Practical Founders Podcast

Hosted by Greg Head

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Jun 2026

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

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June 12, 2026Episode 20058 min

#200: The Biggest Pricing Mistakes That Hurt Growing SaaS Companies - TJ Joosten

TJ Joosten is the co-founder of RevFixr, a pricing and monetization consultancy that helps SaaS companies improve pricing, packaging, and revenue growth. Before starting RevFixr, TJ spent a decade building and selling software, helping early-stage companies find customers, refine product-market fit, and navigate pricing decisions from small startup deals to multi-million-dollar enterprise contracts. Today, he works with SaaS founders, private equity firms, and software companies ranging from $1M ARR to $20M+ in revenues. TJ and his team have worked with more than 100 software companies, helping them identify monetization gaps, redesign packaging, move upmarket, and capture more of the value they create without necessarily building new products. In our practical conversation, TJ explains why most founders systematically underprice their software, why private equity firms often see pricing opportunities founders miss. We also discuss what's changing (and not changing) in pricing and packaging with AI and agents this year. He shares savvy advice on usage-based pricing, hybrid pricing models, AI agents, and why founders should continuously test pricing rather than treating it as a fixed decision. Key Takeaways Monetization Gap - Most SaaS companies create more value every year but fail to capture it through pricing and packaging. Pricing Courage - Founders procrastinate price increases while private equity buyers immediately look for pricing opportunities. Hybrid Pricing - Combining fixed fees with usage pricing often increases expansion revenue while reducing buyer risk. Founder Ownership - Pricing works best when one person owns it while sales, product, and finance actively contribute. Constant Testing - Pricing is not fixed; every new quote is an opportunity to validate a better monetization strategy. Quote from TJ Joosten, Co-founder of RevFixr "If you rarely get friction on pricing, it's rarely a barrier to entry and closing sales, then you have a pricing opportunity. If at least 20% of your deals in the negotiating stage don't push back on pricing then you're probably charging way too little. "If let's say 40 % keeps giving you pushback then of course you might want to go down. At that stage they have already invested time so they'll always also be honest about are you simply too expensive and therefore I'm not buying your solution? "Or is there a different reason? You can just straight up ask someone like why didn't you buy? And if they don't give the reason of price, then you probably don't have a pricing problem." Links Tjitte (TJ) Joosten on LinkedIn RevFixr on LinkedIn RevFixr 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.

June 5, 2026Episode 1991 hr 15 min

#199: Enterprise SaaS Built on Salesforce to a Practical Founder Exit - Rupert Mayer

Rupert Mayer is the founder of IPfolio, a vertical SaaS platform built for corporate intellectual property teams to manage patents, trademarks, renewals, and innovation workflows. Originally from Austria, Rupert stumbled into IP software while helping a patent law firm solve Y2K risks, then moved to Silicon Valley to build a modern cloud-based product on Salesforce for smaller in-house IP teams. IPfolio started as a lightweight alternative to legacy enterprise systems but gradually moved upmarket as customers like Dropbox, Square, GoPro, and Alphabet companies adopted the platform. Built largely on Salesforce with a lean team, the company grew steadily, signed six-figure enterprise contracts, and expanded to roughly 40 employees while serving increasingly complex global enterprises. After raising a small strategic investment to scale faster, IPfolio grew too quickly and burned through capital chasing larger enterprise deals that took longer to close. Rupert ultimately sold the company in 2019 to a strategic partner, stayed through multiple acquisitions, and helped position IPfolio as the flagship product inside a much larger global company. Today, he is building again—this time in climate tech. Key Takeaways Go All In - Growing software companies need full-time focus once you know the opportunity is real. Move Upmarket - Lightweight SaaS products often evolve into enterprise systems as big customers reshape the roadmap. Enterprise Leverage - Selling to innovative companies like Google accelerated product maturity and credibility faster than expected. Growth Trap - Hiring ahead of demand after rapid growth can create painful consequences when pipeline assumptions fail. Platform Advantage - Building on Salesforce dramatically reduced enterprise security, compliance, and infrastructure complexity. Quote from Rupert Mayer, Founder of IPfolio "I think the US innovation culture, especially in Silicon Valley, is very different from the business culture in Europe. I think it's just the willingness to take risks. When I started selling, I was basically now a solo entrepreneur. When I approached big companies to buy IP Folio, the early version, I did not have big names to go out with. I was a nobody. And so I walk into, what was it at the time already, a public company in Silicon Valley. I do my demo and everyone likes the product. And then they ask the dreaded question, well, how big is your company? We're two people plus a developer. And I thought that was it. This public company will never sell from, buy from this no name, more or less solo startup. And they said, wow, that's so cool. This is great. We'd love to buy from you because 15 years ago, this company was basically just three people in the garage and someone trusted them and bought their product." Links Rupert Mayer on LinkedIn IPfolio on LinkedIn IPfolio 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.

