Practical Founders Podcast

Tanner Kovacevich of Lighter Capital joins Greg Head to explain how non-dilutive financing works for practical SaaS founders. Since 2010, Lighter Capital has funded hundreds of recurring-revenue SaaS companies that want growth capital without giving up ownership or board control. Tanner shares discuss how non-dilutive financing fits companies with $1M–$5M ARR that are growing steadily but don't want venture capital. He explains typical loan structures, underwriting factors like churn and revenue trends, and why capital-efficient SaaS companies are often better candidates than "grow-at-all-costs" startups. We discuss several examples of practical SaaS founders who used debt instead of equity to retain ownership and build long-term value. The conversation focuses on how certain practical founders can use capital strategically—accelerating growth while preserving control and optionality. Key Takeaways Non-Dilutive Capital – SaaS-specific debt financing allows SaaS founders to fund growth without giving up equity, board control, or long-term ownership upside. Capital Sequencing – Smart founders combine funding types over time, using non-dilutive capital early before considering equity later. Retention Matters – High churn or declining revenue trends are the biggest red flags when underwriting recurring-revenue SaaS businesses. Ownership Economics – Avoiding early dilution can preserve tens of millions of dollars in founder equity in successful outcomes. Capital Efficiency Wins – Many profitable SaaS companies grow steadily and still attract buyers without needing big VC funding. Quote from Tanner Kovacevich, VP of Sales at Lighter Capital "Often we fund founders that just want to have a little more cash on hand and not have to manage cash so closely. What does that open up for the founder's mindset alone? To just have some extra cash on hand, to go out and hire whoever they want, an account executive, SDR. Because a lot of it can be psychological. "It's not only the grand initiatives; it can just be the ability to breathe, extend your runway to look ahead. Maybe you want to offload a couple of things you're working on as the CEO, like acting as an accountant when you're the strategic CEO and trying to manage sales day to day.  "Lighter Capital provides non-dilutive debt financing for B2B SaaS companies, but we also work with other recurring revenue types of model technology companies. With Lighter, there are no warrants on our loan, no personal guarantees that the founder has to place, and minimal financial covenants on it." Links Tanner Kovacevich on LinkedIn Lighter Capital on LinkedIn Lighter Capital website Bootstrapped Podcast Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital. In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.  Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period. Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.  The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Vivek Bhaskaran is the founder and CEO of QuestionPro, a bootstrapped survey and customer-experience research software platform they have been building for more than 25 years. Based in the Bay Area, Vivek has grown the company globally without venture capital, staying deeply involved in product and running the business as both CEO and de-facto chief product officer. As QuestionPro crossed $10M then $30M in revenue years ago, private equity firms and acquirers started calling. Vivek chose not to sell and instead kept building. Over the years he has completed about ten small acquisitions and expanded the platform while staying nimble as an independent company. In this conversation, Vivek explains why having fun, liking your team, and taking some profits along the way makes it possible for founders to play the long game. He also shares how AI is changing market research and why most AI use cases still need experimentation. Key Takeaways Founder Product Ownership – Vivek still acts as chief product officer, believing founders should stay close to the product and customer problems. Small Acquisitions Strategy – Rather than selling, QuestionPro grew through about ten small acquisitions that expanded capabilities and distribution. Practical AI Adoption – Most AI experimentation fails early, so the team tests many use cases and keeps the ones customers actually adopt. Sales Efficiency Gains – AI dramatically improves painful processes like RFP responses and compliance questionnaires that previously took hours. Synthetic Research Data – Vivek believes AI-generated personas and synthetic respondents will transform early-stage market research within a few years. Quote from Vivek Bhaskaran, founder and CEO of QuestionPro "Two things matter to me that have allowed me to be the founder and CEO for 25 years. Number one, can I wake up every day and have the same level of energy, enthusiasm, and fun? Work and fun, and everything has to be correlated at this point. There is just one life. "Number two is the people around me. I love the team that works with me and hopefully they like working with me too. These are the two things that matter to me: Am I having fun? Am I having fun with the people around me? You got one life, so can you mesh those two things together?  "Ask yourself, am I personally in the game? Do I really want to do this? If those two things are true, then I'd say keep going. How you feel, what you're doing in the morning, how you show up all day, and then who you work with. These are not external. You control both these variables reasonably well." Links Vivek Bhaskaran on LinkedIn QuestionPro on LinkedIn QuestionPro website Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Juan Ignacio Garcia Braschi is a partner at L40, a boutique SaaS M&A advisory firm with offices in Madrid, Lisbon, and Miami. After two decades in banking, private equity, and operating roles, including serving as CFO of ride-hailing company Cabify, he now helps SaaS founders sell companies typically valued between $20M and $200M. L40 works primarily with B2B SaaS companies doing $5M–$50M ARR, most of them bootstrapped or lightly funded, including companies in Europe and Latin America. Juan explains how today's buyers evaluate SaaS companies, why Rule-of-40 performance still matters even with AI, and how growth rate, retention, and profitability determine valuation ranges of roughly 4–8x ARR. Key Takeaways Growth Drives Valuation: Growth rate correlates most strongly with SaaS multiples. Companies growing 50% command much higher valuations than those growing 20%. Rule Of 40 Still Matters: Buyers increasingly expect SaaS companies to combine strong growth with some profitability. Financial Buyers Dominant: Private-equity-backed platforms acquiring add-ons are the most active buyers for $50M–$100M SaaS companies today. Sell During Momentum: Smaller companies growing 20–40% annually can be an ideal window for acquisition before growth naturally slows. Quote from Juan Ignacio Garcia Braschi, Managing Director and Partner at L40 "If you think that you're going to sell your SaaS company, you should think of that two years ahead of when you want to sell. So don't wait until you're burned out. "Keep in mind that you will have to make a profit at some point to sell to serious financial buyers. So when your company is growing at decent 20, 30, 40% year over year rates, that's probably the sweet spot for selling.  "Significant funds have been raised in the past 24 months and that has to be deployed. Traditional private equity firms are more more interested in tech. These days you see more and more traditional private equity firms going into tech and that's increasing competition and driving multiples up." Links Juan Ignacio Garcia Braschi on LinkedIn L40 on LinkedIn L40 website Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital. In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.  Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period. Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.  The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Simon Swords founded Fundipedia after starting in a backyard shed building bespoke software. Originally a custom development shop, his firm built a data governance platform for major buy-side asset managers including HSBC, Barclays, and Legal & General. Over time, Fundipedia evolved into a high-retention enterprise SaaS platform with strong net revenue retention and Rule of 40 performance. Simon navigated long consultative sales cycles, regulatory tailwinds, and a tightly networked financial services market to build a durable recurring revenue engine. After turning down an initial offer, Simon grew ARR further and ultimately sold in 2024 at approximately 10x ARR. He exited fully, used ChatGPT extensively in diligence, and now reflects on endurance, discipline, and surviving long enough for luck to compound. Key Takeaways Survive First — Don't make a mistake that kills you or the business. Staying alive creates the opportunity for luck to compound. Enterprise Patience — Two-year sales cycles are normal at the top end. Persistence and reputation matter more than speed. Rule Of 40 Discipline — Strong growth plus profitability gives founders leverage in exit timing and valuation. Problems Over Product — Founders obsess over product; buyers care about solving painful, expensive problems. Build To Exit Cleanly — Structure the company so it runs without you before you start acquisition conversations. Quote from Simon Swords, Founder of Fundipedia "I think the most important thing is not to make a mistake that kills you or the business. While you're in the arena and you've not been taken out yet, dragged off by the hyenas or lions, whatever they used back in the Roman days, you've still got a chance to make something magical happen. "You do something stupid, kill the business, kill your reputation, you're done. Entrepreneurs hate the word luck. I do feel luck. I am lucky. Of course I'm lucky. I have to be lucky. You make your own luck.  "But I'll tell you what I didn't do. I didn't make a mistake that killed me or the business and the entire way through. Even when I was going through hell, never, no matter how neurotic or anxious or all the negative kind of traits you can imagine would have flown through me. I never made a mistake that killed the business." Links Simon Swords on LinkedIn Fundipedia on LinkedIn Fundipedia website FE fundinfo website Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned. If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system. Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools. Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Steve Reynolds didn't start TripBam to disrupt the global hotel industry—he simply noticed that corporations weren't getting the discounts they negotiated, and no one was checking. After 30 years in travel technology, he saw a broken system hiding in plain sight. What began in 2013 as a consumer hotel re-shopping tool quickly revealed a much bigger enterprise opportunity. When a corporate client offered to pay a subscription fee, Steve pivoted from B2C to B2B—and never looked back. TripBam went on to serve 250 of the world's largest companies, saving clients 5–10% on existing hotel bookings and up to 30% when switching properties.  TripBam grew to $8–10M in revenue, with 50 employees across the U.S. and Europe, and operated as a Rule-of-60 SaaS business. Then COVID hit, transactions dropped 95% in two weeks, and the company had to prove its resilience before ultimately selling in 2023 to Emburse. In this episode, Steve shares why pricing for 8x ROI made sales easy, how profitability and subscription revenue protected the business during crisis, what it's like selling into private equity, and why founders should think carefully before raising multiple VC rounds. Key Takeaways Disrupt Carefully – TripBam aligned with corporate buyers while disrupting hotels and agencies. Price for Stickiness – Targeting ~8x ROI made approvals simple and customers loyal. Profit Is Protection – Strong margins helped survive a 95% revenue collapse during COVID. Avoid Over-Dilution – Limited funding preserved founder ownership at exit. Deep Expertise Wins – 30 years in travel tech created a defensible moat. Quote from Steve Reynolds, CEO and Founder of TripBam "Fortunately for me, since I didn't take additional funding, I wasn't diluted multiple times. I've met so many founders and they go through rounds A, B, C, D, E, F, and next thing you know, they end up with 5%, 10 % of the company. And it just doesn't work.  "You might actually get to a rare big exit, but it's really not going to be all that meaningful for the founders, at the end of the day. I've never kind of fallen into that trap of just getting out in front of your skis. I tend to follow the cashflow and look guys, you know, we got to make it happen on the revenue that we're generating.  "We're not going to go out and bet the farm and borrow a bunch of money and create these crazy expectations, right?  Once you start taking outside money, you get someone else starting to make those decisions for you, whether you like them or not." Links Steve Raynolds on LinkedIn TripBam (now Emburse) on LinkedIn TripBam (now Emburse) website Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Keith Shields is co-founder and CEO of Designli, a custom software development company that's helped non-technical founders build over 200 digital products in 13 years. After struggling to build apps through unreliable agencies in his own early startup, Keith focused on fixing the many painful experiences most founders have when hiring software development teams. Designli operates as a complete outsourced engineering department for practical software founders building SaaS and AI products, mobile apps, and web applications. Their SolutionLab program means founders invest $13,800 in a 2-week design sprint of prototyping and product planning before committing to full development, reducing the risk of expensive failures that plague most custom dev projects. The company focuses primarily on vertical SaaS founders who understand their industry problems intimately but lack technical expertise. Keith recommends velocity to first revenue over perfect features, outside audits for struggling teams, and getting gut checks on your development situation, which is far less risky than making huge changes blindly when you feel stuck. Key Takeaways Black Box Risk: Most agencies operate in the dark, leaving founders guessing what's being built, why it's late, and whether progress matches expectations. Dedicated Teams Win: Full-time focused developers outperform fractional freelancers because context, ownership, and velocity compound over long projects. Get Clarity Fast: Structured upfront design sprints align founders and teams on scope, timelines, and priorities before heavy coding begins. Audit Early: A quick external code and process audit can reveal hidden problems before they turn into year-long setbacks. Trust Your Gut: If a development relationship feels wrong, get an outside perspective and fix it before making risky, large changes. Quote from Keith Shields, CEO and Co-Founder