Richard Anderson · Operator · Advisor · Builder · Investor
I help people find and embrace the future they might not see clearly… yet.
Sometimes the vision is still blurry. I help you sharpen it, rally the right people around it, and build momentum — then hand it to those who'll carry it forward. Operator, advisor, builder, and investor for 20+ years.
Currently — CEO, Imagine IT
How I work
Envision
See what's possible before others do.
Rally
Pull the right people together around a shared future.
Ignite
Turn belief into momentum — strategically, and fast.
Release
Hand ownership to capable people so it thrives without me.
“I build to hand off, not to hold.”
Imagine IT
CEO since 2002 — through a rebuild, an acquisition, and a rebrand.
In 2002 a colleague and I bought a struggling consulting company and founded Next Level Cafe. Over the next decade we converted it from e-commerce, call centers, and custom development into a managed-IT business. It was acquired in 2012 and rebranded Imagine IT: security-first, relationship-based, serving small and mid-sized businesses across Minnesota, Kansas, and Michigan. I've been CEO the whole way.
Across that run it's grown from under $1M to eight figures — about 60 people, six locations, three states, with strong teams across sales and marketing, projects, the service desk, NOC/SOC, and admin, led by a lean four-person executive team. We adopted EOS in 2008 and have run on it since. I hold the CEO/Visionary seat in a leadership-only role — no day-to-day — and we've come through the 2008 downturn and COVID stronger than we went in.
Building
Ventures with their own names, teams, and trajectories.
Backing & advising
Trusted advisor for 20+ years — to MSPCFO, ConnectWise, ConnectStrat, and over 25 Managed Service Providers across the country. I borrow my best ideas from the best — and say so. How I work with leaders.
Some of the work I'm proudest of doesn't carry my name. I've sat in early rooms with founders — before they'd shipped a line of code — helping sharpen the idea. Several went on to build SaaS companies that scaled and later sold at strong multiples.
I back craft breweries and gathering places — Savage Tap, Lake Drive Tap — plus select commercial real estate. Places where people show up for each other.
What I look to back
Anything that brings people together gets a second look.
Giving back
Jack's Caregiver Coalition (advisor) — supporting the people who care for everyone else.
Off the clock
Private pilot · pickleball · taekwondo.
Let's build something worth rallying around.
