This past July, in the middle of New Hampshire’s summer humidity, I departed from the job that had been a major part of me for nearly 11 years. Much like most of my experience within large corporate life, that departure was without thrills, eerily silent, and as anticlimactic as it gets.
Fortune 100 scale brings such a fascinating juxtaposition to fast-growth startups. In private, smaller companies, it feels like every action by every person makes an impact on the business. This is especially palpable for leaders and executives. In an enterprise the size and age of Oracle, making a dent doesn’t come easy. And, even when it feels like you are driving outsized value, the tides can turn in an instant. I think only those who have experienced and really lived through both can entirely relate.
My team and I gave it our 100% best shot at Oracle and really felt like we had a tiger by the tail for a while. That’s the naïveté and beautiful ignorance of entrepreneurs and an entrepreneurial culture. You set seemingly insurmountable goals, stay absurdly positive, constantly rally the troops, and assertively aim hard at conquering that hill. Within Oracle, I would tell my lieutenants to focus on the “conquerable mountains” and ignore the minutia, politics, bureaucracy and startup gravitational pull – fueled by every recruiter on the planet aiming to place some of that Dyn magic (or Wercker, DataScience, StackEngine, Zenedge – all team members from M&A’s who worked for me) – for as long as they could. I convinced the teams that we could be a catalyst on Oracle’s cloud journey, help them modernize, introduce DevOps and learn a lot personally and collectively along the way. We accomplished all that and more. Worth noting, the above negatives are not meant to be knocks – simply reality. Many find the stability, large budgets, big teams, and focused roles and processes, a great fit for them.
When Dyn sold to Oracle in late 2016, I wish I could’ve bottled up the euphoria, pride and relief I felt. When you build a startup, I mean really build it, there is nothing career-wise more rewarding than realizing the vision through all of the grit and the grind. It’s the ultimate satisfaction.
I searched for that every day at Oracle. There were immense highs: speaking at Oracle media day in front of 50 of the most influential journalists in the world (twice!), a deep dive interview with Bloomberg, talking artificial intelligence at Fortune Brainstorm, keynoting OpenWorld London (7,500 attendees) and McAfee MPower (7,500 more), being Oracle Cloud’s key executive spokesperson for media and analysts and featured in WSJ, Inc., Forbes and more, in-depth cloud Q&A with SeekingAlpha, Silicon Valley networking at Safra and Larry’s homes, video interview in GeekWire, acquiring cybersecurity startup, Zenedge, leading Oracle Cloud Infrastructure product strategy and developer relations and continuing to help lead Dyn as GM with an over $100M P&L responsibility to manage.
But that’s just it. There are builders and there are managers. I for one am absolutely at my happiest in the former. I’m a builder. I love the diversity and chaos of startups. I couldn’t be more excited to take what I’ve been doing as a serial entrepreneur, advisor, board member and investor 1% of my time and merge it with my immense operational experience at WhippleHill (now Blackbaud), Dyn and certainly Oracle and shoot for the moon again – 1000% of my time because I know no other way.
No matter what I’m doing, I obsess and go for it. No more lonely, confusing and isolated summer walk outs of amazing career stretches again. I have no regrets, but now it’s time to get back to my DNA and make a huge and felt impact with my loyal, committed, and complementary team!
Let’s find our “conquerable mountain” again!