About The Jenn Files
You’re not looking for another newsletter. You’ve got eleven of them in a folder you don’t open. You’re looking for someone who’s actually built the thing you’re trying to build, or rebuilt the life you’re trying to rebuild, and who’ll tell you the truth about what it took.
You’re in the right place.
Most business advice comes from people who’ve read about building things. Theory and textbook cases. Then there’s real life. This comes from someone who’s done it. Under pressure. At scale. And while fighting for my life.
I’m Jennifer Makeeff. Two decades operating inside institutions where the cost of getting it wrong is on the front page. Strategic communications, advance, and operations at the highest levels of government and global enterprise. WH. DHS. HHS. Five continents. Then I built a service business from zero to seven figures, earned national recognition along the way, and exited.
I've worked from the seat where a misstep ends up on the front page of the press. I've worked from the seat where a misstep ends up on your own balance sheet and costs you dearly. I know both. They teach you different things, and you need both to build something that holds. Something that can't be broken.
That’s the street cred. Here’s what it bought me. The ability to look at a business, a decision, a moment of pressure, and reverse engineer what’s actually going on underneath it. Critical thinking that doesn’t fold when the stakes get real.
Those experiences broke a lot of what I thought I knew about business. Then life took a turn that put me in a fight I didn’t sign up for. The kind that strips you down to what you’re actually made of, and shows you which of your systems were real and which were performance.
I came out the other side with a different relationship to almost everything. Money. Risk. Time. The people I let close. What I’m willing to build, and what I’m not willing to trade for it.
The Jenn Files is where I write about that. Business, money, resilience, and grit. Without the motivational posters and without the MBA jargon. Just what works, what doesn’t, and what I wish someone had told me before I learned it the hard way.
Who this is for
You’re building something. A company, a comeback, a second or third act, a life that actually fits you. You’re somewhere between the first idea and forty million in revenue, and you’ve figured out that nobody’s coming to save you. You don’t need a pep talk. You don’t need another framework. You need someone who’s been in the seat you’re in, who’ll tell you what’s coming next, and who won’t pretend the hard parts aren’t hard.
If that’s you, you’re in the right place.
The mission
I’m on a mission to help rebuild Main Street. Modern day style. You have the ability. You have the tools. What you need is guidance from someone who’s actually done it, who can see what you can’t see from inside it, and who’ll hold the standard when it would be easier to flinch.
That’s what I’m here for.
Small business is the core of the American economy.
We’ve got a deficit of clear thinking and an excess of complicated systems. Overbuilt procedures. Technology stacked on technology.
The premise is simple. Elevate the care. Watch your business grow.
What I do now
I write here. I advise founders, operators, and executives navigating growth, transition, or what comes next. And I speak to rooms full of people who don’t need another talk about mindset. They need someone who’s actually built it.
What you’ll get
Weekly posts on building businesses that survive contact with reality. Financial thinking that goes beyond “just save more.” And the occasional personal essay about what it costs to build something worth keeping, and why it’s worth paying.
A few promises
The truth, based on two decades of seeing how things actually work and how they actually fall apart. Up close, behind the scenes, and in the moments nobody writes about.
What you can realistically do about that truth in your own business, your own life, your own bank account, and your own family.
I will make you laugh sometimes. The hard stuff is easier to look at when you can laugh at it.
I might make you cry sometimes. Some of this work is the kind that costs you something, and pretending otherwise is the lie that got us all here.
Hope. Real hope, the kind that has receipts. Practical steps. And the occasional kick in the pants when you need one.
So yeah. That’s me.
Small-town kid. WH. DHS. HHS. Global enterprise across five continents. Founder. Exited operator. Strategic advisor. Speaker. Writer. Dyslexic, didn’t figure it out until college. Licensed pilot. Published author. One fight I didn’t sign up for and survived. BIG breath. Someone who’s seen a lot, built a lot, lost some, won more, and lived to tell about it.
If you’re ready to build something that actually holds, let’s go.
