#118: The Silent PLG Killers: Why Smart Founders Fail at Product-Led Growth – Wes Bush

Wes Bush is CEO of ProductLed, a coaching and education company that has helped almost 500 serious SaaS founders to succeed with product-led growth strategies, tactics, and execution. These include … Listen to this episode

#117: Bootstrapped to 9 Figure Exit in Online Education for Real Estate – Michael McAllister

Michael McAllister is the founder and former CEO of The CE Shop, the leading provider of pre-licensing and continuing education for real estate professionals in the U.S. Michael started The … Listen to this episode

#116: The Do’s and Don’ts of Succeeding with Offshore Software Development – Matt Watson

Last year I interviewed three-time software founder Matt Watson on this podcast about his successful practical founder journeys. Matt leveraged offshore software development talent in his last two SaaS companies … Listen to this episode

#115: The SaaS Startup Success Where “Build It And They Will Come” Actually Worked – Quickli

Eric Dill was a successful mortgage broker in Sydney, Australia, who struggled with the same painful problem as every other broker: manually checking with multiple banks to validate and price … Listen to this episode

#114: Practical Founder Plays to Win Among Giant Partners and Competitors – Guy Rubin

Guy Rubin is the co-founder and CEO of Ebsta, a revenue intelligence platform that works with Salesforce and Hubspot to automatically analyze existing data to improve sales performance. Started in … Listen to this episode

#113: Grew and Sold a Simulation Learning Platform for Higher Education – Stu Draper

Stuart Draper founded Stukent, an innovative ed-tech company that provides simulated internships for business students. Stukent started by focusing on high-quality digital marketing education for colleges and universities using up-to-date … Listen to this episode

#111: Bootstrapped Then Raised VC Funding Before Selling to Salesforce for $250 Million

John Stewart created and sold an engineering services business, then grew a Salesforce integration services company before building some early software products. One of their software experiments allowed Salesforce customers … Listen to this episode

#110: Created a Fast-Growing SaaS Business Out of His Services Businesses – Landon Taylor

Landon Taylor created two successful digital marketing services businesses before embarking on a product-powered business with recurring revenues. His first agency drove traffic to its customers, which led to his … Listen to this episode

#109: Helping SaaS Startups Grow with Practical Funding and Operational Services – Kyle York

Kyle York was the Chief Revenue Officer of Dyn, a bootstrapped cloud infrastructure company that he helped grow and sell to Oracle for over $600 million. He then led product … Listen to this episode

#108: Grew His Vertical SaaS Business for 5 Years and Sold It for a Big Prize – Mike Kovarik

Mike Kovarik is the founder and former CEO of Attribytes, a software company he started, grew, and successfully sold in just over five years. Mike was a data analytics leader … Listen to this episode

#107: Brothers Sold Their Bootstrapped Software Company for $40 Million – David and Chris Sinkinson

Brothers David and Chris Sinkinson attended Queen's University in Ontario, Canada, when David learned of the problems maintaining the blue emergency phones on campus. He proposed a location-aware mobile safety … Listen to this episode

#106: SaaS Pricing Expert Shares Useful Strategies for Practical Founders – Dan Balcauski

Dan Balcauski is the founder and principal consultant of Product Tranquility, a SaaS pricing consultancy. Dan shares the core building blocks of SaaS pricing, including customer segments, value, competition, and … Listen to this episode

#105: Husband and Wife Team Built Popular Software for Wedding Planner Pros – Rob Farrow

Rob Farrow was an experienced marketing executive and his wife Christina Farrow was a successful professional wedding planner. They discovered there was no good software for wedding planner pros, so … Listen to this episode

#104: Turning VC-Funded Startups Into Profitable, Thriving SaaS Companies – Krista Morgan

Krista Morgan started her first tech company by raising funding and trying to grow very fast. When the company faced a big issue and failed, she learned that big funding … Listen to this episode

#103: Healthcare Software Startup Sold to VC-Funded Competitor During COVID Era – Ian Manners

