Second Acts with Krish Subramanian

In this episode of Second Acts, Krish is joined by Akshay Kothari, co-founder at Notion.

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.

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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

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Referenced:

Notion

Pulse

Ivan Zhao

Douglas Engelbart

Alan Kay

Augmenting Human Intellect

Malleable software

Custom Agents

Notes from Token Town

Landing on usage-based pricing

Think Together

Notion Media Fellows

Poor Charlie's Almanack

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Connect with Akshay:

LinkedIn

X

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Connect with Krish:

LinkedIn

X

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative AI monetization infrastructure.

In this episode of Second Acts, Krish is joined by Andrey Khusid, founder and CEO at Miro.

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.

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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

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Referenced:

Miro

MCP (Model Context Protocol)

Menlo Ventures 2025 report

Slack

OpenAI/ChatGPT

Anthropic/Claude

Gemini

Granola

Jeff Chow

Jakob Knutzen

Butter

Tony Beltramelli

Uizard

Brian Balfour

The Four Fits framework (updated for the AI era)

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Connect with Andrey:

LinkedIn

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Connect with Krish:

LinkedIn

X

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra.

In this episode of Second Acts, Krish is joined by Todd Olson, CEO and Founder of Pendo.

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.

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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

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Referenced:

Amp It Up (Frank Slootman)

Marty Kagan

Silicon Valley Product Group

Receptive (acquired by Pendo)

Crossing the Chasm (Geoffrey Moore)

ChatGPT

OpenAI

Claude Code

Lovable

Airtable:

Intercom:

Net Promoter Score

Product Operating Model

Innovator's Dilemma (Clayton Christensen):

The Score Takes Care of Itself (Bill Walsh)

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Connect with Todd:

LinkedIn: https://www.linkedin.com/in/toddolson/

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Connect with Krish:

LinkedIn: https://www.linkedin.com/in/krishs/

X: https://x.com/cbkrish

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra.

In this episode of Second Acts, Krish is joined by Zeb Hermann, General Manager of v0 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.

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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 

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Vercel

Guillermo Rauch

Next.js by Vercel

ShadCN UI

Tailwind CSS

Nikita Shamgunov

Segment

Zhenya Loginov

Sequoia Capital

Miro

Opendoor CEO’s AI memo

Caltech

Harpreet Arora

Malte Ubl

Fluid compute

Fluid compute pricing

Algorithms to Live By (Brian Christian & Tom Griffiths)

Scale (Geoffrey West)

The Long Now Foundation

Magic Patterns

Greedy algorithm

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Connect with Zeb:

LinkedIn

X

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Connect with Krish

LinkedIn

X

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra.

In this episode of Second Acts, Krish is joined by Docebo’s (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.

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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

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Referenced:

Docebo

NASDAQ

Edugo

“From System of Record to System of Intelligence:”

Accenture

Deloitte

Kyle Lacy

Mark Kosoglow

FedRAMP

The Five Dysfunctions of a Team

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Connect with Alessio:

LinkedIn

—

Connect with Krish

LinkedIn

X

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra. Learn more.

In this episode of Second Acts, Krish is joined by Theory Ventures founder and General Partner, Tomasz Tunguz.

Tomasz talks about: the three infinite learning curves that originally drew him into venture, the tricky thing that is advising operators, writing lessons that have made him one of SaaS’s most prolific and admired public thinkers, why he has long believed in the compounding power of distribution, the current case for pursuing uneconomic growth, why pricing is continually in flux, Looker’s extreme PMF and second acts, three reasons why this is the best time in history to start a SaaS business, Umberto Eco, and more.

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Chapters:

(05:22) A walk along Embarcadero

(07:58) Venture’s three infinite learning curves

(09:05) “Advice is a tricky thing”

(11:53) Dalio, Munger, and effective board members

(13:58) Product limited/GTM limited?

