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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

01:08:21

#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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57:28

#164: SaaS Founders Save Millions With Fractional...

Practical Founders Podcast ·

2025/10/03

Praveen Ghanta, founder of Fraction and former CEO of HiddenLevers, shares how he turned his experience scaling a bootstrapped SaaS company into a fast-growing fractional talent marketplace. After HiddenLevers reached $8M in ARR and sold for over $100M, he realized that senior fractional engineers were the secret to delivering efficiently without expensive full-time hires. Fraction now serves over 100 SaaS clients with a vetted pool of 500 senior U.S.-based engineers and CTOs. Typical engagements

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01:12:36

#163: Anthony Pierri & Rob Kaminski of Fletch: Why...

Practical Founders Podcast ·

2025/09/26

Anthony Pierri and Rob Kaminski are the co-founders of Fletch, a positioning strategy firm for B2B SaaS companies. They started Fletch after observing that most founders often confuse positioning with copywriting and marketing, and built their business by helping SaaS leaders make the tough, strategic choices about who they serve and how they win. Over the last three years, Anthony and Rob have collaborated with over 400 SaaS companies, ranging from early-stage startups to rapidly growing companies

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01:00:34

#162: Practical Investor - What’s Working Now in...

Practical Founders Podcast ·

2025/09/19

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 vertical software companies like Toast, ServiceTitan, Jane, and CCC. Tidemark hosts its annual VSaaS Collective Live Event, featuring experienced speakers for hundreds of vertical SaaS founders, on November 5, 2025. In this episode, we discuss the practical

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53:41

#161: When Co-Founders Need Relationship Therapy -...

Practical Founders Podcast ·

2025/09/12

Dr. Matthew Jones is a licensed clinical psychologist who specializes in working with co-founders to help manage critical conflicts that threaten their success. He is the author of the book, "The Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup Success." Matt has worked with hundreds of bootstrapped and VC-funded co-founder teams to help them repair and manage their relationships in the context of their growing business. In this episode, we discuss a wide range of

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01:08:27

#160: CPG Founder Turned Failure Into a Profitable...

Practical Founders Podcast ·

2025/09/05

Yuval Selik is co-founder and CEO of Promomash, a software platform and managed service for Consumer Packaged Goods (CPG) brands to manage their trade promotions and field marketing activities. Yuval is a former CPG founder who encountered the expensive, complex, and crucial process of managing trade promotions with stores and distributors. Promomash launched in 2015 to serve mid-sized CPG companies that don’t have custom software and their own teams to manage promotion spend and budget compliance

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01:04:25

#159: Co-Parenting App Reaches $10M ARR Through Pure...

Practical Founders Podcast ·

2025/08/29

Vince Mayfield is cofounder and CEO of TalkingParents, a co-parenting app for communication and coordination used by divorced parents raising children. Cofounder Stephen Nixon was a lawyer with family cases who saw the need for a secure, unalterable communication record to improve co-parenting and family harmony. He pitched a development company owned by Vince and Louis Anderson to build the first app. They came together to cofound TalkingParents in 2016 . Stephen worked with judges, courts, and

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177 results

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