All Episodes

#218: He Built Debt Collection SaaS While Paying Off $1M in Personal Debt - Josh Allen

#217: His Hardest Lesson: Going Too Fast Was More Risky, Even With Funding - Shawn Boyer

#216: Messy Financials Killed a Good LOI and Slowed a Profitable SaaS Sale - Riccardo Pisano

#215: How This Early-Stage Growth Equity Partner Is Investing in SaaS in 2026 - Steve Wolfe

#214: He Stopped Being the Face of the Company Before He Sold It - Heath Adams

#213: She Took on a Growth Equity Partner for the Advice, Not the Money - Lynn Burghardt

#212: The Practical Case for Payments-Driven SaaS Growth, Not Subscriptions - Jay Majaraj

#211: This Practical Bootstrapper Scaled Up and Became a Serial Acquirer - Ajay Gupta

#210: 4th Time Founder: Solve Distribution First, Write Code After - Vic Levitin

#209: Leading from Both Sides of the Table as a PE-Backed SaaS CEO - Steve Oriola

#208: How AI Rewrote What Active SaaS Buyers Want in 2026 - Mike Lyon

#207: Former Teacher Built a Market-Leading School Hiring Marketplace - Wayne Cartmel

#206: He Sold at $3M ARR and Got a 10X+ Exit to a PE Buyer - Eran Galperin

#205: Domain Knowledge Is the New Moat, Not Features and Code - Cliff Sentel

#204: He Sold a Majority, Gave Up Control, and Became Indispensable - Matthew Bullis

#203: Every Software Team Should Put AI Agents on the Org Chart - Nick Olsen

#202: Practical Fintech: Surviving Payment Platforms and Big Banks - Paul Hoeper

#201: Creating a New Category in SaaS for Key Account Managers - Jerry Alderman

#200: The Biggest Pricing Mistakes That Hurt Growing SaaS Companies - TJ Joosten

#199: Enterprise SaaS Built on Salesforce to a Practical Founder Exit - Rupert Mayer

#198: Protecting the Soul of Your Company, with Eric Ries, Author of the Lean Startup

#197: Scaled His Niche Vertical SaaS ERP with Growth Equity - Marc Sanderson

#196: Founder Conflict, Burnout, and a Successful SaaS Exit - Blakely Graham

#195: Built a Calm, Profitable SaaS—Then Sold It on His Terms - Andy Alsop

#194: Why Selling Your Company Can Be a Growth Strategy - Sharon Nouh

#193: The Real Bottom of the Funnel: SaaS Onboarding That Works - Perry Rosenbloom

#192: Built A Vertical SaaS Giant In Aviation Without VC Funding - Dinakara Nagalla

#191: No Investors the 2nd Time - Bootstrapped to a Bigger Exit - Chad Ingram

#190: Building Faster with AI-Powered Product Demos That Convert - Joseph Lee

#189: How Lighter Capital Finances Bootstrapped SaaS Growth - Tanner Kovacevich

#188: The Practical Long Game: 25 Years Scaling QuestionPro - Vivek Bhaskaran

#187: Practical Rule of 40 Growth+Profits Still Works for SaaS Acquirers - Juan Ignacio Garcia Braschi

#186: The Grind Behind a Stellar SaaS Exit in the UK - Simon Swords

#185: Survived COVID and a PE Exit —A Travel Tech Founder's Journey - Steve Reynolds

#184: Fixing The Software Development Mess For Non-Technical Founders - Keith Shields

#183: Selling to the Gorilla: Snap's Strategic Exit to ICE Mortgage Tech - Will Caldwell

#182: Why Focus Beats Funding in Crowded SaaS Markets - Luigi Mallardo

#181: Why Systems (with AI) Scale Better Than People in SaaS - Jordon Comstock

#180: AI Is Not Killing Vertical SaaS - It's Practical Leverage - Deepak Sindwani

#179: Don't Sell Your SaaS Yet: Hire a CEO and Get Your Life Back - Tighe Burke

#178: Approaching $20 Million ARR with 99% Annual Retention - Dan MacDonald

#177: Building Multi-product Vertical SaaS With a Tiny Team - Robin Eissler

#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head

#175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh

#174: Plateaus, Pivots, and Staying Profitable: Solving Practical SaaS Puzzles - Josh Ho

#173: From COVID Boom to Bootstrap Mode: Hubilo's Refounder Story - Shailesh Hegde

#172: Why Long-Term Bootstrapping Still Works in Event Mgt. SaaS - Raju Patel

#171: Lessons from a 9-Year Bootstrap Journey to a Private Equity Exit - Dharshan Rangegowda

#170: Why Most SaaS Acquirers Still Want Profitable Growth in 2025 - Gaurav Bhasin

#169: Practical Pivot and Relaunch Created Profitable 200% Growth - Natalie Barbu

