Harry Stebbings

Harry Stebbings

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20VC; early‑stage founder journeys, venture dynamics, tactical founder advice.

Tiger Global Poised for Higher Returns via Databricks and OpenAI
SocialNov 11, 2025

Tiger Global Poised for Higher Returns via Databricks and OpenAI

Why Everyone is Wrong About Tiger Global Returns:  "I think Tiger's gonna end up much better than anyone thought. They got a big stake in Databricks. They were early into OpenAI and Scale. They will benefit from liquidation preferences and preferred stock."...

By Harry Stebbings
Mega Funds Prioritize Capital Velocity Over Early-Stage Deals
SocialNov 10, 2025

Mega Funds Prioritize Capital Velocity Over Early-Stage Deals

Why the Mega Funds are Focused on Capital Velocity: "The North Star for @generalcatalyst @lightspeedvp is investment velocity. Talk to the principles and Jr Partners at these firms.... It does not matter what @ravi_lsvp @htaneja are saying; when you are writing $BN...

By Harry Stebbings
Peter Fenton Excels by Trusting Founder Conviction over Stages
SocialNov 10, 2025

Peter Fenton Excels by Trusting Founder Conviction over Stages

What Makes @peterfenton So Good? " Peter does an amazing job following his founder conviction. He doesn't think about stages. When he finds a @howietl @btaylor that's what guides him." @EverettRandle What have been your biggest lessons from working with Peter @howietl...

By Harry Stebbings
Align Incentives: Invest With Partners to Test Conviction
SocialNov 10, 2025

Align Incentives: Invest With Partners to Test Conviction

The Biggest Investing Lesson from Peter Thiel: "Peter creates incentive structures to test the conviction level of partners. For example, you can personally invest alongside the fund in a deal you are leading. If you do not, he will ask, do...

By Harry Stebbings
Exit Tax Threatens $200M UK Investment and Jobs
SocialNov 10, 2025

Exit Tax Threatens $200M UK Investment and Jobs

I have invested $200M into the UK in the last five years. If @RachelReevesMP implements “Exit Tax” all that funding will go overnight. That is countless jobs, companies and people who will lose out. Rachel, you have managed to steal our...

By Harry Stebbings
AI Customer Support Flooded with Billion‑Dollar Funding
SocialNov 9, 2025

AI Customer Support Flooded with Billion‑Dollar Funding

One market I cannot figure out in a world of AI is customer support. You have: Sierra Decagon GigaML Parloa Forethought Kore Cresta All of these have raised over $100M. and then oldies like Intercom Zendesk Help me out, how does this market shake out?

By Harry Stebbings
Send Investor Updates: Leverage Trust, Drive Growth
SocialNov 8, 2025

Send Investor Updates: Leverage Trust, Drive Growth

Founders, for the love of God; send investor updates. 1. Leverage them for help with customer intros, hires and fundraises. 2. Use them to create excitement and conversation about you in market. 3. Because these people have trusted you and...

By Harry Stebbings
Hummingbird's First Biotech Deal Nets $800M Stake
SocialNov 7, 2025

Hummingbird's First Biotech Deal Nets $800M Stake

Let me just get this straight: Hummingbird owned 16% of BillionToOne at IPO. That is an $800M stake. This was their first ever biotech deal. These guys just play another game!!

By Harry Stebbings
Benchmark’s Portfolio Outshines All Other Funds
SocialNov 6, 2025

Benchmark’s Portfolio Outshines All Other Funds

Of every fund of this vintage, I would rather have Benchmark’s portfolio than any other: Sierra ($10BN) Mercor ($10BN) Firework ($4BN) Legora ($2BN) Langchain ($1.3BN) Manus (one of most insane teams in AI) HeyGen ($80M ARR) Today it gets...