(16:00) Situation, Complication, Question, Answer

(19:33) Several short sentences

(21:00) Writing as a way to think better about AI

(23:02) Krish’s fun, clarifying AI use case

(24:51) A distribution-first thesis

(29:38) How AI changes GTM

(32:08) The past and present of category creation

(34:30) The generalist-specialist pendulum

(36:00) “Pricing is a perennial”

(39:09) The inevitability of better AI margins

(41:52) Uneconomic growth as a valid bet

(46:44) Monte Carlo’s radical daily revenue model

(50:34) Never been a better time to start a SaaS business

(54:17) “PMF is grease”

(56:53) The year of Looker 500

(59:07) Why the growth bar keeps moving

(01:00:51) Umberto Eco and explaining China

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Referenced:

Tomasz Tunguz on raising Theory Ventures’ $450 million second fund

The Decade of Data with Tomasz Tunguz

Joel on Software

Poor Charlie's Almanack

Principles by Ray Dalio

Mike Volpi

Tomasz Tunguz on Venture Capital

Intercom

Des Traynor

McKinsey & Company

SCQA

The Second-Order Effects of AI

Several Short Sentences About Writing

Copyblogger

MongoDB

HashiCorp

Google

ChatGPT

Lovable

Cursor

5 Mistakes SaaS Startups Often Make with Pricing

Explore vs. Exploit in Agentic Coding

Barr Moses

How Monte Carlo's Daily Revenue Model Rewrote Their Strategy

The Market Size Mistake

Gainsight

Why There's Never Been a Better Time to Found a SaaS Startup

A Challenge to SaaS Orthodoxy

Extreme PMF : Sustaining Success with Scale

My Favorite Books of 2024

Chronicles of a Liquid Society

Breakneck: China’s Quest to Engineer the Future

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Connect with Tomasz:

LinkedIn

X

Tomasz Tunguz

—

Connect with Krish

LinkedIn

X

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra. Learn more.

In this episode of Second Acts, Krish is joined by Reforge’s founder and CEO, Brian Balfour.


Brian dives into: early years of Reforge’s breakout—“the strongest PMF I’d ever felt”—education business, what led to their recent AI-native second act, launching a whole suite of products within a couple of quarters as a lean team, what real-world enterprise adoption requires, retention laws, the emerging breaking points in the Four Fits to $100m, why AI monetization strains past SaaS growth models and is still being figured out (and why people are wrong about Cursor and others), startup-within-a-startup lessons from HubSpot, Izzy the Inventor, and much more.

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(00:01) Episode intro

(06:24) Second acts aren’t all the same

(08:00) “The most instant PMF I’d ever felt”

(09:35) Whiplash

(10:26) Reforge’s second act

(15:10) “People overbuild for the SV tech company”

(17:56) Unifying the product stack for humans (and AI)

(21:20) How Reforge ships absurdly fast

(24:20) The foundational law of retention

(32:14) What made HubSpot’s seminal second act work

(39:27) How AI is reshaping the Four Fits

(43:35) Why AI monetization breaks traditional SaaS growth

(49:17) Three checks every monetization model must pass

(54:08) How Reforge is pricing multiple AI-native products

(55:28) Why pricing today requires rapid iteration

(58:03) The next great distribution platform

(01:05:48) Capital and the company you want to build (and grow)

(01:10:08) Notes from Brian’s operator reading list

(01:13:04) Storytime: Brian and Krish swap kids’ book recs

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Referenced:

Why Retention Is The Silent Killer

Growth Loops are the New Funnels

AI User Interviewer

Monterey AI

HubSpot

Christopher O'Donnell

Michael Pici

Mark Roberge

The Feedback Fragmentation Tax: How Product Teams Lose Touch (And How To Fix It)

The Foundational Laws of Retention That Haven’t Changed in the AI Era

Calm

Why Product Market Fit Isn't Enough

Four Fits for $100m Growth

Get Out of the ARPU-CAC Danger Zone with Channel Model Fit

tokens are getting more expensive

Cursor

Google: How the Best Business in Human History Happened

The Next Great Distribution Shift

ChatGPT-5

We've Raised $21M To Grow Reforge

Clouded Judgement

Paul Graham

The Coming Wave

Andrew Matthews

Izzy the Inventor (children’s book)

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Connect with Brian:

LinkedIn

X

Brian Balfour

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Connect with Krish

LinkedIn

X

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra. Learn more.