May 29, 2026Episode 19850 min

#198: Protecting the Soul of Your Company, with Eric Ries, Author of the Lean Startup

Eric Ries is the entrepreneur and author of The Lean Startup, whose work helped software founders validate ideas faster and build companies without making huge bets upfront. After years helping startups, large companies, and governments apply Lean Startup principles, Eric built the Long-Term Stock Exchange and turned his attention to a bigger question: Why do so many successful companies lose their way? In our conversation, Eric explains the idea of "financial gravity"—the hidden force that pushes companies toward short-term financial thinking as they grow. He shares cautionary stories of companies like Whole Foods, Johnson & Johnson, Silicon Valley Bank, and Costco to show how scaling, investors, boards, and even employees can gradually erode trust, mission, and long-term value. Eric's new book, Incorruptible Why Good Companies Go Bad…and How Great Companies Stay Great, offers practical ways founders can protect the soul of their companies before it's too late--even when they don't have big outside investors. He explains why founders should explicitly codify their mission into governance structures, why trust is the most underrated asset in business, and how practical founders can retain optionality while building valuable companies that endure. Drawing on two decades of work with founders, CEOs, and investors, Eric Ries reveals the forces that make companies vulnerable to destruction from within and without. Then he offers solutions that safeguard against them for the long-term. Incorruptible is the blueprint for companies that will prosper and endure without losing their soul. Key Takeaways Financial Gravity - Every growing company faces pressure toward short-term financial thinking—even without outside investors. Trust Compounds - Companies that earn trust with customers and employees often outperform financially over the long term. Founder Regret - Many founders regret selling because the mission, culture, and soul of the company disappear. Mission Protection - Values on a wall aren't enough—founders need legal and governance structures to preserve mission. Question Best Practices - Many accepted business practices optimize short-term profits while destroying long-term value. Think Long-Term - Practical founders have more optionality when they intentionally design companies to endure. Quote from Eric Ries, Author of the Lean Startup "People have woken up to this reality. Given where we're at, if you can create a bootstrap company, if you can maintain control, it doesn't make you completely safe. The problem is actually not investors, but financial thinking. "So I tell a bunch of stories in my book (Incorruptible) of companies where the issue wasn't investors, but their own employees. You start to bring in professional managers. You start to bring in a CFO, and the CFO has that extractive mindset, or even worse. "Financial gravity is one of the most underrated concepts in business. It is like trying to direct our attention away from the surface characteristics of an organization to the deeper forces that act on it. Your business model, strategy, vision, culture, these things are very important, but they are the things that we have control over. Financial gravity is a force." Links Eric Ries on LinkedIn Eric Ries on Twitter Eric Ries Podcast Incorruptible book on Amazon 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.

