Afleveringen
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Matthew Bullis grew up in a mud-brick hut with no running water on a small island off South Korea, was adopted to the US at 11 speaking no English. After a dot-com near-miss, he took over his brother's struggling concrete-pumping software — down to about $20,000 a year — for 90% of the company. He taught himself to code and rebuilt it from scratch.
From 2016, Bullis built RapidWorks into the operational system of record for heavy-equipment subcontractors: concrete pumping, cranes, hydrovac, and other site services. RapidWorks helps contractors book jobs, dispatch crews, manage the field, and get paid faster with accuracy and speed, taking dispatchers' productivity from 20 jobs to 60+. Today the company is near $20 million in ARR, serving more than 80% of the concrete-pumping market.
In 2023, approaching $5 million in revenue, Bullis sold a majority to Wavecrest Growth Partners and brought in a new CEO Tim Curran with a new executive team. Matthew expected to be phased out within a year. Instead, by staying flexible and solving whatever broke, he became indispensable as chief strategy officer, taking on important strategic execution roles across the company where he was needed.
Key Takeaways
Solve any problem — A bootstrapper's real value is surviving anything and solving whatever breaks. Stay flexible — Don't trade on past wins; credibility comes from the value you create now. Sit with customers — Weeks in their offices surfaced problems they never thought to ask for. Hire your boss — A ready-made CEO and team de-risk the scale a founder can't reach alone. Keep perspective — Nothing is as good or as bad as it feels in the moment.Quote from Matthew Bullis, Co-Founder and CSO of RapidWorks
"To stay useful and relevant when you're not the CEO any more, you have to be flexible. People overemphasize the value of what they've done in the past: look at all the great things I did. But that's like living in your high school glory days. It doesn't merit much, and you can't expect people to give you credibility just for what you built.
"Your real value is surviving anything and solving any problems. Take that to heart — I can survive anything, I can solve any problem, I can create value for myself and the people around me. Under any difficult situation, people are drawn to people of value.
"So I stopped staying quiet. When I saw things weren't done right, I spoke up, and the seasoned leadership saw my opinions had value. When people see value in you, and you really help, they want you on their team — that's how I won the other executives over."
Links
RapidWorks on LinkedIn RapidWorks website Wavecrest Growth Partners Podcast Sponsor – Vista Point AdvisorsThis podcast is sponsored by Vista Point Advisors, a leading investment bank for founder-led software, AI, and internet companies. Vista Point works exclusively on the sell side, providing unconflicted M&A and capital raising advice to help founders maximize business value, evaluate their options, and realize ideal outcomes.
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.
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Nick Olsen is the Head of AI Innovation at Mainsail Partners, where he works hands-on with 25 scaling vertical SaaS companies helping them adopt AI in engineering and product. Before joining Mainsail, Nick spent 20 years helping build ResMan from a 3-person startup into a scaled software company serving the multifamily property management market.
Today, Nick leads a team of engineers who embed directly inside portfolio companies to build AI systems alongside their teams. They don't just advise from the sidelines—they commit code, ship features, and help technical leaders redesign how modern software organizations operate.
Nick explains why AI-first engineering is no longer a competitive advantage for SaaS companies—it's becoming the minimum requirement to stay competitive. The winners won't just write code faster. They'll build better products, make better decisions, and deliver dramatically more customer value with AI-native teams.
Key Takeaways
Table Stakes — AI-first engineering is no longer optional for serious SaaS companies. It's becoming the minimum operating standard. Roles Are Collapsing — Product, design, and engineering are moving closer together as AI removes slow handoffs and bottlenecks. Velocity Misleads — Shipping 3x more features doesn't matter if customers don't want them. Outcome beats output. Judgment Wins — AI makes building cheaper and faster. Strategic product judgment becomes more valuable, not less. Agents Matter — The best teams increasingly treat AI agents like teammates with jobs, accountability, and measurable performance. UX Is Changing — Customers may increasingly stop logging into SaaS apps and interact through agents instead.Quote from Nick Olsen, Head of AI Innovation at Mainsail Partners
"We are well past any point of skepticism or any engineer that says, Hey, this isn't gonna be here forever, or this isn't my thing. Engineers no longer should be starting in the traditional code editor, the IDE. Engineering has moved to much more of an agentic approach where you're starting in the terminal or or some sort of Claude Code or Codex app.
