Greg Head
Practical Founders Podcast
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.
Author
Greg Head
Category
Podcast website
Latest episode
Jul 10, 2026
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Episodes
#78: Fast-Growing K-12 Education Software Company Will Be Profitable This Year – Justin Hewett 19.01.2024 1:06:58
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 the senior executive. When the company was acquired by PE investors, Justin moved on in 2020 and thought about ideas for a new software business to serve K-12 schools in the US. Flashlight Learning helps K-12 teachers i...
#77: Bootstrapped and Winning in Season Ticket Management Software – Morgan Katz 12.01.2024 58:20
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 and front-line venue management. Morgan saw how companies with season tickets had difficulty managing their digital tickets after COVID, so she started her own company to solve it with a software solution. Ticketnology...
#76: Real Estate Investor Built Her Own CRM Solution and Created a Market Leader – Stephanie Betters 29.12.2023 59:55
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 point. Salesforce and a development partner proposed a project so expensive that Stephanie hung up and decided to build the solution herself. She learned to code and build a useful real estate CRM on Sale...
#75: Bootstrapped Their Digital Health Platform to Global Scale with 200 Employees – Shameem Hameed 22.12.2023 1:01:26
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 grew into a comprehensive and customizable platform used by hundreds of healthcare organizations around the world. ZH Healthcare now has almost 200 employees in the US and India...
#74: Practical Holding Company Acquires Profitable SaaS Companies – Kevin McArdle 15.12.2023 1:00:55
Kevin McArdle spent 15 years working in large software companies before becoming a practical investor and acquirer of smaller SaaS businesses. Kevin is the CEO and co-founder of Big Band Software , a holding company that buys and holds small, profitable, and growing SaaS businesses—with no intent of selling those businesses. Kevin has acquired over 40 businesses in the last 10 years with this buy-...
#73: Bootstrapped to successful $67 million exit with medical billing solutions – Harry Hopkins 08.12.2023 1:02:47
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 the product and revenues going before hiring additional staff. Their revenue cycle management (RCM) analytics software reveals medical billing problems and missed revenue opportunities at physician offices in the...
#72: Serial entrepreneur funded his biggest idea yet from other businesses – Hamed Mazrouei 01.12.2023 1:06:59
Hamed Mazrouie 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 multi-site internet phone system to thousands of restaurants and law firms across the US. Vivant grew steadily and profitably for 10 years and is now a maturing business with 50 employees. In the...
#71: Bootstrapped the core software that runs complex manufacturing plants – Subramanyam Kasibhat 24.11.2023 1:05:08
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 a German company. Seven years after they started with their first customer, they rewrote the software to serve other customers and the Vegam Solutions business started to grow. Vegam Solutions is smart factory sof...
#70: Bootstrapped to $3M and Raised a VC Round Before a $200M PE Transaction – Jafar Owainati 17.11.2023 1:09:38
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 software to help sales engineers respond to Requests for Proposals (RFPs) faster and easier. They launched Loopio in 2014 and had paying customers within one year. The three founders built the software and sold the...
#69: Bootstrapped a Fintech Payments Platform to $10M ARR in 3 Years – Miles Schwartz 10.11.2023 1:11:20
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 grown from a focused startup to a credible open banking and instant payment gateway with $10M in ARR. Zum Rails also integrated KYC (Know Your Customer) technology which reduces fraud across all payment types. Miles a...
#68: Bootstrapped and Sold a Successful Startup in Latin America – Bernardo Carvalho Wertheim 03.11.2023 1:11:26
Bernardo Carvalho Wertheim is a worldly entrepreneur who grew up in Sao Paolo, Brazil, and then moved to the UK to go to school and start his career in advertising. He kept traveling and eventually settled in Santiago, Chile, where he started a tech startup and participated in a tech accelerator. The Bridge started as a community and jobs platform connecting UX designers in Latin America to work...
#67: Grew and Sold a Profitable Healthcare Software Company – Patrick Randolph 27.10.2023 1:01:55
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 fill those open slots with patients in the waitlist "queue." With just a little funding and lots of hard work, they began by helping small practices and group practices fill open slots with no human intervention....
