Best Bootstrapper Podcasts (2025)

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#141: Inside Acquire.com's Process for Selling Sub-$5M SaaS Companies - Andrew Gazdecki 55:39

31m ago55:39

55:39

Andrew Gazdecki is the founder and CEO of Acquire.com, a marketplace of buyers and sellers of smaller, profitable SaaS products with revenues between $100,000 and $5,000,000. Andrew sold his own software company and learned how little support and information was available to sell a software product for under $5-10 million in deal size. Acquire.com …

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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 1:04:34

9d ago1:04:34

1:04:34

Seth Hassell and Clint Ethington are the co-founders of Genius Monkey, a programmatic ad tech platform with proven targeting, tracking, and attribution for optimized results. Seth and Clint were childhood friends who worked on many business ventures before launching Genius Monkey in 2009, leveraging their experience in digital ad technologies. Geni…

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#139: Bootstrapped Founder is Getting Ready for the AI Wave at $20M ARR - Shalin Jain 1:07:35

16d ago1:07:35

1:07:35

Shalin Jain is the founder and CEO of HappyFox, a successful bootstrapped company that provides modern help desk management software for customer service, support, and IT management organizations. Shalin and his small team in India built many successful products from 2000-2010, then focused on HappyFox and moved to the US in 2011. HappyFox is a mid…

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#138: Achieved Strategic Acquisition Just 2 Years After Launch - Brian Kesselman 1:00:15

23d ago1:00:15

1:00:15

Brian Kesselman is cofounder and now CRO of Skematic, a compliance management and workflow software for financial services firms. Brian was a lawyer for major financial services companies who helped manage internal compliance in this highly regulated industry. He took a job selling compliance software and broke sales records before starting Skemati…

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#137: Her Amazing Story of 0-$30M ARR with No Outside Funding - Rebecca Shostak 1:04:57

30d ago1:04:57

1:04:57

Rebecca Shostak is co-founder and chief brand officer of Flodesk, the popular email marketing software for small businesses that care about beautiful branded emails. After prototyping the product and validating the problem, they launched in 2019 with a viral explosion that still powers their bootstrapped growth. Six years later, Flodesk has over $3…

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#136: Practical Founder Has Big Exit and Un-Retires to Build 2nd SaaS Success - Brian Dosal 1:11:26

1M ago1:11:26

1:11:26

Brian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard for key metrics for the Managed Service Provider (MSP) industry. After his intense 9-year journey at BrightGauge, Bria…

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#135: Vertical SaaS Investor Shares Proven Paths to Scale Up Big – Dave Yuan 55:49

1M ago55:49

55:49

Dave Yuan is the founder of Tidemark, an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become “control points” in their markets and grow very big. Dave and Tidemark have invested in successful companies like Toast, ServiceTitan, Karbon and Dutchie. In this episode, Dave shares some of the most u…

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NO CASH, NO PROBLEM: HOW TO HUSTLE YOUR WAY TO THE TOP 1:17:27

2M ago1:17:27

1:17:27

Send us a text What does it really take to go from struggling to thriving? In this raw and motivating episode, e-commerce expert Zoe Khan shares her incredible journey from financial desperation to running a successful agency with over 100 employees. Zoe’s story starts with selling plasma just to afford a phone to apply for jobs. Juggling multiple …

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#134: When It’s Time to Close: Helping Founders Shut Down Right – Dori Yona 44:27

2M ago44:27

44:27

Dori Yona is co-founder and CEO of SimpleClosure, a technology- and people-powered company that helps founders wind down and dissolve a startup or business that is no longer viable. Shutting down a business can be complicated, costly, and risky for founders. SimpleClosure manages the unique processes with automation and expert support. SimpleClosur…

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#133: Bootstrapper Sells School Fundraising Platform to PE Investors - Howard Gottlieb 58:47

2M ago58:47

58:47

Howard Gottlieb started Read-A-Thon in 2012 as a reading-based fundraising platform that helped students raise money while boosting education. Their easy platform and simple fundraising approach created amazing results. The Read-a-Thon business grew steadily and profitably without any outside funding. Read-A-Thon helped over 4000 schools and studen…

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Foster Care Crisis: 80% of Death Row Inmates & 60% of Traffic Victims — A Call for Reform 55:35

2M ago55:35

55:35

Send us a text Foster care crisis, systemic neglect, shocking statistics, death row, traffic fatalities, urgent reform, social justice. Lisa’s journey is a testament to resilience and the power to create change. After enduring 36 foster homes and facing homelessness at 18, she refuses to let the system’s failures define her future. Now, she’s takin…

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#132: Bootstrapper Serving Private Equity Firms Acquired by PE-Backed Strategic – Richard Change 1:09:35

