The Remarkable SaaS Podcast

This podcast interview focuses on entrepreneurial decision-making and product development. My guest is Rich Kahn, CEO of Anura. Rich has been building tech companies since 1993. In 2003, while running an ad network with his wife, clients began complaining about traffic quality issues. When he discovered no commercial fraud detection solutions existed, he reluctantly built one himself. Years later during an M&A process, potential acquirers showed minimal interest in his primary business but significant interest in this internal tool he'd developed. The rest is history.  And this inspired me, and hence I invited Rich to my podcast. We explore the practical realities of identifying your most valuable product, even when it's not what you initially set out to build. Rich shares how he tested his solution against market leaders before spinning it off as a standalone company, and why focusing on measurable results rather than flashy features has been crucial to his success. Here is a quote that captures one of Rich’s most practical business decisions: “We added a guarantee to Anura for two key reasons:  First, our accuracy is not a gimmick.  It’s the real deal.  Second, because no one else in the industry is willing to address false positives – real people misidentified as fraud.  It’s usually the number one issue that clients have with a fraud solution.  We are so confident in our solution; we have no problem guaranteeing it.” By listening to this podcast you will learn: How to recognize when your side project has more market value than your core business Why solving measurable problems creates stronger differentiation than marketing hype When to build technology in-house versus partnering with others The practical challenges of scaling a technical business in a constantly evolving landscape For more information about the guest from this week:  Rich Kahn  Website: anura.io Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on building remarkable software that creates sustainable competitive advantage. My guest is Geordy Murphy, CEO of Fobesoft. After three decades as a successful restaurateur who owned one of San Francisco's top four restaurants, Geordy sold his business and relocated to Florida. Despite having no software background, he identified a critical gap in the market while cycling one morning in 2014.  Inspired by Steve Jobs' philosophy that "if you can identify a problem and solve that problem, you have opportunity," Geordy founded Fobesoft with a vision to change how restaurants manage finance. What started as a self-funded venture with manual data entry evolved through persistence, strategic pivoting during COVID, and finding the right technology partnerships. And this inspired me, and hence I invited Geordy to my podcast. We explore the counterintuitive approach he took to scaling a vertical SaaS business when everything seemed to collapse. While many companies cut back during COVID, Geordy doubled down on technology investments after securing angel funding. His journey reveals how industry expertise combined with technological innovation created a solution that convinces the moment people see it. His methods challenge conventional wisdom about rapid customer acquisition and demonstrate how focused simplicity beats feature complexity, especially in specialized verticals. Here is a quote that captures one of Geordy's most striking business lessons: "Years ago, I read an article that when there's a downturn, so many companies start cutting, cutting, cutting. But the ones that survive and come out when the economy comes back up are those that didn't cut. They spend a little more, look for another opportunity - and that puts you ahead of all the competition." By listening to this podcast you will learn: How deep vertical expertise can compensate for lack of software industry experience when building a SaaS company Why doubling down on product quality during market downturns positions you for accelerated growth afterwards How to create a systematic "customer journey" that increases retention after experiencing rapid growth challenges Why understanding your ideal customer profile prevents wasting resources on prospects that can't benefit from your solution For more information about the guest from this week:  Geordy Murphy  Website: fobesoft.com Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on the entrepreneurial journey of persistence and adaptation. My guest is Maximus Greenwald, CEO of Warmly. After working at Google, Max and his co-founders quit their jobs to start a company with what he calls "the world's worst idea" - Tinder for co-founders.  What makes his journey fascinating is how he navigated through six pivots over three years, each time confronting the challenges of product-market fit, customer alignment, and sustainable growth.  