of Designli "My advice for non-technical founders that already have a product is to trust your gut when you ask, Are we getting the value out of our development team in this situation? "If you already have a product and your dev team isn't working, get an outside perspective. It's not that hard to go and get what you're doing audited by people, sometimes for free, like us, or you pay for it. You send off a copy of your code in a zip file. It doesn't even have to be the living, breathing version and say, Can you audit this and give me a gut check? "Getting an outside review of your code doesn't happen that often, surprisingly. People feel stuck in their frustrating situation until they make a huge change, and then it's a risky, huge change. So get some outside perspective early and often." Links Keith Shields on LinkedIn Designli on LinkedIn Designli website Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Will Caldwell started Snap after his first real estate software startup fizzled, pivoting from agent tools to regulated compliance data. He discovered lenders were required to buy hazard and flood certifications, and realized this was a "painkiller" product. He built Snap as a data and analytics platform for real estate and mortgage underwriting. Snap grew from a single California compliance product into a national flood data business, reaching $5M in revenue and 30 employees. The company charged per-loan transaction fees and embedded via API into mortgage software systems. With double-digit market share, Snap focused on customer experience, automation, and expanding wallet share inside lenders' workflows. In October 2024, Snap sold 51% of the company to Intercontinental Exchange, parent of ICE Mortgage Technology, at a double-digit revenue multiple. Will stayed on to scale the platform inside a much larger ecosystem. His key lesson: dominate a narrow niche, build a required product, and let strategic buyers find you. Key Takeaways Required Beats Optional – Legal compliance products create urgency and retention because customers must buy to complete revenue-generating transactions. Micro-Niche Entry – Starting in a narrow regulated segment let Snap win trust, then expand into much larger adjacent markets. API = Distribution – Embedding inside legacy systems turned Snap into a one-click button that scaled through partners' existing sales teams. Customer Experience Wins – In commodity data markets, faster, cheaper, simpler delivery became Snap's main competitive weapon. Quote from Will Caldwell, CEO and Co-Founder of Snap "You don't need to build a huge business to get a huge, life-changing exit. Just stay laser-focused. Don't chase shiny objects. I see many founders trying to boil the ocean. It is about staying focused on a single niche. "I think vertical SaaS has many great niches, and horizontal software is challenging. You need a lot of money to go after horizontal solutions across industries. However, with vertical SaaS products and niches, there is a lot of overlooked opportunity; the real estate vertical is one prime example." Links Will Caldwell on LinkedIn Snap on LinkedIn Snap website Podcast Sponsor – LaunchBay LaunchBay helps B2B software companies automate client onboarding and implementation so customers activate faster and everyone stays aligned. If your onboarding includes data collection, setup steps, approvals, training, or any level of customization, LaunchBay replaces the messy mix of emails, spreadsheets, and meetings with a clear, all-in-one onboarding system. Teams use LaunchBay to onboard clients faster, stay on top of follow-ups automatically, and deliver a smoother experience, without hiring more people or adding more tools. Visit launchbay.com/practical and get 25% off your first 3 months on any LaunchBay plan. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Luigi Mallardo joined Woffu as an early angel investor and later became CRO, helping founder Miguel Fresneda shape a practical SaaS growth path. Based in Barcelona, Spain, Woffu has built a modern cloud-based time and attendance platform for SMEs and mid-market companies, replacing legacy tools and spreadsheets with a focused, mobile-first workforce solution. Starting from just €2K MRR, Luigi led growth first through inbound, then outbound, and partner channels, increasing average revenue per account five to seven times. By 2025, the company reached nearly €500K in monthly recurring revenue, or about €6M ARR, with more than 50 employees and profitable, efficient growth across Spain. Woffu sold to Visma in 2022 following a multi-year, proactive exit strategy, with a total reported value of €20–30M including the 3-year earnout. Luigi shares how early focus, diversified revenue, and optionality shaped every decision. His biggest lesson: clarity about your endgame determines your strategy early on, including your growth model and many other important decisions. Key Takeaways Strategic Focus - Choosing one clear use case and market unlocked faster growth than chasing horizontal HR suite ambitions across Europe. Optionality