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.

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 the product and revenues going before hiring additional staff. Their revenue cycle management (RCM) analytics software reveals medical billing problems and missed revenue opportunities at physician offices in the US.

As the company expanded its service offerings, Viewgol grew very quickly, from three employees in 2019 to almost a thousand employees at the end of 2023. Viewgol was acquired in October 2023 by CPSI, a public medical billing solutions company, for a reported $67 million in cash and earnouts. 

Hamed Mazrouie 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 multi-site internet phone system to thousands of restaurants and law firms across the US. Vivant grew steadily and profitably for 10 years and is now a maturing business with 50 employees. 

In the last four years, Hamed and his growing team have been building Milagro, a complete restaurant management system to increase repeat customer business. They now have happy paying customers who use their powerful software which includes advanced data analytics. Their vision is expanding based on early customer results. 

Learn more at practicalfounders.com.

Subramanyam Kasibhat has created dozens of products in many different industries. He and his wife were contracted by a friend to build a software solution for a manufacturing plant for a German company. Seven years after they started with their first customer, they rewrote the software to serve other customers and the Vegam Solutions business started to grow. 

Vegam Solutions is smart factory software for digital optimization and control of complex manufacturing plants. Vegam now has 180 remote employees, primarily in India, with almost $10 million in revenue. They have grown without outside funding by selling to large customers with complex needs.

Learn more about practicalfounders.com.

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 banking and tech M&A, Gaurav is a sell-side advisor to B2B software founders who have built successful businesses and want to explore selling their companies.

Allied Advisers typically works with founders selling their businesses for $20M–$200M, helping them prepare materials, run a competitive process, and negotiate terms.

We discuss how today's M&A market looks very different from the 2021 bubble. Valuations have normalized, deal timelines have increased, and buyers are more disciplined. But the demand for profitable, steadily growing SaaS companies is stronger than ever.

Gaurav breaks down strategic and private equity buyers, what metrics matter most, how AI influences valuations, and why most founders underestimate the emotional and operational effort required to sell. For practical founders thinking about an exit in the next few years, this episode provides clear expectations and tactical guidance.

Key Takeaways

• Profitable Growth Wins — Buyers prefer SaaS companies growing 20–50% with real profits over faster revenue growth fueled by burn.
• Metrics Drive Valuation — Net retention above 110%, gross retention above 90%, and >75% gross margins increase valuation and buyer interest.
• Run a Real Process — A single buyer gives you no leverage. Multiple qualified buyers improve pricing, terms, and closing certainty.
• AI Is Lipstick — But Real — You don't need to be AI-native. Practical AI that improves product, margin, or GTM still increases buyer interest.

Quote from Gaurav Bhasin, founder and managing director of Allied Advisers

"The good news for SaaS founders is that the private equity community has raised about $1.5 trillion of capital, and more is being raised. And they also have access to debt. So there's $7 trillion of dry powder to do deals. Private equity is not paid to sit on the cash. And they love recurring revenue software. 

"Private equity investors will typically move much faster than strategic buyers. Strategics will take a while. You need a business unit sponsor to buy into the vision, and then they will push the corporate to do the deal. But with the private equity, they will look at your financial metrics and if you fit in, they can move pretty fast. 

"The one caveat with private equity compared to strategic is they generally pay a little bit less than the strategics because strategics have established distribution and GTM for higher growth, so private equity will index more on the financials."

Links

• Gaurav Bhasin on LinkedIn
• Allied Advisers on LinkedIn
• Allied Advisers website
• 2025 Vertical SaaS Report - Allied Advisers

This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent.

Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out.

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.

Jafar Owainati was a mechanical engineer before he got an MBA in entrepreneurship and decided to start a software company with two friends. They looked at many ideas before building software to help sales engineers respond to Requests for Proposals (RFPs) faster and easier. They launched Loopio in 2014 and had paying customers within one year. 

The three founders built the software and sold the first customers before adding more employees as they approached $1M ARR. They kept growing faster with a disciplined and frugal approach to $3M ARR before raising a round of VC funding from OpenView Ventures, a practical investor that aligned with the vision and approach of Loopio's founders. 