In this episode of Second Acts, Krish is joined by Optimizely’s CEO, Alex Atzberger.

Alex shares notes on: why deeply integrated suites win in enterprise (and will continue to do so with AI), scaling Optimizely into an AI-powered platform (and past $400M+ in ARR), pricing AI agents that span vastly different use cases, treating monetization as a reversible decision, lessons from more than a decade of M&A, building with long-term discipline under PE, hot chocolate, and much more.

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Chapters:

(00:00) Episode intro

(04:45) Lessons from The Wonderbon Chocolate Co.

(09:10) Principles shaping Optimizely today

(12:36) “The suite always wins”

(17:14) Avoiding platform sprawl

(19:56) Defensibility in a world of overlapping suites

(25:00) What are you really pricing for?

(28:46) Pricing is never a one-shot decision

(30:00) Enterprise AI is about the unsexy stuff

(35:35) Test and learn: How Optimizely prices AI agents

(40:35) The hard thinking behind successful M&A bets

(44:44) Building a “long-term healthy” business with PE

(50:20) Team of Teams

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Referenced:

Optimizely

SAP Ariba

The Wonderbon Chocolate Co

"The suite always wins"

"Enterprise AI is not all alike."

"The great bundle brawl (Brian Balfour)"

OpenAI

Optimizely Opal

Insight Partners

Three things I learned from my past five years running a Private Equity owned business

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Connect with Alex:

LinkedIn

—

Connect with Krish:

LinkedIn:

X

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra. Learn more.

In this episode of Second Acts, Krish is joined by Dirk Hoerig, founder of commercetools.

Dirk reflects on: coining “headless commerce” and the architectural decisions that let them stay ahead of wave after wave of platform shifts (including the recent agentic one), standardizing a consumption-based pricing model for wildly varying customer types, having a clear-eyed view of different eras of competition, handing off the CEO title after 14 years (plus scaling past $150m in ARR), staying obsessed with what’s next, and much more.

Dirk: "My experience on building companies and business models is that you have to monetize around what your buyers understand and what's driving value for your business. So you can have a great product that has a lot of customer demands. If your pricing isn't matching what the customer perceives as value driver, and you don't have clear KPIs that they are also able to track, then it will be challenging for you as a business to grow."

Krish: “The [gross margin] discipline that you are referring to—I think is even more applicable in today's world, because with AI, one of the things we are observing is every feature is becoming like a micro-product, and you have to be very conscious of the winners and your fillers... because it's going to cost you a lot more, and it can erode the gross margins.”

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Chapters:

(05:12) commercetools’ early insight 


(06:46) Challenging legacy enterprise commerce vendors that monetized maintenance not innovation


(07:42) Wired magazine’s The Web Is Dead issue (and how it affirmed commercetools’ founding thesis)

(09:45) commercetools today: a composable ecommerce platform that serves every potential touchpoint (including AI agents) 


(10:47) How commercetools defines their enterprise segment

(12:42) 200-item, two-year-old backlogs and the cost of dated enterprise systems 

(19:14) Dirk's monetization philosophy (and why some value drivers remain hard to monetize)

(23:54) How commercetools iterated their way to a standard, order-consumption-based pricing model

(27:23) Conducting rigorous, gross margin analyses across customer tiers

(29:60) How AI features demand a similarly disciplined approach to costs  


(31:55) Building with an unwaveringly counter-intuitive premise; "independent of the category"

(34:45) How a truly API-first architecture has paid off across several—from mobile to voice to agentic—technological shifts 

(41:22) On competition: Legacy giants, segment-expanding players, and the coming AI-native wave

(50:28) A brief snapshot of commercetools’ Commerce MCP launch, from an internal prototype to a standard-defining release 


(57:05) Dirk acknowledges the need to celebrate business milestones better, while there’s always the founder’s urge to move to the next thing 

(59:32) Adapting org design and operating models for serving a sophisticated, at-scale enterprise motion 