#168: These Three Superpowers Set Practical SaaS Founders Apart - Greg Head

#167: Practical Founders Brought in CEO to Scale Their Company - Darryl Pahl

#166: How Practical SaaS Founders Can Compete in the AI Economy - Vincent Serpico

#165: How to Enjoy Being the CEO as Your SaaS Business Grows Bigger - Brett Gilliland

#164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta

#163: Anthony Pierri & Rob Kaminski of Fletch: Why All SaaS Founders Struggle with Positioning

#162: Practical Investor - What's Working Now in AI-Driven SaaS Growth - Dave Yuan

#161: When Co-Founders Need Relationship Therapy - Dr. Matthew Jones

#160: CPG Founder Turned Failure Into a Profitable SaaS Business - Yuval Selik

#159: Co-Parenting App Reaches $10M ARR Through Pure Bootstrap Growth - Vince Mayfield

#158: $33M Growth Equity After Friends/Family Funding to $10M ARR - Alan Miegel

#157: Seven Years In Survival Mode: A VC-funded Founder's Warning - Zvi Band

#156: Bootstrapper Built Vertical CRM to $10M ARR with Co-founder Dad - Shoanak (Sean) Mallapurkar

#155: SaaS Founder's Crazy Ride: Boom, Bust, Strategic Sale - Jesse Burrell

#154: 2nd-Generation CEO Modernizes Mom's Legacy Software Business - Brian Forbis

#153: Bootstrapper Killed His First Company to Scale Up Bigger - Chris Brisson

#152: Practical SaaS CEO Stays On After 100% Cash Sale - Tracy Larson

#151: Facial Recognition SaaS for Casinos to Almost $10M in Revenue – Henry Valentino

#150: Grew an Unsexy Small Software Biz Into a SaaS Powerhouse - Josh Turley

#149: How Partner-Led Sales Built A $7M Bootstrap SaaS Business - Sameer Narkar

#148: These Bootstrappers Sold Modern Digital LeadGen to Conservative German Businesses - Chris Erler

#147: How a Philadelphia Insurance Agent Built the Uber of Surety Bonds - Aaron Steffey

#146: This European SaaS Bootstrapper Raised $22M in Growth Equity Without Losing Control - Roy van den Broek

#145: Making Big Bold Bets with Patient Execution as a Bootstrapped Founder - Gopal Krishnamurthy

#144: From Founder-Led Sales to Scalable Go-To-Market in Vertical SaaS - Phil Stern

#143: From Professional Services to a $30M SaaS Business with a PE Acquisition - Sean Hoban

#142: Why This 3x SaaS Founder Couldn't Stay Retired to Launch His New Al Startup - Josh LaSov

#141: Inside Acquire.com's Process for Selling Sub-$5M SaaS Companies - Andrew Gazdecki

#140: The Anti-Silicon Valley Playbook: How Genius Monkey Built a $100M Ad Tech Business on Their Own Terms - Seth Hassell and Clint Ethington

#139: Bootstrapped Founder is Getting Ready for the AI Wave at $20M ARR - Shalin Jain

#138: Achieved Strategic Acquisition Just 2 Years After Launch - Brian Kesselman

#137: Her Amazing Story of 0-$30M ARR with No Outside Funding - Rebecca Shostak

#136: Practical Founder Has Big Exit and Un-Retires to Build 2nd SaaS Success - Brian Dosal

#135: Vertical SaaS Investor Shares Proven Paths to Scale Up Big – Dave Yuan

#134: When It's Time to Close: Helping Founders Shut Down Right – Dori Yona

#133: Bootstrapper Sells School Fundraising Platform to PE Investors - Howard Gottlieb

#132: Bootstrapper Serving Private Equity Firms Acquired by PE-Backed Strategic – Richard Change

#131: No-Code SaaS Platform Bootstrapped to 75,000 Customers – Rachit Khator

#130: Profitable Product-Led Growth to $30 Million Before Big Exit – Joe Hyrkin

#129: On Freedom and Ownership With Software Entrepreneur Brian Hamilton

#128: Solving a Challenging SaaS Growth Puzzle - Scott Desgrosseilliers

#127: Scaling SaaS with Efficient Growth and Practical Funding - Bryan Forrester

#126: Jason Fried on 20 Years Bootstrapping BaseCamp at 37signals

#125: Created the World's Largest Subscription Service for Creative Design – Russ Perry

#124: From Services to SaaS Products to a Successful Acquisition in India - Sunando Bhattacharya

#123: How Practical Founders Are Winning Big with Growth Equity Funding – Growth Street Partners

#122: Going Long With Profitable Embedded Accounting Software After 13 Years – Raj Bhaskar

#121: Avoided a VC Round Using Royalty-Based Funding With No Equity Dilution – Vince Hsieh

#120: Practical Founder Exits for $300 Million Cash with Identity Verification Platform – Bill Spruill

#119: Growing His Third Side Gig SaaS Venture After Selling His First Two – Troy Munson