"How we're building software has completely and radically shifted. Companies are starting to move past treating AI as a tool. They're starting to treat AI as the way that they actually operate. It's not a tool like Excel is for a financial analyst, but that's actually where I start.
"We're trying to see people transition to treat AI as an actual teammate and actually affecting change within their organization.. And that's from the product and management side as well as to the engineering side."
Links
Nick Olsen on LinkedIn Mainsail Partners on LinkedIn Mainsail Partners website Podcast Sponsor – Full ScaleThis 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.
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Zijn er afleveringen die ontbreken?
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Paul Hoeper founded InvoiceASAP after spotting a simple but painful problem in 2009: home service businesses couldn't easily create invoices or collect payments from the field using mobile devices. He started in New Orleans, launched during the earliest days of mobile apps, and built one of the first mobile invoicing products integrated with both Square and Clover. He also suffered through several payment platform providers who never lived up to their sales pitches.
Today, InvoiceASAP serves about 23,000 paying home service businesses and roughly 400,000 total users across HVAC, plumbing, roofing, landscaping, and other field service trades. The company generates just under $5M in annual revenue with only 12 employees, growing 20–40% annually through a mix of SaaS and embedded fintech revenue.
Paul shares why he shifted from a pure SaaS subscription model to embedded payments, increasing average revenue per customer from roughly $9/month to $80–$94/month. He also explains why he avoided VC funding despite operating in fintech, choosing debt financing instead to preserve control, protect optionality, and keep building on his own terms.
Key Takeaways
Revenue Shift — Moving from SaaS subscriptions to embedded payments increased average revenue per customer প্রায় 10x, from $9 to $80–94 monthly. Control Matters — Owning payment rails gave InvoiceASAP more margin, product flexibility, fraud control, and freedom from platform dependency. Debt Over VC — Paul chose debt instead of institutional equity to preserve board control and avoid forced exits or founder dilution. Vertical Focus — Home service businesses have highly specific cash flow needs that generic payment platforms often misunderstand or ignore. Fintech Reality — Payments infrastructure remains messy, legacy-heavy, and full of poor actors despite modern APIs and slick branding.Quote from Paul Hoeper, Founder and CEO of InvoiceASAP
"Most of our competitors are on stripe.we're just exceptionally technically proficient. So we built out our own entire PayFAC infrastructure as close to the line as you can get, but where we control basically all the payment rails.
Stripe is an out-of-the-box product. So if you're looking for a different way of doing payments and billing, you just have to use whatever products Stripe gives you. That's it.
And when you build it the way that we built our product and payments platform, we can do a lot--for our customer and our business model. We have the flexibility to develop instant deposit, merchant cash advances and all different types of products."
Links
Paul Hoeper on LinkedIn InvoiceASAP on LinkedIn InvoiceASAP website Podcast Sponsor – LaunchBayLaunchBay 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.
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Jerry Alderman is the co-founder and CEO of Valkre Solutions, a SaaS platform built specifically for key account managers who oversee the largest and most strategic customers in global B2B companies. After careers in engineering, sales, leadership, entrepreneurship, and customer value consulting, Jerry discovered that key account managers were still managing critical customer relationships with spreadsheets and PowerPoint.
That insight led to Valkre, which helps large companies build account plans, coordinate teams, identify growth opportunities, and manage strategic customer relationships. Today Valkre serves major enterprise customers, has grown beyond $4 million ARR, and helps organizations move key account management from disconnected documents into a structured system that can leverage AI and organizational knowledge.
In this conversation, Jerry explains why key account management may be the last major sales role that remains deeply human in the AI era. He shares lessons from building a new software category, finding product-market fit after several pivots, raising more than $5 million in practical funding from Golden Section, and why the biggest opportunities often hide inside markets that look small from the outside. Based on the transcript discussion of Valkre's growth, funding, and AI-driven market shift.
Key Takeaways
PowerPoint Problem - Hundreds of thousands of key account managers still run critical customer relationships in spreadsheets and PowerPoint. Human Workflow - Key account management depends on trust, judgment, negotiation, creativity, and relationships that AI cannot easily replace. AI Catalyst - AI isn't replacing account managers; it's finally forcing companies to digitize strategic account management processes. Category Creation - Building a new software category takes longer than expected, even with strong customers and product quality. Practical Funding - Raising minority growth capital helped accelerate sales and technology investments without sacrificing founder control. Product-Market Fit - The biggest startup challenge is getting product-market fit right and finding the right feedback sources.Quote from Jerry Alderman, Co-founder and CEO of Valkre Solutions
"AI is automating a lot of processes now. I think that key account management will be the last sales role standing. I really do. I used Claude to investigate. Can AI take over key account management sales and disrupt Valkre? And here's what it says. 'No, because key account management is very relationship and trust dependent.
"It requires this trust of people and relationships in order to get this done. It can't replace that. It says real-world coordination, meaning teamwork. It involves having this team of people coordinated together. This is a very human role and it requires the human to be creative and think forward.
AI is very much an accelerator. And so you did this job. Building an account plan and doing SWOT analysis and doing white space analysis, that stuff takes time. With AI in Valkre, you can do those things so much more efficiently and effectively."
Links
Jerry Alderman on LinkedIn Valkre Solutions on LinkedIn Valkre Solutions website Winning Customers book by Jerry Alderman
Podcast Sponsor – Lighter CapitalThis 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.
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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 ScaleThis 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.
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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 – LaunchBayLaunchBay 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.
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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 CapitalThis 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.
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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 ScaleThis 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.
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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 – LaunchBayLaunchBay 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.
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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 CapitalThis 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.
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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 ScaleThis 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.
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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 – LaunchBayLaunchBay 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.
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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 CapitalThis 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.
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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 ScaleThis 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.
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Joseph Lee is the co-founder and CEO of Supademo, a fast-growing SaaS company solving a common pain: quickly creating new product demos. In just two and a half years, they built a modern, AI-powered solution that dramatically simplifies how teams showcase software.
Supademo has reached $3M ARR in 2.5 years and is growing more than 100% annually with a freemium model. The product enables teams to create interactive, annotated, and even translated demos in minutes instead of days or weeks. The freemium model, reverse trial onboarding, and viral product loops have driven strong PLG growth, while enterprise demand is now emerging as a second growth engine.
Joseph is a second-time founder with global experience from Korea to Vancouver to New York. He's raised a small amount of capital but is focused on practical execution. His approach reflects tghe broader shift of using AI to solve real workflow bottlenecks and grow efficiently without heavy funding.
Key Takeaways
Speed Wins - Reducing demo creation from weeks to minutes unlocks more usage, faster iteration, and better customer understanding Do The Work - Early traction came from building demos for prospects manually, removing friction and proving value instantly Reverse Trials - With free plans drive high conversion by letting users experience full value before choosing a plan PLG + Enterprise - Bottom-up growth creates stability, while enterprise deals add larger revenue but less predictability Constant Reinvention - Product-market fit is temporary in AI—founders must ship fast, iterate weekly, and stay paranoidQuote from Joseph Lee, Co-founder and CEO of Supademo
"There's no bread and butter GTM channel that is going to work permanently into the future. And the biggest learning that I took away was product market fit nowadays has a finite stamp when it comes to a period of time that it's valid for.
"You have to constantly reinvent yourself and be paranoid, because the market is changing, new competition is coming, and the dynamics are changing. You can't rest on your laurels, you got to be constantly innovating, like at a faster pace than ever before.
"Our team competitive advantage is the ability to move quickly and ship quickly. It's combining gut based on our intel and context of the industry and tribal knowledge with some data to act faster than anyone else. Not analysis paralysis or having everything planned out. Just shipping something that may be imperfect, but using that as leverage to learn quickly and iterate quickly."
Links
Joseph Lee on LinkedIn Supademo on LinkedIn Supademo website Podcast Sponsor – LaunchBayLaunchBay 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.
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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 CapitalThis 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.
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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 ScaleThis 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.
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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 CapitalThis 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.
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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 – LaunchBayLaunchBay 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.
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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.
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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 – DesignliThis 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.
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