Throughout this process, Max grappled with the central question many founders face: when to explore new ideas and when to commit fully to execution. And this inspired me, and hence I invited Max to my podcast. We explore the challenges of finding focus in startup chaos, the tension between vision and execution, and the counterintuitive reality that momentum often precedes perfection. Max's leadership principles cut through typical startup fluff with refreshing directness, challenging conventional wisdom about when to sell, how to pivot, and what metrics truly matter for early-stage companies. Here is one of his quotes  “In any company revenue is oxygen, and you need oxygen to live and to succeed. And so as we were starting to make money and make money fast, [..] we saw a excitement in the company and a devotion to work harder that we had never seen in our earlier six pivots. That's one of the most critical things: having momentum gets everyone excited to keep pushing along.” By listening to this podcast you will learn: The hidden pitfalls of pursuing product-market fit over generating actual revenue Why standard metrics often mislead early-stage founders away from what truly matters The real challenge of knowing when to stay the course versus when to pivot Why some customers might be holding back your company's growth potential For more information about the guest from this week:  Maximus Greenwald  Website: warmly.ai Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on the entrepreneurial challenge of revitalizing a 20-year-old SaaS business in a market with hundreds of competitors. My guest is Ash Didwania, CEO of Workzone. Ash took the helm of Workzone in December 2023 after the company was acquired by Big Band Software. Despite being profitable with a sticky customer base (7-year average customer lifetime), long-tenured employees (9-year average), and a must-have product, Workzone had been experiencing a six-year decline in revenue. Instead of the typical turnaround approach of immediate disruption, Ash took a counterintuitive path - learning first, focusing on existing strengths, and engaging deeply with customers before making changes. And this inspired me, and hence I invited Ash to my podcast. We explore what it takes to reverse a multi-year revenue decline while maintaining 40%+ EBITDA margins in a highly commoditized market. Ash shares how he challenged the conventional wisdom about business turnarounds by taking a path few would dare to follow. His counterintuitive approach transformed not only the company's financial trajectory but also reshaped how the entire team viewed their mission, their customers, and their path to growth. Here is a quote that captures one of Ash's most striking business lessons: "Throwing money at a problem can get you short-term results. It will not get you long-term sustainability. And so again, one of the thesis here was because we want to grow in a sustainable fashion while also improving our EBITDA margins, in some ways that acted as a forcing function, which is despite the fact that we were profitable, we did not want to tap into the profit pool and start deploying investments before identifying levers of growth that already existed." By listening to this podcast you will learn: How to turn around a declining SaaS business without sacrificing profitability or disrupting what works Why deep customer understanding can be more valuable than new feature development  How to create organizational focus through a single metric that aligns every team member The power of planning for multiple contingencies (Plans A, B, C, and D) in sales and go-to-market For more information about the guest from this week: Ash Didwania Website: workzone.com Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on transforming how B2B companies leverage customer interactions for growth. My guest is Krishna Raj Raja, CEO of SupportLogic.  From his early days as one of VMware's first support engineers, Krishna discovered something the industry had missed - the most valuable customer insights were being lost in departmental silos. Yet instead of accepting conventional solutions, he chose to build something the market initially rejected but customers immediately embraced. This inspired me, and hence I invited Krishna to my podcast. We explore the counterintuitive approach of building a B2B software company by deliberately ignoring what investors and the market considered essential. His journey reveals how challenging established industry assumptions can uncover massive business opportunities that others miss, while creating natural barriers to competition through a unique product philosophy. Here is a quote that captures one of Krishna's most striking business lessons:  "If customers are excited and investors are not seeing it, this is the right opportunity to go after, because this is an opportunity they're not going to fund."  By listening to this podcast you will learn: How to identify massive market opportunities in the disconnect between investor skepticism and customer excitement Why focusing on six wildly successful customers yields better results than chasing rapid-scale When deliberately ignoring industry "must-haves" creates stronger market positioning How to turn early customer enthusiasm into effortless enterprise sales For more information about the guest from this week:  Krishna Raj Raja  Website: supportlogic.com  Book: supportexperience.ai Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on the critical decisions that define successful scaling. My guest is David DeWolf, CEO of Knownwell. After growing Three Pillar Global to 2000 employees across nine countries, David learned that sometimes the best way to scale is to deliberately slow down. During COVID, he made the bold choice to retain all employees despite revenue decline - a decision that led to tripling the business within a year. Now with Knownwell, he's applying these scaling lessons to build an AI company with intention, starting with 500 customer interviews before writing a single line of code. Their mission: To help professional services