MissionIn formation
Generalist Guild
A lifelong dojo for the human skills machines cannot inherit
Founder · 2025 -
The life's work in formation
A living portfolio
Things I've built, am building, and am still figuring out.
Some of these are companies. Some are practice communities. Some are essays. Some are bands. The throughline is the same: build things that flow with life, fruitfully and with zest.
Bucket
Companies
Current
Caliburn Technologies
The cybersecure OS for autonomous systems
Director of Operations · 2025 -
Deployed aboard Navy warships
Completed
Green Pants Studio
Delightful software that makes money
Founder and Chief Product Officer · 2018 - 2026
200+ products shipped, Austin and Dhaka
Exited
Vendidit
Marketplace platform for reverse logistics
Chief Product Officer · 2023 - 2025
Investor-backed marketplace, national press coverage
Exited
Pinwheel
The all-tool, no-toy smartphone for kids
Co-founder and COO · 2020 - 2021
$1M revenue in 9 months, hired 95% of the team
Exited
Skribe
Perfecting the Zoom deposition
Co-founder and Head of Product · 2021 - 2022
$1.3M raised, $5.4M customer waitlist
Completed
NXTBoard
Turnaround of an EdTech platform
Turnaround CEO · 2018 - 2020
Right-sized burn from $400K/mo to $65K/mo, 35-250% improvement on velocity, quality, and happiness
CompaniesCompleted
statUP
Skill tracking for youth sports
CEO and co-founder · 2015 - 2018
30,000 users. Backed by Landon Donovan.
CompaniesExited
9Lenses
Strategy assessment software for Fortune 500
First employee to Director · 2011 - 2015
150+ F500 consulting engagements. CEB Strategy Case Study of the Year, 2015.
CompaniesCompleted
Best Value Technology (DHS)
Homeland Security division built from scratch
Deputy Program Manager · 2009 - 2011
Lead proposal writer on $30M+ won bids
Bucket
Practice and writing
Practice and writingCompleted
Ethos Debate
Two thousand years of rhetoric, taught to teenagers who change
CEO and co-founder · 2005 - 2017
2,500+ students. 10 national champions. Book co-authored. 150,000+ words.
Practice and writingCompleted
Upside Down Debate
A Deeper Why to Persuasion
Co-author · Book
Classical rhetoric for the next generation of debaters
Practice and writingOngoing
The Isaiah McPeak Show
Entrepreneurial communication, startup coaching, rhetoric
Host · Ongoing
Field notes from the practice, in audio
Practice and writingOngoing
CEOWORLD opinion column
Out-of-touch leadership, executive hurdles, and field notes
Columnist · Ongoing
Plus essays on LinkedIn, Ethos, and elsewhere
Bucket
Community
CommunityOngoing
Franklin Park Big Band
Trumpet section. Conservatory training meets community.
Player · Ongoing
A community container, not just a band
CommunityOngoing
Evolve Social Wellness
Helping people build aliveness on purpose
Advisor and contributor · Ongoing
An experiment at the seam of wellness and community
CommunityOngoing
Debate coaching
Volunteer coach since 2005
Coach and mentor · 2005 -
150+ students mentored continuously, ten national champions
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