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Practical Founders Podcast

Practical Founders Podcast

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.
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Top 10 Practical Founders Podcast Episodes

Goodpods has curated a list of the 10 best Practical Founders Podcast episodes, ranked by the number of listens and likes each episode have garnered from our listeners. If you are listening to Practical Founders Podcast for the first time, there's no better place to start than with one of these standout episodes. If you are a fan of the show, vote for your favorite Practical Founders Podcast episode by adding your comments to the episode page.

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 carried interest.

Richard was a senior architect for a large private equity firm when he discovered this complex problem that was being managed on spreadsheets. He left to start PFA Solutions and bootstrapped the development of FirmView with consulting revenue. From inception, through growth and ultimately acquisition, Richard never took any outside funding.

FirmView adoption grew steadily, serving large private equity firms. PFA Solutions eventually grew to 34 employees before being acquired by Allvue Systems in 2024. Allvue is a private-equity-backed software company that serves the alternative investment industry.

Quote from Richard Change, co-founder and CEO of PFA Solutions

"Once you're in it, once you've decided to start a company, own it. No regrets. No one's going to save you. There's not a fairy godmother that will come and wave all your problems away. You have to own it.

"There's no magic wand that will come and wave a wand and say, OK, all your problems are solved. And that magic wand in my mind wasn't outside capital; it wasn't VC funding. That wasn't magic because what do when the money runs out?

"Is your product generating revenue? That's the real problem. If there's a problem to be solved and you have a great idea or solution, you can generate revenue from it. Prove to yourself and the world that this is viable and has product-market fit."

Links Podcast Sponsor - Cypress Growth Capital

This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast. Message Cliff Sentell at Cypress to have an open discussion about your options.

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

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Dave Lambert and the team at Right Side Capital Management are the most active venture capital investors, having invested in over 2,000 startups since 2009.

Right Side Capital is a “pre-VC” institutional investor that operates very differently from traditional VCs: investing when SaaS companies have just a little revenue using a submission form on their website, then responding quickly and making investment decisions in a week. They also invest in practical SaaS founders with capital-efficient approaches who expect to sell their companies someday for less than $100M.

In this expert episode, Dave shares practical insights for SaaS founders who don’t expect to play the big VC funding game:

  • Why raising Series A or B funding rounds from VCs reduces your odds of a successful exit
  • What founders should be focused on when they get their first customers and revenue
  • Why most VCs don’t invest when you have just a few customers and a little revenue
  • How the founders they invested in are using AI technology to grow more efficiently
  • What’s happening right now with acquisitions of SaaS companies for $25-$100M enterprise value
Quote from Dave Lambert, Right Side Capital

“More often than not, at the stages that we’re investing and someone has $4K, $8K, $20K MRR, the founders are still supremely confident and think they figured out their exact ICP and how it’s going to grow in scale. They think, We’re just going to take your money, and it’s going to be straight up from here. And it never does, or almost never does.

“We’re having conversations with founders where we’re sharing, Hey, just so you know, 90% of our companies miss their revenue targets massively in their first year. So you should assume that you are going to as well.

“But guess what? They all spend exactly what they thought they were gonna spend or more, usually. Just know that that’s gonna be the case and have a plan for where you’re still alive if things don’t go as expected.”

Links The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
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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 Angus Keatinge resolved to create a software product to solve this complicated and chronic problem.

Quickli was launched in late 2021 and it immediately gained happy customers and fans without any proactive marketing or sales. Three years later, more than 10,000 mortgage brokers use Quickli every week—that's over 50% market share. Quickli has AUD $5 million in ARR with 40 employees.

This is an amazing story of two product-focused entrepreneurs who solved a difficult problem and grew a successful software company without any outside funding. Quickli still has almost no marketing staff and no salespeople. Most of their employees are engineers working on the product and customer service.

Quote from Eric Dill, cofounder and co-CEO of Quickli

“We just cracked the $5 million ARR figure in just three years, which is a big milestone for us. We have 10,000 brokers on the platform, which is over 50% of the total market in Australia. We also have 40 employees, mostly in engineering.

“It’s been very, very much a story of product-led growth. Our product completely solves the biggest problem that every broker has every day. No other product has solved it. Brokers have been telling each other about Quickli, and we have some really big fans. It’s a very tight community of brokers who help each other.

‘How lucky did we get? Because we didn’t do anything. Almost marketing and no sales. We have a website. To say we have half a marketing person feels like an overstatement because we have a customer service person who also does some marketing on the side for us.”

Links Podcast Sponsor – Cypress Growth Capital

This week’s podcast is sponsored by my friends at Cypress Growth Capital. For 15 years, Cypress has provided non-dilutive growth funding to bootstrapped SaaS founders, including many successful founders I’ve interviewed here on this podcast.