Loopio now has hundreds of employees and Sumeru Equity Partners made a strategic $200 million private equity investment in 2021. Jafar left to start a compensation management software company called Barley which is starting to grow quickly now.  

Learn more at practicalfounders.com. 

Miles Schwartz a cofounder of Zūm Rails, a fast-growing fintech based in Canada with a growing worldwide presence. In just 3.5 years and without any outside funding, Zūm Rails has grown from a focused startup to a credible open banking and instant payment gateway with $10M in ARR. Zum Rails also integrated KYC (Know Your Customer) technology which reduces fraud across all payment types. 

Miles and his cofounder had experience with fintech payments before they started Zum Rails to improve EFT payment processing in Canada. As they worked with more partners and grew revenues, they expanded the Zum Rails solution and built relationships with larger partners.

Fast-growth, larger partner opportunities, and traction with a US expansion are causing Miles and his cofounders to think differently about the potential for the company and potentially raising growth capital from the right VC investment partner. 

Learn more at practicalfounders.com. 

Bernardo Carvalho Wertheim is a worldly entrepreneur who grew up in Sao Paolo, Brazil, and then moved to the UK to go to school and start his career in advertising. He kept traveling and eventually settled in Santiago, Chile, where he started a tech startup and participated in a tech accelerator. 

The Bridge started as a community and jobs platform connecting UX designers in Latin America to work at startups and large agencies worldwide. They expanded the services offerings and eventually grew to $10 million in revenue by helping to employ hundreds of high-skilled remote creative professionals. 

In 2023, the Bridge was acquired by Gi Group, a large Italian HR services conglomerate that wanted to expand its footprint in Latin America. Bernie stayed on to help The Bridge serve a global audience and work with other Gi Group organizations across Europe and Latin America.

Learn more at practicalfounders.com. 

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 fill those open slots with patients in the waitlist "queue."

With just a little funding and lots of hard work, they began by helping small practices and group practices fill open slots with no human intervention. Eventually, they sold to larger organizations and became profitable as they grew. QueueDR was acquired by Phreesia (PHR: NYSE) in March 2021 for an undisclosed amount. 

Topics discussed on this podcast

• How he prototyped and designed the full product before writing any code
• The multiple challenges of selling technology to healthcare providers
• How they started by selling to small offices and eventually sold enterprise deals to large organizations
• Why he didn't want to raise another round of VC funding after raising $1 million from an investor
• How he developed the relationship with leaders at the company that eventually acquired QueueDr
• How he thinks about life after selling his company

Learn more at practicalfounders.com.

Raj Khera has had three exits as a software entrepreneur and leader in his long career. His first company, GovCon, grew in the late 1990s to help government contractors easily access new contracts up for bid by the US government. Their advertising and subscription revenues grew quickly, and he sold GovCon in 1999 for $12.5 million. 

He bootstrapped one of the first email marketing software businesses in the early 2000s called MailerMailer to help small businesses send emails. Raj and his brother Vik ran this as a profitable small business for many years, giving them an interesting business challenge while not sacrificing time with their families. After running the business for 15 years, Raj sold MailerMailer to a public software company, J2 Global, in 2017.

Then Raj joined a struggling VC-funded software company called WealthEngine to help grow sales, create new products and exit. Wealth Engine was successfully sold in late 2020. Raj is now an active advisor to software founders. At MoreBusiness.com, he coaches software founders to efficiently acquire customers using advanced search engine optimization and marketing techniques. 

Learn more at practicalfounders.com.

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 and two developers prototyped a marketing automation and CRM software that could help other agencies solve this problem for their clients. They pitched the product and got a great response. They built their first product and HighLevel grew quickly. 

HighLevel grew fast as word of mouth and referrals spread in the agency community. HighLevel is an all-in-one sales and marketing platform for agencies that serve small businesses. With marketing automation, CRM, and payment tools, HighLevel has an innovative "white-label" platform that their agency customers rebrand to deliver custom solutions to their customers. 

