PODCAST · business
Practical Founders Podcast
by Greg Head
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.
Episodes
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#218: He Built Debt Collection SaaS While Paying Off $1M in Personal Debt - Josh Allen
Josh Allen is founder and CEO of Tratta, software for debt collection agencies and creditor rights law firms that gives consumers self-service payment tools and gives agents modern back-office tools. He started in merchant services, hired contractors to build a payment portal, and found out the...
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#217: His Hardest Lesson: Going Too Fast Was More Risky, Even With Funding - Shawn Boyer
Shawn Boyer is founder and CEO of goHappy, a frontline employee communication and engagement platform for companies with a thousand or more hourly workers in restaurants, logistics, manufacturing, and retail. Before that he started Snagajob in 2000, a job marketplace for hourly workers, funding…
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#216: Messy Financials Killed a Good LOI and Slowed a Profitable SaaS Sale - Riccardo Pisano
Riccardo Pisano grew up in Rome, started coding at fourteen, and came to the US for a master's in e-commerce. After a venture-chasing startup called Proximity stalled, he and co-founder Roy turned an internal LinkedIn outreach script into Growth-X in January 2016. Riccardo refused to write a line...
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#215: How This Early-Stage Growth Equity Partner Is Investing in SaaS in 2026 - Steve Wolfe
Steve Wolfe co-founded Growth Street Partners in San Francisco about ten years ago with his partner Nate Grossman, after a career in software-focused private equity. The firm's name is the point: they don't invest on Sand Hill Road, Wall Street, or even Main Street, but a street or two behind it,...
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#214: He Stopped Being the Face of the Company Before He Sold It - Heath Adams
Heath Adams is a military veteran in Albuquerque who started posting ethical hacking videos on YouTube under the handle The Cyber Mentor. The videos found a large audience, consulting clients started showing up, and he launched TCM Security as a penetration testing shop. Then he put a course on...
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#213: She Took on a Growth Equity Partner for the Advice, Not the Money - Lynn Burghardt
Lynn Burghardt is a fifth-generation owner of Burghardt Sporting Goods — the oldest family-owned sporting goods store in the country, founded in 1881. Chipply grew out of that business: after years of hacking together their own tools for team apparel orders, Lynn and two brothers built the…
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#212: The Practical Case for Payments-Driven SaaS Growth, Not Subscriptions - Jay Majaraj
Jay Maharaj built TeamLinkt in Saskatoon, Saskatchewan, a place not known for software. He saw the problem while coaching his own kids: the hockey team had a budget for a team communication app, and the soccer team didn't, so he either paid for it himself or went without. He launched the…
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#211: This Practical Bootstrapper Scaled Up and Became a Serial Acquirer - Ajay Gupta
Ajay Gupta founded Stirista in San Antonio after helping with micro-targeting a presidential campaign. His first product identified people who spoke a second language for multicultural marketing — built from scanned baby-name books, a hundred thousand first names, and 107 sales calls before Dish...
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#210: 4th Time Founder: Solve Distribution First, Write Code After - Vic Levitin
Vic Levitin is a serial founder who built companies in Israel for two decades before fleeing the war with his young family to the island of Koh Samui, Thailand. His first SaaS company, CrazyLister, grew out of his own e-commerce business where he needed a simple way for eBay sellers to build...
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#209: Leading from Both Sides of the Table as a PE-Backed SaaS CEO - Steve Oriola
Steve Oriola isn't the founder of Unbounce — he's the CEO that Crest Rock Partners brought in to run and transform it. A sales-and-marketing software veteran who spent a decade at Constant Contact, and even ran Act! for a spell (ACT! is the product and company I helped grow and run myself 10…
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#208: How AI Rewrote What Active SaaS Buyers Want in 2026 - Mike Lyon
Mike Lyon is the founder and managing director of Vista Point Advisors, a boutique sell-side investment bank he started almost sixteen years ago. A former chemical engineer at Exxon and BP who later joined Citigroup's tech M&A team, he built Vista Point to solve a conflict of interest he watched...
