Choosing a job is choosing an education. Most people choose it for the pay, and they get what the pay buys.
I chose mine for what they would teach me, and I chose small teams, because on a small team you do everything. You write the code, you load the printer paper, and you read the contract, because nobody else is there to do it. At a company of eleven I was the chief technology officer, and the title was the smallest part of the job.
My first lesson about size came at a large state agency. My work sat in the department that ran its computers, but I reported through human resources, and from that corner of a big house I learned that I did not like large companies. That was worth knowing, and a better offer would not have taught it.
Size was never the test. A publisher known for the classics was a big house, and I sat on a small team that wrote the systems that paid its authors, which meant reading the contracts those systems paid out. Whatever came back unsold from the stores went to the employees, since the books were already printed, and I took home five or six a week. A bestselling novelist once went camping with the staff. The seat gave me broad access to intellectuals and to the people who edited them. The analytics firm was my graduate school. It was large and well resourced, I led about twenty people on a Navy contract, and it had a library, and the mathematician who hired me read past the fact that I had no degree yet and handed me the key.
The test was who was in the room and what they would teach me. A small team where I touched everything, and a culture that treated learning as the job, will do more for a young person than a title. Surround yourself with people who make you better, and then look at what they actually do.
The best early jobs also teach what being wrong costs. My wife worked at Three Mile Island after the accident, with the damaged unit next door, and if she got it wrong she would have known at once. A close friend runs release management for government systems that people depend on. My uncle runs the maps for a water system, so that people can drink. None of us learned to hold a line in a classroom. We learned it from work where the line mattered. We picked the hard path, and the habit stayed.
For an investor, the lesson is about founders. A founder's early jobs are their graduate school, and the transcript is there to read. Ask which rooms they chose and what those rooms taught. For the founders without a pedigree, who never had the usual transcript, it is often the only one they have.
This is the author's account and is not investment advice.