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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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 … Listen to this episode
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" … Listen to this episode
Todd Watson is the owner and CEO of Showit, a popular no-code website builder and platform for designers and photographers. Todd is a native of Phoenix, Arizona where he started … Listen to this episode
Erin Fletter had a long career in the restaurant business before starting an after-school enrichment program to teach kids how to cook at her daughters' school in 2011. Her cooking … Listen to this episode
Mike Trasatti spent 10 years in the automotive dealer software business before he found an auto dealer in Iowa who had built is own complete software system. They partnered up … Listen to this episode
Brian Abernethy, founder of Utopaya, is an expert in helping SaaS leaders navigate the complicated process of adding payments monetization to their product offerings and business strategies. With a long … Listen to this episode
Jeff Corn is the co-founder and former CEO of Virtuance, one of the US's leading real estate photography and marketing providers. In 2010, Jeff was in the real estate investment … Listen to this episode
Adam Haynes is a managing director at GLC Advisors, an M&A advisory firm that helps bootstrapped founders sell their companies successfully. The GLC software advisor team has been working with practical … Listen to this episode
Matt Wolach spent 15 years as a successful SaaS account rep, sales leader, and software founder before becoming a SaaS sales coach for early-stage B2B SaaS companies. He has worked … Listen to this episode
Charlie Alsmiller is the founder and CEO of APIWORX, a powerful integration platform for mid-sized ecommerce companies. Charlie is an experienced, practical founder who has created and grown several software … Listen to this episode
David Evans, the managing partner of Sentiero Ventures, a seed fund focused on AI-focused software startups. David discusses the role of AI in software development and the opportunities it presents … Listen to this episode
Phil Dur is cofounder and managing partner of PeakSpan Capital, a growth equity investment firm that works with bootstrapped SaaS founders who are scaling up to become sizable market leaders. … Listen to this episode
Joe McMenemon and his college roommate, Brendan, knew they wanted to start a business together. They had run their college fraternity chapter and saw the problem of managing members and … Listen to this episode
Jeromy Wilson spent over ten years in the software business as a product management leader working for PE-owned and VC-funded software companies. When he decided to start his own software … Listen to this episode
Paul Van Metre was the co-founder of a successful machine shop that manufactured custom parts for the aerospace and medical device industries. Over 15 years, they created and improved software … Listen to this episode
Chris Savage is the co-founder of Wistia, a leading video marketing platform for businesses. Wistia was started in 2007 by Chris and a college friend when inexpensive cloud hosting and … Listen to this episode
Rand Fishkin is the founder and former CEO of Moz, a leading SEO software for marketers created in 2007 that grew out of the active followers of Rand's popular SEOmoz … Listen to this episode
Nathan Hirsch, co-founder of FreeUp, shares his journey of building and selling the company and his other business adventures. FreeUp provides clients with pre-vetted virtual assistants (VAs) and freelancers in … Listen to this episode
Ian Brodie, the co-founder and CEO of Levanta, shares his journey of building a successful SaaS company in the affiliate marketing space.
Levanta is an affiliate marketing platform for Amazon sellers, … Listen to this episode
Gregg Scoresby founded CampusLogic in Phoenix in 2021 to provide software for colleges and universities in the US to make it easier for students to apply for college loans and … Listen to this episode
Esben Friis-Jensen and his cofounder, Sebastian Seilund, teamed up in 2021 to create Userflow, a no-code user onboarding product for SaaS companies. This week, it was announced that Userflow has … Listen to this episode
Raj Khera is an experienced practical SaaS founder who has used search engine optimization (SEO) to grow businesses very efficiently. Now he coaches entrepreneurs at MoreBusiness on how to use … Listen to this episode
Justin Hewett started in the software business as a territory sales manager for an education software company in Utah. The company grew and Justin eventually led the sales team as … Listen to this episode
Morgan Katz is the founder and CEO of Ticketnology. Morgan was an enthusiastic athlete with a degree in sports management who started her career in ticket sales for sports teams … Listen to this episode
Stephanie Betters was a practicing Nurse Practitioner in heart surgery and an active real estate investor when her frustration with disparate real estate CRM and marketing solutions hit a boiling … Listen to this episode
Shameem Hameed created several companies, including a medical billing services company, before starting ZH Healthcare in 2008 to provide billing and EHR software to innovative healthcare providers. Their BlueBriX software … Listen to this episode
