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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

01:02:42

#58: Bootstrapped a successful lawncare services...

Practical Founders Podcast ·

2023/08/25

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 help 300,000 homeowners connect with 35,000 landscape service providers. Greenpal is an “overnight success that took 10 years” while the founding team learned to build a software product and recruit homeowners and services pros to the marketplace. It grew slowly at first as they learned and made mistakes, but they didn’t

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51:14

#57: Finance, Accounting, and SaaS Metrics Basics for...

Practical Founders Podcast ·

2023/08/11

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 popular blog and podcast with free educational resources to learn advanced SaaS metrics, learn finance best practices, and hear stories from other founders. In this expert interview, I ask Ben all the questions that I hear from startup founders and SaaS CEOs about finance and accounting operations. Ben is very

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01:03:23

#56: Technical founder shares deep learnings from his...

Practical Founders Podcast ·

2023/08/04

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 startup technology teams and now is an experienced CEO and business builder. In 2021 he founded Truebase, a B2B prospecting platform for revenue teams using the power of generative AI accelerates the prospecting journey. Wissam steps back to assess his startup adventures more objectively and shares his biggest

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01:09:49

#55: Bootstrapped to $10M ARR with community-led...

Practical Founders Podcast ·

2023/07/29

Lloyed Lobo is the co-founder and former president of Boast.ai, a leading platform to help software companies in the US and Canada to redeem available government tax credits. Initially started in 2012 as a services business helping companies administer tax credits, Boast.ai was launched as a technology-powered platform that scaled their business much faster. Technology-powered Boast.ai was launched in 2017 after starting a services business in 2012 that helped larger company administer their R&D

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01:05:52

#54: Wound down a bootstrapped $1M SaaS startup when...

Practical Founders Podcast ·

2023/07/22

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 was acquired by the successful BI company Business Objects, which was then acquired by the huge software company SAP. Ryan left to start consulting and build niche add-on "feature products" in the SAP Business Objects ecosystem. They experimented with product ideas and consulting services before finding an

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37:45

#53: Insights and lessons from the first year of the...

Practical Founders Podcast ·

2023/07/14

As the host of the Practical Founders Podcast, I have interviewed 46 successful SaaS founders and 6 savvy experts in the first year of weekly episodes. In this episode, I share some of the deeper insights, surprising lessons, and useful perspective that I have learned after so many great conversations. Practical founders are building valuable software companies without big funding all over the world and in every corner of the software business. It's an amazing time to be a practical

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01:04:15

#52: Successful roofing contractor creates...

Practical Founders Podcast ·

2023/06/30

Patrick Fingles grew a successful roofing company with hundreds of employees in the Baltimore-Washington DC area. In 2013, they created their own software to help new salespeople estimate, quote, and close new roofing sales. They started selling the software to other contractors in 2016 and called it Leap. Leap grew fast to $7 million ARR in 2021 with Patrick as the CEO. In 2021, they decided to take some growth funding from Nexa Equity to give Patrick and his cofounders their "first bite" of

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01:00:26

#51: Scaling his bootstrapped SaaS company with happy...

Practical Founders Podcast ·

2023/06/23

Jordan Fleming grew up in Toronto and New York, then lived in Edinburgh, Scotland for 15 years where he created a successful consultancy helping larger businesses automate and improve their processes. His experience developing workflow apps led him and his cofounders to create a tightly-integrated phone system solution called smrtPhone built just for the Podio workflow platform, which is very popular in several industries. Jordan now lives in Poland and most of the team works in their office in

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01:08:52

#50: Serial bootstrapper sold two companies to eBay...

Practical Founders Podcast ·

2023/06/16

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, AffiliateTraction and AdAssured to eBay for an undisclosed "f*ck-ton of money," as he describes it. He is now an author, speaker, philanthropist, investor, and the creator of Startup Science and BOSS, an open-source business operating system to help more startups succeed. Gregory faced monumental

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52:22

#49: Practical investor explains the growth equity...

