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harry stebbings

T3 · host / generalist

Founder of 20VC (The Twenty Minute VC), one of the most popular venture-capital podcasts, and its associated fund.

33 calls·22 names·61% bull·last heard 27 days ago·20VC
track record

no scored calls yet — needs a stated position or a categorical verdict, with a matured window vs SPY

top calls

highest conviction · one per company
1sthigh conviction
$LOVABLELovableposition

Harry Stebbings: Portfolio company Lovable hit $13.5B valuation at $600-700M ARR — unprecedented growth trajectory

Lovable's explosive growth (600-700M ARR, $13.5B valuation) exemplifies the new AI-era company velocity where outcomes and growth rates are an order of magnitude larger than historical norms.

20VC2026-08episode →
2ndhigh conviction
$MERCORMercorposition

Harry Stebbings reveals Mercor investment at $2-3B, missed $20B round, now sees $200-300B path

Stebbings invested early in Mercor, passed on a later round at $20B valuation thinking 5x upside insufficient, but now believes data requirements for AI could drive a 100x+ outcome to $200-300B.

20VC2026-08episode →
3rdhigh conviction
$PEAKPeakposition

20VC invests in Peak for answer engine optimization

Peak builds tooling for answer engine optimization (AEO), positioning for a shift where AI agents become the primary discovery layer for software products.

