I already know we're going to be friends, because we probably already agree on a few things.
- That the standard career advice didn't age well.
- That building something of your own is starting to sound less like a fantasy and more like the only reasonable plan.
- That most online business content is either insultingly bro-coded or aggressively mompreneur-girlboss, and neither of them is for us.
I'm glad you found me. I have a feeling we're going to get along.
Now — let me actually give you something useful in our first email together.
You shouldn't quit your job. But you also shouldn't approach a new money-making opportunity as a side hustle.
Look, I lived through that era too. Side hustle. Digital nomad. "Work from anywhere online." Great.
The whole "make money online" notion isn't just dated — it's created a culture of side-hustling your way through mediocrity. You end up working two jobs (your real job and your side thing), busier than ever, with maybe an extra $10K a year to show for it. *Woopdie-do.* That'll cover the daily-latte habit we've decided not to quit.
Those are the two options most online business advice puts in front of you: either *quit dramatically and bet everything on the dream*, or *keep it small and casual so it doesn't disrupt your real life*. Both are wrong, and they're wrong in the same way: they both treat the business as a hobby until proven otherwise.
The path that actually works is a third one. The old-school way.
Start a business.
See, nobody talks about "online business" like this. That terminology has been quietly reserved for "founders." "Start-ups." "Entrepreneurs seeking capital."
But no. Starting a business is not just reserved for the people featured on *How I Built This*.
Starting with success in mind changes every decision you make from day one — *while you still have a job paying the bills*. You don't downgrade the business to fit the constraint of having a job. You upgrade your discipline to make both work.
Let me tell you how we learned this, because we learned it the hard way.
My husband Tim and I started Tripped Travel Gear in 2017. We had just finished a year-long around-the-world honeymoon and — well — run out of money.
We filmed all of it. Thought the YouTube thing might carry us into a permanent life of travel. It did not. Sixty hours of filming, traveling, editing, and publishing, in exchange for about $1,000 in revenue. That works out to roughly negative $5,000 a month in "profit." A fun little hobby during a beautiful chapter of our lives, but absolutely not a business.
Needing cash, we grabbed an apartment in Indiana and got real jobs again. Two people in their early thirties, collectively making less than $120K a year, working our day jobs and then working the new business from 5pm to midnight, every night, for almost a year.
Let me be clear about one thing. After that year of travel, we were *committed*. We had seen, firsthand, the life of digital nomads in Bali. We knew we could never settle for the standard American corporate life again. We were so committed that even at entry-level salaries, we were *turning down* job offers that paid more but demanded more hours.
Tim could walk to work and they didn't mind him leaving at 4pm from his outside software sales role. He made $40,000 a year as a 34-year-old in 2016 😵💫 but we took that trade on purpose.
And as you might expect, the commitment paid off.
In October 2017, just 9 months after day one of taking the first lesson in a $5000 Amazon course, our new business -Tripped Travel Gear- hit $100 a day in profit.
That was validation for us enough for Tim quit his job. We decided I should keep my job, which was remote anyways (which is also how we got to live in an RV for a year), because *somebody* had to keep a floor underneath us while the business was still proving itself.
Here's the part that matters. At every point, we treated this business like a business. Not like a hobby. Not like a side hustle. We invested our last dollars and hours into "giving this 100% to see if it would actually work".
We figured if we only gave it 30%, we'd only 30% know if it was going to work.
Within the first 12 months - again, of just thinking about this business - we were clearing $500 a day in profit.
Years later — after surviving Covid in the travel industry, Tripped crossed $10M in revenue in 2023 alone.
That hard first year — working jobs we didn't love and building something we didn't know would work — is the reason we now live wherever we want, work whenever we want, and earn whatever we want.
Most business stories that end in failure aren't failures of the business idea. They're failures at this specific structural choice. Either the founder quits too early and runs out of personal runway before the business catches up, or they keep it as a side hustle forever and never engineers in the conditions that would let it scale.
So here's what *The Exit* is for, and who I'm writing it to.
It's a letter on building a life on your own terms — through a product business of your own. About refusing the false choice between *quit dramatically* and *stay small*. About building something serious while still drawing a paycheck, because that's how the math actually works for someone with a mortgage, with kids, with student loans, with a real life.
I'm genuinely excited for the next stage of your life, and I'd absolutely love it if you'd reply and tell me a bit of your story — what you're hoping to exit, and what you're dreaming of building.
- Fin
