Practical Founders Podcast

Anthony Pierri and Rob Kaminski are the co-founders of Fletch, a positioning strategy firm for B2B SaaS companies. They started Fletch after observing that most founders often confuse positioning with copywriting and marketing, and built their business by helping SaaS leaders make the tough, strategic choices about who they serve and how they win. Over the last three years, Anthony and Rob have collaborated with over 400 SaaS companies, ranging from early-stage startups to rapidly growing companies. Fletch helps founders and B2B SaaS leaders clarify their positioning, sharpen their messaging, and translate strategy into effective homepage design. In our practical discussion, they help founders see that positioning is a business strategy, not copywriting, which forces clarity and tradeoffs to improve execution. They share why founders must (eventually) choose one clear path to scale efficiently and why bootstrapped SaaS leaders often make sharper bets than VC-backed peers. Key Takeaways Positioning = Strategy: Positioning is a founder/CEO choice, not copywriting or branding. Almost Universal Problem: Most B2B SaaS founders struggle with positioning clarity. Anchors Drive Focus: Use category, use case, or alternative as clear positioning anchors. Bootstrappers Move Faster: Limited capital forces clarity that VC-backed companies delay. Execution Takes Time: Positioning decisions are quick, but discipline drives results. Homepage Test: Your homepage clearly reveals whether positioning is working or not. This Interview Is Perfect For SaaS founders stuck at $1M–$10M ARR growth plateaus Bootstrapped operators needing sharper messaging to scale Founders unclear about marketing vs positioning strategy B2B SaaS CEOs rethinking go-to-market focus Quote from Dave Yuan, founder of Tidemark Capital “There is a difference between bootstrappers and VC-funded startup founders in successfully positioning their startups. Bootstrappers are willing to see a narrow opportunity and tackle it with focus, because almost every market is big enough to sustain a $10 million company. “I don't care how narrow you get, the world's a big place. So even with a hyper-focused, verticalized niche, or use case play, there's plenty of money if you do it well and that's very appealing to bootstrappers. “Most VC-funded founders don’t focus as well, which creates problems. But the founders who truly understand positioning and the idea that it can evolve over time, whether they're venture backed or not, they start with a very narrow practice to start and succeed as a leader. “ Links Anthony Pierri on LinkedIn Rob Kaminski on LinkedIn Fletch Website Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company’s future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/ The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

Dave Yuan is the founder of Tidemark, 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 VSaaS Collective Live Event, featuring experienced speakers for hundreds of vertical SaaS founders, on November 5, 2025. In this episode, we discuss the practical opportunities and risks of AI as it is currently developing in 2025 for vertical SaaS companies. Dave explains several powerful examples of how AI is being used in his portfolio companies and the new strategic questions that are being discussed. Dave also shares: Why software companies are getting real results with AI and are not waiting for the AI revolution--it’s here now. How AI-powered “systems of action” have undue influence with important users and can potentially displace entrenched systems of record software. How fast-growing practical software company grow efficiently with well-timed product, channel, and regional expansion. Quote from Dave Yuan, founder of Tidemark Capital “There are a handful of examples where software companies with AI-powered solutions are getting two to five times what they got on a software seat with new outcome-based pricing. They are providing real hard to ROI that's measurable, oftentimes associated with revenue. “And arguably, they're only getting started because the outcomes that they're measuring are relatively low value and they can increase the value of the outcomes and price accordingly.  “To capture that value, it depends on competition. Because you can add a lot of value to your customers, but you can only charge for that value unless there's not a lot of competition vying for the same thing.“ Links Dave Yuan on LinkedIn Tidemark on LinkedIn Tidemark website VSaaS Collective Live event  Podcast Sponsor – Designli This podcast is sponsored by Designli, a digital product studio that helps entrepreneurs and startups turn their software ideas into reality. From strategy and design to full-scale development, Designli guides you through every step of building custom web and mobile apps. Learn more at designli.co/practical. The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding.  A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.