May 22, 2026Episode 1971 hr 15 min

#197: Scaled His Niche Vertical SaaS ERP with Growth Equity - Marc Sanderson

Marc Sanderson is the founder and CEO of INNERGY, but he didn't start as a software founder. After earning his MBA and searching for a company to buy, he and partner Walter Wilkie acquired a small architectural woodworking business in Minnesota in 1997. Running that business revealed a deep operational problem: there was no software built for how custom woodworking shops actually operated. So Marc built his own. That internal tool eventually became Innergy, a vertical SaaS ERP platform for architectural woodworking and high-end residential millwork businesses. Today, Innergy handles everything from CRM and estimating to project management, engineering, fabrication, and field installation. In 2025, the company reached roughly $25M in revenue, is growing more than 50% annually, and expects to approach $40M in 2026. After bootstrapping growth for years using profits from the original woodworking business, Marc sold 51% of Innergy to growth equity firm MainSail Partners in 2025 for more than $40M, while remaining CEO. In this episode, he shares practical lessons about vertical SaaS, customer intimacy, onboarding complex ERP systems, finding the right growth equity partner, and why strategy still matters more than AI. Key Takeaways Deep Domain — Marc built software from firsthand pain inside his own woodworking business, not from an outside startup idea. Education Matters — INNERGY advantage isn't only software. Customer education and operational thinking drive adoption and retention. Growth Equity Fit — Marc rejected investment several times before choosing a partner that could help scale—not just provide cash. Meet Customers — ERP success came from meeting customers where they are instead of forcing "best practices" immediately. Customer Intimacy — INNERGY's onboarding, benchmarking, and peer learning approach helped create ~95% retention. Quote from Marc Sanderson, Founder and CEO of INNERGY "AI is just a tool. I see organizations creating a chief AI officer. I don't have a chief Outlook officer. I don't have a chief Internet officer. I don't have a chief Web officer. It's just a tool at the end of the day." "Just because you can cook rice infinitely at no cost doesn't make you a Michelin star restaurant. It's all the other aspects of these integrated activities that make you who you are. And at the end of the day, as long as we are creating value for our customer, they will continue to write a check to us." "A lot of the AI efforts that are going on across the industry is focused on cost reduction, expense reduction internal to the software firm. Great. That helps us get to a breakeven or beyond. It helps with the rule of 40. However, it does not create more intimacy with the customer." Links Marc Sanderson on LinkedIn INNERGY on LinkedIn INNERGY website MainSail Partners 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.

May 15, 2026Episode 1961 hr 8 min

#196: Founder Conflict, Burnout, and a Successful SaaS Exit - Blakely Graham

Blakely Graham co-founded TaskRay, a project management and customer onboarding platform built inside the Salesforce ecosystem. After years working with Salesforce implementations and operations teams, she and co-founder Eric Wu saw a major gap between closing deals and successfully onboarding customers. They bootstrapped the company from a simple Kanban-style workflow app into a growing SaaS business serving increasingly complex enterprise implementations. TaskRay started with self-serve AppExchange purchases and evolved into enterprise software with six-figure contracts, serving companies with sophisticated onboarding and delivery needs. The company stayed profitable from the beginning, grew to roughly 40 employees, and eventually reached nearly $10M ARR. A major turning point came when the team repositioned around "customer onboarding" instead of generic project management, dramatically improving focus, retention, and enterprise growth. Blakely also shares the difficult founder realities rarely discussed openly: co-founder conflict, burnout, loneliness, identity shifts, and the emotional weight of leading a growing company for more than a decade. After stepping away following the 2021 sale of TaskRay to a search fund-backed buyer, she focused on recovery, advisory work, and co-hosting the Not All Business podcast to help founders and leaders feel less isolated during difficult growth stages. Key Takeaways Focus to Grow Faster — TaskRay discovered its strongest positioning by focusing narrowly on post-sale onboarding instead of generic project management. Bootstrap Discipline — The company stayed profitable from day one by growing carefully, shipping quickly, and avoiding unnecessary complexity early. Founder Burnout — Burnout showed up as physical exhaustion, emotional numbness, and losing the energy to inspire teams or create new ideas. Co-Founder Conflict — Long-term founder relationships can fracture under pressure, but respect and self-awareness can rebuild trust over time. Invest In Yourself — Peer groups, coaching, therapy, and personal health practices are essential leadership tools, not optional luxuries. Quote from Blakely Graham, Co-founder of TaskRay "This is probably the most important thing I learned as a CEO, and, I swear founders can't hear it. They just can't hear it. "You have to invest in yourself. The word "self care" drives me crazy because that's what people told me for 10 years. Self care. What are you doing for self care? I'm like, I don't know. Leave me alone. I don't have time, any down time. "Well, of course sitting on the other side of burning out and selling my company, founders just have to invest in themselves in the journey. It can be a peer group, it can be a coach. can be therapy. Heck for me, it's nature walks and going to the gym. Just do it because people don't want you to burn out. They want your leadership, so you have to invest in yourself and don't feel guilty about it. There, I said it." Links Blakely Graham on LinkedIn TaskRay on LinkedIn TaskRay website Plexus Capital 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.