By Harry Stebbings
Navan's IPO: Who Wins? & Harvey Raises $150M at $8BN Price & Why Google Is a Buy, Amazon Is a...
VideoNov 6, 2025

Navan's IPO: Who Wins? & Harvey Raises $150M at $8BN Price & Why Google Is a Buy, Amazon Is a...

The panel dissected Navan’s recent IPO, noting the company priced near the top of its range at a $5 billion valuation only to trade down to roughly $4.8‑4.9 billion, challenging Bill Gurley’s notion that IPO allocations are always free money. They explained...

By Harry Stebbings
Scaling Laws, Synthetic Data, and AI Myths Debunked
SocialNov 3, 2025

Scaling Laws, Synthetic Data, and AI Myths Debunked

Joelle built the AI lab at Meta She worked and learnt from Zuck She is one of the leading minds in AI What everyone thinks they know about AI but get wrong 👇 - Why Scaling Laws Will Continue - Why You Can’t Buy Success...

By Harry Stebbings
Cohere's Chief Scientist, Joelle Pineau: Why Scaling Laws Will Continue & Future of Synthetic Data
VideoNov 3, 2025

Cohere's Chief Scientist, Joelle Pineau: Why Scaling Laws Will Continue & Future of Synthetic Data

Cohere’s chief scientist Joelle Pineau, a former Meta researcher, discussed the durability of scaling laws, the current limits of reinforcement learning (RL) and the shift toward enterprise‑focused, on‑premise AI models. She emphasized that while compute and data yield roughly linear...

By Harry Stebbings
Act Fast on Good VC Offers—Don’t Delay
SocialNov 3, 2025

Act Fast on Good VC Offers—Don’t Delay

Founders when you meet a VC and they give you a good offer. By running a “process” you are optimising for one of two things: 1. Price 2. The best partner If you have both, just do the deal now. Delay...

By Harry Stebbings
20VC Newsletter - 2nd November 2025
BlogNov 2, 2025

20VC Newsletter - 2nd November 2025

The newsletter recaps three recent 20VC episodes, highlighting AI’s shift from dollars to gigawatts, the commoditization of compute, and the rapid scaling of AI startups to $100 M revenue, while questioning high AI talent pay and the relevance of gross margins....

By Harry Stebbings
Why I Picked Angel Investing Over MBAs
VideoNov 2, 2025

Why I Picked Angel Investing Over MBAs

A Princeton graduate who had long coveted a Stanford MBA decided to skip the program, treating the $120,000 tuition as a sunk cost and instead investing that money in early‑stage startups alongside angel investor Mike Maples. He framed the decision...

By Harry Stebbings
US VCs Dominate European Series A Funding
SocialNov 1, 2025

US VCs Dominate European Series A Funding

European VCs are getting their lunch eaten at Series A by the best in the US: 1. ElevenLabs, led by a16z @kirbyman01 2. Synthesia, led by FirstMark @mattturck 3. Legora, led by Benchmark @sarahtavel @chetanp 4. Fyxer, led by Madrona...

By Harry Stebbings
100M Views… Zero Impact?
VideoOct 31, 2025

100M Views… Zero Impact?

The speaker notes that viral video clips—even those surpassing 100 million views—often generate negligible traffic to the underlying long‑form podcast, with download numbers remaining flat. He attributes this to platform operators who, backed by well‑funded data teams, promote engagement metrics that...

By Harry Stebbings
Tech Weekly: Fund Raises, OpenAI Shakeup, VC Insights
SocialOct 30, 2025

Tech Weekly: Fund Raises, OpenAI Shakeup, VC Insights

The only podcast you have to listen to every week. No politics. Just tech. - a16z Raises $10BN in New Funds - Mercor Raises $350M at $10BN - OpenAI Restructuring: Who Wins & Who Loses - Why IRR is a BS Metric - 3 Ways to...

By Harry Stebbings
European Investment Council Ranks #4 in Sifted’s Top 50
SocialOct 30, 2025

European Investment Council Ranks #4 in Sifted’s Top 50

In another magnificent piece of work by Sifted 🤣 I would like to congratulate… The European Investment Council On being a top 50 performing investor. They are #4 according to Sifted. You can’t make this s*** up. 🤣 Too good Sifted....