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
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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 business and wondered why it took $10,000 and nearly a month to get professional photos for new listings. He and a cofounder started taking photos to serve busy real estate agents to learn what was needed and improve the quality and speed of delivery with technology.

Virtuance started with the vision of a software-only solution, but the business started growing with a high-quality, done-for-you service with a fast turnaround, powered by its technology, partners, and systems. The company grew steadily every year without any outside funding to eventually serve more than 20,000 real estate agents with 100 employees and more than 300 local photography partners.

This tech-enabled services company has SaaS-like gross margins. re-occurring revenue, and some profits In 2022, Jeff successfully sold Virtuance to Diakrit, a global real estate marketing technology company backed by private equity investors. Jeff stayed on for two years after the sale, until last month.

Quote from Jeff Corn, co-founder of Virtuance “The biggest reason that founders fail is that they actually fail to launch. The hardest thing to do is to fricking push your product and get it out in the world– because it’s messy. It’s certainly far from perfect, and it may not even work very well. But getting that feedback is so important to figure out what to do next.

“I see too many founders try to perfect it before they get it into the market. And then when it gets into the market, they might think it’s perfect, but the market may not. And at that point, they already invested too much in it. It’s not that we’re shipping something that we don’t think works; we are shipping something that we know checks just one of the boxes that our customers need.

“It’s just human nature that we want to put out good work, we have pride in our work. It’s one of the one of the real paradoxes of entrepreneurship is that we are all perfectionists and Type A personalities. We want to control it and we want it to be right, but also to be successful. The only way to succeed is to let go of some of that, to allow our teams to do the work, and be able to ship an imperfect product to get real feedback.”

Links The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
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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 in 2008, and Mike became the first CEO of the spinout software company, DealerBuilt.

DealerBuilt grew slowly as a bootstrapped startup in a market full of large incumbent competitors. They had a better approach to managing multiple dealers in a group with their dealer management system (DMS). DealerBuilt is powerful software that manages the entire financial operations of an auto dealer in the US.

They grew steadily to 450 dealer customers and 100 employees in 10 years before deciding to partner with ParkerGale, a private equity investor, to help them with their next growth stage in 2019. Mike continued as CEO until 2023, navigating through the COVID years and acquiring several “tuck-in” products to extend the DealerBuilt solution. Mike is now an independent advisor to DealerBuilt and other organizations.

Quote from Mike Trasatti, former CEO of DealerBuilt

“You’re constantly challenged in the entrepreneurial world. Do you really know what you’re doing? Self-doubt can be tremendously harmful to CEOs. I don’t think you can get into this business without a strong image of yourself and real confidence.

“But you have to balance confidence with humility because you’ll make mistakes. You’re going to have setbacks every week, and some very big ones, too. You can’t lose enthusiasm: You need enough confidence that you’re on the right path and that will carry you more than anything else. Those who don’t lose enthusiasm win.

“When you have both confidence and humility, you won’t be afraid to be around people who are better than you. And you’ll feel comfortable in that space, leading smart people who are championing your journey. They will look at you and think, I want to be there with you to champion this for you. That’s success as a leader.”

Links The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
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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 with their customer data on a map. When customers paid for it and revenue grew, he and his co-founder wound down services and focused on their mapping product.

MapAnything grew quickly to over $2M ARR as a bootstrapped software company, with some revenue-based financing from Lighter Capital to help test their growth plans. When they focused on field service route optimization and grew quickly, MapAnything raised several rounds of venture capital to grow even faster by focusing its sales and marketing efforts within the Salesforce ecosystem.

MapAnything reached $22 million in ARR before Salesforce acquired the company for $250 million. John stayed on with Salesforce for six months before moving on. John and a co-founder launched Fastbreak.ai three years later, a sports schedule optimization platform for professional and amateur sports leagues.

Quote from John Stewart, former CEO of MapAnything

“I tell founders most often that you really need to focus on sales and distribution. As a CEO of a startup in the tech space or SaaS, the only thing that really matters is revenue growth. Technology is technology. Even if you have unique IP right now, it won’t be unique soon enough.

“So you need to figure out your go-to-market motion. That’s the single most important thing. Revenue cures all ills. It doesn’t matter what’s going on in the company as long as revenue is growing. It’s all about revenue growth more than anything.”

Links The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.
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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 them grow more efficiently. Phil leads the GTM operations team, helping their founders scale sales, marketing, and success teams.

Phil was an experienced SaaS sales leader at several companies before joining Mainsail to focus on helping their portfolio companies scale up to $30M ARR or more. Phil’s team helps founders solve challenging problems with sales leadership, rev ops technology, compensation, marketing analysis and planning, and more with deep operational insights customized for each company.

In this episode, Phil discusses these important topics.