May 8, 2026Episode 1951 hr 8 min

#195: Built a Calm, Profitable SaaS—Then Sold It on His Terms - Andy Alsop

Andy Alsop didn't start The Receptionist—he bought a small iPad-based visitor management app in 2013 for $250K and turned it into a real SaaS business. What began as a simple front-desk check-in tool evolved into a full visitor management system used across offices, schools, and manufacturing sites. Over a decade, Andy grew the company to 5,500 customers across 8,000 locations and more than $7M in ARR with just 30 employees. He stayed mostly bootstrapped, focused on steady growth, strong customer retention, and a unique "employee supremacy" culture that emphasized trust, transparency, and long-term loyalty. At an inflection point—needing more capital to keep up with a maturing market—Andy chose to sell rather than raise growth equity. The company was acquired by Sign In, a growth-equity-backed platform consolidating the category. In this episode, Andy shares how he evaluated buyers, avoided common exit traps, and built a company worth acquiring without chasing VC growth. Key Takeaways Simple Product, Deep System: What looks like a basic iPad app becomes complex, sticky infrastructure with integrations, compliance, and workflow depth. Bootstrap Leverage: Growing with customer revenue forced discipline, creating a profitable, efficient business attractive to strategic buyers. Employee Supremacy Works: Trust, transparency, and benefits (like every-other-Friday off) drove retention, performance, and long-term value creation. Clean Books Matter: Meticulous financial discipline prevented retrading risk and made due diligence smoother and more favorable. Exit Optionality Wins: Not needing to sell created leverage—allowing Andy to choose the right buyer instead of taking the only offer. Quote from Andy Alsop, CEO of The Receptionist "I sold 100 % of the company. It was a full acquisition. I wasn't even looking for, and this is something that my brother in tech always said: Don't build a company to sell it, build a great company and somebody will want to come along and buy it. And I think that's exactly the way it played out. We didn't go and look for the acquisition. We were pursued by Sign In and that's what happened. "Just build a great company and somebody will want to come along and buy it. Because I didn't want to just sell it. I mean, we're profitable. We're growing. We have very low churn. Great employees. We're doing great in the marketplace, I didn't really have to sell." Links Andy Alsop on LinkedIn The Receptionist on LinkedIn The Receptionist website Sign In 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.

May 1, 2026Episode 1941 hr 4 min

#194: Why Selling Your Company Can Be a Growth Strategy - Sharon Nouh

Sharon Nouh built ProSpend, a spend management SaaS platform for mid-market companies, after seeing firsthand how broken expense processes were in corporate travel. Starting with an expense tool, focused on her home market in Australia, she bootstrapped the company and landed a global enterprise as her first customer with a simple but powerful product vision. Over 10 years, she expanded ProSpend into a full spend management system covering expenses, accounts payable, purchase orders, and budgets. The company grew to about 1,000 customers and 50 employees, with annual contracts ranging from roughly $15K to $40K, driven by strong mid-market focus and channel partnerships. In 2025 Sharon sold ProSpend to ISH (Invincible Software Holdings), a strategic acquirer. She still runs ProSpend but can now accelerate expansion into the UK. After years of staying independent, she chose a acquisition partner over VC funding to maintain control and execute her long-term vision, showing how a sale can be a strategic move—not an endpoint. Key Takeaways Bootstrap Reality — It took five to six years before taking meaningful income, with constant cash flow pressure early on. Product Expansion — Growth came from adding adjacent modules CFOs needed, not chasing unrelated features or markets. Channel Leverage — Partnering with MYOB and resellers now drives about 50% of new customers efficiently. Control Matters — Avoiding VC preserved full control over timing and terms of exit decisions. Quote from Sharon Nouh, CEO and Founder of ProSpend "A couple of years ago, one of the visions that I had for ProSpend was to expand from Australia into the UK. The UK was always going to be the market that we wanted to move into, rather than the US, because it's a very aligned, very similar market. "And also because one of our competitors, WebExpenses, had been bought and sold about four times, and they were the incumbent in the UK. They were suffering. They hadn't been developing their product. There was a real gap for us to go into the UK and start picking up the mid-market there. "So the question was, do I get VC funding, even though we've always been bootstrapped. Or do I look for an acquiring partner, somebody from the UK who could take us in there with boots on the ground and market intelligence? And I chose the latter and sold the business that I still run." Links Sharon Nouh on LinkedIn ProSpend on LinkedIn ProSpend website ISH 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.

