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 1...
May 07, 2025•53 min•Season 8Ep. 360
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 soluti...
Apr 30, 2025•48 min•Season 8Ep. 359
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...
Apr 23, 2025•51 min•Season 8Ep. 358
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 signi...
Apr 16, 2025•1 hr•Season 8Ep. 357
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 an...
Apr 02, 2025•51 min•Season 8Ep. 356
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 ...
Mar 26, 2025•46 min•Season 8Ep. 355
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...
Mar 19, 2025•58 min•Season 8Ep. 354
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...
Mar 12, 2025•50 min•Season 8Ep. 353
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 buil...
Mar 05, 2025•55 min•Season 8Ep. 352
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 d...
Feb 26, 2025•50 min•Season 8Ep. 351
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. ...
Feb 19, 2025•55 min•Season 8Ep. 346
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 m...
Feb 12, 2025•41 min•Season 8Ep. 349
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 cli...
Feb 05, 2025•50 min•Season 8Ep. 348
This podcast interview focuses on the entrepreneurial journey to make buying and selling in B2B remarkably easier. My guest is Mark Fershteyn, Founder and CEO of Recapped. Mark is a tech entrepreneur on a mission. He has a passion for building things from scratch. He specifically prefers going from "zero to one" rather than maintaining existing systems, describing himself as someone who enjoys "bushwhacking through the jungle" and forging new trails. His entrepreneurial journey includes diverse ...
Jan 29, 2025•46 min•Season 8Ep. 347
This podcast interview focuses on the entrepreneurial journey to successfully merge and integrate two distinct SaaS companies while balancing stakeholder interests, maintaining growth, and navigating complex market dynamics. My guest is Randy Wootton, CEO of Maxio. Randy is a serial CEO. Before becoming CEO, he held senior positions at industry giants like Microsoft and Salesforce, where he led sales, service, and marketing teams. His career has given him a truly global outlook. He has worked in...
Jan 22, 2025•46 min•Season 8Ep. 346
This podcast interview focuses on the entrepreneurial journey to democratize customer evidence and change the way B2B software buying decisions are made. My guest is Evan Huck, Co-founder and CEO of UserEvidence. Evan's journey in the tech industry is a testament to his entrepreneurial spirit and sales acumen. He started his career as an SDR (Sales Development Representative) in 2010, joining TechValidate as their first sales employee. This early experience laid the foundation for his future suc...
Jan 15, 2025•55 min•Season 8Ep. 345
This podcast interview focuses on the challenges and strategies of implementing product-led growth (PLG) effectively (and when to stay out of PLG). My guest is Wes Bush, product-led growth pioneer, founder of Productled.com, and bestselling author. Wes is widely recognized as one of the pioneers of the product-led growth movement, challenging an entire industry to rethink their approach to SaaS growth. In 2016, he introduced a freemium product at Vidyard that gained over 100,000 users in less th...
Jan 08, 2025•46 min•Season 8Ep. 344
This podcast interview focuses on the entrepreneurial journey to build a global SaaS company with 25 million users without venture funding. My guest is Aytekin Tank, Founder and CEO of Jotform. Aytekin founded Jotform in 2006, creating a pioneering WYSIWYG online form builder that has grown to serve over 25 million users worldwide today. What's remarkable is that he bootstrapped the company from the ground up. This allowed Jotform to remain 100% independent and define its own rules and company c...
Dec 18, 2024•59 min•Season 7Ep. 343
This podcast interview focuses on the entrepreneurial journey to eliminate the risk that cost businesses thousands of $ per second of downtime. My guest is Ozan Unlu, Founder and CEO of Edge Delta. Ozan has had an unconventional career path that spans multiple disciplines. He started as a nanoscientist and researcher before transitioning into the tech world. His professional journey includes roles at major tech companies. He worked as a Software Development Lead and Program Manager at Microsoft,...
Dec 11, 2024•51 min•Season 7Ep. 342
This podcast interview focuses on the entrepreneurial journey to redefine software's role from engagement-driven to impact-driven solutions. My guest is Daniel Saks, CEO of Landbase. Daniel's entrepreneurial journey has deep roots in a 100-year-old family business. He grew up in Niagara Falls, Canada, where his family owned a furniture store founded by his great-great-grandparents in 1908. However, the 2009 recession forced the century-old family business to close, which became a pivotal moment ...
Dec 06, 2024•57 min•Season 7Ep. 341
This podcast interview focuses on the entrepreneurial journey to transform toxic sales automation. My guest is Mark Kosoglow, CEO of Operator. Mark is a tech entrepreneur on a mission. A big mission. He's a sales expert who played a crucial role in helping scale Outreach from zero to over $230 million in revenue in just 8-years. Being part of the rising growth of sales automation, Mark realizes how too much automation and the mantra of Growth at all Costs has wrecked outbound. It's created a mas...
