Practical Founders Podcast
By Greg Head
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Category: Entrepreneurship
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Subscribers: 11
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Episodes: 188
Description
Tune into the Practical Founders Podcast with host Greg Head for weekly in-depth interviews with founders who have built valuable software companies--without big funding.
| Episode | Date |
|---|---|
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#189: How Lighter Capital Finances Bootstrapped SaaS Growth - Tanner Kovacevich
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Mar 27, 2026 |
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#188: The Practical Long Game: 25 Years Scaling QuestionPro - Vivek Bhaskaran
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Mar 20, 2026 |
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#187: Practical Rule of 40 Growth+Profits Still Works for SaaS Acquirers - Juan Ignacio Garcia Braschi
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Mar 13, 2026 |
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#186: The Grind Behind a Stellar SaaS Exit in the UK - Simon Swords
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Mar 06, 2026 |
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#185: Survived COVID and a PE Exit —A Travel Tech Founder's Journey - Steve Reynolds
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Feb 27, 2026 |
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#184: Fixing The Software Development Mess For Non-Technical Founders - Keith Shields
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Feb 20, 2026 |
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#183: Selling to the Gorilla: Snap's Strategic Exit to ICE Mortgage Tech - Will Caldwell
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Feb 13, 2026 |
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#182: Why Focus Beats Funding in Crowded SaaS Markets - Luigi Mallardo
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Feb 06, 2026 |
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#181: Why Systems (with AI) Scale Better Than People in SaaS - Jordon Comstock
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Jan 30, 2026 |
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#180: AI Is Not Killing Vertical SaaS - It's Practical Leverage - Deepak Sindwani
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Jan 23, 2026 |
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#179: Don't Sell Your SaaS Yet: Hire a CEO and Get Your Life Back - Tighe Burke
|
Jan 16, 2026 |
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#178: Approaching $20 Million ARR with 99% Annual Retention - Dan MacDonald
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Jan 09, 2026 |
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#177: Building Multi-product Vertical SaaS With a Tiny Team - Robin Eissler
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Jan 02, 2026 |
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#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head
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Dec 26, 2025 |
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#175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh
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Dec 19, 2025 |
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#174: Plateaus, Pivots, and Staying Profitable: Solving Practical SaaS Puzzles - Josh Ho
|
Dec 12, 2025 |
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#173: From COVID Boom to Bootstrap Mode: Hubilo's Refounder Story - Shailesh Hegde
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Dec 05, 2025 |
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#172: Why Long-Term Bootstrapping Still Works in Event Mgt. SaaS - Raju Patel
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Nov 28, 2025 |
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#171: Lessons from a 9-Year Bootstrap Journey to a Private Equity Exit - Dharshan Rangegowda
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Nov 21, 2025 |
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#170: Why Most SaaS Acquirers Still Want Profitable Growth in 2025 - Gaurav Bhasin
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Nov 14, 2025 |
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#169: Practical Pivot and Relaunch Created Profitable 200% Growth - Natalie Barbu
|
Nov 07, 2025 |
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#168: These Three Superpowers Set Practical SaaS Founders Apart - Greg Head
|
Oct 31, 2025 |
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#167: Practical Founders Brought in CEO to Scale Their Company - Darryl Pahl
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Oct 24, 2025 |
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#166: How Practical SaaS Founders Can Compete in the AI Economy - Vincent Serpico
|
Oct 17, 2025 |
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#165: How to Enjoy Being the CEO as Your SaaS Business Grows Bigger - Brett Gilliland
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Oct 10, 2025 |
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#164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta
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Oct 03, 2025 |
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#163: Anthony Pierri & Rob Kaminski of Fletch: Why All SaaS Founders Struggle with Positioning
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Sep 26, 2025 |
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#162: Practical Investor - What's Working Now in AI-Driven SaaS Growth - Dave Yuan
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Sep 19, 2025 |
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#161: When Co-Founders Need Relationship Therapy - Dr. Matthew Jones
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Sep 12, 2025 |
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#160: CPG Founder Turned Failure Into a Profitable SaaS Business - Yuval Selik
|
Sep 05, 2025 |
