Practical Founders Podcast
Every week, Greg interviews a successful software founder who started, grew, and often sold a valuable software company without big VC funding.
155
Founders
interviewed
$12.5 B
Total founder
equity value
$79M
Average founder
equity value
0
VC-funded
founders
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 ...
Jerry Alderman is the co-founder and CEO of Valkre Solutions, a SaaS platform built specifically for key account managers (KAMs) who oversee the largest and most strategic customers in global B2B companies. After careers in ...
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, ...
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, ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Dinakara 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 ...
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 ...
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 ...
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 ...
Vivek Bhaskaran is the founder and CEO of QuestionPro, a bootstrapped survey and customer-experience research software platform that they have been building for more than 25 years. Based in the Bay Area, Vivek has grown ...
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 ...
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 ...
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, ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
In this week’s Practical Founders Podcast episode, I share the hidden patterns from over 140 podcast interviews with successful founders, as well as my experience working with more than 40 bootstrapped SaaS founders every ...
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 ...
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 ...
Brett Gilliland, founder of Elite Entrepreneurs, which delivers coaching, workshops, and founder community programs to help hundreds of ambitious entrepreneurs navigate the company leadership journey from $1M to $10M in ...
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 ...
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, ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Brian Forbis is the CEO and President of Blood Bank Computer Systems, Inc. (BBCS), a business his mother created in the 1980s to serve the non-profit blood bank industry in the U.S. Brian started in sales, then transitioned to run ...
Chris Brisson is the CEO and co-founder of Salesmsg, a conversational two-way texting platform that enables businesses to engage with their customers through opt-in SMS. When his first software company stalled, he shut it down and ...
Tracy Larson is President and CEO of WeSuite, a vertical sales automation platform designed for larger integrators who sell complete security systems for commercial and residential real estate. Tracy and the cofounders were in the ...
Henry Valentino is the founder and CEO of EConnect, a leading provider of facial recognition software for casinos and stadiums, ensuring venue security and compliance. He founded EConnect in 2009 and pivoted several times before ...
Josh Turley is the CEO of RTA Fleet Management, a fleet management software company that his grandfather founded in the 1980s and operated as a small family business for decades. Then Josh’s father ran the business until 2015, never ...
Sameer Narkar is the founder and CEO of Konnect Insights, a global SaaS company based in Mumbai that provides an omnichannel customer experience platform to consumer brands in 100 countries. Sameer created Konnect Insights in ...
Chris Erler was co-founder and COO of ComX, a sales pipeline generation for mid-market B2B companies in Germany and Europe. Chris and two other founders started the company in 2018 to conduct turnkey modern digital marketing and ...
Aaron Steffey is the co-founder and co-CEO of Propeller, an online platform that enables insurance agents and brokers to issue surety bonds instantly — without the lengthy paperwork or back-and-forth typically involved in ...
Roy van den Broek is the founder and CEO of Rentman, a rental business management software platform for event and media production companies. Roy built software for his event equipment rental business in the Netherlands. He ...
Gopal Krishnamurthy is the founder and CEO of Lumel, which has a suite of products focused on enterprise performance management (EPM). Their apps allow users to plan, report, and analyze data using modern native app frameworks ...
Phil Stern is the operating principal of Mainsail Partners, a growth equity firm that invests in bootstrapped vertical SaaS companies. Mainsail offers deep operating support to the leaders in their portfolio companies to help ...
Sean Hoban was co-founder and former CEO of Kimble Applications, a leading professional services automation (PSA) software for organizations to manage their professional services business's entire operational and financial ...
Josh LaSov is the founder and former CEO of Satori Reporting, an advanced reporting and business intelligence (BI) solution for mid-market businesses that use NetSuite financial software. Satori provided pre-built reports and ...
Andrew Gazdecki is the founder and CEO of Acquire.com, a marketplace of buyers and sellers of smaller, profitable SaaS products with revenues between $100,000 and $5,000,000. Andrew sold his own software company and learned how ...
Seth Hassell and Clint Ethington are the co-founders of Genius Monkey, a programmatic ad tech platform with proven targeting, tracking, and attribution for optimized results. Seth and Clint were childhood friends who worked on many ...
Shalin Jain is the founder and CEO of HappyFox, a successful bootstrapped company that provides modern help desk management software for customer service, support, and IT management organizations. Shalin and his small team in India built many ...
Brian Kesselman is cofounder and now CRO of Skematic, a compliance management and workflow software for financial services firms. Brian was a lawyer for major financial services companies who helped manage internal compliance ...
Rebecca Shostak is co-founder and chief brand officer of Flodesk, the popular email marketing software for small businesses that care about beautiful branded emails. After prototyping the product and validating the problem, they ...
Brian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard ...
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 ...
Dori Yona is co-founder and CEO of SimpleClosure, a technology- and people-powered company that helps founders wind down and dissolve a startup or business that is no longer viable. Shutting down a business can be complicated, costly, and risky ...
Howard Gottlieb started Read-A-Thon in 2012 as a reading-based fundraising platform that helped students raise money while boosting education. Their easy platform and simple fundraising approach created amazing results. The Read-a-Thon business ...
Richard Change is co-founder and CEO of PFA Solutions, the provider of FirmView software. FirmView® is the leading carry and compensation management platform for private equity investors to manage their internal compensation from fees and ...
Rachit Khator is the founder and CEO of Stackby, a no-code spreadsheet and database app builder that allows business users to create powerful spreadsheet-like applications with data links, automations, and workflows. Rachit and his team of ...