HighLevel has over 60,000 agency customers, over 3 million small business users, and over 700 remote employees. HighLevel is adding 30-50 employees a month, yet they are still "moving fast and breaking things" to move fast and serve their agency customers. The founders took a practical growth equity round of funding in 2021 from PeakEquity.

Learn more at practicalfounders.com.

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. SpyFu was launched in 2006 and has been a profitable and bootstrapped business for almost 18 years. 

Mike is a happy founder who splits his time between leading the business and his personal pursuits, which include surfing and spending time with his family. He is still passionate about innovation, search marketing technologies, big data and AI, and creating new ways to help smaller businesses succeed. 

Learn more at practicalfounders.com.

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 the problem, built an early solution, and didn't quit his full-time job in 2018 until he had 50 paying customers.

InsuredMine provides an all-in-one sales CRM (customer relationship management) and marketing automation software for independent insurance agencies in the US. InsuredMine helps improve and automate marketing, sales, and service to help insurance agencies sell more, serve customers better, and become more profitable. It also integrates with many popular agency management systems (AMS).

The bootstrapped company is growing up quickly with almost 60 employees, a leadership team, and a growing reputation. In addition to over 1,000 small insurance agency customers, InsuredMine is now being used by some of the largest agency organizations in the US. 

Learn more at practicalfounders.com. 

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 automate this process, validated the market with other CPAs, and created the first AuditMiner software.

Unfortunately, Kelly was diagnosed with Stage 3 breast cancer just before launch and started aggressive chemotherapy immediately. After a year of treatment, AuditMiner was launched, and CPA firms lined up to buy it. 

With her treatments and surgeries behind her, Kelly is now CEO of a fast-growing and profitable SaaS software company with 15 remote employees, hundreds of customers, lots of publicity, and suitors interested in buying the company.

Kelly openly shares her personal journey with cancer and how she thinks differently about running a software company than most founders. 

Learn more at practicalfounders.com.

Praveen Ghanta graduated from MIT with computer science and economics degrees and worked for various financial services companies after trying his hand at a software startup. Working in his spare time, he built a product and recruited a cofounder to help sell it. After trying to sell it to different types of financial services companies, they finally found a valuable use case with individual wealth managers to help them sell new clients. They quit their jobs and launched HiddenLevers.  

HiddenLevers was as stock portfolio and financial risk management software that helped financial advisors show their clients the potential impact of outside invents on their investments. Despite being bootstrapped and profitable, the company grew steadily to $8M ARR with 25 employees by selling to larger wealth management companies and solving bigger problems. 

Orion Advisor Solutions acquired the company in March 2021 for a strategic valuation of 16X revenues. HiddenLevers is now Orion Risk Intelligence. After helping the acquisition transition, Praveen started Fraction to help software companies hire senior developers looking for ongoing fractional engagements. 

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 identified the fragmentation of the creator tools market — which led her to build Rella 1.0. 

With some small seed funding, the first Rella version focused on content creators and made no revenue with a freemium model. With $25K in the bank and no revenue, the four cofounders thought they would shut it down. But a viral video focused on social media teams immediately created paid users and revenue for a new Rella product.

"Rella 2.0" now offers all-in-one content planning, scheduling, collaboration boards, billing & analytics, an AI content strategist, and all in one workspace — for social media teams. In just 12 months, they went from having no revenue, no funding, and a hard pivot relaunch to almost $3M in ARR run-rate revenue — with only four co-founder employees.

Key Takeaways

• Charge Early: They learned the hard way that free users don't convert — monetization early was non-negotiable.
• Lean Teams Win: A small, focused team aligned tightly with a mission beats trying to scale prematurely.
• Community Is Fuel: Natalie shared behind-the-scenes of the product with early users — built trust + word-of-mouth.
• Pivot Smart: They transitioned from creator workflow tools to a full SaaS platform after validating demand.

This Interview Is Perfect For

• SaaS founders pivoting after a stalled product
• Founders learning how to find product-market fit 
• Teams deciding when to hire or stay lean 
• Builders designing tools for marketing and content teams

Quote from Natalie Barbu, founder and CEO of Rella

"It was about two years before we decided to pay ourselves. I was still making money from my social media. So that's how I supported myself. And then my co-founders had to find side things, which I know a lot of people say, you have to be a hundred percent all in and invested in it. 

