Practical Founders Podcast

Tune into the Practical Founders Podcast with host Greg Head for weekly in-depth interviews with SaaS founders who have built valuable software companies without big VC funding.

#181: Why Systems (with AI) Scale Better Than People in SaaS - Jordon Comstock 01/30/2026

#181: Why Systems (with AI) Scale Better Than People in SaaS - Jordon Comstock 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 Podcast Sponsor – Designli This podcast is sponsored by , 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 . The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39917680

#180: AI Is Not Killing Vertical SaaS - It’s Practical Leverage - Deepak Sindwani 01/23/2026

#180: AI Is Not Killing Vertical SaaS - It’s Practical Leverage - Deepak Sindwani Deepak Sindwani is Managing Partner at , 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 Podcast Sponsor – Lighter Capital This podcast is sponsored by . 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 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 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39820715

#179: Don’t Sell Your SaaS Yet: Hire a CEO and Get Your Life Back - Tighe Burke 01/16/2026

#179: Don’t Sell Your SaaS Yet: Hire a CEO and Get Your Life Back - Tighe Burke Tighe Burke is the founder of , a boutique executive search firm that helps SaaS founders replace themselves as CEO without selling their companies. After years in large executive recruiting firms, Tighe built a practice focused on founders who want their business to keep growing while they step back from day-to-day leadership. Tighe works with profitable software companies typically in the $5M–$50M revenue range, helping founders hire experienced and scrappy operators who have already scaled businesses through the next phase. His team has completed more than 75 executive searches, often placing CEOs who take full P&L ownership while founders move into chairman, product, or portfolio roles. In this episode, we dig into when hiring a CEO makes sense, how compensation and incentives really work, and what founders must let go of for this transition to succeed. Tighe shares practical warning signs, real compensation structures, and why this “third door” can create more value and freedom than selling too early. Key Takeaways Founder Readiness Matters — This only works when founders clearly know what they want their life and role to become next. $5M+ Reality Check — Most companies need real profitability to afford a strong CEO with authority and incentives. Operators Are Different — The best CEOs have already scaled similar businesses and don’t need to learn on your dime. Let Go Or Don’t Hire — Founders who keep control undermine the hire and drive away the right operators. Comp Isn’t Just Equity — Profit sharing, bonuses, and transaction payouts often work better than stock alone. Shadow Period Is Normal — The first few months require intentional transition, not instant disappearance by founders. Value Can Multiply — Hiring the right CEO can grow valuation faster than selling too early ever would. Quote from Tighe Burke, Founder of SRCH Partners “There are three doors as a founder entrepreneur. Door #1is keep running your business. Maybe you love your business. Door #2 is to exit the business and sell your company whenever you either get a good multiple, or the time is right, or a good buyer. “ “Door #3 is where we come in. Hopefully, your business cash generating asset for you. There are a lot of founders who think of their business that way. Some particularly people who like start their own company, it's their baby, it defines who they are. That's great. But if for any reason you're feeling angst or like you think someone can get past 10 million when you've really struggled there, that's probably true. “Let's bring in somebody else, an operator, a big O operator to run the business, to own the P &L, to make strategic decisions, to hire, to fire, to do all the things that you probably don't really like anymore. “You don't have to sell the business. You can actually get a bigger multiple later on by having a strong management team in place if that is something you choose. And you get your life back. can be with your family. You can start another business. You can advise, invest, kind of do whatever you want.” Links Podcast Sponsor – Designli This podcast is sponsored by , 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 . The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39736655

#178: Approaching $20 Million ARR with 99% Annual Retention - Dan MacDonald 01/09/2026

#178: Approaching $20 Million ARR with 99% Annual Retention - Dan MacDonald Dan MacDonald is the founder and CEO of , based in Edmonton, Canada. He didn’t start in safety or software—he came from retail and leadership training before an unexpected pivot led him into online safety systems. That shift eventually became a long-term bet on a “un-sexy” problem that companies can’t ignore. Today, BIS Safety serves more than 2.5 million users across high-risk industries like construction, mining, transportation, and energy. The company generates roughly $25M CAD in annual revenue, employs about 200 people globally, and runs one of the stickiest SaaS platforms you’ll find—with less than 1% annual logo churn. After nearly 20 years of bootstrapped growth, Dan is beginning a staged exit, starting with a minority secondary sale and planning a control transaction in a few years. Along the way, he shares hard-earned lessons about product obsession, compounding customer retention, and why steady execution beats hype. Key Takeaways Extreme Retention Matters — Less than 1% annual churn created compounding growth without aggressive sales spending. Product Over Sales — BIS focused on usability and depth first, letting word-of-mouth drive most early growth. Customer-Funded Start — Early customers paid to build the first LMS, avoiding dilution and premature fundraising. Long Bootstrap Reality — The first decade involved no salary, deep personal risk, and constant financial pressure. Enterprise Power, End User Simplicity — Power users get depth, while users see an interface designed to feel effortless. Quote from Dan MacDonald, Founder and CEO of BIS Safety Software “So at that time when I started the business, there was an awakening kind of moment of realization. It hit me big. I'm reading hundreds of business books and reading about Bill Hewlett, Dave Packard, Sam Walton, and many others. “I'm listening to the things they're saying, the ways they're thinking, And all I'm thinking is, my God, they think like me, they're just like me, they're normal people, they're just like me. And that was kind of the first awakening realization to say, they're not superhuman! That gave me the confidence to build the business and believe in the future. I never thought there's a pot of gold at the end of the rainbow it was never about the money. It was just some burning thing inside me that just I need to do this.I was just driven to do to do this. I felt like it was just this is what I'm meant to do.” Links Podcast Sponsor – Lighter Capital This podcast is sponsored by . 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 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 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39655320

#177: Building Multi-product Vertical SaaS With a Tiny Team - Robin Eissler 01/02/2026

