Practical Founders Podcast – Details, episodes & analysis

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 does about $3M in ARR with roughly 600 dental practices and an 11-person team. The company helps dentists replace insurance-driven revenue with subscription-based patient memberships, creating higher margins and more predictable cash flow. BoomCloud has been profitable since 2016 and continues to grow steadily.

Jordon shares hard-earned lessons about hiring too fast, why systems scale better than people, and how he uses AI to increase output without adding headcount. He also shares how narrowing ICP transformed sales and marketing and why he's committed to building a durable, profitable business instead of chasing a fast exit.

Key Takeaways

• Bootstrap Talent Gap — VC-funded talent often struggles in capital-efficient environments that require ownership, speed, and scrappy execution.
• AI Is Leverage — AI tools helped BoomCloud increase marketing and product output without rebuilding a large team.
• Profit Creates Buffer — Staying profitable provided margin for mistakes and reduced stress during periods of experimentation.
• Slow Markets Matter — Vertical SaaS wins by matching the pace of conservative industries instead of forcing VC-style growth.
• Exit Isn't Required — Steady profits allow founders to "exit slowly" through distributions without selling the business.

Quote from Jordon Comstock, Founder and CEO of BoomCloud

"We say systems scale, people don't. And we're learning that now. Let's implement the systems first. It doesn't mean people aren't important. People are important. But they have to have a system or a process first.

"We've got to build it as a company and build that foundation first. When we hired a director of marketing and said, okay, you got to generate, you know, a thousand leads a month is what we were trying to do. And he couldn't do it because he didn't have systems. Fast forward a year, we implemented SEO systems to drive consistent traffic.

And we convert that traffic into leads and now a thousand leads in a month is automatic. Because we have systems. We don't have a director of marketing anymore. I guess it's me, me with systems and AI.

Links

• Jordon Comstock on LinkedIn
• Boomcloud on LinkedIn
• Boomcloud website
  

This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

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.

Wavecrest invests in vertical SaaS companies growing 30–60% annually, typically profitable or breakeven. They help founders scale sales, pricing, analytics, and leadership teams while staying capital efficient. Investments are usually $10–$30M total, with founders often taking some liquidity while continuing to lead.

Even with the excitement around AI-first companies from VCs, Deepak sees efficient growth equity in practical vertical SaaS as a great investment and a big opportunity for founders. AI is helping serious practical founders, not making them irrelevant.

Key Takeaways

• Capital Efficiency Matters — Wavecrest only backs profitable or breakeven SaaS companies that already respect the business model fundamentals.
• Founder Liquidity Helps — Taking some money off the table reduces stress and helps founders make better long-term decisions.
• Vertical SaaS Wins — Deep industry knowledge and data create defensibility AI-first competitors struggle to replicate.
• AI Is Additive — Software plus AI and data creates more value than AI replacing SaaS systems of record.
• No One-Size Playbook — Growth equity works best when strategies are customized, not forced by rigid PE-style playbooks.

Quote from Deepak Sindwani, Managing Partner at Wavecrest Growth Partners

"We don't think B2B SaaS is dead. It may create great headlines to say, AI eats software. We think software plus AI is the right approach. Software, AI plus data. So they're harvesting and creating that data moat that is going to help make them defensible.

"Then, using the AI tools, why not use the AI tools to provide more automation for customers? That's what we really think AI does: increase the ability to automate the use of their product and to get value. 

"Every company that we're involved with has some AI initiative. How am I changing how I run my business? How am I changing marketing and sales and finance and customer success using AI? Every company is doing something in every function in terms of new tools and tests."

Links

• Deepak Sindwani on LinkedIn
• Wavecrest Growth on LinkedIn
• Wavecrest Growth Partners website

This podcast is sponsored by Lighter Capital.

In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors. 

Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period.

Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals. 

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

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, bootstrapping the business from scratch.

ScaleGrid grew steadily through product depth, technical support, and Dharshan's mastery of SEO—becoming the top organic result for many key searches. The company expanded into multiple database engines, added a distributed engineering team, and reached 20 employees by 2021, serving both SMB developers and some enterprise teams. 

Dharshan sold a majority stake to Spotlight Equity Partners during the pandemic after receiving an unsolicited offer, later stepping out of day-to-day operations while remaining on the board. 

In this conversation, Dharshan shares hard-earned lessons about product-led growth, support as strategy, SEO as a long-game advantage, and how bootstrapped founders can build meaningful outcomes in massive markets. 

Key Takeaways

• SEO Power: SEO remains a long-term growth engine for bootstrappers because big VC-backed companies rarely have the patience to compound it.
• Support as Strategy: Deep, responsive technical support became ScaleGrid's differentiator and directly informed product innovation and content.
• Start at the Edges: Enterprises won't buy from a one-person startup, but edge users with urgent problems will — and they become your early beachhead.
• Bootstrap Constraints: Founder over-frugality can limit growth; strategic delegation and early team building prevent burnout and plateauing.