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#159: Co-Parenting App Reaches $10M ARR Through Pure Bootstrap Growth - Vince Mayfield
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Aug 29, 2025 |
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#158: $33M Growth Equity After Friends/Family Funding to $10M ARR - Alan Miegel
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Aug 22, 2025 |
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#157: Seven Years In Survival Mode: A VC-funded Founder's Warning - Zvi Band
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Aug 15, 2025 |
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#156: Bootstrapper Built Vertical CRM to $10M ARR with Co-founder Dad - Shoanak (Sean) Mallapurkar
|
Aug 08, 2025 |
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#155: SaaS Founder's Crazy Ride: Boom, Bust, Strategic Sale - Jesse Burrell
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Aug 01, 2025 |
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#154: 2nd-Generation CEO Modernizes Mom's Legacy Software Business - Brian Forbis
|
Jul 25, 2025 |
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#153: Bootstrapper Killed His First Company to Scale Up Bigger - Chris Brisson
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Jul 18, 2025 |
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#152: Practical SaaS CEO Stays On After 100% Cash Sale - Tracy Larson
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Jul 11, 2025 |
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#151: Facial Recognition SaaS for Casinos to Almost $10M in Revenue – Henry Valentino
|
Jul 04, 2025 |
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#150: Grew an Unsexy Small Software Biz Into a SaaS Powerhouse - Josh Turley
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Jun 27, 2025 |
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#149: How Partner-Led Sales Built A $7M Bootstrap SaaS Business - Sameer Narkar
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Jun 20, 2025 |
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#148: These Bootstrappers Sold Modern Digital LeadGen to Conservative German Businesses - Chris Erler
|
Jun 13, 2025 |
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#147: How a Philadelphia Insurance Agent Built the Uber of Surety Bonds - Aaron Steffey
|
Jun 06, 2025 |
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#146: This European SaaS Bootstrapper Raised $22M in Growth Equity Without Losing Control - Roy van den Broek
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May 30, 2025 |
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#145: Making Big Bold Bets with Patient Execution as a Bootstrapped Founder - Gopal Krishnamurthy
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May 23, 2025 |
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#144: From Founder-Led Sales to Scalable Go-To-Market in Vertical SaaS - Phil Stern
|
May 16, 2025 |
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#143: From Professional Services to a $30M SaaS Business with a PE Acquisition - Sean Hoban
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May 09, 2025 |
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#142: Why This 3x SaaS Founder Couldn't Stay Retired to Launch His New Al Startup - Josh LaSov
|
May 02, 2025 |
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#141: Inside Acquire.com's Process for Selling Sub-$5M SaaS Companies - Andrew Gazdecki
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Apr 25, 2025 |
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#140: The Anti-Silicon Valley Playbook: How Genius Monkey Built a $100M Ad Tech Business on Their Own Terms - Seth Hassell and Clint Ethington
|
Apr 18, 2025 |
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#139: Bootstrapped Founder is Getting Ready for the AI Wave at $20M ARR - Shalin Jain
|
Apr 11, 2025 |
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#138: Achieved Strategic Acquisition Just 2 Years After Launch - Brian Kesselman
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Apr 04, 2025 |
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#137: Her Amazing Story of 0-$30M ARR with No Outside Funding - Rebecca Shostak
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Mar 28, 2025 |
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#136: Practical Founder Has Big Exit and Un-Retires to Build 2nd SaaS Success - Brian Dosal
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Mar 21, 2025 |
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#135: Vertical SaaS Investor Shares Proven Paths to Scale Up Big – Dave Yuan
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Mar 14, 2025 |
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#134: When It's Time to Close: Helping Founders Shut Down Right – Dori Yona
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Mar 07, 2025 |
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#133: Bootstrapper Sells School Fundraising Platform to PE Investors - Howard Gottlieb
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Feb 28, 2025 |
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#132: Bootstrapper Serving Private Equity Firms Acquired by PE-Backed Strategic – Richard Change
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Feb 21, 2025 |
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#131: No-Code SaaS Platform Bootstrapped to 75,000 Customers – Rachit Khator
|
Feb 14, 2025 |
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#130: Profitable Product-Led Growth to $30 Million Before Big Exit – Joe Hyrkin
|
Feb 07, 2025 |
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#129: On Freedom and Ownership With Software Entrepreneur Brian Hamilton
|
Jan 31, 2025 |
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#128: Solving a Challenging SaaS Growth Puzzle - Scott Desgrosseilliers
|
Jan 24, 2025 |
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#127: Scaling SaaS with Efficient Growth and Practical Funding - Bryan Forrester
|
Jan 17, 2025 |
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#126: Jason Fried on 20 Years Bootstrapping BaseCamp at 37signals
|
Jan 10, 2025 |
