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Reshaping How Startups are Built, Scaled, and Monetized: Interview with Kyle York

Kyle York is co-founder, CEO, and managing partner at York IE where he sets the company’s vision of building a hybrid strategic advisory, investment, and operational growth firm. Kyle works closely with entrepreneurs and investors to help them realize their shared ambition to build good companies, create new jobs, grow generational wealth, and impact the world.

Investing in over 70 startups over the past decade, Kyle is also a co-founder and board member for 3rd generation family business, YORK Athletics MFG., an eCommerce footwear brand in Boston, and is an independent board member for Assent Compliance, CloudApp, and Forcivity.
In today’s interview, we will be spending some time talking with Mr. York on the topics of mindset, product strategy, changing the way startups are built, scaled, and monetized.

Once you’re done with the interview, you follow Kyle on Twitter.




Q. Welcome to StartUp Mindset, Kyle. We’re very excited to have you here.   For the readers who are not familiar with you, could you tell us a little about yourself and your background?

I’m a technology entrepreneur and investor who loves building companies. I grew up in a large family in southern New Hampshire. My parents owned a local sporting goods store and so I was ingrained, from a young age, with the values of a small business: be fiscally responsible; work hard every day; and be active in your local community.

Those lessons stayed with me during college and then at my first job, which was selling educational software to private schools. From intern, I worked my way up to head of West Coast Sales and Marketing. Eventually, I returned home to New Hampshire to become the first sales and marketing executive at Dyn, which was an internet infrastructure company. We grew Dyn from 15 people to 500 with $100 million annual recurring revenue before we were acquired by Oracle in 2016.

Within Oracle, I led product strategy for its cloud division for three years. Until leaving this past summer to found York IE.


Q.  What kind of mistakes do you see many startups make when developing a winning product strategy?

The biggest mistake we see startups make is not taking a market-in approach to strategy. Instead, they think product-out, which ignores the broader playing field. I understand why this happens. A lot of startups are created by brilliant technologists or subject matter experts. They know their product cold. That is a good thing. But you need to fully understand the competitive landscape and even the comparative landscape. Only when you know your market as well as you know your own product, can you truly define your vision, strategy and execution plans and deeply understand your differentiators to create the much sought after moat that leads to profitable growth.


Q. You launched York IE recently to help startups in a unique way.  Tell us more about the company and what it does differently.

York IE was founded on the desire to reshape how startups are built, scaled and monetized. We believed that the current model of the support system around startups (aka investors/vendors) from venture capital to business consultants to market analysts is ripe for disruption. I think a lot of the players in those aforementioned spaces have forgotten, or never knew, what it is like to be in the shoes of an entrepreneur.

We haven’t. And I know we never will.

So we approach everything trying to be as entrepreneur-friendly as possible. We want the startups we work with to find their own path that is what’s right for the long-term growth of their company. Good companies have good options.



Q. York IE is growing fast.  What do you think you and your team have done right that has helped the company’s growth?

I think we’ve listened.

Doing that has allowed us to identify needs that startups have expressed and then create offerings that solved some of those problems.

We heard that entrepreneurs were tired of being told to raise as much capital as possible and dilute their own equity stake and so we launched our investment practice. In working closely with our portfolio companies, we identified a clear need for a services offering that was affordable, adaptable, and always-on. As a result, we launched our services offering.

And through that all, we realized that every startup would benefit from a more market-in approach and so we’ve doubled down on that as a differentiator for ourselves and have gone as far as building our own proprietary market data and analytics platform. This platform fuels everything we do.



Q.  Is there a major leadership lesson that you learned during your time at Dyn and Oracle that you wish you could share with everyone in a leadership position?

Surround yourself with complementary skill sets and people who challenge you and make you better.

At York IE, I have known my co-founders since we were little kids, which may be taking that above statement to the extreme. But we have complimentary skills, we always feel comfortable to call BS on each other and we also know, without a doubt, that everyone is working with the best interest of our collective vision.

Never underestimate the importance of those things. They are what get you through the tough times. And there will be tough times and that is when you, as a leader, will be judged. But having that support system makes things easier and a lot more fun.


Q.  For startups in the survival stage of their business growth, what advice would you give to help them reach the success stage?

Being an entrepreneur building startups is incredibly lonely. First and foremost, try and slow it down, maintain perspective, think big picture, and focus on playing the long game. But more than anything else, take care of you first, talk to people about the challenges you face (mentors, parents, spouse, colleagues, friends, therapists – all of the above) and realize that you’re not in it alone during the survival stage.

When times get hard during this, some can turn into hermits, isolate and let fear and uncertainty take over. That’s natural, but power through it. The only way people get through difficult circumstances is by leaning on the people that got them there in the first place and care about them and their mission. Once you talk it out, then course correct, reset the foundation, establish the markers ahead and keep going. You’ll get there and you don’t have to do it alone. This journey, each stage to success – is certainly a rollercoaster.

Q. What mindset or trait do you think every entrepreneur must possess in order to become successful?

“It’s the principle of the thing” was the mantra in my house growing up. When I lay in bed at night, I can still hear my father saying it. Nothing else matters if you fail this piece of advice. What’s the point of winning the world if you lose yourself in the process?

Take a moment to think about what your guiding principles are or will be. These should be foundational principles you write down and don’t break. If for some reason you do break them, you better have a damn good reason why. And at that point, you may want to think about updating your principles.

From the beginning of my career, I’ve operated under these two principles:

  1. Be loyal
  2. Play the long game

These are the lenses through which I view everything and the parameters I use to keep myself guided. If I do something that contradicts either of these principles, an internal warning alarm goes off in my gut. If there’s a great outcome but it comes at the expense of my principles, I don’t pursue it. The end doesn’t justify the means. “Be principled.”

Ralph Paul on Twitter
Ralph Paul
Ralph is the Managing Editor at StartUp Mindset. The StartUp Mindset team consists of dedicated individuals and is designed to help new, seasoned, and aspiring entrepreneurs succeed.

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Ralph is the Managing Editor at StartUp Mindset. The StartUp Mindset team consists of dedicated individuals and is designed to help new, seasoned, and aspiring entrepreneurs succeed.

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