Ian Manners was a successful consultant for pharmaceutical companies in the US when he discovered a major problem that needed a software solution. Big pharma companies provide financial assistance funding … Listen to this episode

#102: Practical VC Shares Advice for SaaS Founders From Over 2000 Investments – Dave Lambert

Dave Lambert and his team at Right Side Capital Management are the most active venture capital investors, having invested in over 2,000 startups since 2012. Right Side Capital is a "pre-VC" … Listen to this episode

#101: Bootstrapped Founder Has No Intention of Selling Even as They Grow Big – Todd Watson

Todd Watson is the owner and CEO of Showit, a popular no-code website builder and platform for designers and photographers. Todd is a native of Phoenix, Arizona where he started … Listen to this episode

#100: She Scaled Her Software App as a Successful Franchised Service Business – Erin Fletter

Erin Fletter had a long career in the restaurant business before starting an after-school enrichment program to teach kids how to cook at her daughters' school in 2011. Her cooking … Listen to this episode

#99: What VCs Don’t Tell Founders About Raising Big Funding (Part 2 of 2) – Greg Head

In this second of two episodes, Practical Founders Podcast host Greg Head discusses the next five important things venture capital investors don't tell new SaaS startup founders. Greg emphasizes that … Listen to this episode

#98: What VCs Don’t Tell Founders About Raising Big Funding (Part 1 of 2) – Greg Head

In episode 1, Practical Founders Podcast host Greg Head discusses the most important things that venture capital investors don't tell new SaaS startup founders. He emphasizes that VCs invest in … Listen to this episode

#97: Bootstrapped Auto Dealer Software and Sold to Private Equity Buyer – Mike Trasatti

Mike Trasatti spent 10 years in the automotive dealer software business before he found an auto dealer in Iowa who had built is own complete software system. They partnered up … Listen to this episode

#96: Expert Explains Payments Monetization For Your SaaS Business – Brian Abernethy

Brian Abernethy, founder of Utopaya, is an expert in helping SaaS leaders navigate the complicated process of adding payments monetization to their product offerings and business strategies. With a long … Listen to this episode

#95: Bootstrapped, Scaled, and Sold a Great Tech-Enabled Services Business – Jeff Corn

Jeff Corn is the co-founder and former CEO of Virtuance, one of the US's leading real estate photography and marketing providers. In 2010, Jeff was in the real estate investment … Listen to this episode

#94: Practical M&A Advisor Shares SaaS Valuation and Acquisition Trends – Adam Haynes

Adam Haynes is a managing director at GLC Advisors, an M&A advisory firm that helps bootstrapped founders sell their companies successfully. The GLC software advisor team has been working with practical … Listen to this episode

#93: SaaS Sales Coach Shares How to Improve Your Demo Close Rate – Matt Wolach

Matt Wolach spent 15 years as a successful SaaS account rep, sales leader, and software founder before becoming a SaaS sales coach for early-stage B2B SaaS companies. He has worked … Listen to this episode

#92: Bootstrapped Integration Platform Growing Faster by Niching In and Doubling Down – Charlie Alsmiller

Charlie Alsmiller is the founder and CEO of APIWORX, a powerful integration platform for mid-sized ecommerce companies. Charlie is an experienced, practical founder who has created and grown several software … Listen to this episode

#91: How AI Is Changing the Game for Practical SaaS Founders – David Evans

David Evans, the managing partner of Sentiero Ventures, a seed fund focused on AI-focused software startups. David discusses the role of AI in software development and the opportunities it presents … Listen to this episode

#90: Growth Equity Can Be Practical Funding for Founders Who Are Scaling Up Efficiently – Phil Dur

Phil Dur is cofounder and managing partner of PeakSpan Capital, a growth equity investment firm that works with bootstrapped SaaS founders who are scaling up to become sizable market leaders. … Listen to this episode

#89: Scrappy Bootstrappers Grew Up to Be the Enterprise Leader in Their Market – Joe McMenemon

Joe McMenemon and his college roommate, Brendan, knew they wanted to start a business together. They had run their college fraternity chapter and saw the problem of managing members and … Listen to this episode