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

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

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

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

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

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

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

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

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

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

Henry Valentino is the founder and CEO of EConnect, a leading provider of facial recognition software for casinos and stadiums, ensuring venue security and compliance. He founded EConnect in 2009 and pivoted several times before focusing on a security platform utilizing AI for casinos during the COVID-19 pandemic. The Econnect platform offers facial recognition surveillance software that integrates with special cameras at venue entrances to identify known security risks and ensure compliance. Security teams get immediate identification of “known bad guys” in large venues.  Econnect is approaching $10 million in revenue with hundreds of customers as a profitable business, with no outside equity funding. EConnect secured a total of $2 million in venture debt in 2019 and 2020, repaid it, and is now a growing and profitable company. Quote from Henry Valentino, CEO and founder of EConnect “Make sure you know your financial numbers yourself as the CEO. It's great to lean on accounting or finance leaders, but if you don't know them yourself, that's a big hindrance to success. “Cash is what it comes down to. If the bank account doesn't have enough cash, they're only calling one person to get that resolved and that's you. If you get into trouble, you'll be trying to cut costs, which is not a way to grow a SaaS business.  “To continue growing, you need to increase your spending and capacity to take on new customers. How much does it cost to keep these doors open every month? How much cash are we going to bring in? What do we need to billl to put us in a profit position every month?” Links Henry Valentino on LinkedIn EConnect on LinkedIn EConnect website Costella Kirsch 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.

Josh Turley is CEO of RTA Fleet Management, a fleet management software company that his grandfather started in the 1980’s and ran as a small family business for decades. Then Josh’s father ran the business until 2015, never growing this slow, old-school business past $2 million in revenues. Josh had worked in the business before, but in 2016, Josh bought the business, to over as CEO and slowly began to make improvements—and mistakes—as they started to grow.  Josh had an ambition to grow the company and learn how to be a real CEO. They started retooling their code to build modern cloud software, investing heavily for many years. They transformed their leadership, staff, business model, pricing, marketing, tech stack, and culture as they grew faster. They also focused on state and local government fleets as they grew.  The bootstrapped company grew steadily, with 75 employees and a $15 million annual recurring revenue (ARR) run rate in 2024, supported by some debt. In 2025, Josh closed a $30 million investment round from Susquehanna Growth Equity, a practical growth equity investor that invests in steady SaaS businesses.  Josh is a long-time member of my Practical Founders CEO Peer Groups. He is an avid learner, attending conferences, reading books, hiring consultants, and continually seeking new knowledge.  In this episode, Josh also talks about: How difficult it was to transform an old business into a new one Why their Purpose, Values, and Mission drive successful hiring Why he chose to take on growth equity investors and de-risk with secondary investment Quote from Josh Turley, CEO of RTA “Every problem is a leadership problem. The biggest challenge in building a SaaS business is always the people—making sure you get the right people on the bus in the right seats. We’re at 90 people now, and there's no way I can manage 90 people myself. As the CEO, it all starts with you, then your leaders.  “Most problems I see are because we got the wrong person in the wrong seat. You can't outrun that, regardless of how good the product is or how strong your financial model is. It will always catch up to you eventually, and that causes more problems than anything.  “When you get a leadership team to be 100% aligned with one another, it doesn't matter what the market's doing. It doesn't matter what the product is doing. It will figure itself out. It's a forcing function to get that alignment, and then you just can't be stopped at that point.” Links Josh Turley on LinkedIn RTA on LinkedIn RTA website Susquehanna Growth Equity website 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.

Sameer Narkar is the founder and CEO of Konnect Insights, a global SaaS company based in Mumbai that provides an omnichannel customer experience platform to consumer brands in 100 countries. Sameer created Konnect Insights in 2015 to help customer service teams respond to customers who mention their brands on social media. The product and company have expanded from a slow start working through marketing agencies in India to now distributing through ISV partners in all major global regions. The Konnect Insights product includes social listening, ticketing, reputation monitoring, and social media analytics. They have grown to 140 employees, hundreds of customers, and $7 million ARR--without any outside funding. In this episode, Sameer talks about: Selling through agency and ISV partners to grow efficiently Competing with large, well-funded software companies How he thinks about how AI can help them compete Why he hasn’t sold the company or raised outside funding Quote from Sameer Narkar, founder and CEO of Konnect Insights “When you start a software company, you have all odds against you. You don't have enough money. There's no reason why customers would trust you against the established products. There is a 99% chance that you'll fail. “But if you're really passionate about what you're building, then don't look too far ahead. Try to achieve your smaller goals or get from zero to one. So just build something and get some early customers. We figured out a way for agencies to be interested in selling our solution to bring it to market. “Then meet directly with your end customers. It's very easy for tech founders to sit in the office and build a product the way they think. That doesn’t work. Many founders think that if they take a half-baked product, they won't get another chance. But that's not the case. You need to build relationships to help you improve and grow..” Links Sameer Narkar on LinkedIn Konnect Insights on LinkedIn Konnect Insights website 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.