#177: Building Multi-product Vertical SaaS With a Tiny Team - Robin Eissler Robin Eissler is the founder and CEO of , a vertical SaaS platform built for high school booster clubs. After selling her prior business as a private jet broker, Robin volunteered to run a local booster club and discovered a messy problem run with spreadsheets, emails, and manual accounting. She decided to build a single system that could actually handle it. BoosterHub now serves nearly 600 booster programs, representing over 100,000 users. With just two full-time employees and a small dev team, the company processes more than $40M in transactions across payments, fundraising, merchandise sales, and accounting. Annual contract value typically runs $1,500–$2,000 per customer, with strong retention and expanding usage. Still independently-owned and bootstrapped, BoosterHub is approaching $1M ARR and profitability. Robin shares lessons on building complex software with a tiny team, selling to volunteer buyers, surviving seasonal revenue swings, and why slow, compounding growth can create durable SaaS businesses without venture capital. Key Takeaways Tiny Teams Work - Two employees plus contractors can build serious SaaS with focus, systems, and modern tooling. Sticky Beats Big - Hundreds of small customers compound more reliably than a handful of enterprise deals. Seasonality Is Real Education-adjacent - SaaS must survive cash spikes and winter slowdowns without panic. Founder-Led Marketing - Consistent content from the founder still drives inbound growth in niche markets. All-In-One Wins in Verticals - Being the system of record makes churn low and customer value expand naturally over time. Quote from Robin Eissler, Founder and CEO of BoosterHub “The numbers are much better than what we projected. so we're starting to see that compounding effect is really what's happening is there's just enough users and enough people in the system that they're using more of the add-on products and we're processing more volume. “So it's starting to have that compounding effect. And so I really just admitted to myself this month, like, I think we're seeing it. “I think we're finally seeing it. I feel like, OK, maybe for me, it's almost that I can exhale. I've been holding my breath for four years, so maybe I can breathe.” Links Podcast Sponsor – Full Scale This podcast is sponsored by , one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39580740

#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head 12/26/2025

#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head As the year winds down, I want to share an end-of-year message for practical SaaS founders who want to make better progress in 2026. Based on my recent conversations with more than 40 CEOs in my Practical Founders peer groups, it’s clear that growth rates alone don’t define whether it was a “good” year. Founders experienced very different outcomes—and very different feelings about them. In this episode, I walk through five practical questions I believe founders should ask as they look ahead to 2026 (or their next quarter). These questions focus on whether you’re working on the right hard things, what you’re deliberately changing next, what help you actually need, whether you have enough cushion in the business, and the story you’re telling yourself and your team about progress. This isn’t about templates, quick-fixes, hype, or perfect planning. It’s about making steady progress on the hardest, most important things in your business—while staying independent and resilient. Success isn’t final and failure isn’t fatal. What matters is whether you keep going—and keep making progress. If you’re still here, still building, still learning—you’re doing something right. I respect practical founders who choose independence, solve real problems, and do hard things year after year. Key Takeaways Progress Over Growth Rates - What matters is whether you moved the hardest, most important parts of your business. Focus Is a Force Multiplier - Trying many things without concentration is why most initiatives stall. Companies Mirror Their Founders - The company’s strengths and weaknesses often mirror the founder’s. Cushion Creates Resilience - Cash, energy, and upsides protect businesses when headwinds inevitably appear. You Make It Up - How you frame last year’s results shapes decisions, morale, and alignment. Quote from Greg Head, founder of Practical Founders “Everybody's doing really hard things who are practical startup founders. I know you are too. The question isn't about what the perfect growth rate or planning process is for you right now. The question is, are you lined up to actually do enough of the most important hard things in your business next year? Are you really set up to make the kind of progress you want along the bigger vision you have for the company? There are all kinds of ways to do it. You can go fast or slow, or it could be an invest year, a rebuild year, or a steady year. You can choose your growth rate, your profitability, and all of that. “You get to do it your way. You've bought your independence, or you are paying for it the hard way. There’s no one right way to do all of this, if you're making big progress and getting better every year in the eyes of your customers, employees, and the owners.” Links Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by , 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 The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39531570

#175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh 12/19/2025

#175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh Dave Hersh, co-founder and former CEO of Jive Software, shares the real story behind bootstrapping Jive to $12M in revenue before raising venture capital and scaling aggressively. He explains how fear, comparison, and the pressure to “go big” drove him to abandon his profitable core business and pursue a new upmarket strategy that ultimately cost the company its soul. After growing to $60 million, Jive eventually went public, but not without internal strain, personal turmoil, and ultimately the realization that the company had drifted away from what made it successful. Dave discusses how overexpansion, premature scaling, hiring missteps, and market-chasing derail both VC-backed and bootstrapped companies—along with the psychological patterns founders rarely acknowledge. He shares lessons from his book “” on why most stuck companies don’t need a new strategy—they need a wiser founder who understands their inner operating system and is willing to grow alongside the business. Today Dave coaches founders, writes about the emotional foundations of leadership, and acquires underperforming SaaS companies to “refound” them with more clarity, connection, and human-first strategy. Key Takeaways Founder Psychology Matters — Most stuck companies trace back to subconscious patterns, not strategy failures, and founders must address these to grow. Premature Scaling Kills — Expanding markets or teams too quickly dilutes the core and creates complexity most companies cannot absorb. Core Before Expansion — Winning in a beachhead and protecting the core creates more durable growth than chasing adjacent market too early. Better Growth Pace — Sustainable companies grow at the pace the market allows; forced hypergrowth often destabilizes otherwise healthy businesses. Quote from Dave Hersh, Co-founder and Former CEO of Jive Software ”I realized that 90% of stuck companies and failed companies are not the reasons that we say they failed. Like they didn't have product market fit or they ran out of cash or the founders didn't get along. It's the psychology underneath. If you actually look at the source of those problems, It was these very consistent psychological patterns that founders run into. “So hero complex, warrior, imposter syndrome, over identification with the company. It was all of these things that I kept seeing over and over again that led to the decisions that got them stuck. And so, yes, while it's true, they got out competed. Why did they go after the big market? What led them to do that? Why did they try to compete against these companies they were competing against? ”And then you start to tap into what's really going on and you see: They're trying to earn validation. They are trying to get redeemed as an entrepreneur. They're trying to live up to their parents, their older sibling, their peer group. And it was that desire that led to them trying to go after this big market and raising too much money that got them stuck. And so I like to work with the source material, which is, Why did you do that?” Links Podcast Sponsor – Fraction This podcast is sponsored by . 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 You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39448690