#88: Persevered to Find a Scalable Niche in a Crowded Software Market – Jeromy Wilson

Jeromy Wilson spent over ten years in the software business as a product management leader working for PE-owned and VC-funded software companies. When he decided to start his own software … Listen to this episode

#87: Created Software for Their Own Business That is Changing Their Industry – Paul Van Metre

Paul Van Metre was the co-founder of a successful machine shop that manufactured custom parts for the aerospace and medical device industries. Over 15 years, they created and improved software … Listen to this episode

#86: Growing Profitably and Getting Big with Happy Founders After 18 Years – Chris Savage

Chris Savage is the co-founder of Wistia, a leading video marketing platform for businesses. Wistia was started in 2007 by Chris and a college friend when inexpensive cloud hosting and … Listen to this episode

#85: Moz Founder Reveals the Pains of VC Funding and an Alternative Funding Approach – Rand Fishkin

Rand Fishkin is the founder and former CEO of Moz, a leading SEO software for marketers created in 2007 that grew out of the active followers of Rand's popular SEOmoz … Listen to this episode

#84: Scaled and Sold a Marketplace of Pre-Vetted Freelancers – Nathan Hirsch

Nathan Hirsch, co-founder of FreeUp, shares his journey of building and selling the company and his other business adventures. FreeUp provides clients with pre-vetted virtual assistants (VAs) and freelancers in … Listen to this episode

#83: Second-Time Founder Grows Amazon Affiliate Marketing Platform to $3M ARR in One Year – Ian Brodie

Ian Brodie, the co-founder and CEO of Levanta, shares his journey of building a successful SaaS company in the affiliate marketing space. Levanta is an affiliate marketing platform for Amazon sellers, … Listen to this episode

#82: Former SaaS Founder Launches Seed Fund for Capital-Efficient Growers in Phoenix – Gregg Scoresby

Gregg Scoresby founded CampusLogic in Phoenix in 2021 to provide software for colleges and universities in the US to make it easier for students to apply for college loans and … Listen to this episode

#81: Bootstrapped Founder Sells His Profitable SaaS Company with $4.6 Million ARR – Esben Friis-Jensen

Esben Friis-Jensen and his cofounder, Sebastian Seilund, teamed up in 2021 to create Userflow, a no-code user onboarding product for SaaS companies. This week, it was announced that Userflow has … Listen to this episode

#80: Second-Time Founder Wins Bigger with Bootstrapped SaaS Company – Antony Ceravolo

Antony Ceravolo is a successful two-time startup founder from Adelaide, South Australia. He started his career in investment banking but left in 2002 to start a DVD rental business in … Listen to this episode

#79: Practical Founder with 3 Exits Explains How SEO Can Drive Efficient Growth – Raj Khera

Raj Khera is an experienced practical SaaS founder who has used search engine optimization (SEO) to grow businesses very efficiently. Now he coaches entrepreneurs at MoreBusiness on how to use … Listen to this episode

#78: Fast-Growing K-12 Education Software Company Will Be Profitable This Year – Justin Hewett

Justin Hewett started in the software business as a territory sales manager for an education software company in Utah. The company grew and Justin eventually led the sales team as … Listen to this episode

#77: Bootstrapped and Winning in Season Ticket Management Software – Morgan Katz

Morgan Katz is the founder and CEO of Ticketnology. Morgan was an enthusiastic athlete with a degree in sports management who started her career in ticket sales for sports teams … Listen to this episode

#76: Real Estate Investor Built Her Own CRM Solution and Created a Market Leader – Stephanie Betters

Stephanie Betters was a practicing Nurse Practitioner in heart surgery and an active real estate investor when her frustration with disparate real estate CRM and marketing solutions hit a boiling … Listen to this episode

#75: Bootstrapped a Digital Health Platform to Global Scale with 200 Employees – Shameem Hameed

Shameem Hameed created several companies, including a medical billing services company, before starting ZH Healthcare in 2008 to provide billing and EHR software to innovative healthcare providers. Their BlueBriX software … Listen to this episode

