The First Customer

In this episode, I was lucky enough to interview Carl Gould, co-founder and CTO of Inductive Automation.

Growing up in California’s Bay Area during the rise of the modern internet, Carl developed an early fascination with computers that eventually led him to study computer science at UC Davis. What began as a summer project connecting industrial machine data to SQL databases soon evolved into a full software platform used by engineers around the world to build applications that monitor and control factories, water systems, and other industrial operations.

Carl shares the story behind Inductive Au...

In this episode, I was lucky enough to interview Matt Cullerton, founder of Mavric Tech and creator of Apso. 

Matt reflects on growing up in Reston, Virginia, early lessons from working in restaurants, and his first venture — an independent music label launched while working at Northrop Grumman. From navigating the volatility of the music industry — including brushes with artists like Diplo — Matt shares how those formative experiences shaped his resilience and people-first mindset.

Matt also discusses his philosophy of fairness in leadership, particularly within development teams, and how core values serve as operational anchors in a clien...

In this episode, I was lucky enough to interview with Dan Goldsmith, co-founder and chairman of Tendo and co-founder of Proofpoint Capital. 

Dan shares stories from his Philadelphia roots, the early formation of his grit, and the mindset that has guided his career — from running a mobile DJ business in high school to building and scaling multiple technology companies. He offers a thoughtful perspective on perseverance, explaining how deep obsession with a problem can fuel success, while also highlighting the risks of letting conviction turn into blind spots.

Dan delves into Tendo’s mission to moder...

In this episode,  I was lucky enough to interview Joel Reed, CEO and founder of Open Arc.

Joel starts to unpack the long, nonlinear journey of building a software consulting company that’s lasted more than 20 years. Joel shares how a career plateau, the 2008 financial crisis, and a humbling professional low point ultimately pushed him to start Open Arc. From working four 10-hour days to fund the business on the side, to landing their very first customer through trusted relationships, Joel reflects on how resilience, timing, and people-first decision-making shaped the company’s foundation.

Joel dives...

In this episode, I was lucky enough to interview Calvin Hendryx-Parker, CTO and co-founder of Six Feet Up.

Calvin shares the origin story behind Six Feet Up’s unforgettable name—drawn from his family’s mortuary business—and how servant leadership, community involvement, and trust became foundational principles for building a durable software consultancy. From hosting websites on a literal coffee-table server in a San Francisco apartment to becoming an AWS Hero and Tech Executive of the Year, Calvin’s story is anything but conventional.

Calvin delves into community-driven growth, long-tail relationship sales, and why he believe...

In this episode, I was lucky enough to interview Bill Near, Founder and CEO of Helios, a performance wearable helping hockey players and teams improve faster through motion-based data and video integration.

Bill breaks down Helios’ first-principles approach to avoiding “tech fatigue” by delivering recurring, practical value—most notably through time-saving video workflows and emerging AI-driven coaching insights that turn raw data into actionable development guidance for players and parents alike.

Bill also shares the personal and technical journey behind Helios, from growing up playing hockey in New Hampshire to studying engineering at MIT and recogniz...

In this episode, I was lucky enough to interview Ole Lensmar, co-founder and CTO of Testkube.

Ole shares his unique perspective growing up across Germany, the US, and Sweden, and how those experiences shaped his adaptability and approach to entrepreneurship. He reflects on the differences between launching tech startups in Europe versus the United States, and why he believes the US remains a more mature market for scaling innovation. From his first ventures in the mid-90s to the creation of SoapUI, Ole explains how his passion for coding and solving practical problems led him to build...

In this episode, I was lucky enough to interview Det Ansinn, the founder of Brick Simple LLC, serial entrepreneur with four successful exits, and current CEO of MedTech company Neuralert. 

Det shares his journey from pumping gas at the Doylestown Airport to building multiple innovative ventures, emphasizing the value of authentic connections, strong team culture, and pursuing projects that excite him over purely profit-driven motives. From creating Brick Simple’s first product to developing apps for Xbox Live and navigating the post-dot-com era, Det reflects on how his experiences shaped his approach to entrepreneurship and leadership.

In this episode, I was lucky enough to interview Chris Molaro, CEO and co-founder of NeuroFlow. 

Chris unpacks the personal and professional journey that takes him from growing up in Queens and Long Island to serving as an Army officer and ultimately building a healthcare technology company. Chris shares how the events of 9/11, his experience at West Point, and years of active-duty service shape his leadership philosophy and resilience. He reflects on his transition from military to civilian life, emphasizes the importance of “running toward something, not away from something,” and explains how lessons from combat—especially maintai...

In this episode, I was lucky enough to interview the legendary sales expert and bestselling author Jeb Blount.

Jeb shares stories from his upbringing in small-town Georgia, where being the smallest kid in school taught him grit, hustle, and the relentless work ethic that would later define his career. He talks about finding confidence through public speaking, his early ambition to become a lawyer, and the surprising moment—thanks to “Rudy” himself—that pushed him to write his first book and eventually build Sales Gravy into a powerhouse sales training company.

Jeb also breaks down how elit...

In this episode, I was lucky enough to interview Joel Montvelisky, co-founder and Chief Product Officer of PractiTest.

Joel shares his unlikely journey from Costa Rica to the world of software testing. He talks about becoming a Cowboys fan in the 1970s, stumbling into QA because it paid slightly better than bartending, and eventually discovering that testing was far more than bug hunting—it was about improving products, reducing risk, and helping teams release with confidence. He reflects on the evolution of QA from the dot-com era to modern Agile and DevOps practices, the absence of formal QA...

In this episode, I was lucky enough to interview Andy Kochanowski, founder and CEO of Alerify, a data center based in Harrisburg, Pennsylvania.

Andy shares his journey from a 30-year career in corporate America, including service in the Navy, to taking the leap into entrepreneurship. He explains how Alerify serves a niche market of small and medium-sized businesses seeking secure, localized data storage through co-location and virtual private cloud solutions, providing a personal, hands-on approach that sets them apart from the hyperscale public cloud providers.

Andy also dives into the process of acquiring and revitalizing...

In this episode, I was lucky enough to interview Sean Heberling, founder and CEO of Marion Street Capital.

From buying up newspaper routes as a kid in Rochester, New York, to hiring friends and building a mini “paperboy empire,” Sean’s early ventures taught him how to scale, manage people, and spot opportunity. Those same instincts followed him through a 20-year career in hedge funds and later into academia as a finance professor at Villanova University, where he rediscovered his passion for helping businesses grow from the ground up.

Sean explains how Marion Street Capital was bo...

In this episode, I was lucky enough to interview Adam Holt, founder and CEO of Asset-Map.

Adam talks about how his entrepreneurial drive took shape from his early years in New York to leading one of the most innovative platforms in financial visualization. Adam shares how his mother’s example as a self-made realtor influenced his approach to business and connection, teaching him to treat every interaction as a chance to form genuine relationships. He reflects on how attending Tony Robbins seminars as a teenager opened his mind to the power of mindset, reframing, and fear-breaking—lessons that...

In this episode, I was lucky enough to interview Joshua Davidson, CEO and founder of Chop Dawg.

Growing up just outside of Atlantic City during the Great Recession, Josh saw firsthand how fragile traditional industries could be. Watching friends’ families lose homes and his father work multiple jobs gave him a survival instinct and a drive to create opportunities for himself. By the time he was a teenager, Josh was building websites door-to-door and helping small businesses grow, even in the middle of an economic downturn. That early tenacity and optimism became the foundation of what would ev...

In this episode, I was lucky enough to interview Rob Wenger, CEO and founder of Higher Logic.

Rob shares how Higher Logic evolved from a LinkedIn-style networking idea into a powerful engagement platform serving over 3,000 clients worldwide. With a focus on professional communities—ranging from doctors and accountants to global corporations—Rob explains how the right mix of purpose, participation, and leadership can shape thriving ecosystems that deliver real value for members and organizations alike.

Rob also reflects on his 17-year journey growing Higher Logic, offering insights into what makes communities flourish—or fade. From discov...

In this episode, I was lucky enough to interview Tim Haak, founder and Vice President of Innovation at Mile6. 

Tim shares how growing up in a small-town family business shaped his entrepreneurial mindset, and how his curiosity for technology led him to build his first websites as a teenager—before he even had his driver’s license. From those humble beginnings to leading a digital product agency that has reinvented itself every few years, Tim reflects on the persistence and adaptability needed to stay relevant in an ever-changing industry.

Tim also dives into Mile6’s evoluti...

In this episode, I was lucky enough to interview Marco Benitez, CEO and founder of ROOK, a company revolutionizing how wearable health data is integrated and used.

Marco opens up about his entrepreneurial journey, from growing up in Mexico to moving his family to the U.S. to pursue bigger opportunities. He reflects on how his first startup shaped his path, how COVID-19 became the catalyst for ROOK’s pivot, and the game-changing moment when their very first insurance client validated their API solution.

Marco shares how Rook enables insurance companies, digital health platforms, and re...

In this episode, I was lucky enough to interview Umair Khan, CEO and founder of Techamana.

Umair explains that Techamana is a vetted talent marketplace designed to stand apart from traditional freelance platforms. Techamana ensures quality by rigorously evaluating technical skills, communication, and cultural fit before admitting freelancers to the platform. He explains that the company matches clients with top candidates within 48 hours, delivering a faster and more reliable hiring experience. Umair also addresses challenges such as detecting fraud, upholding quality control, and building trust when connecting global talent with businesses. 

Umair also shares his p...

In this episode, I was lucky enough to interview Melissa Sherman, founding CEO of MOBILion Systems, Inc.

Melissa shares how her Midwestern upbringing and early career at DuPont shaped her blend of science and business acumen, transforming her from a researcher into a CEO. She talks about discovering her passion for building businesses around complex technology, drawing on experiences ranging from textiles and fashion to investment and startup incubation. 

Melissa dives into MOBILion’s mission to “reveal what others leave unseen” through advanced instruments that push the boundaries of measurement and analysis. Melissa explains how their t...

In this episode, I was lucky enough to interview Dan Abel Jr., the Chief Chocolate Officer of Bissinger’s Chocolate.

Dan shares how his family grew up immersed in the candy business—starting from a small family-run operation in 1981 to acquiring and leading the iconic Bissinger’s brand today. Dan walks us through their unique family dynamic, how each sibling found their place in the business, and what it’s really like behind the scenes of a chocolate kitchen—from caramel science to flavor innovation and why making candy is as much art as it is chemistry.

D...

In this episode, I was lucky enough to interview Adam Dakin, President and CEO of Keriton.

Adam’s entrepreneurial journey starts with selling hats and t-shirts in college before building multiple venture-backed startups and leading health tech investments at DreamIt Ventures. When Keriton’s investors seek new leadership, Adam steps in with a plan to stabilize finances, restructure the team, bring sales and marketing in-house, and close key enterprise healthcare deals. His approach pays off, securing major wins like a 32-hospital Intermountain Healthcare partnership that doubles the company’s size. Adam reflects on the challenges of selling into c...

In this episode, I was lucky enough to interview Paul Byrne, President of Razoyo, a Texas-based custom software development company. 

Paul shared how growing up in an entrepreneurial family in Wichita, Kansas—where his mom ran a fabric shop and his dad tinkered with tech ventures—planted the seeds for his own journey. We discussed how the concept of entrepreneurship has evolved from packing circuit boards around kitchen tables to building viral businesses on TikTok, like his daughter recently did. Paul also highlighted how today's lower barriers to entry create exciting possibilities for aspiring founders, especially those balan...

In this episode, I was lucky enough to interview Nicky Senyard, CEO and founder of Fintel Connect. 

Nicky shared the journey behind Fintel Connect—a digital acquisition platform that helps financial institutions across North America grow their customer base through affiliate marketing. She explained how the platform acts like the “plumbing” between banks and publishers like NerdWallet or Credit Karma, using a CPA (cost-per-acquisition) model that rewards performance and delivers real value.

Nicky also opened up about her roots in Australia and how the country's rugged environment shaped her entrepreneurial resilience. Before Fintel, she built and suc...

In this episode, I was lucky enough to interview serial entrepreneur Eric McHugh once again!

Eric dives into his latest venture, dataing.io, an AI-powered matchmaking app built to challenge the typical swipe-based dating model. He shares how the Web3 space supports his builder mindset and leads to the creation of Hold On Labs, a platform that launches products focused on meaningful connection. With dating.io, the goal is to create intentional, high-quality matches using AI-generated personality tags based on users’ social media and digital activity. Unlike Tinder or Hinge, which aim to keep users engaged and sw...

In this episode, I was lucky enough to interview Keilian Knudsen and Prags Mugunthan, co-founders of Pangea.ai. 

Keilian and Prags explored their journey from university roommates in Scotland to building a global tech talent platform. Keilian described how growing up in Switzerland with an American mother and Norwegian father gave him a multicultural view of the world and a drive to create something of his own. Prags shared how moving from Sri Lanka to Norway at a young age gave him access to education and opportunity, which shaped his path toward entrepreneurship. Their first ventures included a...

In this episode, I was lucky enough to interview Aubrey Amatelli, Founder and CEO of PayRio—the first payment provider focused exclusively on alternative medicine.

Aubrey shared how her roots in Silicon Valley and a traditional finance career at JP Morgan eventually led her to launch PayRio, combining her passion for cannabis and her expertise in payments. She walked me through the complicated regulatory landscape that makes payment processing for cannabis so challenging and explained how PayRio uses creative, compliant workarounds like ATM rails and wallet tech to support dispensaries and e-commerce businesses.

Aubrey also op...

In this episode, I was lucky enough to interview Ben Fellows, CEO and founder of Loop QA.

Ben shares how his company addresses the growing need for highly skilled, mid-to-senior QA professionals in a market lacking structured training and clear entry paths. Loop QA focuses on embedding experienced testers directly into teams at startups and enterprises, filling a critical talent gap with candidates who bring technical expertise, product understanding, and emotional intelligence. Ben explains how many successful QA professionals arrive from unconventional paths—often self-taught or transitioning from roles in development or customer success—and highlights the indu...

In this episode , I was lucky enough to interview Bill Douglas, CEO of Optic Wise, also known as “The Resilience Guy”.

From buying his first car at 15 with money he made running a newspaper hustle, to surviving a coral snake bite and a paralyzing ski accident 30 years to the day later, Bill’s journey is a lesson in grit and perspective. He shares how these life-altering experiences pushed him to leave corporate life behind and embrace entrepreneurship, prioritizing fulfillment over financial comfort. He has literally faced death more than once and came out swinging, bringing both wisdom and hu...

In this episode, I was lucky enough to interview Steven Webster, CEO of asensei.

Steven reflects on the importance of learning through iteration. He shares how some of the company's earlier choices—while later adjusted—were necessary stepping stones that shaped their current success. Rather than dwell on what could have been done differently, Steven focuses on how each decision sharpened their perspective and helped them build what he confidently calls the best solution in the market today. It’s a reminder that progress often comes from navigating uncertainty with curiosity and humility.

Steven also unpack...

In this episode, I was lucky  enough to  interview a longtime friend and startup expert Gregory Shepard.

Greg shares the story behind his new book, The Startup Lifecycle, which grew out of a four-year research project on why startups fail. With thousands of transcripts and 200,000 case studies, he saw the need to turn complex data into practical tools for founders. What began as a policy-focused effort became a mission to empower entrepreneurs. This led to both the book and his platform, Startup Science, now home to tens of thousands of founders and a growing network of...

In this episode, I was lucky enough to interview Terence Bennett, CEO of DreamFactory.

Terence shares his unconventional journey from a military intelligence officer to leading a developer-focused API company.  He explains how his entrepreneurial parents influenced his mindset and how his military background taught him to solve problems creatively. He also shares how dealing with dyslexia and joining a support group at Google helped him discover his strength in thinking outside the box. 

Terence discusses his career pivot from cybersecurity to startup life, eventually landing at DreamFactory through his work with the parent company Xe...

In this episode, I was lucky enough to interview James Griffin, CEO of Invene.

James shares how he transitioned from a self-taught coder with early entrepreneurial tendencies to leading a successful healthcare-focused software firm. Raised in an engineering-driven household in McKinney, Texas, James initially pursued biomedical engineering before shifting to computer science, eventually leveraging a full-ride college scholarship to start several ventures. His turning point came after a mentor introduced him to a company needing software support—leading to his first $10,000 consulting client. While balancing this opportunity with a struggling product startup, James leaned into healthcare after di...

In this episode, I was lucky enough to interview Jason Vego, co-founder and CEO of Bevz, a digital platform helping mom-and-pop liquor and convenience stores go online and manage inventory. 

Jason shares how growing up with an entrepreneurial father planted the seed for his own ventures, including an early attempt to build software for dog groomers. The failure taught him valuable lessons about understanding an industry from the inside. That insight became crucial when launching Bevz with his childhood friend—who happened to own multiple liquor stores. Together, they identified a major gap in tech support for sma...

In this episode, I was lucky enough to interview Brett Tiagwad, founder and CEO of Elevated Angles.

Brett shares his unconventional path from finance to drone media. After a challenging personal journey, including recovery and the loss of his mother, Brett found solace and inspiration in flying drones. What started as a therapeutic hobby quickly became a business idea when he realized the visual impact drone footage could have. With no prior experience in photography or videography, he taught himself editing through YouTube, gradually transforming Elevated Angles from a side hustle into a thriving creative production company.<...

In this episode, I was lucky enough to interview Christian Espinosa, founder and CEO of Blue Goat Cyber.

Christian shares his experience of growing up in poverty with an unstable home life, seeking structure in the Air Force, and eventually transitioning from a successful freelancing career to launching his first company, Alpine Security. Christian explains that boredom and the desire for growth pushed him to scale his business, which involved convincing long-time clients to trust his growing team. Despite early challenges, he successfully built and sold Alpine to Cerberus Sentinel during the pandemic—a decision driven by bu...

In this episode, I was lucky enough to interview Dori Yona, Co-founder and CEO of Simple Closure.

Dori shares his entrepreneurial journey, which began with a childhood influenced by his entrepreneur parents and a deep connection to Silicon Valley. He first launched a dating app in Israel, but quickly pivoted to create Earny, a consumer fintech company that automated price protection refunds from retailers and credit card companies. The idea sparked from a real-life experience where he successfully claimed a refund after a price drop, revealing a broader market opportunity. Earny eventually scaled to millions of users...

In this episode, I was lucky enough to interview Mark Wormgoor, CEO and tech coach at The Maverick CTO.

Mark shares that despite a successful 25-year corporate career in IT, he felt unfulfilled after reaching his long-term goal early and ultimately chose to go independent. He candidly reflects on the decision-making process behind leaving corporate life, his early startup missteps, and how a failed venture with a co-founder taught him valuable lessons about product-market fit. His initial foray into entrepreneurship eventually led to launching a software development agency and later, a coaching practice focused on tech leadership.<...

In this episode, I was lucky enough to interview Bert TerHart, CEO and Founder of LeadBrain AI. 

Bert shares how his upbringing in a small Canadian town and the work ethic of his entrepreneurial father shaped his approach to business. From surveying frozen land with his dad on holidays to founding three companies in the tech and healthcare sectors, Bert emphasizes the importance of deep customer commitment and understanding your niche. He recounts his journey from System Modal Software to NextGen SEO, and now LeadBrain AI—each venture building on a foundation of domain knowledge and strong cli...

In this episode, I was lucky enough to interview Bridgette Ferraro, CEO of iCopy Legal.

Bridgette shares her unexpected journey from studying human services at Purdue to leading a legal document retrieval company. She recounts how a bold consulting pitch turned into a long-term leadership role, where she embraced the challenge of scaling a traditional, service-first business into a tech-enabled powerhouse. Bridgette emphasizes the importance of asking questions, understanding internal processes, and empowering her team through thoughtful operational changes like an extra week off.

Bridgette also reflects on building her personal brand alongside iCopy’s ev...