logo
episode-header-image
Jul 2025
1h 11m

Pricing your AI product: Lessons from 40...

Lenny Rachitsky
About this episode

Madhavan Ramanujam is the world’s foremost expert on pricing and monetization strategy. As managing partner at Simon-Kucher, he helped over 250 companies, including 30 unicorns, architect their pricing strategies. He’s the author of the definitive book on pricing, Monetizing Innovation. Now he’s back with a sequel, Scaling Innovation, which reveals how to build enduring businesses by dominating both market share and wallet share. He recently left Simon-Kucher to launch his own fund, 49 Palms, focused on helping early-stage AI companies.

In this conversation, we discuss:

1. The 2x2 framework that identifies your optimal pricing model

2. Why AI companies can capture 25% to 50% of value created, vs. 10% to 20% for traditional SaaS products

3. Why popular AI coding tools may have already doomed themselves with underpricing

4. The “give-and-get” framework top negotiators use to extract maximum value from every deal

5. The negotiation strategy that helped one founder 4x their deal size overnight

6. How to frame POCs as “business case creation” instead of technical demos (and why this changes everything)

7. Why AI companies must get monetization right from day one—not “figure it out later”

8. How companies like Intercom’s Fin and Sierra pioneered outcome-based pricing (charging $0.99 per AI resolution)

9. The single question that reveals if your pricing is too complex

Brought to you by:

Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny

DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny

Persona—A global leader in digital identity verification: https://withpersona.com/lenny

Transcript: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109183/my-biggest-takeaways-from-this-conversation

Where to find Madhavan Ramanujam:

• X: https://x.com/madhavansf

• LinkedIn: https://www.linkedin.com/in/madhavansf/

• Promo email for Scaling Innovation: promo@49palmsvc.com — If you’re purchasing more than five copies, send a screenshot of your receipt to enter Madhavan’s exclusive bundle raffle.

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Introduction to Madhavan and his work

(04:30) The core thesis of Scaling Innovation

(09:20) Common traps founders fall into

(12:06) Beautifully simple pricing

(15:00) Mastering negotiations

(26:51) Other strategies for effective pricing and monetization

(27:35) How AI pricing is different

(31:33) Handling POCs

(36:25) The importance of mastering monetization

(38:58) Choosing the right AI pricing model

(43:13) Current trends in AI pricing

(44:48) Strategizing for outcome-based models

(50:23) Packaging strategies for scaling

(51:37) Adapting pricing strategies over time

(53:40) Key axioms for pricing success

(58:00) Takeaways for founders

(01:01:33) Lightning round and final thoughts

Referenced:

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan

• Cursor: https://www.cursor.com/

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Sierra Finn: http://www.sierrafinn.com/

• Chargeflow: https://www.chargeflow.io/

• GitHub: https://github.com/

• Intercom: https://www.intercom.com/

• Warren Buffett’s quote: https://www.goodreads.com/quotes/11478913-if-you-ve-got-the-power-to-raise-prices-without-losing

• Sierra: https://sierra.ai/

• Clay Bavor on LinkedIn: https://www.linkedin.com/in/claybavor/

Mission: ImpossibleThe Final Reckoning: https://www.imdb.com/title/tt9603208/

• Delphi: https://www.delphi.ai/

• Dara Ladjevardian on LinkedIn: https://www.linkedin.com/in/dara-ladjevardian/

• Sam Spelsberg on LinkedIn: https://www.linkedin.com/in/samuel-spelsberg/

• Lennybot: https://www.lennybot.com/

• Granola: https://www.granola.ai/

• Simon-Kucher: https://www.simon-kucher.com/

• Josh Bloom on LinkedIn: https://www.linkedin.com/in/joshuabloompricingconsulting/

Recommended books:

Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

Scaling Innovation: How Smart Companies Architect Profitable Growth: https://www.amazon.com/dp/1119633060

Business Model Generation: A Handbook for Visionaries, Game Changers, and Challengers: https://www.amazon.com/Business-Model-Generation-Visionaries-Challengers/dp/0470876417

Thinking Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/

Contagious: Why Things Catch On: https://www.amazon.com/Contagious-Things-Catch-Jonah-Berger/dp/1451686587/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.