By Harry Stebbings
Hire AI Generalists: Young Talent Beats Experience
SocialOct 29, 2025

Hire AI Generalists: Young Talent Beats Experience

" Companies underestimate 23 and 24 year-olds. The new playbook for these AI startups is actually gonna be much more about hire the AI generalist, this 23, 24, 25-year-old who's really native in AI." @DavidCahn6 Do you agree and how do...

By Harry Stebbings
Leverage Competitors' AGMs to Meet LPs Fast
SocialOct 29, 2025

Leverage Competitors' AGMs to Meet LPs Fast

The single best way to meet a lot of high quality LPs fast. Find out when your competitors AGMs are. Reach out to their LPs knowing they will be in town on those dates. They always want to fill their...

By Harry Stebbings
Margins Reveal Product Depth on Foundation AI Models
SocialOct 28, 2025

Margins Reveal Product Depth on Foundation AI Models

" I do think margins matter in a world of AI.  They're a directional indicator of how much product you've built on top of the foundation models." @DavidCahn6 Do you agree and how do you think about margin in the...

By Harry Stebbings
Founders Drive Success; VCs Can only Assist
SocialOct 28, 2025

Founders Drive Success; VCs Can only Assist

"The lesson that punches you in the stomach in venture is  you can't make companies succeed as a venture capitalist. The company succeeds because of the founder and maybe you helped a little bit." Love to hear your thoughts on this...

By Harry Stebbings
Why AI Salaries Are Outrageous
VideoOct 28, 2025

Why AI Salaries Are Outrageous

Compensation for top AI talent has ballooned to eye-popping levels, with recent graduates from elite schools reportedly receiving $50–$100 million packages and marquee names being offered deals worth up to $1 billion. That surge reflects a frenzy in tech and...

By Harry Stebbings
Best Deals Often Come From Solo Term Sheets
SocialOct 27, 2025

Best Deals Often Come From Solo Term Sheets

"Most of the great investments I have made I was the only term sheet. This idea that the best companies are always super hot rounds is wrong." @DavidCahn6 Have your best investments always been competitive @chadbyers @infoarbitrage @honam @Alfred_Lin? https://t.co/MWp77TBZzR

By Harry Stebbings
Investors Chase Companies Hitting $0‑$100M Fast
SocialOct 27, 2025

Investors Chase Companies Hitting $0‑$100M Fast

"The best companies are going from $0-$100M in revenue very very quickly. As an investor, you have to believe that this company is going to be in the $0-$100M club". @DavidCahn6 Love to hear your thoughts on the required growth...

By Harry Stebbings
From $1M ARR to $1M Weekly Revenue
SocialOct 27, 2025

From $1M ARR to $1M Weekly Revenue

When 20VC led the Series A for Fyxer they were at $1M ARR. Today, they are adding $1M a week. 🚀 https://t.co/qvjg8Ke7uw

By Harry Stebbings
AI Winners, Margins, and Defence: Who Thrives?
SocialOct 27, 2025

AI Winners, Margins, and Defence: Who Thrives?

Our last episode with David Cahn was one of the most downloaded of last year. This episode today is even better. - The Winners & Losers in AI - The $0-$100M Club: Is Triple, triple, double, double dead? - The Future of Defence: Who...

By Harry Stebbings
Share LPs Across Non‑competing Funds to Accelerate Fundraising
SocialOct 27, 2025

Share LPs Across Non‑competing Funds to Accelerate Fundraising

The secret to LP intros that no one tells you. Make friends in alternate, non competitive categories (growth, secondaries etc etc). Share LPs. Discovery is the hardest thing in fundraising. Non-competitive managers sharing LPs is needle moving.