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#125: Created the World's Largest Subscription Service for Creative Design – Russ Perry
|
Jan 03, 2025 |
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#124: From Services to SaaS Products to a Successful Acquisition in India - Sunando Bhattacharya
|
Dec 27, 2024 |
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#123: How Practical Founders Are Winning Big with Growth Equity Funding – Growth Street Partners
|
Dec 20, 2024 |
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#122: Going Long With Profitable Embedded Accounting Software After 13 Years – Raj Bhaskar
|
Dec 13, 2024 |
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#121: Avoided a VC Round Using Royalty-Based Funding With No Equity Dilution – Vince Hsieh
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Dec 06, 2024 |
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#120: Practical Founder Exits for $300 Million Cash with Identity Verification Platform – Bill Spruill
|
Nov 29, 2024 |
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#119: Growing His Third Side Gig SaaS Venture After Selling His First Two – Troy Munson
|
Nov 22, 2024 |
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#118: The Silent PLG Killers: Why Smart Founders Fail at Product-Led Growth - Wes Bush
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Nov 15, 2024 |
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#117: Bootstrapped to 9 Figure Exit in Online Education for Real Estate - Michael McAllister
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Nov 08, 2024 |
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#116: The Do's and Don'ts of Adding Offshore Software Development Talent – Matt Watson
|
Nov 01, 2024 |
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#115: The SaaS Startup Success Where "Build It And They Will Come" Actually Worked – Quickli
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Oct 18, 2024 |
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#114: Practical Founder Plays to Win Among Giant Partners and Competitors – Guy Rubin
|
Oct 11, 2024 |
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#113: Grew and Sold a Simulation Learning Platform for Higher Education - Stu Draper
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Oct 04, 2024 |
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#111: Bootstrapped Then Raised VC Funding Before Selling to Salesforce for $250 Million
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Sep 20, 2024 |
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#110: Created a Fast-Growing SaaS Business Out of His Services Businesses – Landon Taylor
|
Sep 13, 2024 |
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#109: Helping SaaS Startups Grow with Practical Funding and Operational Services – Kyle York
|
Sep 06, 2024 |
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#108: He Grew His Vertical SaaS Business for 5 Years and Sold It for a Big Prize – Mike Kovarik
|
Aug 30, 2024 |
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#107: Brothers Sold Their Bootstrapped Software Company for $40 Million – David and Chris Sinkinson
|
Aug 23, 2024 |
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#106: SaaS Pricing Expert Shares Useful Strategies for Practical Founders – Dan Balcauski
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Aug 16, 2024 |
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#105: Husband and Wife Team Built Popular Software for Wedding Planner Pros - Rob Farrow
|
Aug 09, 2024 |
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#104: Turning VC-Funded Startups Into Profitable, Thriving SaaS Companies – Krista Morgan
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Aug 02, 2024 |
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#103: Healthcare Software Startup Sold to VC-Funded Competitor During COVID Era – Ian Manners
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Jul 26, 2024 |
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#102: Practical VC Shares Advice for SaaS Founders From Over 2000 Investments – Dave Lambert
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Jul 19, 2024 |
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#101: Bootstrapped SaaS Founder Has No Intention of Selling Even as They Grow Big – Todd Watson
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Jul 12, 2024 |
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#100: She Scaled Her Software App as a Successful Franchised Service Business – Erin Fletter
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Jul 05, 2024 |
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#99: What VCs Don't Tell Founders About Raising Funding (Part 2 of 2) – Greg Head
|
Jun 28, 2024 |
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#98: What VCs Don't Tell Founders About Raising Big Funding (Part 1 of 2) – Greg Head
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Jun 21, 2024 |
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#97: Bootstrapped Auto Dealer Software and Sold to Private Equity Buyer – Mike Trasatti
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Jun 14, 2024 |
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#96: Expert Explains Payments Monetization For Your SaaS Business - Brian Abernethy
|
Jun 07, 2024 |
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#95: Bootstrapped, Scaled, and Sold a SaaS-like Tech-Enabled Services Business
|
May 31, 2024 |
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#94: Practical M&A Advisor Explains SaaS Valuations and Acquisition Trends – Adam Haynes
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May 24, 2024 |
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#93: SaaS Sales Coach Shares How to Improve Your Demo Close Rate – Matt Wolach
|
May 17, 2024 |
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#92: Bootstrapped Integration Platform Growing Faster by Niching In and Doubling Down – Charlie Alsmiller
|
May 10, 2024 |
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#91: How AI Is (and Isn't) Changing the Game for Practical SaaS Founders – David Evans
