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.


Practical Founders Podcast

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

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

Shailesh Hegde is the CEO of <a href= "https://www.hubilo.com/" target="_blank" rel= "noopener">Hubilo</a>, a Bangalore-based webinar software company that initially started during COVID as virtual events tech and raised $150M in VC funding before the market shifted. Originally joining as head of product, he stepped into the CEO role during a chaotic downturn and led the company through a full strategic reset after returning all the remaining capital to investors. When the virtual events boom collapsed, Shailesh and the team rebuilt Hubilo into a mid-market webinar platform serving B2B marketing teams. They shifted from large in-person event organizers to marketers running frequent webinars, emphasizing differentiated AI-driven content repurposing. Hubilo stabilized revenue, rebuilt its GTM motion, and reached a 50/50 split between new webinar revenue and legacy customers. Earlier this year, Hubilo was acquired by BrandLive, a U.S. enterprise video platform seeking a complementary webinar product. About 80% of Hubilo's team moved over, and Shailesh now leads product integration and customer continuity during the transition. He shares hard lessons on pivots, returning capital, leading through uncertainty, and executing a practical exit when the original VC-scale vision is no longer realistic. Key Takeaways <ul> <li dir="ltr" role="presentation">Refounder Mindset – Shailesh stepped into the CEO role and reframed the mission from hypergrowth to survival, focus, and a practical exit.</li> <li dir="ltr" role="presentation">New ICP Reality – Moving from event organizers to B2B marketers required a complete repositioning and GTM rebuild that took longer than expected.</li> <li dir="ltr" role="presentation">AI as Differentiator – Hubilo used AI-generated content and repurposing tools to stand out in a crowded webinar category with entrenched incumbents.</li> <li dir="ltr" role="presentation">Practical GTM – LinkedIn thought leadership, SEO content, and product-led demos outperformed outbound or expensive Google ads in this competitive space.</li> <li>Strategic Fit Wins – BrandLive acquired Hubilo for complementary capabilities, product acceleration, and access to a strong India-based engineering team.</li> </ul> Quote from Shailesh Hegde, CEO of Hubilo "Now that I just sold our company, I'm thinking about what's next for me. It comes down to, Will I be able to find a viable problem that people are willing to pay for and will I be able to use sort of all of this experience that I have in order to solve it really well and kick off a company off the ground? "Now is probably the best time to start a company where there's so much action, there's so much happening in AI, and it's super exciting to be in this space. It's also a great time to not have like revenue pressure on your shoulders and just think out loud, have open conversations and just be free, before you really dive in and choose a focus. "The same types of business pressures will come back as you start a company. But now is a great time to just help with transition, make sure the team is good, but at the same time, start thinking about the types of problems I want to solve in the future with a new startup." Links <ul> <li dir="ltr"><a href="https://www.linkedin.com/in/shaileshhegde/" target="_blank" rel="noopener">Shailesh Hegde on LinkedIn</a></li> <li dir="ltr"><a href= "https://www.linkedin.com/company/hubilo/?originalSubdomain=in" target="_blank" rel="noopener">Hubilo on LinkedIn</a></li> <li dir="ltr"><a href="https://www.hubilo.com/" target="_blank" rel="noopener">Hubilo website</a></li> <li><a href="https://www.brandlive.com/" target="_blank" rel= "noopener">Brandlive website</a></li> </ul> Podcast Sponsor – Fraction This podcast is sponsored by <a href= "https://www.hirefraction.com/?utm_source=practicalfounders" target="_blank" rel="noopener">Fraction</a>. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at <a href= "https://www.hirefraction.com/?utm_source=practicalfounders" target="_blank" rel="noopener">fraction.work.</a> You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

#173: From COVID Boom to Bootstrap Mode: Hubilo's Refounder Story - Shailesh Hegde

