Chapter 3 - THE COMPANY I MARRIED INTO
Derek’s father founded Holloway Medical Transit in 1998 with two vans and a contract moving elderly patients between nursing homes and hospitals.
By the time I met Derek, the company had eighty vehicles across Virginia and Maryland.
Non-emergency medical transport.
Wheelchair services.
Contracted transfers.
Some federal work involving VA facilities.
Some state Medicaid billing.
Some private hospital agreements.
Derek’s father, Warren, died two years after our wedding.
After that, Derek became president.
His mother, Joanne Holloway, remained majority owner.
His younger sister Olivia handled compliance.
And I became controller.
That was never my plan.
I had a master’s degree in accounting and worked for a regional nonprofit.
Then Warren got sick.
Derek asked for six months of help.
Six months became three years.
I liked parts of the work.
Drivers.
Dispatch.
Hospital contracting.
Operational problems that could actually be solved.
I disliked the family structure.
Nobody clearly separated being a relative from being an employee.
Joanne could walk into accounting and demand a check because she “owned the company.”
Derek approved vendor payments verbally.
Olivia complained constantly that documentation was weak.
I considered her difficult.
That matters.
Because Olivia was right.
During my third year there, she discovered duplicate mileage claims on several federally reimbursed transport routes.
Not huge numbers individually.
Repeated patterns.
Trips that appeared in the billing system but not dispatch logs.
Derek blamed software migration.
Olivia wanted an outside review.
Derek refused.
They fought for months.
Then Olivia resigned.
The Holloway version was simple:
Olivia had a breakdown after their father died.
She became obsessed with minor errors.
She accused Derek of stealing.
She needed time away.
I believed that story.
Not completely.
Enough.
When I asked Olivia directly, she said:
“Rachel, if I tell you what I think is happening, you’ll tell Derek.”
I was offended.
“I’m your sister-in-law.”
“Exactly.”
She left the company.
Moved to Richmond.
Stopped attending family holidays.
Joanne called her ungrateful.
Derek called her unstable.
I did too once.
I hate remembering that.
Six months later, I left Holloway Medical Transit.
Official reason:
I wanted marriage and work separated.
Real reason:
I was starting to see the same billing problems Olivia had seen.
And every time I asked Derek about them, he made the conversation about loyalty.
“You think I’m stealing from sick people?”
“I’m asking why a trip exists in billing but not dispatch.”
“You sound exactly like Olivia.”
That sentence worked for a while.
Nobody wants to become the family exile.
So I stopped asking.
Then I resigned.
Derek said he supported me.
He threw a glass against the kitchen wall that night.
Not at me.
May you like
Never at me.
That was another distinction I used to survive.
