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 Science, now home to tens of thousands of founders and a growing network of mentors and investors.

Greg also shares his startup-style approach to writing and publishing the book. He carefully planned its structure, from parts and chapters to quotes, jokes, and stories, aiming to make it both informative and engaging. He talks about using AI as a helpful editor, while warning against depending on it for original ideas. Greg also outlines his go-to-market strategy, which includes over 700 tactics across podcasts, book clubs, search optimization, and more.

Give it up one more time for Gregory Shepard! By treating the book like a product launch, his entrepreneurial mindset shines through, showing that even in authorship, he's all in on impact and execution!

Guest Info:
Gregory Shepard's Website
https://www.gregoryshepard.com/

Gregory Shepard's LinkedIn
https://www.linkedin.com/in/gregshepard/

Connect with Jay on LinkedIn
https://www.linkedin.com/in/jayaigner/
The First Customer Youtube Channel
https://www.youtube.com/@thefirstcustomerpodcast
The First Customer podcast website
https://www.firstcustomerpodcast.com
Follow The First Customer on LinkedIn
http://www.linkedin.com/company/the-first-customer-podcast/

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 discusses his career pivot from cybersecurity to startup life, eventually landing at DreamFactory through his work with the parent company Xenon. He explains how DreamFactory’s way of handling APIs, by focusing on data models first, is different and works well, especially for older systems in places like the public sector. He also shares how working with the long-established company Saint-Gobain showed him how much people believe in DreamFactory.

Buckle up for a ride to the Golden State, where Terence shares how strong leadership, trust, and community fuel both personal growth and business success in this episode of The First Customer!

Guest Info:
DreamFactory Software
http://www.dreamfactory.com

Terence Bennett's LinkedIn
https://www.linkedin.com/in/terencehbennett/

Connect with Jay on LinkedIn
https://www.linkedin.com/in/jayaigner/
The First Customer Youtube Channel
https://www.youtube.com/@thefirstcustomerpodcast
The First Customer podcast website
https://www.firstcustomerpodcast.com
Follow The First Customer on LinkedIn
http://www.linkedin.com/company/the-first-customer-podcast/

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 discovering it was the most responsive and financially viable industry, allowing him to bootstrap Invene.

Throughout the conversation, James emphasizes the importance of focus and specialization. He candidly advises agency owners to stop being indecisive and commit to a niche, explaining how his early decision to focus solely on healthcare unlocked higher value clients and stronger referrals. Drawing from his own experience and conversations with other agency founders, James outlines a three-pronged framework for specialization: choosing what energizes you, what motivates your team, and what generates the most profit.

Let's crack the code and uncover James Griffins' unstoppable mindset in this episode of The First Customer!


Guest Info:
Invene
http://www.invene.com

James Griffin's LinkedIn
http://linkedin.com/in/jamesgriffin3/

Connect with Jay on LinkedIn
https://www.linkedin.com/in/jayaigner/
The First Customer Youtube Channel
https://www.youtube.com/@thefirstcustomerpodcast
The First Customer podcast website
https://www.firstcustomerpodcast.com
Follow The First Customer on LinkedIn
http://www.linkedin.com/company/the-first-customer-podcast/

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 small, independent retailers in this space.

Jason explains how Bevz evolved from a DoorDash-style marketplace into a more comprehensive inventory and sales management platform tailored for small convenience stores. While the ultimate goal is full automation of ordering and stock tracking, early adoption hinged on solving what store owners cared about most: increasing revenue through online sales. With over 700 stores on board and a clear focus on serving the underrepresented independent retailer, Bevz is chipping away at a multibillion-dollar problem.

Let’s hear from Jason Vego on why he’s prioritized real-world impact over personal branding—and how listening to customers (not just one savvy co-founder) helped shape their strategy in this episode of The First Customer!

Guest Info:
Bevz
https://bevz.com/


Jason Vego's LinkedIn
https://www.linkedin.com/in/jvego/

Connect with Jay on LinkedIn
https://www.linkedin.com/in/jayaigner/
The First Customer Youtube Channel
https://www.youtube.com/@thefirstcustomerpodcast
The First Customer podcast website
https://www.firstcustomerpodcast.com
Follow The First Customer on LinkedIn
http://www.linkedin.com/company/the-first-customer-podcast/

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.