Raju Patel founded <a href="https://goeshow.com/" target="_blank" rel="noopener">eShow</a> over 25 years ago after building a speaker portal for a magazine company and realizing he had a repeatable software product. What began as a one-man shop in suburban Chicago evolved into a robust event-management platform serving associations that needed complex, multi-module functionality. His business grew steadily as he delivered registration, booth management, speaker portals, and onsite systems for demanding event teams. Today eShow has 125 employees, more than 14 integrated modules, and supports hundreds of events each year for 300+ customers, including large association conferences with tens of thousands of attendees. The company has always been profitable, self-funded, and built through careful reinvestment, steady hiring, and deep product expansion. Raju rebuilt the platform multiple times, including a shift to a modern stack. Still independent with over $10 million in revenues, Raju is now building a VP-level leadership team, exploring practical growth capital, and planning a hybrid event model that blends in-person and virtual experiences. His story highlights long-term passion, practical growth, and a deliberate shift from hands-on founder to capable CEO after decades in the game. Key Takeaways <ul> <li dir="ltr" role="presentation">Deep Domain Focus – Serving the most complex association events created defensible differentiation.</li> <li dir="ltr" role="presentation">Slow, Steady Compounding – Year-over-year growth came from incremental improvements, not big bet.</li> <li dir="ltr" role="presentation">Passion Over Money – Raju built for love of the work, not an exit, which sustained him through decades of change.</li> <li dir="ltr" role="presentation">Multiple Rewrites Needed – Long-term SaaS requires full platform rebuilds, and Raju completed two with a third underway on a modern stack.</li> <li>Late-Stage Professionalization – Hiring VPs, defining ICPs, and strengthening leadership came only after passing the $10M threshold.</li> </ul> Quote from Raju Patel, founder of eShow "Looking back after 20 years running this as a small business in software, think I would have figured out how to pull a little bit more money out. It would have given me a better peace of mind." "I wouldn't have even known how to spend if I pulled a million out back then, it would have been wasted. I was very frugal and investing in my business every year." "But now I could figure out how to spend a million dollars, on savings and other personal spending that would be meaningful. It would be liberating. I deserve it, so I'm going to spend a little bit more, not be frugal. I can be frugal in my business and in my personal life not be so frugal!" Links <ul> <li dir="ltr"><a href="https://www.linkedin.com/in/rajudspatel/" target="_blank" rel="noopener">Raju Patel on LinkedIn</a></li> <li dir="ltr"><a href="https://www.linkedin.com/company/goeshow/" target="_blank" rel="noopener">eShow on LinkedIn</a></li> <li><a href="https://goeshow.com/" target="_blank" rel= "noopener">eShow website</a></li> </ul> Podcast Sponsor – Full Scale This podcast is sponsored by <a href="https://fullscale.io/" target="_blank" rel="noopener">Full Scale</a>, 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 <a href= "https://fullscale.io/" target="_blank" rel= "noopener">fullscale.io.</a> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

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

Dharshan Rangegowda, founder of <a href= "https://scalegrid.io" target="_blank" rel= "noopener">ScaleGrid</a>, left a decade-long engineering career at Microsoft to solve a painful database operations problem he had lived firsthand. After early missteps selling to enterprises, he shifted to helping developers manage MongoDB, Redis, and Postgres on the cloud, bootstrapping the business from scratch. ScaleGrid grew steadily through product depth, technical support, and Dharshan's mastery of SEO—becoming the top organic result for many key searches. The company expanded into multiple database engines, added a distributed engineering team, and reached 20 employees by 2021, serving both SMB developers and some enterprise teams. Dharshan sold a majority stake to Spotlight Equity Partners during the pandemic after receiving an unsolicited offer, later stepping out of day-to-day operations while remaining on the board. In this conversation, Dharshan shares hard-earned lessons about product-led growth, support as strategy, SEO as a long-game advantage, and how bootstrapped founders can build meaningful outcomes in massive markets. Key Takeaways <ul> <li dir="ltr" role="presentation">SEO Power: SEO remains a long-term growth engine for bootstrappers because big VC-backed companies rarely have the patience to compound it.</li> <li dir="ltr" role="presentation">Support as Strategy: Deep, responsive technical support became ScaleGrid's differentiator and directly informed product innovation and content.</li> <li dir="ltr" role="presentation">Start at the Edges: Enterprises won't buy from a one-person startup, but edge users with urgent problems will — and they become your early beachhead.</li> <li>Bootstrap Constraints: Founder over-frugality can limit growth; strategic delegation and early team building prevent burnout and plateauing.</li> </ul> Quote from Dharshan Rangegowda, founder of ScaleGrid "You can't take random people and make them an entrepreneur. You have to want to be an entrepreneur and want to be on your own. You have to enjoy the freedom and the risk and the upside that comes with it and the unmitigated downside as well. You have to accept and be comfortable with it. "You want to be on your own so you can try things. You are constantly looking at problems and new solutions. You want to be around people who like that sort of process: Here's a new problem and here's a new solution. "But the most important thing you have to do as an entrepreneur is you have to add value to your customers. And most people forget that." Links <ul> <li dir="ltr"><a href= "https://www.linkedin.com/in/dharshan-rangegowda-5662882/" target= "_blank" rel="noopener">Dharshan Rangegowda on LinkedIn</a></li> <li dir="ltr"><a href= "https://www.linkedin.com/company/scalegrid-inc/" target="_blank" rel="noopener">ScaleGrid on LinkedIn</a></li> <li dir="ltr"><a href="https://scalegrid.io/" target="_blank" rel= "noopener">ScaleGrid website</a></li> <li dir="ltr"><a href="https://www.spotlightequity.com" target= "_blank" rel="noopener">Spotlight Equity Partners (acquirer)</a></li> <li dir="ltr"><a href="https://www.alliedadvisers.com" target= "_blank" rel="noopener">Allied Advisers (M&A advisor)</a></li> <li><a href="https://angelpad.org" target="_blank" rel= "noopener">AngelPad Accelerator</a></li> </ul> Podcast Sponsor – Designli This podcast is sponsored by <a href= "https://designli.co/practical" target="_blank" rel= "noopener">Designli</a>, 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 <a href="https://designli.co/practical" target= "_blank" rel="noopener">designli.co/practical</a>. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

