In this episode, I was lucky enough to interview Nicky Senyard, CEO and founder of Fintel Connect.

Nicky shared the journey behind Fintel Connect—a digital acquisition platform that helps financial institutions across North America grow their customer base through affiliate marketing. She explained how the platform acts like the “plumbing” between banks and publishers like NerdWallet or Credit Karma, using a CPA (cost-per-acquisition) model that rewards performance and delivers real value.

Nicky also opened up about her roots in Australia and how the country's rugged environment shaped her entrepreneurial resilience. Before Fintel, she built and successfully exited the world’s largest affiliate platform for regulated online gambling. We talked about everything from building networks in unfamiliar markets to earning trust in a highly regulated space like financial services. Nicky emphasized the importance of curiosity, authenticity, and solving real problems—especially when selling to institutions that don’t always know what they’re missing.

Sit back and hear Nicky's biggest takeaway from years of building businesses in this episode of The First Customer!

Guest Info:
Fintel Connect
https://www.fintelconnect.com

Nicky Senyard's LinkedIn
https://www.linkedin.com/in/nickysenyard/

Want to be a guest on The First Customer? Send Jay Aigner a message on PodMatch here.

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 serial entrepreneur Eric McHugh once again!

Eric dives into his latest venture, dataing.io, an AI-powered matchmaking app built to challenge the typical swipe-based dating model. He shares how the Web3 space supports his builder mindset and leads to the creation of Hold On Labs, a platform that launches products focused on meaningful connection. With dating.io, the goal is to create intentional, high-quality matches using AI-generated personality tags based on users’ social media and digital activity. Unlike Tinder or Hinge, which aim to keep users engaged and swiping, dating.io focuses on helping people find lasting matches and offers a “relationship butler” that helps couples with date planning, gift ideas, and relationship support.

Eric also shares their go-to-market strategy, which focuses on building local communities by starting with Southern California colleges through campus events, partnerships, and free photography incentives. The team is currently focused on gaining users, with a goal of reaching 10,000 in Los Angeles before expanding further. Monetization is not the immediate priority, but future plans include earning a share from date bookings and offering targeted brand placements. Eric points out that AI is not just a trendy term for them; it powers the platform’s ability to understand behavior and preferences, leading to smarter and more accurate matches.

Be intrigued by Eric McHugh’s pursuit of meaningful tech, smarter matchmaking, and the vibes behind dataing.io in this episode of The First Customer!

Guest Info:
dataing.io
https://apps.apple.com/us/app/dataing/id6478563884

Eric McHugh's LinkedIn
https://www.linkedin.com/in/ericdouglasmchugh/

Want to be a guest on The First Customer? Send Jay Aigner a message on PodMatch here.

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 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/

Want to be a guest on The First Customer? Send Jay Aigner a message on PodMatch here.

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/

Want to be a guest on The First Customer? Send Jay Aigner a message on PodMatch here.

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 Ben Fellows, CEO and founder of Loop QA.

Ben shares how his company addresses the growing need for highly skilled, mid-to-senior QA professionals in a market lacking structured training and clear entry paths. Loop QA focuses on embedding experienced testers directly into teams at startups and enterprises, filling a critical talent gap with candidates who bring technical expertise, product understanding, and emotional intelligence. Ben explains how many successful QA professionals arrive from unconventional paths—often self-taught or transitioning from roles in development or customer success—and highlights the industry's broader need to recognize QA as a strategic, trust-building function rather than a final checkpoint.

Ben also opens up about his personal journey into entrepreneurship, shaped by watching his mother run her own business and a brief stint in politics that led him to the fast-paced world of startups. He describes the early days of Loop QA, including the unconventional strategy of offering free QA services to build a client base, and how that experience shaped the company’s sales and growth philosophy. He reflects on the evolving nature of QA’s role within organizations, the emotional toll of being seen as the “last line of defense,” and the importance of creating a healthy quality culture.

Whether you're trying to hire QA talent, break into the field, or simply want to better understand the mindset behind it, this episode of The First Customer delivers clarity, context, and plenty of relatable moments!

Guest Info:
Loop QA
http://www.workwithloop.com

Ben Fellows' LinkedIn
https://www.linkedin.com/in/ben-f-44778426/

Want to be a guest on The First Customer? Send Jay Aigner a message on PodMatch here.

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/