"But when you're not making money, you need to find a way to support yourself. So yeah, they had some side gigs that they were working on while still working full-time on Rella.

"Once we started making more money with Rella 2.0, we all bumped ourselves up and got some raises since we could afford it, which has been such an accomplishment. It's money that we're actually making from our customers and our users and the income that we're generating."

Links

• Natalie Barbu on LinkedIn
• Rella on LinkedIn
• Rella website - Use this 10% Discount Code for Rella -  practical

This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/

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.

Oliver Low worked for Microsoft and then MySpace in London before creating a successful digital agency in 2010 with two friends. Their agency grew fast and was profitable, so they invested in building software apps to solve problems that they faced helping big brands promote on the web. One of those products, Platform360, turned into a real SaaS product business which became their focus in 2013.

Platform360 was a programmatic ad platform for large brands to manage digital advertising in the changing digital privacy environment. They grew quickly with extreme effort and no outside funding, but eventually decided to sell the Platform360 business in 2018 for a modest exit.   

Oliver is a savvy and practical "0 to 1" entrepreneur and business builder. He now runs Tiny Studio, the venture builder inside Tiny.com. Tiny is one of the largest "buy and hold" acquirers of bootstrapped and profitable SaaS companies, continuing to run those companies as independent and sustainable businesses. 

We talk at length about what we are both seeing in the big wave of successful practical software companies that are starting, growing, and thriving without any VC funding. 

Bootstrapped SaaS Topics Discussed on This Podcast with Oliver Low

• Why Oliver created a digital agency in 2007 after working at Microsoft and Myspace
• How they built and grew a programmatic ad-tech platform without outside funding
• Why they chose to sell the company at a challenging time rather than raise big VC funding
• How Tiny.com works as a holding company that acquires bootstrapped SaaS businesses and holds them long-term as independent companies
• What Oliver sees in the world of practical SaaS founders from his global perspective
• Why he started a venture studio inside Tiny.com to incubate practical SaaS businesses

Learn more at practicalfounders.com. 

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 and the Cypress team have funded over 50 SaaS and tech-enabled services businesses that have steady recurring revenues and predictable customer acquisition approaches. 

Revenue-based financing is a form of non-dilutive funding that is paid back as a fixed percentage of cash receipts until the investment is paid off. 

Unlike raising funding from VC or other equity investors, founders with $3M-$10M ARR can use RBF as an efficient option to accelerate growth and increase the value of their companies without losing control or diluting their equity.

Royalty-Based Funding Topics Discussed on This Podcast

• What is royalty-based financing and how is it different than other non-dilutive funding options like venture debt or equity funding from VCs?
• When is royalty-based financing useful for practical founders by company size and capital needs?
• When doesn't royalty-based financing make sense for founders?
• What time frame is typical for founders to use funding to grow and then exit at a much higher price?
• What has happened in the royalty-based financing industry in the last 10 years?
• What's the typical process and timeline for a founder to receive funding and start paying it back?

Learn more at practicalfounders.com.

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 stop and started to expand regionally. Greenpal has no outside funding. 

Bootstrapped Marketplace Topics Discussed on This Podcast

• How long it took the founders to get the Greenpal marketplace going in his home city before adding other cities and going national
• Why they are laser-focused on one segment of this massive landscape maintenance industry
• How a two-sided marketplace business is different than a B2B SaaS business
• Why they resisted taking outside investment for all the years it took them to become profitable
• Why he has "fun" working so hard for so long to make GreenPal successful

Learn more at practicalfounders.com. 

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 experienced and very practical about doing the simple practices that help software companies grow efficiently and confidently. 

Learn more at practicalfounders.com. 

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 learnings around leveraging the latest technologies, funding, and acquisitions, and staying ahead of giant tech companies in the same space. He talks about his biggest learning as a technical founder: how the revenue and growth side of the business is where "all the action is at" when creating a valuable software company. 

