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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

01:03:53

#184: Fixing The Software Development Mess For...

Practical Founders Podcast ·

2026/02/20

Keith Shields is co-founder and CEO of Designli, a custom software development company that's helped non-technical founders build over 200 digital products in 13 years. After struggling to build apps through unreliable agencies in his own early startup, Keith focused on fixing the many painful experiences most founders have when hiring software development teams. Designli operates as a complete outsourced engineering department for practical software founders building SaaS and AI products, mobile

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52:22

#183: Selling to the Gorilla: Snap's Strategic Exit...

Practical Founders Podcast ·

2026/02/13

Will Caldwell started Snap after his first real estate software startup fizzled, pivoting from agent tools to regulated compliance data. He discovered lenders were required to buy hazard and flood certifications, and realized this was a "painkiller" product. He built Snap as a data and analytics platform for real estate and mortgage underwriting. Snap grew from a single California compliance product into a national flood data business, reaching $5M in revenue and 30 employees. The company charged

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01:02:54

#182: Why Focus Beats Funding in Crowded SaaS Markets...

Practical Founders Podcast ·

2026/02/06

Luigi Mallardo joined Woffu as an early angel investor and later became CRO, helping founder Miguel Fresneda shape a practical SaaS growth path. Based in Barcelona, Spain, Woffu has built a modern cloud-based time and attendance platform for SMEs and mid-market companies, replacing legacy tools and spreadsheets with a focused, mobile-first workforce solution. Starting from just €2K MRR, Luigi led growth first through inbound, then outbound, and partner channels, increasing average revenue per

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59:25

#181: Why Systems (with AI) Scale Better Than People...

Practical Founders Podcast ·

2026/01/30

Jordon Comstock is founder and CEO of BoomCloud, a vertical SaaS company serving dental practices with patient membership software. He started the company scrappy and bootstrapped, with no outside funding, after years in the dental industry managing his family's dental lab business. BoomCloud now does about $3M in ARR with roughly 600 dental practices and an 11-person team. The company helps dentists replace insurance-driven revenue with subscription-based patient memberships, creating higher

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49:23

#180: AI Is Not Killing Vertical SaaS - It's...

Practical Founders Podcast ·

2026/01/23

Deepak Sindwani is Managing Partner at Wavecrest Growth Partners, an active growth equity firm backing bootstrapped and lightly funded SaaS founders. They work with practical founders who've built profitable businesses to $5–$20M ARR and want help growing without VC pressure or losing control. Wavecrest invests in vertical SaaS companies growing 30–60% annually, typically profitable or breakeven. They help founders scale sales, pricing, analytics, and leadership teams while staying capital

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01:00:27

#179: Don't Sell Your SaaS Yet: Hire a CEO and Get...

Practical Founders Podcast ·

2026/01/16

Tighe Burke is the founder of SRCH Partners, a boutique executive search firm that helps SaaS founders replace themselves as CEO without selling their companies. After years in large executive recruiting firms, Tighe built a practice focused on founders who want their business to keep growing while they step back from day-to-day leadership. Tighe works with profitable software companies typically in the $5M–$50M revenue range, helping founders hire experienced and scrappy operators who have already

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01:08:21

#178: Approaching $20 Million ARR with 99% Annual...

Practical Founders Podcast ·

2026/01/09

Dan MacDonald is the founder and CEO of BIS Safety Software, based in Edmonton, Canada. He didn't start in safety or software—he came from retail and leadership training before an unexpected pivot led him into online safety systems. That shift eventually became a long-term bet on a "un-sexy" problem that companies can't ignore. Today, BIS Safety serves more than 2.5 million users across high-risk industries like construction, mining, transportation, and energy. The company generates roughly $25M

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01:10:50

#177: Building Multi-product Vertical SaaS With a...

Practical Founders Podcast ·

2026/01/02

Robin Eissler is the founder and CEO of BoosterHub, a vertical SaaS platform built for high school booster clubs. After selling her prior business as a private jet broker, Robin volunteered to run a local booster club and discovered a messy problem run with spreadsheets, emails, and manual accounting. She decided to build a single system that could actually handle it. BoosterHub now serves nearly 600 booster programs, representing over 100,000 users. With just two full-time employees and a small dev

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54:01

#176: The Five Questions That Will Decide Your SaaS...

Practical Founders Podcast ·

2025/12/26

As the year winds down, I want to share an end-of-year message for practical SaaS founders who want to make better progress in 2026. Based on my recent conversations with more than 40 CEOs in my Practical Founders peer groups, it's clear that growth rates alone don't define whether it was a "good" year. Founders experienced very different outcomes—and very different feelings about them. In this episode, I walk through five practical questions I believe founders should ask as they look ahead to 2026

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01:06:44

#175: The Hidden Founder Psychology Patterns Behind...

Practical Founders Podcast ·

2025/12/19

Dave Hersh, co-founder and former CEO of Jive Software, shares the real story behind bootstrapping Jive to $12M in revenue before raising venture capital and scaling aggressively. He explains how fear, comparison, and the pressure to "go big" drove him to abandon his profitable core business and pursue a new upmarket strategy that ultimately cost the company its soul. After growing to $60 million, Jive eventually went public, but not without internal strain, personal turmoil, and ultimately the

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01:06:51

#174: Plateaus, Pivots, and Staying Profitable:...