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#207: Former Teacher Built a Market-Leading School Hiring Marketplace - Wayne Cartmel
Wayne Cartmel grew up on a small farm in the Lake District region of northwest England and was selling chickens by the age of four. He trained as a maths teacher in Bedfordshire and could not believe the process he had to go through to apply for jobs — hours of Word-based application forms, one...
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#206: He Sold at $3M ARR and Got a 10X+ Exit to a PE Buyer - Eran Galperin
Eran Galperin is a Brazilian jiu-jitsu black belt who had already had one VC-backed marketplace failure when he started Gymdesk. Originally called Martial Arts on Rails, it launched in 2016 as a naive version of what he thought a gym needed. He was training five or six times a week and every gym...
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#205: Domain Knowledge Is the New Moat, Not Features and Code - Cliff Sentel
Cliff Sentell co-founded Compass Professional Health Services in Dallas in 2005, where he and two partners each put in $20,000 and bought a single server. They started in healthcare price transparency, reverse-engineering the cost of specific procedures on specific plans out of billions of...
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#204: He Sold a Majority, Gave Up Control, and Became Indispensable - Matthew Bullis
Matthew Bullis grew up in a mud-brick hut with no running water on a small island off South Korea, was adopted to the US at 11 speaking no English. After a dot-com near-miss, he took over his brother's struggling concrete-pumping software — down to about $20,000 a year — for 90% of the company.…
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#203: Every Software Team Should Put AI Agents on the Org Chart - Nick Olsen
Nick Olsen is the Head of AI Innovation at Mainsail Partners, where he works hands-on with 25 scaling vertical SaaS companies helping them adopt AI in engineering and product. Before joining Mainsail, Nick spent 20 years helping build ResMan from a 3-person startup into a scaled software company...
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#202: Practical Fintech: Surviving Payment Platforms and Big Banks - Paul Hoeper
Paul Hoeper founded InvoiceASAP after spotting a simple but painful problem in 2009: home service businesses couldn't easily create invoices or collect payments from the field using mobile devices. He started in New Orleans, launched during the earliest days of mobile apps, and built one of the...
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#201: Creating a New Category in SaaS for Key Account Managers - Jerry Alderman
Jerry Alderman is the co-founder and CEO of Valkre Solutions, a SaaS platform built specifically for key account managers who oversee the largest and most strategic customers in global B2B companies. After careers in engineering, sales, leadership, entrepreneurship, and customer value consulting,...
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#200: The Biggest Pricing Mistakes That Hurt Growing SaaS Companies - TJ Joosten
TJ Joosten is the co-founder of RevFixr, a pricing and monetization consultancy that helps SaaS companies improve pricing, packaging, and revenue growth. Before starting RevFixr, TJ spent a decade building and selling software, helping early-stage companies find customers, refine product-market...
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#199: Enterprise SaaS Built on Salesforce to a Practical Founder Exit - Rupert Mayer
Rupert Mayer is the founder of IPfolio, a vertical SaaS platform built for corporate intellectual property teams to manage patents, trademarks, renewals, and innovation workflows. Originally from Austria, Rupert stumbled into IP software while helping a patent law firm solve Y2K risks, then moved...
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#198: Protecting the Soul of Your Company, with Eric Ries, Author of the Lean Startup
Eric Ries is the entrepreneur and author of The Lean Startup, whose work helped software founders validate ideas faster and build companies without making huge bets upfront. After years helping startups, large companies, and governments apply Lean Startup principles, Eric built the Long-Term…
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#197: Scaled His Niche Vertical SaaS ERP with Growth Equity - Marc Sanderson
Marc Sanderson is the founder and CEO of INNERGY, but he didn't start as a software founder. After earning his MBA and searching for a company to buy, he and partner Walter Wilkie acquired a small architectural woodworking business in Minnesota in 1997. Running that business revealed a deep...
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#196: Founder Conflict, Burnout, and a Successful SaaS Exit - Blakely Graham
Blakely Graham co-founded TaskRay, a project management and customer onboarding platform built inside the Salesforce ecosystem. After years working with Salesforce implementations and operations teams, she and co-founder Eric Wu saw a major gap between closing deals and successfully onboarding...