Quote from Dharshan Rangegowda, founder of ScaleGrid

"You can't take random people and make them an entrepreneur. You have to want to be an entrepreneur and want to be on your own. You have to enjoy the freedom and the risk and the upside that comes with it and the unmitigated downside as well. You have to accept and be comfortable with it. 

"You want to be on your own so you can try things. You are constantly looking at problems and new solutions. You want to be around people who like that sort of process: Here's a new problem and here's a new solution. 

"But the most important thing you have to do as an entrepreneur is you have to add value to your customers. And most people forget that."

Links

• Dharshan Rangegowda on LinkedIn
• ScaleGrid on LinkedIn
• ScaleGrid website
• Spotlight Equity Partners (acquirer)
• Allied Advisers (M&A advisor)
• AngelPad Accelerator

This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical.

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.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Antony Ceravolo is a successful two-time startup founder from Adelaide, South Australia. He started his career in investment banking but left in 2002 to start a DVD rental business in London that raised funding from big VCs and Amazon. It grew into Lovefilm.com, which was later acquired by Amazon in 2011 to become part of their movie streaming service. 

He moved back to Adelaide and started Sine in 2013 to help schools, businesses, and large office buildings manage guest sign-ins more securely using iPads at their front desks. They also started tracking visiting contractors and vendors with their mobile app, allowing automatic check-ins and tracking for operations managers.  

Sine grew quickly with global customers and large deals, eventually growing to 100 employees, mostly in Adelaide, with no VC funding or institutional investors. Sine was acquired by Honeywell in 2020 and became a critical product in their property management technology suite. 

Antony speaks openly about the benefits and challenges of working with institutional investors and why he avoided raising VC funding with Sine. 

Learn more at practicalfounders.com. 

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 organic SEO as a core part of their marketing engine. 

In this expert interview, I ask Raj to explain the basics of SEO for SaaS founders, what tools and techniques are most useful, and how SaaS founders can make the most of SEO investments to drive revenue faster.

SEO for Bootstrapped SaaS Topics Discussed on this Podcast

• How he used SEO to grow his previous software companies
• The basic concepts of search engine optimization (SEO) for SaaS founders
• Simple tactics for identifying search terms that would create qualified traffic
• His favorite tactic for gaining authority from Google for your organic website content
• Which search engine marketing tools are most useful to maximize your time and investment
• The simple ROI math that founders can use to measure their investment return with SEO

Learn more at practicalfounders.com. 

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 the senior executive. When the company was acquired by PE investors, Justin moved on in 2020 and thought about ideas for a new software business to serve K-12 schools in the US. 

Flashlight Learning helps K-12 teachers in the US to quickly assess the speaking and writing progress of multilingual students who are learning English. The software captures data for teachers to provide students with improved feedback to accelerate language development.

Flashlight Learning grew 300% in 2023 to $4 million in revenue, with a growing team and an outsourced development partner. Justin raised some angel funding to get started and move fast, but they are expecting to be profitable this year with continued growth.

Learn more at practicalfounders.com.

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 and front-line venue management. Morgan saw how companies with season tickets had difficulty managing their digital tickets after COVID, so she started her own company to solve it with a software solution. 

Ticketnology is a fast-growing leader in the new category of season ticket management software. Started with a mix of hands-on concierge services and a software solution, Ticketnology is now a complete platform that helps season ticket holders manage and distribute tickets to maximize the value of their season ticket investment. 

Ticketnology is a bootstrapped and profitable software company with just over $2 million in revenue, four full-time employees, and an outsourced development team. They doubled revenues this year and expect to double each year for the next few years. Morgan is a member of a Practical Founders Peer Group. 

Learn more at practicalfounders.com.

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 point. Salesforce and a development partner proposed a project so expensive that Stephanie hung up and decided to build the solution herself. She learned to code and build a useful real estate CRM on Salesforce in three months.

Her business thrived with her comprehensive software. Other real estate investors heard about her software and encouraged her to launch the company in 2019 and start selling the software, now called Left Main REI. Word spread in the industry and hundreds of real estate investors signed up in the first year, transforming their businesses. 

In just over three years, Left Main REI now has hundreds of customers, 20 employees, and nearly $3 million in annual recurring revenue. The company has been bootstrapped and profitable from the first day. Stephanie has a big vision for the company and loves her founder/CEO role; she will no longer be practicing as a Nurse Practitioner as of 2022. 

Learn more at practicalfounders.com. 

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 grew into a comprehensive and customizable platform used by hundreds of healthcare organizations around the world. 

ZH Healthcare now has almost 200 employees in the US and India. The company has been profitable every year and has not taken on any outside funding. 

Kevin McArdle spent 15 years working in large software companies before becoming a practical investor and acquirer of smaller SaaS businesses. Kevin is the CEO and co-founder of Big Band Software, a holding company that buys and holds small, profitable, and growing SaaS businesses—with no intent of selling those businesses. Kevin has acquired over 40 businesses in the last 10 years with this buy-and-hold model. 

As an expert guest on the podcast, Kevin answers common questions from practical founders about the holding company approach as an exit path. Holding companies are common in other industries, including Warren Buffet's Berkshire Hathaway, but relatively new to the software industry.

Learn more at practicalfounders.com.