Practical Founders Podcast ·

2025/12/12

Josh Ho is the Founder and CEO of Referral Rock, a bootstrapped referral marketing platform serving SMBs that rely on multi-step, relationship-driven sales. Starting in 2015 as a solo developer consulting on the side, Josh built the first version himself, validated demand quickly, and landed early customers by doing demos and hands-on support. Referral Rock has grown to roughly 500 customers, 20 team members, and about $3M in annual revenue. The company scaled through strong inbound SEO,

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01:08:37

#173: From COVID Boom to Bootstrap Mode: Hubilo's...

Practical Founders Podcast ·

2025/12/05

Shailesh Hegde is the CEO of Hubilo, a Bangalore-based webinar software company that initially started during COVID as virtual events tech and raised $150M in VC funding before the market shifted. Originally joining as head of product, he stepped into the CEO role during a chaotic downturn and led the company through a full strategic reset after returning all the remaining capital to investors. When the virtual events boom collapsed, Shailesh and the team rebuilt Hubilo into a mid-market webinar

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59:31

#172: Why Long-Term Bootstrapping Still Works in...

Practical Founders Podcast ·

2025/11/28

Raju Patel founded eShow over 25 years ago after building a speaker portal for a magazine company and realizing he had a repeatable software product. What began as a one-man shop in suburban Chicago evolved into a robust event-management platform serving associations that needed complex, multi-module functionality. His business grew steadily as he delivered registration, booth management, speaker portals, and onsite systems for demanding event teams. Today eShow has 125 employees, more than 14

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01:03:56

#171: Lessons from a 9-Year Bootstrap Journey to a...

Practical Founders Podcast ·

2025/11/21

Dharshan Rangegowda, founder of ScaleGrid, left a decade-long engineering career at Microsoft to solve a painful database operations problem he had lived firsthand. After early missteps selling to enterprises, he shifted to helping developers manage MongoDB, Redis, and Postgres on the cloud, bootstrapping the business from scratch. ScaleGrid grew steadily through product depth, technical support, and Dharshan's mastery of SEO—becoming the top organic result for many key searches. The company

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01:05:00

#170: Why Most SaaS Acquirers Still Want Profitable...

Practical Founders Podcast ·

2025/11/14

Gaurav Bhasin is the founder and managing director of Allied Advisers, an M&A advisory firm whose principals have completed over 100 sell-side transactions for software and tech founders. After two decades in investment banking and tech M&A, Gaurav is a sell-side advisor to B2B software founders who have built successful businesses and want to explore selling their companies. Allied Advisers typically works with founders selling their businesses for $20M–$200M, helping them prepare materials, run a

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01:04:42

#169: Practical Pivot and Relaunch Created Profitable...

Practical Founders Podcast ·

2025/11/07

Natalie Barbu is the founder and CEO of Rella, a SaaS platform built to streamline collaboration and workflows for social media teams and agencies. She began as a YouTube creator, grew a following of over 300,000, and then identified the fragmentation of the creator tools market — which led her to build Rella 1.0. With some small seed funding, the first Rella version focused on content creators and made no revenue with a freemium model. With $25K in the bank and no revenue, the four cofounders

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52:30

#168: These Three Superpowers Set Practical SaaS...

Practical Founders Podcast ·

2025/10/31

In this episode, the founder of Practical Founders, Greg Head, shares the most powerful insights from over 165 podcast interviews and working with 40+ bootstrapped SaaS founders in his peer groups. Greg breaks down the common but less obvious traits he sees in practical founders who are quietly building valuable software companies without big VC funding. Greg shares how frugality and managed risk-taking coexist to create compounding steady growth, creating massive long-term value fpr practical

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01:10:55

#167: Practical Founders Brought in CEO to Scale...

Practical Founders Podcast ·

2025/10/24

Darryl Pahl is the co-founder of DFnet, a Seattle-based company providing clinical trial data management software and services. Along with his wife and co-founder, Lisa Andrzejczyk, Darryl started the company more than 20 years ago after careers at Fred Hutchinson Cancer Research Center. They built DFnet around long-term client relationships in global health and clinical research. The company runs DFdiscover, an enterprise-grade electronic data capture and management platform used in clinical

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58:39

#166: How Practical SaaS Founders Can Compete in the...

Practical Founders Podcast ·

2025/10/17

Vincent Serpico, veteran CTO and founder of Founders Workshop, is on the front lines of the AI revolution in 2025, reshaping software development and business operations. With more than 30 years of experience building software apps, Vincent is now dedicating himself full-time to AI coaching and workshops for teams and companies to create high-leverage impact quickly. Vincent shares how practical SaaS founders are leveraging agents, vibe coding, and tools like OpenAI’s Agent Kit to multiply output

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01:01:34

#165: How to Enjoy Being the CEO as Your SaaS...

Practical Founders Podcast ·

2025/10/10

Brett Gilliland, founder of Elite Entrepreneurs, joins Greg to discuss how they help ambitious founders navigate the tough leadership journey from $1M to $10M in revenue. Brett shares how co-creating a clear, practical Purpose, Values, and Mission form the foundation of scalable organizations. He explains why moving from founder-led chaos to aligned leadership teams is the critical step that separates $1M experiments from $10M companies. With clear meeting rhythms, disciplined execution, and strong

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183 results

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