Notion co-founder on malleable software, monetizing agentic work, reinvention, more | Akshay Kothari

Notion co-founder on malleable software, monetizing agentic work, reinvention, more | Akshay Kothari

In this episode of Second Acts, Krish is joined by Akshay Kothari, co-founder at Notion [https://www.notion.com/]. Akshay shares notes on: The founding insight behind his first startup, Pulse (acq. by LinkedIn in 2013) and how that led him to Notion, the now-storied Kyoto reset that transformed a flailing, early version of the product, how the idea of building “malleable software” can be traced back to the origins of modern computing, what’s informing Notion’s agent-native second act and its multi-layered moat, learning to price work/intelligence over seats/platforms, how Notion's Custom Agents made usage-based monetization an incontestable choice, why Akshay turns to the necessary pragmatism of Buffet and Munger, defiant narratives, and much more. — Chapters: 00:00 — Episode highlights 03:31 — Pulse 06:12 — The Kyoto reset 08:58 — “Everything is a block” 11:16 — Malleable software 13:27 — Sugar-coated broccoli 15:26 — Selling work 19:15 — Switzerland of LLMs 23:32 — Pricing intelligence-as-a-service 31:22 — Margins and agents 35:02 — Think Together 38:39 — Freeing demos 42:13 — Munger’s valley — Referenced: Notion [https://www.notion.com/] Pulse [https://en.wikipedia.org/wiki/LinkedIn_Pulse] Ivan Zhao [https://x.com/ivanhzhao] Douglas Engelbart [https://en.wikipedia.org/wiki/Douglas_Engelbart] Alan Kay [https://en.wikipedia.org/wiki/Alan_Kay] Augmenting Human Intellect [https://www.dougengelbart.org/pubs/augment-3906.html] Malleable software [https://www.youtube.com/watch?v=I7K6ZlBY2tQ&feature=youtu.be ] Custom Agents [ https://www.notion.com/blog/introducing-custom-agents] Notes from Token Town [https://www.linkedin.com/pulse/notes-from-token-town-negotiating-fortune-5m-sarah-sachs-mlshc/] Landing on usage-based pricing [https://www.linkedin.com/posts/akothari_we-spent-a-fair-bit-of-time-deliberating-activity-7432191613185196032-qgdU] Think Together [https://www.youtube.com/watch?v=vkpYpWfEK5s] Notion Media Fellows [https://notion.pages.dev.notion.co/cbe4bae104b64834a48eae8f33df5555] Poor Charlie's Almanack [https://en.wikipedia.org/wiki/Poor_Charlie%27s_Almanack] — Connect with Akshay: LinkedIn [https://www.linkedin.com/in/akothari/] X [https://x.com/akothari] — Connect with Krish: LinkedIn [https://www.linkedin.com/in/krishs/] X [https://x.com/cbkrish] — About Chargebee: Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative AI monetization infrastructure.

Miro CEO on reaching 100m users + 250k orgs, permission to win, hybrid pricing, more | Andrey Khusid

In this episode of Second Acts, Krish is joined by Andrey Khusid, founder and CEO at Miro [https://miro.com/]. Andrey shares notes on: Miro's AI-native second act and how it's enabling them to expand horizontally and vertically at once while serving 100m users and most of the Fortune 500, the inputs that help Andrey constantly assess and intuit market fit, Miro's portfolio of bets approach, what strategic enterprise AI deployments actually demand, why monetization has long been a cross-functional team effort at Miro and why Andrey has always been part of it, how Miro is evolving beyond per-seat pricing, why he's back in founder-led sales mode, shifting from role-based to skill-based "maker teams", re-earning product-market fit: "it's not constant, we have to win it again and again," why Andrey is turning to Brian Balfour's Four Fits framework as they chart their “best-of-suites” path with AI, and much more. — Chapters: 00:00 - Episode highlights 01:28 - Episode intro 04:27 - Broad and deep JTBD 09:57 - A best-of-suite strategy 13:40 - Data behind Andrey’s intuition 16:14 - A portfolio of bets 19:40 - “PLG is not a business model” 24:16 - Evolving beyond per-seat pricing 28:50 - Miro’s monetization team 31:10 - The AI-led enterprise shift 34:28 - Founder mode redux 41:00 - Re-earning PMF 49:14 - Hiring former founders 56:00 - “Discipline is critical” 59:50 - 0-1 maker teams 01:01:38 - The enduring Four Fits 01:04:50 - Resilience — Referenced: Miro [https://miro.com/] MCP (Model Context Protocol) [https://www.anthropic.com/news/model-context-protocol] Menlo Ventures 2025 report [https://menlovc.com/perspective/2025-the-state-of-generative-ai-in-the-enterprise/] Slack [https://en.wikipedia.org/wiki/Slack_(software)] OpenAI/ChatGPT [https://en.wikipedia.org/wiki/OpenAI] Anthropic/Claude [https://en.wikipedia.org/wiki/Anthropic] Gemini [https://en.wikipedia.org/wiki/Gemini_(language_model)] Granola [https://www.granola.so/] Jeff Chow [https://www.linkedin.com/in/jjchow/] Jakob Knutzen [https://www.linkedin.com/in/jakobknutzen/] Butter [https://www.butter.us/blog/a-new-chapter-for-butter-with-miro] Tony Beltramelli [https://www.linkedin.com/in/tony-beltramelli-513b1219/] Uizard [https://uizard.io/blog/uizard-joins-miro/] Brian Balfour [https://www.linkedin.com/in/bbalfour/] The Four Fits framework (updated for the AI era) [https://blog.brianbalfour.com/p/the-four-fits-a-growth-framework] — Connect with Andrey: LinkedIn [https://www.linkedin.com/in/khusid/] — Connect with Krish: LinkedIn [https://www.linkedin.com/in/krishs/] X [https://x.com/cbkrish] — About Chargebee: Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra.

