--- title: "The Deal That Froze Our Payments with Dmitry Dragilev" id: "1740" type: "post" slug: "s3e41-frozen-payments-dmitry-dragilev" published_at: "2026-10-13T14:45:00+00:00" modified_at: "2026-10-13T22:29:12+00:00" url: "https://yourbusinessgrowthplaybook.com/s3e41-frozen-payments-dmitry-dragilev/" markdown_url: "https://yourbusinessgrowthplaybook.com/s3e41-frozen-payments-dmitry-dragilev.md" excerpt: "What if a massive deal that brought in four thousand new customers turned out to be the very thing that almost destroyed your company? Our guest today launched a SaaS platform that grew rapidly, landing major brand users like Airbnb..." taxonomy_category: - "Podcast Episodes" - "Podcast Season 3" - "SaaS Businesses" - "Seven Figure Business" - "Successful Exits" --- # The Deal That Froze Our Payments with Dmitry Dragilev Published in [Podcast Episodes](https://yourbusinessgrowthplaybook.com/category/podcast/) , [Podcast Season 3](https://yourbusinessgrowthplaybook.com/category/podcast/podcast-season-3/) , [SaaS Businesses](https://yourbusinessgrowthplaybook.com/category/podcast/saas-businesses/) , [Seven Figure Business](https://yourbusinessgrowthplaybook.com/category/podcast/seven-figure-business/) , [Successful Exits](https://yourbusinessgrowthplaybook.com/category/podcast/successful-exits/) What if a massive deal that brought in four thousand new customers turned out to be the very thing that almost destroyed your company? Our guest today launched a SaaS platform that grew rapidly, landing major brand users like Airbnb and HubSpot. But when a misunderstanding over lifetime deals erupted into a wave of chargebacks and Stripe disputes, his business was on the brink of collapse. Instead of giving up or clinging to a pure SaaS model, he pivoted to an unexpected model that rescued his revenue, stabilized his operations, and paved the way for a near-million-dollar exit. Today, he shares the lessons learned across four company sales – and how he builds exit-ready businesses working just three hours a day. Welcome to today’s episode of [Your Business Growth Podcast](https://yourbusinessgrowthplaybook.com/podcast/) . I’m your host, Jeremy Shapiro, author of *[Your Business Growth Playbook](https://yourbusinessgrowthplaybook.com/)*, and my guest today is Dmitry Dragilev. [Listen on iTunes](https://podcasts.apple.com/us/podcast/your-business-growth-podcast/id1826637671?i=1000796140827) [Listen on Spotify](https://open.spotify.com/episode/1cU6B3fsoDNv8BQB7nae4l) [Watch on YouTube](https://youtu.be/mv5mo2EPXNw) --- ## About Dmitry Dragilev Dmitry Dragilev is a serial-exit founder who builds SaaS and technology companies designed specifically to be acquired. Over the past 12 years, he has successfully exited four companies—including a buyout by Google, a sale to SEOJet, and two acquisitions by Semrush. Most recently, his SERP Gap Analyzer was acquired by Semrush in October 2025, which was subsequently acquired by Adobe in a $1.9 billion deal. Dmitry builds all of his ventures around a strict three-hour workday constraint. Rather than treating limited working hours as a post-acquisition luxury, he uses this constraint from day one to force ruthless prioritization, delegation, and operational simplicity. Throughout his career, he has built and managed software platforms used by over 5,000 customers, including enterprise brands like Airbnb and HubSpot. Currently, Dmitry is the founder of LLM Gap Analyzer, which scaled to nearly $30,000 in monthly recurring revenue within three months of launch. He is also partnering with a former IRS revenue agent on an IRS Resolution Service, combining his growth engineering expertise with specialized subject-matter authority. Through his biweekly newsletter read by over 20,000 subscribers, Dmitry teaches entrepreneurs how to build lean, highly profitable, and exit-ready companies without suffering from burnout. ## Connect with Dmitry Dragilev - [Criminally Prolific.com](https://criminallyprolific.com/) - [LinkedIn](https://www.linkedin.com/in/dmitrydragilev/) ## Speed Round Answers: - All In Lead Source: App stores / marketplaces - Books: *How Will You Measure Your Life?* by Clayton M. Christensen, *The Innovator’s Dilemma* by Clayton M. Christensen, *Lost and Founder* by Rand Fishkin, *The Four Hour Workweek* by Tim Ferriss - Unlikeliest Mentor: Rinaldi Sai of Crossloop, and Patrick Byrne, former CEO of Overstock.com ## Like This Episode? There’s More! ### Subscribe! Your Business Growth Podcast is available on all major [podcast platforms](https://yourbusinessgrowthplaybook.com/podcast/#subscribe) . Subscribe today! [Subscribe!](https://yourbusinessgrowthplaybook.com/podcast/#subscribe) ### Get the Book! Pickup the #1 Best Seller, [Your Business Growth Playbook](https://yourbusinessgrowthplaybook.com/) today online or at your local bookseller! [Get the Book!](https://yourbusinessgrowthplaybook.com/buy/) ### Meet Jeremy! Book your [Blueprint Discovery Call](https://yourbusinessgrowthplaybook.com/blueprint/) with Jeremy today and get back to the growth you deserve! [Book a Call!](https://yourbusinessgrowthplaybook.com/blueprint/) ## Dmitry Dragilev Episode Transcript Coming Soon! ## Like This Episode? There’s More! ### Subscribe! Your Business Growth Podcast is available on all major [podcast platforms](https://yourbusinessgrowthplaybook.com/podcast/#subscribe) . Subscribe today! [Subscribe!](https://yourbusinessgrowthplaybook.com/podcast/#subscribe) ### Get the Book! Pickup the #1 Best Seller, [Your Business Growth Playbook](https://yourbusinessgrowthplaybook.com/) today online or at your local bookseller! [Get the Book!](https://yourbusinessgrowthplaybook.com/buy/) ### Meet Jeremy! Book your [Blueprint Discovery Call](https://yourbusinessgrowthplaybook.com/blueprint/) with Jeremy today and get back to the growth you deserve! [Book a Call!](https://yourbusinessgrowthplaybook.com/blueprint/) ## More posts - ### [The Deal That Froze Our Payments with Dmitry Dragilev](https://yourbusinessgrowthplaybook.com/s3e41-frozen-payments-dmitry-dragilev/) [October 13, 2026](https://yourbusinessgrowthplaybook.com/s3e41-frozen-payments-dmitry-dragilev/) - ### [Permission Beats Pressure on LinkedIn](https://yourbusinessgrowthplaybook.com/permission-beats-pressure-on-linkedin/) [October 9, 2026](https://yourbusinessgrowthplaybook.com/permission-beats-pressure-on-linkedin/) - ### [The Lyon Show: Break Through Your Growth Plateau Without Burning Out](https://yourbusinessgrowthplaybook.com/the-lyon-show-break-through-your-growth-plateau-without-burning-out/) [October 8, 2026](https://yourbusinessgrowthplaybook.com/the-lyon-show-break-through-your-growth-plateau-without-burning-out/) - ### [Your Inbox Is Crowded. Try the Mailbox](https://yourbusinessgrowthplaybook.com/inbox-is-crowded-try-the-mailbox/) [October 7, 2026](https://yourbusinessgrowthplaybook.com/inbox-is-crowded-try-the-mailbox/)