Caroline Calloway as the unreliable business partner

(written by lawrence krubner, however indented passages are often quotes). You can contact lawrence at:, or follow me on Twitter.

I’m not sure anyone else will understand this, but Natalie Beach’s story about working with Caroline Calloway very strongly reminds of some of the business partners I’ve had. The style of writing is more personal, maybe because they were young, or because they were friends first, or because they were women, but when I say that my experience of startups has been chaos, I’m using a euphemism for events like this:

I’d always known she couldn’t arrive at the airport at the suggested time, be bothered with classwork, take care of the King Charles spaniels she impulse bought, but I had held on to the fantasy that she didn’t care about that small stuff because she was busy with the grand plans that would change my life. I had built my whole career around my commitment to her persona — crafting it, caring for it, and trying my hardest to copy it, spinning out onto the streets of a strange European city as if the world existed to take care of me. But in Cambridge I didn’t see someone I wanted to be but a girl living with one fork, no friends, and multiple copies of Prozac Nation. Now I saw Caroline for what she was — a person in need of help that I didn’t know how to give.

My co-founder? When we were running out of money, he got increasingly bizarre. My first business partner would smoke weed, drink Red Bull, and stay up all night buying stuff on Ebay. During our first 4 years together, he spent $168,000 on Ebay. So this detail caught my eye in the Caroline Calloway story:

Caroline lived in King’s College, whose alumni include eight Nobel laureates and the inventor of the flush toilet. Students lived and went to class in stone Gothic buildings, which loomed over a great lawn that was brighter than I thought grass could be. My goal was to finish a draft in the two-to-three months I planned to visit, but the longer I was there, the more I saw the gap widening between the story we told and the situation on the ground. She rarely went to class, didn’t hang out with friends, and hadn’t started the dissertation she needed to graduate. She asked me to read the angry-professor emails she couldn’t bear to and just give her the gist. One night, I went to sleep on my air mattress while Caroline stayed at her desk buying homegoods, and when I woke up the next morning, she was still hunched over eBay in her fur coat, having purchased $6,000 worth of furniture. I went to the communal bathroom and sat on the stone floor with my knees to my chest. I told myself that everyone needed furniture, and it wasn’t my problem. But Caroline’s problems weren’t just my problems; they were my whole world, and so while I was a supporting character in the book, I cast myself as the hero in her life. I reached out to Cambridge about therapy, spoke with her mom about her prescription-pill use. When she wore the same lace gown for two and a half days, even sleeping in it, I forced her into the shower. When she arranged a loose pile of sleeping pills on her nightstand before bed, I swept them into my palm when she wasn’t looking. I pulled open her desk drawer to find a pen, and empty Adderall capsules skittered around like cockroaches exposed to light. The manuscript was due in six months, and my notes were just lists of funny British foods (Scotch eggs, juicy bits). I began to worry.

I say this partly in defense of Caroline Calloway. She got money from her parents, she ran a scam — this is fairly normal among the people I know who get a lot of money from their parents. Please don’t criticize Caroline Calloway as an individual, only criticize her as a class. It’s the whole class that’s rotten. My business partner was bored by all the normal tasks of running a business. The only thing he enjoyed was standing in front of a crowd and presenting himself as a “visionary”. Here is a video of him talking at the local Ted Talk in 2015:

In the Intro to How To Destroy A Tech Startup In Three Easy Steps I describe him like this:

Each person matters. Established firms will have a bureaucracy that can ensure some stability, even when an eccentric individual is in a leadership position, but when a company consists of just two or three people, and one of them reacts neurotically to challenges, the company is doomed.

From 2002 to 2008 I worked with an entrepreneur who had inherited a few million dollars when he was twenty-five. He admired musicians and considered the music industry glamorous, so he built a sound studio. It never made money. The bands that stopped by were broke. Those few who came up with a hit song mostly signed with a major label which, typically, had its own recording studio.

I met him in 2002 when his focus was shifting to the Web. I had developed some software that allowed people to create weblogs. Typepad, which fostered something similar to what I’d built, had just raised $23 million in funding. Surely we could do the same?

Our difficulties were self-imposed. We might go like maniacs on some project for four months, and when we were on the brink of unveiling it to the public, he would grow bored with it and move on to something else. The first time this happened, and I asked him his reasons, he improvised some arguments that sounded plausible; there were already too many startups doing the same thing. But this pattern, where he walked away from a project just when we were ready to introduce it to the public, repeated itself.

What led to this self-sabotage? As I met his whole family over the years I got to see the sad dynamics that ate at him. A modest business success would not be enough, in fact, it would leave him embarrassed. Only the creation of something as big as Google would suffice. But to grow that big, we would first need to be small, and that was the step he had no patience for.

As the years went by and he burned away all the money he’d inherited, the stress wrecked him. His self-image became increasingly grandiose. He told people that he was a visionary, someone who was able to tell what the future would look like. Late at night he would smoke weed and read articles on Slashdot and TechCrunch and then put together an amalgam of words that seemed full of the bright hopes of humanity, which he offered up as our marketing: “The Universe is fundamentally electromagnetic yet non-sentient, and we are sentient but only partly electromagnetic; the Internet is the ultimate harnessing of sentience to the fundamental forces of the Universe. Therefore our software will put you, our customer, in the driver’s seat of real-time conscious human evolution.” Later, when he wrote up our business plan, he put these two sentences in the executive summary. I’m not joking.

He had no capacity for internal dialogue. Only by talking to others could he hear his own thoughts. At our peak in 2007, we had eight people on our team. Sometimes I would look around the room when he was talking at everyone, and I would think, “If you add up what we pay all these people, we are spending $300 an hour so that he can have an audience.” When he was fearful about our chances of success, he would need to talk to everyone, and when he was euphoric about our chances of success, he would need to talk to everyone. Therapy would have been cheaper.

We had one modest success, in 2007. His girlfriend, a yoga instructor, suggested we build an online marketplace where yoga instructors could sell videos, as well as offer health advice. This site was an immediate success. Within the first month it was profitable. We were written up in all of the major yoga magazines. It seemed obvious to me that we should use the same technology to build a series of similar sites. We could do a site devoted to cooking videos, another devoted to tennis, another devoted to golf. Indeed, just a few years later, the team behind did exactly what we could have done.

My business partner, however, was enraged by the success of the yoga site. He had burned through several million dollars chasing ideas that he felt were “visionary” and then his girlfriend came up with a simple idea that turned into our one true hit. To this day, it remains a popular yoga site. We could have built an empire around that site, but instead his girlfriend’s success left him bitter.

I finally ended the partnership in 2008 after I had decided that I could never build anything successful while I worked with him. A decade later, he has not yet built the giant success that he fantasizes about, but he is still active in the local tech scene. If you run a Google search for “Charlottesville Ted Talk Archaeomediaology,” you can see that he is still trying to sell his vision.

Anyway, Natalie Beach did a good job with this story. Off topic, I am curious if she was influenced by any tropes from other famous two person friendship stories, such as “My Brilliant Friend” by Elena Ferrante? Or a bit of Great Gastby, with Gatsby creating the illusion of a beautiful life, and Nick Carraway narrating the truth. Not that Natalie Beach indulged in any stereotypes, but I know, personally, when I write, I’ve got tropes from 100 books in my head, I’m aware when I write something that is somewhat similar to something that was written in the past.

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