#74: Practical Holding Company Acquires Profitable SaaS Businesses – Kevin McArdle

Kevin McArdle spent 15 years working in large software companies before becoming a practical investor and acquirer of very small SaaS businesses. Kevin is the CEO and co-founder of Big … Listen to this episode

#73: Bootstrapped to a Successful $67 Million Exit with Medical Billing Solutions – Harry Hopkins

Harry Hopkins is co-founder and CIO of Viewgol, a medical billing technology software and services company based in Dallas, Texas. Viewgol was started in 2017 by three founders who got … Listen to this episode

#72: Serial Entrepreneur Funded His Biggest Idea Yet From His Other Businesses – Hamed Mazrouei

Hamed Mazrouei owned a security monitoring business and other businesses for many years before he started his first software and services business called Vivant Corporation. Vivant provides a complete turnkey … Listen to this episode

#71: Bootstrapped the Core Software that Runs Complex Manufacturing Plants – Subramanyam Kasibhat

Subramanyam Kasibhat has created dozens of products in many different industries. He and his wife were contracted by a friend to build a software solution for a manufacturing plant for … Listen to this episode

#70: Bootstrapped to $3M and Raised a VC Round Before a $200M PE Transaction – Jafar Owainati

Jafar Owainati was a mechanical engineer before he got an MBA in entrepreneurship and decided to start a software company with two friends. They looked at many ideas before building … Listen to this episode

#69: Bootstrapped a Fintech Payments Platform to $10M ARR in 3 Years – Miles Schwartz

Miles Schwartz a cofounder of Zūm Rails, a fast-growing fintech based in Canada with a growing worldwide presence. In just 3.5 years and without any outside funding, Zūm Rails has … Listen to this episode

#68: Bootstrapped and Sold a Successful Startup in Latin America – Bernardo Carvalho Wertheim

Bernardo Carvalho Wertheim is a worldly entrepreneur who grew up in Rio de Janeiro, Brazil, and then moved to the UK to go to school and start his career in … Listen to this episode

#67: Solo Founder Successfully Grew and Sold His Healthcare Software Company – Patrick Randolph

When Patrick Randolph discovered that doctors' offices lose 20% of appointments due to patient cancellations and no-shows, he set out to design and test a solution. QueueDr was created to … Listen to this episode

#66: Serial SaaS Founder Had Three Successful Exits in Three Different Ways – Raj Khera

Raj Khera has had three exits in his long career as a software entrepreneur and leader. His first company, GovCon, grew in the late 1990s to help government contractors easily … Listen to this episode

#65: The Bootstrapped Rocket-Ride Success Story of HighLevel – Robin Alex

Robin Alex worked in a digital marketing agency in Dallas when he discovered their small business clients struggled to nurture and follow up with their website leads. In 2018, Robin … Listen to this episode

#64: Bootstrapped, Very Profitable and Still Having Fun after 18 years – Mike Roberts

Mike Roberts is the founder and CEO of SpyFu, a leading competitive research tool for marketers and entrepreneurs with over 15,000 paid customers and hundreds of thousands of free users. … Listen to this episode

#63: Successfully Scaling Up a Bootstrapped Vertical SaaS Business – Raution Jaiswal

Raution Jaiswal grew up in India and then worked in management roles at large companies in the US before he discovered a problem experienced by small insurance agencies. He validated … Listen to this episode

#62: She Quit Her CPA Job to Create This Fast-Growing SaaS Startup – Kelly Mann

Kelly Mann was a CPA and auditor for 15 years before leaving her employer to start her own CPA firm focused on 401K benefits audits. She discovered a need to … Listen to this episode

#61: Sold His Bootstrapped SaaS Company for 16X Revenues – Praveen Ghanta

Praveen Ghanta graduated from MIT with degrees in computer science and economics and worked for various financial services companies after trying his hand at a software startup. Working in his … Listen to this episode

#60: Created a Practical Venture Studio After Selling His SaaS Company – Oliver Low

Oliver Low worked for Microsoft and then MySpace in London before creating a successful digital agency in 2010 with two friends. Their agency grew fast and was profitable, so they … Listen to this episode