#174: Plateaus, Pivots, and Staying Profitable: Solving Practical SaaS Puzzles - Josh Ho 12/12/2025

#174: Plateaus, Pivots, and Staying Profitable: Solving Practical SaaS Puzzles - Josh Ho Josh Ho is the Founder and CEO of Referral Rock, a bootstrapped referral marketing platform serving SMBs that rely on multi-step, relationship-driven sales. Starting in 2015 as a solo developer consulting on the side, Josh built the first version himself, validated demand quickly, and landed early customers by doing demos and hands-on support. Referral Rock has grown to roughly 500 customers, 20 team members, and about $3M in annual revenue. The company scaled through strong inbound SEO, founder-led sales, and a high-touch onboarding model for B2B businesses that value referrals. Over the years, the product expanded too broadly, creating UX and complexity challenges that later required a deliberate refocusing on core use cases. Today, Referral Rock is profitable, founder-owned, and steady at its current revenue plateau as Josh rethinks pricing, packaging, product simplicity, and ICP focus. He shares practical lessons on avoiding over-complexity, hiring from what you’ve already figured out, returning to first principles, and treating plateaus as puzzles to solve rather than signs of failure. Key Takeaways Charge Early, Not Late – His first startup delayed monetization; Referral Rock asked for payment within days of launching an MVP. Pricing For Segments– Good-better-best failed for SMBs with wildly different referral economics; switching to two specific lanes solved misalignment. Do the Job First – Hiring worked only after Josh personally figured out support, sales, or marketing enough to define the role clearly. Plateaus Aren’t Failure – Post-COVID shifts and SEO changes slowed growth, but Josh treats plateaus as system puzzles, not existential threats. Profit Equals Freedom – With no investors and steady profitability, he optimizes for enjoyable work, long-term optionality, and building at his own pace. Quote from Josh Ho, Founder and CEO of Referral Rock “For me, a plateau or a pivot is a puzzle to be solved. Any time you try to build something, you hope to just keep hitting accelerators and different serendipitously find those things. But I've learned through my life, the most part, there are things that work only for a certain duration, right. “For me, it comes back to how I think about the business and. my innate goals for the business which, are different from most founders. When I’m talking to another founder is, they'll ask me what my exit strategy is. And my answer is usually, Well, I don't really have one. That's not how I think about the business. It's a very clear. “I enjoy my work and that's my North Star. Am I having fun? Do I enjoy this work? And I also continuously reinvent myself and my role to fit those changes.. There might be a job I had to do that I don’t enjoy, but then I'll do that until it's no longer like the limiting step and then hire someone to backfill for myself.” Links Podcast Sponsor – Designli This podcast is sponsored by , 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 . The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39363985

#173: From COVID Boom to Bootstrap Mode: Hubilo’s Refounder Story - Shailesh Hegde 12/05/2025

#173: From COVID Boom to Bootstrap Mode: Hubilo’s Refounder Story - Shailesh Hegde Shailesh Hegde is the CEO of , a Bangalore-based webinar software company that initially started during COVID as virtual events tech and raised $150M in VC funding before the market shifted. Originally joining as head of product, he stepped into the CEO role during a chaotic downturn and led the company through a full strategic reset after returning all the remaining capital to investors. When the virtual events boom collapsed, Shailesh and the team rebuilt Hubilo into a mid-market webinar platform serving B2B marketing teams. They shifted from large in-person event organizers to marketers running frequent webinars, emphasizing differentiated AI-driven content repurposing. Hubilo stabilized revenue, rebuilt its GTM motion, and reached a 50/50 split between new webinar revenue and legacy customers. Earlier this year, Hubilo was acquired by BrandLive, a U.S. enterprise video platform seeking a complementary webinar product. About 80% of Hubilo’s team moved over, and Shailesh now leads product integration and customer continuity during the transition. He shares hard lessons on pivots, returning capital, leading through uncertainty, and executing a practical exit when the original VC-scale vision is no longer realistic. Key Takeaways Refounder Mindset – Shailesh stepped into the CEO role and reframed the mission from hypergrowth to survival, focus, and a practical exit. New ICP Reality – Moving from event organizers to B2B marketers required a complete repositioning and GTM rebuild that took longer than expected. AI as Differentiator – Hubilo used AI-generated content and repurposing tools to stand out in a crowded webinar category with entrenched incumbents. Practical GTM – LinkedIn thought leadership, SEO content, and product-led demos outperformed outbound or expensive Google ads in this competitive space. Strategic Fit Wins – BrandLive acquired Hubilo for complementary capabilities, product acceleration, and access to a strong India-based engineering team. Quote from Shailesh Hegde, CEO of Hubilo “Now that I just sold our company, I’m thinking about what’s next for me. It comes down to, Will I be able to find a viable problem that people are willing to pay for and will I be able to use sort of all of this experience that I have in order to solve it really well and kick off a company off the ground? “Now is probably the best time to start a company where there's so much action, there's so much happening in AI, and it's super exciting to be in this space. It's also a great time to not have like revenue pressure on your shoulders and just think out loud, have open conversations and just be free, before you really dive in and choose a focus. “The same types of business pressures will come back as you start a company. But now is a great time to just help with transition, make sure the team is good, but at the same time, start thinking about the types of problems I want to solve in the future with a new startup.” Links Podcast Sponsor – Fraction This podcast is sponsored by . 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 You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39262760

#172: Why Long-Term Bootstrapping Still Works in Event Mgt. SaaS - Raju Patel 11/28/2025

