WHO’S TREVOR
Hi, I’m Trevor.
I’ve started several businesses. A lot of them have failed.
All of them have taught me something.
I’ve spent 20+ years learning, building, failing and doing it all over again. The first time, I started with nothing. No lessons, no playbook. I built, I failed, I got back up. The next time I started a little higher, with a few lessons in hand. Then I failed again, learned more, and started higher still.
Farms, trading floors, helicopters, heliports, tourism, software, manufacturing, service businesses. Zoning boards, city, state and federal agencies, lobbyists, lawyers, engineers, and every kind of red tape you can imagine. I plowed through all of it, and every round stacked more lessons. Over time those failures turned into a foundation, and things started to work.
I’m not an expert at anything, and I’m not here to tell you how to do it. I’m still learning every day. I just have a lot of scars, and a lot of tools and resources I picked up along the way. I’d rather share them, and hear your stories too, so we can all get where we’re going a little faster and with a little less pain.
The honest numbers.
Most of them came with a lesson attached. Some of them cost a lot.
12
businesses started
4
still running today
$20M+
capital raised and put to work
40+
investors who took a chance on me
$20M+
in revenue to date
100K+
passengers flown, the largest helicopter operation in the Midwest
1st
and only private heliport approved in a major U.S. city
20+
years of building, failing and learning
THE STORY SO FAR
Down, then up. Over and over.
2004
The farm
Helped start a fall festival on our family farm. My first lesson in what makes people have a great day. My aunts run it today.
THE 2000s
The trading pit
Traded as a local in the lean hog pit at the CME, started a managed futures fund called Alpha Group Trading, and ran the farm at the same time. Learned about risk, mostly by losing.
2010–2011
Stuck in traffic
Sick of sitting in traffic on the drive to the farm, I learned to fly and bought my first helicopter.
2011–2015
Fighting City Hall
Started flying tours out of Chicago Executive Airport (the old Palwaukee) in 2012 while chasing the city for a downtown heliport. It took until 2015 to get it approved.
2016–2019
Learning everything the hard way
Opened downtown in 2016 and grew into the largest helicopter operation in the Midwest. Made every mistake along the way: wrong vendors, wrong structure, fights with the city, the federal government and just about every agency there is. Slowly figured it out.
2019
Doing it right, take two
Took everything I’d learned and rebuilt from scratch as Midwest Aviation. New investors, a clean structure, a new heliport. We moved in on January 1, 2020. Everything was finally set up right.
2020
Losing it all overnight
Then COVID. It was gone.
2020–2022
Fighting the world
Winding it all down took two years: bankruptcy, creditors, lawyers. Probably the most I’ve ever learned in one stretch. At the same time I was hustling to survive: boat charters, importing PPE, starting an advising business, applying for jobs.
2021–2024
Finding my way
Helped rebuild Blue Hawaiian after COVID. Worked with Anchor and SITE Technologies. Applied at the aviation companies that looked like a perfect fit, and nobody wanted me. I’ll be real, I was pretty down. The whole time I kept tinkering with Taggable on the side.
2024–2026
Showing what I can do
Got the chance to build FoodCycler’s commercial division from zero, and did. Kept building Taggable at night and on weekends.
2026
All in, still learning
This summer I left FoodCycler and went all in on Taggable. I still run The Chicago Captain, and now Failure’s Fortune. Still building, still failing, still learning.
WHAT 20 YEARS TAUGHT ME
Farming, trading, aviation, tourism, food waste, software, boats. Very different worlds. Every one came down to the same four things. I’m still working on all four.
People.
Every business is a people business. Find good people, inspire them, motivate them and keep them.
Processes.
Find the simplest way to get it done, then document it so anyone can learn it, repeat it and scale it. You can’t do all the work forever.
Action plan.
See where you are and where you want to go. Connect the dots with small, doable steps, then take the first one.
Learning.
No one is coming to save your business. Spot the next skill you need, learn it fast, then hand it off.
2011 TO 2020
My business master’s degree.
Ten years, three vertically integrated companies, one downtown heliport, and hundreds of failures along the way. Every lesson I use today came out of them.
