an emerging manager, I thought it was important to retain the hi…”
Apr 2, 2026 negative
Stebbings: Sequoia and top VCs announce misleading blended valuations
“The amount of Sequoia rounds where it's like, oh, you know, X raises money from square five billion. Trust me, Sequoia got in at one, but they just club it together and then announced the sum and then the latest valuation. And it's just very misleading.”
Apr 11, 2026
Apr 11, 2026 positive
Apr 11, 2026 negative
Stebbings: Managing institutional capital conflicts with full-time employer duties
“When you take institutional money, it's a great responsibility taking on someone else's money, and you have already made a promise to your employer that you will devote your best efforts and all of your energy to making them successful and the company successf…”
Apr 14, 2026
Apr 30, 2026 bearish
May 2, 2026 negative
May 2, 2026
May 2, 2026 negative
Stebbings: Staying at Salesforce for 12+ years signals mediocrity
“If you've been at Salesforce for 12, 1314 years, I automatically think you're not great. I'm like, you got stuck in your ways. You've been there for way too long. Seriously, you were happy just in this kind of melee of Mediocrity for 1213, 14 years.”
May 2, 2026 bearish
May 2, 2026 negative
May 2, 2026 positive
Stebbings: 90% of target CEOs respond to his LinkedIn messages
“One of our portfolio companies, the CRO, comes in every month, and gives me, like, the top 10 targets, and I just go with them to the CEOs on LinkedIn. I have a blue check mark and lots of followers on LinkedIn. Challenge shit on LinkedIn. Nine out of 10 respo…”
May 4, 2026 positive
May 9, 2026 negative
May 9, 2026
May 9, 2026
Harry Stebbings: Investors must diversify broadly to identify elite founders to concentrate in
“The biggest lesson I have in 10 years of investing is you have to diversify to concentrate, and it, actually, what I mean by, I should have invested in everything, and I should have done, to find The Alan Changs, the Adam Ferogis, the Cliff Weitzmans. You have…”
May 9, 2026 negative
Stebbings: Early hires calling themselves 'founding' advisors is a major red flag
“Like, for me, I'm like, I hate the people that are like founding GTM advisor, and it's like, no, no, no. You're just a GTM hire that was one of the first. You don't look like a founding, this like, everything needs to be a founding role. Fuck off.”
May 9, 2026
Stebbings: Investing in every met founder would yield 17x greater success
“If I'd invest in every founder that I'd met, every founder that I've met, I'd be 17 X more successful. One seven X more successful. I would have had two and a half percent of deal. I would have had two percent of 11 Labs. I'd have a seed check in Flettersport,…”
May 9, 2026
Stebbings: Interview red flags only worsen after hiring
“Also, when you get spidey senses in the interview process, listen. Like, it will only get worse post-hire. What I mean by that is when someone, they just get the feeling that, you know, they really actually want to be an investor, not in finance. Trust me, whe…”
May 9, 2026 negative
May 11, 2026
May 16, 2026 positive
May 16, 2026 negative
May 16, 2026
May 16, 2026 bearish
May 18, 2026 negative
May 18, 2026 negative
May 28, 2026 neutral
May 30, 2026
Jun 13, 2026 negative
Stebbings: VCs use elite founder credentials as a crutch amid AI uncertainty
“Fundamentally, there is intense uncertainty around what Anthropic and OpenAI will do and who they will kill at the application layer. And so in a world where we desperately seek certainty, we look for validators, and the validators of someone being a math Olym…”
Jun 20, 2026 bullish
Jun 20, 2026 negative
Jun 20, 2026 positive
Stebbings: Richer VCs perform better by focusing purely on upside
“I think that richer investors make better investors, and you're like, Sequoia are focused on upside maximization. How big could this be? They are not fearful of LPs coming back for their next fund. They're not fearful of deployment speed compressing, so, you k…”
Jun 20, 2026 negative
Stebbings: Passing on Great Companies Over Market Size Is My Biggest Mistake
“So my biggest mistake is when I focused on market at all. All of my biggest mistakes in investing have been actually not really like, you know, losing money. It's been turning down great companies, but because I thought that I was smarter than the market.”
