The First Customer

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...

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 eventually Chain.io. Unlike theoretical business plans, Chain.io was born out of real-world pain points and aimed to sim...

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 land significant opportunities, including a project with Ralph Lauren. These experiences culminated in the founding of JWC, where Jon brings a uni...

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 computing, he developed a passion for technology and creativity, which later evolved into a career in tech startups. His experiences working in...

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 innovation in healthcare and the stagnant state of the supplement industry. This realization inspired her to leverage technology and science to address burnout and health challenges through nutrition an...

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 has become a trusted partner for major studios, even receiving word-of-mouth referrals for being "the best in the business."

The duo also shares ins...

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 million monthly visitors to their website. This success attracted the attention of major telecoms like Orange in...

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 earned an MBA in entrepreneurship and MIS from NYU’s Stern School. He built a career around startups, notably working at Loeb as a f...

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 translated into entrepreneurial success. However, she emphasizes the challenge of building a new professional network from scratch after shifting from academia to technology. By a...

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 each venture teaching him new lessons about scaling, market fit, and the importance of pivoting when initial strategies faced ch...

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, cloud infrastructure, and cybersecurity. He discusses the importance of balancing personal time and professional goals, emphasizing the challenges of transitioning from...

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 software business a decade ago, Alex finally co-founded Regal.io, a business focused on improving cu...

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 travel bloggers to agencies in exchange for commissions. This business experience laid the groundwork for his ventures into...

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 around the world. This travel period helped him realize it was the right time to start his own company, leading to the...

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 that nearly caused him to lose everything. Through resilience and with the support of his wife, Donnie turned...

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 audio clips on social media. This pivot eventually grew into a seven-figure business, followed by...

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 helping business owners develop winning sales strategies, particularly by understanding their clients' "why" and building...

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 involved transitioning from professional services to building a product-focused business. Engage People was born out...

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 approach to business, particularly in setting high standards and maintaining a competitive edge.

Andrew also delves into...

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 the stage for launching his business during the COVID-19 pandemic. He began by experimenting with flavors and going...

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 in journalism. His journey into journalism began unexpectedly during his time at Temple University, where he was introduced to the college news...

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 operations by providing a clear process to identify and focus on value-driving activities within their business models. This...

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, Jedidiah co-founded a successful digital agency called Webjunto, which eventually evolved into Open Forge. This transformation marked a...