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 t...
Mar 05, 2025•23 min•Ep 195•Transcript available on Metacast 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 ...
Feb 26, 2025•23 min•Ep 194•Transcript available on Metacast 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•Ep 193•Transcript available on Metacast 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•Ep 192•Transcript available on Metacast 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 t...
Feb 05, 2025•20 min•Ep 191•Transcript available on Metacast 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•Ep 190•Transcript available on Metacast 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•Ep 189•Transcript available on Metacast 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•Ep 188•Transcript available on Metacast 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•Ep 187•Transcript available on Metacast 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•Ep 186•Transcript available on Metacast 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•Ep 185•Transcript available on Metacast 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•Ep 184•Transcript available on Metacast 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•Ep 183•Transcript available on Metacast 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•Ep 182•Transcript available on Metacast 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 various industries, including commercial real estate and digital media, with...
Nov 13, 2024•25 min•Ep 181•Transcript available on Metacast 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 into a technology consultancy, focusing on custom software development, c...
Nov 06, 2024•23 min•Ep 180•Transcript available on Metacast 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 as a child. After working for another company rather than launching his own...
Oct 30, 2024•21 min•Ep 179•Transcript available on Metacast 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 blog that eventually turned into a client service business, introducing trave...
Oct 23, 2024•27 min•Ep 178•Transcript available on Metacast 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 entrepreneurial dreams took shape later in life, especially after a year-long trip ar...
Oct 16, 2024•26 min•Ep 177•Transcript available on Metacast 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 anticipated. He faced significant challenges, including a crippling non-compete tha...
Oct 09, 2024•23 min•Ep 176•Transcript available on Metacast 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 first success, pivoting to create a tool that allowed podcasters to share au...
Oct 02, 2024•23 min•Ep 175•Transcript available on Metacast 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 graduate school and eventually founded Petite2Queen. Her company focuses on help...
Sep 25, 2024•23 min•Ep 174•Transcript available on Metacast 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 during the early days of the internet. His journey into the tech industry i...
Sep 18, 2024•24 min•Ep 173•Transcript available on Metacast 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 discipline and resilience learned through sports have been instrumental in his ...
Sep 13, 2024•17 min•Ep 172•Transcript available on Metacast 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 took years of preparation, including a career in product management, to set...
Sep 11, 2024•19 min•Ep 171•Transcript available on Metacast 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 to anyone and his mother's love of questions—fostered his interest i...
Sep 09, 2024•34 min•Ep 170•Transcript available on Metacast 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 AI. Their goal is to help small businesses remove ambiguity in their operat...
Sep 06, 2024•25 min•Ep 169•Transcript available on Metacast In this episode, I was lucky enough to interview a very special friend, Jedidiah Weller, the CEO and Founder of Open Forge and Startup Wars. Jedidiah shares his entrepreneurial journey, beginning in rural Pennsylvania, where he grew up in Amish country. He details how his experiences in a challenging upbringing without strong entrepreneurial role models spurred his drive to succeed. After a difficult start in the corporate world and a failed West Coast startup that left him financially strained,...
Sep 04, 2024•34 min•Ep 168•Transcript available on Metacast In this episode, I was lucky enough to interview Jack Adler, CEO and Founder of Out2Win Sports. Jack shares his journey from growing up in Bluebell and Villanova to his time at Syracuse University, where he founded Out2Win Sports in 2021. The idea for his sports marketing firm, which specializes in connecting brands with athlete creators in the NIL (Name, Image, Likeness) space, was born during the COVID-19 pandemic. Jack and his twin sister's successful COVID-19 relief fundraiser ignited h...
Sep 02, 2024•18 min•Ep 167•Transcript available on Metacast In this episode, I was lucky enough to interview Leopold van Oosten, the CEO and Founder of Amsterdam Standard. Leopold recounts his entrepreneurial journey, which began in a small, unremarkable town in the Netherlands. Initially studying hotel management with aspirations of entering the hospitality industry, his path took a dramatic turn during an internship in London in 2001. There, he was exposed to the potential of online services, particularly the burgeoning online ticketing industry. Inspi...
Aug 30, 2024•19 min•Ep 166•Transcript available on Metacast 