To hear more, visit www.lennysnewsletter.com
Up next
Today
A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett
<p><strong>Rachel Lockett</strong> is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks f ... Show More
1h 45m
Nov 20
Slack founder: Mental models for building products people love ft. Stewart Butterfield
<p><strong>Stewart Butterfield</strong> is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In t ... Show More
1h 30m
Nov 16
The Godmother of AI on jobs, robots & why world models are next | Dr. Fei-Fei Li
<p><strong>Dr. Fei-Fei Li </strong>is<strong> </strong>known as the “godmother of AI.” She’s been at the center of AI’s biggest breakthroughs for over two decades. She spearheaded ImageNet, the dataset that sparked the deep-learning revolution we’re living right now, served as Go ... Show More
1h 19m
Recommended Episodes
Jun 2024
Price Like a Pro: Alvaro Morales Unlocks Revenue Secrets | Co-Founder and CPO at Orb | E222
Join us in this episode with Álvaro Morales, CEO of Orb, as he explores product pricing strategies that align value and revenue. From his start as a software engineer at Asana to his current role leading pricing innovation, Álvaro offers insights into initial pricing decisions an ... Show More
32m 5s
Nov 2024
Can this AI Chip Startup Beat NVIDIA? (Spotlight)
<p>Is it possible for a startup to compete with NVIDIA, the $1 trillion behemoth dominating AI hardware? Thomas Sohmers and his team at Positron are betting they can and they're moving at lightning speed to prove it.</p> <p><br /></p> <p>In this episode, Chris Saad sits down with ... Show More
44m 55s
Nov 2024
How Tibo Sold over $10M in SaaS Products by Breaking All the Rules of Traditional Product Building
<p>As I’ve often said, PMs and aspiring PMs can learn a lot from the scrappy, relentless mindset of solopreneurs and indie hackers. Today’s episode is a masterclass in just that.</p><p>In this podcast, he pulls back the curtain on rapid product validation, the perils of building ... Show More
1h 51m
Apr 2025
Next-Gen Founders: Startups in the Age of AI (Edu)
Is AI making startups easier—or just changing the rules of the game?In a world where execution is cheap and accessible, building a successful startup is more competitive than ever. In this episode, Chris Saad and Yaniv Bernstein unpack the reality of every business having access ... Show More
53m 2s
Oct 22
Startup to Pitch Champion: How Reekon Tools has Grown Sustainably
<p><span style="font-weight:400;">Building a profitable hardware brand without venture capital requires strategic thinking, authentic relationships, and unwavering focus on cash flow management. In this episode of B2B Breakthrough, host Ciara Cristo chats with Christian Reed (</s ... Show More
37m 49s
Oct 22
Amazon’s “Age of Efficiency,” LLM distribution, AI wearable worries, and more with Elad Gil | E2197
Today’s show:*Amazon’s dropping a LOT of employees for AI and robots… are Jason’s darkest predictions coming true?Legendary investor Elad Gil joins Jason and Alex for the full show today! Together, they’re digging into the Amazon news, looking back at Jason’s predictions from jus ... Show More
1h 23m
Aug 18
20VC: Lovable CEO Anton Osika on $120M in ARR in 7 Months | The Honest Truth About Defensibility and Unit Economics for AI Startups | The State of Foundation Models: Long Grok, Short OpenAI, Why | Replit vs Lovable vs Bolt: What Happens
<p dir="ltr">Anton Osika is the Co-Founder and CEO @ Lovable, the fastest growing company on the planet. In just 7 months, they have scaled from $0 to $120M in ARR. They have raised over $200M in funding from some of the best including Accel, Creandum and 20VC. Their latest round ... Show More
1h 8m
Sep 3
SEO Is Dead: The #1 Skill You Need in 2025
Want Kipp's Loop Marketing Prompt Library (over 100 prompts)? Get it for free: https://clickhubspot.com/elm Episode 74: Is SEO really dead—and if so, what’s the number one marketing skill you need to stay ahead in 2025? Matt Wolfe (https://x.com/mreflow) and Kipp Bodnar (https:// ... Show More
46 m
Nov 2024
How to Do Product Discovery Right with Pawel Huryn, 175K+ on LinkedIn, Senior PM and Author
<p>This episode is a masterclass in modern product management—featuring cutting-edge frameworks, actionable strategies, AI integration, competitive edge tactics, and aligning product goals with overarching business objectives.</p><p></p><p>In today's episode, we cover:</p><p></p> ... Show More
1h 32m
Aug 18
He built the top AI agent startup | Flo Crivello, Former PM, now CEO & Founder, Lindy AI
If you’ve ever said “I just wish I had an assistant who knew exactly how I think”... Lindy is that assistant. These agents aren’t demos. They’re real, customizable workflows anyone can build. No code.Flo Crivello (founder of Lindy and ex-Cruise/YC) joined us to show how his perso ... Show More
53m 10s