20VC2026-08episode →

most discussed · click a bar to filter

  • $NBIS
  • $MERCOR
  • $RAMP
  • $LOVABLE
  • $NOW

recurring themes

  • SaaS Business Models1
  • IPO Market1
  • Venture Capital1
33 total
$RAMP
Ramp
LOWharry stebbings·20VC·2 months ago·The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Ramp's $500M raise at $40B exemplifies low-dilution mega-rounds
Stebbings cited Ramp's roughly $500 million raise at a $40 billion price as an example of large rounds with limited founder dilution and described continuous funding as attractive to founders.
"Ramp raising your like 500 million at a 40 billion price and actually kind of seemingly no kind of 50 million rounds at a billion dollar price."
54:02
$DEEPSEEK
DeepSeek
LOWharry stebbings·20VC·last month·Canva Slashes Growth | Demis Hassabis & Jeff Dean: Talent Exodus at Google | Musk's $55B Terrafab
DeepSeek raising at $74B valuation: Chinese AI model distillation of US models raises competitive concerns
DeepSeek's reported $74B raise for distilling US models highlights geopolitical tension in AI — Bytedance restricting distillation suggests IP protection becoming strategic.
"Deepseek raising an 8 billion at reported 74 billion. Um, Bite Dance Band's distillation of US models. Um, which I thought was interesting."
76:59
$LOVABLE
Lovable
HIGHharry stebbings·20VC·27 days ago·Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive· position
Harry Stebbings: Portfolio company Lovable hit $13.5B valuation at $600-700M ARR — unprecedented growth trajectory
Lovable's explosive growth (600-700M ARR, $13.5B valuation) exemplifies the new AI-era company velocity where outcomes and growth rates are an order of magnitude larger than historical norms.
"we're an investor also in a lovable of the world and suddenly it's a 13.5 billion business at 600700 million of [__] dude the the trajectory of company growth is just unparalleled"
56:30
$MERCOR
Mercor
HIGHharry stebbings·20VC·27 days ago·Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive· position
Harry Stebbings reveals Mercor investment at $2-3B, missed $20B round, now sees $200-300B path
Stebbings invested early in Mercor, passed on a later round at $20B valuation thinking 5x upside insufficient, but now believes data requirements for AI could drive a 100x+ outcome to $200-300B.
"I think we did it at like two or three billion. My my memory should be better, but I'm older than you. Um, and I didn't do the latest round at, you know, whatever 20 billion becau…"
11:15
$LINEAR
Linear
MEDharry stebbings·20VC·27 days ago·Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive· position
Harry Stebbings: Investor in Linear, notes both Linear and Atlassian crushing — market expanding not zero-sum
Stebbings is an investor in Linear; observes that both Linear and Atlassian are growing simultaneously, proving the project management market is far larger than zero-sum thinking suggests.
"I'm an investor in linear. Linear are absolutely crushing though. And they what's interesting is actually, and it's a really interesting one, is Atassian are crushing and so are l…"
81:20
$POOLSIDE
Poolside
MEDharry stebbings·20VC·29 days ago·NVIDIA Buys Poolside, Invests in Mercor & Perplexity | OpenAI Confirms IPO· position
Poolside acquired by Nvidia for $6B+$1B at $12B pre after failing to raise $2B for compute
Poolside hit the capital intensity wall for frontier models but still delivered a 15x return to seed investors; illustrates that in hypergrowth AI markets, even 'failed' standalone bets can yield compelling acquisitions because acquirers like Nvidia have unique compute access.
"they couldn't raise the 2 billion to buy 40,000 GPUs... they had no choice but to fail up for 6 billion plus topping off a billion to 12 billion"
0:57
$FRACTILE
Fractile
LOWharry stebbings·20VC·29 days ago·NVIDIA Buys Poolside, Invests in Mercor & Perplexity | OpenAI Confirms IPO
Fractile raising at $6.5B after Etched at $20B signals AI chip startup frenzy
New AI accelerator startups (Fractile, Etched) commanding multi-billion valuations pre-revenue reflects unbounded founder creativity and capital availability; outcome uncertain but 'now is the moment' for rule-rewriting attempts.
"Fractile reportedly raising new round at 6.5 billion recently following Etch round at 20 billion which we discussed last week"
72:42
$MERCOR
Mercor
MEDharry stebbings·20VC·29 days ago·NVIDIA Buys Poolside, Invests in Mercor & Perplexity | OpenAI Confirms IPO· position
Nvidia joins General Catalyst-led $20B round for Mercor at $2.5B ARR
Mercor has scaled to $2.5B ARR in data labeling/training services; Nvidia's participation may be strategic (access to training data flows) or simply deploying ecosystem budget, but the business commands AI multiples despite lower gross margins.
"Mercor's new funding round... crossing out two 2.5 billion AR... doing a new round led by General Catalyst at 20 billion. And then there's rumors... that Nvidia is joining that ro…"
13:18
$SOLVE-INTELLIGENCE
Solve Intelligence
MEDharry stebbings·20VC·last month·Julien Bek on Lessons from Don Valentine, Doug Leone & Alfred Lin | What Sequoia Sees in Founders· position
Solve Intelligence targets patent law vertical; Harvey and Legora founders invested
Legal AI will unbundle by practice area; Solve's focus on IP/patent law creates a defensible niche distinct from Harvey's horizontal approach, validated by competitor founders investing.
"We're in a business called solve intelligence. It's IP law very specific for patent lawyers and the IP market that is so different to a lot of what Harvey and Legora do to the ext…"
77:58
$PEAK
Peak
HIGHharry stebbings·20VC·last month·How to Build a $100M Growth Engine: Lessons from Wispr Flow & Superhuman | Matt Swulinski· position
20VC invests in Peak for answer engine optimization
Peak builds tooling for answer engine optimization (AEO), positioning for a shift where AI agents become the primary discovery layer for software products.
"We invest in peak which essentially optimizes this."
46:25
8
SaaS Business Modelsheadwind
Any liquidity for pre-AI SaaS companies is top-decile performance; transformation is mandatory
Pre-AI SaaS companies growing at single digits with no AI story are 'zombie' assets; the Intercom/Finn outcome proves that burning the boats to adopt outcome-based AI pricing is the only path to premium exits.
7
IPO Marketrisk
Gamma squeezes and forced buying distort price discovery in low-float IPOs like SpaceX
With only 4% float trading, options-driven gamma squeezes and index inclusion forced buying can inflate prices far above fundamental value until lockup expiry; shorting is prohibitively expensive due to high option implied volatility.
7
Venture Capitaltailwind
Fundraising velocity compressed: one great month now suffices for markup rounds
Companies now raise at 2x valuations within 4 weeks (e.g., unnamed company 10B to 21B in a month) on a single strong month's data, versus 3-4 months previously. Jane Street participation signals hedge fund crossover into venture. This speed reflects extreme capital availability for AI leaders but raises diligence concerns.