What happens to the internet when robots act like humans?
Ryan welcomes WPEngine CTO Ramadass Prabakar to the show to chat about what happens—and what we should do—when agents start acting like humans online, how our internet is evolving to serve both human and agentic experiences from the same interface, and what we can do to differentiate and protect human actions online from malicious bot activity.
Episode notes:
WP Engine hosts and manages over 5 million WordPress sites, combining enterprise-grade software, developer tools, and cutting-edge AI to support your website.
Connect with Ramadass on LinkedIn or Twitter.
Congrats to user Nama on winning a Famous Question badge for asking how to store the spinner values into database?
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Episode 817 | Bootstrapping in the Age of AI with Jason Cohen
How would a 2x unicorn founder build his next startup with AI?
In this episode, Rob Walling sits down with Jason Cohen, founder of SmartBear and WP Engine, to talk about building billion-dollar businesses, the future of AI for founders, and what makes small companies thrive even when the odds are stacked against them.
They dig into the early days of WP Engine, how Jason develops his frameworks, why execution beats ideas, and Jason’s framework for identifying “hidden multipliers” small, systematic changes that make an outsized impact.
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Topics we cover:
(03:45) – The core idea behind Hidden Multipliers
(09:24) – Writing as a way of thinking
(12:34) – Why sharing your frameworks matters
(14:14) – The origin of “Designing the Ideal Bootstrap Business”
(18:10) – The hidden weak links in every startup
(21:25) – De-risking and niching down effectively
(24:56) – Why narrowing your focus expands your reach
(26:24) – Building WP Engine in a commodity market
(29:37) – Out-executing funded competitors
(31:52) – Finding product–market resonance through pricing
(32:40) – How brand actually develops
(37:54) – Building in the age of AI: pitfalls and opportunities
(41:52) – The three categories of AI startups today
(46:02) – Why 10x improvement is the new baseline for differentiation
(49:19) – The real moat in the age of AI
Links from the Show:
MicroConf US 2026 – Portland, April 14–16, 2026 Promo Code: Rob50 for $50 off
The SaaS Playbook
PREORDER Hidden Multipliers by Jason Cohen
Designing the Ideal Bootstrapped Business with Jason Cohen
A Smart Bear Blog
Jason Cohen (@asmartbear) | X
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
Subscribe & Review: iTunes | Spotify
5 questions to ask when your product stops growing | Jason Cohen (2x unicorn founder)
Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team.
We discuss:
1. Jason’s five-step framework: logo retention, pricing, NRR, marketing channels, target market
2. A small tweak that’ll double response rates on your cancellation surveys
3. Why “it’s too expensive” is almost never the real reason customers cancel
4. The “elephant curve” of growth
5. How repositioning the same product can increase revenue 8x
6. When to reconsider if growth is even the right goal for your business
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Brought to you by:
10Web—Vibe coding platform as an API
Strella—The AI-powered customer research platform
Brex—The banking solution for startups
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Episode transcript: https://www.lennysnewsletter.com/p/why-your-product-stopped-growing
—
Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Jason Cohen:
• Preorder Jason’s book: https://preorder.hiddenmultipliers.com/
• X: https://x.com/asmartbear
• LinkedIn: https://www.linkedin.com/in/jasoncohen
• Blog: https://longform.asmartbear.com
• Website: https://wpengine.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Jason Cohen
(05:19) Jason’s writing journey
(08:25) Questions to ask when your product stops growing
(18:17) Getting real customer feedback
(20:27) Analyzing cancellation reasons
(26:54) Onboarding and activation
(29:35) Quick summary
(35:46) Revisiting pricing strategies
(41:46) Positioning strategies
(47:52) Why pricing is inseparable from your strategy
(52:06) The importance of net revenue retention (NRR)
(01:00:25) Asking whether or not this is good for the customer
(01:04:34) Leveraging existing customers
(01:06:42) Are your acquisition channels saturated? The “elephant curve”
(1:09:41) Why all marketing channels eventually decline
(01:12:04) Direct vs. indirect marketing channels
(1:13:36) Getting creative with new channels
(01:19:04) Do you actually need to grow?
