The First Customer

In this episode, I was lucky enough to interview Etienne de Bruin, Founder and CEO of 7CTOs.

Etienne shares his entrepreneurial journey, starting from his upbringing in South Africa to founding his organization that supports technology leaders. Growing up during a time of global isolation for South Africa, Etienne reflects on how this scarcity of resources fostered a strong entrepreneurial spirit and innovative thinking. W...

In this episode, I was lucky enough to interview Rachel Sanders, CEO and Co-Founder of Rootine.

Rachel shares the transformative journey behind her health and wellness brand. Rootine’s mission is to empower individuals with personalized, data-driven health solutions, starting with custom multivitamins tailored to biological data. Rachel recounts how her upbringing in a holistic health-focused household, combined with her e...

In this episode, I was lucky enough to interview Hunter Fortuin and Tom Carmona, co-founders of Wolfjaw Studios. 

Based in Troy, New York, Wolfjaw specializes in backend development for online gaming services, tackling the complex systems that enable matchmaking, account management, and telemetry. Tom recounts how the company’s first major client originated from a network connection cultivated over three years. By focusing...

In this episode, I was lucky enough to interview Jason Barnard, CEO of Kalicube.

Jason recounts his beginnings in the music industry, where he started a record label after failing to secure a deal for his band. This led him to his first customer, a record company, which he gained through relationship building. He further explains the challenges he faced with his second company, a children’s entertainment platform, which ul...

In this episode, I was very, very lucky enough to interview my former boss, Dave Reinhold, Founder of VentureCPO.

Growing up in New York, Dave recounts his first “business” selling bubble gum and fans to classmates, reflecting a lifelong drive for independence and resourcefulness. His early passion for technology blossomed with his first computer, a Commodore 64, which sparked a fascination with digital products. Dave wen...

In this episode, I was lucky enough to interview Deanna Sheward, co-founder and Chief Product Officer of Capablanca.

Deanna shares her unique journey from academia to entrepreneurship. She recounts how her background in art, architecture, and research instilled in her a passion for learning and personal growth, which later fueled her pivot into the tech industry. Deanna explains how the skills she honed as a researcher—lik...

In this episode, I was lucky enough to interview Sean Languedoc, Founder and CEO of Outforce AI.

Sean recounts his unconventional start in business, inspired by advice to "learn by doing" instead of pursuing an MBA. He shares his experience launching a tourism venture during Expo 86 in Vancouver, which taught him the value of adaptability when the business didn’t take off as expected. From there, Sean explored va...

In this episode, I was lucky enough to interview Jordan Saunders, founder and CEO of NextLink Labs.

Jordan reflects on his entrepreneurial journey, starting from his early days in Pittsburgh, Pennsylvania, building computers at age 12. He shares how his passion for technology led him to pursue consulting right out of college after studying computer science at Penn State. Over the past decade, Jordan has grown NextLink Labs...

In this episode, I was lucky enough to interview Alex Levin, Co-Founder and CEO of Regal.io.

Alex grew up in Manhattan with a father who ran a steel service business. Alex absorbed early lessons about business operations and efficiency. While his father’s ventures in technology during the late 90s exposed him to a rapidly changing landscape, Alex initially explored entrepreneurship by selling wild fruit with his brothers a...

In this episode, I was lucky enough to interview Dave Schneider, the CEO of Shortlist.io.

Dave shares his upbringing in Ashland, Massachusetts, a small town where entrepreneurship was not encouraged. He explains how his early life and family background led him toward a more traditional career path, but eventually, after working a corporate job, he shifted to a more nomadic lifestyle with his wife. They started a travel blo...

In this episode, I was lucky enough to interview Dan Balcauski, founder and CPO of Product Tranquility.

Dan shared his backstory, growing up in Chicago with no direct entrepreneurial influences but finding his path through engineering and the software industry. He moved to Austin, Texas, over 20 years ago, drawn by its warmer climate and tech opportunities. Initially influenced by the dot-com bubble, Dan's entrepreneu...

In this episode, I was lucky enough to interview Donnie Boivin, Founder and CEO of Success Champions Network.

Donnie grew up in a blue-collar family, and never considered starting a business until he was in his 40s. Inspired by thought leaders like Gary Vee and Tim Ferriss, Donnie made the leap after spending nearly two decades in sales, but quickly realized that building a successful business was far harder than anticipat...

In this episode, I was lucky enough to interview Baird Hall, co-founder of Churnkey.

Growing up in a family of entrepreneurs, Baird didn’t start his first company until he was 27, though he feels he could have begun earlier. His first venture, a social audio network for sports fans, ultimately failed because while the product had passionate users, it generated no revenue. Baird reflects on how this experience led to his f...

In this episode, I was lucky enough to interview Lynn Whitbeck, Founder and CEO of Petite2Queen.

Lynn grew up in a mid-sized town, and her experience in the Girl Scouts, where she spearheaded a cookie-selling strategy with a shy friend, sparked her love for sales. That early success, along with her passion for helping people, laid the foundation for her sales expertise. Over time, Lynn moved into outside sales after gradua...

In this episode, I was lucky enough to interview Len Covello, CTO and Co-founder of Engage People.

Len discusses his early influences, including growing up in Toronto and being inspired by his father, who was an entrepreneur in the catering business. Len's passion for technology started at a young age with his first computer, a Vic 20, and continued to grow as he developed basic programming skills and built websites ...

In this episode, I was lucky enough to interview Andrew Watson, Co-Founder of Igloo Media.

Andrew recounts his upbringing in Italy and England, and how his initial aspirations as a tennis player eventually led him to entrepreneurship in the U.S. He describes his collegiate tennis career, where he honed his competitive spirit, which later translated into valuable skills in the business world. Andrew emphasizes how the disc...

In this episode, I was lucky enough to interview Sanket Karamchandani, Founder of Miss Neeta's Ice Cream Parlor.

Sanket shared his entrepreneurial journey from a childhood dream inspired by cricket legend Sachin Tendulkar to becoming a business owner. Growing up in the Bay Area, Sanket was driven by the desire to pursue something he loved, which he eventually realized was ice cream. Despite his early aspirations, it ...

In this episode, I was lucky enough to interview a very, very, special friend, Christopher Wink, Co-founder and CEO of Technical.ly.

Chris discussed his upbringing in a rural corner of Northwest New Jersey, which lacked exposure to technology and entrepreneurship. Despite not coming from a family with a background in journalism or entrepreneurship, Chris shared how his parents' traits—his father's ability to talk...

In this episode, I was lucky enough to interview Jeff Bruno, CEO and Co-founder of B.Modelr.

Jeff shares his entrepreneurial journey, which began in Philadelphia, and how his passion for small business finance led him to create his fractional CFO service. However, after realizing the limitations of the service model, Jeff and his partner, Julian Wright, pivoted to focus on building a tech-driven platform using generative ...