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May 03, 2024 |
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#90: Why Growth Equity is Practical Funding for Founders Who Are Scaling Up Efficiently – Phil Dur
|
Apr 19, 2024 |
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#89: Scrappy Bootstrappers Grew Up to Be the Enterprise Leader in Their Market - Joe McMenemon
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Apr 12, 2024 |
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#88: Persevered to Find a Scalable Niche in a Crowded Software Market – Jeromy Wilson
|
Apr 05, 2024 |
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#87: Created Software for Their Own Business that is Now Changing the Industry – Paul Van Metre
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Mar 29, 2024 |
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#86: Growing Profitably and Getting Big with Happy Founders After 18 Years – Chris Savage
|
Mar 22, 2024 |
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#85: Moz Founder Rand Fishkin Reveals the Pains of VC Funding and an Alternative Funding Approach
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Mar 15, 2024 |
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#84: Scaled and Sold a Marketplace of Pre-Vetted Freelancers – Nathan Hirsch
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Mar 08, 2024 |
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#83: Second-time founder grows Amazon affiliate marketing platform to $3M ARR in one year – Ian Brodie
|
Mar 01, 2024 |
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#82: Former SaaS Founder Launches Seed Fund for Capital-Efficient Growers in Phoenix – Gregg Scoresby
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Feb 16, 2024 |
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#81: Bootstrapped Founder Sells His Profitable SaaS Company with $4 Million ARR – Esben Friis-Jensen
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Feb 09, 2024 |
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#80: Second-Time Founder Wins Bigger with Bootstrapped SaaS Company – Antony Ceravolo
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Feb 02, 2024 |
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#79: Practical Founder with 3 Exits Explains How SEO Can Drive Efficient Growth – Raj Khera
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Jan 26, 2024 |
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#78: Fast-Growing K-12 Education Software Company Will Be Profitable This Year – Justin Hewett
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Jan 19, 2024 |
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#77: Bootstrapped and Winning in Season Ticket Management Software – Morgan Katz
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Jan 12, 2024 |
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#76: Real Estate Investor Built Her Own CRM Solution and Created a Market Leader – Stephanie Betters
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Dec 29, 2023 |
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#75: Bootstrapped Their Digital Health Platform to Global Scale with 200 Employees – Shameem Hameed
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Dec 22, 2023 |
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#74: Practical Holding Company Acquires Profitable SaaS Companies – Kevin McArdle
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Dec 15, 2023 |
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#73: Bootstrapped to successful $67 million exit with medical billing solutions – Harry Hopkins
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Dec 08, 2023 |
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#72: Serial entrepreneur funded his biggest idea yet from other businesses – Hamed Mazrouei
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Dec 01, 2023 |
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#71: Bootstrapped the core software that runs complex manufacturing plants – Subramanyam Kasibhat
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Nov 24, 2023 |
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#70: Bootstrapped to $3M and Raised a VC Round Before a $200M PE Transaction – Jafar Owainati
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Nov 17, 2023 |
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#69: Bootstrapped a Fintech Payments Platform to $10M ARR in 3 Years – Miles Schwartz
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Nov 10, 2023 |
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#68: Bootstrapped and Sold a Successful Startup in Latin America – Bernardo Carvalho Wertheim
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Nov 03, 2023 |
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#67: Grew and Sold a Profitable Healthcare Software Company – Patrick Randolph
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Oct 27, 2023 |
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#66: Serial SaaS Founder Had Three Successful Exits in Three Different Ways – Raj Khera
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Oct 20, 2023 |
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#65: The Bootstrapped Rocket-Ride Success Story of HighLevel – Robin Alex
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Oct 13, 2023 |
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#64: Bootstrapped, very profitable and still having fun after 18 years – Mike Roberts
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Oct 06, 2023 |
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#63: Successfully Scaling Up a Bootstrapped Vertical SaaS Business – Raution Jaiswal
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Sep 29, 2023 |
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#62: She Quit Her CPA Job to Create This Fast-Growing SaaS Startup – Kelly Mann
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Sep 22, 2023 |
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#61: Sold His Bootstrapped SaaS Company for 16X Revenues - Praveen Ghanta
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Sep 15, 2023 |