Jun 20, 2026 negative
Jul 2, 2026 bearish
Jul 6, 2026
Stebbings: 20VC lost two deals to competitors bidding 3x higher valuations
“We've lost two deals in the last year. And listen, we got outbid, I'm, I don't know if we would have won if we'd paid the same price, I hate people that say that. Yeah. But by like two or three X, we bid one 50, and another we got outbid by 300, another we out…”
Jul 6, 2026 negative
Jul 6, 2026 negative
Stebbings: Content creation requires extreme scale or ultra-lo-fi authenticity
“I also think very much like venture, you have to be either really big or really small in content. You have to be very natural, kind of teenager, putting their phone up on the side and hitting record, or you are Logan Paul, or Mr. Beast, or like us of Vantures,…”
Jul 6, 2026 negative
Jul 6, 2026
Jul 6, 2026 positive
Jul 6, 2026 neutral
Jul 6, 2026
Jul 6, 2026 bullish
Jul 6, 2026 negative
Stebbings: I passed on Suno's seed round over 1% ownership target
“I turned down sooner when David Frankl at Founder Collective introduced me at The Seed. You know what the lesson was there? Really interesting. I hope Mikey's okay with me saying this. I'm sure he is. It was a 250 K check or a 200 K check. And so the ownership…”
Jul 11, 2026 positive
Jul 13, 2026 positive
Stebbings: Wealthier founders and investors make better decisions
“I have a theory, and the reason for this is I think richer investors and richer founders make better decisions. You're not operating from fear. You're not operating from losing homes, losing school fees, losing core pillars of life. I actually make much more r…”
Jul 16, 2026 negative
Jul 16, 2026 bullish
Jul 20, 2026 negative
Jul 20, 2026 bullish
Jul 23, 2026 neutral
Jul 23, 2026 neutral
Jul 25, 2026 bearish
Jul 25, 2026 negative
Jul 27, 2026 negative
Rejecting 1% allocations in Deel and ElevenLabs cost Stebbings massive returns
“There have been several companies where we've had, like, one percent offered to us, Deal, 11 Labs, Starcloud, where we were like, one percent, we can't be doing that, and now I look back and all of them would have returned huge amounts of money.”
Jul 27, 2026 negative
Traditional 'triple-triple-double-double' startup growth is no longer attractive for VC
“I turned down a company the other day, Because they were going from, like, one and a half to five to 15, and there's an opportunity cost of capital to say that's very real, and the growth expectations are just very different. In other words, triple, triple, do…”
Aug 2, 2026 neutral
Aug 7, 2026 neutral
Stebbings: Wix is trading at 1x revenue with a $2.1B valuation
“The market can stay irrational longer than you can stay solvent, and when I look at, like, a Wix today, trading at 2.1 billion on 2.1 billion of revenue, it's a great example where, like, there's obviously rationality at play, but it doesn't matter.”
Aug 7, 2026 positive
Stebbings: VCs Should Take 50% Secondary Discounts Over Waiting Years for IPOs
“I just think we don't think about the velocity of cash enough, and what I mean by that is like, you know, yes, there might be another double, but if I have to wait five years, and then the IPO, and then an 18 month lockup, Jesus, give me 50% of that now, and I…”
Aug 7, 2026 bullish
Aug 7, 2026 bearish
Stebbings: Scaling From $1.5M to $15M ARR Is No Longer VC-Fundable
“I turned down a company the other day that went from one and a half, and they were gonna go to five, and then they were gonna go from five to 15, and it's just not enough anymore. It's just not interesting. I'm sorry for venture. We have an opportunity cost of…”
Aug 7, 2026 bullish
Aug 14, 2026 negative
Aug 14, 2026 positive
Aug 14, 2026 negative
Stebbings: A 6-week AI bootcamp is more valuable than university
“Come to our school, and for six weeks, we will teach you how to get jacked up
On every system, process, model, for six weeks, nine to five, this is your job, and you pay 10,000 bucks.
I would say that's more valuable than university, say, for teenagers.”
Aug 17, 2026 positive
Stebbings: Revolut's Nik Storonsky Is the Best Founder Out of 1,000
“Nick Staronsky from Revolut. I've interviewed a thousand founders. He's the single best founder I've ever interviewed, and it's because he runs 26 product experiments at once. He gives them two million dollars, tells them to run for a year. Every single week h…”
Aug 22, 2026 bullish
Stebbings: Enterprise Specialized Data Is a $200 Billion Market Opportunity
“And part of the training for those models will require additional surplus data, and then you'll see the likes of McCaw go from purely selling to frontier models to selling to enterprises and even mid-market who need specialized data that they might not have, a…”
Aug 27, 2026 bearish
Aug 27, 2026 positive
Aug 29, 2026 bullish
Aug 29, 2026 neutral
Aug 31, 2026
Katz: ClickHouse extended its financing despite having $1B on its balance sheet
“And so we did a financing earlier this year, and then we extended it and brought in some strategic investors like yourself and David Sachs and Michael Dell and JP Morgan. We didn't need the capital. We had a billion dollars on the balance sheet.”
Sep 5, 2026 neutral
Sep 5, 2026 neutral
Sep 5, 2026 negative
Sep 5, 2026 neutral
Sep 5, 2026 neutral
Sep 7, 2026 positive
Sep 7, 2026 neutral