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)

—

Connect with Brian:

LinkedIn

X

Brian Balfour

—

Connect with Krish

LinkedIn

X

—

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

—

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

—

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

—

Connect with Krish:

LinkedIn

X

—

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.”

—

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

—

Connect with Tracy:

Tracy writes

LinkedIn

—

Connect with Krish:

LinkedIn

X

—

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 (a first for season two; welcome back!), the table turns as Krish is interviewed by Chargebee’s CMO, Guy Marion.

They talk about: Chargebee’s founding theses, strengths, and constraints, *the* characteristic patterns (not to be found in “innovation labs”) that propel second acts, how pricing of AI products must draw on familiar monetization principles yet demand a markedly different view of costs and value, the baffling absurdity of once-a-year pricing changes, Krish’s introspections on “inspired problems” and scaling himself, billing for time travellers, and much, much more!

Krish: “The good news is you have so much data [on pricing]. Which you can use to be more precise about it or understand it and then being able to make much better decisions where it’s no longer an art. It can be a science, provided you’re leaning into wanting it to be a science.”

Guy: “I think that's one of the differentiators of founder-led businesses still is that… beginner’s mindset where you're looking at every problem, looking at how to improve it in an honest and transparent way.”

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Chapters:

(03:43) How Krish described Chargebee’s mission five years ago (and where it’s headed now)

(05:54) On billing’s expansive, transformative role in an AI-driven world 

(08:03) How AI is changing the value exchange question 

(10:17) How a customer-first approach to growth shaped Chargebee’s early years

(13:34) How founding strengths continue to inform Chargebee’s approach to products

(16:00) Stacking S-curves (or defining second acts of scale) 

(17:52) The defining characteristic of companies that get second acts right 

(23:10) Krish reflects on the founder’s journey and scaling himself

(28:55) On founder mode and what the current, uncertain moment demands 

(32:57) How each era of software has been driven by the core economics of delivery 

(36:12) Why the urgency around AI innovation is fast shifting towards urgency around monetizing that innovation 

(39:12) Why treating pricing as a science is central to enduring businesses

(41:53) Why the future of software monetization is hybrid (and still driven by a standard evolution of the value chain) 

(45:19) Why AI monetization is still rooted in pricing fundamentals 

(46:55) The table-stakes instrumentation that modern monetization demands

(49:01) Why monetization experiments can no longer be a once-a-year exercise

(52:31) How Zapier, Personio, and other Chargebee customers solve pricing with rapid iteration  

(55:10) Why monetization has been an underutilized growth lever 

(56:25) The “Partner > Build > Buy” M&A framework (and applying that to Chargebee’s own product bets)

(01:02:41) An API-first approach to everything; or why Chargebee built a time machine 

(01:05:07) Creating an environment for scaling people’s contributions (also: their lessons, challenges, and happiness)

(01:10:17) Where “inspired problems” come from 

(01:15:57) Krish’s move to Amsterdam and on the beautiful gains of operating in a globally distributed org 

(01:19:47) The role of luck in the scaling journey 

(01:22:51) Guy’s closing note  

—

Mentioned/Resources:

Invisible asymptotes

Joel on Software

Girish Mathrubootham

Second Acts; Episode 1: Nick Mehta, Gainsight

The Dream Machine

Wardley map

Zapier

Personio

DeepL

Hostinger

Chargebee Time Machine

Moments of Truth

Rajaraman Santhanam

—

Connect with Guy:

LinkedIn

—

Connect with Krish:

LinkedIn

X

—

About Chargebee:

Chargebee is a Revenue Growth Management platform that helps thousands of recurring revenue businesses unlock second acts of scale. Learn more.

In this episode of Second Acts, Krish is joined by Guru’s co-founder and CEO, Rick Nucci.

Rick recounts how they rediscovered product-market fit at his previous startup, Boomi (the first iPaaS that foresaw cloud’s preeminence, exited to Dell, and was last valued at $4b), the many evolutions of Guru’s all-in-one (AI Search + Intranet + Wiki) position, three principles for building in an AI-first enterprise world, how they’ve thought through pricing experiments that serve both PLG and SLG motions, and much more!

Rick: “We put an enormous amount of effort into listening to the market. And I would say 80% of listening to the market for us means listening to all active customer conversations. We certainly look at and understand what competitors are doing. I think that’s very important. I think it’s especially important these days. [With] AI there [are] constant new entrants and so you really do need to spend time and be aware of them. That pendulum can over-swing though and I think where it can become unhealthy is if you lose your North Star of what you’re doing and what your purpose in the world is, so we do try to balance that carefully.”

