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 com...
Jun 25, 2025•26 min•Season 1Ep. 211
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...
Jun 18, 2025•22 min•Season 1Ep. 210
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 ...
Jun 11, 2025•25 min•Season 1Ep. 209
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 d...
Jun 04, 2025•25 min•Season 1Ep. 208
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 in...
May 28, 2025•30 min•Season 1Ep. 207
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 chi...
May 21, 2025•26 min•Season 1Ep. 206
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 hi...
May 14, 2025•22 min•Season 1Ep. 205
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 te...
May 07, 2025•21 min•Season 1Ep. 204
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 successful...
Apr 30, 2025•21 min•Season 1Ep. 203
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 ...
Apr 23, 2025•25 min•Season 1Ep. 202
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...
Apr 16, 2025•20 min•Season 1Ep. 201
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,...
Apr 09, 2025•23 min•Season 1Ep. 200
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 ca...
Apr 02, 2025•24 min•Season 1Ep. 199
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...
Mar 26, 2025•26 min•Season 1Ep. 198
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 ...
Mar 19, 2025•23 min•Season 1Ep. 197
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 recruit...
Mar 12, 2025•23 min•Season 1Ep. 196
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-pre...
Mar 05, 2025•23 min•Season 1Ep. 195
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 n...
Feb 26, 2025•23 min•Season 1Ep. 194
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 leader...
Feb 19, 2025•19 min•Season 1Ep. 193
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 transitio...
Feb 12, 2025•20 min•Season 1Ep. 192
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 influenc...
Feb 05, 2025•20 min•Season 1Ep. 191
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 ven...
Jan 29, 2025•26 min•Season 1Ep. 190
In this episode, I was lucky enough to interview Brian Glick, CEO and founder of Chain.io Brian traced his inspiration to a family background in leadership and entrepreneurship, coupled with firsthand experience in customs brokerage. Dropping out of college, Brian’s entry into the supply chain world began humbly, crawling under desks to set up computers. Over time, he recognized inefficiencies in the customs and freight industries, which spurred the creation of his first company, Aspect9, and ev...
Jan 22, 2025•21 min•Season 1Ep. 189
In this episode, I was lucky enough to interview Jon Wise, the founder and CEO of Jon Wise Creative (JWC). Jon started his childhood in suburban Atlanta, where his father ran a local software store. Jon recalls his earliest entrepreneurial endeavor at a community festival, selling “Tucker Rocks” to neighbors, which marked the beginning of his creative and business-minded spirit. After studying music in Boston and freelancing in event production, Jon leveraged his burgeoning Instagram presence to...
Jan 15, 2025•22 min•Season 1Ep. 188
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. With a background in computer science and early exposure to personal comput...
Jan 08, 2025•36 min•Season 1Ep. 187
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 experience in investment banking, highlighted the gap between technological...
Dec 18, 2024•23 min•Season 1Ep. 186
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 on honesty, stellar communication, and high technical standards, Wolfjaw h...
Dec 11, 2024•30 min•Season 1Ep. 185
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 ultimately succeeded due to a significant audience demand, evidenced by five...
Dec 04, 2024•23 min•Season 1Ep. 184
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 went on to study management information systems at Binghamton University and e...
Nov 27, 2024•23 min•Season 1Ep. 183
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—like public speaking, project management, and self-promotion—naturally transl...
Nov 20, 2024•24 min•Season 1Ep. 182