April 24, 2026Episode 1931 hr 7 min

#193: The Real Bottom of the Funnel: SaaS Onboarding That Works - Perry Rosenbloom

Perry Rosenbloom, founder of LaunchBay, previously built and sold Brighter Vision before starting his second SaaS company focused on onboarding. After running hundreds of onboarding processes per month, he saw a consistent problem: what happens after the sale is messy, manual, and often ignored. LaunchBay helps SaaS and professional services teams manage customer onboarding with structured workflows, shared client portals, and automation. The company has grown past $1M in ARR, doubling in 2025, with a focused approach on helping teams reduce onboarding time from 60–90 days to significantly faster activation. Perry shares practical lessons on onboarding as a core growth lever—not just an operational task. He explains why onboarding debt compounds, why charging for implementation improves outcomes, and how better onboarding drives retention, expansion, and long-term revenue quality. Key Takeaways Onboarding Debt Compounds - Most SaaS companies duct-tape onboarding early, but delays, inefficiencies, and churn risks compound quickly as sales scale. Activation Matters More - The real bottom of funnel isn't closed-won deals—it's when customers actually reach value and start using the product. Stop The Chase - Much of onboarding is manual follow-ups and coordination; removing this admin work unlocks higher-leverage customer success teams. Charge For Setup - Charging for onboarding improves completion rates, sets expectations, and ensures customers have real skin in the game. Segment The Process - Treating all customers the same breaks onboarding—different tiers and workflows are required for different customer types. Visibility Is Critical - Without clear visibility into onboarding progress and bottlenecks, problems are only discovered after deals are already at risk. Quote from Perry Rosenbloom, Founder of LaunchBay "There's only so long that you can duct tape a process like onboarding new customers, with just hustle to make it work. A lot of companies are using Google Docs, shared Slack spaces, shared spreadsheets, and it almost works, until it doesn't. And the biggest mistake is continuing to let it not work. "When you're founder-led and you are doing one to three implementations a month, you can get by without a dedicated tool for that. It's not going to be the best customer experience, but you can get by without a tool for that. "But when you want to start scaling, you need to build out repeatable processes that can enable every single customer to have a phenomenal experience that is consistent, that is unified and that delivers value. "That's when you start looking for a specialized solution to solve those problems and don't build up more onboarding debt. Onboarding debt is real and early-stage SaaS companies in their processes and customer experiences." Links Perry Rosenbloom on LinkedIn LaunchBay on LinkedIn LaunchBay website Free ebook: The Paid Implementation PlaybookROI calculator: Implementation margins 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.

April 17, 2026Episode 1921 hr 4 min

#192: Built A Vertical SaaS Giant In Aviation Without VC Funding - Dinakara Nagalla

