Richard Hollingsworth bootstrapped an executive assistant agency to $5M ARR, then pivoted to AI and grew from $1M to $18M ARR in just 8 months. Today, Fyxer serves thousands of professionals with their AI email assistant, and Richard's team has grown from 4 to 40 employees while raising over $40M. Richard and his brother Archie started with data from their EA agency, waited for the right technology moment with GPT-3, then moved to San Francisco to scale. Their focus on professional services over tech companies, combined with a land-and-expand strategy, helped them close a $1.2M deal in 7 days and build a thriving AI SaaS business. You'll learn: How to turn an agency into an AI SaaS company using existing customer data and insights Why targeting professional services instead of tech companies unlocked massive growth opportunities How a land-and-expand sales motion helped convert single users into a 5,000-seat enterprise deal worth $1.2M What mistakes nearly destroyed their customer success during hypergrowth and how they recovered How to maintain culture and intensity while scaling from 4 to 40 employees in under a year Full show notes → saasclub.io/454 This episode is brought to you by: 💖 Gearheart → Book a free strategy session + get 20% off select services Get weekly SaaS lessons and new founder stories → saasclub.io/email

Bernard Aceituno went from PhD research at MIT to founding StackAI, a no-code AI platform that's now generating 7-figures in ARR with over 100 enterprise customers and $16M raised. In this episode, Bernard shares how he pivoted from academia to entrepreneurship, why his first product wasn't solving the right problem, and how a perfectly-timed MVP launch on Hacker News created overnight demand. He explains the painful lessons of chasing too many customer segments before finding focus with enterprise IT teams. You'll learn: What signals showed Bernard it was time to pivot from dataset management to workflow automation Why chasing too many ICPs nearly derailed the company and how they found focus How posting a scrappy MVP on Hacker News created 20 customer meetings in just two days Why attempts at reseller channels failed and what Bernard learned from waiting too long to hire sales How focusing on enterprise IT unlocked large contracts and steady expansion inside customer accounts Full show notes → saasclub.io/453 This episode is brought to you by: 💖 Gearheart → Book a free strategy session + get 20% off select services Get weekly SaaS lessons and new founder stories → saasclub.io/email

Pat Kinsel went from years of painful struggle at Notarize to building Proof, a SaaS platform approaching $100M ARR with 230 employees and $260M raised. In this episode, Pat explains how a notary error during his first startup exit sparked the idea, why he validated demand with a simple landing page before building, how he endured years of slow traction and false signals, and what changed when he expanded beyond notarization to transaction security. You’ll learn: - How Pat validated demand with a landing page and Google ads - Why losing money on every transaction nearly killed the company - What really happened when COVID demand spiked 100x overnight - How he spent years pushing to make online notarization widely accepted - Why many COVID-era enterprise signups never activated and what that taught about real product-market fit Full show notes → saasclub.io/452 This episode is brought to you by: 💖 Gearheart → Book a free strategy session + get 20% off select services 📫 Mailtrap → Get 20% off with code THESAASPODCAST Get weekly SaaS lessons and new founder stories → saasclub.io/email

Todd Olson went from two failed startups to building Pendo, a SaaS platform now generating $200M ARR with 880 employees and nearly $500M raised. In this episode, Todd reveals how early mistakes shaped his obsession with product-market fit, why he refused to hire salespeople until he validated the sales motion himself, and how creating an entirely new category forced him to abandon inbound marketing for manual outreach. You’ll learn: - Why Todd waited until $500K ARR before hiring salespeople - How raising prices 10x overnight changed Pendo’s trajectory - What two failed startups taught him about product-market fit - Why category creation required a bold go-to-market approach - The counterintuitive product strategy that made Pendo stand out Full show notes → saasclub.io/451 This episode is brought to you by: 💖 Gearheart → Book a free strategy session + get 20% off select services 📫 Mailtrap → Get 20% off with code THESAASPODCAST Get weekly SaaS lessons and new founder stories → saasclub.io/email

Flo Crivello is the founder and CEO of Lindy, a no-code platform for building AI agents to automate workflows. 👉 This episode is sponsored by Mailtrap. Try it at ⁠⁠Mailtrap.io⁠⁠ — use code THESAASPODCAST for 20% off Show Notes: ⁠https://saasclub.io/450 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: ⁠https://saasclub.io/email/⁠ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: ⁠https://saasclub.io/join/

Richard White is the founder and CEO of Fathom, the #1 rated AI note-taking app that automatically captures and summarizes meetings. 👉 This episode is sponsored by Mailtrap. Try it at ⁠Mailtrap.io⁠ — use code THESAASPODCAST for 20% off Show Notes: https://saasclub.io/449 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.io/join/

Rob Woollen is the Co-Founder and CTO of Sigma Computing, a data analytics platform that lets business users analyze cloud-scale data without writing SQL. 👉 This episode is sponsored by Mailtrap. Try it at Mailtrap.io — use code THESAASPODCAST for 20% off Show Notes: Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs:

