In this episode, I was lucky enough to interview Keilian Knudsen and Prags Mugunthan, co-founders of Pangea.ai.

Keilian and Prags explored their journey from university roommates in Scotland to building a global tech talent platform. Keilian described how growing up in Switzerland with an American mother and Norwegian father gave him a multicultural view of the world and a drive to create something of his own. Prags shared how moving from Sri Lanka to Norway at a young age gave him access to education and opportunity, which shaped his path toward entrepreneurship. Their first ventures included a sandblasting startup and a digital memory bank, both of which failed but pushed them to solve the problem they encountered firsthand—how hard it was to find and hire reliable software developers.

That problem led to the birth of Digital Knights, a service-based business that eventually became Pangea. Keilian and Prags candidly shared about the tough early days, including running out of money, borrowing from friends and family, and nearly walking away from it all. What kept them going was their shared vision and complementary strengths. They also emphasized the importance of building repeatable systems and processes, especially after realizing that excessive hustle without structure could limit their growth.

Discover how missed hires, borrowed savings, and unwavering conviction led Keilian and Prags to build Pangea in this episode of The First Customer!

Guest Info:
Pangea.ai
https://www.pangea.ai

Keilian Knudsen's LinkedIn
https://www.linkedin.com/in/keilian/

Prags Mugunthan's LinkedIn
https://www.linkedin.com/in/pragsm/

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 Aubrey Amatelli, Founder and CEO of PayRio—the first payment provider focused exclusively on alternative medicine.

Aubrey shared how her roots in Silicon Valley and a traditional finance career at JP Morgan eventually led her to launch PayRio, combining her passion for cannabis and her expertise in payments. She walked me through the complicated regulatory landscape that makes payment processing for cannabis so challenging and explained how PayRio uses creative, compliant workarounds like ATM rails and wallet tech to support dispensaries and e-commerce businesses.

Aubrey also opened up about the emotional transition from corporate life to cannabis entrepreneurship, including the fear and eventual empowerment that came with “coming out” on LinkedIn. Aubrey discussed how her startup journey began with cold calls and a scrappy three-person team, and how PayRio has grown to serve both mom-and-pop dispensaries and multi-state operators alike.

Let’s drive all the way to San Francisco and dive into Aubrey Amatelli’s bold leap from Wall Street to CBD tech in this episode of The First Customer!

Guest Info:
PayRio
https://payrio.co/

Aubrey Amatelli's LinkedIn
https://www.linkedin.com/in/aubreyamatelli/

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 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 comfort. He has literally faced death more than once and came out swinging, bringing both wisdom and humor.

Bill also delves into how he reshaped Optic Wise from the ground up, taking the bold step of zeroing out revenue to rebuild the business with long-term recurring clients in mind. He explains how their digital infrastructure transforms commercial real estate by unifying all building systems onto one resilient and secure platform, which unlocks powerful data insights that increase tenant value and property performance. He even fronted a six-figure check to land their first anchor client.

Hear Bill Douglas share how calculated risks and resilience helped reshape an industry in this episode of The First Customer!

Guest Info:
Optic Wise
https://www.opticwise.com/


Link to order "Peak Property Performance"
https://www.amazon.com/dp/1639081283


Bill Douglas' LinkedIn
https://www.linkedin.com/in/billdouglas

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 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 a reminder that progress often comes from navigating uncertainty with curiosity and humility.

Steven also unpacks how asensei’s customer base has grown beyond its original vision. While he initially anticipated serving the sports coaching market, connected fitness quickly became the company’s foundation. With strength training rising in popularity and digital fitness becoming more sophisticated, asensei now leads that category. This traction has opened doors to other markets like connected healthcare—particularly in physical therapy—and even brick-and-mortar gyms, where members increasingly expect personalized, tech-powered experiences. As Steven puts it, the company isn’t just trying to win the market—it’s theirs to lose.

See how hindsight, patience, and smart execution propelled Steven Webster and asensei to the top of connected coaching in this episode of The First Customer!

Guest Info:
asensei
http://www.asensei.ai

Steven Webster's LinkedIn
https://www.linkedin.com/in/stevenwebster/

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 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/