
5 Lessons From Losing $100K in My Agency
I Lost $100,000 in Under a Month. Here's What Rebuilt It.
November 6th, 2024. I sat my whole team down and told them the truth.
"Look — we are literally about to go out of business. I have $100,000 in credit card debt. I have about $25,000 of overhead to pay at the end of the month. You guys should probably just leave. Go get another job. I'll bring you back if things work out."
I meant it.
Eight weeks earlier I'd been cut from the NFL. The practice squad money I was counting on to pay down the debt never showed up. So the number stacked — 15k in August, 40k, then 70k, then 100k by the beginning of November.
Here's the part nobody expects…
That same business now does over $660,000 a month.
Not because I found a secret. Because I got violently specific about five things — and one of them shrank the entire company down to a single sentence.
If you're an agent or an agency owner who's had a month blow up in your face — chargebacks, agents leaving, a lead spend that didn't come back — this is for you. Over the past 3.5 years I've helped 550+ agents get to $40,000+ per month issue paid, and I've watched the same five lessons decide who climbs out and who quits.
Let's hop right into it.
Lesson 1: Failing Is a Prerequisite, Not a Detour
I'd heard this my whole life. I never GOT it.
Because in my head, the fall meant something was wrong with me. "Bro, how are you this person?" That's the voice that shows up when you didn't budget for failure.
Here's the thing…
Only about 4–5% of businesses ever hit $100,000 a month. Only around 5% of all businesses reach $1 million a year. Out of roughly 36 million small businesses in the US, the vast majority are solo operations under $50,000 annually.
So when you're chasing a number that only a few percent ever touch, what exactly did you think the price was?
Losing agents, eating chargebacks, watching a month fall apart — that's not evidence you're off the path. That's the toll booth on it.
The agents who quit aren't the ones who failed. They're the ones who thought failing meant something.
Lesson 2: Your Team Decides Whether You Survive the Bad Month
After the dust settled, I asked my team a question I was scared to ask.
"Why did you guys stick with me?"
They said: "We'd work for free just to work with you, because of who you are as a leader."
Your boy almost shed a tear.
I'd cut everybody's pay in half. They worked something close to full-time hours for part-time money. And they stayed.
Now — I know what you're thinking. "Tre, I don't have a team. I'm a solo agent."
Yes you do.
Your upline is your team. Your manager. Your partner. The IMO behind them. The YouTube channel you learn from, the coach you pay, the person whose script you're running on the phone. You did NOT learn this on your own.
Tough times don't build your team — they audit it.
You might think you have a great team. A hard month will tell you the truth in about two weeks.
Lesson 3: Everyone Going Where You're Going Paid the Same Price
This one hit me late because I had no direction. I was just… doing business.
Started the agency in 2022 out of pure necessity — I was training for the league and selling life insurance took too much of me. 2023 was our first full year: a million dollars in 10 months, averaging around $100,000 a month, all organic. No ads.
So I decided that was permanent.
Then I got to the league, stopped networking, stopped making offers — and found out very quickly that's not how any of this works.
Here's what I understand now. There's a list of prerequisites between you and your desired result, and it doesn't negotiate.
- You need to start dialing at a certain time.
- You need to buy a certain number of leads.
- You need to get the reps in.
Everybody who's standing where you want to stand did those things — and lost money learning them.
You're not special because you failed. You're finally normal.
Payroll used to feel enormous to me at $30,000 across the whole team including myself. Now it's close to $100K some months and I never blink. Same guy. Different phase. The phase was mandatory.
Lesson 4: The One Thing — How I Actually Climbed Out
This is the lesson that turned the business around, and it's from Gary Keller's book The One Thing: focus on the one most important thing, and the rest of the puzzle falls into place.
Here's exactly what I ran.
Rock bottom, I asked myself one question: What's the one thing people really, really want — and can I build an offer around it?
Then I went to work. Every single morning:
- 100 text messages to everyone in my phone.
- Then everybody sitting in my CRM.
- Follow up three, four, five times in a row. No pride. Zero.
