The First Customer

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 Goo...

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 schol...

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 ins...

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...

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 bus...

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. ...

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 h...

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 understandin...

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 i...

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 l...

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 A...

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 h...

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...

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,...

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 pers...

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 late...

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 fin...

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...

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...