First - Designing for multiple future paths gave founders leverage rather than forcing a sale based solely on valuation. Revenue - Layers Inbound, outbound, and partners created resilience while steadily raising average contract value and predictability. Exit Readiness - Warming buyers years early turned selling into a strategic process rather than a rushed financial event. Customer Success - Investing deeply in retention created low churn and made Woffu more attractive to long-term acquirers. Builder Mindset - Great CROs zoom in and out, connecting go-to-market execution with strategy, culture, and long-term outcomes. Quote from Luigi Mallardo, Chief Revenue Officer at Woffu "We chose our focus of ICP and focus of use case, to reduce the space of market optionality to get more business optionality. You see what I mean?  "The advice I give most often is to focus, which doesn't mean to close off the option of having more verticals forever, but you need 75% or 80 % of your pipeline on where you are already monetizing and building traction. And then you leave that 20 % of pipeline to do experimentations in a new vertical. "It's one of the historical challenges, especially with young founders: the feeling of losing opportunities if they decide and don't do everything. But you are losing opportunities if you go too wide and you don't focus. Just be patient, postpone, and focus on what works." Links Luigi Mallardo on LinkedIn Woffu on LinkedIn Woffu website Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital. In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.  Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period. Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.  The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Jordon Comstock is founder and CEO of BoomCloud, a vertical SaaS company serving dental practices with patient membership software. He started the company scrappy and bootstrapped, with no outside funding, after years in the dental industry managing his family's dental lab business. BoomCloud now does about $3M in ARR with roughly 600 dental practices and an 11-person team. The company helps dentists replace insurance-driven revenue with subscription-based patient memberships, creating higher margins and more predictable cash flow. BoomCloud has been profitable since 2016 and continues to grow steadily. Jordon shares hard-earned lessons about hiring too fast, why systems scale better than people, and how he uses AI to increase output without adding headcount. He also shares how narrowing ICP transformed sales and marketing and why he's committed to building a durable, profitable business instead of chasing a fast exit. Key Takeaways Bootstrap Talent Gap — VC-funded talent often struggles in capital-efficient environments that require ownership, speed, and scrappy execution. AI Is Leverage — AI tools helped BoomCloud increase marketing and product output without rebuilding a large team. Profit Creates Buffer — Staying profitable provided margin for mistakes and reduced stress during periods of experimentation. Slow Markets Matter — Vertical SaaS wins by matching the pace of conservative industries instead of forcing VC-style growth. Exit Isn't Required — Steady profits allow founders to "exit slowly" through distributions without selling the business. Quote from Jordon Comstock, Founder and CEO of BoomCloud "We say systems scale, people don't. And we're learning that now. Let's implement the systems first. It doesn't mean people aren't important. People are important. But they have to have a system or a process first. "We've got to build it as a company and build that foundation first. When we hired a director of marketing and said, okay, you got to generate, you know, a thousand leads a month is what we were trying to do. And he couldn't do it because he didn't have systems. Fast forward a year, we implemented SEO systems to drive consistent traffic. And we convert that traffic into leads and now a thousand leads in a month is automatic. Because we have systems. We don't have a director of marketing anymore. I guess it's me, me with systems and AI. Links Jordon Comstock on LinkedIn Boomcloud on LinkedIn Boomcloud website Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Deepak Sindwani is Managing Partner at Wavecrest Growth Partners, an active growth equity firm backing bootstrapped and lightly funded SaaS founders. They work with practical founders who've built profitable businesses to $5–$20M ARR and want help growing without VC pressure or losing control. Wavecrest invests in vertical SaaS companies growing 30–60% annually, typically profitable or breakeven. They help founders scale sales, pricing, analytics, and leadership teams while staying capital efficient. Investments are usually $10–$30M total, with founders often taking some liquidity while continuing to lead. Even with the excitement around AI-first companies from VCs, Deepak sees efficient growth equity in practical vertical SaaS as a great investment and a big opportunity for founders. AI is