The SaaS Podcast - Real Lessons on Growing Profitable SaaS

Most founders fight SaaS churn by trying to save every customer. Caleb Avery fixed SaaS retention by firing 40% of them. After years in payments consulting, Caleb built Tilled and discovered that only 15-20 of his first 50 customers were succeeding. The rest were dragging the business down. Caleb reveals how deliberate customer retention pruning triggered 500% year-over-year growth, why LinkedIn c...

Adam Robinson bootstrapped three SaaS startups to $1M+ ARR, and he did it faster every time. Robly took 17 months. Retention.com took 27 weeks. RB2B took just 16 weeks. This serial SaaS founder never raised a dollar of outside funding for any of them. Adam breaks down the exact playbook at each stage - from running a call center out of his apartment, to provocative Facebook ads, to building a 92,0...

Most SaaS founders obsess over getting more signups but ignore the user flows that turn signups into paying customers. Peter Loving has redesigned SaaS onboarding and growth flows for dozens of companies - and one dashboard redesign alone added $300K in ARR by lifting trial-to-paid from 18% to 26%. Peter breaks down 7 critical flows: signup, SaaS onboarding, activation, upgrade, core workflow, int...

Jason Radisson grew up in poverty, raised by a 16-year-old single mother on a dirt road in rural Massachusetts. He became a Fulbright Scholar, went to Harvard, joined McKinsey, then built Movo into an enterprise sales machine with nearly 100 customers and 700,000 workers on the platform. Jason reveals how founder-led sales and warm intros at the C-level compressed enterprise sales cycles to 2-3 we...

Patrick Barnes expected 4,000 ideal customers to jump on his new Amazon integration. Instead, it got 46 clicks. That kind of humbling moment keeps happening - even when you've figured out selling SaaS without sales experience well enough to reach 20,000 customers and eight figures in ARR. Patrick reveals how he bootstrapped and sold Advocately to G2, then acquired a Shopify app with 2,000 customer...

Jonathan Rhyne was an attorney selling appliances at Sears when he spotted an opportunity to overhaul SaaS subscription billing at a tiny developer tools startup doing just $20K MRR. Learn how switching from one-time licenses to SaaS subscription billing, segmenting customers by size, and charging premium prices for new features grew PSPDFKit to $1M ARR in 8 months. Jonathan reveals how he restruc...

Lav Crnobrnja forgot about his landing page for nine months. Then one email from a frustrated waitlist subscriber changed everything. That single message became the early traction signal that turned a company hackathon side project into a $2M ARR bootstrapped SaaS with 2,500 customers. Lav reveals how building Slack-first instead of adding Slack as an integration created a genuine differentiator,...

Guillaume Moubeche launched lemlist with $1,000 and a bootstrap to profitability mindset. Today, lempire generates $26 million in ARR with just 90 people and $10 million in EBITDA. But the path from surviving on pasta to running five profitable SaaS products was anything but smooth. Guillaume reveals how building in public with real cold email results drove 30% month-over-month growth, why warm ou...

Jake Stein spent six months pitching enterprise customers and got zero conversions. They loved the vision of standardized contracts but wouldn't be the first to adopt. His SaaS product validation journey across three startups reveals why validating SaaS ideas with the right buyer matters more than having the right product. Jake shares how RJ Metrics' SaaS go-to-market took eight years before selli...

Dean Mathews ran his self-funded SaaS as a side project for over a decade - spending just 20 hours a week while consulting full-time. By the time he went all in, OnTheClock had already crossed $1M in annual recurring revenue. Learn how this self-funded SaaS grew to $5M+ ARR with 18,000 customers and zero outside funding. Dean reveals how he validated the idea through forum research without a singl...

Michael Zuercher spent a year struggling to explain how Prismatic differed from Mulesoft and Zapier. Every sales call ended with "I don't understand how you're different." Then SaaS product-market fit finally clicked around $1M ARR - and conversations shifted from confusion to immediate understanding. Michael reveals how building 600 integrations at his previous company led to Prismatic, why findi...

Kaveh Rostampor bootstrapped a SaaS retention platform for six years, grew it to eight figures in ARR, then raised $50 million - and still hasn't spent it. Learn how Planhat used just two growth channels to reach 8-figure ARR and why SaaS retention became the foundation of their entire business. Kaveh reveals how paid ads targeting department heads with outcome-based messaging about reducing churn...

Zach Rattner forced himself through the door of a moving company for the 18th time, phone in hand, looking for an excuse not to walk in. Building AI products as an introverted engineer meant every cold call felt like torture - and half the people he pitched said his AI startup would never work. Learn how building AI products with LOI validation de-risked a technically ambitious vertical AI startup...