Learn more at practicalfounders.com.

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 tax credits. Boast.ai bootstrapped their growth to $10 million ARR before taking an investment from Radian Capital that also allowed Lloyed and his cofounder to cash out some of their equity for life-changing cash payouts. Their growth was fueled by the active startup community they built called Traction. 

Lloyed faced many challenges as an immigrant, startup adventurer, frugal entrepreneur, and hyperactive community builder. He also struggled after the investment when he finally had monetary wealth and experienced depression. With the support of his family and therapy, he moved forward to prioritize his health and family and limit his startup addiction. 

Learn more at practicalfounders.com. 

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 opportunity to help Business Objects users easily visualize data on Google Maps. They grew fast as an add-on product selling to large companies all over the world, reaching 700 customers and $1.4 million ARR. But new BI platforms and technology changes slowed their growth and completely changed the market opportunity. 

Ryan talks about the pivots and experiments they tried before deciding to shut down the company and sunset their core product. He shares his difficult decision process and the emotional journey, including lessons learned and perspective gained in hindsight. 

In this episode, Ryan explains:

• How he started in the pioneering early days of business intelligence and analytics for big customers
• Why he left SAP after being acquired twice to start his own add-on software business in the Business Objects community
• How he experimented and survived long enough to find a compelling product opportunity that quickly grew to over $1M ARR
• How the market changed and how that eventually led him and his cofounder to shut down the business slowly
• How he feels about the successes and failures of his software startup journey

Learn more at practicalfounders.com. 

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 founder. Practical founders are solving problems, changing the world, and doing it their way.

The founder equity value and founder wealth created by just the 46 founders I interviewed this year is over $1 billion. Tune in to this episode where I share what's going on right now and how these founders are succeeding in their own ways.

In this episode, Greg explains:

• What characteristics that all successful practical founders have in common
• Why there are so many variations and ways to create a successful software company when you don't raise big funding
• What has happened in the last 5 years that makes it better for most new founders to grow a serious software company without big funding
• Why we don't see the hundreds of billions of founder equity value and wealth that have been created by practical founders who have grown thousands of valuable software companies without big funding

Learn more at practicalfounders.com.

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 successful liquidity and support future growth and acquisitions.

Leap is now the leading contractor management software with CRM, project management, and point-of-sale functionality specifically designed for the unique needs of home improvement contractor and remodelers in the U.S. Leap is now over $20 million in ARR with over 150 employees and full-time contractors and is still growing fast. 

Learn more at practicalfounders.com. 

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 Romania. 

The bootstrapped and profitable smrtStudio Global company is now growing fast with 2400 customers, 45 employees, and nearly $5 million in ARR (annual recurring revenue). They are very disciplined about company culture, building a scalable organization, growing employees, and preparing for growth before problems arise.

Learn more at practicalfounders.com. 

In this episode, the founder of Practical Founders, Greg Head, shares the most powerful insights from over 165 podcast interviews and working with 40+ bootstrapped SaaS founders in his peer groups. Greg breaks down the common but less obvious traits he sees in practical founders who are quietly building valuable software companies without big VC funding.

Greg shares how frugality and managed risk-taking coexist to create compounding steady growth, creating massive long-term value fpr practical founders. And independence and doing it your way are not just luxuries but real superpowers that fuel growth. These patterns have emerged across hundreds of founders he's worked with, representing over $10 billion in founder equity value created.

For SaaS founders skeptical of VC templates and PE playbooks Greg shares what all practical founders do to grow from $1M to $10M ARR without betting it all. Are you wired like a Practical Founder?

Key Takeaways

• Frugal yet bold – Practical founders are unusually frugal in life but make well-timed bold bets inside their companies.
• Managed risk – They avoid betting the whole company, instead making small bets that can compound into larger wins.
• Compounding focus – Long-term, steady 20–30% growth creates exponential outcomes in SaaS over 10–15 years.
• Independence premium – Protecting their ability to do it their way is treated as a strategic advantage.
• Optionality matters – Practical founders value flexibility to sell, go long, or change direction without outside control.

