The ProductLed Podcast is a weekly interview series with both product-led growth leaders and practitioners who have real knowledge to share on what it takes to use their product to grow a business.
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Day 5 of 100: Going Full Ironman Mode on an AI Product
Episode 307
Friday, August 14, 2026 • Duration 27:15
The podcast has been quiet for a couple of months. This episode is why.
I'm building a new AI-first product at ProductLed, in public, over 100 days. It launches November 19th. You'll be able to use it while I build it, and rip it apart, and I'm sharing everything as I go, including the revenue.
Before any of that, I wanted to talk about how I'm going to attack it.
I recently finished a full Ironman. It ends with a marathon, and that's after the 3.8km swim and the 180km bike. Training for it changed the way I take on anything large, and I'm running the same structure on this build. I call it full Ironman mode, and this episode walks through all 16 parts of it.
Some of it is obvious. Most of it is not. The part that surprised me most was standards, because when you look at the standards you set for a goal, they should make the goal inevitable. That is the difference between hoping you finish and knowing you will.
Whatever your next 100 days hold, this should be useful.
IN THIS EPISODE
(04:15) Get crystal clear on your vision
(04:47) Name the core problem you're actually solving
(05:28) Define the end game, and my three success criteria for this build
(07:42) Tap your network for people who have already done it
(08:54) The identity shift, and the line I write every morning
(10:35) Pick the date
(11:39) Why one why is never enough
(12:53) Get a coach or an advisor
(14:37) Create space, and audit what pulls you away
(17:40) Find peers in the trenches
(18:50) Name the price you're willing to pay
(19:54) Resources are accelerants
(20:48) A daily plan you don't have to think about
(22:09) Standards that make the goal inevitable
(23:05) A reward you only get if you finish
(24:57) Write your own rules
MENTIONED
Conquer 100, the documentary about the Iron Cowboy
Mickey Allen, CEO at Foldspace, advising on this build
What's your next 100 days going to be? Let me know.
From 10 Failed Products to a $1M/Month SaaS Portfolio
Episode 306
Tuesday, June 16, 2026 • Duration 52:33
After spending years building unvalidated products that went nowhere, Tibo Louis-Lucas completely changed how he approached startups. In this episode of the ProductLed Podcast, he shares how those early failures pushed him toward a faster, revenue-first way of building, one that eventually led to the success of Tweet Hunter and Taplio, and now powers a growing portfolio of product-led SaaS businesses.
Tibo breaks down why revenue is the only validation that really matters, how Tweet Hunter stood out in a crowded market by going deep on a single platform, and the unusual distribution playbook that helped it take off. That included giving a major profit share to a creator-partner and building a network of “creative investors” who amplified the product from day one.
The conversation also dives into why selling a company was far less glamorous than it sounds, and why Tibo now prefers building and holding long term. He shares how he thinks about creating an “indie hacker stack” for a specific persona, how AI has changed his day-to-day workflow, and why he now spends less time coding and more time reviewing, iterating, and building systems.
One of the biggest takeaways is his operating style: no calls, fast feedback loops through DMs, and a strong focus on staying close to paying users. For founders building product-led companies, this episode is packed with practical lessons on validation, distribution, focus, and building with speed in the AI era.
Key Highlights:
02:21 - Why Two Failed Startups Changed Everything
Tibo shares the painful lesson of spending years on unvalidated ideas, and how that pushed him to become relentlessly validation-driven.
05:38 - Revenue Is the Only Validation That Counts
Why free users can be misleading, how Tibo evaluates startup ideas today, and what made Tweet Hunter feel different almost immediately.
09:47 - How Tweet Hunter Won a Crowded Market
The strategy behind focusing on one platform deeply, serving creators instead of enterprises, and building something clearly better for a narrower use case.
No Sales Call Required: Roeland Delrue on Scaling Aikido to a Cybersecurity Unicorn
Episode 305
Tuesday, May 26, 2026 • Duration 53:01
In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Roeland Delrue, CEO and co-founder of Aikido Security, to unpack how the company reached $40M+ ARR in just three and a half years in one of the most sales-heavy categories in software.
Roeland shares how his team entered cybersecurity without a traditional security background, simply by living the problem themselves. After juggling eight different security tools and watching a security engineer quit from the sheer pain of triaging endless false positives, they decided to build the product they wished existed.
The conversation digs into why Aikido took a radically product-led path in a market dominated by demos, gated trials, and opaque pricing. Roeland explains how transparent pricing, fast time-to-value, and a no-nonsense buying experience helped Aikido win trust with developers and security teams alike.
They also get into the bigger growth story behind the business: why product-led motions scale so well, how compliance trends like SOC 2 create strong tailwinds, and why Aikido chose to build a multi-product platform from day one instead of another point solution.
Toward the end, Roeland shares his view on AI in cybersecurity, where AI pen testing is already replacing human work, and where humans will still matter for a long time. It is a candid look at building a category-defining security company without following the usual playbook.
Key Highlights:
01:46 - The Pain That Sparked Aikido
How Roeland and his co-founders went from frustrated security-tool buyers to building their own solution.
04:40 - Why Cybersecurity Needed a PLG Rethink
The Mutiny Pivot: Why Jaleh Rezaei Shut Down an 8-Figure SaaS to Go All-In on AI
Episode 304
Friday, May 15, 2026 • Duration 49:57
In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Jaleh Rezaei, co-founder and CEO of Mutiny, to unpack one of the boldest founder moves you’ll hear this year.
After building Mutiny into an eight-figure ARR SaaS company, Jaleh made the rare decision to shut down most of the original business and rebuild around AI agents. She shares why trying to run both a traditional SaaS company and an AI-native company at the same time created constant friction, slowed the team down, and made it impossible to move at the pace the market demanded.
Jaleh walks through how she made the call, what gave her confidence to follow through, and what the first 90 days of the pivot actually looked like. That includes shrinking the team, moving to a smaller in-person setup, carefully migrating customers, and rebuilding company culture around speed, customer obsession, and founder-level context.
The conversation also dives into why Mutiny shifted from sales-led to product-led growth, how self-serve products expose weaknesses faster, and why “showing” value beats explaining it, especially in AI. Jaleh also shares her view on what still counts as defensible in AI, why experience generation and analytics matter more than basic data movement, and how she personally uses AI across recruiting, meeting prep, and writing support.
It’s a candid look at conviction, timing, and what it really takes to rebuild for the next wave.
Key Highlights:
01:41 - Why She Left 8-Figure ARR Behind
Jaleh explains why combining a SaaS business with an AI-native business created roadmap, pricing, and execution conflicts that made a harder pivot inevitable.
$5M ARR, 2 People, $100M Exit — How Jeremy Clarke Did it, and What He is Building Next
Episode 303
Friday, May 8, 2026 • Duration 54:50
Most founders hear stories about lean SaaS companies and assume they are the exception.
Jeremy Clarke lived one.
In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Jeremy Clarke, founder of WebMerge and now the builder behind Quin, to unpack what it really took to grow WebMerge into a multi-million dollar business with an incredibly small team.
Jeremy shares how WebMerge started as a simple PDF generation tool, why integrations became the growth engine that unlocked scale, and how a strategic hire helped expand distribution without bloating the company. He also gets honest about what has changed in today’s AI market: thinner margins, tougher distribution, less generous free plans, and far more noise.
The conversation also dives into the founder mindset behind building highly effective companies. Jeremy explains why staying close to support made WebMerge stronger, why he delayed hiring for as long as possible, and what drove his decision to eventually sell. From there, he opens up about building Quin, what it means to compete in a crowded AI category, and why word of mouth and customer trust still matter more than ever.
If you want to build a meaningful software business without defaulting to a big team or venture funding, this episode is packed with practical insight.
Key Highlights:
00:43 - From WebMerge to Quin
Jeremy shares what he’s focused on today, why Quin is a much harder business to build than WebMerge, and how AI margins change the game.
07:36 - The WebMerge growth playbook
How WebMerge evolved from a simple PDF tool into an integration-driven platform, and why partnerships became a major distribution engine.
Built on a Crisis: Jeff Wang on Winning Enterprise AI Coding with Windsurf
Episode 302
Friday, April 24, 2026 • Duration 36:17
When Jeff Wang stepped into the CEO role at Windsurf, it was not part of some long-term succession plan. It happened in the middle of a full-blown crisis.
In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Jeff to unpack the wild chain of events that followed the collapsed OpenAI acquisition, the founders leaving for Google, and the intense 72-hour window Jeff had to help save the company and protect 250 jobs. He shares how Windsurf navigated that moment, how the Cognition deal came together, and what it has been like leading one of the most closely watched teams in AI coding ever since.
Jeff also gets into what made Windsurf so strategically valuable in the first place, from shipping early breakthroughs in autocomplete, chat, context engineering, and agent workflows, to building one of the first generally available coding agents on the market. Beyond the origin story, the conversation goes deep on go-to-market strategy, why free products worked early on, how token economics changed the game, and why enterprise AI adoption takes far more than handing teams a tool.
They also explore Windsurf 2.0, the shift toward managing multiple agents at once, how Jeff uses AI in his own CEO workflows, and why founders need to obsess over painful problems, customer conversations, and product-market fit instead of flashy demos.
Key Highlights:
00:00 - The 72-Hour Crisis That Changed Everything
Jeff shares the short version of the OpenAI, Google, and Cognition saga, and what it was like stepping into the CEO role during a company-defining emergency.
01:40 - Why Big Tech Wanted the Windsurf Team
A look at the execution speed, product breakthroughs, and agent innovations that made Windsurf one of the most valuable teams in AI coding.
04:10 - The Future of Coding Is Multi-Agent
Jeff explains why developers are moving from one-on-one AI assistance to managing many agents at once, and how Windsurf 2.0 is built for that shift.
From Feature Flags to AI Runtime Control: The LaunchDarkly Story
Episode 301
Thursday, April 9, 2026 • Duration 34:08
In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Edith Harbaugh, CEO and co-founder of LaunchDarkly, the feature management platform used by more than 5,000 customers, including 25% of the Fortune 500.
Edith shares how her experience at TripIt led to the insight behind LaunchDarkly, and why feature management became such a critical part of modern software delivery. She explains what it actually took to create a category in the early days, when many companies were still shipping software only a few times a year, and why listening to customer pain mattered more than trying to force a new movement on the market.
The conversation also dives into LaunchDarkly’s unusual balance of product-led and enterprise sales, why the company kept its free tier even as it grew upmarket, and the story behind its first real enterprise deal. Edith also opens up about returning as CEO, how AI is reshaping software delivery, and why she now sees LaunchDarkly as runtime control for the AI era.
One of the biggest themes throughout the episode is Edith’s leadership philosophy: work should be fun. For her, that means helping teams reduce toil, build better software, and stay connected to the real impact they have on customers.
Key Highlights:
01:59 - What Feature Management Actually Does
Edith breaks down feature management in simple terms, from beta rollouts and experimentation to location-based access and safe runtime control.
03:09 - The TripIt Insight Behind LaunchDarkly
How constant mobile and backend releases at TripIt revealed a problem most software teams still had not solved.
04:47 - How to Create a Category People Want
Edith explains why category creation was much harder than it looked, and how meeting customers where they were helped LaunchDarkly gain traction.
ChartMogul, AI, and the Future of SaaS Growth
Episode 300
Friday, April 3, 2026 • Duration 49:30
In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Nick Franklin, founder and CEO of ChartMogul, to talk about what is really happening in SaaS right now.
Nick shares what he is seeing across 3,000+ subscription businesses and why the last three years have been the most disruptive period in SaaS history. He explains why AI startups are still buying traditional SaaS tools, why subscription pricing is far from dead, and how customer expectations have changed fast. Faster time to value, more functionality, and lower prices are now the baseline.
The conversation also gets into how ChartMogul is adapting. Nick talks about their move into CRM, why combining revenue analytics with customer context creates new opportunities, and how AI can unlock deeper insights from complex subscription data. He also responds to the big question facing analytics companies today: if LLMs can query data directly, what role does a platform like ChartMogul play?
Beyond strategy, Nick shares a grounded view on moats, competition, and what actually matters most in building a durable SaaS company. His answer is refreshingly simple: build a great product, charge fairly, support customers well, and keep improving every day.
It is a thoughtful conversation on SaaS survival, product strategy, and what it takes to stay relevant in an AI-first world.
Key Highlights:
02:43 - AI Startups Are Still Buying SaaS
Nick shares one of the more surprising trends from ChartMogul’s customer base. A big share of new customers are AI startups, and many of them are still using classic subscription pricing.
03:53 - Why SaaS Has Had Its Hardest 3 Years
Nick explains why the last few years have been so tough for SaaS, from the post-COVID reset to higher interest rates and tighter funding.
The GPU Gold Rush: How Vast.ai Scaled With AI Demand
Episode 299
Friday, March 27, 2026 • Duration 41:57
In this episode of the ProductLed Podcast, Wes Bush and Esben Friis-Jensen sit down with Travis Cannell, CEO and first employee at Vast.ai, the marketplace for on-demand, low-cost GPUs powering AI workloads around the world.
Travis breaks down one of the biggest shifts happening in AI right now: the rise of inference. He explains why inference demand is exploding, how that shift is fueling Vast.ai’s rapid growth, and why more teams are looking for flexible, affordable GPU access outside of traditional cloud platforms.
The conversation also gets into how Vast.ai built a two-sided GPU marketplace with 20,000 GPUs, why its pricing model creates powerful marketplace dynamics, and what makes its software-first approach difficult to replicate. Travis shares how the company thinks about competition, customer support, GPU hosting economics, and why winning in a fast-growing marketplace depends on much more than just low prices.
They also explore how AI is changing org design inside high-growth companies. Travis talks candidly about pausing hiring, using AI to accelerate engineering work, and why Vast.ai has leaned into an in-office culture while staying extremely lean.
If you want a clearer picture of where AI infrastructure is heading, and how one company is scaling quickly with a software-first model, this episode is packed with insight.
Key Highlights:
02:34 - Why Inference Is Fueling the Next AI Boom
04:15 - Inference Explained in Plain English
06:15 - The Moment Vast.ai Hit Hypergrowth
10:04 - Why Teams Choose Vast Over AWS
12:34 - Building a Two-Sided GPU Marketplace
17:03 - Competing on More Than Just Price
18:52 - The Real Economics of Hosting GPUs
25:21 - The Network Effects Behind Vast.ai
31:31 - Building a Lean Team During Hypergrowth
36:09 - Why AI Changed Their Hiring Strategy
Resources:
🚀 Vast.ai: Marketplace for low-cost GPUs:
The Evolution of Product-Led Growth: PLG x AI
Episode 298
Saturday, March 21, 2026 • Duration 15:39
In this episode, Wes breaks down how PLG is evolving and why the fastest-growing AI companies are still using it, just with a completely different playbook. The old model was about reducing friction. The new model is about doing the work for the user.
It starts with Shutterstock, a company that had PLG nailed for years. But once AI image generators arrived, everything changed. Users no longer wanted to browse and compare endless options. They wanted to type what they needed and get the result instantly. That same shift is now reshaping software everywhere.
You’ll also hear examples like Google Slides vs. Gamma, Stack Overflow vs. Cursor, and Westlaw vs. Harvey, where AI-native products are not just easier to use. They are taking on more of the actual work.
The episode also breaks down the three versions of PLG. PLG 1.0 is built for builders. PLG 2.0 is powered by AI and built for editors. PLG 3.0 goes even further, with agents completing work on the user’s behalf. As products move through these stages, time to value drops and market potential grows.
If you are building a product-led company, this episode will challenge how you think about growth, user expectations, and what it takes to win in an AI-first market.
Key Highlights:
0:00 - Why PLG is evolving
0:19 - The Shutterstock example
1:24 - From reducing friction to doing the work
1:32 - Google Slides vs. Gamma
2:23 - Stack Overflow vs. Cursor
2:39 - Westlaw vs. Harvey
3:23 - The three versions of PLG
4:32 - What defines PLG 2.0
5:24 - How AI expands TAM
7:53 - What PLG 3.0 looks like
11:03 - Which version are you building for?
12:11 - The Distribution Deal That Fueled Growth
How Tibo partnered with influencers using profit share and exit incentives, and why aligning distribution with the product was such a powerful lever.
15:25 - The Creative Investors Growth Engine
Why he gave small ownership stakes to 17 creators, how that amplified launches and updates, and what made the model work.
19:31 - Why Selling Wasn’t the Dream Outcome
Tibo opens up about the pressure of earnouts, platform risk, and why the acquisition experience made him want to build and hold instead.
23:46 - Building an Indie Hacker Software Stack
Why Tibo organizes his portfolio around a specific persona instead of a single vertical, and how he thinks about expanding from five products to more.
34:54 - No Calls, More DMs, Better Feedback
A look at his no-meeting policy, why DM-based customer conversations work so well for him, and how staying close to users improves product decisions.
37:18 - How AI Changed the Way He Builds
Tibo explains how AI emptied his backlog, turned him into a QA-first builder, and created a new challenge: resisting feature creep.
How she built conviction for a risky decision, what made “moving as fast as possible” the real north star, and the advice she gives founders facing the same choice.
11:13 - Reframing the Pivot as Mission, Not Failure
Why walking away from a successful product did not feel like giving up, and how first-principles thinking helped her reconnect the company to its original vision.
15:05 - The First 90 Days of the Transition
A behind-the-scenes look at shrinking the team, getting back to a small in-person setup, and creating the conditions needed to find product-market fit again.
17:01 - How Mutiny Migrated Customers Gracefully
The detailed playbook for protecting customer trust during the transition, from partner selection and pricing negotiations to white-glove migration support.
23:03 - Building a Team for Startup Intensity Again
How Jaleh thought about team size, in-office culture, and the level of intensity required to compete in the current AI market.
25:58 - What Founders Must Stop Delegating Pre-PMF
Why founders need direct exposure to customer calls, onboarding, pricing conversations, and product friction if they want to move fast and make better decisions.
32:12 - Why the New Mutiny Had to Be Product-Led
Jaleh shares why self-serve makes products better, how AI products benefit from instant hands-on proof, and why PLG also improved the sales-led motion.
40:22 - What a Real AI Moat Looks Like
Her take on defensibility in AI, why simple data workflows will get commoditized, and why Mutiny is focused on experience generation, analytics, and self-improving systems.
45:15 - Jaleh’s Highest-Leverage AI Workflows
The practical ways she uses AI today across recruiting, meeting prep, and writing optimization, plus why she still believes strong writing needs a human point of view.
From free autocomplete to on-prem enterprise deals, Jeff walks through Windsurf’s early PLG motion and how it created awareness and pipeline.
13:10 - The Hard Truth About AI Pricing
A candid discussion on token costs, self-serve subsidies, pricing pressure, and why raising prices can reveal whether you truly have product-market fit.
16:13 - Why Enterprise AI Sales Are Top-Down
Jeff shares how Windsurf sells into large companies by focusing on transformation, adoption, security, and measurable outcomes instead of seat counts.
20:51 - What It Takes to Drive Real AI Adoption
Why playbooks, training, and solving a meaningful first use case matter more than just rolling out a shiny new tool to an engineering team.
24:40 - Jeff’s AI Workflows as CEO
Jeff reveals how he uses AI and custom playbooks for go-to-market research, outreach preparation, and spotting product trends before opening dashboards.
32:32 - Jeff’s Advice for Every Product Founder
Build around painful problems, talk to hundreds of prospects, and learn to enjoy rejection because that is often where the real insight comes from.
Wes and Nick unpack how buyer expectations have changed. SaaS products now need to deliver more value, reduce friction, and help customers get results much faster.
10:45 - Why ChartMogul Went Multi-Product
Nick breaks down the move into CRM and why bringing together revenue analytics, customer history, and interactions creates a much stronger product.
12:35 - How AI Can Unlock Deeper Analytics
Rather than replacing analytics tools, Nick sees AI as a way to help customers get more value from complex data through more natural questions and faster insight discovery.
15:25 - Can LLMs Replace Subscription Analytics Tools?
Wes pushes on the biggest threat facing analytics platforms, and Nick explains why clean data, normalized metrics, domain expertise, and strong tooling still matter.
21:25 - Why Vibe Coding Won’t Replace SaaS
The team talks about why most founders should use AI to speed up their own roadmap instead of trying to rebuild products like Slack, Notion, or HubSpot internally.
26:28 - Moats, Benchmarks, and the Bloomberg of SaaS
Nick shares how ChartMogul thinks about defensibility through benchmarking data, expert-led content, partner networks, and long-term trust.
33:39 - The New “Wow” for Analytics Products
Nick talks about why basic metrics are no longer enough, what customers expect now, and how ChartMogul is thinking about creating more signal and insight.
46:16 - What Keeps Nick Building After 10+ Years
To close, Nick reflects on why he is still building, what gives the work meaning, and why creating something lasting matters more than chasing an exit.
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