#172: Why Long-Term Bootstrapping Still Works in Event Mgt. SaaS - Raju Patel Raju Patel founded over 25 years ago after building a speaker portal for a magazine company and realizing he had a repeatable software product. What began as a one-man shop in suburban Chicago evolved into a robust event-management platform serving associations that needed complex, multi-module functionality. His business grew steadily as he delivered registration, booth management, speaker portals, and onsite systems for demanding event teams. Today eShow has 125 employees, more than 14 integrated modules, and supports hundreds of events each year for 300+ customers, including large association conferences with tens of thousands of attendees. The company has always been profitable, self-funded, and built through careful reinvestment, steady hiring, and deep product expansion. Raju rebuilt the platform multiple times, including a shift to a modern stack. Still independent with over $10 million in revenues, Raju is now building a VP-level leadership team, exploring practical growth capital, and planning a hybrid event model that blends in-person and virtual experiences. His story highlights long-term passion, practical growth, and a deliberate shift from hands-on founder to capable CEO after decades in the game. Key Takeaways Deep Domain Focus – Serving the most complex association events created defensible differentiation. Slow, Steady Compounding – Year-over-year growth came from incremental improvements, not big bet. Passion Over Money – Raju built for love of the work, not an exit, which sustained him through decades of change. Multiple Rewrites Needed – Long-term SaaS requires full platform rebuilds, and Raju completed two with a third underway on a modern stack. Late-Stage Professionalization – Hiring VPs, defining ICPs, and strengthening leadership came only after passing the $10M threshold. Quote from Raju Patel, founder of eShow “Looking back after 20 years running this as a small business in software, think I would have figured out how to pull a little bit more money out. It would have given me a better peace of mind." "I wouldn't have even known how to spend if I pulled a million out back then, it would have been wasted. I was very frugal and investing in my business every year." "But now I could figure out how to spend a million dollars, on savings and other personal spending that would be meaningful. It would be liberating. I deserve it, so I'm going to spend a little bit more, not be frugal. I can be frugal in my business and in my personal life not be so frugal!” Links Podcast Sponsor – Full Scale This podcast is sponsored by , one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39188175

#171: Lessons from a 9-Year Bootstrap Journey to a Private Equity Exit - Dharshan Rangegowda 11/21/2025

#171: Lessons from a 9-Year Bootstrap Journey to a Private Equity Exit - Dharshan Rangegowda Dharshan Rangegowda, founder of , 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 Podcast Sponsor – Designli This podcast is sponsored by , 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 . The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39104540

#170: Why Most SaaS Acquirers Still Want Profitable Growth in 2025 - Gaurav Bhasin 11/14/2025

#170: Why Most SaaS Acquirers Still Want Profitable Growth in 2025 - Gaurav Bhasin Gaurav Bhasin is the founder and managing director of , 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 Podcast Sponsor – Fraction This podcast is sponsored by . 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 You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/39015885

#169: Practical Pivot and Relaunch Created Profitable 200% Growth - Natalie Barbu 11/07/2025

#169: Practical Pivot and Relaunch Created Profitable 200% Growth - Natalie Barbu Natalie Barbu is the founder and CEO of , 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 Use this 10% Discount Code for Rella - practical Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by , 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 The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/38932910

#168: These Three Superpowers Set Practical SaaS Founders Apart - Greg Head 10/31/2025

#168: These Three Superpowers Set Practical SaaS Founders Apart - Greg Head 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 Podcast Sponsor – Designli This podcast is sponsored by , 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 . The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/38839890

#167: Practical Founders Brought in CEO to Scale Their Company - Darryl Pahl 10/24/2025

#167: Practical Founders Brought in CEO to Scale Their Company - Darryl Pahl Darryl Pahl is the co-founder of , 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 Podcast Sponsor – Fraction This podcast is sponsored by . 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 You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/38750715

#166: How Practical SaaS Founders Can Compete in the AI Economy - Vincent Serpico 10/17/2025

#166: How Practical SaaS Founders Can Compete in the AI Economy - Vincent Serpico , veteran CTO and founder of Founders Workshop, is on the front lines of the AI revolution in 2025, reshaping software development and business operations. With more than 30 years of experience building software apps, Vincent is now dedicating himself full-time to AI coaching and workshops for teams and companies to create high-leverage impact quickly. Vincent shares how practical SaaS founders are leveraging agents, vibe coding, and tools like OpenAI’s Agent Kit to multiply output without adding headcount. He sees the shift from SEO to GEO, the rise of ChatGPT apps, and why domain expertise is the ultimate competitive moat for SaaS founders navigating this new economy. Now leading Vincent describes how entire applications can be built without writing code, using natural language and iterative management. He stresses that daily AI use, human-in-the-loop workflows, and focusing on domain-driven innovation will give practical founders the edge in this seismic shift. Key Takeaways Agents As Labor – AI agents perform multi-step workflows like employees, delivering productivity gains with human-in-the-loop oversight. Domain Expertise Moat – Deep customer and industry knowledge matters more than raw coding speed in the AI economy. Vibe Coding Skills – Non-coders can now build apps with natural language prompts, managing AI like junior employees. Practical AI Adoption – Founders should start with small use cases, building workflows before tackling complex projects. Great Arbitrage Period – Founders who embrace AI now gain massive leverage over competitors who resist change. This Interview Is Perfect For SaaS founders ready to apply AI beyond experiments Product leaders exploring AI-driven workflows Developers curious about vibe coding and agentic design Founders building lean, AI-powered teams Quote from Vincent Serpico, founder of Serpico.ai “If you're not an expert in something, AI will probably make you two to three times better than you currently are. But if you are an expert in something, AI will make you 10x better. “If you're already a domain expert, using AI will make you 10x better. Those are the ones that you should be hiring and paying outpaced salaries to, and build your tiny team—domain experts who are great at AI. “If I want to use AI in real estate, I could do it, but a guy who's been a real estate agent for 30 years will do much better if he understands AI skills like how to prompt and context engineer. “So we’ll see hiring domain experts and paying them outsized salaries because they're utilizing AI and producing five, six times more than they could without it.” Links Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by , 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 The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/38600255

#165: How to Enjoy Being the CEO as Your SaaS Business Grows Bigger - Brett Gilliland 10/10/2025