(01:03:16) Dirk’s transition to a Chief Innovation Officer role as commercetools prepares for its next decade

(01:08:36) Sports, crunch times, and Dirk’s central advice to founders: “don’t quit” 

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Referenced/Resources:

The Web Is Dead. Long Live the Internet (Wired Magazine)

Why headless commerce will continue to boom after a decade of innovation

Customer Keynote: Path to Composable Commerce - John Lewis Migration Journey

Best Buy

IBM

Salesforce

SAP

Shopify

Introducing the Model Context Protocol

commercetools Commerce MCP

MACH alliance

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Connect with Dirk:

LinkedIn

X

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Connect with Krish:

LinkedIn

X

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra. Learn more.

In this episode of Second Acts, Krish interviews TigerEye’s (previously PlanGrid’s) co-founder and CEO, Tracy Young.

Tracy talks about: her big insights from scaling one of the most formative vertical SaaS businesses (PlanGrid, acquired by Autodesk for $875m), winning with technological shifts (and where she sees TigerEye’s AI-native opportunity), how PlanGrid’s best-in-class pricing model was ultimately outplayed by a now-public competitor, the mid-market “no man’s land”, why to zealously slice TAM when growth stalls, and much more.

Tracy: “I think it’s really easy to increase prices…Changing the shape, and how you charge is much harder. And the reason it’s hard is because you have to look at what percentage of your current revenue that might not renew because of the new pricing. And you always want to protect every dollar of revenue. And that’s the hard trade-off, even if you know this is a better pricing for your customers and for the company.”

Krish: “…It is normally accepted that with scale your growth rate tends to fall. But what you are actually referring to [is] that by deliberately not just looking at an overall business, but slicing it in every dimension, you actually continue to think about the potential in each one of those segments to layer those S curves.”

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Chapters:

(01:06) Episode intro

(03:18) Tracy’s kind, founder-to-founder note of praise

(04:06) TigerEye’s founding premise

(06:58) Why Tracy started PlanGrid (a vertical SaaS pioneer that sold for $875m)

(07:56) Why Tracy chose a horizontal path with TigerEye

(10:10) Reimagining a competitive enterprise category with the AI shift

(12:17) There are (still) at least 10 good startup ideas in every enterprise category

(17:16) Why changing the shape of how you charge is much harder than changing price points

(18:37) How PlanGrid’s exceptionally successful (netting 130-140% NRR) seat-based motion was still bested by a different approach of a now-public competitor

(22:00) Tracy explains how (in the construction space between 2011-20) landing logos faster was more important than the average contract value

(22:55) PlanGrid’s freemium, mobile-SEO driven top of funnel

(23:25) Why Tracy picked a one-price-for-everything (including unlimited seats) for TigerEye

(25:20) How AI allows TigerEye to do things that don’t scale with the depth of best-in-class consulting firms; “insanely fast and at a fraction of the cost”

(28:04) How a painstakingly precise view of segments is critical for understanding where a business is struggling and where it’s headed

(31:40) The “gnarly” data issues PlanGrid encountered post the Autodesk acquisition and how that informed TigerEye

(33:24) Tracy’s three distinct flavours of mid-market (and why the classical definition of that segment fails most founders)

(37:20) Having built SaaS scale-ups in the past decade, Tracy and Krish reflect on the possibilities of building AI-native teams

(42:55) How Tracy sees AI-driven enterprise business models evolving over the next couple of years

(45:00) Why TigerEye is training their own tailored AI models

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Referenced/resources:

American Dreamers: Tracy Young Has The Eye Of The Tiger

TigerEye

PlanGrid

Tracy Young, Co-founder & CEO of PlanGrid (The Social Radars)

YC

Procore

Part II: The failure points from $5m to $100m in ARR

Mid-market is no man’s land

Do Things that Don’t Scale

Cursor

GitHub Copilot

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Connect with Tracy:

Tracy writes

LinkedIn

—

Connect with Krish:

LinkedIn

X

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About Chargebee:

Chargebee helps thousands of recurring revenue businesses unlock second acts of scale with transformative billing, monetization, and growth infra. Learn more.