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Seeking Wisdom Podcast Recap: Kyle York on His Career Path

Kyle virtually sits down with David Cancel, CEO of Drift, and host of the Seeking Wisdom Podcast for Episode #157. In this 28 minute episode, Kyle and David discuss Kyle’s career path from Dyn to Oracle and then on to York IE. They also cover the importance of mental health and well being as an entrepreneur, and finally paint a picture of what the future of sales and marketing might look like post COVID.

Listen to this episode of the Seeking Wisdom podcast here.

Dyn Days

The conversation kicks off with Kyle explaining the early days of Dyn and how, when, and where it was built. Kyle joined in ‘09 and goes on to talk about growing the company from $3mil of ecommerce consumer revenue (when Kyle joined) to over $100mil as they dominated the enterprise DNS marketplace. Dyn has a unique success story as Kyle hits on the creativity of Dyn and its founders, something he shares with the founders of today.

Kyle shares growth/sales tips and knowledge based on his experience at Dyn and advising, founding and investing in nearly 100 startups over his career. Kyle and David discuss GTM operating models and they generate impressive revenue numbers through efficient and effective scaling.

Foundation of York IE

The convo transforms as David asks Kyle about the current state of York IE and the early-stage investing/startup landscape and they tackle the notion of field sales during a pandemic. Kyle gives David the rundown as he explains the different facets of York IE and how it fits under one modern and innovative vertically-integrated model. Kyle provides a play by play explanation of growing York IE and the different sales funnels that fall into one big integrated funnel for growth.


Later in this Seeking Wisdom podcast episode, David asks Kyle about the “dips” startups face as they grow. Kyle answers using his experience at Dyn and throughout our portfolio companies to show how the “dips” are learning experiences that help to accelerate growth. Kyle touches on the mental toll it takes to work through those trying times and how it impacted his health, but also how he’s now stronger from it.


They end the podcast with Kyle recapping his time at Oracle and his life and career experiences that came along with it. He learned the importance of mental health and David then touches on how this “game” is a psychological one, something we have shared at York IE as we released an eBook where entrepreneurs share their mental battles and best practices while playing the “game.” Kyle also recently wrote a blog on the why we all need a bit more emotional intelligence and empathy if we choose a path working with fledgling early-stage companies.

Thank you David for an awesome interview on the Seeking Wisdom Podcast, and we wish you and Drift the best of luck in 2021!

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