Five Fs. Zero f*cks. Start here.

Our lives are impacted by often-unseen forces and systems. Those systems have incentives, sometimes incidental, sometimes intentional. Learning the playbook gives you the upper hand in trailblazing through a chaotic, complex world.

All the tools to thrive are right outside your door. It’s time to learn the rules. Let’s play.

Jessi Roesch seated in a pink patterned dress, holding a husk of corn 7,000+ readers Austin, TX
Let’s play

Five Fs. One next step each.

You landed in the weird intersections of my work, probably because you work in the intersections too. Pick a path that feels natural.

01 Jessi holding a bunch of kale, seated beside a disco ball

Food

Human health and planetary health come together at your plate, shaped by systems in your city and beyond. My weekly-ish newsletter shows you how with practical steps for navigating the inches right in front of you.

Read the newsletter
02 Jessi seated in a utility vehicle in a green field under a big Texas sky

Farms

Land changes hands whether or not there’s a plan. Downland helps you the plan to access land, from hobby farm to homestead, or pass yours down to the next generation. Build your plan for your land.

Join the land list
03 Jessi pressing a dumbbell overhead in a gym

Fitness

Your food is the fuel that moves you, and Jessi can help move you too. With a decade of coaching, she loves working with beginners, athletes who’ve hit a plateau and women navigating perimenopause and beyond. Now booking weekends only.

Book a 1:1
04 Jessi speaking into a handheld microphone at an evening event

Finance

Fifteen years in lending, sales and startups, Jessi has led international teams, managed P&Ls up to $40MM, raised institutional capital and scaled with startups from pre-seed to Series C. She gets in some special rooms. The paid tier of Chaotic Natural is where I tell you what I see.

Get the analysis
05 Jessi on a panel with a microphone, mid-gesture

Future

Keynotes, panels, workshops and podcasts. I make complex systems thinking usable from executives to everyday eaters. I’m pretty funny too.

Book me to speak
The throughline

Chaotic by nature. Deliberately free.

I’ve spent a career walking between rooms that don’t talk to each other. Policy hearings and CrossFit boxes. Lending desks and farmers markets. VC pitch meetings and 5 a.m. sessions where somebody is learning to deadlift for the first time at forty-seven.

It took me an embarrassingly long time to notice that the same three or four things are broken in all of them, and that the same handful of moves tend to work. Business transition is behavior change at a generational scale. So is learning to squat.

Nobody here is behind. People only know what they know, and you deserve to know more.

More about me
Receipts
$10B+ Underwritten in commercial lending
15 yrs Inside the system I’m trying to fix
7,000+ Readers of Chaotic Natural
5th In Texas, Olympic weightlifting, 2024
Speaking

Put me in a room that doesn’t talk to the other rooms.

Keynotes, panels, workshops, podcasts. Food systems, farm succession, capital access, behavior change — and how those four are the same story told to different audiences.