My Chicago Helicopter Experience.
Most people around me today never saw this chapter. For ten years I ran Chicago Helicopter Experience, and it became the largest helicopter operation in the Midwest.
We bought land on the Chicago River, fought City Hall for four years, built a private heliport downtown, and flew more than 100,000 people over the city.
It’s where I learned almost everything I know about business, mostly by getting it wrong first. Aviation, real estate, government, fundraising, marketing, software, hiring, crisis. And then I watched it all disappear in 2020.
WHAT IT TOOK
10+
years running it
100K+
passengers flown, without an incident
17·3·3
city, state and federal hearings for the heliport
11
agencies that had to sign off
2
FAA air carrier certificates
29,000
gallon fuel farm on the Chicago River (the limit was 2,000)
7
aircraft types tried before we got it right
50+
full-time team, plus seasonal crew
1,100+
five-star reviews
At one point Groupon’s single biggest vendor, and the Mayor’s go-to way to show off the city.
THE COURSES
What ten years of helicopters taught me.
FROM THE ARCHIVE
AS SEEN IN
Almost everything I’ve built since came out of those ten years.
WHAT CAME OUT OF IT · RUNNING TODAY
Taggable
Guest photo, video and on-site revenue for tours and attractions. “The best day of their trip. In their hands before they leave.” It started as the photo system at our heliport.
taggable.com →The Chicago Captain
Private boat days on Lake Michigan, captain included. I started it during COVID to keep the lights on.
thechicagocaptain.com →
Failure’s Fortune
This. Plus what used to be TJH Advising: if you want help building, fixing or rebuilding something, let’s talk. Heff Holdings holds my investments and assets, including the boat.
Get in touch →EVERY BUSINESS SO FAR
What it was. What happened. What it taught me.
01Susanna Farms2004–2013FAMILY-RUN+
Fall festival on our family farm. My aunts run it now.
What it taught me: [YOUR LESSON]
02Alpha Group Trading2009–2014CLOSED+
A managed futures fund trading livestock and ag spreads.
What it taught me: [YOUR LESSON]
03Chicago Helicopter Leasing2011–2019CLOSED+
Owned the aircraft and leased them back to the operating company.
What it taught me: Own the asset when you can. [REFINE]
042420 S Halsted LLC2011–2019CLOSED+
Bought the land, won the city approvals and built the downtown heliport.
What it taught me: If you’ll grind through the red tape, the red tape becomes your moat. [REFINE]
05Chicago Helicopter Experience2011–2019CLOSED+
Tours and charters. The largest helicopter operation in the Midwest.
What it taught me: [YOUR LESSON]
06Midwest Aviation2019–2020CLOSED+
The rebuild: new structure, new investors, new heliport. Then COVID.
What it taught me: You can do everything right and still get wiped out. Plan for what you can’t control. [REFINE]
07Bioworks Global2020–2021CLOSED+
Imported PPE from China for local hospitals and schools during COVID.
What it taught me: See the window, move fast, and know when to close it. [REFINE]
08The Chicago Captain2020–nowRUNNING+
Private boat days on Lake Michigan.
What it taught me: [YOUR LESSON]
09Heff Holdings LLC2020–nowRUNNING+
Holding company for my assets and investments.
10Digital Media Share / Taggable2020–nowRUNNING+
Guest photo, video and revenue platform for tours and attractions.
What it taught me: Duct tape gets you to market. It won’t get you to scale. [REFINE]
11TJH Advising2020–nowRUNNING+
Advising founders and operators. Now part of Failure’s Fortune.
What it taught me: [YOUR LESSON]
12FoodCycler Commercial2024–2026BUILT & EXITED+
Built the commercial food-waste division from zero.
What it taught me: “It’s basically done, just sell it” usually means it isn’t. [REFINE]
REBUILT AND HELPED
WHAT I WANT TO SHARE
The best thing I have now isn’t a business. It’s the people, tools and playbooks I’ve collected from getting things wrong. I want to put all of it on the table.
Lawyers and accountants who’ve saved me. The AI setup I use to run three companies. Systems for hiring, ops and sales.
See upcoming events