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#195: Built a Calm, Profitable SaaS—Then Sold It on His Terms - Andy Alsop
Andy Alsop didn't start The Receptionist—he bought a small iPad-based visitor management app in 2013 for $250K and turned it into a real SaaS business. What began as a simple front-desk check-in tool evolved into a full visitor management system used across offices, schools, and manufacturing...
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#194: Why Selling Your Company Can Be a Growth Strategy - Sharon Nouh
Sharon Nouh built ProSpend, a spend management SaaS platform for mid-market companies, after seeing firsthand how broken expense processes were in corporate travel. Starting with an expense tool, focused on her home market in Australia, she bootstrapped the company and landed a global enterprise…
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#193: The Real Bottom of the Funnel: SaaS Onboarding That Works - Perry Rosenbloom
Perry Rosenbloom, founder of LaunchBay, previously built and sold Brighter Vision before starting his second SaaS company focused on onboarding. After running hundreds of onboarding processes per month, he saw a consistent problem: what happens after the sale is messy, manual, and often ignored....
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#192: Built A Vertical SaaS Giant In Aviation Without VC Funding - Dinakara Nagalla
Dina Nagalla built EmpowerMX over more than a decade to digitize aircraft maintenance for major airlines like American, Southwest, and United. Starting from deep domain experience inside aviation IT, he tackled a complex, high-stakes problem—replacing paper-based processes with a full execution...
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#191: No Investors the 2nd Time - Bootstrapped to a Bigger Exit - Chad Ingram
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…
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#190: Building Faster with AI-Powered Product Demos That Convert - Joseph Lee
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...
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#189: How Lighter Capital Finances Bootstrapped SaaS Growth - Tanner Kovacevich
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...
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#188: The Practical Long Game: 25 Years Scaling QuestionPro - Vivek Bhaskaran
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…
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#187: Practical Rule of 40 Growth+Profits Still Works for SaaS Acquirers - Juan Ignacio Garcia Braschi
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...
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#186: The Grind Behind a Stellar SaaS Exit in the UK - Simon Swords
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...
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#185: Survived COVID and a PE Exit —A Travel Tech Founder's Journey - Steve Reynolds
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...
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#184: Fixing The Software Development Mess For Non-Technical Founders - Keith Shields
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...
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#183: Selling to the Gorilla: Snap's Strategic Exit to ICE Mortgage Tech - Will Caldwell
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...
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#182: Why Focus Beats Funding in Crowded SaaS Markets - Luigi Mallardo
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…
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#181: Why Systems (with AI) Scale Better Than People in SaaS - Jordon Comstock
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...
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#180: AI Is Not Killing Vertical SaaS - It's Practical Leverage - Deepak Sindwani
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....
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#179: Don't Sell Your SaaS Yet: Hire a CEO and Get Your Life Back - Tighe Burke
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…
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#178: Approaching $20 Million ARR with 99% Annual Retention - Dan MacDonald
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"...
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#177: Building Multi-product Vertical SaaS With a Tiny Team - Robin Eissler
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...
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#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head
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…
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#175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh
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...
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#174: Plateaus, Pivots, and Staying Profitable: Solving Practical SaaS Puzzles - Josh Ho
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…
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#173: From COVID Boom to Bootstrap Mode: Hubilo's Refounder Story - Shailesh Hegde
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…
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#172: Why Long-Term Bootstrapping Still Works in Event Mgt. SaaS - Raju Patel
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,...
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#171: Lessons from a 9-Year Bootstrap Journey to a Private Equity Exit - Dharshan Rangegowda
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,...
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#170: Why Most SaaS Acquirers Still Want Profitable Growth in 2025 - Gaurav Bhasin
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...
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#169: Practical Pivot and Relaunch Created Profitable 200% Growth - Natalie Barbu
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…
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ABOUT THIS SHOW
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.
HOSTED BY
Greg Head
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How many episodes does Practical Founders Podcast have?
Practical Founders Podcast currently has 216 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Practical Founders Podcast about?
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.
How often does Practical Founders Podcast release new episodes?
Practical Founders Podcast publishes regularly with 216 episodes available. Check the episode list for the typical release schedule.
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Who hosts Practical Founders Podcast?
Practical Founders Podcast is created and hosted by Greg Head.
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