2M ago1:09:35

1:09:35

Richard Change is co-founder and CEO of PFA Solutions, the provider of FirmView software. FirmView® is the leading carry and compensation management platform for private equity investors to manage their internal compensation from fees and carried interest. Richard was a senior architect for a large private equity firm when he discovered this comple…

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#131: No-Code SaaS Platform Bootstrapped to 75,000 Customers – Rachit Khator 1:03:43

2M ago1:03:43

1:03:43

Rachit Khator is the founder and CEO of Stackby, a no-code spreadsheet and database app builder that allows business users to create powerful spreadsheet-like applications with data links, automations, and workflows. Rachit and his team of 34 employees live in Surat, India, north of Mumbai. Stackby started when Rachit was working for a corporate ve…

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ENTREPRENEURS: CAN FITNESS GIVE YOU THE EDGE? DR. SHELL HAS THE ANSWER! 1:01:20

3M ago1:01:20

1:01:20

Send us a text Want to build a thriving business? Start with your body. In this powerhouse episode, Dr. Shell—doctor, entrepreneur, and Bare Knuckle Fighting Championship competitor—shares how strength training and mental resilience give entrepreneurs the edge they need to win in business and life. Discover why fitness isn’t just about looking good…

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#130: Profitable Product-Led Growth to $30 Million Before Big Exit – Joe Hyrkin 1:07:58

3M ago1:07:58

1:07:58

Joe Hyrkin is the former CEO of Issuu, a content publishing platform for interactive marketing content. Issuu allows you to easily publish printable and PDF materials in various formats to websites and social media. It’s a global product-led success story with millions of customers and a successful and sustainable business. Issuu was started by fou…

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EMPOWERING ENTREPRENEURS TO THRIVE WITH PALOMA 1:22:16

3M ago1:22:16

1:22:16

Send us a text Thinking about starting a business but unsure where to begin? We’re here to help. Join us as we explore the key steps to building a strong foundation, featuring insights from Paloma, an experienced business attorney. We’ll break down the importance of choosing the right business structure—like an LLC—to protect your personal assets a…

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#129: On Freedom and Ownership With Software Entrepreneur Brian Hamilton 1:06:34

3M ago1:06:34

1:06:34

Brian Hamilton is one of America’s most successful entrepreneurs and a leading expert on entrepreneurship. Today, Hamilton serves as chairman of software company LiveSwitch. He is known for his pioneering work in fintech, his advocacy for small businesses, and his commitment to criminal justice reform. As the founder of Sageworks (now Abrigo), Amer…

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IS MONEY BLOCKING YOUR DREAM? HERE’S HOW TO BEGIN! WITH DAVEED BENITO 1:05:59

3M ago1:05:59

1:05:59

Send us a text People often focus on all the reasons why they can’t achieve something—lack of money, equipment, or confidence. But what if we flipped the script? Let’s talk about all the ways you can break through those barriers. 💡 We believe this is the moment for independent creators to rise, break the rules, and maybe even reshape the entertainm…

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#128: Solving a Challenging SaaS Growth Puzzle - Scott Desgrosseilliers 1:04:33

3M ago1:04:33

1:04:33

Scott Desgrosseilliers is the founder and CEO of Wicked Reports, a leading multi-touch marketing attribution software for SMBs who use paid online advertising. Scott is a data and analytics expert who saw the costly limitations of simple performance reports from popular ad platforms. Wicked Reports was started as a bootstrapped software company in …

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JUDGE LYNN TOLER: RELATIONSHIPS MAKE OR BREAK SUCCESS 1:00:57

3M ago1:00:57

1:00:57

Send us a text Prepare to be inspired by the incredible resilience and wisdom of Judge Lynn Toler, a trailblazer known for her impactful work on "Divorce Court" and "Marriage Boot Camp." We explore the remarkable story of her father, who, despite the odds stacked against him as a black man in a predominantly white industry, supported his family fro…

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#127: Scaling SaaS with Efficient Growth and Practical Funding - Bryan Forrester 1:11:52

3M ago1:11:52

1:11:52

Bryan Forrester is CEO of Boostlingo, a leading on-demand platform for language live interpretation services that is growing quickly and can become a very large company. Boostlingo now has 160 employees and over 17,000 language interpreters who use their software to manage jobs, coordinate schedules, deliver interpreting services, and get paid. Bry…

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#126: Jason Fried on 20 Years Bootstrapping BaseCamp at 37signals 57:57

4M ago57:57

57:57

Jason Fried is the co-founder and CEO of 37signals, makers of the popular Basecamp project management software, which is still growing and very profitable after 20 years. He is going long and still having fun as an engaged CEO, building great products with great marketing that stands out. Jason has long advocated for software founders to avoid VC f…

