Most important take away

B2B SaaS sold to tech buyers is in a brutal, multi-year contraction (Salesforce, Mongo, Workday all guiding down, NRR collapsing as customers cut seats to free AI budget) while consumer SaaS, vertical SaaS, security, and SMB plays (Canva, Toast, Samsara, Klaviyo, Zscaler, Monday) are still growing 30 to 50 percent. The career and capital implication: AI is table stakes you must ship even though no one has proven it drives net new revenue yet, liquidity has been dead since 2021 with only two SaaS IPOs (Klaviyo, Rubrik) trading at a punishing 6x, and the venture math only pencils out if multiples reflate to roughly 8x by end of 2025.

Summary

Actionable insights and patterns worth pulling out:

Career and operator advice

• Always ask the budget question on the first enterprise discovery call (“Is this purchase budgeted for this year?”). Lemkin says all the best reps do it; enterprise buyers respect it because it frames the conversation. New reps feel salesy asking it; do it anyway.
• Know exactly where your customer’s budget is coming from. With Sass spend flat to substitutional, founders can no longer assume a rising tide. Many “happy” customers are churning specifically to free up AI budget. If you can’t name the line item you are replacing, you are exposed.
• AI is table stakes, not a moat. Lemkin: founders hiding from, mocking, or deprioritizing AI features are on “a path to destruction.” Even though there is no proven revenue lift (Dell, Salesforce, ServiceNow all show no clean AI revenue uplift yet), customers expect parity with the category leader. Build it now, monetize later.
• The “experiment budget” is real but small. There is no dedicated AI line item at most CFOs. Money comes from killing existing tools (Lemkin cites a portfolio call where a customer planned to cut 12 apps to buy 1 AI app).
• Watch your founder for “acquiescence” as the leading indicator of decline. The earliest sign a founder has quit, per Lemkin: when they start covering for mediocre VPs in board meetings (“Jim’s doing a fine job” after two missed quarters). At that point, regrowth is essentially impossible.
• “Do the things that are easy for you that are hard for other people” (Sam Altman quote Lemkin cites). Applies to choosing a business, a content channel, or a moat.
• Pick a board that will push you, not flatter you. Lemkin would pick Tobi Lutke today because “we have too many founder-friendly Yahoos.” Founder-friendly is a comfort trap.
• The best founder meetings are ones where you can “see the future through the founder.” If you can’t, pass — regardless of how the deck looks.

Tech and product patterns

• High NRR is no longer a guarantee. The old enterprise SaaS playbook (115 to 120 percent NRR carries you forever, even with zero new logos — Fastly grew 15 percent last year with zero net new customers) is breaking. Salesforce, the most enterprise SaaS company, just fell to single-digit growth. Seats are being cut, expansion deals are shrinking. Don’t assume NRR will save you.
• Multi-product is existential past a certain scale. Lemkin says HubSpot got this right; Box is partially there; Dropbox is essentially still one product and is paying the price. Sequence your next acts early — doing it after growth stalls is “so hard.”
• Vertical SaaS, security, consumer SaaS (B2B2C like Canva), and SMB are working. Pure B2B-to-tech is broken. If you sell to engineering, marketing tech, or DevTools buyers, expect pain. Examples of strength: Canva (40 percent at 2.3B), Toast (32 percent at 1.3B), Samsara (39 percent at 1.1B), Monday (34 percent at 900M — notably does NOT sell to tech), Zscaler (32 percent at 2.2B), Klaviyo (42 percent at 800M).
• The “microbrand” inbound effect kicks in around 2 to 10M ARR in a vertical. Roughly half your pipeline starts coming free from community word of mouth. But CAC doesn’t actually drop because that’s exactly when you layer in paid sales and marketing to scale.
• Public SaaS has made “a terrible pact with the devil” — markets demand 30 to 40 percent operating margins, leaving no money for R&D or true sales investment. Stay private as long as you can. Get profitable the year before IPO, not six years before (Palantir playbook: 20 percent gross margins, then magically 70s the year before listing).

Fundraising tactics

• Don’t ask for too much. The single biggest unforced error today. A Gong Series A in 2017 was 7M; that’s a seed today. Many investors silently pass if your ask exceeds the largest check their fund can write. Lemkin’s max check is 4M; if you ask for 10M he has to bring in a co-lead, so the bar is dramatically higher.
• Ranges are okay early (“2 to 5” or “4 to 6”) for first-time founders; not okay for third-time founders.
• Ignore 2021 advice about running tight processes with one-hour decision windows. That playbook is dead and signals you got your advice from the wrong place.