#165: How to Enjoy Being the CEO as Your SaaS Business Grows Bigger - Brett Gilliland Brett Gilliland, founder of , joins Greg to discuss how they help ambitious founders navigate the tough leadership journey from $1M to $10M in revenue. Brett shares how co-creating a clear, practical Purpose, Values, and Mission form the foundation of scalable organizations. He explains why moving from founder-led chaos to aligned leadership teams is the critical step that separates $1M experiments from $10M companies. With clear meeting rhythms, disciplined execution, and strong hiring practices, Elite Entrepreneurs has helped hundreds of founders become happy CEOs and build companies that run without constant founder involvement. Brett reveals the personal transformation required for founders to evolve into true CEOs who can enjoy their business more as it grows. You can reduce chaos, scale your teams, and rediscover the fun of running your business once you shift focus from “I” to “we.” Key Takeaways Growth Brings Freedom: Founders who learn let go in the right way often rediscover fun, profit, and time. Leadership Teams Required: Scaling past $3M–$10M depends on building a capable senior leadership team. Meeting Rhythms Drive Scale: Annual, quarterly, monthly, and weekly cadences keep teams aligned. CEO Core Roles: Set the vision, build the team, and secure resources—everything else gets delegated. Hiring as Marketing: Culture-fueled job postings act like a “bat signal” for the right candidates. This Interview Is Perfect For SaaS founders at $1–5M in ARR Business owners feeling “stuck” at their current stage CEOs ready to build their first real leadership team Entrepreneurs who want growth and a life Quote from Brett Gilliland, founder of Elite Entrepreneurs “All of us get stuck in some way. We know there's a better way. We see other people figuring it out. I should be able to do this, we say, but we just didn't know what to do. "You have to do work on your business in a deliberate way. And those who do the work consistently make progress. We help them lay out the path from $1 to 10 million. Here are the things that you do. It's proven, it's practical. “Whoever has been consistent with it, quarter after quarter, month after month, week after week, doing the things that we're talking about, they start stacking wins. “Then all of a sudden, 18, 24 months later, we're at a place where we've tripled in revenue, we've doubled in team, it's fun, I've got some time back in my life. It does take time, but it's totally doable. I've seen it over and over and over again. Links Podcast Sponsor – Designli This podcast is sponsored by , 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 . The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/38519840

#164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta 10/03/2025

#164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta Praveen Ghanta, founder of and former CEO of HiddenLevers, shares how he turned his experience scaling a bootstrapped SaaS company into a fast-growing fractional talent marketplace. After HiddenLevers reached $8M in ARR and sold for over $100M, he realized that senior fractional engineers were the secret to delivering efficiently without expensive full-time hires. Fraction now serves over 100 SaaS clients with a vetted pool of 500 senior U.S.-based engineers and CTOs. Typical engagements run 10–30 hours a week, helping founders tackle scaling challenges in vertical SaaS, AI engineering, DevOps, and legacy system conversions. The company has reached $10M ARR in just three years while keeping half its own team fractional. Praveen explains how clients use Fraction to save costs, speed development, and even prepare for M&A due diligence with fractional CTOs. He also highlights how AI has boosted senior developer productivity by 4x, why U.S.-only context matters, and how fractional-to-full-time hiring often becomes a win-win path. This interview is perfect for SaaS founders at $1M–10M ARR, hitting scaling issues, vertical SaaS leaders needing senior engineers without VC funding, and founders considering AI-powered product features and engineering talent. Key Takeaways Fractional Individual Contributors: Not just execs—senior engineers deliver hands-on code, marketing, and DevOps part-time. AI Productivity Boost: Senior developers using AI tools are delivering 2–4x more than peers without them. Cost Advantage: Starting at $5K/month, founders access senior dev talent without $200K+ full-time salaries. Best ICP Fit: Vertical SaaS companies at $1–10M ARR facing scaling issues or legacy migrations. Developer Productivity: Fraction leveraged its experience with over 100 clients to build tool that manages fractional talent and delivers results even more efficiently. This Interview Is Perfect For SaaS founders stuck at scaling challenges without a budget for big teams Bootstrappers and practical founders looking for senior engineering firepower Founders facing legacy code, scaling issues, or AI feature rollouts Non-technical founders struggling to manage offshore or junior dev teams Quote from Praveen Ghanta, founder of Fraction “There are a lot of very experienced engineers who get into a senior developer role, but if they’re not going to become the manager of the team, there's not a really good and obvious career path for them. “They start to get bored because they know their job inside and out and it's relatively easy for them to keep delivering. “So working on a startup on the side is actually a way for both for them to sort of enrich their career and see new things and have that creative satisfaction, but at the same time, not take the risk. There are plenty of folks that want to be full-time at the startup, but there's risk in being at a startup.” Links Podcast Sponsor – Fraction This podcast is sponsored by . 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 You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/38435360

#163: Anthony Pierri & Rob Kaminski of Fletch: Why All SaaS Founders Struggle with Positioning 09/26/2025

#163: Anthony Pierri & Rob Kaminski of Fletch: Why All SaaS Founders Struggle with Positioning Anthony Pierri and Rob Kaminski are the co-founders of , a positioning strategy firm for B2B SaaS companies. They started Fletch after observing that most founders often confuse positioning with copywriting and marketing, and built their business by helping SaaS leaders make the tough, strategic choices about who they serve and how they win. Over the last three years, Anthony and Rob have collaborated with over 400 SaaS companies, ranging from early-stage startups to rapidly growing companies. Fletch helps founders and B2B SaaS leaders clarify their positioning, sharpen their messaging, and translate strategy into effective homepage design. In our practical discussion, they help founders see that positioning is a business strategy, not copywriting, which forces clarity and tradeoffs to improve execution. They share why founders must (eventually) choose one clear path to scale efficiently and why bootstrapped SaaS leaders often make sharper bets than VC-backed peers. Key Takeaways Positioning = Strategy: Positioning is a founder/CEO choice, not copywriting or branding. Almost Universal Problem: Most B2B SaaS founders struggle with positioning clarity. Anchors Drive Focus: Use category, use case, or alternative as clear positioning anchors. Bootstrappers Move Faster: Limited capital forces clarity that VC-backed companies delay. Execution Takes Time: Positioning decisions are quick, but discipline drives results. Homepage Test: Your homepage clearly reveals whether positioning is working or not. This Interview Is Perfect For SaaS founders stuck at $1M–$10M ARR growth plateaus Bootstrapped operators needing sharper messaging to scale Founders unclear about marketing vs positioning strategy B2B SaaS CEOs rethinking go-to-market focus Quote from Dave Yuan, founder of Tidemark Capital “There is a difference between bootstrappers and VC-funded startup founders in successfully positioning their startups. Bootstrappers are willing to see a narrow opportunity and tackle it with focus, because almost every market is big enough to sustain a $10 million company. “I don't care how narrow you get, the world's a big place. So even with a hyper-focused, verticalized niche, or use case play, there's plenty of money if you do it well and that's very appealing to bootstrappers. “Most VC-funded founders don’t focus as well, which creates problems. But the founders who truly understand positioning and the idea that it can evolve over time, whether they're venture backed or not, they start with a very narrow practice to start and succeed as a leader. “ Links Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by , 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 The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/38348165

