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PODCAST

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.

business entrepreneurship

All Episodes

01:00:15

#138: Achieved Strategic Acquisition Just 2 Years...

Practical Founders Podcast ·

2025/04/04

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 Skematic with a coworker and launching in September 2022. Skematic grew quickly by solving an acute problem for lawyers and compliance execs just like him in his

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01:04:57

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

Practical Founders Podcast ·

2025/03/28

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 $30M in annual recurring revenues with 75 employees and over 100,000 paid customers. They have been profitable since the second week after launch, driven

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01:11:26

#136: Practical Founder Has Big Exit and Un-Retires...

Practical Founders Podcast ·

2025/03/21

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, Brian “retired” to spend more time with his growing family. He enjoyed his free time but eventually returned to the software startup game with his second

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55:49

#135: Vertical SaaS Investor Shares Proven Paths to...

Practical Founders Podcast ·

2025/03/14

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 useful strategic growth frameworks for vertical SaaS companies to grow through winning market share, expanding with additional products, and even

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44:27

#134: When It’s Time to Close: Helping Founders Shut...

Practical Founders Podcast ·

2025/03/07

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. SimpleClosure has helped tech startup founders wind down over 500 startups, businesses that closed or have gone through a sale of assets. It manages the important

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58:47

#133: Bootstrapper Sells School Fundraising Platform...

Practical Founders Podcast ·

2025/02/28

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 students raise over $30 million in donations. Their platform has tracked over 30 billion reading minutes by students who have used it to earn donations.

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01:09:35

#132: Bootstrapper Serving Private Equity Firms...

Practical Founders Podcast ·

2025/02/21

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 complex problem that was being managed on spreadsheets. He left to start PFA Solutions and bootstrapped the development of FirmView with consulting revenue

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01:03:43

#13`: No-Code SaaS Platform Bootstrapped to 75,000...

Practical Founders Podcast ·

2025/02/14

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 venture firm in Michigan, doing repetitive manual data imports and analysis in Excel. He hired a developer to build a better tool and started to sell

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01:07:58

#130: Profitable Product-Led Growth to $30 Million...

Practical Founders Podcast ·

2025/02/07

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 four Danish founders before the company was moved to Silicon Valley in 2013 when Joe was hired as the CEO. Joe ran the company for almost 12 years, growing

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01:06:34

#129: On Freedom and Ownership With Software...

Practical Founders Podcast ·

2025/01/31

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), America’s first fintech company, Hamilton developed technology that translates complex financial data, empowering millions of small business owners. Sageworks

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01:04:33

#128: Solving a Challenging SaaS Growth Puzzle -...

Practical Founders Podcast ·

2025/01/24

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 2016 to serve smaller companies that spend millions on digital ads and other marketing, including email, SEO, and digital events. Determining which

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01:11:52

#127: Scaling SaaS with Efficient Growth and...

Practical Founders Podcast ·

2025/01/17

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. Bryan raised some practical funds from angels to start the company in 2016. The company grew 50% or more every year since then. In 2021, Boostlingo raised a

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57:57

#126: Jason Fried on 20 Years Bootstrapping BaseCamp...

Practical Founders Podcast ·

2025/01/10

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 funding and build sustainable businesses that are great for customers and generate healthy profits for the owners. His best-selling book, Rework, shared

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01:08:10

#125: Created the World’s Largest Subscription...

Practical Founders Podcast ·

2025/01/03

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 just picked a vertical niche, like we are the graphic design provider for feline mobile cutting trucks or something. There are easily 10,000 mobile pet

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01:05:41

#124: From Services to SaaS Products to a Successful...

Practical Founders Podcast ·

2024/12/27

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 the product. Apiculus is a complete "cloud-as-a-service" software platform for data centers to offer, sell, deploy, and manage cloud data services for

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57:37

#123: How Practical Founders Are Winning Big with...

Practical Founders Podcast ·

2024/12/20

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 expert episode, Steve and Nate get specific and share real examples of how SaaS founders use growth equity to win bigger, when it can be a good fit for

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01:02:14

#122: Going Long With Profitable Embedded Accounting...

Practical Founders Podcast ·

2024/12/13

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 acquired the company in 2010. After he left Yardi two years later, Raj and his brother launched Hurdlr to reach the wider small business market with a

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01:05:36

#121: Avoided a VC Round Using Royalty-Based Funding...

Practical Founders Podcast ·

2024/12/06

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 2019. Their royalty-based funding round allowed Geoforce to skip a VC funding round, preserving founder equity and fueling their growth. After their

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01:03:51

#120: Practical Founder Exits for $300 Million Cash...

Practical Founders Podcast ·

2024/11/29

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 know-your-customer (KYC) with a new approach, and sales grew steadily every month. Global Data Consortium (GDC) partnered with data providers and fintech

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01:03:48

#119: Growing His Third Side Gig SaaS Venture After...

Practical Founders Podcast ·

2024/11/22

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 side-gig startup, Dimmo, in 2023 to allow enterprise software buyers to watch product demos without talking to sales reps. With the help of co-founders,

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177 results

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