My Portfolio Approach to Business

Kyle York
Kyle York
Mar 13, 2016 · 3 min read

From the beginning of my career, I’ve operated with two key business principles as my foundation.

1) Be loyal

2) Play the long game

This focused effort has been evident from my first startup, WhippleHill, in which I ran west coast GTM for the better part of my 6+ years (they’ve since been acquired by Blackbaud) and throughout Dyn, since 2008, where I was the first GTM leader amongst an engineering organization looking to find its growth legs. Without these experiences I wouldn’t be where I am today as an entrepreneur, angel investor and startup advisor. It’s important to intrinsically dedicate to the golden goose day job with passion. It makes all else possible.

I’ve committed my professional career to scaling Internet companies, where I’ve been employed or involved. You can see my full portfolio and bio at my personal website,, but it’s worth noting that a big part of my personal strategy was set forth in my portfolio approach to business that my parents instilled in me at an early age.

Over the last two years, I’ve doubled down in giving back to the early stage startup community, with cash and time, being a trusted advisor to some of the most ambitious entrepreneurs in the world. This effort has also led to many of my colleagues, classmates and friends landing career defining roles in these businesses. I’ll be writing a future post on the pride I take in this “coaching tree” as I believe business is all about relationships and one person’s success can breed success for many others.

I’ve gotten some great advice in my career from mentors in this arena and I thought I’d pass along here.

A Dyn investor and friend once said to me, “The moment you start treating your personal finances like a business, is the moment you’ll start seeing your net worth skyrocket.”

Another piece of sound advice came from my personal CFO and financial advisor, Phil Swisher, who told me, “You need to maximize the Dyn halo while you can, before someday you’re just another old guy in NH with money. Now is the time to capitalize on your reach, reputation and network.”

One last piece of advice came from an angel investor friend who said, “Invest the money today that five years from now you won’t care about. It’ll keep you one step ahead. And not every investment you make is for the capitalistic return.”

A few key themes have emerged in this area of my business life. I support many startups, but there are a select few entrepreneurs and ideas that I write that larger check, deeply involve my network, and prioritize my availability. SaaS is my specialty. Technical/product founders have a special place in my heart. International founders too. Data has been a key area of focus for me. Collaboration & communication has been too. I’ve done a bunch in infrastructure and security too to complement my day job, but it’s also been the sales and marketing productivity tools that have proved of serious value in the market. Family business is under the lights with our performance footwear brand, YORK Athletics Mfg.

One could argue my family’s personal financial portfolio is littered in risk, but I would say it’s littered in tremendous upside. I’d rather bet on myself and the entrepreneurs I work with, then a stock symbol, hedge fund, or commodity, I have no control or influence over. I guess, we’ll need to wait 10 years or so to see if my strategy works out, but I’m confident it will because I’m loyal and play the long-game. 👊💰😬

Kyle York

Written by

Kyle York

Family man in NH, USA. Entrepreneur, startup advisor, angel investor. Startup growth & go-to-market strategy. http://YORK.IE