This Interview Is Perfect For

• Founders building SaaS without VC funding
• CEOs who value control and sustainable growth
• Entrepreneurs exploring long-term leverage vs. quick wins
• Anyone who wants to understand the practical founder mindset

Quote from Greg Head, founder of Practical Founders

"The simple math of a $1 million ARR recurring revenue business that grows at 30% a year, will become very valuable if it keeps growing. ? Not crazy growth, a reasonable pace. This is the fundamental principle of recurring revenue businesses, that it's a compounding machine. 

"If you grow at 30% for nine years, you'll have a $10 million business. And if you do that for another nine years, you will have a $100 million business. That's probably worth a billion dollars by that time. That sounds simple and not everybody gets there, of course, but practical founders think in this way. Steady, healthy compounding. 

"We know that in the long run, the 10 years, the 20 years, compounding makes the difference. It's a healthier approach. We actually like this approach, generally speaking. We understand the math and yes, we're doing it. Most people don't really sign up for this kind of thing."

Links

• Greg Head on LinkedIn
• Practical Founders on LinkedIn
• Practical Founders 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.

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 challenges as a child growing up in poverty with a rare combination of autism, dyslexia, synesthesia, savant syndrome, and other neurodivergent conditions. He learned to develop himself and overcome big challenges, including creating, growing, and running many software companies over three decades. 

In this interview, Greg shares his difficult personal challenges and his successful entrepreneurial journey as an experienced practical founder. He also shares several powerful insights and approaches for bootstrapped software founders that you won't hear from investors or the current startup education.

Learn more at practicalfounders.com. 

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 equity funding is a practical version of institutional funding that is different than traditional "Get Big Fast At All Costs" big venture capital approach. With more reasonable growth and exit expectations, more help for founders and their teams, and more secondary for founders (to take some money off the table), growth equity partners can help ambitious founders scale their impact with an efficient approach. Unlike private equity (PE) majority acquisitions and "roll-ups", growth equity investors want to grow businesses organically and support the founders in their journeys. 

This is an expert interview in which I ask Deepak to educate us about the growth equity funding game and answer typical questions for founders who are considering taking on a funding partner to efficiently accelerate growth after they reach $3M-$5M ARR. 

Learn more at practicalfounders.com. 

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 grow the customer base and improve the product. Through 2020, the company grew to over $1M in recurring revenues before it was acquired in 2020 by Fort Worth-based ECI Solutions to expand its construction software offering.

Built by the trades for the trades, BOLT is a SaaS solution that simplifies project management, scheduling, and estimating for new home construction subcontractors (electricians, painters, plumbers, etc.). BOLT helps those subcontractors truly manage their teams: from rescheduling due to unforeseen delays to scheduling out multiple crews simultaneously.

Learn more at practicalfounders.com.

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 small software companies with growing SaaS, software, and technology businesses. I have known Chris for over 15 years.

In this interview with an active M&A professional who helps many practical SaaS founders sell their companies every year. I ask Chris the most common questions I hear from practical founders who are thinking about selling their companies someday.

"There are a thousand times more companies getting acquired for less than $50 million than all of those that sell for billion-dollar valuations. You just don't hear about these deals because they are smaller and often have confidentiality agreements in place," Chris explains.

In this episode, Chris explains:

• What's happening right now in mergers & acquisitions of software, SaaS, and fintech companies that sell for $10M to $50M?
• What are common valuations ranges for software startups and small companies with revenues between $500K and $5M in ARR?
• What are the factors that affect valuation one way or the other?
• Can you really sell a startup for a multiple of revenues when it's still small?
• Who is buying these smaller software companies and why are they buying them?
• What is the general process of selling your company?
• What should they be thinking about before they try to sell to maximize their outcome?
• Is it better to have outside funding or to have bootstrapped when selling your company?

Learn more at practicalfounders.com. 

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 WordPress hosting competitors entered the market, all backed by big VC funding. Pagely was bootstrapped with no outside funding, so they slowly changed their focus to serve only the biggest companies the largest WordPress sites with the most complex needs. Pagely revenues grew 1000% in just 3 years after focusing on the top 1% of WordPress customers.

