SaaStr 829: A Hands-On Guide to SaaStr's New AI Tools with SaaStr CEO and Founder Jason Lemkin

Podcast: The Official SaaStr Podcast: SaaS | Founders | Investors
Guest: Jason Lemkin, CEO & Founder, SaaStr
Date: November 12, 2025

Episode Overview

This episode is a practical, in-depth walkthrough by Jason Lemkin of SaaStr’s newly launched AI-powered tools for SaaS founders and operators, with a special focus on fundraising and startup benchmarking. Jason gives a candid, behind-the-scenes look at how each AI tool works, the problems it solves for founders, their surprising impact, and how they’re already being used by thousands in the SaaStr community. The tone is hands-on, direct, and occasionally playful, with Jason using real (and fictional) examples to illustrate the journey from founder confusion to investor readiness.

Key Discussion Points & Insights

1. The Philosophy Behind SaaStr AI Tools

• Founders are often "all wrong" about where they stand
  "No matter what founders I talk to, they're all wrong. Like they're all wrong. They think they're doing better than they are. They think their cash will last longer, they think there's fewer issues." (00:01)
• The tools were built to provide actionable, data-driven feedback—because optimistic guesswork is pervasive among founders.

2. Introduction to the Core AI Tools (03:55–05:28)

A. Digital Jason (AI Mentor)

• Trained on all SaaStr content and speakers since inception—serves as a B2B "therapist" and resource for SaaS questions.
• Example: Jason queries about a CFO missing cash projections, the AI gives targeted analysis and steps (staffing, discipline, forecasting).
• "Four misses on cash projections and 4 million less cash flow. That's a huge red flag. You need to get crystal clear on why it's so bad... You need a plan to either cut or miracle or raise more capital or both." (06:25–07:10)
• Used over 100,000 times, entirely free—great for feedback, catharsis, and scenario testing.

B. AI VC Suite

• Connect with 400+ VCs (top B2B, AI VCs being regularly added).
• Four core tools:
  • Startup Valuation Calculator
  • Pitch Deck Analyzer
  • Benchmarking Tool
  • VC Matchmaking
• All tools freely accessible, designed to be transparent, actionable, and honest—even if the feedback stings.

3. Deep Dive: How Each Tool Works

A. Startup Valuation Calculator

• Extensive data: Over 569,000 calculations performed; reflects benchmarks from over 5,000 deals.
• Usage examples:
  • AI SaaS company at $26M ARR, soon to hit $100M—valued at $383M+.
  • Same company at $20M ARR with 70% growth—valuation drops to $166M.
• Transparent about over-optimism:
  "It definitely reflects Bay Area multiples, right, and the AI frenzy. But that's who's getting funded." (29:10)
• Shows how growth rate, sector, and stage affect fundability odds.

B. Pitch Deck Analyzer

• Upload your deck, get a traction and quality score, and candid grade (B+, NF, etc.)
• Tied to real fundraising benchmarks (from Iconiq, Bessemer, Carta, SaaStr database, etc.).
• If the deck is fundable, can trigger automatic VC intros:
  "If your grade is high enough, we'll automatically ask if you want to meet with VC funds right here... We will go out and introduce you to them." (42:10)
• Quote on tough love:
  "We used to give a lot of F grades and that was a little triggering for folks, so we changed it to NF: not fundable." (39:02)

C. Benchmarking Existing Progress (Board Packs & Investor Updates)

• Upload a monthly investor update or board pack—see honest, comparative analytics.
• Example:
  • $1M ARR, 251% growth—AI benchmarks trajectory, burn, peer percentile ranking, and suggests financial runway.
• Quote:
  "It'll take your trailing growth rates... and predict out where it thinks your revenue will be one year from now... Pretty cool." (52:08)
• Realistic, cross-dataset benchmarking for objectivity.

D. VC Matchmaking

• Find precision-fit VCs by uploading your deck and filling in key info.
• Workflow adapts to readiness: "If you just want to take coffee meetings... that's okay... If you want meetings this week, click that."
• 150+ direct VC intros made so far.

E. Research VCs

• Helps surface funds that match by stated criteria—free and used widely.

4. SaaStr’s AI Agents Stack & Third-Party Tooling (01:08:55)

• Transparency on SaaStr’s Own Stack:
  Full list of AI agents used for sales, revops, outbound, etc. (Qualified, Delphi, Gamma, Momentum, Attention, etc.).
• Highlight on Qualified:
  "We just closed 100k deal that Qualified found for us yesterday last night, right?... Qualified did everything except have the call and close it." (01:09:51)
• Ability for users to submit favorite agents and contribute to open “playbook.”

Notable Quotes & Memorable Moments

• On founder overestimation:
  "Most founders think they're doing better than they think. Some—I used to think I was doing worse than I thought. Now you can just upload an investor update... That's what's different here." (21:45)

• On honesty and candor of the AI tools:
  "If you're not going to get funded, it's just going to tell you because there's few things that are, I think, a worse waste of founders time than trying to... get funded... if there's just no chance." (39:33)

• On data privacy:
  "We only retain [pitch deck] data if you want to retain it... If you get a high enough score that you want funding from VCs, we have to retain the data and the pitch deck for a period of time... Anything below [B/B+] is gone." (01:04:40)

• On founder benchmarking:
  "No one does this. And I find no matter what founders I talk to, they're all wrong... They think there's fewer issues." (21:45, 52:45)

Timestamps for Important Segments

• 00:01 – 02:58: Introduction & rationale for tools
• 03:55 – 08:12: Digital Jason (AI Mentor) demo
• 14:50 – 21:10: Launch of VC suite and overview of core tools
• 28:22 – 38:10: Startup Valuation Calculator walkthrough
• 38:10 – 44:33: Pitch Deck Analyzer demo & auto-intro logic
• 44:34 – 52:45: Benchmarking tool; board/investor update uploads
• 52:46 – 01:07:39: VC Matchmaking & data privacy Q&A
• 01:08:40 – 01:12:45: SaaStr's own AI agent stack; submission system; final recommendations

Final Thoughts & Takeaways

• SaaStr’s AI tools are designed for brutal but actionable honesty. Founders are urged to regularly benchmark themselves, get objective scoring for their decks, and use data-driven insights to improve fundability and operational rigor.
• The tools are constantly improving, fueled by user feedback and larger data sets.
• "Go to Saster AI and AIBC and try these tools. They're all free and fun." (01:11:59)

For anyone navigating SaaS growth or fundraising, this episode delivers an indispensable and practical playbook, rooted in real data and executed with Jason Lemkin’s no-nonsense, founder-centric style.