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

Gaurav Bhasin is the founder and managing director of <a href="https://www.alliedadvisers.com/" target="_blank" rel= "noopener">Allied Advisers</a>, an M&A advisory firm whose principals have completed over 100 sell-side transactions for software and tech founders. After two decades in investment banking and tech M&A, Gaurav is a sell-side advisor to B2B software founders who have built successful businesses and want to explore selling their companies. Allied Advisers typically works with founders selling their businesses for $20M–$200M, helping them prepare materials, run a competitive process, and negotiate terms. We discuss how today's M&A market looks very different from the 2021 bubble. Valuations have normalized, deal timelines have increased, and buyers are more disciplined. But the demand for profitable, steadily growing SaaS companies is stronger than ever. Gaurav breaks down strategic and private equity buyers, what metrics matter most, how AI influences valuations, and why most founders underestimate the emotional and operational effort required to sell. For practical founders thinking about an exit in the next few years, this episode provides clear expectations and tactical guidance. Key Takeaways <ul> <li dir="ltr">Profitable Growth Wins — Buyers prefer SaaS companies growing 20–50% with real profits over faster revenue growth fueled by burn.</li> <li dir="ltr">Metrics Drive Valuation — Net retention above 110%, gross retention above 90%, and >75% gross margins increase valuation and buyer interest.</li> <li dir="ltr">Run a Real Process — A single buyer gives you no leverage. Multiple qualified buyers improve pricing, terms, and closing certainty.</li> <li>AI Is Lipstick — But Real — You don't need to be AI-native. Practical AI that improves product, margin, or GTM still increases buyer interest.</li> </ul> Quote from Gaurav Bhasin, founder and managing director of Allied Advisers "The good news for SaaS founders is that the private equity community has raised about $1.5 trillion of capital, and more is being raised. And they also have access to debt. So there's $7 trillion of dry powder to do deals. Private equity is not paid to sit on the cash. And they love recurring revenue software. "Private equity investors will typically move much faster than strategic buyers. Strategics will take a while. You need a business unit sponsor to buy into the vision, and then they will push the corporate to do the deal. But with the private equity, they will look at your financial metrics and if you fit in, they can move pretty fast. "The one caveat with private equity compared to strategic is they generally pay a little bit less than the strategics because strategics have established distribution and GTM for higher growth, so private equity will index more on the financials." Links <ul> <li dir="ltr"><a href= "https://www.linkedin.com/in/gaurav-bhasin-ba75601/" target= "_blank" rel="noopener">Gaurav Bhasin on LinkedIn</a></li> <li dir="ltr"><a href= "https://www.linkedin.com/company/allied-advisers/" target="_blank" rel="noopener">Allied Advisers on LinkedIn</a></li> <li dir="ltr"><a href="https://www.alliedadvisers.com/" target= "_blank" rel="noopener">Allied Advisers website</a></li> <li><a href= "https://bb16eba0-3d94-42d1-abcb-976c9f7f05be.usrfiles.com/ugd/bb16eb_ced30256e0534565a67acdb8aef4747e.pdf" target="_blank" rel="noopener">2025 Vertical SaaS Report - Allied Advisers</a></li> </ul> Podcast Sponsor – Fraction This podcast is sponsored by <a href= "https://www.hirefraction.com/?utm_source=practicalfounders" target="_blank" rel="noopener">Fraction</a>. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at <a href= "https://www.hirefraction.com/?utm_source=practicalfounders" target="_blank" rel="noopener">fraction.work.</a> You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

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

Natalie Barbu is the founder and CEO of <a href= "https://getrella.com/" target="_blank" rel="noopener">Rella</a>, a SaaS platform built to streamline collaboration and workflows for social media teams and agencies. She began as a YouTube creator, grew a following of over 300,000, and then identified the fragmentation of the creator tools market — which led her to build Rella 1.0. With some small seed funding, the first Rella version focused on content creators and made no revenue with a freemium model. With $25K in the bank and no revenue, the four cofounders thought they would shut it down. But a viral video focused on social media teams immediately created paid users and revenue for a new Rella product. "Rella 2.0" now offers all-in-one content planning, scheduling, collaboration boards, billing & analytics, an AI content strategist, and all in one workspace — for social media teams. In just 12 months, they went from having no revenue, no funding, and a hard pivot relaunch to almost $3M in ARR run-rate revenue — with only four co-founder employees. Key Takeaways <ul> <li dir="ltr" role="presentation">Charge Early: They learned the hard way that free users don't convert — monetization early was non-negotiable.</li> <li dir="ltr" role="presentation">Lean Teams Win: A small, focused team aligned tightly with a mission beats trying to scale prematurely.</li> <li dir="ltr" role="presentation">Community Is Fuel: Natalie shared behind-the-scenes of the product with early users — built trust + word-of-mouth.</li> <li>Pivot Smart: They transitioned from creator workflow tools to a full SaaS platform after validating demand. </li> </ul> This Interview Is Perfect For <ul> <li>SaaS founders pivoting after a stalled product</li> <li>Founders learning how to find product-market fit </li> <li>Teams deciding when to hire or stay lean </li> <li>Builders designing tools for marketing and content teams</li> </ul> Quote from Natalie Barbu, founder and CEO of Rella "It was about two years before we decided to pay ourselves. I was still making money from my social media. So that's how I supported myself. And then my co-founders had to find side things, which I know a lot of people say, you have to be a hundred percent all in and invested in it. "But when you're not making money, you need to find a way to support yourself. So yeah, they had some side gigs that they were working on while still working full-time on Rella. "Once we started making more money with Rella 2.0, we all bumped ourselves up and got some raises since we could afford it, which has been such an accomplishment. It's money that we're actually making from our customers and our users and the income that we're generating." Links <ul> <li dir="ltr"><a href="https://www.linkedin.com/in/nataliebarbu/" target="_blank" rel="noopener">Natalie Barbu on LinkedIn</a></li> <li dir="ltr"><a href= "https://www.linkedin.com/company/rellasocial/" target="_blank" rel="noopener">Rella on LinkedIn</a></li> <li dir="ltr"><a href="https://getrella.com/" target="_blank" rel= "noopener">Rella website -</a> Use this 10% Discount Code for Rella - practical</li> </ul> Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by <a href= "https://www.cypressgrowthcapital.com/" target="_blank" rel= "noopener">Cypress Growth Capital</a>, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at <a href="https://www.cypressgrowthcapital.com/" target= "_blank" rel= "noopener">https://www.cypressgrowthcapital.com/</a> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

