On Money, Not Having It, and Writing About People Who Have a Lot of It

There’s a fine art to reporting on sketchy companies with billions while making $13 an hour

Photo: Claudio Schwarz | @purzlbaum on Unsplash

Ihave never had a lot of money. And I’ve also never been particularly good with money. It did not occur to me to get better with having money, perhaps because it did not make sense to me to learn how to be better about handling money I didn’t have.

Why would I learn about investing in the stock market, for example, when every dollar I made was going toward rent or paying off my student loans? Does the stock market let you invest your leftover $40 after taxes and expenses? (Do not answer this question. I still have not put any money into the stock market, in part out of a misguided belief that eventually I will go back to “reporting,” and it will be ethically murky for me to own stock in a company I could potentially cover. Also, again, I do not have any money with which to invest.)

In 2014, when I started covering venture capital funding, multimillion- and eventually multibillion-dollar companies, I was making $13 an hour. A few months later, when I finally got a job offer, it was for $40,000 a year plus the potential of a $5,000 annual “traffic bonus.” Again, it was 2014.

I spent half of the first year and most of the second year talking to people smarter than I am who would let me ask them questions about tech. I wrote about companies like Uber, which seemed to be able to command an insane amount of funding and, subsequently, press for raising that money. Uber raises $1.2 billion! Uber is raising another $2 billion! Uber raises $1.15 billion! Yes, there were other Uber headlines during this time. Bad ones. There was Operation SLOG, essentially Uber’s playbook for sabotaging Lyft. There were the drivers protesting Uber’s claims that they could make $90,000 a year driving for Uber. The drivers I spoke to were barely making minimum wage.

I had no qualifications to write about business, tech, or finance news. I was merely a 22-year-old idiot—a fact reinforced to me in rude off-the-record phone conversations with Uber’s PR flacks — but it seemed glaringly obvious to me, an idiot, that what was happening here wasn’t sustainable. Company raises a kajillion dollars. Company uses funding to subsidize new growth. Organic growth can’t match the growth spurred by the funding. Company loses money. Company raises more money. I didn’t know anything about anything, but it certainly didn’t seem to add up.

Surely someone smarter than I am understood these numbers. People on the markets desk at work started asking each other, jokingly, whether we were at the top. The top of the market, or the top of the bubble? (I think this post on Business Insider about a day-trading Uber driver is a quintessential encapsulation of “the top.”)

I was merely a 22-year-old idiot. But it seemed glaringly obvious to me, an idiot, that what was happening here wasn’t sustainable.

Companies that were valued at $1 billion were called “unicorns.” (From what I could surmise, a “private market valuation” was just a number that investors and founders agreed a company was worth.) People started saying “unicorns” with a straight face. They called them this because they were supposed to be rare. Maybe they were at one point, but eventually they became more and more common. I too started to say “unicorns” with a straight face.

It was a period of irrational exuberance that followed a formula: Have an idea that could be construed as at least tech-adjacent—does it have an app? A platform? Great, it’s a tech company. Then get someone to fund your idea, have it written about in the tech press, and if you’re lucky and iconoclastic enough, maybe you’ll be parodied on Silicon Valley, a series on HBO about Silicon Valley. Don’t worry about an exit strategy. Your exit strategy is to tease an eventual IPO at a Fortune or Wall Street Journal event and continue to raise more private funding.

This was a time when it seemed fairly easy to get people to write about you simply for raising money. That was the whole story. These pitches filled my inbox. The pitch was that a company I had never heard of had raised $8 million. Did I want to write about this news? We got requests to write so many of these stories that we had to develop a rule that we wouldn’t write about them unless they were exclusives or could be made more meaningful in the context of other actual news.

It felt very dissonant to write about a company raising $10 million and dismissively think, “That’s really not that much money,” because the shock value of those sums almost instantly wore off for me. Every company wanted you to write about how they were raising $10 million, and then I’d go and forage in the work kitchen to scrounge together lunch from the snacks there because I had $50 in my checking account until payday.

I went to dinners and parties hosted by venture capital firms and by startups funded by these venture capital firms. I met some VCs and other reporters and mostly listened because I didn’t have much to say, and I watched the way that money could smooth out the wrinkles in the relationships between people with money and people without it.

This was a time when it seemed fairly easy to get people to write about you simply for raising money. That was the whole story.

These were impossible sums of money for me to conceive of — $10 million, $50 million, $100 million, $1 billion — but somehow they felt even more impossible while I stared down the balance of the $60,000 debt I owed Syracuse University, which felt both literally smaller and symbolically larger than all of these other numbers I saw every day.

How very strange, I think now, to have been writing about this very frothy era of VC funding. There were gazillions of dollars sloshing around in the coffers of all of these “Uber for influencers” and “Airbnb for purebred dogs” startups. Even stranger was to think that I was writing about these companies as I was barely scraping together the $450 I owed in rent for what was essentially a closet in Bushwick.

At some point I stopped writing about the funding. Everything had been a funding story, and then nothing was. The funding craze morphed into mega-rounds for the biggest tech companies. Then I stopped writing about tech, and some of those companies went belly-up or went public, and the whole fairy tale of that era sort of came to a halt.

Today I am a little better about money. I have a savings account; I’m somewhat financially literate. But I still read an occasional headline about a company raising $5 million and catch myself thinking, “That’s a small round,” and that is how I know that my brain still hasn’t returned to normal.

i’m a freelance writer and editor. you can also read me in places like the new york times and vanity fair.

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