The Twenty Minute VCPredictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges
CHAPTERS
- 0:00 – 0:53
Rapid-fire cold open: IPO wave, venture’s “no ceiling,” and AI jobs anxiety
Before the formal “quiz” begins, the panel jumps straight into bold claims about a packed IPO calendar and how AI is reshaping venture math. They also tee up a recurring theme: fear of AI-driven unemployment and the potential political backlash.
- •Predicted IPOs: SpaceX, Canva, Databricks, Anthropic; OpenAI delayed due to burn
- •Claim that venture upside now has “no ceiling,” changing ownership/round dynamics
- •Agents are still early—“we haven’t missed the boat” on what they can do
- •Unemployment fears could trigger a major anti-tech/anti-AI backlash
- •Framing: society may become “terrified of AI,” investors want to “own the robots”
- 0:53 – 5:06
Founder of the Year debate: Anthropic’s Dario and the product that unlocked “vibe coding”
Harry kicks off the Big Fat Quiz format with Founder of the Year. Jason and Rory converge on Dario Amodei, arguing Anthropic’s Claude releases made a step-change in product usefulness across coding and beyond, while acknowledging controversy around unemployment rhetoric.
- •Claude 3.5/3.7/4 cited as the enabling layer for modern AI tooling (Cursor, Replit, Lovable, etc.)
- •Question of whether product excellence should translate to founder/CEO credit
- •Rory praises Anthropic’s “steady hand”: profitability posture, valuation convergence, strong growth
- •Tension between CEO as operator vs CEO as public “pontificator” (jobs claims)
- •Comparison to “Messi” dynamic: some awards become repetitive without exclusions
- 5:06 – 8:33
More Founder of the Year contenders: SpaceX’s Gwynne Shotwell, Scale’s Alex Wang, and Robinhood’s Vlad
The discussion broadens from Dario to operational leadership and investor outcomes. Gwynne Shotwell is lauded for steering SpaceX through geopolitical/brand complexity, Alex Wang for exceptional investor returns, and Vlad Tenev for Robinhood’s multi-product execution.
- •Gwynne Shotwell nominated for navigating SpaceX scale, geopolitics, and Elon-related brand drag
- •Expectation set: SpaceX could be the biggest IPO ever; Shotwell ‘wins next year’ sentiment
- •Alex Wang/Scale: exceptional liquidity/returns vs debated “world impact”
- •Robinhood: transformation from meme app to trusted platform; many products crossing $100M revenue
- •Theme: execution and timing (“moment in time”) as a founder superpower
- 8:33 – 13:03
Fund of the Year: Index’s exit-heavy year vs Neo’s ‘aesthetics’ and accelerator resurgence
Rory anchors the award in realized outcomes and points to Index’s concentration in marquee wins. Jason adds a second lens—brand/aesthetics and early entry into breakout AI deals—spotlighting Neo and the renewed relevance of accelerators and communities.
- •Rory’s criteria: exits/liquidity as the objective yardstick; Index highlighted (Wiz, Figma, Revolut)
- •Jason’s “aesthetics” lens: Neo’s early bets (Cursor, Calshi, Cognition) and hands-on sourcing
- •Accelerator/composer ecosystem: YC dominance but Neo/SPC/HF0 seen as resurgent forces
- •Crandum cited for strong European execution and brand building
- •Debate: absolute dollars vs multiples and narrative influence in venture reputations
- 13:03 – 18:47
Stage-based winners: Hummingbird, Benchmark, Thrive, Founders Fund—and Google as ‘corporate investor’
Harry breaks the category into Seed, Series A, and Growth, emphasizing discipline to stage and repeatable selection. The conversation then expands to corporate capital, with Google credited for unusually large ownership stakes in generational assets.
- •Hummingbird: a small fund with an outsized return profile; early exposure to Lovable/Kraken mentioned
- •Benchmark: praised for staying true to early-stage knitting while producing major outcomes
- •Thrive: growth-platform expansion, multiple vehicles, central positions (OpenAI, Cursor, Databricks, etc.)
- •Founders Fund: rapid $3B deployment into Stripe/SpaceX/Anduril; LPs trade speed for quality
- •Google’s stakes: SpaceX, Anthropic, and Waymo framed as a dominant ‘corporate investor’ portfolio
- 18:47 – 21:27
Investor of the Year: solo-GP brand power vs cold, hard liquidity
The panel shifts from firms to individuals and what “wins” in a year. Rory highlights Elad Gil’s ability to raise massive solo vehicles as a signal of brand and perceived taste, while Harry emphasizes liquid exits as the ultimate scoreboard.
- •Elad Gil nominated for raising a ~$3B solo fund (and what that implies about track record/brand)
- •Discussion of ‘solo’ versus having a real operating team behind the scenes
- •Harry nominates a Kleiner Perkins investor for two big liquid outcomes (Windsurf, Chronosphere)
- •Rory’s ‘Great Exit Database’ framing: rank real exits by size and ownership to remove hype
- •Core tension: fundraising/brand vs realized distributions as the true metric
- 21:27 – 28:35
Breakout companies of 2025: OpenEvidence’s wedge strategy, Databricks’ AI pivot, and ElevenLabs’ ARR surge
They define “breakout” as a company that went from low awareness to major impact in-year. Rory spotlights OpenEvidence’s doctor-first LLM search wedge, Jason argues Databricks transformed by riding the AI wave, and Harry picks ElevenLabs for explosive scale and defensibility.
