The First Customer - From Local Roots to Global Reach with Founder and CTO Jon Kinney

The First Customer

In this episode, I was lucky enough to interview Jon Kinney, the Founder and CTO at Headway.
Jon delves into his entrepreneurial roots, tracing his upbringing in Southwest Wisconsin. Growing up in a household where his mother was a graphic designer and his father was a musician, Jon was surrounded by creativity and technology. His first foray into business was selling items on eBay, where he learned HTML to enhance his listings, an experience that sparked his interest in programming. His exposure to his mother's company, Out of the Box Publishing, further nurtured this entrepreneurial spirit, which created the popular game Apples to Apples. These early experiences in a fast-paced, hands-on business environment greatly shaped how he approached entrepreneurship.
Jon elaborates on the early days of Headway, describing how he and his co-founders started the company from a small shared office above a wine bar. Their first big client was Handshake, a job marketplace for college students, which gave them the funding and confidence to launch Headway full-time. As Headway grew, the team focused on serving startups and leveraging local networks through initiatives like Digital Fertilizer, which connected entrepreneurs in Northeast Wisconsin. This localized approach eventually expanded as Headway gained national recognition, working on significant projects such as an innovation initiative for Procter & Gamble. Jon highlights the importance of building strong relationships and adapting to remote work, which has been key to Headway's success in expanding beyond its local market.
Dive into the world of cutting-edge business tactics with Jon Kinney, and be inspired by his unique path to success in this episode of The First Customer!
Guest Info:
Headway
https://www.headway.io
Jon Kinney's LinkedIn
https://www.linkedin.com/in/jonkinney/
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
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