firms prevent "surprise churn” by elevating human relationships and experiences. And this inspired me, and hence I invited David to my podcast. We explore what it really takes to build an AI company that elevates rather than replaces human relationships. His approach challenges conventional wisdom about scaling, product development, and leadership - drawing from lessons that helped him grow his previous company from startup to 2000 employees and survive multiple market crises. But what's most fascinating is how he's applying these insights to tackle one of the biggest pain points in professional services: the struggle to see relationship problems before they become relationship crises. Here's a quote from David: We had an inbound lead that found us through the podcast and ended up signing a rather large contract before we even not only wrote a line of code, but before we had an engineer on staff. By listening to this podcast you will learn: How to secure major contracts before writing a single line of code (and why this might be smarter than building first) Why CEOs should never delegate customer relationships, even when scaling rapidly How staking your brand position before having a product can accelerate your go-to-market strategy Why implementing lightweight business systems early gives you an unfair advantage in scaling For more information about the guest from this week: David DeWolf Website: knownwell.com   Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here. Yes, it’s actually daily. And yes, people actually stay subscribed. (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable.   Learn more about your ad choices. Visit megaphone.fm/adchoices

A story about transforming a horizontal solution into targeted value propositions This podcast interview focuses on the entrepreneurial journey to build sustainable growth by deeply understanding customer needs over chasing broad market opportunities. My guest is Nick Wassenberg, CEO of Cludo. Nick is a marketing veteran turned CEO with an entrepreneurial mindset shaped by working closely with founders. Previously, as employee #12 at Fulcrum, he experienced rapid-growth dynamics firsthand. His diverse background spans manufacturing, healthcare, financial services, and global consulting – driven by an insatiable curiosity to understand how different businesses work. In June 2023, he became the CEO at Cludo. Their mission: To get website visitors of critical organizations the most relevant, timely, and trusted answers. And this inspired me, and hence I invited Nick to my podcast. We explore his strategic decisions in his first 90 days. He shares how he's transforming Cludo's approach from serving everyone to deliberately focusing on specific customer segments where they can deliver the most value. Last but not least, he shares his insights on how understanding the hidden patterns in customer behavior shapes both product development and go-to-market strategy. Here's one of his quotes: “If I were going to start from the beginning, I wouldn't say 'let's have 27 different industry categories.' We would pick one and build a product that was amazing for them, and then pick another, and then broaden out from there. That's an easy mistake - your eyes get pretty big, especially in a solution set like ours. Some amount of it is universal and universally applicable - but you still have to close the niche down and find your way that way.” By listening to this podcast you will learn the following: The importance of aligning your solution with your customer's top priorities rather than trying to elevate the priority of your specific solution Where he's investing his marketing budget to solve the current challenges of trying to make outbound work in complex B2B sales The strategic advantage of focusing on input metrics that drive outcomes rather than just measuring outputs The importance of building strengths in areas outside your comfort zone to drive business growth For more information about the guest from this week: Nick Wassenberg Website: cludo.com  Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on the entrepreneurial journey to make effective leadership development available for everyone. My guest is Smadar Tadmor, CEO of Claro Mentor. Smadar Tadmor is a visionary leader who's on a mission to change the way organizations develop their managers. With over 30 years in HR and organizational development, she founded three successful consulting companies before spotting a critical gap: most leadership development programs weren't driving real behavior change.  This insight led her to found Claro Mentor in 2022, creating a platform that makes personalized leadership guidance available for every layer of an organization.  