Pagely was profitable and sustainable with many big-brand large customers when they sold the company in 2021 to GoDaddy, the huge website hosting company also based in Arizona. With nearly $10 million in ARR, Pagely's strategic exit created generational wealth for Joshua and Sally and life-changing wealth for multiple key employees.

Learn more at practicalfounders.com.,

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 clients about the financial impact, which differentiates the loan officer and helps them increase sales and referrals. It started as Windows software then eventually transitioned to the web and mobile devices.. The company grew steadily until the mortgage meltdown in the Great Financial Crisis of 2008-2010 caused its sales to plummet, but it didn't kill the company. After 2012, they started selling to large lending companies, not just individual loan officers. 

Mortgage Coach was a growing and profitable software company with no outside investors when a majority of the company was acquired by private equity investor LLR Partners in 2021. Dave is no longer the CEO of the new company called Trust Engine but he is still is part-owner and an active executive leader helping to grow the impact of the new company. 

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 "agetech" software that uses Reminiscence Therapy Method and storytelling in various media to help older people to capture and share their life stories. LifeBio's autobiography tools are also used by the Mayo Clinic and other organizations serving Alzheimer's patients. During the COVID crisis, LifeBio launched MyHello, a new software app that helps seniors fight loneliness. 

LifeBio has grown steadily and profitably to over $2 million in revenue with 48 employees, based in a small town near Columbus, Ohio. Mostly self-funded with a little angel funding, LifeBio serves the massive senior care industry in the US with its easy-to-use apps and tools. Their mission is to help people tell their life stories and share them with their own families. 

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 plugin for websites.

Interact quizzes showed promise with great customer value, but they struggled to sell their new solution to small business owners or marketers who had never seen quiz software before. They experimented, pivoted, and kept going for seven years before they finally reached $1 million ARR with some profits. The ups and downs continued with well-funded competitors, COVID booms and busts, target market pivots, and more.

Interact now is profitable and growing with nearly $3 million in annual recurring revenues, 11 remote employees, and thousands of customers—still without any outside equity funding. Every day, users complete millions of Interact quizzes on their customers' websites.

Learn more at practicalfounders.com.

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 start Userflow to help software companies attract, sell, onboard and support their customers without human touch altogether using a product-led growth approach. Userflow is a no-code onboarding software to easily build in-app explanation guides, checklists, and videos for software product companies to improve free trial conversion and new customer onboarding for expanded retention. Userflow has a free trial and uses its own software to improve conversion and onboard customers without human intervention.

Userflow is profitable and growing with over $3 million in ARR, 600 customers, and just three employees with no outside funding. Esben handles all growth and lives in San Francisco and his cofounder Sebastian builds the product with their UX designer in Denmark, so about $1 million annual recurring revenue per employee.

Learn more at practicalfounders.com.

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. 

BEE end users love the modern and easy-to-use no-code editor which doesn't require email or credit card to use the product for free. The company also sells to SaaS developers who want to embed the BEE builder into their own apps instead of building their own visual editors. BEE is growing with no paid advertising or marketing spend. New users find their free template library and start to use the product instantly with a frictionless experience. 

Businesses now pay for the BEE Pro solution making up about half of company revenue and embedded plug-in makes up the rest. BEE is now a standalone company owned by parent Growens with 80 employees and over $10M in revenues. BEE has over 40.000 monthly users and 10,000 paying customers. 

Learn more at practicalfounders.com.

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 ago after careers at Fred Hutchinson Cancer Research Center. They built DFnet around long-term client relationships in global health and clinical research.

The company runs DFdiscover, an enterprise-grade electronic data capture and management platform used in clinical studies worldwide. With offices in the U.S., Canada, and South Africa, DFnet has grown to more than 50 employees and is approaching $10M in revenue. Clients range from the U.S. Department of Veterans Affairs to nonprofits like PATH and major universities.

Still independent and bootstrapped, DFnet has made key moves to prepare for the future—such as bringing in a growth-focused CEO, diversifying beyond single-client risk, and shifting legacy software to SaaS and services. Darryl shares the lessons from running conservatively under debt, buying rather than building, and building a global company rooted in relationships and practical execution.