Dina Nagalla built EmpowerMX over more than a decade to digitize aircraft maintenance for major airlines like American, Southwest, and United. Starting from deep domain experience inside aviation IT, he tackled a complex, high-stakes problem—replacing paper-based processes with a full execution system that improves efficiency and compliance. The company grew into a mid–double digit SaaS business serving global airlines with contracts ranging from hundreds of thousands to several million dollars annually. With a lean early team and offshore development, EmpowerMX delivered measurable ROI—often saving customers 10% or more on maintenance operations—while expanding globally with growth equity support. After surviving COVID (when revenue briefly dropped near zero) and accelerating post-pandemic digitization, Dina sold the company to IFS. He chose to exit not out of necessity, but to pursue a new purpose—now building multiple AI-driven products focused on improving human outcomes like mental health and education. Key Takeaways Vertical Expertise Wins: Deep domain knowledge created credibility and trust—critical for selling into conservative, high-risk enterprise environments. Start Small, Scale Smart: Initial product built with ~12 people, proving capital efficiency can solve very large industry problems. ROI Sells Enterprise: Clear financial impact (10%+ cost savings) overcame skepticism and justified multi-million dollar contracts. Trust Over Features: Adoption depended more on frontline trust than functionality—especially replacing paper and manual workflows. Purpose Drives Exit: Founder sold from a position of strength, driven by personal direction—not investor pressure or company distress. Quote from Dinakara Nagalla, President and CEO of EmpowerMX "Why did I sell the company when it was doing well? Life happens, you know. Primarily it was a desire driven by me that I want to do something different. So do I look back and think about it? Yes, I do. "It's just that my purpose in life kind of switched. I wanted to do more meaningful things. I wanted to do more things. We were extremely profitable the year we sold and my equity partners were really happy with how things were going. "When I exited I moved right into building new products with new teams. So I didn't like take a step back and said I need a week of break. I think I had better vacations with my family when I was still running the company. Right now I'm doing, I get up at three o'clock in the morning. I work till four in the evening. "You know, there is always this thing I hear from people all the time in my last 27 years of being in US: If you like what you do, you're not working another day. I think that is true in my case. I truly love what I do. Even when it's hard." Links Dinakara Nagalla on LinkedIn EmpowerMX on LinkedIn EmpowerMX Website IFS 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.

April 10, 2026Episode 1911 hr 11 min

#191: No Investors the 2nd Time - Bootstrapped to a Bigger Exit - Chad Ingram

Chad Ingram is the founder of Distro, an AI recruiting software company that helps mid-market and enterprise companies automate candidate screening, vetting, ranking, and scheduling. He previously built Jump, a venture-backed customer engagement software company, through a stressful growth and sale process that taught him painful lessons about fundraising, control, and acquisition pressure. Distro started as a marketplace to help companies hire software engineers globally, then evolved into an AI-first recruiting platform that integrates with applicant tracking systems and helps recruiters handle far more open roles. When Chad sold the company, Distro had 14 employees and about $3.5M ARR, with revenue shifting from marketplace margins toward SaaS subscription and consumption-based contracts. Distro was acquired by Vensure Employer Solutions, a large private HR platform company that wanted Distro both for its own recruiting needs and for its 161,000 customers. Chad explains why strategic buyers cared more about healthy financials than SaaS vanity metrics, why he said no to the first offer, what he learned from selling Jump too early, and why a daily cash flow forecast gave him the freedom to choose instead of react. Key Takeaways First Offers are not always the right offers, and founders with real options can politely say no and keep building. Manual First is often the smartest way to start, proving demand with spreadsheets, email, and humans before writing software. Product Evolution happened by following customer demand, turning a hiring marketplace into an AI recruiting SaaS platform. Cash Visibility gave Chad optionality, because daily cash flow tracking removed surprises and helped him make harder decisions earlier. Quote from Chad Ingram, founder of Distro "You gotta know your numbers in detail. There are so many founders who don't know their freaking numbers. How do you not know your numbers? You just hope it all works itself out in six months? That's not how it works. You will go out of business. "I learned how to do a daily cash flow forecast when we started my 2nd company, Distro. And I've been running one every day. That might seem a little too microscopic for many, but guess what? There's no freaking surprises. "I could tell you nine months from now, the day that we would go out of business if we didn't have enough cash, unless there was some change. It's a lot less stressful knowing the facts. When you know the facts, you can make things happen. You don't have to sit and wonder and hope it works out. "I don't care if you have zero mathematical aptitude or your background is sales or something else. You have to know the basics of accounting. If you don't, you are at a huge, huge disadvantage, especially when you go to sell." Links Chad Ingram on LinkedIn Distro on LinkedIn Distro website Vensure Employer Solutions 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.