Nov 27, 2024•42 min•Season 7Ep. 340
This podcast interview focuses on the entrepreneurial journey to build mission-critical billing infrastructure for complex B2B SaaS pricing models. My guest is Griffin Parry, Founder and CEO of m3ter. Griffin Parry is a serial Entrepreneur. In 2013, he founded GameSparks, a backend-as-a-service platform for video games, which he sold to Amazon in 2017. Combining his firsthand experience with the challenges of usage-based pricing at GameSparks with the problems he encountered at a much larger sca...
Nov 20, 2024•50 min•Season 7Ep. 339
This podcast interview focuses on the entrepreneurial journey to change the way healthcare nurses can work to improve patient safety. My guest is Hadassah Backman, CEO of Guardoc Health. Hadassah has nursing roots: She started her career as a registered nurse and has built hands-on experience in emergency room and hospice care. This clinical background gives her unique insights into the challenges faced by frontline healthcare workers. Besides that, she holds a master's degree in public health p...
Nov 13, 2024•48 min•Season 7Ep. 335
This podcast interview focuses on the entrepreneurial journey to build deep vertical business solutions that deliver 10x value for every 1x in price charged. My guest is Dan Uyemura, CEO of Pushpress. Dan has had an entrepreneurial spirit from a young age. He was a Dot-com era pioneer: During college, he founded Mixture.com, a platform that was ahead of its time and preceded social media giants like Myspace. After working in tech, including a stint at Myspace, he made a dramatic career pivot by ...
Nov 06, 2024•48 min•Season 7Ep. 337
This podcast interview focuses on the entrepreneurial journey to democratize political data and anticipate regulatory changes. My guest is Victor Kristof, Co-founder and CEO of DemoSquare. Victor is a fascinating individual with a unique blend of academic excellence, entrepreneurial spirit, and a passion for leveraging technology to enhance democratic processes. He holds a Ph.D. in Machine Learning from Ecole Polytechnique Federale de Lausanne, where he developed algorithms and statistical model...
Oct 30, 2024•43 min•Season 7Ep. 336
This podcast interview focuses on the entrepreneurial journey to help all of us to have conversations that drive action and meaningful connections. My guest is Joaquim Lecha, CEO of Typeform. Joaquim (Kim) is a tech entrepreneur on a big mission, bringing over 20 years of experience in high-growth companies. He started his career in M&A, strategy, and financial advisory. In 2012 he joined the tech world as the CFO of Socialpoint, a world-renowned mobile game developer, later taking on the role o...
Oct 23, 2024•55 min•Season 7Ep. 335
This podcast interview focuses on the entrepreneurial journey to build a successful bootstrapped SaaS company in the highly competitive scheduling software market. My guest is Bridget Harris, Co-founder and CEO of You Can Book Me. Bridget has had three distinct careers, showcasing her versatility and adaptability: She started in the television and film industry. Then, transitioned to politics, serving as a political advisor focusing on constitutional reform and the House of Lords. Her political ...
Oct 16, 2024•46 min•Season 7Ep. 334
This podcast interview focuses on the entrepreneurial journey from the last 5 years to turn Plum into the best Talent Intelligence solution on the market. My guest is Caitlin MacGregor, Co-Founder and CEO of Plum Caitlin MacGregor co-founded Plum in 2012 and has been an earlier guest on my podcast (#54 in February 2019). She was voted "most likely to save the world" in her high school yearbook, foreshadowing her future as an innovative entrepreneur. Before founding Plum, Caitlin built two other ...
Oct 09, 2024•56 min•Season 7Ep. 333
This podcast interview focuses on the entrepreneurial journey to make complex code understandable for business leaders. My guest is Matt Van Itallie, Founder and CEO of Sema. Matt has a diverse background spanning law, consulting, education, and tech, and he has held leadership roles at edtech and govtech companies like Social Solutions, and PeopleAdmin. He earned his J.D. from Harvard Law School after studying history at Swarthmore College. He's also a thought leader on the impact and responsib...
Oct 02, 2024•50 min•Season 7Ep. 332
This podcast interview focuses on the entrepreneurial journey to drive change and adapt as a B2B marketer in an evolving business landscape. My guest is Christian Klepp, Co-Founder of EINBLICK Consulting and Host of the B2B Marketers on a Mission podcast. Christian is a global citizen, entrepreneur, podcast host, and B2B branding expert with over 13 years of experience across diverse markets. Throughout his career, he worked with major global brands like Philips, Caterpillar, Samsung, and Logite...
Sep 25, 2024•46 min•Season 7Ep. 331