By Harry Stebbings
20VC Newsletter - 26th October 2025
BlogOct 26, 2025

20VC Newsletter - 26th October 2025

20VC’s latest newsletter synthesizes three interviews with practical takeaways for founders and investors: Deel CEO Alex Bouaziz laid out a repeatable M&A playbook that rebuilds frontends in months and full backends to hit product scale in about nine months (vs....

By Harry Stebbings
Scaling $1M‑$50M: Execution Beats Early Milestones
SocialOct 25, 2025

Scaling $1M‑$50M: Execution Beats Early Milestones

I do not care how long it takes for a company to get to $1M in revenue. But I do care desperately, how long it takes for a company to get from $1M-$50M in revenue. The road to PMF is...

By Harry Stebbings
Most Common Growth Mistake (And How to Avoid It)
VideoOct 25, 2025

Most Common Growth Mistake (And How to Avoid It)

The video warns that the most common growth mistake is reflexively copying competitors’ tactics without grounding decisions in customer context or data. The speaker recounts a Pinterest case where teams replicated Facebook’s seven-part onboarding and product flow, spent weeks implementing...

By Harry Stebbings
Tiny Check, Massive Return: Don't Underestimate Winners
SocialOct 22, 2025

Tiny Check, Massive Return: Don't Underestimate Winners

My single best investment from 20VC Fund I broke advice everyone gave me. Don’t write small checks. If it is less than 1% of the fund, it won’t move the needle. Wrong. I wrote a $50K check. Today it is...

By Harry Stebbings
Deel Acquires: Replace Core Assets, Rebuild Adjacent
SocialOct 21, 2025

Deel Acquires: Replace Core Assets, Rebuild Adjacent

"At Deel, we do two types of acquisitions. 1.  Buy an asset in our core market. Buy the team, revenue, bring them in-house, rip and replace their infrastructure with ours pretty fast. 2.  Buy smaller companies that are in adjacent...

By Harry Stebbings
Project Europe Delivers Rapid Product-Market Fit, Secures Major Wins
SocialOct 21, 2025

Project Europe Delivers Rapid Product-Market Fit, Secures Major Wins

Project Europe has product market fit so much faster and so much stronger than even we hoped. In the first 6 months: - 10 cracked teams invested in So what… of those 10: - 1 acquired by category leader - 1...

By Harry Stebbings
Own Your Software: Essential for Scaling Success
SocialOct 20, 2025

Own Your Software: Essential for Scaling Success

"A lot of SaaS is not tailored enough to the needs of the company. Owning most of the software makes a significant difference in what you can do. It is the dumbest thing to do when you are small. It...

By Harry Stebbings
Alfred Lin: Deep Business Insight Makes Board Exceptional
SocialOct 20, 2025

Alfred Lin: Deep Business Insight Makes Board Exceptional

"I would have most liked to have @Alfred_Lin on my board. He is one of the best investors in the world. He understands the business he invests in a lot more deeply than other board members." @Bouazizalex What have been...

By Harry Stebbings
Everything You Need To Know About Venture
VideoOct 20, 2025

Everything You Need To Know About Venture

Harry Stebbings recounts founding his venture firm from a London bedroom with no contacts or capital and growing it into an $850 million manager that has backed $12 billion in companies, including four valued at $10 billion. He frames fundraising...

By Harry Stebbings
Deel’s $300M Raise Reveals Aggressive Acquisition Strategy
SocialOct 20, 2025

Deel’s $300M Raise Reveals Aggressive Acquisition Strategy

I fricking hate podcasts where the guest does a podcast tour to promote something. @Bouazizalex just raised $300M+ at a $17BN+ valuation. He did one podcast to discuss the round and the crazy last 12 months. 20VC. - Raising $300M from Ribbit, a16z and...

