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
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Podcast website
Latest episode
Jul 10, 2026
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Episodes
#179: Don't Sell Your SaaS Yet: Hire a CEO and Get Your Life Back - Tighe Burke 16.01.2026 1:00:27
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...
#178: Approaching $20 Million ARR with 99% Annual Retention - Dan MacDonald 09.01.2026 1:08:21
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-ris...
#177: Building Multi-product Vertical SaaS With a Tiny Team - Robin Eissler 02.01.2026 1:10:50
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...
#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head 26.12.2025 54:01
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 ep...
#175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh 19.12.2025 1:06:44
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...
#174: Plateaus, Pivots, and Staying Profitable: Solving Practical SaaS Puzzles - Josh Ho 12.12.2025 1:06:51
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...
#173: From COVID Boom to Bootstrap Mode: Hubilo's Refounder Story - Shailesh Hegde 05.12.2025 1:08:37
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. ...
#172: Why Long-Term Bootstrapping Still Works in Event Mgt. SaaS - Raju Patel 28.11.2025 59:31
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...
#171: Lessons from a 9-Year Bootstrap Journey to a Private Equity Exit - Dharshan Rangegowda 21.11.2025 1:03:56
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,...
#170: Why Most SaaS Acquirers Still Want Profitable Growth in 2025 - Gaurav Bhasin 14.11.2025 1:05:00
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 typi...
#169: Practical Pivot and Relaunch Created Profitable 200% Growth - Natalie Barbu 07.11.2025 1:04:42
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...
#168: These Three Superpowers Set Practical SaaS Founders Apart - Greg Head 31.10.2025 52:30
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-...
#167: Practical Founders Brought in CEO to Scale Their Company - Darryl Pahl 24.10.2025 1:10:55
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 Ondrejcek, 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...
#166: How Practical SaaS Founders Can Compete in the AI Economy - Vincent Serpico 17.10.2025 58:39
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...
#165: How to Enjoy Being the CEO as Your SaaS Business Grows Bigger - Brett Gilliland 10.10.2025 1:01:34
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 sep...
#164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta 03.10.2025 57:28
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 ov...
#163: Anthony Pierri & Rob Kaminski of Fletch: Why All SaaS Founders Struggle with Positioning 26.09.2025 1:12:36
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 c...
#162: Practical Investor - What's Working Now in AI-Driven SaaS Growth - Dave Yuan 19.09.2025 1:00:34
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 spea...
#161: When Co-Founders Need Relationship Therapy - Dr. Matthew Jones 12.09.2025 53:41
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 th...
#160: CPG Founder Turned Failure Into a Profitable SaaS Business - Yuval Selik 05.09.2025 1:08:27
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 compa...
#159: Co-Parenting App Reaches $10M ARR Through Pure Bootstrap Growth - Vince Mayfield 29.08.2025 1:04:25
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 recognized 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 Erickson to build...
#158: $33M Growth Equity After Friends/Family Funding to $10M ARR - Alan Miegel 22.08.2025 1:11:51
Alan Miegel is co-founder and CEO of BetterComp , a modern compensation management platform for larger companies to manage compensation datasets to set market-priced salary benchmarks. Alan and his cofounders started the company in 2019 with founder funding, then raised angel funding as convertible debt from his friends in the tech industry. They shipped their first "minimum sellable product" in 2...
#157: Seven Years In Survival Mode: A VC-funded Founder's Warning - Zvi Band 15.08.2025 1:07:12
Zvi Band is co-founder and former CEO of Contactually, which was CRM software for real estate and other relationship-oriented professionals. Contactually was founded in 2011 with initial funding and support from 500 Startups in Silicon Valley. In the next five years, they raised a total of $15.5 million from institutional VC investors. Contactually grew to about $10 million in revenue before growt...
#156: Bootstrapper Built Vertical CRM to $10M ARR with Co-founder Dad - Shoanak (Sean) Mallapurkar 08.08.2025 1:11:26
Shoanak (Sean) Mallapurkar is the founder and CEO of Recruit CRM , a complete CRM and business management system for global staffing companies and recruiting agencies. He started the company in 2017 with his father, a technical expert who had experience as a senior executive in large staffing companies. Sean handled customer-facing jobs in sales, success, and product management, and his Dad manage...
#155: SaaS Founder's Crazy Ride: Boom, Bust, Strategic Sale - Jesse Burrell 01.08.2025 1:08:33
Jesse Burrell is the CEO and co-founder of BatchService, now known as BatchData , a real-time data and API platform designed for prop-tech startups and enterprises requiring massive and current housing data. Jesse was a real estate investor who needed better data to target his marketing efforts. BatchService was launched in 2018 with data brokering and subsequently built additional tools and apps....
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