Chris Erler was co-founder and COO of ComX, a sales pipeline generation for mid-market B2B companies in Germany and Europe. Chris and two other founders started the company in 2018 to conduct turnkey modern digital marketing and lead generation solutions for traditional German companies. As a tech-enabled service that combines technology, data, and people-powered solutions, ComX delivers proven results through subscription and outcome-based pricing. They grew quickly to approximately $20 million in revenue in four years before being acquired by the private equity firm FLEX Capital.  In this episode, Chris talks about: Growing a team of 70 employees in South Africa Starting in Germany with mid-market companies The challenges of debt financing of private equity buyouts Quote from Chris Erler, cofounder of ComX “99% of the time, I ask the founder, Why are you raising money from investors that early? I'm very pushy on that one because I know the freedom that you can create when building a bootstrapped business. “For me, raising money from investors and giving away shares very early means you’re not focusing on customers, but rather focusing on collecting capital to build the product without having it validated too early. I just share our bootstrapped story with ComX which I believe works well.  “That's why I'm a big fan of your podcasts. There's a huge education needed, especially in Europe. People need to be educated on how to found properly. Of course, it can go well, but the chances that something f***’s up are much higher. And then young people are in a very bad situation.” Links Chris Erler on LinkedIn ComX on LinkedIn ComX website FLEX Capital website 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.

Aaron Steffey is the co-founder and co-CEO of Propeller, an online platform that enables insurance agents and brokers to issue surety bonds instantly — without the lengthy paperwork or back-and-forth typically involved in bonding. Aaron was an insurance agent, and his co-founder cousin, Chris, was a surety bond underwriter before 2019, when they set out to revolutionize the way surety bonds are bought and sold. They initially bootstrapped with a software development partner who accepted equity instead of fees. Their first version drastically simplified the process of buying and selling surety bonds in the digital world, allowing them to grow quickly. They raised $7 million in SAFE notes from strategic partners to accelerate growth in 2021 and grow to nearly $20 million in revenue. They sold 100% of the company to Arch Capital in a strategic acquisition in early 2024. In this episode, Aaron also talks about: How this sleepy, paper-based market changed quickly in COVID Why they raised growth funding from strategic investors and not VCs Why they sold the company and are still leading the business after the sale Quote from Aaron Steffey, co-founder and co-CEO of Propeller “My biggest advice for startup founders is simply just that endurance wins. It’s the whole thing of getting back up after you're knocked down, like everyone says. I had to live that so many times. So many No's when it came to our first carrier pulling out. No, I don't want to invest. No, I don't want to use your surety product.  “There were so many times when I wanted to give up. And the same with my cousin. Had we not founded the company together, I don't know that we would have continued because there were probably times when I would have given up.   “As long as both of us weren't on the floor, one of us would just pick the other up when the other person usually was more sane, and we dragged each other along.  “A successful founder needs to have a pretty high pain tolerance and endurance to succeed. You just have to keep pushing forward. It just sounds so cliche, but that’s what it was for us.” Links Aaron Steffey on LinkedIn Propeller on LinkedIn Propeller website Arch Capital website 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.

Roy van den Broek is the founder and CEO of Rentman, a rental business management software platform for event and media production companies. Roy built software for his event equipment rental business in the Netherlands. He had over 100 software customers in Europe before selling his rental equipment company in 2015 to focus on growing his Rentman SaaS company.  Rentman grew slowly and profitably as word of mouth spread in the industry and their product evolved. In 2024, after growing to nearly 100 employees and 200,000 users across 100 countries, Roy raised a $22 million growth equity round from Expedition Capital to derisk the founder's investment and add growth capital to continue expanding.  In this episode, Roy discusses how they managed the painful growth stages as they expanded from one employee to 80 global employees, building a multi-lingual product and business, and why he chose to raise a significant growth equity investment.  Quote from Roy van den Broek, founder and CEO of Rentman “We had a lot of interest in investing in Rentman after COVID, so we ran a quick process. We ended up with 3 term sheets. You have multiple ways to look at these term sheets. You can look at the numbers and the valuation, which is a big part.  “But what's often overlooked is the other terms. The other terms are as important as the valuation because they really determine the way you work together. I think these terms might even be important or more important than the valuation. You got to understand their game and really figure out if you could get some alignment.  “In essence, you are negotiating the amount of autonomy that you have as a founder. That's basically what we prioritized. Like the board seats and who makes certain decisions, what are the decisions that require a majority vote? And I think we were able to get 100% autonomy on our side.“ Links Roy van den Broek on LinkedIn Rentman on LinkedIn Rentman website Expedition Growth Capital website 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.

