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Empowering The Next Generation Of Startup Leaders

In 20 years time, we’ll look back on this decade as the golden age of startups – an era when immense value was created out of small geographic pockets of tech innovation and fledgling companies lead by visionary entrepreneurs disrupted every facet of our personal and working lives. I’ve been fortunate to have played a small role in this business transformation. But as much as we’ve seen unprecedented disruption – a change in business processes and business models –  I don’t believe this decade will be an outlier. I think the creative thinking that has heralded a new technology age in this world will only drive more business change (and success) for years to come. Today’s startups have shown that great ideas formed by persistent, focused founders and their teams can take on and win in markets of any size and business vertical. It just takes immense fortitude and conviction.

But as we’ve seen time and time again, no founder or growth executive can do it alone; it really takes a village. The next wave of innovative companies will be ushered by a community of investors, entrepreneurs and genuine market-makers. Following are three ways I believe today’s startup leaders can pay-it-forward to the next round of tech standouts.

Drink the Kool-Aid

When it comes to startups, I’m a true believer. I started my career at WhippleHill, an EdTech SaaS startup that was acquired by Blackbaud, worked in successive executive growth roles at Dyn, exited to Oracle in January 2017, and have been an active angel investor for the bulk of my career – literally, from the time I could begin investing, I began investing in the startup community.

Before you can be an effective coach for the next generation of leaders, you need to be all-in on the idea that startups offer a phenomenal path for anyone with grit and ambition. But there’s no sugar-coating how hard building a successful startup can be. 90% of startups fail (though many of the brightest startup stars have experienced failure before arriving at success in a later venture). The best way to help steward future entrepreneurs is to believe in your bones that tech startups can truly change the world.

Support – and Enable – Your Local Tech Ecosystem

Showing support for startups goes well beyond the help your wallet can provide for founders. The best tech ecosystems build from good to great from strong roots nurtured over time. Silicon Valley has grown to be the center of the tech world because of decades of investment in ideas, people and the infrastructure (both private and public) that it takes to support the continued momentum of invention. Success breeds success, but creating a nurturing environment with advisors and resources is critical to building a sustained startup scene.

In Manchester, NH – part of the greater Boston tech ecosystem – we’ve worked to build such institutions via the Alpha Loft, a coworking space and startup accelerator, the New Hampshire High Technology Council (NHHTC) and other localized 501c3’s and venture efforts. But it’s also important to give your time and ear. Respond to emails. Take 30 minute meetings with budding entrepreneurs as a point of commitment and pride. The next generation of leaders is truly in our hands and they are looking to you as the top of the mountain. Be self aware enough to know that this symbolism matters and your accessibility is important.

Be the Change you Believe In

Mentorship is one of the least talked about resources for any successful startup leader. Failure is a great teacher, but who wouldn’t want an experienced voice to help them guide around missteps that may be hiding in plain sight? Advising from the school of hard knocks, an operators lens, makes all the difference.

One of the most effective ways I’ve found to provide guidance to other founders is by acting as an advisor to startups, both formally and informally. I currently serve on the boards of Datanyze, CloudApp and York Athletics MFG. and informally advise at least a dozen additional startups around the country. Expert council is critical to inexperienced leaders and helping steer a company to fruitful waters is one of the most rewarding things any entrepreneur can do.

I also believe adamantly about living the startup lifestyle – actively investing and starting other companies as a long-game action of entrepreneurship. I’ve long invested in startups, have a strong AngelList cohort and have had several positive exits. My brothers and I started York Athletics MFG. a third-generation family-owned footwear brand, several years ago and it’s kept my instincts on growth and brand-building well-honed. Keeping close to businesses that are fighting the good fight is critical to your own startup flame burning so you can continue to lend your time and resources to others.


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Whois: Kyle York

Kyle York is GM & VP, Business & Product Strategy, and has been a long-time executive, having joined in 2008. Over the years, he has held go-to-market leadership roles in worldwide sales, marketing, and services. In his current role, Kyle focuses on overall corporate strategy, including: positioning and evangelism, new market entry, strategic alliances and partnerships, M&A, and business development. Outside of Oracle Dyn, Kyle is an angel investor, entrepreneur, and advisor in several startups.