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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

01:11:41

#191: No Investors the 2nd Time - Bootstrapped to a...

Practical Founders Podcast ·

2026/04/10

Chad Ingram is the founder of Distro, an AI recruiting software company that helps mid-market and enterprise companies automate candidate screening, vetting, ranking, and scheduling. He previously built Jump, a venture-backed customer engagement software company, through a stressful growth and sale process that taught him painful lessons about fundraising, control, and acquisition pressure. Distro started as a marketplace to help companies hire software engineers globally, then evolved into an

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01:01:47

#190: Building Faster with AI-Powered Product Demos...

Practical Founders Podcast ·

2026/04/03

Joseph Lee is the co-founder and CEO of Supademo, a fast-growing SaaS company solving a common pain: quickly creating new product demos. In just two and a half years, they built a modern, AI-powered solution that dramatically simplifies how teams showcase software. Supademo has reached $3M ARR in 2.5 years and is growing more than 100% annually with a freemium model. The product enables teams to create interactive, annotated, and even translated demos in minutes instead of days or weeks. The

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58:11

#189: How Lighter Capital Finances Bootstrapped SaaS...

Practical Founders Podcast ·

2026/03/27

Tanner Kovacevich of Lighter Capital joins Greg Head to explain how non-dilutive financing works for practical SaaS founders. Since 2010, Lighter Capital has funded hundreds of recurring-revenue SaaS companies that want growth capital without giving up ownership or board control. Tanner shares discuss how non-dilutive financing fits companies with $1M–$5M ARR that are growing steadily but don't want venture capital. He explains typical loan structures, underwriting factors like churn and revenue

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01:10:12

#188: The Practical Long Game: 25 Years Scaling...

Practical Founders Podcast ·

2026/03/20

Vivek Bhaskaran is the founder and CEO of QuestionPro, a bootstrapped survey and customer-experience research software platform they have been building for more than 25 years. Based in the Bay Area, Vivek has grown the company globally without venture capital, staying deeply involved in product and running the business as both CEO and de-facto chief product officer. As QuestionPro crossed $10M then $30M in revenue years ago, private equity firms and acquirers started calling. Vivek chose not to sell

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56:41

#187: Practical Rule of 40 Growth+Profits Still Works...

Practical Founders Podcast ·

2026/03/13

Juan Ignacio Garcia Braschi is a partner at L40, a boutique SaaS M&A advisory firm with offices in Madrid, Lisbon, and Miami. After two decades in banking, private equity, and operating roles, including serving as CFO of ride-hailing company Cabify, he now helps SaaS founders sell companies typically valued between $20M and $200M. L40 works primarily with B2B SaaS companies doing $5M–$50M ARR, most of them bootstrapped or lightly funded, including companies in Europe and Latin America. Juan explains

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01:12:41

#186: The Grind Behind a Stellar SaaS Exit in the UK...

Practical Founders Podcast ·

2026/03/06

Simon Swords founded Fundipedia after starting in a backyard shed building bespoke software. Originally a custom development shop, his firm built a data governance platform for major buy-side asset managers including HSBC, Barclays, and Legal & General. Over time, Fundipedia evolved into a high-retention enterprise SaaS platform with strong net revenue retention and Rule of 40 performance. Simon navigated long consultative sales cycles, regulatory tailwinds, and a tightly networked financial

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01:00:16

#185: Survived COVID and a PE Exit —A Travel Tech...

Practical Founders Podcast ·

2026/02/27

Steve Reynolds didn't start TripBam to disrupt the global hotel industry—he simply noticed that corporations weren't getting the discounts they negotiated, and no one was checking. After 30 years in travel technology, he saw a broken system hiding in plain sight. What began in 2013 as a consumer hotel re-shopping tool quickly revealed a much bigger enterprise opportunity. When a corporate client offered to pay a subscription fee, Steve pivoted from B2C to B2B—and never looked back. TripBam went on

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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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190 results

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