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#60: Created a Practical Venture Studio After Selling His SaaS Company – Oliver Low
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Sep 08, 2023 |
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#59: Using Royalty-Based Financing for Non-Dilutive SaaS Funding – Vik Thapar
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Sep 01, 2023 |
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#58: Bootstrapped a successful lawncare services marketplace – Bryan Clayton
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Aug 25, 2023 |
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#57: Finance, Accounting, and SaaS Metrics Basics for Practical Founders - Ben Murray
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Aug 11, 2023 |
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#56: Technical founder shares deep learnings from his many startups – Wissam Tabbara
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Aug 04, 2023 |
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#55: Bootstrapped to $10M ARR with community-led growth and services – Lloyed Lobo
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Jul 29, 2023 |
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#54: Wound down a bootstrapped $1M SaaS startup when the market changed – Ryan Goodman
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Jul 22, 2023 |
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#53: Insights and lessons from the first year of the Practical Founders Podcast – Greg Head
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Jul 14, 2023 |
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#52: Successful roofing contractor creates fast-growing $20M vertical SaaS business – Patrick Fingles
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Jun 30, 2023 |
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#51: Scaling his bootstrapped SaaS company with happy founders and happy employees – Jordan Fleming
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Jun 23, 2023 |
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#50: Serial bootstrapper sold two companies to eBay and won very big – Gregory Shepard
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Jun 16, 2023 |
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#49: Practical investor explains the growth equity funding game - Deepak Sindwani
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Jun 09, 2023 |
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#48 – Built, grew, sold, and kept growing a construction software company – Sam Knight
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Jun 02, 2023 |
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#47 – How to win big when selling your SaaS company for under $50 million – Chris Kern
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May 26, 2023 |
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#46 – Founding couple creates valuable company, big exit, and family life too
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May 19, 2023 |
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#45 – Bootstrapped founder still creating big industry impact 30 years in – Dave Savage
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May 12, 2023 |
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#44 – Helping seniors tell their stories and fight loneliness with easy apps – Beth Sanders
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May 05, 2023 |
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#43 – A tenacious bootstrapper's journey to a profitable and sustainable SaaS business
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Apr 28, 2023 |
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#42: Second-time founder scaling up with product-led growth and 3 employees
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Apr 21, 2023 |
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#41: A Product Feature Experiment Turns into a Valuable Standalone SaaS Company – Massimo Arrigoni
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Apr 14, 2023 |
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#40: How SaaS Startups Can Grow Sales Successfully With SDRs and BDRs - Christine Rogers
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Apr 07, 2023 |
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#39: Former VC and funded CEO helps founders grow lasting companies without VC funding – Dave Whorton
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Mar 31, 2023 |
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#38: Spinout SaaS platform for real estate brokerages reaches $50 million – York Baur
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Mar 24, 2023 |
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#37: Bootstrapped for 10 years and sold ProfitWell for $200 million – Patrick Campbell
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Mar 16, 2023 |
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#36: His first company had big VC funding, but not his second software company – Jon Nordmark
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Mar 10, 2023 |
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#35: From website designer to industry SaaS platform to a successful acquisition – Perry Rosenbloom
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Mar 03, 2023 |
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#34: Sold his tech services company to invest in big vision for his BI analytics products – Gopal Krishnamurthy
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Feb 24, 2023 |
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#33: Bootstrapped a leading CRM for auto dealers that sold for $150 million – Matt Watson
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Feb 17, 2023 |
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#32: From her kitchen table to global HR employee relations SaaS leader – Deb Muller
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Feb 10, 2023 |
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#31: Bootstrapped to $30 million and still growing their survey tool and research platform - Vivek Bhaskaran