#162: Practical Investor - What’s Working Now in AI-Driven SaaS Growth - Dave Yuan 09/19/2025

#162: Practical Investor - What’s Working Now in AI-Driven SaaS Growth - Dave Yuan Dave Yuan is the founder of , an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become “control points” in their markets and grow very big. Dave and Tidemark have invested in successful vertical software companies like Toast, ServiceTitan, Jane, and CCC. Tidemark hosts its annual featuring experienced speakers for hundreds of vertical SaaS founders, on November 5, 2025. In this episode, we discuss the practical opportunities and risks of AI as it is currently developing in 2025 for vertical SaaS companies. Dave explains several powerful examples of how AI is being used in his portfolio companies and the new strategic questions that are being discussed. Dave also shares: Why software companies are getting real results with AI and are not waiting for the AI revolution--it’s here now. How AI-powered “systems of action” have undue influence with important users and can potentially displace entrenched systems of record software. How fast-growing practical software company grow efficiently with well-timed product, channel, and regional expansion. Quote from Dave Yuan, founder of Tidemark Capital “There are a handful of examples where software companies with AI-powered solutions are getting two to five times what they got on a software seat with new outcome-based pricing. They are providing real hard to ROI that's measurable, oftentimes associated with revenue. “And arguably, they're only getting started because the outcomes that they're measuring are relatively low value and they can increase the value of the outcomes and price accordingly. “To capture that value, it depends on competition. Because you can add a lot of value to your customers, but you can only charge for that value unless there's not a lot of competition vying for the same thing.“ Links Podcast Sponsor – Designli This podcast is sponsored by , 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 . The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at 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 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 . /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/38261100

#161: When Co-Founders Need Relationship Therapy - Dr. Matthew Jones 09/12/2025

#161: When Co-Founders Need Relationship Therapy - Dr. Matthew Jones Dr. Matthew Jones is a licensed clinical psychologist who specializes in working with co-founders to help manage critical conflicts that threaten their success. He is the author of the book, "The Cofounder Effect: How to Diagnose, Fix, and Scale Healthy Communication for Startup Success." Matt has worked with hundreds of bootstrapped and VC-funded co-founder teams to help them repair and manage their relationships in the context of their growing business. In this episode, we discuss a wide range of co-founder relationship topics, including: Why co-founder alignment sets the floor and ceiling for entire company culture and employee performance. How most co-founder conflicts aren't about surface issues but deeper psychological needs for recognition and power. Why research shows companies founded by friends are more unstable than those started by strangers. The three communication languages of cofounders: operational (business), psychological (feelings), and archetypal (the vibe). Quote from Dr. Matthew Jones, a clinical psychologist “And those differences can start off and be quite positive. If we can manage that tension effectively. That's the magic of co-founders, right? Is the complementary skills and ways of operating that allows you to land somewhere even more effective than you could have individually. “But those same differences that give you that magic sauce also can be sources of friction, like an arthritic knee that just aches every now and then, and sometimes gets worse and worse, right? And so that's where the tensions really have to be managed. And so that's why I advocate for making those differences as conscious and explicit as possible.” Links The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/38174845

#160: CPG Founder Turned Failure Into a Profitable SaaS Business - Yuval Selik 09/05/2025

#160: CPG Founder Turned Failure Into a Profitable SaaS Business - Yuval Selik Yuval Selik is co-founder and CEO of , a software platform and managed service for Consumer Packaged Goods (CPG) brands to manage their trade promotions and field marketing activities. Yuval is a former CPG founder who encountered the expensive, complex, and crucial process of managing trade promotions with stores and distributors. Promomash launched in 2015 to serve mid-sized CPG companies that don’t have custom software and their own teams to manage promotion spend and budget compliance with retailers. With 125 employees, they now serve over 500 customers with their software and optional analysts who can perform complex sell-through reconciliation and spend analysis. Yuval and his co-founder raised under $1 million from angel investors to get started, and the company is now profitable and growing steadily. Yuval also hosts The 7 Hats Podcast, which helps entrepreneurs master the seven key areas of their lives, ensuring both success and fulfillment. Quote from Yuval Selik, the founder and CEO of Promomash “That's really the reason why we did not raise funds from big investors, because I don't want to have the pressures of somebody on my board telling me that I have to grow 50%, 80%, or 100% year over year. “Sometimes you need to pull back in order to fix your product. Sometimes you need to push forward and step on the gas a little bit. But that decision needs to be my decision, not a VC investor’s decision. “Others in our market that raised big VC funding, in our competitive landscape. They are not run by their founders; they're run by their investors” Links The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/38080330

#159: Co-Parenting App Reaches $10M ARR Through Pure Bootstrap Growth - Vince Mayfield 08/29/2025