Gopal Krishnamurthy is the founder and CEO of Lumel, which has a suite of products focused on enterprise performance management (EPM). Their apps allow users to plan, report, and analyze data using the modern native app framework vs. traditional SaaS on top of modern cloud data platforms such as Microsoft Fabric, Snowflake, Databricks, and others. Lumel’s products provide a full stack of integrated Planning, BI & data apps on the customers' data platforms. He grew his enterprise services company, Visual BI, to over 200 employees and sold that company to Atos in 2021, as he described in his first Practical Founders podcast interview in 2023. Gopal self-funded Lumel with a VC-sized investment and has grown it to over 300 employees in four years. Lumel is already at a revenue run rate of over $12M ARR and is growing fast. Lumel is building its apps using modern cloud data platforms, not siloed SaaS databases, allowing it to manage real-time data across applications. This bold new vision and architecture for enterprise software apps align with modern data approaches supporting AI, creating a billion-dollar opportunity for Lumel in the future. In this episode, Gopal also discusses: The challenge of transitioning from custom services to a no-touch product-led approach selling to enterprises Why VCs wouldn’t understand their technology bet and why their patience is paying off What it’s like to grow a fast-growth and innovative technology company as a bootstrapper Quote from Gopal Krishnamurthy, founder and CEO of Lumel “The main thing is it’s a big market. It’s not like we are just trying to get our first $10 million revenue. We have done that with Lumel already. We are looking at how we can get to a billion-dollar ARR business. That’s the big, bold vision. We have invested tens of millions already, and we are almost profitable. “We think we can absolutely create a billion-dollar business based on our customer feedback and traction from 3,000 customers. So, it’s not a question of product market fit. We worked with hundreds of our enterprise customers and perfected our data app products. “The other thing is that our products can work for smaller and medium-sized businesses because of our architecture and approach. It's completely horizontal: it works for all industries and all customers of all sizes.” Links Gopal Krishnamurthy on LinkedIn Lumel on LinkedIn Lumel website Power BI website 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.

Phil Stern is the operating principal of Mainsail Partners, a growth equity firm that invests in bootstrapped vertical SaaS companies. Mainsail offers deep operating support to the leaders in their portfolio companies to help them grow more efficiently. Phil leads the GTM operations team, helping their founders scale sales, marketing, and success teams.  Phil was an experienced SaaS sales leader at several companies before joining Mainsail to focus on helping their portfolio companies scale up to $30M ARR or more. Phil’s team helps founders solve challenging problems with sales leadership, rev ops technology, compensation, marketing analysis and planning, and more with deep operational insights customized for each company.  In this episode, Phil discusses these important topics. The five keys  to hiring your first head of sales to graduate from founder-led sales to a scalable sales team How Mainsail specialists partner with founders and their leaders to help them solve their most important GTM problems quickly How Phil helps with due diligence on potential investments to assess the upsides and opportunities for revenue growth Why Mainsail is focused on vertical SaaS companies with founders who are experts in their domains Quote from Phil Stern, Operating Principal at Mainsail Partners “Hiring a first head of sales is typically one of the first roles we're going to hire. This sales leader needs to be willing to sell the product. You're not coming in at $5 million of ARR to be an armchair VP. You own part of the quota, you're going to cover for a rep at a trade show or on maternity leave, whatever it takes.  “You have to be willing to sell. So if you come in just to strategize and move chess pieces around, it's just not the job for you. “If you don’t sell, you won't get close enough to the customer. For these customers in vertical end markets, you need to get close to them, learn from them, understand them, and speak to them.  “It's really back to a bootstrapper mentality. The CEO has been doing absolutely everything up and down the business. I'm asking a sales leader to do everything up and down the go-to-market.” Links Phil Stern on LinkedIn Mainsail Partners on LinkedIn Mainsail Partners website 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.