In this episode, I was lucky enough to interview with Dan Goldsmith, co-founder and chairman of Tendo and co-founder of Proofpoint Capital. 

Dan shares stories from his Philadelphia roots, the early formation of his grit, and the mindset that has guided his career — from running a mobile DJ business in high school to building and scaling multiple technology companies. He offers a thoughtful perspective on perseverance, explaining how deep obsession with a problem can fuel success, while also highlighting the risks of letting conviction turn into blind spots.

Dan delves into Tendo’s mission to modernize healthcare by putting patients at the center, improving access, affordability, and quality recognition for providers. He provides a candid take on the economic realities of healthcare, the evolving influence of AI, and why meaningful industry change may be driven more by employers than regulators. Dan also discusses his newest venture, Proofpoint Capital — an operator-led fund built to help early-stage companies scale through pattern recognition and decades of hands-on operating experience.

Discover how grit, focus, and pattern recognition shaped Dan Goldsmith’s journey in this episode of The First Customer!


Guest Info:
Tendo
http://tendo.com

Proofpoint Capital
https://www.proofpointcapital.com/


Dan Goldsmith's LinkedIn
https://www.linkedin.com/in/danielgoldsmith/

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 Joel Reed, CEO and founder of Open Arc.

Joel starts to unpack the long, nonlinear journey of building a software consulting company that’s lasted more than 20 years. Joel shares how a career plateau, the 2008 financial crisis, and a humbling professional low point ultimately pushed him to start Open Arc. From working four 10-hour days to fund the business on the side, to landing their very first customer through trusted relationships, Joel reflects on how resilience, timing, and people-first decision-making shaped the company’s foundation.

Joel dives into how Open Arc evolved from “doing everything for everyone” to deliberately narrowing its focus, saying no, and specializing in markets where they can truly differentiate. He discusses the post-pandemic shift in lead generation, the growing importance of vertical expertise, and how Open Arc is refining its positioning by listening closely to customer pain points. Joel also shares candid advice on starting a services business today, the realities of project-based work, the role of AI in modern software development, and why building a strong team with shared values remains the most important first step—no matter the era.

Learn how Joel Reed built trust, focus, and longevity in a constantly changing software market in this episode of The First Customer!


Guest Info:
Open Arc, LLC
http://www.openarc.net

Joel Reed's LinkedIn
https://www.linkedin.com/in/joel-reed-oa/

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 Calvin Hendryx-Parker, CTO and co-founder of Six Feet Up.

Calvin shares the origin story behind Six Feet Up’s unforgettable name—drawn from his family’s mortuary business—and how servant leadership, community involvement, and trust became foundational principles for building a durable software consultancy. From hosting websites on a literal coffee-table server in a San Francisco apartment to becoming an AWS Hero and Tech Executive of the Year, Calvin’s story is anything but conventional.

Calvin delves into community-driven growth, long-tail relationship sales, and why he believes genuine connection beats aggressive pipelines every time. He explains how building and nurturing developer communities like Indie Py shaped both his leadership style and Six Feet Up’s talent strategy, why introspection and self-awareness matter more than hustle culture, and how staying agenda-free has led to consistent, sustainable growth. Calvin also shares his outlook on leadership, optimism, global empathy, and why helping people come together may be the most powerful business strategy of all.

Join us in the Hoosier State to explore Calvin Hendryx-Parker’s approach to leadership, learning, and creating momentum without forcing it in this episode of The First Customer!


Guest Info:
Six Feet Up, Inc.
http://www.sixfeetup.com

Calvin Hendryx-Parker's LinkedIn
https://www.linkedin.com/in/calvinhp/

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 Near, Founder and CEO of Helios, a performance wearable helping hockey players and teams improve faster through motion-based data and video integration.

Bill breaks down Helios’ first-principles approach to avoiding “tech fatigue” by delivering recurring, practical value—most notably through time-saving video workflows and emerging AI-driven coaching insights that turn raw data into actionable development guidance for players and parents alike.

