The Kentucky Derby has been run for 150 years.
Then it happened: for the first time, a woman trained the winner and a Latino jockey rode one home. Both barriers, gone in a single running.
I’m not a horse person. I watched the coverage and felt the same thing every business builder feels when they see a “first”, a fast, complicated mix of finally and ouch and what would that take.
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Take the free scorecard →Here’s the part nobody covers when a “first” lands: what it actually required to get there. And why most business owners give up two layers above where the breakthrough actually lives.
“Firsts” don’t happen on a deadline
Every business book sells you a 90-day plan. Every coach sells you a 6-month transformation. Every program sells you the breakthrough that’s right around the corner.
Real firsts take decades.
Not because the work itself takes decades. Because the prep work, the unsexy, unglamorous, underpaid, nobody-clapping years, runs longer than anyone shows you.
The first woman to train a Derby winner didn’t show up at Churchill Downs out of nowhere. She’d been training horses for 30+ years. The first Latino jockey didn’t get the mount on Derby Day by accident either. He’d been riding professionally since he was a teenager.
The Derby was the visible part. The career that made it possible? Invisible.
When you start a business, you’re starting that career. The breakthrough, if it comes, is decades from now. The work is now.
Most people quit at the part that’s actually easy
Here’s the cruel part. The hardest stretch of any business isn’t the start, too much energy, too much new. It isn’t the breakthrough, by then you’ve earned it. It’s the middle.
Years 2 through 7. The part where the new wears off, the breakthrough still isn’t visible, and the people around you start asking when you’re going to get a real job.
I did $400,000 in revenue in my first 8 months of my first business. Sounds like a flex. It wasn’t, that revenue came with $370,000 of cost. The next two years were where it actually had to work, and that’s where most operators give up.
What kept me going wasn’t grit, wasn’t motivation, wasn’t a vision board. It was math. The unit economics worked. The next iteration’s unit economics worked better. The third one better than that.
Vibes don’t carry you through years 2-7. Numbers do.
What firsts actually require
I’ve watched a lot of “firsts” land lately. Beyond horses, the first Black woman to take a SaaS public, the first Latina founder to scale to $50M ARR without VC, the first contractor in my market to run her business without working Saturdays.
The pattern shows up every time:
- Decade-plus of working at the craft itself. Not “in the industry.” At the actual thing. Riding the horses. Training the horses. Quoting the kitchens. Auditing the books. Sweat at the level of the work.
- A specific math model that survives. Not a vibe, not a dream, a unit economics model with a margin that compounds. If your business model loses money on every transaction, no amount of “firsts” energy saves you.
- A bench of people who saw it before the public did. Mentors, peers, employees, partners, humans who recognized the trajectory while it was still invisible. Look at any “first”, there’s a network around them.
- An iron tolerance for the middle years. The years 2-7 stretch where it gets boring, tedious, and underpaid. Most “firsts” stories skip this part. It’s the actual story.
- Specific instrumentation. Not “I’ll figure it out.” A plan, a calendar, a budget, a metric, a system. The instrumentation distinguishes firsts from also-rans more than talent does.
What this means for you
If you’re 18 months into a business and the breakthrough hasn’t come, that’s normal. It’s also the easy part of what’s ahead.
If you’re 5 years in and still grinding at the middle, you’re closer than you feel.
If you’re starting today, buckle in. The work is the work.
The shortcut isn’t a course. The shortcut isn’t an AI tool. The shortcut isn’t a guru’s framework. The shortcut is math you can defend at every stage. Pricing math, margin math, time math, leverage math.
Build smarter so you can stay in the game long enough to scale faster.
→ Run a free Profit Audit on your business, 10 minutes, you’ll see whether your math survives years 2-7 or whether it’s already breaking.
Resources
- Churchill Downs press archive on the 2026 Derby winners: the official record of who won and the trainer/jockey credits
- Forbes — “The 21 Female Founders Building Billion-Dollar Companies”: recent female founder firsts (search Forbes Women)
- HBR — “Why Some Businesses Survive the Hard Middle”: research on the years-2-7 attrition curve in service businesses
- My Profit Audit: free, 10 minutes, runs the unit-economics math on any service business