Joe Hyrkin is the former CEO of Issuu, a content publishing platform for interactive marketing content. Issuu allows you to easily publish printable and PDF materials in various formats to websites and social media. It's a global ...
Brian Hamilton is one of America’s most successful entrepreneurs and a leading expert on entrepreneurship. Today, Hamilton serves as chairman of software company LiveSwitch. He is known for his pioneering work in fintech, his advocacy for small ...
Scott Desgrosseilliers is the founder and CEO of Wicked Reports, a leading multi-touch marketing attribution software for SMBs who use paid online advertising. Scott is a data and analytics expert who saw the costly limitations of simple ...
Bryan Forrester is CEO of Boostlingo, a leading on-demand platform for live language interpretation services that is growing quickly and can become a very large company. Boostlingo now has 160 employees and over 17,000 language interpreters ...
Jason Fried is the co-founder and CEO of 37signals, makers of the popular Basecamp project management software, which is still growing and very profitable after 20 years. He is going long and still having fun as an engaged CEO, building great ...
Russ Perry is the CEO and founder of Design Pickle, the largest subscription-based business for creative design services. It's a SaaS-like tech-enabled services business that employs over 700 professional designers worldwide who can ...
Sunando Bhattacharya spent 13 years as a business leader in managed IT services companies in India before starting his own cloud tech services business. This company grew slowly and an opportunity arose to create a software product for ...
Nate Grossman and Steve Wolfe are co-founders at Growth Street Partners, a growth equity firm focused on investing in early-stage B2B SaaS companies between $2M-$6M in ARR. They discuss how growth equity funding works for SaaS founders and how ...
Raj Bhaskar is a successful two-time practical software founder with one exit. In 2000, he started his first software company, VisualHOMES, to provide comprehensive financial management software to public housing agencies. With no outside ...
Vince Hsieh is a two-time entrepreneur who has grown and sold two industrial tech companies that included software and either an RFID or GPS device in the solutions. His second venture, Geoforce, raised a non-dilutive funding round to ...
Bill Spruill had a successful sales and executive career with two exits before he and his cofounder struck out on their own in the location verification market serving financial and e-commerce companies. Sales grew slowly for several years as ...
Troy Munson has been a successful enterprise SaaS sales rep for several years, but he wanted more control over his life—and eventual financial independence. So he launched his own small startup on the side. He learned a lot and sold it before ...
Wes Bush is CEO of ProductLed, a coaching and education company that has helped almost 500 serious SaaS founders to succeed with product-led growth strategies, tactics, and execution. These include freemium products and free trials, where the ...
Michael McAllister is the founder and former CEO of The CE Shop, the leading provider of pre-licensing and continuing education for real estate professionals in the U.S. Michael started The CE Shop in 2005 by distributing existing ...
Last year I interviewed three-time software founder Matt Watson on this podcast about his successful practical founder journeys. Matt leveraged offshore software development talent in his last two SaaS companies to staff up quickly and grow ...
Eric Dill was a successful mortgage broker in Sydney, Australia, who struggled with the same painful problem as every other broker: manually checking with multiple banks to validate and price mortgages for homeowners. Eric and his good friend ...
Guy Rubin is the co-founder and CEO of Ebsta, a revenue intelligence platform that works with Salesforce and Hubspot to automatically analyze existing data to improve sales performance. Started in London in 2012, Ebsta found success in the ...
Stuart Draper founded Stukent, an innovative ed-tech company that provides simulated internships for business students. Stukent started by focusing on high-quality digital marketing education for colleges and universities using up-to-date ...
John Stewart created and sold an engineering services business, then grew a Salesforce integration services company before building some early software products. One of their software experiments allowed Salesforce customers to see and interact ...
Landon Taylor created two successful digital marketing services businesses before embarking on a product-powered business with recurring revenues. His first agency drove traffic to its customers, which led to his second business, Best Company, ...
Kyle York was the Chief Revenue Officer of Dyn, a bootstrapped cloud infrastructure company that he helped grow and sell to Oracle for over $600 million. He then led product strategy and acquisitions in Oracle's cloud infrastructure group ...
Mike Kovarik is the founder and former CEO of Attribytes, a software company he started, grew, and successfully sold in just over five years. Mike was a data analytics leader at large food distributors, where he discovered a chronic challenge ...
Brothers David and Chris Sinkinson attended Queen's University in Ontario, Canada, when David learned of the problems maintaining the blue emergency phones on campus. He proposed a location-aware mobile safety app, so Chris built it himself, ...
Dan Balcauski is the founder and principal consultant of Product Tranquility, a SaaS pricing consultancy. Dan shares the core building blocks of SaaS pricing, including customer segments, value, competition, and positioning strategy. Dan also ...
Rob Farrow was an experienced marketing executive and his wife Christina Farrow was a successful professional wedding planner. They discovered there was no good software for wedding planner pros, so they decided to build software themselves. ...
Krista Morgan started her first tech company by raising funding and trying to grow very fast. When the company faced a big issue and failed, she learned that big funding was more of a problem than a help in the growth and wind-down ...
Ian Manners was a successful consultant for pharmaceutical companies in the US when he discovered a major problem that needed a software solution. Big pharma companies provide financial assistance funding for patients who require their drugs ...
Dave Lambert and his team at Right Side Capital Management are the most active venture capital investors, having invested in over 2,000 startups since 2012. Right Side Capital is a "pre-VC" institutional investor that operates very ...
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