—

(03:57) Charting Guru’s evolution as a product

(11:30) How Boomi (Rick’s previous venture) bet big on the cloud transition and differentiated against MSFT and other well-funded giants

(14:32) Connecting a huge problem with a [new] technology, a clear need, and a first mover’s advantage

(17:18) How (much) Rick and team think about competition

(18:06) Guru’s relentless customer listening rituals to keep levelling up in a competitive space

(21:02) A customer-first ritual Krish is trying to bring back and his favourite internal Slack channel

(22:35) How Guru serves customers of different sizes with a core product insight and 2 GTM motions

(27:36) Moving to a company-wide problem from departmental problems — The 3 arcs of Guru’s product-market fit

(34:20) How Guru’s path reminded Krish of Chargebee’s own opportunities and challenges

(36:24) Lessons from Guru’s old, short-lived pricing experiment

(38:51) Why Guru’s current pricing model is framed around a “dead-simple” price-point that serves an all-in-one package

(40:20) How Rick and team empower themselves to make pricing changes

(41:30) How pricing is a compass for continuously finding the right customers

(43:25) “Focus on outcomes, not algorithms” and other notes on making sense of the AI hype cycle

(49:35) Krish’s experience of the great possibilities of AI-first interfaces

(51:15) “It’s possible to have a culture of urgency that doesn’t burn people out”

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Mentioned/Resources:

Dell Discovers Internet Mojo in … Philadelphia?

The GURU of Philly Tech: CEO Rick Nucci

What AI means for the future of SaaS: Reality vs. hype

“We recently had our 100th Townhall at Guru. This is one of my favorite rituals…”

“Guru turned 10 this week…So, here are 10 learnings from the last 10 years…”

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Connect with Rick:

X

LinkedIn

Connect with Krish:

X

LinkedIn

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Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this episode of Second Acts, Krish speaks with Copado’s CEO, Ted Elliott.

Ted shares (with refreshing wit and candor): the pivots that defined Jobscience (the previous business he helmed for 18 years), a veteran’s view of building and scaling software (Copado has raised over $300m for its DevOps platform) within the Salesforce ecosystem, what causes M&A disasters, Mungerisms, and much more.

Ted: “What caused the disaster acquisitions? Lack of alignment. Lack of having the same interests. Lack of wanting to be here for the long game to make it happen. You really cannot acquire…If you want to acquire a businesses because they are cheap and you think you can just pick up something on the fly and press them in a box you should be a private equity firm. When you’re a growing venture-backed business, you’re doing acquisitions to get bigger faster, to get some innovation you couldn’t build…”

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Chapters:

(02:57) An introduction to Copado

(04:32) A brief snapshot of Ted’s path before Copado

(05:16) The 3 kinds of pivots that shaped Jobscience (Ted’s previous, 18-years-in-the-making bootstrapped venture)

(06:44) “…you really never want to burn bridges”

(08:09) A heart-to-heart on the peculiarities of (startup) time and life itself

(11:45) Learning to balance “founder mode” style involvement by scaling “people, processes, and products”

(17:22) Why Ted believes Salesforce is still largely misunderstood as a cloud platform

(22:26) How Copado’s grasp of the Salesforce ecosystem has helped them spot a compelling gap

(23:22) The 3 stages (one being the “Valley of Death”) of building on Salesforce

(26:18) Why opportunistic, financials-driven M&A deals don’t work for mission-driven, high-growth companies

(32:37) Remembering a Mungerism: “Tap dancing to work”

(33:47) Working with a massive platform? Know your swim lanes

(37:19) Why Ted hires for “speed of trust” and how he decided on leading Copado

(43:44) Hiring a CFO early and 2 other impactful decisions Ted made in his first year as Copado’s CEO

(46:38) A talent insight Ted realized while working with his father

(49:27) Taking away the right (hard) lessons from this down cycle

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Mentioned/Resources:

Copado Celebrates 10 Years of DevOps for Enterprise SaaS Solutions

Meet the CEO of a Salesforce DevOps $1B Unicorn [Interview]

Ted Elliott of Copado: I Survived Cancer and Here Is How I Did It

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Connect with Ted:

X

LinkedIn

Connect with Krish:

X

LinkedIn

—

Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this episode of Second Acts, Krish is joined by Jellyfish’s co-founder and CEO, Andrew Lau.