Pendo CEO on category creation, differentiated platforms, pricing MAUs, and more | Todd Olson

In this episode of Second Acts, Krish is joined by Todd Olson, CEO and Founder of Pendo [https://www.pendo.io/]. Todd talks about: why investors pushed him to sell to marketers in 2013 but he stubbornly built for product managers instead (a persona without a proven budget line), the decade-long journey of creating a new category from scratch, why raising minimum price from $99/m to $1,500/m overnight accelerated their growth, the platform vision that's been core to Pendo since 2014 and Todd’s "innovate at the intersections" philosophy, how AI is fundamentally reshaping product analytics (as "the incremental value of a click" has declined in the post-ChatGPT era), the innovator's dilemma facing scale-ups today, lessons from Bill Walsh's The Score Takes Care of Itself and why leading indicators matter more than lagging ones, running one’s own race, and so much more. — Chapters: 00:00 - Episode highlights 01:51 - Episode intro 04:25 - How Pendo created a budget line item 08:14 - Questions for AI-native product teams 10:14 - Devs vs PMs: JTBDs and inclinations 13:24 - New paradigms for product analytics 21:14 - Why charge for MAUs? 22:21 - A trajectory-shifting price change 27:19 - “We’ve been a platform since 2014” 31:57 - Differentiating on intersections 37:21 - Living the innovator’s dilemma 43:19 - “Run your own race” 46:24 - The Score Takes Care of Itself — Referenced: Amp It Up (Frank Slootman) [https://www.amazon.com/Amp-Unlocking-Hypergrowth-Organizations-Stagnation/dp/1119836115] Marty Kagan [https://www.linkedin.com/in/martycagan/] Silicon Valley Product Group [https://www.svpg.com/] Receptive (acquired by Pendo) [https://www.pendo.io/pendo-blog/pendo-acquires-product-feedback-innovator-receptive/] Crossing the Chasm (Geoffrey Moore) [https://en.wikipedia.org/wiki/Crossing_the_Chasm] ChatGPT [https://en.wikipedia.org/wiki/ChatGPT] OpenAI [https://en.wikipedia.org/wiki/OpenAI] Claude Code [https://www.anthropic.com/news/claude-code ] Lovable [https://lovable.dev/] Airtable [https://en.wikipedia.org/wiki/Airtable]: Intercom [https://en.wikipedia.org/wiki/Intercom,_Inc.]: Net Promoter Score [https://en.wikipedia.org/wiki/Net_promoter_score] Product Operating Model [https://www.svpg.com/the-product-operating-model/] Innovator's Dilemma (Clayton Christensen) [https://en.wikipedia.org/wiki/The_Innovator%27s_Dilemma]: The Score Takes Care of Itself (Bill Walsh) [https://en.wikipedia.org/wiki/The_Score_Takes_Care_of_Itself] — Connect with Todd: LinkedIn: https://www.linkedin.com/in/toddolson/ — Connect with Krish: LinkedIn: https://www.linkedin.com/in/krishs/ X: https://x.com/cbkrish — About Chargebee: Chargebee [https://www.chargebee.com/] helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra.

v0’s GM on powering the next 100m builders, monetizing infra products, and more | Zeb Hermann