Brett details the early struggles of breaking into industries like construction and public sector work, where initial expectations didn’t match market realities. After experimenting with different niches, he leaned into his strengths in visual storytelling and editing, positioning his company as a drone-focused media agency catering to brands that value high-quality content. Now expanding his team to meet growing demand, Brett emphasizes the importance of owning your local market and scaling with purpose.

Join Brett Tiagwad on his journey as he highlights the power of persistence, adaptability, and building a brand rooted in both passion and skill in this episode of The First Customer!


Guest Info:

Elevated Angles LLC
https://www.elevatedanglesllc.com/

Email
info@elevatedangles.com

Brett Tiagwad's LinkedIn
https://www.linkedin.com/in/brett-tiagwad-a9a23b79/

Connect with Jay on LinkedIn
https://www.linkedin.com/in/jayaigner/
The First Customer Youtube Channel
https://www.youtube.com/@thefirstcustomerpodcast
The First Customer podcast website
https://www.firstcustomerpodcast.com
Follow The First Customer on LinkedIn
http://www.linkedin.com/company/the-first-customer-podcast/

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 burnout and what he felt were signs from the universe.

After the sale, a serious health scare prompted Christian to reassess his path. Recovering from blood clots and reflecting on how a medical device saved his life, he founded Blue Goat Cyber with a mission to secure medical technologies. Drawing on earlier industry experience, he strategically niched the company to focus on medical device cybersecurity, guided by FDA mandates and a clear understanding of the market’s pain points. Christian talks about reactivating old contacts, leveraging past partnerships, and using tools like StoryBrand to refine messaging and positioning.

Discover Christian Espinosa's story of resilience, reinvention, and finding purpose in solving critical problems that matter in this episode of The First Customer!

Guest Info:
Blue Goat Cyber
https://bluegoatcyber.com

Christian Espinosa's LinkedIn
https://www.linkedin.com/in/christianespinosa/

Connect with Jay on LinkedIn
https://www.linkedin.com/in/jayaigner/
The First Customer Youtube Channel
https://www.youtube.com/@thefirstcustomerpodcast
The First Customer podcast website
https://www.firstcustomerpodcast.com
Follow The First Customer on LinkedIn
http://www.linkedin.com/company/the-first-customer-podcast/

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 and was sold after a multi-year acquisition journey involving various potential buyers.

Dori’s latest venture, Simple Closure, was born from his painful experience trying to shut down a startup. After a board member raised the need for a shutdown plan during a downturn at Earny, Dori found little support from advisors and a lack of public resources. This inspired him to build a solution for the thousands of companies that face similar closures annually. Through founder interviews and increasing inbound interest, Simple Closure found its first customer even before launching a formal product, confirming a strong demand for a structured and compassionate shutdown service.

Let’s head to the Sunset Capital as Dori Yona shares how he’s destigmatizing failure and simplifying shutdowns for startups and small businesses in this episode of The First Customer!

Guest Info:
Simple Closure
https://simpleclosure.com

Dori Yona's LinkedIn
https://www.linkedin.com/in/dori-yona-b8369877/

Connect with Jay on LinkedIn
https://www.linkedin.com/in/jayaigner/
The First Customer Youtube Channel
https://www.youtube.com/@thefirstcustomerpodcast
The First Customer podcast website
https://www.firstcustomerpodcast.com
Follow The First Customer on LinkedIn
http://www.linkedin.com/company/the-first-customer-podcast/

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.

Mark explains that his transition into coaching was a natural evolution of the informal mentoring he had done throughout his corporate career. He combined that passion with formal coaching training and inspiration from Dan Martell’s hybrid coaching/mentorship style. Today, through The Maverick CTO, Mark helps tech leaders navigate challenges in leadership, team building, and stakeholder management. He emphasizes that charging for coaching not only sustains his business but also deepens client commitment and results.

Join us as Mark Wormgoor unpacks why startups should never build without customers in this insightful episode of The First Customer!

Guest Info:
The Maverick CTO
https://themaverickcto.com/

Mark Wormgoor's LinkedIn
https://www.linkedin.com/in/mwormgoor/

Connect with Jay on LinkedIn
https://www.linkedin.com/in/jayaigner/
The First Customer Youtube Channel
https://www.youtube.com/@thefirstcustomerpodcast
The First Customer podcast website
https://www.firstcustomerpodcast.com
Follow The First Customer on LinkedIn
http://www.linkedin.com/company/the-first-customer-podcast/