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True Board Story: The Email That Landed Jason Calacanis

(On Tuesday, Oct. 2, 2012, Dyn announced it had received $38 million in funding from North Bridge. But the other piece of news that dominated the headlines was that Mahalo CEO, serial entrepreneur and angel investor, Jason Calacanis was joining Dyn’s board. How did Dyn land an Internet celebrity like Calacanis? Well, it is important to keep an ongoing relationship. But it also helps to send out a killer email pitch.)

The Email:

On Sat, Apr 21, 2012 at 8:45 AM EST, Kyle York <> wrote:

Hey Jason,

Hope things are going well. As you know, I’m a big fan and am always keeping an eye on what you’re up to. I’m not writing to ask for your money or free advice. I realize tons of people probably think it’s that simple. Your name just came up when I was talking to my CEO and great friend, Jeremy Hitchcock. He asked me to drop you a line because we “know” each other. Please read on… this gets good.

Dyn has grown since I started from a $4mm/year, 15 person, consumer/smb IT services company to a pretty robust 150+ person IaaS (infrastructure as a service) company for managed DNS & email delivery, that is chasing down $35+mm in bookings for 2012. You know our clients Twitter, Angry Birds, Zappos, Etsy, etc. You hopefully know our disruptive style and unique profile in a stodgy/corporate/slick enterprise infrastructure space.

Jason Calacanis

We’ve bootstrapped the entire thing from day one in that tiny apartment in Worcester, MA. Our leadership has done an amazing job getting it to this point, are confident we can keep growing, but feel like we need some help. We know what we don’t know.

Yes, we’re an enigma. We’re HQ’d in Manchester, NH, specialize in Internet plumbing and have an exec team (with two co-founders) with a combined 50 years of professional experience (do the math, there are five of us, and I might be exaggerating a little). We’ve gotten to a size and scaling pace where we are considering assembling a compensated board of directors/advisors/observers (folks with a retainer and equity take) that can help us go from 150-300+ people and $35mm to $100mm+ to IPO or an exit to some big juggernaut. Whatever works. Our current board is our CEO, Jeremy Hitchcock and our CTO (now chief scientist), Tom Daly, both founding team members of the business and leading us for the past 10 years. The three other execs are minority shareholders. I believe in this 110%.

Anyway, all my contact info is below. You’re on a short list. Meaning, this email was not sent to anyone else – yet. We want someone who understands the Internet, is technical, is disruptive, and who’ll make noise. We want someone who’ll challenge us, who’ll expect more, and who’ll help take us to new heights. We want people who remember DynDNS when it was just a free hobby and loved it.

We have two other candidates we’re pretty serious about who know our business and the players cold, but you could be the game changer we need. We’re also building this crazy tech ecosystem in Manchester, NH, and I know you’d dig it and you can invest in all of them:

Of course, please keep this all hush/hush and please take this seriously. I wouldn’t want Akamai or Verisign or Neustar to call you and steal our idea… 🙂

Talk soon,



The Response:


What a wonderful note. I’m of course flattered by your interest and intrigued by your success to date. Any plans to be on the left coast?

Best, J


The rest is, how they say, history.


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Kyle York
Whois: Kyle York

Kyle York is GM & VP, 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.

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