Jared Siegal is the founder and CEO of Aditude a monetization platform that helps digital publishers maximize their ad revenue. Show Notes: https://saasclub.io/447 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

David Zitoun is the co-founder and CEO of Submagica tool that helps creators and small businesses turn their videos into viral-ready shorts in just a few clicks. Show Notes: https://saasclub.io/446 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

Stefan Bader is the co-founder and CEO of Cello, an all-in-one referral platform that helps SaaS companies reward their users for bringing in new customers. Show Notes: https://saasclub.io/445 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

Jonathan Festejo is the co-founder and CEO of Salesbricks, a platform that helps startups close deals faster and take the manual work out of quoting, billing, and getting paid. ==================================== ❤️ This episode is powered by Gearheart ⁠⁠⁠⁠https://saasclub.io/gearheart⁠⁠⁠⁠ Book a free 1:1 consultation: ⁠⁠⁠⁠https://saasclub.io/gearheart/book⁠⁠⁠⁠ ==================================== Show Notes: ⁠⁠⁠https://saasclub.io/444⁠⁠ Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: ⁠⁠⁠https://saasclub.io/email/⁠⁠⁠ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: ⁠⁠⁠https://saasclub.co/join⁠⁠⁠

Joseph Lee is the co-founder and CEO of Supademo, an AI-powered platform that helps you create interactive demos for onboarding, sales, and product education. ==================================== ❤️ This episode is powered by Gearheart ⁠⁠⁠https://saasclub.io/gearheart⁠⁠⁠ Book a free 1:1 consultation: ⁠⁠⁠https://saasclub.io/gearheart/book⁠⁠⁠ ==================================== Show Notes: ⁠⁠https://saasclub.io/443⁠ Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: ⁠⁠https://saasclub.io/email/⁠⁠ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: ⁠⁠https://saasclub.co/join⁠⁠

Sam Naficy is the CEO of Prodoscore, a SaaS platform that uses AI to show companies how work gets done by analyzing data from the cloud tools employees already use every day. ==================================== ❤️ This episode is powered by Gearheart ⁠⁠https://saasclub.io/gearheart⁠⁠ Book a free 1:1 consultation: ⁠⁠https://saasclub.io/gearheart/book⁠⁠ ==================================== Show Notes: ⁠https://saasclub.io/442 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: ⁠https://saasclub.io/email/⁠ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: ⁠https://saasclub.co/join⁠

Egidijus Pilypas is the co-founder of Exacaster, a SaaS company that helps subscription-based businesses grow revenue by turning customer data into actionable insights. ==================================== ❤️ This episode is powered by Gearheart ⁠https://saasclub.io/gearheart⁠ Book a free 1:1 consultation: ⁠https://saasclub.io/gearheart/book⁠ ==================================== Show Notes: ⁠https://saasclub.io/441 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: ⁠https://saasclub.io/email/⁠ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: ⁠https://saasclub.co/join⁠

Rami Tamir is the co-founder and CEO of Salto, a platform that helps teams manage and automate the configuration of SaaS apps like Salesforce, NetSuite, and Okta. ==================================== ❤️ This episode is powered by Gearheart https://saasclub.io/gearheart Book a free 1:1 consultation: https://saasclub.io/gearheart/book ==================================== Show Notes: https://saasclub.io/440 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

Sameer Al-Sakran is the founder and CEO of Metabase, an open-source BI tool that helps teams quickly turn raw data into charts and dashboards. ==================================== ❤️ This episode is powered by Gearheart https://saasclub.io/gearheart Book a free 1:1 consultation: https://saasclub.io/gearheart/book ==================================== Show Notes: https://saasclub.io/439 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

Callum Mckeefery is founder and CEO of Partner.io, a platform that helps companies run smoother partner programs and grow revenue faster. ==================================== ❤️ This episode is powered by Gearheart https://saasclub.io/gearheart Book a free 1:1 consultation: https://saasclub.io/gearheart/book ==================================== Show Notes: https://saasclub.io/438 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

Onur Alp Soner is the founder and CEO of Countly, a privacy-first product analytics platform. ==================================== ❤️ This episode is powered by Gearheart https://saasclub.io/gearheart Book a free 1:1 consultation: https://saasclub.io/gearheart/book ==================================== Show Notes: https://saasclub.io/437 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

Oscar Rubio is the founder and CEO of LodgerIn, a SaaS platform helping organizations manage housing and relocation services for students and employees moving abroad. ==================================== ❤️ This episode is powered by Gearheart https://saasclub.io/gearheart Book a free 1:1 consultation: https://saasclub.io/gearheart/book ==================================== Show Notes: https://saasclub.io/436 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

Andrew Gazdecki is the founder and CEO of Acquire.com, the largest marketplace for buying and selling SaaS startups. Show Notes: https://saasclub.io/435 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join