Key Takeaways

• Stability First Growth – Carrying a 10-year SBA loan forced conservative growth and taught the discipline of stability over risky expansion.
• Buying Not Building – Acquiring DataFax brought 35+ new clients overnight and proved that buying legacy software can be smarter than reinventing.
• Services Plus Software – Unlike pure SaaS, DFnet thrives by combining consulting, hosting, and software in a regulated field.
• Spouse Founders Structure – Their 51/49 ownership split avoided deadlocks and kept marriage and business aligned.

This Interview Is Perfect For

• SaaS founders balancing growth and control
• Founders considering succession or sale
• Bootstrapped entrepreneurs in niche B2B markets
• Anyone curious about global health data and impact-driven tech

Quote from Darryl Pahl, co-founder of DFnet

"The best position to be in is to say that in three to five years, we would be crazy to sell this company. It's doing so well. That would be the perfect thing. And what we're not looking for is a giant payout. We have a very modest lifestyle.

"But is an asset, it is a business, and there's a business aspect. It would have to be the right type of buyer. It has to be the right fit. It has to be the right person or group that is respectful to our clients, our employees, and us as owners. 

"So the ideal would be to have the luxury of either not selling or being more selective rather than responding to random emails from some financial buyer or search funder."

Links

• Darryl Paul on LinkedIn
• DFnet on LinkedIn
• DFnet website

This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent.

Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out.

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.

"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 expertise on what is working and not working when hiring SDRs to generate or warm-up leaders in the modern software business. Christine is an experienced SaaS sales leader who has helped develop thousands of SaaS sales and SDR reps to succeed at growing software companies through her company Aspireship.

In this episode, Christine explains:

• What are the different tasks and roles of sales development reps (SDRs) and business development reps (BDRs) in growing SaaS companies
• What tools, processes, and ideal customer definitions are required before you hire your first SDR
• Which SaaS business models make the most sense to use SDRs in the sales process
• Which outbound lead development approaches are productive in generating qualified discussions
• What compensation ranges are typical for SDRs this year
• How to think about SDR business goals and targets
• If you should hire one SDR or a sales manager-doer as your first sale hire
• When should founders hire "full-cycle" salespeople instead of a lead gen-only SDR

Learn more at practicalfounders.com.

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 raising $63 million in venture funding in the early 2000s. He brought in a CEO to run the company before it was sold to Motorola. 

Dave joined the large tech private equity firm TPG and directed many investments there before creating his own small venture capital firm and making several investments in the 2000s. Dave started to become disenchanted with the "Get Big Fast" of the venture capital approach. He talked to several founders who were growing businesses without any outside funding and who were building better businesses with better cultures and better outcomes with no intent to ever sell their companies.

In 2013, Dave started the Tugboat Institute, a membership organization that brings together Evergreen® CEOs across industry sectors to share best practices and unique insights, and to develop trusted bonds for their respective Evergreen paths. Evergreen leaders are seasoned entrepreneurs, CEOs, and presidents with the vision, creativity, resourcefulness, patience, and grit to build and scale a business that will stay private indefinitely.

Learn more at practicalfounders.com. 

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 their own business and differentiate their services. After using and improving their software for over 10 years, the family owners of Windermere spun out the software as a new company called MoxiWorks. They hired experienced tech entrepreneur and marketer York Baur to lead the new MoxiWorks business as CEO in 2012.

After rewriting the software from scratch, they started selling their solution to other large brokers in the US. They grew steadily and expanded their product platform and their team. MoxiWorks is now a leading platform system for large residential real estate brokerages, serving over 800 brokerages and 400,000 agents nationwide, which account for more than 20% of transactions in the U.S. 

MoxiWorks started as an internal technology investment at Windermere Real Estate, but their early growth years were funded by the Windermere owners and customer sales. In 2019, Vector Capital made a major investment to help MoxiWorks expand beyond its current $50 million in revenue and 300 employees.

See the full-text transcript and show notes at practicalfounders.com.