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Feb 03, 2023 |
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#30: Bootstrapped IT mgt. software to over $10 million in annual sales before being acquired - Scott McCausland
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Jan 27, 2023 |
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#29: Mobile app developer created a software platform to grow faster – Oliver Palmer
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Jan 20, 2023 |
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#28: Bootstrapped B2B SaaS company in India serving IT services companies – Sandeep Kumar
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Jan 13, 2023 |
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#27: Bootstrapped to over $3M ARR with software for SaaS product managers – Sarah Hum
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Jan 06, 2023 |
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#26: His SaaS business is scaling fast by helping other businesses to grow – Mark Abbott
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Dec 30, 2022 |
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#25: Bootstrapped a global SaaS business in Scotland for a "massive niche" market
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Dec 16, 2022 |
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#24: Bootstrapped event registration platform for triathlons and running races – Jeff Matlow
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Dec 09, 2022 |
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#23: Creating massive impact with a specialized school fundraising platform – Howard Gottlieb
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Dec 02, 2022 |
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#22: Grew a niche vertical startup into a global industry leader – Scott Pickard
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Nov 25, 2022 |
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#21: Bootstrapped in Australia then moved to the US to grow much bigger – Josh Cameron
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Nov 18, 2022 |
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#20: Grew on-demand marketplace out of a search marketing agency – Joe Griffin
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Nov 11, 2022 |
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#19: Practical VC seed investor explains the institutional funding game – John Francis
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Oct 28, 2022 |
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#18: Bootstrapped a podcast recording platform to scale in Silicon Valley - Zach Moreno
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Oct 21, 2022 |
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#17: Creatively grew and sold a threat intelligence product with practical funding - Karl Swannie
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Oct 14, 2022 |
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#16: Growing from scrappy startup founder to scaling-up SaaS CEO - Brad Redding
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Oct 07, 2022 |
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#15: Scrappy startup founder changes the way cars are bought online - Daniel Yuabov
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Sep 30, 2022 |
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#14: Created her second software company around her world-traveling life - Melissa Kwan
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Sep 23, 2022 |
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#13: Founder with 2 exits shares how he achieved real product-market fit twice - Seth Radman
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Sep 16, 2022 |
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#12: Practical investor provides savvy help for vertical SaaS founders – Dougal Cameron
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Sep 09, 2022 |
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#11 - Bootstrapped to exit in 6 years against funded competitors - Sean Meister
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Sep 02, 2022 |
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#10: From scrappy software entrepreneur to savvy SaaS CEO - Thomas Brown
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Aug 26, 2022 |
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#9: Bootstrapper gets practical funding before getting acquired for $22 million - Nick Santora
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Aug 19, 2022 |
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#8: Bootstrapped to $100M exit with just one employee - Jeremy Clarke
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Aug 12, 2022 |
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#7: From consulting biz to serious SaaS exit in Silicon Valley - Luke Hohmann
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Aug 05, 2022 |
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#6: Self-funded 3rd venture to a big exit in 18 months - Steve Gelley
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Jul 29, 2022 |
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#5: Lessons and successes building products for developers – Hamid Shojaee of Axosoft
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Jul 22, 2022 |
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#4: Winning the vertical software game with steady growth - Dan Jaffe of LawLytics
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Jul 15, 2022 |
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#3: From bootstrapped add-on to white label success - Rafael Zimberoff of ShipRush
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Jul 08, 2022 |
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#2: Bootstrapped to $2 billion valuation in 10 years - Jonathan Cronstedt of Kajabi
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Jun 26, 2022 |
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#1: Self-funded spinoff to software growth powerhouse - Todd Watson of Showit
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Jun 19, 2022 |