Kevin McArdle spent 15 years working in large software companies before becoming a practical investor and acquirer of very small SaaS businesses. Kevin is the CEO and co-founder of Big … Listen to this episode
Harry Hopkins is co-founder and CIO of Viewgol, a medical billing technology software and services company based in Dallas, Texas. Viewgol was started in 2017 by three founders who got … Listen to this episode
Hamed Mazrouei owned a security monitoring business and other businesses for many years before he started his first software and services business called Vivant Corporation. Vivant provides a complete turnkey … Listen to this episode
When Patrick Randolph discovered that doctors' offices lose 20% of appointments due to patient cancellations and no-shows, he set out to design and test a solution. QueueDr was created to … Listen to this episode
Raj Khera has had three exits in his long career as a software entrepreneur and leader. His first company, GovCon, grew in the late 1990s to help government contractors easily … Listen to this episode
Robin Alex worked in a digital marketing agency in Dallas when he discovered their small business clients struggled to nurture and follow up with their website leads. In 2018, Robin … Listen to this episode
Mike Roberts is the founder and CEO of SpyFu, a leading competitive research tool for marketers and entrepreneurs with over 15,000 paid customers and hundreds of thousands of free users. … Listen to this episode
Raution Jaiswal grew up in India and then worked in management roles at large companies in the US before he discovered a problem experienced by small insurance agencies. He validated … Listen to this episode
Kelly Mann was a CPA and auditor for 15 years before leaving her employer to start her own CPA firm focused on 401K benefits audits. She discovered a need to … Listen to this episode
Praveen Ghanta graduated from MIT with degrees in computer science and economics and worked for various financial services companies after trying his hand at a software startup. Working in his … Listen to this episode
In this expert interview, Vik Thapar of Cypress Growth Capital explains revenue-based financing (RBF) and how it can be very useful for practical SaaS founders. In the last 10 years, Vik … Listen to this episode
Bryan Clayton is the co-founder and CEO of GreenPal, a leading on-demand marketplace of lawn care services for homeowners across the US. With a team of 25 remote employees, they … Listen to this episode
Ben Murray is a former SaaS CFO and finance professional who helps SaaS founders understand the basics of SaaS accounting, finance, and metrics for their growing businesses. Ben has a … Listen to this episode
Wissam Tabbara is a serial entrepreneur who has created multiple software startups in Seattle since 2009 when he left Microsoft where he was a software development manager. He led multiple … Listen to this episode
Ryan Goodman joined the startup in the early days of the business intelligence and analytics market in 2003 as a specialist helping large customers adopt this new technology. This startup … Listen to this episode
Patrick Fingles grew a successful roofing company with hundreds in the Baltimore-Washington DC area. In 2013, they created software to help new salespeople estimate, quote, and close new roofing sales. … Listen to this episode
Gregory Shepard is a serial entrepreneur who has created and sold 12 companies, including marketing software and ad technology companies. In 2016, he sold two of his bootstrapped software companies, … Listen to this episode
Sam Knight is the co-founder and former president of BOLT Software, a project management and scheduling software for the construction trades that build residential homes. Sam helped lead the BOLT … Listen to this episode
Chris Kern is an expert independent M&A advisor who has helped over 150 growing tech companies get financing, obtain investment, or sell their companies. He is Managing Director of Windstream … Listen to this episode
Joshua Strebel started a small SEO and website agency in the early 2000s after graduating from university. Joshua and his wife Sally experimented with website hosting using WordPress with low … Listen to this episode
Dave Savage was a top-producing mortgage loan officer in the early 1990s who used computers and software to help him sell more. He became a software entrepreneur by creating a … Listen to this episode
Beth Sanders was selling computer software and equipment for a regional computer retailer in Ohio when she recorded her grandmother's life stories on a tape recorder. It was so powerful … Listen to this episode
Josh Haynam grew up in the Central Valley of California just 100 miles from the tech center of Silicon Valley without any awareness of tech jobs or tech businesses when … Listen to this episode
Esben Friis-Jensen was a technology professional in Copenhagen, Denmark before he and three Danish friends moved to San Francisco in 2013 to start a new startup called Cobalt. Cobalt.io grew … Listen to this episode
Massimo Arrigoni grew up in Milan, Italy, and moved to California 27 years ago to create software products and start a family, eventually moving to the San Francisco area in … Listen to this episode
"My B2B SaaS startup needs just more warm leads. But we have struggled when we hire junior salespeople to call on and email cold prospects to generate qualified leads that … Listen to this episode
Dave Whorton is an experienced tech investor and funded founder who spent the first 20 years of his career at the highest levels of Silicon Valley venture capital and tech-boom … Listen to this episode