#169: Practical Pivot and Relaunch Created Profitable 200% Growth - Natalie Barbu

In this episode, the founder of Practical Founders, Greg Head, shares the most powerful insights from over 165 podcast interviews and working with 40+ bootstrapped SaaS founders in his peer groups. Greg breaks down the common but less obvious traits he sees in practical founders who are quietly building valuable software companies without big VC funding. Greg shares how frugality and managed risk-taking coexist to create compounding steady growth, creating massive long-term value fpr practical founders. And independence and doing it your way are not just luxuries but real superpowers that fuel growth. These patterns have emerged across hundreds of founders he's worked with, representing over $10 billion in founder equity value created. For SaaS founders skeptical of VC templates and PE playbooks Greg shares what all practical founders do to grow from $1M to $10M ARR without betting it all. Are you wired like a Practical Founder? Key Takeaways <ul> <li dir="ltr" role="presentation">Frugal yet bold – Practical founders are unusually frugal in life but make well-timed bold bets inside their companies.</li> <li dir="ltr" role="presentation">Managed risk – They avoid betting the whole company, instead making small bets that can compound into larger wins.</li> <li dir="ltr" role="presentation">Compounding focus – Long-term, steady 20–30% growth creates exponential outcomes in SaaS over 10–15 years.</li> <li dir="ltr" role="presentation">Independence premium – Protecting their ability to do it their way is treated as a strategic advantage.</li> <li dir="ltr" role="presentation">Optionality matters – Practical founders value flexibility to sell, go long, or change direction without outside control.</li> </ul> This Interview Is Perfect For <ul> <li data-pm-slice="0 0 []">Founders building SaaS without VC funding</li> <li>CEOs who value control and sustainable growth</li> <li>Entrepreneurs exploring long-term leverage vs. quick wins</li> <li>Anyone who wants to understand the practical founder mindset</li> </ul> Quote from Greg Head, founder of Practical Founders "The simple math of a $1 million ARR recurring revenue business that grows at 30% a year, will become very valuable if it keeps growing. ? Not crazy growth, a reasonable pace. This is the fundamental principle of recurring revenue businesses, that it's a compounding machine. "If you grow at 30% for nine years, you'll have a $10 million business. And if you do that for another nine years, you will have a $100 million business. That's probably worth a billion dollars by that time. That sounds simple and not everybody gets there, of course, but practical founders think in this way. Steady, healthy compounding. "We know that in the long run, the 10 years, the 20 years, compounding makes the difference. It's a healthier approach. We actually like this approach, generally speaking. We understand the math and yes, we're doing it. Most people don't really sign up for this kind of thing." Links <ul> <li dir="ltr"><a href= "https://www.linkedin.com/in/gregheadaz/?skipRedirect=true" target= "_blank" rel="noopener">Greg Head on LinkedIn</a></li> <li dir="ltr"><a href= "https://www.linkedin.com/company/practical-founders" target= "_blank" rel="noopener">Practical Founders on LinkedIn</a></li> <li><a href="https://practicalfounders.com/" target="_blank" rel= "noopener">Practical Founders website</a></li> </ul> Podcast Sponsor – Designli This podcast is sponsored by <a href= "https://designli.co/practical" target="_blank" rel= "noopener">Designli</a>, 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 <a href="https://designli.co/practical" target= "_blank" rel="noopener">designli.co/practical</a>. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