There are people I work with today where I can scroll up and count how many times I texted before they answered. I don't care. Most agents won't do that because they're worried about how it looks.
And when I finally got them on the phone pitching my clever new high-ticket thing, they told me something I'll never forget:
"Bro, honestly — I just liked your business before you started doing all this other stuff. Just give me some leads."
That was it. That was the whole turnaround.
I stopped selling everything and started selling one thing: good leads.
Life got simpler immediately.
Apply it to your desk. Get really, really good at the intro. Then the vibe. Then pitching options. Then medical questions. Then objections. One thing, one thing, one thing — and they stack.
Lesson 5: Get Up Early. Push Every Day. No Gray.
Want to know the difference between the year I made money and the year I lost it?
In the 2023 off-season I was up at 4:00 or 5:00, working out, then in the business all day making offers and talking to people.
In 2024 I was getting up at 6:30 or 7:00, at training, on my team by 11:00. Going through the motions.
Same business. Different alarm clock.
When I hit rock bottom, I went back to 4:00–4:15, all my offers out by 7:00 a.m., and I talked to people all day long. That's when things started to compound.
Now run your own math. You get up at 6:00. Five minutes out the door, fifteen-minute drive, you're at the gym by 6:20. Lift at 6:30 for 45 minutes. Shower, phone, out by 7:35. Office by 8:00 — so you're actually dialing at 8:30.
You can legally start calling at 8:00.
So you just donated the best 30 minutes of your day to a snooze button.
Get up at 5:30 and you buy those 30 minutes back. Get up at 5:00 and you've got a full hour to prep, study calls, get your head right, be locked in with coffee ready to roll at 8:00 sharp.
Here's why the routine matters more than the willpower: if you leave yourself GRAY, you'll take the gray every single time. 8:00 becomes 8:30 becomes 9:00. No wiggle room, no drift.
The Trap: Grinding Without a One Thing
Now let me name the failure mode of my own advice.
Because the 4:15 alarm is what almost killed me the first time.
In 2024 I was working brutally hard — hiring staff like crazy, running ads I didn't understand, building a complicated offer that needed appointment setters and dialers I didn't have. I went from 50–60% margins to 30% margins with way more overhead. I'd already spent $50–75K on a software company that didn't exist a year later.
That wasn't laziness. That was effort pointed at seven things at once.
Early mornings applied to the wrong one thing just gets you into debt faster.
Pick the one thing first. THEN set the alarm.
Some Hard Questions Worth Sitting With
What time did you actually make your first dial this morning?
If your income got cut in half tomorrow, would the people around you stay — or were they only ever there for the good months?
Can you name your one thing in a single sentence, right now, without hedging?
And if a $100,000 hole showed up on your books next month… would you already know the first five moves, or would you just quit and blame the market?
FAQ
How do you recover after losing money in an insurance business?
Cut the overhead honestly, pick the one offer people already wanted from you, and go make offers by phone and text every single morning. I sent 100 texts a day to my phone contacts and my CRM, followed up four and five times, and rebuilt from the conversations that came back.
Is failing normal when scaling an agency?
Yes. Only about 4–5% of businesses ever reach $100,000 a month and only about 5% reach $1 million a year. Chargebacks, agent turnover and losing months are the price of entry, not a sign you should stop.
What time should a life insurance agent start dialing?
You can legally start calling at 8:00. So get up early enough that you're prepped, caffeinated and dialing at 8:00 — not walking into the office at 7:55 and starting at 8:30.
What is "the one thing" for a solo agent?
One skill at a time, mastered before you move on: the intro, then building the vibe, then pitching options, then medical questions. They stack. Trying to fix all of them in the same week fixes none of them.
The Bottom Line
I didn't recover from $100,000 in debt by getting smarter.
I recovered by doing fewer things, earlier, with a team that stayed — and by accepting that the fall was part of the fare.
You will have the bad month. What you do at 5:00 a.m. the next morning is the whole business.
The leads are infinite. Your discipline isn't — spend it on one thing.
— Tre
If you want a straight conversation about your numbers, your offer and what your one thing should be right now, book a strategy call at agentleadlab.com/schedule-a-call.
