The Remarkable SaaS Podcast

This podcast interview focuses on the entrepreneurial journey of turning transparency into business advantage. My guest is Zach Wasserman, Cofounder and Tech Evangelist of Fleet.  With over a decade of experience in open source software development, Zach helped create the widely-adopted OSquery project at Facebook in 2014, which has since become an industry standard for device visibility and is now governed by the Linux Foundation. After transitioning through a role at Kolide (later acquired by 1Password), Zach became the maintainer of a project that would eventually evolve into Fleet. Throughout his entrepreneurial journey, Zach discovered that what truly energizes him is "building software that's making someone's life better" - specifically IT administrators and security professionals who manage company devices. This human-centered approach led him to transform a personal passion project into a rapidly growing company that's challenging traditional business models in enterprise software This inspired me to invite Zach to my podcast. We explore how being open source gives Fleet a strategic edge. His approach rejects the common belief that enterprise sales requires complexity and secrecy. We discuss how community building leads to faster adoption and better results than traditional sales tactics. The formula is simple: be transparent, earn trust, and close deals faster. Here's one of his quotes: "The best way to lose a deal is to our own open source product, because those people remain prime prospective customers that we really need to continue to understand and figure out how we are going to build enough new value in that premium product for them to want to pay for it." By listening to this podcast, you will learn: How building on existing open source foundations can give startups immediate credibility with enterprise customers Why passionate early adopters can close deals remarkably easily compared to traditional prospects The entrepreneurial wisdom of identifying and connecting with actual budget holders while still maintaining engineer enthusiasm How customer-driven unexpected use cases can dramatically expand your market vision and product roadmap For more information about the guest from this week:  Guest: Zach Wasserman  Website: fleet.com Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on what it takes to build a successful software company by following your convictions even when easier paths tempt you. My guest is Jan Bruce, CEO of meQuilibrium (MeQ). In 2011, after years in the media industry during its technological disruption, Jan witnessed firsthand how stress and resistance to change were devastating careers and organizations. Despite having no background in technology or clinical work, she made the bold decision to create a software solution when she barely understood what a software application was.  For the first five years, she and her team worked for almost nothing, deliberately avoiding the tempting direct-to-consumer route that was attracting massive funding for competitors, instead patiently building a B2B model that would prove more sustainable long-term. And this inspired me, and hence I invited Jan to my podcast. We explore the counterintuitive leadership decisions that led to her company's success while competitors faltered. Her approach challenges conventional wisdom in three critical areas:  avoiding the "capital trap" of raising too much money too early,  resisting the temptation to pursue direct-to-consumer strategies despite industry hype,  and having the patience to discover your true value proposition through customer insights rather than preconceived notions.  Jan's leadership journey reveals that sometimes the most profitable path is the one where you say "no" to what everyone else is saying "yes" to. Here is a quote that captures one of Jan's most striking business lessons: "There was a time when there were a lot of we had potential competitors entering in the direct to consumer space, and they were raising a lot of money, which, as you know, from a tech perspective, capital can deliver speed to build. And so there's always that temptation to, well, should we do it to get the money? But we didn't do it, and it was the right thing to do." By listening to this podcast you will learn: How to achieve "funding freedom" by bootstrapping until investors need you more than you need them Why saying "no" to popular market trends can create a sustainable competitive advantage How to discover your true value proposition by listening to customers rather than industry hype The leadership mindset required to build a profitable software company when you have no technology background For more information about the guest from this week:  Guest: Jan Bruce  Website: meQuilibrium.com Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on the entrepreneurial wisdom gained through building a data-driven business from scratch. My guest is Samuel Logan, Founder and CEO of Evidencity.  After bootstrapping Evidencity as his fourth venture, Samuel Logan has spent a decade building a company with a profound mission: creating transparency to eliminate modern slavery in global supply chains. His journey began by addressing a critical gap in the market—helping multinational corporations access reliable data about their suppliers in regions where information wasn't available online. What started as a network of people physically retrieving documents in over 80 countries evolved into a sophisticated data platform that now helps uncover hidden networks facilitating forced labor. Samuel's commitment to transparency goes beyond simple compliance, focusing on the 30% of companies truly willing to "lift up the rocks and see what's underneath" their supply chains. And this inspired me, and hence I invited Samuel to my podcast. We explore the counterintuitive decisions that transform good companies into remarkable ones. His approach challenges the "move fast and break things" mentality that dominates the startup world. Samuel reveals why the hardest business choices often aren't about what to do, but about what to stop doing—especially when everyone around you expects the opposite. We discuss why sometimes you need to step back and work "under the hood" of your business rather than racing forward, and how what seems like an obvious path in the market can often be a "mirage." Throughout our conversation, Samuel shares the moments where slowing down actually accelerated his success and why rebuilding foundations allowed him to capitalize on opportunities his competitors couldn't see. Here is a quote that captures one of Samuel's most striking business lessons:  "If we had not made the decision around the data schema that we made, we would today not be in the position that we're in to leverage the AI technology that's in the market. Frankly, we need to leverage that to keep up with the pace at which things are moving right now." By listening to this podcast you will learn: How to recognize when your business needs to take two steps back to ultimately move ten steps forward Why your first hires post-funding should focus on leverage points rather than immediate revenue generation How implementing "user manuals" for leadership creates vulnerability and clarity that transforms team dynamics How to structure pipeline confidence-weighting systems that prevent optimism bias in your forecasting For more information about the guest from this week:  Samuel Logan  Website: Evidencity.com Learn more about your ad choices. Visit megaphone.fm/adchoices

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