#168: These Three Superpowers Set Practical SaaS Founders Apart - Greg Head

Darryl Pahl is the co-founder of <a href= "https://www.dfnetresearch.com/" target="_blank" rel= "noopener">DFnet</a>, a Seattle-based company providing clinical trial data management software and services. Along with his wife and co-founder, Lisa Ondrejcek, Darryl started the company more than 20 years ago after careers at Fred Hutchinson Cancer Research Center. They built DFnet around long-term client relationships in global health and clinical research. The company runs DFdiscover, an enterprise-grade electronic data capture and management platform used in clinical studies worldwide. With offices in the U.S., Canada, and South Africa, DFnet has grown to more than 50 employees and is approaching $10M in revenue. Clients range from the U.S. Department of Veterans Affairs to nonprofits like PATH and major universities. Still independent and bootstrapped, DFnet has made key moves to prepare for the future—such as bringing in a growth-focused CEO, diversifying beyond single-client risk, and shifting legacy software to SaaS and services. Darryl shares the lessons from running conservatively under debt, buying rather than building, and building a global company rooted in relationships and practical execution. Key Takeaways <ul> <li dir="ltr" role="presentation">Stability First Growth – Carrying a 10-year SBA loan forced conservative growth and taught the discipline of stability over risky expansion.</li> <li dir="ltr" role="presentation">Buying Not Building – Acquiring DataFax brought 35+ new clients overnight and proved that buying legacy software can be smarter than reinventing.</li> <li dir="ltr" role="presentation">Services Plus Software – Unlike pure SaaS, DFnet thrives by combining consulting, hosting, and software in a regulated field.</li> <li>Spouse Founders Structure – Their 51/49 ownership split avoided deadlocks and kept marriage and business aligned.</li> </ul> This Interview Is Perfect For <ul> <li>SaaS founders balancing growth and control</li> <li>Founders considering succession or sale</li> <li>Bootstrapped entrepreneurs in niche B2B markets</li> <li>Anyone curious about global health data and impact-driven tech</li> </ul> Quote from Darryl Pahl, co-founder of DFnet "The best position to be in is to say that in three to five years, we would be crazy to sell this company. It's doing so well. That would be the perfect thing. And what we're not looking for is a giant payout. We have a very modest lifestyle. "But is an asset, it is a business, and there's a business aspect. It would have to be the right type of buyer. It has to be the right fit. It has to be the right person or group that is respectful to our clients, our employees, and us as owners. "So the ideal would be to have the luxury of either not selling or being more selective rather than responding to random emails from some financial buyer or search funder." Links <ul> <li dir="ltr"><a href="https://www.linkedin.com/in/darrylpahl/" target="_blank" rel="noopener">Darryl Paul on LinkedIn</a></li> <li dir="ltr"><a href="https://www.linkedin.com/company/dfnet/" target="_blank" rel="noopener">DFnet on LinkedIn</a></li> <li><a href="https://www.dfnetresearch.com/" target="_blank" rel= "noopener">DFnet website</a></li> </ul> Podcast Sponsor – Fraction This podcast is sponsored by <a href= "https://www.hirefraction.com/?utm_source=practicalfounders" target="_blank" rel="noopener">Fraction</a>. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at <a href= "https://www.hirefraction.com/?utm_source=practicalfounders" target="_blank" rel="noopener">fraction.work.</a> You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

#167: Practical Founders Brought in CEO to Scale Their Company - Darryl Pahl

<a href="https://www.linkedin.com/in/vincentserpico/" target="_blank" rel="noopener">Vincent Serpico</a>, veteran CTO and founder of Founders Workshop, is on the front lines of the AI revolution in 2025, reshaping software development and business operations. With more than 30 years of experience building software apps, Vincent is now dedicating himself full-time to AI coaching and workshops for teams and companies to create high-leverage impact quickly. Vincent shares how practical SaaS founders are leveraging agents, vibe coding, and tools like OpenAI's Agent Kit to multiply output without adding headcount. He sees the shift from SEO to GEO, the rise of ChatGPT apps, and why domain expertise is the ultimate competitive moat for SaaS founders navigating this new economy. Now leading <a href="https://serpico.ai/" target= "_blank" rel="noopener">Serpico.ai,</a> Vincent describes how entire applications can be built without writing code, using natural language and iterative management. He stresses that daily AI use, human-in-the-loop workflows, and focusing on domain-driven innovation will give practical founders the edge in this seismic shift. Key Takeaways <ul> <li dir="ltr" role="presentation">Agents As Labor – AI agents perform multi-step workflows like employees, delivering productivity gains with human-in-the-loop oversight.</li> <li dir="ltr" role="presentation">Domain Expertise Moat – Deep customer and industry knowledge matters more than raw coding speed in the AI economy.</li> <li dir="ltr" role="presentation">Vibe Coding Skills – Non-coders can now build apps with natural language prompts, managing AI like junior employees.</li> <li dir="ltr" role="presentation">Practical AI Adoption – Founders should start with small use cases, building workflows before tackling complex projects.</li> <li>Great Arbitrage Period – Founders who embrace AI now gain massive leverage over competitors who resist change.</li> </ul> This Interview Is Perfect For <ul> <li>SaaS founders ready to apply AI beyond experiments</li> <li>Product leaders exploring AI-driven workflows</li> <li>Developers curious about vibe coding and agentic design</li> <li>Founders building lean, AI-powered teams</li> </ul> Quote from Vincent Serpico, founder of Serpico.ai "If you're not an expert in something, AI will probably make you two to three times better than you currently are. But if you are an expert in something, AI will make you 10x better. "If you're already a domain expert, using AI will make you 10x better. Those are the ones that you should be hiring and paying outpaced salaries to, and build your tiny team—domain experts who are great at AI. "If I want to use AI in real estate, I could do it, but a guy who's been a real estate agent for 30 years will do much better if he understands AI skills like how to prompt and context engineer. "So we'll see hiring domain experts and paying them outsized salaries because they're utilizing AI and producing five, six times more than they could without it." Links <ul> <li dir="ltr"><a href="https://www.linkedin.com/in/vincentserpico/" target="_blank" rel="noopener">Vincent Serpico on LinkedIn</a></li> <li><a href="https://serpico.ai/" target="_blank" rel= "noopener">Serpico AI website</a></li> </ul> Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by <a href= "https://www.cypressgrowthcapital.com/" target="_blank" rel= "noopener">Cypress Growth Capital</a>, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at <a href="https://www.cypressgrowthcapital.com/" target= "_blank" rel= "noopener">https://www.cypressgrowthcapital.com/</a> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

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

Brett Gilliland, founder of <a href= "https://growwithelite.com/" target="_blank" rel="noopener">Elite Entrepreneurs</a>, joins Greg to discuss how they help ambitious founders navigate the tough leadership journey from $1M to $10M in revenue. Brett shares how co-creating a clear, practical Purpose, Values, and Mission form the foundation of scalable organizations. He explains why moving from founder-led chaos to aligned leadership teams is the critical step that separates $1M experiments from $10M companies. With clear meeting rhythms, disciplined execution, and strong hiring practices, Elite Entrepreneurs has helped hundreds of founders become happy CEOs and build companies that run without constant founder involvement. Brett reveals the personal transformation required for founders to evolve into true CEOs who can enjoy their business more as it grows. You can reduce chaos, scale your teams, and rediscover the fun of running your business once you shift focus from "I" to "we." Key Takeaways <ul> <li dir="ltr" role="presentation">Growth Brings Freedom: Founders who learn let go in the right way often rediscover fun, profit, and time.</li> <li dir="ltr" role="presentation">Leadership Teams Required: Scaling past $3M–$10M depends on building a capable senior leadership team. </li> <li dir="ltr" role="presentation">Meeting Rhythms Drive Scale: Annual, quarterly, monthly, and weekly cadences keep teams aligned.</li> <li dir="ltr" role="presentation">CEO Core Roles: Set the vision, build the team, and secure resources—everything else gets delegated.</li> <li>Hiring as Marketing: Culture-fueled job postings act like a "bat signal" for the right candidates.</li> </ul> This Interview Is Perfect For <ul> <li>SaaS founders at $1–5M in ARR</li> <li>Business owners feeling "stuck" at their current stage</li> <li>CEOs ready to build their first real leadership team</li> <li>Entrepreneurs who want growth and a life</li> </ul> Quote from Brett Gilliland, founder of Elite Entrepreneurs "All of us get stuck in some way. We know there's a better way. We see other people figuring it out. I should be able to do this, we say, but we just didn't know what to do. "You have to do work on your business in a deliberate way. And those who do the work consistently make progress. We help them lay out the path from $1 to 10 million. Here are the things that you do. It's proven, it's practical. "Whoever has been consistent with it, quarter after quarter, month after month, week after week, doing the things that we're talking about, they start stacking wins. "Then all of a sudden, 18, 24 months later, we're at a place where we've tripled in revenue, we've doubled in team, it's fun, I've got some time back in my life. It does take time, but it's totally doable. I've seen it over and over and over again. Links <ul> <li><a href="https://www.linkedin.com/in/built2lastchamp/" target= "_blank" rel="noopener">Brett Gilliland on LInkedIn</a></li> <li><a href="https://www.linkedin.com/company/elite-entrepreneurs/" target="_blank" rel="noopener">Elite Entrepreneurs on LinkedIn</a></li> <li><a href="https://growwithelite.com/" target="_blank" rel= "noopener">Elite Entrepreneurs website</a></li> </ul> Podcast Sponsor – Designli This podcast is sponsored by <a href= "https://designli.co/practical" target="_blank" rel= "noopener">Designli</a>, 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 <a href="https://designli.co/practical" target= "_blank" rel="noopener">designli.co/practical</a>. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

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

Praveen Ghanta, founder of <a href= "https://www.hirefraction.com/" target="_blank" rel= "noopener">Fraction</a> and former CEO of HiddenLevers, shares how he turned his experience scaling a bootstrapped SaaS company into a fast-growing fractional talent marketplace. After HiddenLevers reached $8M in ARR and sold for over $100M, he realized that senior fractional engineers were the secret to delivering efficiently without expensive full-time hires. Fraction now serves over 100 SaaS clients with a vetted pool of 500 senior U.S.-based engineers and CTOs. Typical engagements run 10–30 hours a week, helping founders tackle scaling challenges in vertical SaaS, AI engineering, DevOps, and legacy system conversions. The company has reached $10M ARR in just three years while keeping half its own team fractional. Praveen explains how clients use Fraction to save costs, speed development, and even prepare for M&A due diligence with fractional CTOs. He also highlights how AI has boosted senior developer productivity by 4x, why U.S.-only context matters, and how fractional-to-full-time hiring often becomes a win-win path. This interview is perfect for SaaS founders at $1M–10M ARR, hitting scaling issues, vertical SaaS leaders needing senior engineers without VC funding, and founders considering AI-powered product features and engineering talent. Key Takeaways <ul> <li dir="ltr" role="presentation">Fractional Individual Contributors: Not just execs—senior engineers deliver hands-on code, marketing, and DevOps part-time.</li> <li dir="ltr" role="presentation">AI Productivity Boost: Senior developers using AI tools are delivering 2–4x more than peers without them.</li> <li dir="ltr" role="presentation">Cost Advantage: Starting at $5K/month, founders access senior dev talent without $200K+ full-time salaries.</li> <li dir="ltr" role="presentation">Best ICP Fit: Vertical SaaS companies at $1–10M ARR facing scaling issues or legacy migrations.</li> <li>Developer Productivity: Fraction leveraged its experience with over 100 clients to build <a href= "https://www.devhawk.ai/?utm_source=podcast&utm_medium=post&utm_campaign=Practical+Founders+&utm_content=+EP+164" target="_blank" rel="noopener">DevHawk.ai, a</a> tool that manages fractional talent and delivers results even more efficiently.</li> </ul> This Interview Is Perfect For <ul> <li>SaaS founders stuck at scaling challenges without a budget for big teams</li> <li>Bootstrappers and practical founders looking for senior engineering firepower</li> <li>Founders facing legacy code, scaling issues, or AI feature rollouts</li> <li>Non-technical founders struggling to manage offshore or junior dev teams</li> </ul> Quote from Praveen Ghanta, founder of Fraction "There are a lot of very experienced engineers who get into a senior developer role, but if they're not going to become the manager of the team, there's not a really good and obvious career path for them. "They start to get bored because they know their job inside and out and it's relatively easy for them to keep delivering. "So working on a startup on the side is actually a way for both for them to sort of enrich their career and see new things and have that creative satisfaction, but at the same time, not take the risk. There are plenty of folks that want to be full-time at the startup, but there's risk in being at a startup." Links <ul> <li dir="ltr"><a href="https://www.linkedin.com/in/pghanta/" target="_blank" rel="noopener">Praveen Ghanta on LinkedIn</a></li> <li dir="ltr"><a href= "https://www.linkedin.com/company/hirefraction/" target="_blank" rel="noopener">Fraction on LinkedIn</a></li> <li dir="ltr"><a href= "https://www.hirefraction.com/?utm_source=podcast&utm_medium=post&utm_campaign=Practical+Founders+&utm_content=+EP+164" target="_blank" rel="noopener">Fraction website (fraction.work)</a></li> <li dir="ltr"><a href= "https://www.devhawk.ai/?utm_source=podcast&utm_medium=post&utm_campaign=Practical+Founders+&utm_content=+EP+164" target="_blank" rel="noopener">DevHawk website</a></li> </ul> Podcast Sponsor – Fraction This podcast is sponsored by <a href= "https://www.hirefraction.com/?utm_source=practicalfounders" target="_blank" rel="noopener">Fraction</a>. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent. Find your next fractional senior engineer or CTO at <a href= "https://www.hirefraction.com/?utm_source=practicalfounders" target="_blank" rel="noopener">fraction.work.</a> You can start with a one-week, risk-free trial to test it out. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

#164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta

Anthony Pierri and Rob Kaminski are the co-founders of <a href="https://www.fletchpmm.com/" target="_blank" rel= "noopener">Fletch</a>, a positioning strategy firm for B2B SaaS companies. They started Fletch after observing that most founders often confuse positioning with copywriting and marketing, and built their business by helping SaaS leaders make the tough, strategic choices about who they serve and how they win. Over the last three years, Anthony and Rob have collaborated with over 400 SaaS companies, ranging from early-stage startups to rapidly growing companies. Fletch helps founders and B2B SaaS leaders clarify their positioning, sharpen their messaging, and translate strategy into effective homepage design. In our practical discussion, they help founders see that positioning is a business strategy, not copywriting, which forces clarity and tradeoffs to improve execution. They share why founders must (eventually) choose one clear path to scale efficiently and why bootstrapped SaaS leaders often make sharper bets than VC-backed peers. Key Takeaways <ul> <li dir="ltr" role="presentation">Positioning = Strategy: Positioning is a founder/CEO choice, not copywriting or branding.</li> <li dir="ltr" role="presentation">Almost Universal Problem: Most B2B SaaS founders struggle with positioning clarity.</li> <li dir="ltr" role="presentation">Anchors Drive Focus: Use category, use case, or alternative as clear positioning anchors.</li> <li dir="ltr" role="presentation">Bootstrappers Move Faster: Limited capital forces clarity that VC-backed companies delay.</li> <li dir="ltr" role="presentation">Execution Takes Time: Positioning decisions are quick, but discipline drives results.</li> <li dir="ltr">Homepage Test: Your homepage clearly reveals whether positioning is working or not.</li> </ul> This Interview Is Perfect For <ul> <li>SaaS founders stuck at $1M–$10M ARR growth plateaus</li> <li>Bootstrapped operators needing sharper messaging to scale</li> <li>Founders unclear about marketing vs positioning strategy</li> <li>B2B SaaS CEOs rethinking go-to-market focus</li> </ul> Quote from Dave Yuan, founder of Tidemark Capital "There is a difference between bootstrappers and VC-funded startup founders in successfully positioning their startups. Bootstrappers are willing to see a narrow opportunity and tackle it with focus, because almost every market is big enough to sustain a $10 million company. "I don't care how narrow you get, the world's a big place. So even with a hyper-focused, verticalized niche, or use case play, there's plenty of money if you do it well and that's very appealing to bootstrappers. "Most VC-funded founders don't focus as well, which creates problems. But the founders who truly understand positioning and the idea that it can evolve over time, whether they're venture backed or not, they start with a very narrow practice to start and succeed as a leader. " Links <ul> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/anthonypierri/" target="_blank" rel= "noopener">Anthony Pierri on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.linkedin.com/in/robkaminski/" target="_blank" rel= "noopener">Rob Kaminski on LinkedIn</a></li> <li dir="ltr" role="presentation"><a href= "https://www.fletchpm.com/" target="_blank" rel="noopener">Fletch Website</a></li> </ul> Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by <a href= "https://www.cypressgrowthcapital.com/" target="_blank" rel= "noopener">Cypress Growth Capital</a>, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at <a href="https://www.cypressgrowthcapital.com/" target= "_blank" rel= "noopener">https://www.cypressgrowthcapital.com/</a> The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

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

Dave Yuan is the founder of <a href= "https://tidemarkcap.com/" target="_blank" rel= "noopener">Tidemark</a>, an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become "control points" in their markets and grow very big. Dave and Tidemark have invested in successful vertical software companies like Toast, ServiceTitan, Jane, and CCC. Tidemark hosts its annual <a href= "https://gatsby.events/tidemark-capital/rsvp/register?e=tidemark-2025-collective-live&ref=tmbanner" target="_blank" rel="noopener">VSaaS Collective Live Event,</a> featuring experienced speakers for hundreds of vertical SaaS founders, on November 5, 2025. In this episode, we discuss the practical opportunities and risks of AI as it is currently developing in 2025 for vertical SaaS companies. Dave explains several powerful examples of how AI is being used in his portfolio companies and the new strategic questions that are being discussed. Dave also shares: <ul> <li dir="ltr" role="presentation">Why software companies are getting real results with AI and are not waiting for the AI revolution--it's here now.</li> <li dir="ltr" role="presentation">How AI-powered "systems of action" have undue influence with important users and can potentially displace entrenched systems of record software.</li> <li dir="ltr" role="presentation">How fast-growing practical software company grow efficiently with well-timed product, channel, and regional expansion.</li> </ul> Quote from Dave Yuan, founder of Tidemark Capital "There are a handful of examples where software companies with AI-powered solutions are getting two to five times what they got on a software seat with new outcome-based pricing. They are providing real hard to ROI that's measurable, oftentimes associated with revenue. "And arguably, they're only getting started because the outcomes that they're measuring are relatively low value and they can increase the value of the outcomes and price accordingly. "To capture that value, it depends on competition. Because you can add a lot of value to your customers, but you can only charge for that value unless there's not a lot of competition vying for the same thing." Links <ul> <li dir="ltr"><a href="https://www.linkedin.com/in/daveyuan" target="_blank" rel="noopener">Dave Yuan on LinkedIn</a></li> <li dir="ltr"><a href= "https://www.linkedin.com/company/tidemarkcap?trk=public_profile_topcard-current-company" target="_blank" rel="noopener">Tidemark on LinkedIn</a></li> <li dir="ltr"><a href="https://www.tidemarkcap.com/" target= "_blank" rel="noopener">Tidemark website</a></li> <li dir="ltr"><a href= "https://gatsby.events/tidemark-capital/rsvp/register?e=tidemark-2025-collective-live&ref=tmbanner" target="_blank" rel="noopener">VSaaS Collective Live event </a></li> </ul> Podcast Sponsor – Designli This podcast is sponsored by <a href= "https://designli.co/practical" target="_blank" rel= "noopener">Designli</a>, 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 <a href="https://designli.co/practical" target= "_blank" rel="noopener">designli.co/practical</a>. The Practical Founders Podcast Tune into the <a href= "https://practicalfounders.com/podcast">Practical Founders Podcast</a> 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 <a href= "https://www.youtube.com/@PracticalFounders">YouTube channel</a>. Get the weekly Practical Founders newsletter and podcast updates at <a href= "https://practicalfounders.com/newsletter">practicalfounders.com.</a> 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 <a href= "https://practicalfounders.com/peer-groups/">Practical Founders Peer Group</a> is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by <a href="https://practicalfounders.com/greg-head/">Greg Head</a>.

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#173

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

#172

#173: From COVID Boom to Bootstrap Mode: Hubilo's Refounder Story - Shailesh Hegde

#171

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

#170

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

#169

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#168

#169: Practical Pivot and Relaunch Created Profitable 200% Growth - Natalie Barbu

#167

#168: These Three Superpowers Set Practical SaaS Founders Apart - Greg Head

#166

#167: Practical Founders Brought in CEO to Scale Their Company - Darryl Pahl

#165

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

#164

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

#163

#164: SaaS Founders Save Millions With Fractional Senior Engineers - Praveen Ghanta

#162

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

#161

#162: Practical Investor - What's Working Now in AI-Driven SaaS Growth - Dave Yuan