Liquidity and venture math

• Only two SaaS IPOs since December 2021 (Klaviyo, Rubrik), both trading at 6x. The math doesn’t work above 100M rounds without a 30 to 40 percent multiple reflation.
• Tomasz Tunguz data point: ~57 software exits per year above 50M for a decade — a flat number while SaaS scaled 20x to 30x. Getting acquired is much harder than founders assume. “It needs to be 570 for venture math to pencil out.”
• Regulators are now a real M&A blocker (Adobe-Figma was the wrong call in Lemkin’s view; Adobe’s real competitor was Canva, not Figma). Google-HubSpot at 33B is a coin flip on antitrust depending on whether regulators frame HubSpot as a marketing company (likely blocked) or a CRM (likely allowed).
• Private equity is no longer a guaranteed soft landing. Vista wrote PluralSight down to zero from 3.5B because the 1.5B debt load couldn’t be serviced. If multiple PE deals (Avalara, Zendesk at 10B) crater similarly, the next-gen LBO buyer of SaaS dries up too.
• Mark-to-market discipline: Lemkin took a “big red marker” to his portfolio at year-end and marked down aggressively. TVPI inflation through endless extension rounds and structured insider rounds is “corrupt behavior.” Sell secondaries aggressively in winning growth-stage deals — even 1x outcomes at scale are fine if a fund returner exists.
• Liquidity advice for individuals: do not invest in venture funds. The lockup-to-return math no longer works for retail-scale checks.

The bet Lemkin made on-air: average public SaaS multiple back to 8x by 12/31/2025. He bet 20K, smaller than usual because he’s burned out on losing bets.

Chapter Summaries

1. PluralSight goes to zero. Vista wrote off 3.5B after acquiring at that price with 1.5B of debt that the business couldn’t service even at ~80M FCF. The PE-as-savior thesis for SaaS exits is now in doubt.

2. Salesforce’s 20 percent drop and the death of NRR. The crash wasn’t the miss — it was the guide to single-digit growth indefinitely. Customers cutting seats and shrinking deal sizes. Even enterprise NRR is no longer reliable.

3. B2B-to-tech vs. B2B-to-everyone-else. Tech buyers are still cutting 2+ years in. Non-tech (consumer, vertical, security, SMB) is growing 30 to 50 percent. Examples: Canva, Toast, Samsara, Monday, Zscaler, Klaviyo.

4. AI as table stakes with no proven revenue. Dell, Salesforce, ServiceNow all show no clean AI uplift. Budget is substitutional (kill 12 apps, buy 1). Build it anyway or get steamrolled.

5. Founder fatigue and CEO transitions. UI Path’s Daniel Dines returning, HubSpot’s Halligan stepping back, Twilio pushing out Lawson. Founder-led tends to win long-term but everyone gets tired.

6. M&A and regulators. Google-HubSpot at 33B is plausible but antitrust-risky. Adobe-Figma was the wrong call — Canva was always the real threat to Creative Cloud.

7. The liquidity problem. Only two SaaS IPOs since 2021 (Klaviyo, Rubrik) at 6x. ~57 software exits >50M per year for a decade. Math doesn’t work above 100M post.

8. Mongo’s 23 percent drop. The shock wasn’t the number — it was a beloved high-flyer with strong competitive position falling to teens growth. Means even the best-positioned enterprise SaaS isn’t safe.

9. Notion and growth-stage valuations. At 30B+, has to beat HubSpot or Atlassian to make the math work. Lemkin’s rule: take secondary aggressively above ~1B as an early investor.

10. TVPI vs. DPI and markdown discipline. Markups distort behavior; LPs are judged on TVPI so it persists; Lemkin marked his book down aggressively at year-end.

11. Tweet of the week — don’t raise too much. Asking for 10M when your stage warrants 4M silently disqualifies you from most funds. Use ranges if you must. Stop using 2021 fundraising advice.

12. SaaStr and events as a business. Lost ~60+ unicorn sponsors; flat-to-down year. Events work as a marketing layer for a fund if you’re great at them and the team is strong; otherwise the time ROI is poor.

13. Quickfire. Best first founder meeting: Parker Conrad at Zenefits. Board pick: Tobi Lutke. Early sign a founder has quit: covering for mediocre VPs. Worst bet: thought IPO window would reopen in H2 2024. Next bet: 8x average SaaS multiple by end of 2025, 20K stake.