5 Levels of Leadership

Every leader starts here. When I arrived at Hawaii Information Consortium in 2003 as Director of Software Development, the title got me into the room where the decision to move the legacy stack from Perl to Java got made, but it did not get engineers to actually believe in it. The organization was siloed and delivery-averse. A title opens the door; it does not walk you through it.

The shift at NIC Hawaii from siloed development to collaborative, delivery-focused teams did not come from a mandate, it came from building relationships and earning the standard-setting role rather than declaring it. The same pattern showed up years later in Colorado: the Department of Revenue had their own vendor and Governor's-office pressure to adopt our platform, and a mandate would have won the account and lost the relationship. We negotiated instead, we would not compete for their business if they made their own services mobile friendly, and eighteen months later they were our second largest partner and brought the Department of Public Safety with them.

This is the level where the numbers speak. Hawaii's government services rating went from 43rd to 1st in the nation during my tenure, with 42 national and international awards along the way. myColorado scaled from 25,000 to 250,000 users in a single month when COVID hit, reaching 750,000 by the end of summer 2020. At SporkDAO, seven years of losses turned into a $1.3M surplus in the first profitable year the event had ever had. None of that is aspiration, it is what actually happened on my watch.

On taking over as President at Hawaii Information Consortium, I built a Liaison model into the organization itself: every agency partner got a relationship manager who was simultaneously their internal advocate, growing the organization from 18 to 54 staff and earning Best Place to Work four years running from Hawaii Business Magazine. Real promote-from-within ladders ran the length of the org, Customer Service Rep to Manager of CMS, Developer to Director of Software Development, and when I stepped down as President in 2016 the succession was internal too: the sitting Chief Liaison became Director of Portal Operations, and the sitting Director of Portal Operations became President. At Bufficorn Ventures, that same instinct became guiding 50+ portfolio companies on integrating AI into their own products rather than doing it for them. At Unicorns, it is a distributed team across five countries with established delivery processes and governance frameworks they can run without me in the room.

The clearest evidence of this level is what happens after the title ends. When I stepped down as President at Hawaii Information Consortium in 2016, the organization did not need me in the room to keep running: the sitting Chief Liaison moved up to Director of Portal Operations, and the sitting Director of Portal Operations moved up to President, both of them people I had developed, not people I had to introduce to the job. My operating role at Bufficorn Ventures ended in August 2025, and I was invited onto the Investment Board as an advisor in 2025. My Chief of Staff role at SporkDAO ended in September 2024, and I was elected to its Board of Stewards in 2024. Nearly 250 law enforcement agencies chose, on their own, to accept myColorado as valid identification, nobody mandated that trust. People kept asking me to stay involved, or kept the thing running without me, after the job that first brought me into the room was already over.