- •OpenEvidence: targeted doctors as the primary research-search user; rapid adoption (~500k US doctors)
- •Monetization logic: high-intent medical queries create premium pharma advertising real estate
- •Databricks: shift from data/compute story to AI beneficiary; growth acceleration cited (~55%)
- •ElevenLabs: scale to hundreds of millions ARR; defended position against incumbents
- •Meta-point: breakout often comes from nailing distribution + dramatic value/time savings for end users
- 28:35 – 35:47
Biggest surprises of 2025: AI talent wars, exploding private valuations, and ‘circular’ deal acceptance
The surprises center on market norms breaking under AI pressure. Rory is stunned by extreme compensation and ‘acqui-hire’ behavior, while Jason emphasizes how unprecedented upside and late-stage ownership dynamics have reshaped venture incentives; Harry flags chaotic deal sagas and circular financing.
- •Talent wars: eye-watering comp packages and ‘buy the team, keep the husk’ acquisitions
- •Windsurf deal turbulence and the broader erosion of conventional M&A norms
- •Venture upside shock: trillion-dollar IPO plausibility; rapid step-ups for AI companies
- •Circular deals normalize: fewer people care as long as marks and stock prices rise
- •Debate: whether private-market calibration will hold once massive companies price in public markets
- 35:47 – 45:24
Predicting 2026 stock winners: momentum vs valuation risk, and why ‘attach + pricing’ is everything
A ‘best performing stock’ question turns into a framework discussion: small-cap randomness, momentum persistence, and AI-driven re-acceleration. Jason argues the next winners will be companies that can truly charge for AI (not just bundle it), with Salesforce positioned as a major beneficiary if Agentforce delivers measurable labor replacement.
- •Rory critiques forecasting: the prior year’s top performers skew to smaller, idiosyncratic names
- •Jason’s B2B momentum basket (Palantir, Cloudflare, Mongo, Shopify, CrowdStrike, Snowflake) and persistence thesis
- •Down-year SaaS names reframed as opportunity if they prove real AI attach and pricing power
- •Salesforce thesis: massive installed base hungry for deployable agentic GTM outcomes; potential for large ACV uplift
- •Warning on ‘Copilot’ era: too little value to charge, too separate to bundle—worst-of-both-worlds execution
- 45:24 – 54:50
Why Salesforce could be a 2026 ‘buy’: net-new bookings vs ‘AI-influenced’ spin, and Notion’s pricing lesson
They sharpen the criteria for AI success in SaaS: net-new bookings and durable renewal value, not vague attribution. Adobe is criticized as a cautionary tale, while Notion is praised for earning (and sustaining) a meaningful price step-up through genuinely improved workflows.
- •Key standard: AI must create net-new bookings and/or pricing expansion, not just ‘AI-influenced revenue’
- •Bundling risk: mis-attributing revenue to AI can backfire at renewal if customers drop the add-on
- •Notion example: users pay materially more because AI changes the product’s usability and speed
- •Salesforce/ServiceNow upside: if agentic offerings reliably deliver labor/time savings, attach can scale rapidly
- •Execution challenge at hyperscale: big orgs risk self-deception when product quality signals get diluted
- 54:50 – 1:01:50
Buy one, short one (mega-cap edition): Google vs NVIDIA, CapEx cycle timing, and the case against shorting
Harry forces a 2026 trade across mega-caps, prompting a debate about AI CapEx duration and timing risk. Rory chooses long Google/short NVIDIA on asymmetric exposure to CapEx sentiment, while Jason argues NVIDIA’s demand and strategic reinvestment make it dangerous to short in a one-year window.
- •Rory: buy Google for upside and resilience; short NVIDIA if CapEx acceleration stalls
- •Apple/Amazon/Microsoft framed as ‘meh in the middle’ on AI-driven lift, with Apple’s multiple risk noted
- •Jason: 2026 is too soon for meaningful GPU displacement; hardware timelines don’t move like software
- •Shorting critique: being ‘right’ but early is still losing; puts worsen the timing tax
- •NVIDIA seen as actively ‘lubricating’ the ecosystem with reinvestment and strategic circular partnerships
- 1:01:50 – 1:08:01
IPO speculations for 2026: trillion-dollar listing mechanics and a four-IPO forecast
They explore which private giants could realistically go public and what it takes to float a company near a trillion-dollar valuation. Rory highlights the banking/market-structure challenge of generating demand and managing lockups at enormous scale, while Jason delivers a specific sequence of IPO predictions.
- •Rory: Anthropic more manageable than OpenAI/SpaceX; Stripe seen as least likely
- •Structural issue: creating demand and handling lockups when the float is small vs total equity value huge
- •Public markets vs private marks: pricing discovery risk for $500B+ to $1T+ companies
- •Harry’s bet: Anthropic + SpaceX IPO; Databricks/OpenAI/Stripe not in 2026
- •Jason’s sequence: SpaceX, Canva, Databricks, Anthropic (OpenAI pushed to ~2027)
- 1:08:01 – 1:12:54
AI and employment: measuring real unemployment impact and anticipating the backlash
The closing prediction question tackles whether AI-driven job losses will show up in official statistics by end of 2026. Rory argues backlash can occur regardless of causality because AI leaders have ‘confessed’ to disruption, while Jason believes hard data would escalate fear and make AI the defining dinner-table issue.
- •Rory: politics won’t wait for causality—unemployment upticks plus AI leaders’ rhetoric triggers a ‘tech lash’
- •Jason: official BLS-style confirmation of AI job loss would intensify societal fear and scrutiny
- •Backlash drivers: CEO signaling, narrative ownership, and scapegoating during downturns
- •Economic nuance: impact may be uneven (coding/support first) vs broad service economy effects later
- •Investor takeaway: owning ‘the robots’ is a hedge if disruption accelerates