#59: Using Royalty-Based Financing for Non-Dilutive SaaS Funding – Vik Thapar

In this expert interview, Vik Thapar of Cypress Growth Capital explains revenue-based financing (RBF) and how it can be very useful for practical SaaS founders. In the last 10 years, Vik … Listen to this episode

#58: Bootstrapped a successful lawncare services marketplace – Bryan Clayton

Bryan Clayton is the co-founder and CEO of GreenPal, a leading on-demand marketplace of lawn care services for homeowners across the US. With a team of 25 remote employees, they … Listen to this episode

#57: Finance, Accounting, and SaaS Metrics Basics for Practical Founders – Ben Murray

Ben Murray is a former SaaS CFO and finance professional who helps SaaS founders understand the basics of SaaS accounting, finance, and metrics for their growing businesses. Ben has a … Listen to this episode

#56: Technical Founder Shares Deep Learnings From His Many Startups – Wissam Tabbara

Wissam Tabbara is a serial entrepreneur who has created multiple software startups in Seattle since 2009 when he left Microsoft where he was a software development manager. He led multiple … Listen to this episode

#55: Bootstrapped to $10M ARR with Community-Led Growth and Services – Lloyed Lobo

Lloyed Lobo is the co-founder and former president of Boast.ai, a leading platform to help software companies in the US and Canada redeem available government tax credits. Technology-powered Boast.ai was launched … Listen to this episode

#54: Wound Down a Bootstrapped $1M SaaS Startup When the Market Changed – Ryan Goodman

Ryan Goodman joined the startup in the early days of the business intelligence and analytics market in 2003 as a specialist helping large customers adopt this new technology. This startup … Listen to this episode

#53: Insights and Lessons from the First Year of the Practical Founders Podcast – Greg Head

As the host of the Practical Founders Podcast, I have interviewed 46 successful SaaS founders and 6 savvy experts in the first year of weekly episodes. In this episode, I … Listen to this episode

#52: Successful Roofing Contractor Creates Fast-Growing $20M Vertical SaaS Business – Patrick Fingles

Patrick Fingles grew a successful roofing company with hundreds in the Baltimore-Washington DC area. In 2013, they created software to help new salespeople estimate, quote, and close new roofing sales. … Listen to this episode

#51: Scaling His Bootstrapped SaaS Company with Happy Founders and Happy Employees – Jordan Fleming

Jordan Fleming grew up in Toronto and New York,  then lived in Edinburgh, Scotland for 15 years where he created a successful consultancy helping larger businesses automate and improve their … Listen to this episode

#50: Serial Bootstrapper Sold Two Companies to eBay and Won Very Big – Gregory Shepard

Gregory Shepard is a serial entrepreneur who has created and sold 12 companies, including marketing software and ad technology companies. In 2016, he sold two of his bootstrapped software companies, … Listen to this episode

#49: Practical Investor Explains the Growth Equity Funding Game – Deepak Sindwani

Deepak Sindwani is a former software entrepreneur who has been a professional investor in software companies for over 20 years. Deepak is the co-founder and managing partner of Wavecrest Growth … Listen to this episode

#48: Built, Grew, Sold, and Kept Growing a Construction Software Company – Sam Knight

Sam Knight is the co-founder and former president of BOLT Software, a project management and scheduling software for the construction trades that build residential homes. Sam helped lead the BOLT … Listen to this episode

#47: How to Win Big When Selling Your SaaS Company for Under $50 million – Chris Kern

Chris Kern is an expert independent M&A advisor who has helped over 150 growing tech companies get financing, obtain investment, or sell their companies. He is Managing Director of Windstream … Listen to this episode

#46: Founding Couple Creates Caluable Company, Big Exit, and Family Life Too – Joshua Strebel

Joshua Strebel started a small SEO and website agency in the early 2000s after graduating from university. Joshua and his wife Sally experimented with website hosting using WordPress with low … Listen to this episode

#45: Bootstrapped Founder Still Creating Big Industry Impact 30 Years In – Dave Savage