Practical Founders Podcast ·

2023/06/09

Deepak Sindwani is a former software entrepreneur who has been a professional investor in software companies for over 20 years. Deepak is the co-founder and managing partner of Wavecrest Growth Partners, a growth equity investor in practical B2B SaaS companies. Wavecrest specializes in helping bootstrapped and capital-efficient founders of vertical B2B SaaS companies reduce risk and grow their companies from $5M-$10M ARR to $30M-$50M ARR and drastically increase the value of their companies. Growth

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57:37

#48 – Built, grew, sold, and kept growing a...

Practical Founders Podcast ·

2023/06/02

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 team as it grew before the company was sold and now he guides the BOLT product in the larger company. BOLT was created in 2015 after years of internal use at a large Dallas-based electrical contractor. Cofounder Josh Causey brought in Sam Knight to spin out and run BOLT as a separate software company and

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57:54

#47 – How to win big when selling your SaaS company...

Practical Founders Podcast ·

2023/05/26

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 Partners where he advises smaller SaaS and tech business owners in selling their companies for successful exits between $10M-$50M. Chris got his start on Wall Street working on large finance and acquisition deals, but he quickly shifted gears 20 years ago, moved to Phoenix, and started working only with

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01:07:36

#46 – Founding couple creates valuable company, big...

Practical Founders Podcast ·

2023/05/19

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 monthly fees while they ran their services business in Scottsdale, Arizona. WordPress became popular and eventually Pagely was formally launched as the first managed WordPress hosting platform in 2009 and they closed their services. business. Pagely grew steadily until 2013, when dozens of inexpensive managed

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58:52

#45 – Bootstrapped founder still creating big...

Practical Founders Podcast ·

2023/05/12

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 new software solution for loan officers to help them educate their clients and sell more. He sold $120,000 of Mortgage Coach on stage at a conference on their first day, which started their 25-year growth journey in the software business. Mortgage Coach helps loan officers transparently present loan options and educate their

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53:29

#44 – Helping seniors tell their stories and fight...

Practical Founders Podcast ·

2023/05/05

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 she decided to create a website in 2001 that allowed anyone to journal and share their life stories. Many experiments led to her first paying customer in 2006: a senior care center that wanted to offer life journaling software to their seniors. The LifeBio software business was born. LifeBio is a leading

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55:58

#43 – A tenacious bootstrapper’s journey to a...

Practical Founders Podcast ·

2023/04/28

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 he lived there. He was a successful high school entrepreneur, then supported himself through his college years with his digital SEO agency. Their experiments with custom website quizzes showed promising results, so Josh and his cofounder friends started a company to build the first lead-generation online quizzes as a standalone

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01:00:06

#42: Second-time founder scaling up with product-led...

Practical Founders Podcast ·

2023/04/21

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 steadily and raised several rounds of VC funding to become a sizable cybersecurity software company in Silicon Valley. Cobalt serves large businesses with a platform and services for larger companies to efficiently test and find security holes in their websites and web applications. Esben left Cobalt in 2020 to

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59:36

#41: A Product Feature Experiment Turns into a...

Practical Founders Podcast ·

2023/04/14

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 Silicon Valley. While leading product at the software company MailUp, a popular Italian email marketing software, his team built and tested a better visual editor for creating email templates and website landing pages. The free software tool called BEE ("Best Email Editor") became popular and a new product line was born.

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56:13

#40: How SaaS Startups Can Grow Sales Successfully...

Practical Founders Podcast ·

2023/04/07

“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 the CEO or salespeople can close.” This is a common frustration for startup and early-stage SaaS founders when they hire sales development reps (SDRs) or business development reps (BDRs) to generate qualified leads. There are many misconceptions and pitfalls that make this even more challenging. Christine Rogers shares her

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01:16:19

#39: Former VC and funded CEO helps founders grow...

Practical Founders Podcast ·

2023/03/31

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 startups. He started his career at Hewlett Packard and experienced the famous "HP Way" culture firsthand before he attended the Stanford Graduate School of Business. He joined the preeminent tech venture capital firm Kleiner Perkins and worked directly with John Doerr for several years before launching Good Technology and

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178 results

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