Andrew begins the conversation with a modest admission: "Part of this is the entrepreneurial journey, probably a little impostor syndrome (we’re not done yet)... it’s hard to draw a line or make declarations around things definitively working or not. But I’m excited to share what we’ve done if that’s helpful for others to learn from along the way."

But, with stints at Microsoft and IBM in the late 90s, being an engineering leader at a startup (Endeca) that turned into a billion-dollar exit, and multiple ventures of his own under his belt, Andrew's discerning lessons cut across different eras of SaaS.

He revisits standard “binaries” (PLG vs enterprise, saturated vs white-space categories, and founders vs markets) and illustrates how a nuanced understanding of each of those and 25 years of common context with his co-founders have helped shape Jellyfish’s scaling path.

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Chapters:

(02:50) “We’re not done yet”

(03:18) An introduction to Jellyfish 

(05:02) Why startups are the by-products of founders’ experiences

(07:09) How Andrew and his co-founders arrived at Jellyfish’s core thesis and values with 25 years of shared context 

(16:17) The quiet, services-mindset-informed early years of Jellyfish 

(21:59) Choosing a GTM motion — why they decided against both an SMB-first, PLG play and a seven-figure, enterprise play

(27:59) The foundations that allowed Jellyfish to accelerate during the pandemic 

(29:39) Creating a category vs picking a mature market — “People think that something like Salesforce is preordained, it’s not” 

(33:45) Figuring go-to-market operations as technical founders 

(39:53) Managing reserves of capital and patience to address the inherent unpredictability of markets

(46:15) Understanding central forecasting levers as a way to unlock next acts of growth 

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Mentioned/Resources:

Jellyfish aims to ‘do for engineering what Salesforce did for sales’

Navigating 2024: Engineering management principles to tackle the unknowns & challenges ahead

How to Translate Engineering to the CEO

MGMT Boston - The Endeca Effect - Special Report (1/5)

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Connect with Andrew:

LinkedIn

Connect with Krish:

LinkedIn

X

—

Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

In this episode of Second Acts, Krish is joined by Crossbeam’s co-founder and CEO, Bob Moore. Bob traces a captivating line of inflection points across the three different SaaS startups (RJMetrics; acquired by Magento, Stitch; acquired by Talend, and Crossbeam; they recently acquired their biggest, most kindred-spirited competitor, marking a major second act) he has co-founded. In doing so, he also expounds — with lively analogies — on the line that ties product-market fit and breakthrough scale.

Bob: “I will say, shamelessly, that being a repeat founder is an extreme cheat code to having a short-cut to product-market fit. Because not only do you have a lot of very real, tactile experiences inside of an operating company to pull from that give you a lot of conviction around your idea, not just in academic theory, which is what we came to the table with at RJ[Metrics]. But, actually, in practice, based on real-world interactions with real companies. You get that head start. But then, you also have relationships.”

—

Chapters:

(03:20) Falling out of PMF (despite a glorious head start) with RJ Metrics

(15:12) “2 ways to make money in business: One is to bundle; the other is unbundle.”

(18:56) Why Bob thinks being a repeat founder is an extreme cheat code for PMF

(25:34) How Stitch and Crossbeam came about in quick, high-energy succession

(30:32) How ecosystem signals can unlock the stacking of next S-curves

(35:22) Why taking ecosystem-led growth beyond the partnerships team is a force multiplier

(42:42) Bob’s earnest reflection on raising “pandemic-fuelled” mega rounds of capital

(47:12) How the Crossbeam-Reveal merger is shaping their future second acts

(55:45) The fantastically similar paths that brought Bob and Simon (Reveal’s co-founder) together

(58:05) “Suffer pain early” — Why Bob feels M&As are set up to fail and how he has approached them

(01:04:44) How poker and improv have deeply informed Bob’s sense of the core binaries of starting up

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Mentioned/Resources:

I’m Bob Moore. I’m the CEO and Co-founder at Crossbeam, and a serial SaaS founder, AMA!

My $2.6 Billion Ecosystem Fail

How to Succeed in Business by Bundling – and Unbundling

Breaking: Stitch acquired by California-based Talend in $60M deal

Whoa: RJMetrics just got acquired

It’s Happening! Crossbeam and Reveal are Joining Forces to Disrupt Go-To-Market Strategy As We Know It

This Founder Built Startups in 2008, 2016 and 2018. Here’s What He’s Learned About Resiliency

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Connect with Bob:

LinkedIn

Twitter

Connect with Krish:

LinkedIn

Twitter

—

Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.