  • The five keys to hiring your first head of sales to graduate from founder-led sales to a scalable sales team
  • How Mainsail specialists partner with founders and their leaders to help them solve their most important GTM problems quickly
  • How Phil helps with due diligence on potential investments to assess the upsides and opportunities for revenue growth
  • Why Mainsail is focused on vertical SaaS companies with founders who are experts in their domains

Quote from Phil Stern, Operating Principal at Mainsail Partners

“Hiring a first head of sales is typically one of the first roles we're going to hire. This sales leader needs to be willing to sell the product. You're not coming in at $5 million of ARR to be an armchair VP. You own part of the quota, you're going to cover for a rep at a trade show or on maternity leave, whatever it takes.

“You have to be willing to sell. So if you come in just to strategize and move chess pieces around, it's just not the job for you.

“If you don’t sell, you won't get close enough to the customer. For these customers in vertical end markets, you need to get close to them, learn from them, understand them, and speak to them.

“It's really back to a bootstrapper mentality. The CEO has been doing absolutely everything up and down the business. I'm asking a sales leader to do everything up and down the go-to-market.”

Links

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

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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 product itself creates the awareness, engagement, and enthusiasm to buy before any human intervention (aka “the required sales demo”).

Wes has written two successful books, Product-Led Growth and The Product-Led Playbook, describing key ideas, frameworks, approaches, and examples for SaaS founders. In this expert episode, Wes shares his expertise for SaaS founders, including these topics:

  • Defining product-led growth
  • Transitioning from sales-led to product-led
  • Common mistakes in product-led growth
  • Identifying challenges and solutions for user experience
  • Pricing strategies in product-led growth
  • The future of product-led growth in SaaS

Quote from Wes Bush, CEO of ProductLed

“The PLG model you choose doesn’t matter. Not a bit. Freemium, free trial, credit card up front, whatever. You can make any of those work. That’s not the question. What matters in PLG is the actual outcome that we hope somebody will get from our product-led experience?

“Does your free motion actually have a transformation in it where they can feel they will grow bigger, save time, and do cool stuff? Because if you don’t have that, it’s literally just, “Hey, look around, see for yourself, see what you can do in this product. That’s not real value.”

“What is your PLG outcome that creates that transformation for the user? There has to be tangible value for the user before they ever consider buying. That’s what customers want when they buy software now–Show me value first before I think about buying from you.”

Links

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

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Quote from Russ Perry, founder and CEO of Design Pickle

“The game for practical SaaS founders really comes down to recognizing that there is a large market size for very boring niche companies. Finding that niche is the fastest path to success. Don’t be afraid to be boring and specific.

“If I were to do Design Pickle all over again, I would have just picked a vertical niche, like we are the graphic design provider for feline mobile cutting trucks or something. There are easily 10,000 mobile pet grooming businesses in the United States, so probably just cat groomers.

“We just went super broad when we started, and it’s been fine, but it would have been easier for us to have focused on a niche. When you have such limited resources and time and money and capital, having that narrow niche makes it easier to maximize all those dollars and investments.”

Links Podcast Sponsor – Full Scale

This week’s podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io.

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

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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 successful companies like Toast, ServiceTitan, Karbon and Dutchie.

In this episode, Dave shares some of the most useful strategic growth frameworks for vertical SaaS companies to grow through winning market share, expanding with additional products, and even extending through an industry ecosystem serving new markets. We also talk about the impact of AI on established vertical SaaS players and how it’s both an opportunity and a thre

Tidemark supports the global community of practical vertical SaaS founders by publishing their strategic growth frameworks, their annual Vertical SaaS Benchmarketing Report, and they host the annual Vertical SaaS Collective Live conference for founders.

Quote from Dave Yuan, founder at Tidemark

“Vertical SaaS founders should not be asleep with AI. You can wave it off, view it as a toy, and say that no one’s going to trust that outcome or use it. That may have been the case, but things are changing really quickly.

“Lots of smart people are making it better every month, and you have a massive opportunity to improve it with your data and workflow.

“Jump into it to control your destiny. Don’t get caught sleeping without AI in your product in a useful way.”

Links

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com/newsletter.

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FAQ

How many episodes does Practical Founders Podcast have?

Practical Founders Podcast currently has 146 episodes available.

What topics does Practical Founders Podcast cover?

The podcast is about Entrepreneurship, Podcasts, Technology and Business.

What is the most popular episode on Practical Founders Podcast?

The episode title '#92: Bootstrapped Integration Platform Growing Faster by Niching In and Doubling Down – Charlie Alsmiller' is the most popular.

What is the average episode length on Practical Founders Podcast?

The average episode length on Practical Founders Podcast is 60 minutes.

How often are episodes of Practical Founders Podcast released?

Episodes of Practical Founders Podcast are typically released every 7 days.

When was the first episode of Practical Founders Podcast?

The first episode of Practical Founders Podcast was released on Jun 19, 2022.

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