Dave Savage was a top-producing mortgage loan officer in the early 1990s who used computers and software to help him sell more. He became a software entrepreneur by creating a … Listen to this episode

#44: Helping Seniors Tell Their Stories and Fight Loneliness with Easy Apps – Beth Sanders

Beth Sanders was selling computer software and equipment for a regional computer retailer in Ohio when she recorded her grandmother's life stories on a tape recorder. It was so powerful … Listen to this episode

#43: A Tenacious Bootstrapper’s Journey to a Profitable and Sustainable SaaS Business

Josh Haynam grew up in the Central Valley of California just 100 miles from the tech center of Silicon Valley without any awareness of tech jobs or tech businesses when … Listen to this episode

#42: Second-Time Founder Scaling Past $3 Million ARR with 3 Employees

Esben Friis-Jensen was a technology professional in Copenhagen, Denmark before he and three Danish friends moved to San Francisco in 2013 to start a new startup called Cobalt. Cobalt.io grew … Listen to this episode

#41: Product Feature Experiment Turns into a Valuable Standalone SaaS Company – Massimo Arrigoni

Massimo Arrigoni grew up in Milan, Italy, and moved to California 27 years ago to create software products and start a family, eventually moving to the San Francisco area in … Listen to this episode

#40: How SaaS Startups Can Grow Sales Successfully With SDRs and BDRs – Christine Rogers

"My B2B SaaS startup needs just more warm leads. But we have struggled when we hire junior salespeople to call on and email cold prospects to generate qualified leads that … Listen to this episode

#39: Former VC and Funded CEO Helps Founders Grow Lasting Companies Without VC funding – Dave Whorton

Dave Whorton is an experienced tech investor and funded founder who spent the first 20 years of his career at the highest levels of Silicon Valley venture capital and tech-boom … Listen to this episode

#38: Spinout SaaS Platform for Real Estate Brokerages Reaches $50 million – York Baur

Windermere Real Estate is a large and well-known residential real estate broker in the Seattle area. In the late 1990s, they invested to build an internal software system to power … Listen to this episode

#37: Bootstrapped for 10 years and Sold ProfitWell for $200 million – Patrick Campbell

Patrick Campbell wasn't expecting to be an entrepreneur when he grew up, but after his first few jobs, he struck out on his own in 2012 to create a software … Listen to this episode

#36: His First Company had Big VC Funding, But Not his Second Software Company – Jon Nordmark

Jon Nordmark founded eBags.com in 1998 as one of the first Internet e-commerce companies and grew it into the largest online retailer of luggage, bags, and travel accessories. Jon was … Listen to this episode

#35: From Website Designer to Industry SaaS Platform to a Successful Acquisition – Perry Rosenbloom

Perry Rosenbloom moved to Boulder, Colorado, in 2011 and started a small business offering digital marketing and custom website services. After building a website for his mother-in-law, an independent therapist, … Listen to this episode

#34: Sold his Tech Services Company to Invest in Big Vision for His BI Analytics Products – Gopal Krishnamurthy

Gopal Krishnamurthy was an early BI and data analytics expert working for a large company when he left to start a BI consulting company called Visual BI in 2010. Visual … Listen to this episode

#33: Bootstrapped a CRM for Auto Dealers that Sold for $150 million – Matt Watson

Matt Watson was a two-time software company with two successful exits before he was 40 years old. He started his first company, VinSolutions, in his basement in Kansas City in … Listen to this episode

#32: From her Kitchen Table to Global HR Employee Relations SaaS leader – Deb Muller

Deb Muller was an experienced HR executive at a large global company who left her job to start a consultancy specializing in managing important employee incident investigations. Surprisingly, her customers … Listen to this episode

#31: Bootstrapped to $30 Million and Still Growing Their Survey Tool and Research Platform – Vivek Bhaskaran

Vivek Bhaskaran was a computer science student in college who worked on an online survey project for a professor in the marketing department. After university, he built a new survey … Listen to this episode