Bill also shares the personal and technical journey behind Helios, from growing up playing hockey in New Hampshire to studying engineering at MIT and recognizing a critical gap in player development technology. He explains how Helios was built as a zero-infrastructure solution using motion sensors rather than rink-based tracking, enabling scalable adoption across youth, collegiate, and professional levels.

Be inspired by Bill Near’s clear-eyed take on data, coaching, and building technology athletes actually stick with on in this episode of The First Customer!


Guest Info:
Helios
https://helioshockey.com/


Bill Near's LinkedIn
https://www.linkedin.com/in/billnear/

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 Ole Lensmar, co-founder and CTO of Testkube.

Ole shares his unique perspective growing up across Germany, the US, and Sweden, and how those experiences shaped his adaptability and approach to entrepreneurship. He reflects on the differences between launching tech startups in Europe versus the United States, and why he believes the US remains a more mature market for scaling innovation. From his first ventures in the mid-90s to the creation of SoapUI, Ole explains how his passion for coding and solving practical problems led him to build tools that filled gaps in the QA and software testing space.

Ole dives into the origins of Testkube, explaining its mission to decouple testing from CI/CD pipelines and empower QA teams with a centralized, cloud-native platform. He discusses the open-source model, the challenges of enterprise sales, and the evolution of his ideal customer profile. Ole also shares insights on how Testkube differentiates itself from CI/CD tools and cloud execution vendors, enabling companies to run unlimited tests at scale without infrastructure limitations.

Explore how Ole Lensmar turned coding challenges into software solutions and shaped modern QA practices in this episode of The First Customer!


Guest Info:
Testkube
https://testkube.io/


Ole Lensmar's LinkedIn 
https://www.linkedin.com/in/olensmar/

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 Det Ansinn, the founder of Brick Simple LLC, serial entrepreneur with four successful exits, and current CEO of MedTech company Neuralert. 

Det shares his journey from pumping gas at the Doylestown Airport to building multiple innovative ventures, emphasizing the value of authentic connections, strong team culture, and pursuing projects that excite him over purely profit-driven motives. From creating Brick Simple’s first product to developing apps for Xbox Live and navigating the post-dot-com era, Det reflects on how his experiences shaped his approach to entrepreneurship and leadership.

Det also delves into his current work at Neuralert, a breakthrough stroke detection company, where he stepped in as CEO following the previous leader’s unexpected passing. Det discusses the unique challenges of leading a company he didn’t found, the importance of building resilient teams, and his dedication to making a meaningful impact in healthcare. He also shares insights on the Bucks County startup ecosystem, balancing professional intensity with personal passions like motorcycling, and maintaining perspective through mental health practices. 

Step inside Det Ansinn’s world and discover a career fueled by curiosity, innovation, and purposeful action in this insightful episode of The First Customer!


Guest Info:
BrickSimple LLC
http://bricksimple.com

Neuralert Technologies
https://neuralert.co

Det Ansinn's  LinkedIn
https://www.linkedin.com/in/detansinn/

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 Chris Molaro, CEO and co-founder of NeuroFlow. 

Chris unpacks the personal and professional journey that takes him from growing up in Queens and Long Island to serving as an Army officer and ultimately building a healthcare technology company. Chris shares how the events of 9/11, his experience at West Point, and years of active-duty service shape his leadership philosophy and resilience. He reflects on his transition from military to civilian life, emphasizes the importance of “running toward something, not away from something,” and explains how lessons from combat—especially maintaining perspective under pressure—continue to guide him as a CEO.

Chris delves into the genesis and evolution of NeuroFlow, inspired by a tragic gap in mental health care he witnesses during his military service. He explains how he and his co-founder identify systemic failures in tracking outcomes and coordinating care, and how they build NeuroFlow by working directly with frontline providers to solve urgent, real-world problems. From landing their first paying customer—a private therapist in Philadelphia—to serving enterprise healthcare organizations, insurers, and the VA, Chris walks through how the company scales by prioritizing measurable impact over “nice-to-have” technology. 