In this episode of Second Acts, Krish is joined by Zeb Hermann, General Manager of v0 [https://v0.app/] at Vercel. Zeb unpacks: the biggest lessons from his time at Segment and Sequoia Capital, why he joined Vercel (makers of Next.js and AI SDK) to lead initiatives (such as pricing and packaging) with “asymmetric upside,” v0’s origins (as Vercel’s second act) and how it has exploded to reach millions of users in the most intensely competitive competitive of AI categories, how the v0 team is structured as customer zero within Vercel, why it takes Caltech PHDs to scale their infrastructure pricing, v0’s deep vertical adjacencies and the differentiation that that unlocks, what he envisions as the ideal monetization model for AI, some amazing book recs via lectures he attended at The Long Now Foundation, and so much more. — Chapters: (00:00) Episode intro (03:39) v0: Vercel’s magisterial second act (04:59) “What’s the scale of your ambition?” (10:23) Asymmetric upside  (12:20) No (long-term) random acts of AI (14:16) Being customer zero  (15:51) v0 as a startup within Vercel (19:55) v0’s unique PLG-enterprise barbell (23:48) Vercel’s deep vertical differentiation (29:35) Value, Caltech PHDs, and Vercel’s pricing (35:35) Expanding to adjacent product lines (38:56) “Should this even be a separate product?” (41:41) Margins and value-aligned AI monetization (43:43) Zeb’s radical, two-year vision for v0 (47:11) Zeb’s favourite books on scaling decisions  — Vercel [https://vercel.com/] Guillermo Rauch [https://twitter.com/rauchg] Next.js by Vercel [https://nextjs.org/] ShadCN UI [https://ui.shadcn.com/] Tailwind CSS [https://tailwindcss.com/] Nikita Shamgunov [https://www.linkedin.com/in/nikitashamgunov/] Segment [https://segment.com/] Zhenya Loginov [https://uk.linkedin.com/in/zhenyaloginov] Sequoia Capital [https://www.sequoiacap.com/] Miro [https://miro.com/] Opendoor CEO’s AI memo [https://x.com/CanadaKaz/status/1971622109614166342] Caltech [https://en.wikipedia.org/wiki/California_Institute_of_Technology] Harpreet Arora [https://www.linkedin.com/in/harpreet-arora/] Malte Ubl [https://www.linkedin.com/in/malteubl] Fluid compute [https://vercel.com/fluid] Fluid compute pricing [https://vercel.com/docs/functions/usage-and-pricing] Algorithms to Live By (Brian Christian & Tom Griffiths) [https://www.goodreads.com/book/show/25666050-algorithms-to-live-by] Scale (Geoffrey West) [https://www.goodreads.com/book/show/31920702-scale] The Long Now Foundation [https://longnow.org/] Magic Patterns [https://www.magicpatterns.com/] Greedy algorithm [https://en.wikipedia.org/wiki/Greedy_algorithm] — Connect with Zeb: LinkedIn [https://www.linkedin.com/in/peterzebhermann/] X [https://x.com/zeb_hermann] — Connect with Krish LinkedIn [https://www.linkedin.com/in/krishs/] X [https://x.com/cbkrish] — About Chargebee: Chargebee [https://www.chargebee.com/] helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra.

Docebo CEO on steady growth, systems of intelligence, pricing's value chain, and more | Alessio Artuffo

In this episode of Second Acts, Krish is joined by Docebo’s [https://www.docebo.com/] (NASDAQ: DCBO) CEO, Alessio Artuffo. Alessio talks about: Docebo’s many second acts from the early days of bootstrapping to their recent AI-native reinvention, what they have learned about sustaining balanced growth as a public SaaS company, how “clear, unarguable” enterprise value (not AI hype) drives their product and monetization decisions, the internal idea-to-execution value chain of pricing ownership, why focus (not TAM) is the big constraint in horizontal markets, a Lencioni classic he keeps going back to, and more. — Chapters: (00:01) Episode highlights (03:13) Episode intro (05:40) A brief note on Docebo’s 20-year path (07:14) Docebo’s many second acts (12:14) A philosophy of balanced growth (17:56) The post-COVID reset (21:39) System of record → System of intelligence (28:10) Real AI adoption starts with customer problems (31:57) Rewiring Docebo’s GTM for an AI-led future (34:23) AI, FedRAMP, and unlocking new markets (40:33) SI partnerships as multipliers (43:00) A methodical approach to AI monetization (46:54) Pricing “clear, non-arguable value” with simplicity (50:14) A hypothesis-led, cross-functional pricing process (55:54) Alessio recommends a Lencioni classic — Referenced: Docebo [https://en.wikipedia.org/wiki/Docebo] NASDAQ [https://en.wikipedia.org/wiki/Nasdaq] Edugo [https://www.docebo.com/edugo-ai/] “From System of Record to System of Intelligence:” [https://www.linkedin.com/posts/alessioartuffo_ai-futureofwork-learningtech-activity-7336753928232992771-t8hA?] Accenture [https://en.wikipedia.org/wiki/Accenture] Deloitte [https://en.wikipedia.org/wiki/Deloitte] Kyle Lacy [https://www.linkedin.com/in/kylelacy/] Mark Kosoglow [https://www.linkedin.com/in/mkosoglow/] FedRAMP [https://en.wikipedia.org/wiki/FedRAMP] The Five Dysfunctions of a Team [https://en.wikipedia.org/wiki/The_Five_Dysfunctions_of_a_Team] — Connect with Alessio: LinkedIn [https://www.linkedin.com/in/alessioartuffo/] — Connect with Krish LinkedIn [https://www.linkedin.com/in/krishs/] X [https://x.com/cbkrish] — About Chargebee: Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra. Learn more [https://www.chargebee.com/].