#159: Co-Parenting App Reaches $10M ARR Through Pure Bootstrap Growth - Vince Mayfield Vince Mayfield is cofounder and CEO of , a co-parenting app for communication and coordination used by divorced parents raising children. Cofounder Stephen Nixon was a lawyer with family cases who recognized the need for a secure, unalterable communication record to improve co-parenting and family harmony. He pitched a development company owned by Vince and Louis Erickson to build the first app. They came together to cofound TalkingParents in 2012. Stephen worked with judges, courts, and lawyers to build awareness and get their first customers. The app records and stores all communications between co-parents, including chats, message, phone calls, and calendars. The company started growing and eventually became profitable as word spread, they charged more for the product, and the app improved. TalkingParents is now a profitable and growing company with well over $10 million in revenue, 65 employees, 100,000 paying customers, and 500,000 people using the app. They are self-funded with no outside funding. Quote from Vince Mayfield, cofounder and CEO of TalkingParents “The company you are when you have 5 million in revenue and maybe 40 people, it's not the same company you are when you've got 20 million in revenue and say 80 people. It's not. You've got to iterate and change. “And you've got to have the stamina for that. You've got to be willing to put in the effort and do that. Yeah, exactly. There's no shortcuts to this. “I love it when people tell me, I've got an idea and I'm going to start up and it's going to go viral overnight. And my first thought is bulls--t. It's not going to happen that way. “It's much harder than everybody thinks. You hear about the overnight success, but what you don't see is the 10-year grind that it took to get there. And the sacrifice and delayed gratification that goes along.” Links The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/37991250

#158: $33M Growth Equity After Friends/Family Funding to $10M ARR - Alan Miegel 08/22/2025

#158: $33M Growth Equity After Friends/Family Funding to $10M ARR - Alan Miegel Alan Miegel is co-founder and CEO of , a modern compensation management platform for larger companies to manage compensation datasets to set market-priced salary benchmarks. Alan and his cofounders started the company in 2019 with founder funding, then raised angel funding as convertible debt from his friends in the tech industry. They shipped their first “minimum sellable product” in 2020 and grew revenues steadily, doubling every year from $1M in 2022 to almost $10M in revenue in 2025. BetterComp now has over 80 employees and 200 customers. In July of 2025, BetterComp raised a combined $33 million in growth equity funding from Ten Coves Capital and venture debt from Silicon Valley Bank. Alan and his cofounders still own a majority of the company. Now they have more resources and support to build on what has worked so far, enabling them to grow even faster and become a market leader. Quote from Alan Miegel, cofounder and CEO of BetterComp “Early on I didn't pay myself anything. Then I paid myself enough just enough to max out my 401k contribution, with no taxable income. I made a promise to my founders, my co-founders that I was going to pay them before I paid myself. “I always paid my co-founders more than I made. That's still the case now. As the CEO, you think of it like you are the last one to get paid in this equation. You're not doing this to make money now, you're doing this to make money down the line. “And you ask a lot of other people to make sacrifices, you ask them to make less than what they're used to making, so you have to put them first. Because if they see you putting yourself first, they're not gonna think they're the most important thing in the business, which they are..” Links The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/37898850

#157: Seven Years In Survival Mode: A VC-funded Founder's Warning - Zvi Band 08/15/2025

#157: Seven Years In Survival Mode: A VC-funded Founder's Warning - Zvi Band Zvi Band is co-founder and former CEO of Contactually, which was CRM software for real estate and other relationship-oriented professionals. Contactually was founded in 2011 with initial funding and support from 500 Startups in Silicon Valley. In the next five years, they raised a total of $15.5 million from institutional VC investors. Contactually grew to about $10 million in revenue before growth stalled, and it became clear they couldn’t raise additional capital or grow big without funding. The company was sold in 2019 to Compass, a major real estate technology company and brokerage, to power their internal CRM platform. In this episode, Zvi candidly shares his personal experience with VC funding, their opportunities and challenges, and the strategic dilemmas they faced along the way. Zvi now owns and operates a bootstrapped contact management software business called . Quote from Zvi Band, co-founder and former CEO of Contactually “I realized I spent seven and a half years of my life in survival mode as a CEO with VC investors.. And at no point did I feel that like we were safe and things were fun, because the bank account was always trickling down a little bit. “We always had big growth goals. And we were always thinking about, How do we get through the next VC funding round? At no point did I realize and celebrate that, hey, we built something really awesome. “We could have chilled out once in a while or taken the team to Mexico for a week or something like that. But everything was around short term goals and what we need to do to get there that month.” Links The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/37811130

#156: Bootstrapper Built Vertical CRM to $10M ARR with Co-founder Dad - Shoanak (Sean) Mallapurkar 08/08/2025

#156: Bootstrapper Built Vertical CRM to $10M ARR with Co-founder Dad - Shoanak (Sean) Mallapurkar Shoanak (Sean) Mallapurkar is the founder and CEO of , a complete CRM and business management system for global staffing companies and recruiting agencies. He started the company in 2017 with his father, a technical expert who had experience as a senior executive in large staffing companies. Sean handled customer-facing jobs in sales, success, and product management, and his Dad managed engineering, finance, and marketing. They started in Pune, India, but both Sean and his father moved to Dubai in 2023 for lifestyle and tax benefits. Recruit CRM employs over 150 remote employees in India to serve thousands of customers in more than 100 countries. Recruit CRM revenues grew quickly to nearly $10 million ARR in 2025. Their product suite includes CRM, billing, applicant tracking, AI resume parsing, financial management, and more. The company is very profitable and growing steadily (Rule of 70) and the co-owners/co-founders have no intention of selling. They see a steady path to a $100 million revenue business as an independent company. Quote from Soanak (Sean) Mallapurkar, founder and CEO of Recruit CRM “The one thing that really worked for us was keeping costs extremely low and having over three years of capital runway. That wasn't millions of dollars for us. It was $100,000. And we didn't even spend it. We only spent about $80K before we started selling and got to breakeven. “When you have enough time,you can you can do more things, you can try more things, and make it happen. If you only have a year to succeed, you're screwed. Get through the really hard stuff and get to a million in revenue “Then resist the urge to raise capital until you are at a million dollars in revenue. Then ask yourself if you need it. If you can resist the urge to raise capital, a lot of opportunities open up to you. And it’s a very different financial outcome than having investors.” Links The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/37713210

#155: SaaS Founder's Crazy Ride: Boom, Bust, Strategic Sale - Jesse Burrell 08/01/2025