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#125: Created the World’s Largest Subscription Service for Creative Design – Russ Perry 1:08:10

4M ago1:08:10

1:08:10

Quote from Russ Perry, founder and CEO of Design Pickle “The game for practical SaaS founders really comes down to recognizing that there is a large market size for very boring niche companies. Finding that niche is the fastest path to success. Don’t be afraid to be boring and specific. “If I were to do Design Pickle all over again, I would have ju…

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#124: From Services to SaaS Products to a Successful Acquisition in India - Sunando Bhattacharya 1:05:41

4M ago1:05:41

1:05:41

Sunando Bhattacharya spent 13 years as a business leader in managed IT services companies in India before starting his own cloud tech services business. This company grew slowly and an opportunity arose to create a software product for one of their clients. Two years later, in 2019, they had a few more Apiculus product customers and focused more on…

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#123: How Practical Founders Are Winning Big with Growth Equity Funding – Growth Street Partners 57:37

4M ago57:37

57:37

Steve Wolfe and Nate Grossman are co-founders at Growth Street Partners, a growth equity firm focused on investing in early-stage B2B SaaS companies between $2M-$6M in ARR. They discuss how growth equity funding works for SaaS founders and how it allows entrepreneurs to maintain control while still benefiting from investment and liquidity. In this …

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#122: Going Long With Profitable Embedded Accounting Software After 13 Years – Raj Bhaskar 1:02:14

4M ago1:02:14

1:02:14

Raj Bhaskar is a successful two-time practical software founder with one exit. In 2000, he started his first software company, VisualHOMES, to provide a comprehensive financial management software to public housing agencies. With no outside funding, the business grew to serve 65 regional providers serving 2 million residents before Yardi Systems ac…

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#121: Avoided a VC Round Using Royalty-Based Funding With No Equity Dilution – Vince Hsieh 1:05:36

5M ago1:05:36

1:05:36

Vince Hsieh is a two-time entrepreneur who has started, grown, and sold two industrial tech companies that included software and either an RFID or GPS device in the solutions. His second venture, Geoforce, raised a non-dilutive funding round to accelerate global growth before being successfully acquired by private equity investors LLR Partners in 2…

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#120: Practical Founder Exits for $300 Million Cash with Identity Verification Platform – Bill Spruill 1:03:51

5M ago1:03:51

1:03:51

Bill Spruill had a successful sales and executive career with two exits before he and his cofounder struck out on their own in the location verification market serving financial and e-commerce companies. Sales grew slowly for several years as they scraped by and kept going. Eventually, they pivoted the company to focus on identity verification and …

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#119: Growing His Third Side Gig SaaS Venture After Selling His First Two – Troy Munson 1:03:48

5M ago1:03:48

1:03:48

Troy Munson has been a successful enterprise SaaS sales rep for several years, but he wanted more control over his life—and eventual financial independence. So he launched his own small startup on the side. He learned a lot and sold it before launching his second side gig software company, which he sold for a little bit more. He started his third s…

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#118: The Silent PLG Killers: Why Smart Founders Fail at Product-Led Growth - Wes Bush 1:04:23

5M ago1:04:23

1:04:23

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 freemium products and free trials, where the product itself creates the awareness, engagement, and enthusiasm to buy before any human intervention (aka …

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#117: Bootstrapped to 9 Figure Exit in Online Education for Real Estate - Michael McAllister 1:18:14

6M ago1:18:14

1:18:14

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 CE Shop in 2005 by distributing existing training materials from a continuing education provider. They quickly created their own online education solution and p…

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#116: The Do’s and Don’ts of Adding Offshore Software Development Talent – Matt Watson 55:34

6M ago55:34

55:34

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 to staff up quickly and grow efficiently. His top developers and designers were offshore in the Philippines, but they weren’t one-off cont…

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#115: The SaaS Startup Success Where “Build It And They Will Come” Actually Worked – Quickli 1:00:12

6M ago1:00:12

1:00:12

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 mortgages for homeowners. Eric and his good friend Angus Keatinge resolved to create a software product to solve this complicated and chronic problem. Quickli…

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#114: Practical Founder Plays to Win Among Giant Partners and Competitors – Guy Rubin 57:57

7M ago57:57

57:57

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 London in 2012, ebsta found success in the early days of the Salesforce marketplace and addon economy as a data tool integrated with customer emails. ebs…

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#113: Grew and Sold a Simulation Learning Platform for Higher Education - Stu Draper 1:08:09

7M ago1:08:09

1:08:09

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 digital textbooks and content. They then added a simulation system for students to practice their digital marke…

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#111: Bootstrapped Then Raised VC Funding Before Selling to Salesforce for $250 Million 57:55