Evan Liang spent three years trying to close some of his first deals at LeanData because prospects didn't know his category existed. Paid search was useless - there were literally no keywords to bid on. Building a sales pipeline in a category nobody searched for required a completely different SaaS go-to-market playbook. Learn how LeanData built a sales pipeline through events and customer-led gro...

Tim Schumacher has completed 18 SaaS acquisition deals, building a portfolio that generates over $60M in ARR across 300 employees in 33 countries. Most targets are bootstrapped SaaS companies valued between 2x and 3x ARR. Learn what SaaS acquisition buyers actually look for, how earn-out structures push acquisition valuation multiples higher, and why reducing founder-dependency is the most importa...

Juan Ignacio Garcia tried to acquire three SaaS businesses and failed every time because nobody would finance the deal. So he built Boopos, a marketplace with built-in acquisition financing. Most SaaS businesses sell for 4-8x profit multiples - but SaaS pricing for your exit depends on retention, financials, and deal strategy. Learn the complete playbook for SaaS pricing when selling a SaaS busine...

Bob Moore quit his VC job the day before Lehman Brothers collapsed. He bootstrapped RJ Metrics, sold it to Magento, then spun out the same technology as Stitch and sold it for $60M in 18 months. Now his SaaS partnerships platform Crossbeam serves 19,000 companies at 8-figure ARR. Learn how to sell the same company twice, why SaaS partnerships require solving the cold start problem with joint onboa...

Lars Gronnegaard left Trustpilot with a clear SaaS sales process plan. Then reality hit. His first 10 customers looked nothing like the ICP. Cold outreach needed 180 days to show results. It took a LinkedIn content strategy hitting 300,000 views to finally reach 7-figure ARR. Learn how a documented SaaS sales process replaced tribal knowledge, why 28-day outbound cycles beat 180-day sequences for...

Thomas Cottereau spent five years building what Oracle's engineers said was technically impossible. When he demoed the B2B SaaS sales platform at Salesforce, a lead engineer tested every feature by midnight and emailed: 'It works as you said. Come to my office tomorrow.' Learn how weekly office visits earned a strategic partnership for B2B SaaS sales, why HP saved millions using SightCall for remo...

Andrew Guttormsen did over 1,500 one-on-one demos in 18 months - consultative selling SaaS the hard way. That personal touch turned Circle into a $19M ARR business. A single JV webinar with anchor customers like Pat Flynn drove 300 new customers in one push. Learn how consultative selling SaaS through founder-led demos built unstoppable word of mouth, why anchor customers accelerated the SaaS sale...

Adam Gavish had never sold anything in his life. As a Google PM, he had to become DoControl's first SDR - selling SaaS without sales experience. He pitched 22 VCs in one week (21 said no), landed a first customer at $2K/year, and scaled deals to $25K+ by treating every call as a founder-led sales feedback session. Learn the playbook for selling SaaS without sales experience, how 50 validation inte...

An investor told Stephany Lapierre she would never raise capital. She had three kids, no tech background, and no co-founder. But she flipped that rejection into fuel, raised $72M in startup funding for TealBook, and built an enterprise SaaS platform serving over 100 Fortune 1000 customers. Learn how a non-technical founder overcame enterprise SaaS fundraising rejection, why the 'ZoomInfo for procu...

Jared Brown invested $52,000 with a stranger he met on LinkedIn. Eleven years later, Hubstaff generates $22M in ARR and SEO is still the engine scaling SaaS to 16,000 customers. COVID doubled revenue from $6M to $12M in just 12 months of SaaS growth. Discover how SEO alone drove scaling SaaS from zero to $22M ARR, why low pricing created viral bootstrapped growth loops, and how continuous onboardi...

Brennan Dunn raised $500K, grew RightMessage to $35K MRR in a year, then watched it all slide backward. For two years, SaaS retention flatlined and both co-founders lost motivation. The SaaS churn problem was clear - too broad a market and customers who lacked the data the product needed. Learn how narrowing niche positioning reignited SaaS retention, why hands-on onboarding turned a customer rete...

Simon Taylor showed up at Nutanix headquarters wearing a bright white jacket with a red carnation - and nobody knew who he was. A year later, his enterprise sales through that partner-first strategy had delivered thousands of enterprise customers for HYCU across 78 countries. Learn how a partner-first strategy for enterprise sales replaced cold calling, why education-first content drew 2,000 webin...