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Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099

Every single 20VC episode is recorded with Riverside.FM. It is the one product that I could not live without. Try it today here (https://creators.riverside.fm/20VC) and use the code 20VC for 15% off. ----------------------------------------------- Joining Harry in the hot seat today is Jason Lemkin, Founder @ SaaStr and one of the OG SaaS investors of the last decade. ----------------------------------------------- Timestamps: (00:00) Intro (01:45) OpenAI as 2023's Best Company (04:16) HubSpot's Long-Term Business Model (08:36) Challenges with Wealthy Founder VCs (12:13) Highlighting 2023's Best Founder (15:17) SaaS Performance Trends in 2023 (18:54) Insights from Bill Gurley's Exit Strategy Tweet (21:29) Updating Founder Advice (22:49) Y Combinator: Leading Early-Stage Fund (25:59) Kleiner's Remarkable Comeback (30:21) Identifying Top Late-Stage Funds (32:19) The Lack of Greed in 2023 (33:16) Surprises Emerging in 2023 (34:27) Reserve Deployment: Identifying Winners and Losers (37:28) The Key Role of Supportive Investors (46:33) Predicting the SaaS Landscape in 2024 (52:43) IPO Outlook for 2024 (01:02:49) Trump's Influence on the VC Economy (01:11:32) Quick-Fire Round ----------------------------------------------- The discussion today is broken into two segments: 2023: A Year in Review: Breakout company Best early-stage fund Best late-stage fund Most surprising event Founder of the Year 2024: Predictions: What is to Come: Does the IPO window open? Do Stripe, Databricks, and more go public? What happens to early-stage venture markets? Does the growth stage come roaring back? What happens to the M&A market? How does Trump change the startup ecosystem? Will a generation of young VCs be washed out the system? Will a ton of venture firms shut down? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Jason Lemkin on Twitter: https://twitter.com/@jasonlk Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #VentureCapital #JasonLemkin #SaaStr #2024elections #2024predictions #harrystebbings

Jason LemkinguestHarry Stebbingshost
Jan 3, 20241h 32mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Jason Lemkin Dissects Venture Reality: SaaS Saturation, Decacorns, Trump, 2024

  1. Jason Lemkin and Harry Stebbings review 2023 in venture and SaaS, highlighting explosive AI growth (OpenAI, Midjourney), standout operators like HubSpot and Nvidia, and the broken dynamics of late-stage funding and reserve models.
  2. Lemkin argues that SaaS growth deceleration may be partially permanent as software spend nears saturation, while early-stage remains vibrant and venture increasingly becomes a permanent hunt for decacorns, not just unicorns.
  3. They explore the changed LP/VC environment, founder behavior during the 2021 bubble (secondaries, entitlement, ‘run-for-salary’ startups), and the shift in advice around when to sell or go public amid compressed multiples.
  4. Looking to 2024–25, they predict more IPOs out of necessity, a wave of mid-sized M&A, continued AI-driven concentration of capital, and a weeding out of mediocre VCs and “pretty good” founders who can’t deliver outlier outcomes.

IDEAS WORTH REMEMBERING

5 ideas

SaaS growth has structurally slowed, even as efficiency and stock prices improved.

Public SaaS grew only ~16% in 2023 while stocks rose ~41%, largely driven by price increases and upsell into the base rather than new logo growth; Lemkin worries some demand deceleration may be permanent as software’s share of GDP saturates.

Venture is now a permanent decacorn-hunting business, not a unicorn-hunting one.

Post-2021, LP expectations and fund sizes mean Series A+ investors must underwrite Stripe/Databricks/OpenAI-scale outcomes; sub-multi-billion exits rarely move the needle for large funds, shifting risk appetite and selection criteria.

Reserve behavior has changed: many big funds are not reliably doing pro rata anymore.

Overvalued ‘middle-corn’ portfolios and broken reserve models have pushed multi‑billion funds to skip pro rata even in good companies, forcing founders to identify one catalytic insider who will actually lead and socially force others into a round.

Founder incentives in the 2021 bubble often became misaligned with stakeholders.

Large secondaries (e.g., nine‑figure cash-outs) and overfunded seeds created many ‘run-for-salary’ companies; Lemkin argues that when founders put themselves financially ahead of employees, customers, and investors, long‑term outcomes almost always suffer.

Advice on when to sell has flipped: windows of liquidity should be taken seriously.

Lemkin now regrets uniformly telling founders to “never sell if it’s working,” seeing many who declined peak 2020–21 offers and will never see those prices again; he aligns more with Bill Gurley’s view that venture returns concentrate in short liquidity windows that must be used.

WORDS WORTH SAVING

5 quotes

This is the first year I’m worried. The deceleration that we saw last year, I am worried some of it may be permanent.

Jason Lemkin

We are permanently decacorn hunters now. I don’t think there are unicorn hunters anymore.

Jason Lemkin

If you get a good offer and it’s in bullish times, take it, because it may be a decade until we see another boom like 2021.

Jason Lemkin

If you don’t know in 20 minutes that this is one of the best founders you’ve ever met, don’t do the investment.

Jason Lemkin

You’ve got to remember, it’s not your money. You gave it to them. It’s not your money to get back.

Jason Lemkin (relaying an LP/VC perspective)

2023 review: standout companies, founders, and funds (OpenAI, Midjourney, HubSpot, Nvidia, YC, Kleiner)Venture economics: fund size, reserves, LP expectations, and decacorn huntingSaaS market dynamics: efficiency gains, slowed growth, potential saturation of software spendFounder behavior and incentives: secondaries, “run-for-salary” companies, ethical questionsIPO and late-stage outlook: Stripe, Databricks, ServiceTitan, multiples, and timingM&A environment and regulatory impact, including Figma/Adobe and potential Trump effectsVC craft: what makes a great investor, marking down portfolios, and the necessity of outliers

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