#30: Bootstrapped IT Mgt. Software to Over $10 Million in Annual Sales – Scott McCausland

Scott McCausland was an experienced software sales leader who decided to go out on his own in 2008 to build a new software business. His technical cofounder built the first … Listen to this episode

#29: Mobile App Developer Created a Software Platform to Grow Faster – Oliver Palmer

Oliver Palmer helped start a mobile app development agency in Sydney, Australia that built simple apps for early mobile phones. When the iPhone launched, Tigerspike grew very fast by creating … Listen to this episode

#28: Bootstrapped B2B SaaS Company in India Serving IT Services Companies – Sandeep Kumar

Sandeep Kumar quit his job working for an Indian consulting company to start a software company in 2005, when product-focused startups were not common in India. For the next 10 … Listen to this episode

#27: Bootstrapped to Over $3M ARR with Software for SaaS Product Managers – Sarah Hum

Sarah Hum studied graphic design in university before she discovered she loved to help software startups create new products. She moved to Silicon Valley to work at Facebook as a … Listen to this episode

#26: His SaaS Business is Scaling Fast by Helping Other Businesses to Grow – Mark Abbott

Mark Abbott was an active investor and board member for 20 years when he realized that most of the 100+ companies he helped were not good a their "business fundamentals." … Listen to this episode

#25: Bootstrapped a Global SaaS Business in Scotland for a Massive Niche Market – Craig Letton

Craig Letton quit his corporate sales job in 2011 to take over his parents' small printing business in Scotland. It was his first time running a business and he learned … Listen to this episode

#24: Bootstrapped Event Registration Platform for Triathlons and Running Races – Jeff Matlow

Jeff Matlow is a serial entrepreneur and a crazy triathlete and long-distance runner who found a way to put those passions together in a crazy software startup. He saw an … Listen to this episode

#23: Creating Massive Impact with a Specialized School Fundraising Platform – Howard Gottlieb

Howard Gottlieb created and sold several businesses before starting a school fundraising website in 2003 called Easy Fundraising Ideas. It grew into the most popular Internet website for school fundraisers. … Listen to this episode

#22: Grew a niche vertical startup into a global industry leader – Scott Pickard

Scott Pickard didn't know he was embarking on a 15-year software entrepreneurial journey when he signed on to manage a horse veterinary practice in Calgary, Canada. But they had built … Listen to this episode

#21: Bootstrapped in Australia Then Moved to the US to Grow Much Bigger – Josh Cameron

Josh Cameron and three university friends started a scrappy software company in Brisbane Australia just after graduating. They had run the popular college bar where they discovered there was no … Listen to this episode

#20: Grew On-Demand Marketplace Out of a Search Marketing Agency – Joe Griffin

Joe Griffin recently left his job of 8 years as co-CEO of ClearVoice, a company that he and co-founder Jay Swanson started in 2014 out of their digital marketing agency … Listen to this episode

#19: Practical VC Seed Investor Explains the Institutional Funding Game – John Francis

John Francis is a general partner at Stout Street Capital, a  venture capital fund based in Denver, Colorado. Stout Street has made 70 small seed and pre-seed investments in software … Listen to this episode

#18: Bootstrapped a Podcast Recording Platform to Scale in Silicon Valley – Zach Moreno

Zach Moreno was a full-stack developer and coding instructor in Northern California in 2015 when he discovered audio podcasts. There wasn't a remote podcast software for recording high-quality audio over … Listen to this episode

#17: Creatively Grew and Sold a Global Threat Intelligence Product with Practical Funding – Karl Swannie

Karl Swannie was a geographer working in the scenic city of Victoria, British Columbia, Canada, when he started analyzing social media data based on location. He quickly saw there was … Listen to this episode

#16: Growing from Scrappy Startup Founder to Scaling-up SaaS CEO – Brad Redding

Brad Redding calls his first startup a “successful failure.” It didn’t end well, but he learned several very important lessons that helped him be more successful with his second startup, … Listen to this episode

#15: Scrappy Startup Founder Changes the Way Cars Are Bought Online – Daniel Yuabov