By Harry Stebbings
Deel CEO, Alex Bouaziz on Raising $300M+ at a $17BN Valuation
VideoOct 20, 2025

Deel CEO, Alex Bouaziz on Raising $300M+ at a $17BN Valuation

Deel CEO Alex Bouaziz said the company has raised just over $300 million at a valuation above $17 billion in a round co-led by Ribbit Capital, Andreessen Horowitz and Coatue. He highlighted that Deel has been profitable for three years,...

By Harry Stebbings
Angel Fundraise Details Reveal Top 1% Founders
SocialOct 19, 2025

Angel Fundraise Details Reveal Top 1% Founders

You can tell a top 1% founder purely from how they structure the angel component of a fundraise. The blurb they suggest. The forwardable email they send for each. The specific angels they want in. All says so much about their...

By Harry Stebbings
Speed Is a Feature of the Best
SocialOct 19, 2025

Speed Is a Feature of the Best

Just sent a deal to a dear friend and mentor who is one of the greatest of our time. Sent at 8:12AM PST and response provided to me and founder by 8:18AM. Speed is a feature of the best.

By Harry Stebbings
20VC Newsletter - 19th October 2025
BlogOct 19, 2025

20VC Newsletter - 19th October 2025

The 20VC newsletter (Oct. 19, 2025) distills three podcast episodes featuring Atlassian CEO Mike Cannon‑Brookes, investors Rory O’Driscoll, Jason Lemkin and Roger Ehrenberg, and Warp CEO Zach Lloyd, highlighting how AI will expand software development, reshape pricing models, and leave...

By Harry Stebbings
Deel Secures $300M Funding, Valued Over $17B
SocialOct 16, 2025

Deel Secures $300M Funding, Valued Over $17B

Today @Bouazizalex announced that @deel have raised $300M at a $17BN+ valuation. He only did one podcast to announce the round and discuss the last 12 months. 20VC… coming on Monday 👇 https://t.co/n4ezdUmA5A

By Harry Stebbings
Tech Deals Surge: Meta, Goldman, SoftBank Drive 2025 Venture Landscape
SocialOct 16, 2025

Tech Deals Surge: Meta, Goldman, SoftBank Drive 2025 Venture Landscape

The only podcast you have to listen to every week. No politics. Just tech. - Thinking Machines Co-Founder Joins Meta for $3.5BN - Goldman Sachs Acquires Industry Ventures for $665M - Softbank Borrows $5BN Against ARM Holding to Invest More Into OpenAI. Spotify 👉 https://t.co/FMWC2UfrVG Youtube...

By Harry Stebbings
Y Combinator and A16z Dominate VC Under Stellar Leadership
SocialOct 16, 2025

Y Combinator and A16z Dominate VC Under Stellar Leadership

Two brands in VC that are crushing right now more than any other: 1. @ycombinator: Under @garrytan leadership. Another level achieved. 👏 @t_blom is one of the greatest early stage investors right now. 2. @a16z: @martin_casado is a true OG....

By Harry Stebbings
Product Fit and Partnership: Keys to Seed Success
SocialOct 15, 2025

Product Fit and Partnership: Keys to Seed Success

Two reasons why 99% of seed stage companies don’t make it to Series A: 1. They don’t build something people want. 2. Co-Founder breakup. Avoid these two and you are the 1%.

By Harry Stebbings
AI Takes 20 of Top 30 Secondary Spots
SocialOct 15, 2025

AI Takes 20 of Top 30 Secondary Spots

Just seen @SetterVC's latest report on the most in-demand secondaries for private companies in Q3: Top 3 Risers in the Top 30: 1. @canva up 8 places to #12 2. @CrusoeAI up 7 places to #11 3. @AnthropicAI up 2 places to #1 and...

By Harry Stebbings
Europe’s Top Founders Champion Browsers for AI Agents
SocialOct 14, 2025

Europe’s Top Founders Champion Browsers for AI Agents

Europe has some of the best young founders in the world. They are hungrier, they are more ambitious and they are more talented than ever. Charles is one of the best of the best. LFG Europe 🚀

By Harry Stebbings