What makes her story particularly compelling is her transition at this stage in her career - moving from being a top-tier consultant to a first-time tech startup CEO, embracing a beginner's mindset while leveraging decades of domain expertise. And this inspired me, and hence I invited Smadar to my podcast. We explore her remarkable transition from successful consultant to first-time tech CEO, where she had to unlearn decades of habits to build something entirely new. She shares candid insights about the struggles of perfectionism, the surprises of product-market fit, and how bootstrapping forced tough but transformative decisions that shaped their innovative approach to leadership development. Here's one of her quotes: “I left behind an amazing 30 years of career where I was top-notch consultant, well known... and start from a place where I know nothing. And it's very humbling to be at this point. From that perspective, I could be very open to explore and take risks that I think in a different way I wouldn't be doing.” By listening to this podcast, you will learn the following: Why starting with 'knowing nothing' became Smadar's biggest advantage The surprising reason their initial AI coaching approach failed - and what insight changed everything How bootstrapping revealed a truth about their product they wouldn't have discovered otherwise The counterintuitive approach that doubled their customer adoption For more information about the guest from this week: Smadar Tadmor Website: claromentor.com Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on the entrepreneurial journey to transform thoughtful validation of the problem into confident scaling of his SaaS business. My guest is Robbert Lodewijks, Co-founder and CEO of Hulo AI. Robbert Lodewijks is an entrepreneur who understands the delicate balance between patience and ambition. His journey began with a profound realization during his studies in Taiwan - that impact requires more than just good technology. What makes Robbert's story intriguing is his methodical approach: spending four years in research before launching, then bootstrapping to validate, and only then accelerating with venture funding. This disciplined progression showcases a rare blend of scientific rigor and entrepreneurial instinct. And this inspired me, and hence, I invited Robbert to my podcast. We explore how early-stage founders can build confidence through validation rather than rushing to scale. His insights reveal how methodical customer development, thoughtful bootstrapping, and strategic timing of funding can create a stronger foundation for growth. What's particularly fascinating is his scientific approach to sales and his insights on avoiding the common pitfalls of enterprise customer development. Here's one of his quotes:  "We have one really clear definition [of success], and that is in the amount of water that we have saved. In the end, that relates to all our goals, because if we save so many Olympic-sized swimming pools of drinking water, which is 4 million (our BHAG), then it also means that we will probably build a very profitable company and make a huge impact on the world.” By listening to this podcast you will learn the following: That patient validation beats premature scaling because it builds stronger foundations. How to avoid pure sales hustle and having to rely on individual talent to secure the growth of your SaaS business. How to get everyone aligned in your company to create business velocity (not just departmental speed) Why you should always start your validation processes with end-users rather than just decision-makers. For more information about the guest from this week:  Robbert Lodewijks  Website: hulo.ai Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on the entrepreneurial journey to transform messy wearable data into standardized enterprise gold. My guest is Marco Benitez, CEO of Rook. Marco is a tech entrepreneur on a mission. He's a former Tae Kwon Do champion who transformed his athletic discipline into entrepreneurial success.  At just 22 years old (while still in college), he and his co-founder built a machine learning system for hospitals, which they successfully sold in 2006. This got him involved in clinical research - thereby working for pharmaceutical giants like Roche and Novartis. This is where stumbled across big challenges that were caused by the absence of enough meaningful health data. And this became the founding idea behind ROOK, which he founded in June 2017.  What began as a heart rate monitoring platform in 2018 evolved into a sophisticated B2B platform that now integrates with over 300 wearable devices.  Their vision: to create a healthier world by making health data accessible and meaningful.  And this inspired me, and hence I invited Marco to my podcast. We explore the journey of building a groundbreaking health data platform. Marco tells the story how COVID destroyed their fitness-center business model, and what lessons he learned in the process of pivoting. He shares his insights on enterprise sales cycles, pricing strategy, and team building. Last but not least he explains how he's deliberately portraying the startup's challenges to find the right cultural fit and his mantra of "cut through the noise and keep walking" when it comes to facing tough decisions.  Here's one of his quotes Once you switch your mind, instead of selling a product, you are selling data, and you are really selling a problem, that's when they put your price on you. Because if you are selling a very good solution to their problem, that's when they are will say, ‘This is a no-brainer. I don't care how much you are going to charge to me.’ During this interview, you will learn four things: What insights changed their ability to charge premium prices in enterprise deals? What's he's doubling down on successfully to shorten the typically long sales cycles.  Why he emphasizes radical transparency, sharing financials and challenges with potential hires. His secrets to staying persistent and disciplined, even when facing doubts or lack of motivation For more information about the guest from this week: Marco Benitez Website: Rook  Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices