The First Customer

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...

In this episode, I was lucky enough to interview Jimmy Jacobson, CTO of Codingscape.

Jimmy discovered programming through his father's university lab computer, unaware it could be a career. He later pursued computer science, freelancing while working at Overstock and Zappos. Zappos’ culture encouraged risk-taking, fueling his entrepreneurial drive. He co-founded Wedgies.com, a social media polling tool with clients like The Wall Street Journal and the White House. Despite its success, venture capital pressures led to its acquisition by Match.com, shaping his approach to future ventures.

After the sale, Jimmy and his partners fo...

In this episode, I was lucky enough to interview Will Blackburn, co-founder of DevClarity.

Will shares he's from Birmingham, Alabama, where he still resides. Although he moved to Atlanta, thinking Birmingham lacked a tech ecosystem, he returned after seeing local success stories and opportunities. Birmingham’s smaller, supportive startup community, centered around the Innovation Depot, made it easier to build connections than Atlanta’s bigger, less personal environment. This supportive community inspired him to build DevClarity in Birmingham.

Will explains that DevClarity helps new engineering managers with a developer-focused one-on-one tool. It uses AI to summ...

In this episode, I was lucky enough to interview Tatsiana Kirimava, CEO and co-founder of Orangesoft.

Tatsiana shares that she grew up in various countries, including Poland, Belarus, and the U.S. She attributes her open-mindedness and independence to her parents, who encouraged her to make her own decisions. She highlights her ability to communicate effectively and build networks as essential skills she honed throughout her life. Her passion for technology from a young age naturally led her to create Orangesoft, which started as a mobile app development company and has now evolved into a specialized custom...

In this episode, I was lucky enough to interview T. Brad Kielinski, Founder of IT Pros.

Brad shared his journey from growing up in Plymouth Meeting near Germantown Academy to becoming a successful tech recruiter in Philadelphia. Inspired by witnessing his uncle and aunt’s homegrown business grow to 400 employees and his father’s inventive spirit, Brad gravitated towards entrepreneurship early on. His career path began with internships in IT and eventually led him to work for various tech recruiting agencies before launching IT Pros in 2011. His approach to building the business included founding a LinkedIn community in 2...

In this episode, I was lucky enough to interview Charles Sims, CEO and founder of Investimate.

Charles shares how he grew up around innovation and leadership inspired him to build and scale ventures, starting with a paintball supply company as a child. His ability to adapt and thrive in chaos earned him the moniker "Hurricane CTO" during his tenure with organizations like the LA Clippers and United Talent Agency, where he became known for troubleshooting crises and bringing stability to high-pressure situations. Now, with Investimate, he is channeling his expertise into a platform that helps founders refine...

In this episode, I was lucky enough to interview David Snider, founder and CEO of Harness Wealth. 

Growing up in Boston, David's early exposure to financial services and an interest in problem-solving shaped his career. After co-founding and helping grow Compass, a major real estate brokerage, he realized that navigating tax and financial complexities was a major challenge for business owners and high-growth employees. His personal experience with a missed tax-saving opportunity underscored the need for better financial advisory services tailored to the next generation of wealth creators. 

David explained the unique challenges of launching a...

In this episode, I was lucky enough to interview Jason Shafton, CEO and founder of Winston Francois.

Jason shares his journey from growing up in a family of entrepreneurs in Chicago to becoming a growth and marketing consultant for tech startups. Inspired by his parents’ business ventures in high-end audio equipment, Jason developed an early passion for business, launching a small airplane-selling stand as a child and later a record label in high school. His career took him from Google to leadership roles at Comedy Central, Headspace, and various startups before organically transitioning into consulting. What began as...

In this episode, I was lucky enough to interview Vladimir Baranov, CEO and founder of Human Interfaces.

Vladimir had early exposure to the turbulent Russian business climate, which made him cautious about entrepreneurship, but his experiences in the U.S. gradually changed his perspective. In college, he created a textbook-sharing platform, an early taste of entrepreneurship, though without charging users. Later, he ventured into finance, spending over a decade in capital markets before transitioning to startups. His first major success came when he co-founded a wealth management tech company, which scaled to 150 employees and was eventually acquired...

In this episode, I was lucky enough to interview Peter Bonney, CEO and founder of Fastbreak RFP.

Peter shares his entrepreneurial journey, starting from his childhood in a small town in Massachusetts. Growing up with a father who ran shoe stores and constantly engaged in side hustles, Peter absorbed key lessons in customer focus and hustle. He reflects on how his early experiences shaped his business philosophy, especially his dad’s mantra, "The customer is your job," which continues to influence how he approaches building customer-centric solutions. Peter’s first venture, Vendorful, taught him hard lessons about the...

In this episode, I was lucky enough to interview Shae Feltz, CEO and founder of NOTICS, an IT service provider based in Minneapolis. 

Shae delves into his humble beginnings in Brainerd, Minnesota, where he learned early on that working for someone else wasn’t for him. At just 16, Shae launched a mobile iPhone repair business, gaining valuable insights into marketing, sales, and fulfillment. He credits his early experiences with shaping his approach to business, including the sale of his first venture’s client list and inventory. Through a combination of technical skill, hands-on problem-solving, and taking advantage of pr...