(01:25:57) Deciding when to quit
(01:29:27) Book announcement
(01:33:21) AI corner
(01:34:35) Contrarian corner
(01:37:43) Lightning round and final thoughts
—
Referenced:
• Tyler Cowen’s website: https://tylercowen.com
• How to Perform a Customer Churn Analysis (and Why You Should): https://www.groovehq.com/blog/learn-from-customer-churn
• Linear: https://linear.app
• Jira: https://www.atlassian.com/software/jira
• Patrick Campbell’s post on X about pricing: https://x.com/Patticus/status/1702313260547006942
• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan
• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam
• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy
• M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs): https://www.lennysnewsletter.com/p/m-and-a-competition-pricing-and-investing
• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr
• Buffer: https://buffer.com
• AG1: https://drinkag1.com
• How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com): https://www.lennysnewsletter.com/p/how-to-find-hidden-growth-opportunities-albert-cheng
• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth
• The Elephant in the room: The myth of exponential hypergrowth: https://longform.asmartbear.com/exponential-growth
• HubSpot: https://www.hubspot.com
• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building
• Adjacency Matrix: How to expand after PMF: https://longform.asmartbear.com/adjacency/
• Ecosystem is the next big growth channel: https://www.lennysnewsletter.com/p/ecosystem-is-the-next-big-growth
• ChatGPT apps are about to be the next big distribution channel: Here’s how to build one: https://www.lennysnewsletter.com/p/chatgpt-apps-are-about-to-be-the
• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths
• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams
• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead
• ER on Prime Video: https://www.amazon.com/ER-Season-1/dp/B0FWK5WJQ4
• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD
• Wispr Flow: https://wisprflow.ai
• Anker: https://www.anker.com
—
Recommended books:
• Will: https://www.amazon.com/Will-Smith/dp/1984877925
• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867
• Hidden Multipliers: Small Things That Accelerate Growth: https://preorder.hiddenmultipliers.com
• On Writing Well: The Essential Guide to Mastering Nonfiction Writing and Effective Communication: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548
• Crossing the Chasm, 3rd Edition: The Updated Version of the Insightful Guide on Bringing Cutting-Edge Products to the Mainstream: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.
To hear more, visit www.lennysnewsletter.com
This AI Startup Idea Has 500 Million Customers Waiting For It
Episode 554: Shaan Puri (https://twitter.com/ShaanVP) and Sam Parr (https://twitter.com/theSamParr) brainstorming unicorn startup ideas with $1B founder Jason Cohen.
Want to see Sam and Shaan’s smiling faces? Head to the MFM YouTube Channel and subscribe - http://tinyurl.com/5n7ftsy5
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Show Notes:
(0:00) Intro
(3:00) AI improved presentations
(10:30) Automated Twitter hacking
(13:00) Being a billionaire tinkerer
(17:30) Rich vs. King
(22:30) All startups are screwed up--including the ones that work
(30:30) Be so good you can't fail
(32:30) Consumers don't value their time
(35:30) Will WP Engine go public?
(37:00) Lessons from Silver Lake Capital elites
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Links:
• Smart Bear - https://smartbear.com/
• Jason Cohen on Twitter - https://twitter.com/asmartbear
• Zeck - https://www.zeck.app/
• Rich v. King - https://longform.asmartbear.com/rich-vs-king-sold-company
• Box.com - http://box.com/
• Silver Lake - https://www.silverlake.com
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Check Out Sam's Stuff:
• Hampton - https://www.joinhampton.com/
• Ideation Bootcamp - https://www.ideationbootcamp.co/
• Copy That - https://copythat.com
• Hampton Wealth Survey - https://joinhampton.com/wealth
—
Check Out Shaan's Stuff:
Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd
Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more.
—
Other episodes you might enjoy:
• #224 Rob Dyrdek - How Tracking Every Second of His Life Took Rob Drydek from 0 to $405M in Exits
• #209 Gary Vaynerchuk - Why NFTS Are the Future
• #178 Balaji Srinivasan - Balaji on How to Fix the Media, Cloud Cities & Crypto
• #169 - How One Man Started 5, Billion Dollar Companies, Dan Gilbert's Empire, & Talking With Warren Buffett
• #218 - Why You Should Take a Think Week Like Bill Gates
• Dave Portnoy vs The World, Extreme Body Monitoring, The Future of Apparel Retail, "How Much is Anthony Pompliano Worth?", and More
• How Mr Beast Got 100M Views in Less Than 4 Days, The $25M Chrome Extension, and More
How Scaling Turns Rare Occurrences Into Common Ones with Jason Cohen
Today Corey Quinn is joined by Founder and Chief Innovation Officer at WP Engine, Jason Cohen. Jason breaks down the biggest issues he has seen throughout his career hosting millions of websites including why seemingly rare problems should be expected at scale, how moving on after attaining a “good enough” metric can save time and money, and what it means to be proud of your work in the world of cybersecurity. Check it out!
Show Highlights
(00:00) - WordPress popularity and outsourcing engineering tasks
(07:28) - Web hosting and scalability
(11:01) - Server reliability and quality control
(14:18) - Scaling infrastructure and prioritizing customer value
(26:20) - Website speed and optimization
(28:17) - WordPress scalability and deployment in a cloud environment
(36:14) - Customer profitability and service limitations
(38:54) - Security measures for ethical decision-making
(47:19) - Balancing free speech and decision-making in online content moderation
About Jason
Founder of unicorn WP Engine (200,000 customers, 1,200 employees). Previously founder of bootstrapped Smart Bear (sold 2008; re-sold in 2021 at ~$2B) and ITWatchDogs (sold 2004). Original mentor and angel investor with Austin-based Capital Factory since 2009.
Written about startups for seventeen years, most recently at https://longform.asmartbear.com; Twitter: @asmartbear.
Links Referenced:
Personal Website: https://longform.asmartbear.com/
WP Engine: https://wpengine.com/
Linkedin: https://www.linkedin.com/in/jasoncohen/
SaaStr 265: WP Engine SVP of Global Sales Matt Schatz on Building a $100M ARR Sales Team - The Second Time Around
Matt Schatz is SVP of Sales at WPEngine, responsible for defining and executing the global sales strategy. Matt has nearly two decades of senior leadership experience in sales and customer growth, specifically for technology companies with customers around the world including Bazaarvoice, CityVoice and Rackspace.
Missed the session? Here's what Matt talks about:
Getting your "first story"
What is a lucky lead and how does that turn into predictable growth
Building trust across time zones
This podcast is an excerpt of Matt's session at SaaStr Annual 2019. You can watch the full session on our blog.
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
SaaStr
WP Engine
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#088 – Sage Advice (and Reasons You Probably Won't Follow It) from Jason Cohen of WP Engine
Not only has Jason Cohen (@asmartbear) bootstrapped a software company from $0 to over $1M in revenue, but he's done it four times! The stories behind Jason's successes are plastered all over the Internet for anyone to find, so I decided to take a different approach: I skipped Jason's backstory and instead proceeded to squeeze him like a sponge to extract every ounce of advice I possibly could in the hour we had together. The result is a wide-ranging discussion about the best path for reaching your first $10k/month in revenue, the lies we tell ourselves as founders, and why you probably won't take the advice that Jason (or anyone else for that matter) gives you.
Transcript, speaker information, and more: https://www.indiehackers.com/podcast/088-jason-cohen-of-wp-engine
Ep. 8: Better Beer Through AI
Whether brewing hearty stouts or crisp lagers, flavor is a fickle thing. Not only is it hard to create consistently good brew, as humans our ability to identify - and remember - flavors is flawed. Yet brands worth billions rely on creating consistent flavors. We talk to Jason Cohen, founder of Gastrograph, who is using AI to help businesses that create beer, chocolate, wine, coffee, and spirits better understand flavor.