helping serious practical founders, not making them irrelevant. Key Takeaways Capital Efficiency Matters — Wavecrest only backs profitable or breakeven SaaS companies that already respect the business model fundamentals. Founder Liquidity Helps — Taking some money off the table reduces stress and helps founders make better long-term decisions. Vertical SaaS Wins — Deep industry knowledge and data create defensibility AI-first competitors struggle to replicate. AI Is Additive — Software plus AI and data creates more value than AI replacing SaaS systems of record. No One-Size Playbook — Growth equity works best when strategies are customized, not forced by rigid PE-style playbooks. Quote from Deepak Sindwani, Managing Partner at Wavecrest Growth Partners "We don't think B2B SaaS is dead. It may create great headlines to say, AI eats software. We think software plus AI is the right approach. Software, AI plus data. So they're harvesting and creating that data moat that is going to help make them defensible. "Then, using the AI tools, why not use the AI tools to provide more automation for customers? That's what we really think AI does: increase the ability to automate the use of their product and to get value.  "Every company that we're involved with has some AI initiative. How am I changing how I run my business? How am I changing marketing and sales and finance and customer success using AI? Every company is doing something in every function in terms of new tools and tests." Links Deepak Sindwani on LinkedIn Wavecrest Growth on LinkedIn Wavecrest Growth Partners website Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital. In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.  Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period. Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.  The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Tighe Burke is the founder of SRCH Partners, 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 Tighe Burke on LinkedIn SRCH on LinkedIn SRCH website Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Dan MacDonald is the founder and CEO of BIS Safety Software, 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 Dan MacDonald on LinkedIn BIS Safety Software on LinkedIn BIS Safety Software website Podcast Sponsor – Lighter Capital This podcast is sponsored by Lighter Capital. In the last 15 years, Lighter Capital has helped over 600 software and SaaS founders secure simple, non-dilutive financing to grow a little faster—without giving up any precious equity or board seats to investors.  Simple debt funding from Lighter Capital can range from $50K to $10 million, with straightforward terms, no personal guarantees or covenants, and up to a 4-year payback period. Go to LighterCapital.com to apply and get a quick pre-qualification. Then talk with their experienced team to create a practical funding plan to achieve your goals.  The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Robin Eissler is the founder and CEO of BoosterHub, 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 Robin Eissler on LinkedIn BoosterHub on LinkedIn BoosterHub website Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

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 Greg Head on LinkedIn Practical Founders on LinkedIn Practical Founder website Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/ The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

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 "Reignition: Transforming Stuck Startups Into Breakout Winners" 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 Dave Hersh on LinkedIn Book by Dave Hersh: Reignition: Transforming Stuck Startups into Breakout Winners Dave Hersh website Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

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 Josh Ho on LinkedIn Referra lRock on LinkedIn Referral Rock website Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Shailesh Hegde is the CEO of Hubilo, 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 Shailesh Hegde on LinkedIn Hubilo on LinkedIn Hubilo website Brandlive website Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Raju Patel founded eShow 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 Raju Patel on LinkedIn eShow on LinkedIn eShow website Podcast Sponsor – Full Scale This podcast is sponsored by Full Scale, one of the fastest-growing software development companies in any region. Full Scale vets, employs, and supports over 300 professional developers, designers, and testers in the Philippines who can augment and extend your core dev team. Learn more at fullscale.io. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Dharshan Rangegowda, founder of ScaleGrid, left a decade-long engineering career at Microsoft to solve a painful database operations problem he had lived firsthand. After early missteps selling to enterprises, he shifted to helping developers manage MongoDB, Redis, and Postgres on the cloud, bootstrapping the business from scratch. ScaleGrid grew steadily through product depth, technical support, and Dharshan's mastery of SEO—becoming the top organic result for many key searches. The company expanded into multiple database engines, added a distributed engineering team, and reached 20 employees by 2021, serving both SMB developers and some enterprise teams.  