 Daniel Yuabov was a 22-year-old IT manager in New York who wanted to buy a new car. He was so frustrated with the buying experience that he started a software … Listen to this episode

#14: Created her Second Software Company Around Her World-Traveling Life – Melissa Kwan of eWebinar

Melissa Kwan created her first software company in 2014 and then sold it in 2019. It was extremely difficult to start and even harder to grow, but it’s how she … Listen to this episode

#13: Founder with 2 Exits Shares How He Achieved Product-Market Fit Twice – Seth Radman of Crescendo and Upbeat

 Seth Radman created, grew, and sold two music app startups in his twenties. A saxophone player in his college marching band, Seth was passionate about helping musicians and school band … Listen to this episode

#12: Practical Investor Provides Savvy Help for Vertical SaaS founders – Dougal Cameron of Golden Section

Dougal Cameron created Golden Section to provide support and practical funding to SaaS founders with deep experience in select vertical markets. Their founder-first approach is different than the traditional VC … Listen to this episode

#11: Bootstrapped to Exit in 6 Years Against Funded Competitors – Sean Meister of M2M in Motion

Sean Meister was a sales professional and leader with a successful career selling hospital and medical supplies before he left to join his long-time friend who had a vision for … Listen to this episode

#10: From Scrappy Software Entrepreneur to Savvy SaaS CEO – Thomas Brown of E-Claim

Thomas Brown creatively bootstrapped his software company and ran it as a very small "lifestyle" business before committing to growing his SaaS business with a larger team. Thomas was an independent … Listen to this episode

#9: Bootstrapper Gets Practical Funding Before Getting Acquired for $22 Million – Nick Santora of Curricula

Nick Santora bootstrapped Curricula for five years with his co-founders before raising $3M in practical funding and then getting acquired in 2022 for $22 million. Nick and his co-founders quit their … Listen to this episode

#8: Bootstrapped to $100M Exit with Just One Employee – Jeremy Clarke of WebMerge

Jeremy Clarke created, grew, and sold his software company in a most unusual and successful way: He grew WebMerge to $5M revenue by just himself for 6 years before hiring his … Listen to this episode

#7: From consulting biz to serious SaaS exit in Silicon Valley – Luke Hohmann

Luke Hohmann was an engineering and product management leader at Silicon Valley startups before he became an acclaimed author and speaker in the enterprise software development world. He used funding … Listen to this episode

#6: Self-Funded his 3rd Venture to a Big Exit in 18 Months – Steve Gelley of wemlo

Steve Gelley created two successful businesses and learned important lessons before he and a cofounder self-funded a third startup that was acquired in only 18 months for a big prize. Steve … Listen to this episode

#5: Lessons and successes building products for developers – Hamid Shojaee of Axosoft

Hamid Shojaee is a technical founder and serial entrepreneur who created several software companies and dozens of products in the last 25 years. He sold his two software companies in … Listen to this episode

#4: Winning the Vertical Software Game with Steady Growth – Dan Jaffe of LawLytics

Dan Jaffe is the founder and CEO of LawLytics, a practical website marketing platform for small law firms. Dan was a practicing lawyer before he became an internet entrepreneur with … Listen to this episode

#3: From Bootstrapped Shipping Software Add-on to White Label Success – Rafael Zimberoff

Rafael Zimberoff was CEO of ShipRush, a software company he founded in 2001, then grew and eventually sold in 2017 to Descartes Systems Group for $17 million. Rafael started ShipRush … Listen to this episode

#2: Bootstrapped to $2 Billion Valuation in 10 years – Jonathan Cronstedt (JCron) of Kajabi

Jonathan Cronstedt, also known as JCron, was the president of Kajabi software from 2016 through 2021 as he helped the company grow past the early startup years. JCron is a … Listen to this episode

#1: Self-Funded Spinoff is Now a Software Growth Powerhouse – Todd Watson of Showit

Todd Watson is the owner and CEO of Showit, a popular no-code website builder and platform for designers and photographers. Todd is a native of Phoenix, Arizona where he started … Listen to this episode