Never Stop Starting

If you missed the shortcut, make a u-turn

John Schenk
May 23, 2017 · 5 min read

New York in 90s

I used to work in the music business. Most people find that pretty cool. And yeah, it kinda was. I met famous people, went to countless shows and got all the product I wanted for free. New York City was my home, and I was set. Or so I thought.

As quickly as “grunge” music was out, the new tech boom was in. It was the mid 1990s, and I found myself deeply fascinated with some of the earliest Internet technology companies. And I was enamored with startups. In my final year of grad school, I did a report on eBay — only a few months old at that time, and wrote a paper on the benefits of online retail (back when the notion of selling clothes on the Internet was still frowned upon). On a creative whim, I built a financial model for bringing hiring firms and job candidates together online. But that fantasy was quickly snuffed when came online that same year. At that point, it occurred to me that while I had a few decent ideas, I did not have the wherewithal to realize anything. I was a dreamer, not a programmer.

By the late 1990s, I spent all of my time researching companies and playing the stock market. It was my way of hacking the system and participating in the growing tech boom. But doing so from a distance wasn’t quite enough. I was stuck in a corporate job and living on the wrong coast, the way I saw it. I needed to be in the middle of all the action — where new ideas and dreams were being brought to life. I wanted to be on the front lines, making shit happen. I needed a reboot.

For some time, I regretted not having moved back home after school. I grew up in Southern California, and attended Indiana University for my bachelor’s degree. I studied business, and decided on a path in corporate finance. It sounded like the right decision at the time. Finance jobs were known to pay well, so why not? Accounting, Marketing, and Liberal Arts weren’t quite right for me. And back in those days, “Engineering” meant learning how to design and build machines and structures. So, Finance it was. I moved to NYC and scored an Analyst role at Arista Records. I learned a lot, and it was an exciting time. But in a flash, technology was on a tear and the world began to change. If only I had moved to San Francisco after graduation! Who knows what might have been.

Silicon Valley in the 2000s

That was all water under the bridge, and as they say “it’s never too late”. So I decided to make a change. I crafted a plan to segue out of the entertainment business, and toward the tech world. Over the next year, I applied for a variety of jobs on the West Coast and made a couple of trips out for in-person interviews. I remember being amazed at the number of well-known companies scattered along US route 101: Google, Yahoo!, Oracle, Sun Microsystems, etc. And so many startups. You could feel the energy everywhere. And all of this nestled within a small yet serene location known as the “mid-peninsula”, just a few miles from the ocean and halfway between San Francisco and San Jose. VCs kept their offices in quaint business developments surrounded by woods, where deer could be seen through the windows in the early morning fog. And millionaires drove Toyotas to work as an act of humility (surely saving their exotic vehicles for the weekends). It was all like a scene straight out of HBO’s “Silicon Valley”.

I eventually landed a job as VP of Corporate Strategy at Live365, a streaming audio startup company that allowed average people to create their own Internet radio stations and broadcast to the masses. It was the perfect next step in my career, and one that put me back where I wanted to be — back ahead of the curve. My wife and I moved across the country, made new friends and never looked back.

SoCal in the Present Day

Years have passed since that move, and we now live in Los Angeles. I’ve spent more than a decade working for a handful of terrific startups — a few of which ended in success, and others in failure. But collectively, they’ve all provided me with invaluable experience. I’ve put my corporate background to good use, advised young founders, and helped materialize a few great ideas. I still don’t code, but I know to build a business — from scratch. And I’m still chock full of ideas. My latest and greatest is Taffy (, a new kind of social discovery application that breaks all the rules. Just how I like things!


Yeah, I missed the shortcut. I didn’t grow up with a smart phone. I didn’t go to Stanford. I’m not a engineer. And I didn’t quit school to pursue my prototype. Who cares?! With a little motivation and a decent plan, I quickly made up for lost time. And anyone can do the same. My recommendation to those who may be dissatisfied with their careers: Take a class or learn a language. Go back and get a degree or certification. Pick up and move, if you must. It will be difficult at first, but you’ll be glad you did. And remember, it’s never too late. Never stop starting. I’m still doing it today with Taffy. It’s my third shot at building something special, but as they say, the third time’s a charm.

John Schenk is Founder and CEO of Taffy (launching in June 2017).


How the Taffy is made

John Schenk

Written by

Startup tech CFO. Blockchain/crypto enthusiast. Founder of Taffy. Follow @chewtaffy @johnschenk



How the Taffy is made