Prologue
The Most Personal Decision You’ll Ever Make
entrepreneurship, career decision, personal, values, self-knowledge
Who I Am and Why I’m Talking to You
Let me start where you probably weren’t expecting me to start — with a statistics class.
My name is Dan Green. I graduated from Michigan Tech in 1983 with a degree in business administration, and for the last four decades I’ve been working at the intersection of finance, lending, and technology. Credit unions, mortgage banking, FinTech startups. I’ve spent roughly half my career in residential mortgage, a quarter in credit unions and trade associations, and another quarter in FinTech. In almost every one of those roles, I was the person inside a larger organization trying to build something new from scratch. There’s a name for that — corporate entrepreneur. I’ll come back to it.
But first: the statistics class.
The Summer of ’82
Ask me what my favorite course at Michigan Tech was, and I’ll tell you every time — Econometrics. That surprises people. It shouldn’t.
The summer of 1982, I decided I was going to teach myself to understand data. Not just how to run regressions, but how to think about what data is actually telling you, and — maybe more importantly — how to use it to make a point that people will actually believe. That’s a different skill than knowing the math. You can know every formula in the textbook and still be terrible at making a case with numbers. Econometrics forced me to think about both at once.
I had no idea at the time that this was going to matter. I was a twenty-something college student trying to get through a hard course in the summer heat. But it turns out that the ability to look at data, understand the relationships inside it, and use it to tell a story — that skill shows up everywhere in business. It showed up when I was underwriting mortgages at scale. It showed up when I was pitching a new product to a board of directors. It showed up when I was trying to convince skeptical investors that a FinTech idea was worth their time.
The lesson I’d offer you: the skills that end up mattering most are rarely the ones you expected to need. Your job right now isn’t to optimize your resume for the next internship. Your job is to learn how to think.
A Career Doesn’t Go in a Straight Line
I didn’t plan to spend forty years in financial services. It happened because of a sequence of decisions — some deliberate, some accidental, most of them made with incomplete information. I moved between industries when the opportunity felt right. I took roles where I was building something, even inside companies that already existed. And I kept going back to the same fundamental questions: What problem is worth solving? Who’s going to care? Does this actually work?
Those questions don’t change whether you’re starting a company from scratch or trying to launch a new product inside a bank. The entrepreneurial instinct is the same. The skills are the same. The risks are different in degree, but not in kind.
That’s really what I want to talk to you about — not entrepreneurship as this abstract, heroic thing that only certain people get to do. But entrepreneurship as a set of decisions you’re going to face, probably sooner than you think, regardless of which path you take. Some of you will start companies. Some of you will join early-stage startups. Some of you will work inside established organizations and spend your careers trying to make them more innovative. All of you are going to have to understand how new businesses work, because every business you ever work for is going to be competing against one.
So before we talk about business plans and value propositions, let’s start where all of this really begins — with you.