When Dennis Yu came through Minnesota, Henry Holm and I met up with him and Jack Wendt, the CEO of High Rise Influence. Dennis and Jack co-lead the company and build systems that power both High Rise and BlitzMetrics. Their collaboration consistently improves results for local service businesses—and this trip was no exception.
Launching the AI Apprenticeship Program
The main goal of our meetup was to build out the AI Apprenticeship Program. Dennis has spent years developing a Two-Sided Network: local businesses that need marketing help, and trained apprentices who can do the work while learning real skills.
The program has two entry points:
- Self-Starters: Applicants complete a one-minute video and repurpose a long-form piece of content into a blog post. These tasks test their ability to think critically and use AI effectively.
- Parent-Funded Track: Parents enroll their children to help them build skills that can be applied directly to a family business or a nearby company. Students earn while learning.
This structure lets young people develop real experience while helping small businesses grow.
Creating Content
We met up at SkyZone, messed around on the trampolines for a bit, and shot some dunk footage. Dennis has been using trampoline dunking to stay fit and has lost over 50 pounds, and dunking has been my thing for many years, so we teamed up for some tandem dunks I created on the spot.
After filming, we shifted to recording videos for the AI Apprenticeship onboarding and landing pages.
One segment stood out—Dennis sketched the Two-Sided Network on paper and walked through each part of the model. I turned that into a YouTube video that we now share as a core explainer for the system.
Planning the System
We set aside time to map out how this program scales. We covered:
- How to vet applicants
- How to train apprentices
- How to track outcomes for both students and the businesses they serve
We want this to be repeatable and valuable at every level—from a student’s first project to a full team managing campaigns for real businesses.
Ending the Day at Fogo de Chão
We wrapped the workday with dinner at Fogo de Chão. It was my second time ever eating there. During the meal, we continued refining parts of the program and discussed the next content pieces we’ll need.
Despite how much fun we packed into the day, we still made meaningful progress and got a lot done.
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