Dharshan sold a majority stake to Spotlight Equity Partners during the pandemic after receiving an unsolicited offer, later stepping out of day-to-day operations while remaining on the board.  In this conversation, Dharshan shares hard-earned lessons about product-led growth, support as strategy, SEO as a long-game advantage, and how bootstrapped founders can build meaningful outcomes in massive markets.  Key Takeaways SEO Power: SEO remains a long-term growth engine for bootstrappers because big VC-backed companies rarely have the patience to compound it. Support as Strategy: Deep, responsive technical support became ScaleGrid's differentiator and directly informed product innovation and content. Start at the Edges: Enterprises won't buy from a one-person startup, but edge users with urgent problems will — and they become your early beachhead. Bootstrap Constraints: Founder over-frugality can limit growth; strategic delegation and early team building prevent burnout and plateauing. Quote from Dharshan Rangegowda, founder of ScaleGrid "You can't take random people and make them an entrepreneur. You have to want to be an entrepreneur and want to be on your own. You have to enjoy the freedom and the risk and the upside that comes with it and the unmitigated downside as well. You have to accept and be comfortable with it.  "You want to be on your own so you can try things. You are constantly looking at problems and new solutions. You want to be around people who like that sort of process: Here's a new problem and here's a new solution.  "But the most important thing you have to do as an entrepreneur is you have to add value to your customers. And most people forget that." Links Dharshan Rangegowda on LinkedIn ScaleGrid on LinkedIn ScaleGrid website Spotlight Equity Partners (acquirer) Allied Advisers (M&A advisor) AngelPad Accelerator Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Gaurav Bhasin is the founder and managing director of Allied Advisers, an M&A advisory firm whose principals have completed over 100 sell-side transactions for software and tech founders. After two decades in investment banking and tech M&A, Gaurav is a sell-side advisor to B2B software founders who have built successful businesses and want to explore selling their companies. Allied Advisers typically works with founders selling their businesses for $20M–$200M, helping them prepare materials, run a competitive process, and negotiate terms. We discuss how today's M&A market looks very different from the 2021 bubble. Valuations have normalized, deal timelines have increased, and buyers are more disciplined. But the demand for profitable, steadily growing SaaS companies is stronger than ever. Gaurav breaks down strategic and private equity buyers, what metrics matter most, how AI influences valuations, and why most founders underestimate the emotional and operational effort required to sell. For practical founders thinking about an exit in the next few years, this episode provides clear expectations and tactical guidance. Key Takeaways Profitable Growth Wins — Buyers prefer SaaS companies growing 20–50% with real profits over faster revenue growth fueled by burn. Metrics Drive Valuation — Net retention above 110%, gross retention above 90%, and >75% gross margins increase valuation and buyer interest. Run a Real Process — A single buyer gives you no leverage. Multiple qualified buyers improve pricing, terms, and closing certainty. AI Is Lipstick — But Real — You don't need to be AI-native. Practical AI that improves product, margin, or GTM still increases buyer interest. Quote from Gaurav Bhasin, founder and managing director of Allied Advisers "The good news for SaaS founders is that the private equity community has raised about $1.5 trillion of capital, and more is being raised. And they also have access to debt. So there's $7 trillion of dry powder to do deals. Private equity is not paid to sit on the cash. And they love recurring revenue software.  "Private equity investors will typically move much faster than strategic buyers. Strategics will take a while. You need a business unit sponsor to buy into the vision, and then they will push the corporate to do the deal. But with the private equity, they will look at your financial metrics and if you fit in, they can move pretty fast.  "The one caveat with private equity compared to strategic is they generally pay a little bit less than the strategics because strategics have established distribution and GTM for higher growth, so private equity will index more on the financials." Links Gaurav Bhasin on LinkedIn Allied Advisers on LinkedIn Allied Advisers website 2025 Vertical SaaS Report - Allied Advisers Podcast Sponsor – Fraction This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.