Windermere Real Estate is a large and well-known residential real estate broker in the Seattle area. In the late 1990s, they invested to build an internal software system to power … Listen to this episode
Patrick Campbell wasn't expecting to be an entrepreneur when he grew up, but after his first few jobs, he struck out on his own in 2012 to create a software … Listen to this episode
Jon Nordmark founded eBags.com in 1998 as one of the first Internet e-commerce companies and grew it into the largest online retailer of luggage, bags, and travel accessories. Jon was … Listen to this episode
Perry Rosenbloom moved to Boulder, Colorado, in 2011 and started a small business offering digital marketing and custom website services. After building a website for his mother-in-law, an independent therapist, … Listen to this episode
Gopal Krishnamurthy was an early BI and data analytics expert working for a large company when he left to start a BI consulting company called Visual BI in 2010. Visual … Listen to this episode
Matt Watson was a two-time software company with two successful exits before he was 40 years old. He started his first company, VinSolutions, in his basement in Kansas City in … Listen to this episode
Scott McCausland was an experienced software sales leader who decided to go out on his own in 2008 to build a new software business. His technical cofounder built the first … Listen to this episode
Mark Abbott was an active investor and board member for 20 years when he realized that most of the 100+ companies he helped were not good a their "business fundamentals." … Listen to this episode
Jeff Matlow is a serial entrepreneur and a crazy triathlete and long-distance runner who found a way to put those passions together in a crazy software startup. He saw an … Listen to this episode
Howard Gottlieb created and sold several businesses before starting a school fundraising website in 2003 called Easy Fundraising Ideas. It grew into the most popular Internet website for school fundraisers. … Listen to this episode
Joe Griffin recently left his job of 8 years as co-CEO of ClearVoice, a company that he and co-founder Jay Swanson started in 2014 out of their digital marketing agency … Listen to this episode
John Francis is a general partner at Stout Street Capital, a venture capital fund based in Denver, Colorado. Stout Street has made 70 small seed and pre-seed investments in software … Listen to this episode
Zach Moreno was a full-stack developer and coding instructor in Northern California in 2015 when he discovered audio podcasts. There wasn't a remote podcast software for recording high-quality audio over … Listen to this episode
Daniel Yuabov was a 22-year-old IT manager in New York who wanted to buy a new car. He was so frustrated with the buying experience that he started a software … Listen to this episode
Seth Radman created, grew, and sold two music app startups in his twenties. A saxophone player in his college marching band, Seth was passionate about helping musicians and school band … Listen to this episode
Dougal Cameron created Golden Section to provide support and practical funding to SaaS founders with deep experience in select vertical markets. Their founder-first approach is different than the traditional VC … Listen to this episode
Sean Meister was a sales professional and leader with a successful career selling hospital and medical supplies before he left to join his long-time friend who had a vision for … Listen to this episode
Thomas Brown creatively bootstrapped his software company and ran it as a very small "lifestyle" business before committing to growing his SaaS business with a larger team.
Thomas was an independent … Listen to this episode
Nick Santora bootstrapped Curricula for five years with his co-founders before raising $3M in practical funding and then getting acquired in 2022 for $22 million.
Nick and his co-founders quit their … Listen to this episode
Jeremy Clarke created, grew, and sold his software company in a most unusual and successful way:
He grew WebMerge to $5M revenue by just himself for 6 years before hiring his … Listen to this episode
Luke Hohmann was an engineering and product management leader at Silicon Valley startups before he became an acclaimed author and speaker in the enterprise software development world. He used funding … Listen to this episode
Steve Gelley created two successful businesses and learned important lessons before he and a cofounder self-funded a third startup that was acquired in only 18 months for a big prize.
Steve … Listen to this episode
Dan Jaffe is the founder and CEO of LawLytics, a practical website marketing platform for small law firms. Dan was a practicing lawyer before he became an internet entrepreneur with … Listen to this episode
Rafael Zimberoff was CEO of ShipRush, a software company he founded in 2001, then grew and eventually sold in 2017 to Descartes Systems Group for $17 million. Rafael started ShipRush … Listen to this episode
Jonathan Cronstedt, also known as JCron, was the president of Kajabi software from 2016 through 2021 as he helped the company grow past the early startup years. JCron is a … Listen to this episode
Todd Watson is the owner and CEO of Showit, a popular no-code website builder and platform for designers and photographers. Todd is a native of Phoenix, Arizona where he started … Listen to this episode
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