#66: Serial SaaS Founder Had Three Successful Exits in Three Different Ways – Raj Khera 20.10.2023 1:06:49
Raj Khera has had three exits as a software entrepreneur and leader in his long career. His first company, GovCon, grew in the late 1990s to help government contractors easily access new contracts up for bid by the US government. Their advertising and subscription revenues grew quickly, and he sold GovCon in 1999 for $12.5 million. He bootstrapped one of the first email marketing software busines...
#65: The Bootstrapped Rocket-Ride Success Story of HighLevel – Robin Alex 13.10.2023 1:11:51
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 and two developers prototyped a marketing automation and CRM software that could help other agencies solve this problem for their clients. They pitched the product and got a great response. They built their first produ...
#64: Bootstrapped, very profitable and still having fun after 18 years – Mike Roberts 06.10.2023 59:02
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. SpyFu was launched in 2006 and has been a profitable and bootstrapped business for almost 18 years. Mike is a happy founder who splits his time between leading the business and his personal pursuits, which inclu...
#63: Successfully Scaling Up a Bootstrapped Vertical SaaS Business – Raution Jaiswal 29.09.2023 55:13
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 the problem, built an early solution, and didn't quit his full-time job in 2018 until he had 50 paying customers. InsuredMine provides an all-in-one sales CRM (customer relationship management) and marketing automati...
#62: She Quit Her CPA Job to Create This Fast-Growing SaaS Startup – Kelly Mann 22.09.2023 55:44
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 automate this process, validated the market with other CPAs, and created the first AuditMiner software. Unfortunately, Kelly was diagnosed with Stage 3 breast cancer just before launch and started aggressive chemotherapy immediately. After...
#61: Sold His Bootstrapped SaaS Company for 16X Revenues - Praveen Ghanta 15.09.2023 1:11:27
Praveen Ghanta graduated from MIT with computer science and economics degrees and worked for various financial services companies after trying his hand at a software startup. Working in his spare time, he built a product and recruited a cofounder to help sell it. After trying to sell it to different types of financial services companies, they finally found a valuable use case with individual wealt...
#60: Created a Practical Venture Studio After Selling His SaaS Company – Oliver Low 08.09.2023 1:08:47
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 invested in building software apps to solve problems that they faced helping big brands promote on the web. One of those products, Platform360, turned into a real SaaS product business which became their focus in 2013. P...
#59: Using Royalty-Based Financing for Non-Dilutive SaaS Funding – Vik Thapar 01.09.2023 53:01
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 and the Cypress team have funded over 50 SaaS and tech-enabled services businesses that have steady recurring revenues and predictable customer acquisition approaches. Revenue-based financing is a form of non-d...
#58: Bootstrapped a successful lawncare services marketplace – Bryan Clayton 25.08.2023 1:02:42
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 help 300,000 homeowners connect with 35,000 landscape service providers. Greenpal is an "overnight success that took 10 years" while the founding team learned to build a software product and recruit homeowners and servi...
#57: Finance, Accounting, and SaaS Metrics Basics for Practical Founders - Ben Murray 11.08.2023 51:14
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 popular blog and podcast with free educational resources to learn advanced SaaS metrics, learn finance best practices, and hear stories from other founders. In this expert interview, I ask Ben all the questions that...
#56: Technical founder shares deep learnings from his many startups – Wissam Tabbara 04.08.2023 1:03:23
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 startup technology teams and now is an experienced CEO and business builder. In 2021 he founded Truebase, a B2B prospecting platform for revenue teams using the power of generative AI accelerates the prospecting...
#55: Bootstrapped to $10M ARR with community-led growth and services – Lloyed Lobo 29.07.2023 1:09:49
Lloyed Lobo is the co-founder and former president of Boast.ai , a leading platform to help software companies in the US and Canada to redeem available government tax credits. Initially started in 2012 as a services business helping companies administer tax credits, Boast.ai was launched as a technology-powered platform that scaled their business much faster. Technology-powered Boast.ai was laun...
#54: Wound down a bootstrapped $1M SaaS startup when the market changed – Ryan Goodman 22.07.2023 1:05:52
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 was acquired by the successful BI company Business Objects, which was then acquired by the huge software company SAP. Ryan left to start consulting and build niche add-on "feature products" in the SAP Business Ob...
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