This is a now page. It’s the short version of what I’m up to lately.
Last Updated April 2026
Irreplaceable
Irreplaceable is an education platform teaching students and professionals the human skills that make them stand out in an AI-first world.
I’ve spoken to and taught over 10,000 people in 60+ countries about the skills needed to become Irreplaceable in the age of AI.
Austin Capital
I continue to lead Austin Capital, a single-family office focused on operating, incubating, and investing in fintech and financial services companies.
Current investments and operating companies include Spec Fi, Fintech Automation, Unifi, Austin Capital Trust, Modern Rails, DevBase and many others.
We’re investing in community banks and moving forward with launching our own Credit Union.
Commonground
Commonground is our farmland leasing marketplace with embedded crop insurance.
We’re building tools that make farmland leasing and insuring more accessible and transparent for everyone involved.
Building Communities
Bringing people together is still my favorite thing to do.
- Outcove: our invite-only retreat for founders and investors, described as Allen & Co meets Burning Man. We hosted gatherings in Utah and Hawaii and continue to expand the community. I went deeper on Outcove and “the super connector advantage” on The Jess Larson Show.
- Outcove One: an invite only retreat specifically for family offices.
- Weekend of Man: a highly vetted adult “summer camp” focused on pushing yourself through epic challenges and personal growth.
Writing About AI, Leadership & Human Skills
I’ve been writing often about entrepreneurship, leadership, and the people who build things that last. Recent pieces I’ve gotten the most response on:
- Workday’s CTO Left to Become an Engineer at Anthropic, a real-time signal of how the talent migration to AI is happening
- How Din Tai Fung Became a Category-Defining Machine, doing $27M in revenue per location vs. McDonald’s at $3.9M
- Why Your Oldest Friendships Might Not Be Your Deepest, what I’ve been calling the Friendship Infrastructure Dilemma
- How SaaS Companies Destroy Customer Relationships Over $3,250, after a personal experience with Gusto that surprised me
- How Stephen Ross Built His Fortune and Lynda Resnick’s billionaire brand-builder playbook
Click here to read them on my blog.
Staying Curious
A few other things I’m spending time on:
- Participating in YPO globally
- Working on my private pilots license
- Exploring how AI reshapes work, creativity, and identity
- Training for a 1/2 Ironman
- Doing a 10 year Harvard Business School program through YPO
Board Work / Advisory
- Falcons Club a private network for the worlds most iconic property owners
- Spec Fi a financial technology company for high risk / hard to bank
- Frequent Fan a loyalty platform for sports and live entertainment
If you want occasional updates on what I’m building and the interesting people I’m meeting, you can join my monthly newsletter by clicking here.