#155: SaaS Founder's Crazy Ride: Boom, Bust, Strategic Sale - Jesse Burrell Jesse Burrell is the CEO and co-founder of BatchService, now known as , a real-time data and API platform designed for prop-tech startups and enterprises requiring massive and current housing data. Jesse was a real estate investor who needed better data to target his marketing efforts. BatchService was launched in 2018 with data brokering and subsequently built additional tools and apps. BatchService grew rapidly to $35 million in revenue by 2022, but regulation changes and economic shifts contracted their core business, forcing them to make drastic cutbacks and pivots. They launched an enterprise data service with APIs for larger companies in 2021, which is now known as BatchData. In July 2025, BatchService sold its “B2C” software business, comprising two successful products — BatchLeads and BatchDialer — to PropStream for an undisclosed cash amount. Jesse and his co-founders retained the B2B BatchData enterprise data business, now with 30 employees. Quote from Jesse Burrell, cofounder and CEO of BatchService “I had a couple years where I was pinching myself with the amount of money I was taking home every month. It was pretty wild how fast we rose in the first years. So when things changed for us, the fall really hurt, especially when we felt invincible and every idea worked brilliantly for three years. “When things changed, we stayed pretty patient. We stayed pretty calm, but there was a lot of nights, weeks and months. I went home feeling like a failure and I don't think I was failing. I just think it was the conditions that we got put in. But it was really hard on me mentally. It was very, very tough to get punched so hard in the mouth with like a multitude of things in a short period of time. “You're not as good as you think you are when it's going good and when it's going bad. It's not typically as bad as you think you are. A lot of it has to do with conditions and things that happen that are out of your control. You're fighting that because you're an entrepreneur and you'll figure it out if you are just persistent and don’t give up.” Links The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/37615435

#154: 2nd-Generation CEO Modernizes Mom's Legacy Software Business - Brian Forbis 07/25/2025

#154: 2nd-Generation CEO Modernizes Mom's Legacy Software Business - Brian Forbis Brian Forbis is the CEO and president of Blood Bank Computer Systems, Inc. (BBCS), a business his mother created in the 1980s to serve the non-profit blood bank industry in the US. Brian started in sales, then transitioned to run development, and assumed the role of CEO in 2019 when he bought the company. rebuilt its entire mission-critical ERP software as a modern cloud solution over the last five years and is actively converting customers from legacy on-premise systems. With 40 employees and nearly $10 million in revenue, BBCS serves the blood banks that supply 20% of the blood products in the U.S. Their industry presents numerous unique challenges, including negotiating co-op pricing, complying with FDA regulations, and managing partner-based relationships with customers. Brian is running this as a private, long-term business that will support the important blood bank industry for decades to come. Quote from Brian Forbis, CEO and president of BBCS “We don't have churn in customers, and we don't have churn in employees either. The people we attract to our blood bank software business really get bought in that we're helping people. We tell our team that you are affecting the lives of tens of thousands of people every day “There's a reason we're regulated because we make decisions on the safety and efficacy of blood. And that's a big deal. We're committed to what we’re doing. We build a key component of saving lives. “I drive that home every time I can talk about it. Making quality personal is one of our key values that we emphasize and discuss frequently.” Links The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/37528255

#153: Bootstrapper Killed His First Company to Scale Up Bigger - Chris Brisson 07/18/2025

#153: Bootstrapper Killed His First Company to Scale Up Bigger - Chris Brisson Chris Brisson is the CEO and co-founder of Salesmsg, a conversational two-way texting platform that enables businesses to engage with their customers through opt-in SMS. When his first software company stalled, he shut it down and developed the Salesmsg product for a different SMS use case that served his previous customers. now provides secure SMS texting across all departments in the company, integrated directly with Hubspot CRM. It includes voice calling, sophisticated SMS automation, opt-in management, analytics, and deep CRM integration. Salesmsg has grown rapidly, exceeding $10 million in revenue with 65 employees, leveraging its deep integration with HubSpot and promoting through agency and affiliate partners. The company is independent and has no outside investors. Quote from Chris Brisson, the CEO and founder of Salesmsg “In 2015, I wrote this post to our email list of 36,000 called The Death of Call Loop. I shared the story of how I created a business I secretly despised. We were shackled and couldn't innovate. I wanted to create a better company and reinvent the business from the ground up. My second chance startup became Salesmsg. “When you start a company and it stalls, at what point do you say It's not the horse to ride? I've been there. At what point do you say, Enough is enough? Because you're only going to get older. “I've always gone after solving problems, but some problems were worthy of the adventure, others not so much. Make sure you're choosing the right opportunity because it will take seven years of your life. And you can pivot along the way, but man, you want to find out early if it's worthy of the adventure.” Links The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/37435660

#152: Practical SaaS CEO Stays On After 100% Cash Sale - Tracy Larson 07/11/2025

#152: Practical SaaS CEO Stays On After 100% Cash Sale - Tracy Larson Tracy Larson is President and CEO of WeSuite, a vertical sales automation platform designed for larger integrators who sell complete security systems for commercial and residential real estate. Tracy and the cofounders were in the security systems business before launching a sales software company for this market in 2008. is now a comprehensive solution that addresses the complex industry requirements for lead tracking, quoting, proposal management, contracting, commissions, and pipeline management. Hundreds of integrators in the US use WeSuite for their end-to-end quote-to-contract process. WeSuite grew profitably to nearly $5 million in revenue in 2024, when the founders sold 100% of the company to Valsoft, a buy-and-hold acquirer of practical software companies. Tracy remains the CEO of the company, which operates independently in the Valsoft holding company. Quote from Tracy Larson, CEO and president of WeSuite “For founders in SaaS, especially women founders, you need to find the right people to become your personal board of advisors. You don't need money to pay them. Just pick five people who you've known over the years to help you. Ask them, Would you do this for me and be a sounding board once a month? I'd like to get your perspective on topics like these for 30 minutes. It’s not a formal board, it’s just advice and perspective. “Establishing a personal board of advisors is a great idea. They can be women or men. And you can switch it up every year or so. Don’t worry about what you don't know. We all have things we don't know.” Links The Practical Founders Podcast Tune into the 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 . Get the weekly Practical Founders newsletter and podcast updates at /episode/index/show/cfb780e7-a2fb-4378-9cb4-3155d0c7dc5a/id/37355265

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