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About The Jenn Files
Most business advice comes from people who’ve read about building things. This comes from someone who’s done it — under pressure, at scale, and while fighting for my life.
I’m Jenn Makeeff. I spent years in presidential-level advance, communications, and operations — the kind of work where failure isn’t a learning opportunity, it’s a front-page headline. Then I built DC Dog Sitter from zero to seven figures and exited.
Those experiences broke a lot of what I thought I knew about business. They also showed me what actually holds — the systems, the relationships, the instincts that don’t fold when everything else does.
The Jenn Files is where I write about that. Business, money, and resilience — 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
Entrepreneurs, small business owners ($0 to $40M), and people who have an idea and want to build something real. You don’t need a pep talk — you need someone who’s been in it and can tell you what’s coming next.
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.
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