Effort is rarely the problem. Where it goes usually is.

I wasn't qualified for most of the jobs I've had. Six roles at one church, a photography business with my wife, and a video agency with a friend. Turns out that's a decent way to discover what actually works.

  • The hire I made too early

    Adding a person is the most visible fix available, which is why I reached for it before I understood the problem. This one is still resolving.

  • What I haven't been able to kill

    I built a framework about choosing what to eliminate. Here is everything still running.

  • Entering cold, carrying everything

    Four disciplines with no background in any of them. What actually transferred.

Every piece has a second reading: the constraint, the call I made, and the part I would take back. Hover a card, or click Notes to pin it.

001 / Venture

Cheyenne Schultz Photography

With Cheyenne

handed off
002 / Venture

HypeKick

Co-founded 2019 · with David

active
Constraint

Two founders doing the execution to protect the margin.

Decision

Stayed small and hired contractors per project.

What I'd change

The thing keeping the margin is the thing keeping us in the work.

003 / Film

Bailey Nurseries

HypeKick · 2026 · 2 shoot days

active
Constraint

One location, one season, no reshoot window.

Decision

Shot the interview first so the b-roll could answer it.

What I'd change

Locked the script two weeks earlier. We paid for that in the edit.

004 / Film

Movement Mortgage

HypeKick · 2025 · campaign

active
Constraint

Sixteen deliverables, one shoot day.

Decision

Built the edit structure before the shot list.

What I'd change

Should have cut four deliverables instead of compressing sixteen.

Underpin
005 / Venture

Underpin

2025 · underpin.works

active
Constraint

Had to sell before I had hours to sell it.

Decision

Led with a paid diagnostic, not a free consult.

What I'd change

ICP too narrow on size, too broad on vertical.