7M ago57:55

57:55

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 to see and interact with their customer data on a map. When customers paid for it and revenue grew, he and his co-founder wou…

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#110: Created a Fast-Growing SaaS Business Out of His Services Businesses – Landon Taylor 1:02:57

8M ago1:02:57

1:02:57

Landon Taylor created two successful digital marketing services businesses before starting a product-powered business with recurring revenues. His first agency drove traffic to its customers, which led to his second business, Best Company, which produced qualified leads for large home services businesses through its bestcompany.com consumer review …

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#109: Helping SaaS Startups Grow with Practical Funding and Operational Services – Kyle York 1:06:26

8M ago1:06:26

1:06:26

Kyle York was the Chief Revenue Officer of Dyn, a bootstrapped cloud infrastructure that he helped grow and sell to Oracle for over $600 million. He then led product strategy and acquisitions in Oracle’s cloud infrastructure group before going out on his own to invest in SaaS startups and help them grow. York IE is both an advisory firm with tech-e…

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#108: He Grew His Vertical SaaS Business for 5 Years and Sold It for a Big Prize – Mike Kovarik 1:08:27

8M ago1:08:27

1:08:27

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 at large food distributors, where he discovered a chronic challenge with low-quality product data in their massive e-commerce systems. He quit his job, built a product with a …

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#107: Brothers Sold Their Bootstrapped Software Company for $40 Million – David and Chris Sinkinson 1:09:20

8M ago1:09:20

1:09:20

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 app, so Chris built it himself, and it worked great. AppArmor grew steadily to become the most popular university mobile safety platform in …

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#106: SaaS Pricing Expert Shares Useful Strategies for Practical Founders – Dan Balcauski 1:02:55

8M ago1:02:55

1:02:55

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 positioning strategy. Dan also describes the common mistakes in pricing and the importance of having structured pricing conversations with…

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#105: Husband and Wife Team Built Popular Software for Wedding Planner Pros - Rob Farrow 1:16:33

9M ago1:16:33

1:16:33

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 they decided to build software themselves. They invested their savings, built a loyal team, and started Aisle Planner to serve other wedding planner pr…

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#104: Turning VC-Funded Startups Into Profitable, Thriving SaaS Companies – Krista Morgan 1:02:49

9M ago1:02:49

1:02:49

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 was more of a problem than a help in the growth and wind-down processes. Krista is now CEO and General Partner of Stage Fund, an early-stage private equity fund that makes control …

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#103: Healthcare Software Startup Sold to VC-Funded Competitor During COVID Era – Ian Manners 1:05:18

9M ago1:05:18

1:05:18

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 for patients who require their drugs but struggle with high costs, but these funds are difficult to access and manage for patients and healthcare…

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#102: Practical VC Shares Advice for SaaS Founders From Over 2000 Investments – Dave Lambert 1:05:55

9M ago1:05:55

1:05:55

Dave Lambert and the team at Right Side Capital Management are the most active venture capital investors, having invested in over 2,000 startups since 2009. Right Side Capital is a “pre-VC” institutional investor that operates very differently from traditional VCs: investing when SaaS companies have just a little revenue using a submission form on …

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#101: Bootstrapped SaaS Founder Has No Intention of Selling Even as They Grow Big – Todd Watson 1:01:53

10M ago1:01:53

1:01:53

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 as a videographer before joining a friend in 2007 to create a scrappy software business that made inexpensive photo-presenting and sharing tools for photographers. The Show…

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#100: She Scaled Her Software App as a Successful Franchised Service Business – Erin Fletter 1:05:04

10M ago1:05:04

1:05:04

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 program became popular, and she improved and expanded it to become a paid program called Sticky Fingers Cooking. Soon, she had a sizable business with over 100 chef-inst…

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#99: What VCs Don’t Tell Founders About Raising Funding (Part 2 of 2) – Greg Head 31:44

10M ago31:44

31:44

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 VCs invest in very few businesses and seek big wins. He highlights the importance of understanding the game of venture capital funding and the alterna…

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#98: What VCs Don’t Tell Founders About Raising Big Funding (Part 1 of 2) – Greg Head 27:51

10M ago27:51

27:51

In this episode, Practical Founders Podcast host Greg Head discusses the most important things venture capital investors don’t tell new SaaS startup founders. He emphasizes that VCs invest in very few businesses and are looking for big wins. Greg highlights the importance of understanding the game of venture capital funding and the alternatives ava…

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#97: Bootstrapped Auto Dealer Software and Sold to Private Equity Buyer – Mike Trasatti 1:01:03

11M ago1:01:03

1:01:03

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 in 2008, and Mike became the first CEO of the spinout software company, DealerBuilt. DealerBuilt grew slowly as a bootstrapped startup in a market full of large incumbent com…

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