The story behind The Vending Game
We didn’t get into vending because it was trendy.
We got into it because failure wasn’t an option.
A family was depending on us. The safe plan had fallen apart. We knew almost nothing about vending. What happened next became Two Brothers Vending—and eventually The Vending Game.
01
Before the machines
There was no business plan for what life had just handed us.
Our mother had died. Dr. Kerry L. Shipman was finishing law school while helping care for his son and younger brother, Koby. The bar loan that was supposed to provide financial breathing room was denied.
Rent and real life did not wait for the bar exam. With very little left, there was a decision to make: protect the last of the money and watch it disappear—or put it to work.
That decision is where the story begins. The details of what we risked, what went wrong first, and how we survived those early weeks are part of the story we reserve for the book.
02
The bet
We saw a problem. We saw an opening. Then we bet on ourselves.
A poorly stocked vending machine turned into an idea. We had no route, no inherited accounts, no vending mentor, and no special advantage. We started learning by doing.
That meant long nights, closed doors, wrong decisions, customer complaints, lost money, and the kind of mistakes that people selling “easy passive income” rarely talk about.
We kept going anyway.
What happened next
Those results are the headline. The decisions, mistakes, rejections, proposals, negotiations, route lessons, and operating systems that created them are the real story.
From operators to authors
The business became the book.
The Vending Game was written because we could not find the playbook we needed when we started.
We chose to document both the wins and the bad days: startup decisions, locations, machines, products, routes, proposals, scaling, loss prevention, and the business lessons that came from actually operating the company.
See The Vending GameThe point of the story
You do not have to know everything before you start.
You do need a reason strong enough to keep going.
Our story is not a promise that vending is easy or that everyone will make the same money. It is proof that preparation, persistence, customer service, disciplined execution, and the willingness to learn can turn an uncertain beginning into something real.