Discover how Chris Molaro turns lived experience and leadership into a mission to close critical gaps in mental health care on this episode of The First Customer!


Guest Info:
NeuroFlow
http://www.neuroflow.com


Chris Molaro's LinkedIn
https://www.linkedin.com/in/chrismolaro/

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 the legendary sales expert and bestselling author Jeb Blount.

Jeb shares stories from his upbringing in small-town Georgia, where being the smallest kid in school taught him grit, hustle, and the relentless work ethic that would later define his career. He talks about finding confidence through public speaking, his early ambition to become a lawyer, and the surprising moment—thanks to “Rudy” himself—that pushed him to write his first book and eventually build Sales Gravy into a powerhouse sales training company.

Jeb also breaks down how elite performance in sales mirrors elite athletics, why founders must embrace selling before they can scale, and how persistence—not perfection—is the real engine behind long-term success. From cold calling alongside his clients to the evolution of Sales Gravy’s earliest customers, he offers a candid look at the mindset and habits that sustain high-impact sales careers.

Join Jeb Blount as he delivers both practical lessons and an inside look at the drive that built one of the most trusted brands in sales development today in this episode of The First Customer!


Guest Info:
Sales Gravy, Inc.
http://www.salesgravy.com/

The LinkedIn Edge
https://jebblount.com/product/the-linkedin-edge/

Jeb Blount's LinkedIn
https://www.linkedin.com/in/jebblount/

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 Joel Montvelisky, co-founder and Chief Product Officer of PractiTest.

Joel shares his unlikely journey from Costa Rica to the world of software testing. He talks about becoming a Cowboys fan in the 1970s, stumbling into QA because it paid slightly better than bartending, and eventually discovering that testing was far more than bug hunting—it was about improving products, reducing risk, and helping teams release with confidence. He reflects on the evolution of QA from the dot-com era to modern Agile and DevOps practices, the absence of formal QA education, and how conferences and early industry leaders helped him realize that testing is, in fact, a real profession with deep methodology and purpose.

Joel also shares the origin story of PractiTest, born from a gap he saw between enterprise tools like Quality Center and teams struggling to manage testing with spreadsheets. He explains how the company’s very first customer found them before they even had a way to accept payments, how founder-led sales carried them for years, and why meaningful testing requires both intention and mindfulness—something he practices personally to stay focused as someone diagnosed with ADHD later in life. 

Hear how Joel Montvelisky turned unexpected beginnings into a career shaping the future of QA in this episode of The First Customer!


Guest Info:
PractiTest
https://www.practitest.com/


Joel Montvelisky's LinkedIn
https://www.linkedin.com/in/joelm3/

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 Andy Kochanowski, founder and CEO of Alerify, a data center based in Harrisburg, Pennsylvania.

Andy shares his journey from a 30-year career in corporate America, including service in the Navy, to taking the leap into entrepreneurship. He explains how Alerify serves a niche market of small and medium-sized businesses seeking secure, localized data storage through co-location and virtual private cloud solutions, providing a personal, hands-on approach that sets them apart from the hyperscale public cloud providers.

Andy also dives into the process of acquiring and revitalizing Alerify, from conducting meticulous due diligence to investing in infrastructure improvements, achieving SOC 2 compliance, and building a strong local network. He discusses early client wins, including iHeart Media, and shares his approach to leveraging AI at the edge for private, secure data processing. Along the way, he offers advice for aspiring business owners about finding the right opportunity, valuing culture alignment, and starting local before scaling.

Tune in to Andy’s story as he highlights the blend of strategic planning, technical expertise, and human connection that drives his company’s growth in this episode of The First Customer!


Guest Info:
Alerify
https://www.alerify.com/


Andy Kochanowski's LinkedIn
https://www.linkedin.com/in/andrew-p-kochanowski-ph-d/

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/