000016 - "Doing Nothing"

I’ve been out on my own for about five months. I wanted to reflect a bit about the indie life. It was necessary for me, but about time where I need it to be over.

The first question everyone asks is about finances. Most months my cash went down, some months my cash went up. It’s been down a bit overall, but I’ve more or less supported myself from my consulting relationships. Financially I can last quite a long time like this if I want to.

What I Worked On

Writing: I made the most progress on Twitter. I started the year with 0 followers and I think I had about 40 when I quit my job in August. Now I have almost 4,000. It’s come mostly from a few threads breaking down company business models.

This has helped me in a few ways:

  • I’ve met a lot of really amazing friends. Twitter is great for finding your tribe.

  • It’s lead to some fun business conversations with some really intelligent and notable people. Since my following didn’t come from memes / funny content, I’d like to think most of them are quality followers who like engaging with business and technology topics. This is awesome!

  • Reaching out to people who are part of the TwitterSphere is much easier. Followers isn’t completely a vanity metric

  • I have a better marketing intuition. Some of my threads weren’t good and I learned from them. Others were better and I learned from them. I feel much more confident with marketing copy.

Maybe the biggest takeaway from this is knowing that I love working on these types of threads! My Blue Apron thread in particular opened doors with several investors and operators who were close to the company. These discussions were awesome. I really like writing and talking about business, and this time period of writing validated that for me.

Stealth Startup Project: Experienced the up and downs of a stealth startup that never really went anywhere. I worked on marketing, design and partnerships, which translates mostly to talking to users and writing copy. The idea is in limbo now and we might pick it back up in the new year (we are still keeping it quiet publicly).

I’m considering getting a job now. Still up in the air. The time spent on this startup feels almost lost, almost wasted. Maybe others will feel differently, but since we never officially launched, what did we learn? What did we test?

[The answer to those questions are things like “ship faster” and “software is easier than hardware” and “make sure each member of the team is committed to the same goal”. But those lessons aren’t legible to A) future employers or B) VCs who I might need money from.]

Consulting: As I mentioned, to pay the bills I’ve been consulting. I even set up a single-member LLC only to shut it down a few months later. Turns out to be an accurate representation of my enthusiasm for this part of my life.

I had two long-term clients that I worked with for the whole time. One was for a Series A startup doing outsourced-CFO work and the other was for a bootstrapped startup doing operations / product work. It kept me sharp and I like both management teams. The other project I’m working on now is an industry report for a PE fund evaluating a growth-stage investment (which has been super fun and in an industry I love).

I had a few other opportunities pop up, but I overpriced my services to get out of the boring ones. It turns out that “being a consultant” isn’t quite as flexible as you think. You must pick a niche, market that niche and do lots of that kind of work. I don’t think I want to be an indie consultant long-term.

Learnings

It’s okay to not optimize your career. I figured out pretty quickly that IB wasn’t for me. But I also have to realize that the next thing I chose doesn’t have to be 100% right either! This is incredibly difficult and I’m sure anyone similar to me can relate. The ambitious-but-open-minded-and-ADD type. I want to work on the most challenging and important projects with the brightest and kindest people that fits my passion and makes me the happiest. Don’t we all…

The issue is that I have the financial and social capital to remain in career limbo for a loooooong time. If I don’t act, no one will.

Related to this, I also don’t know The Thing I Love yet. I’m only 23! I have a better idea than when I was 22, but I still am not 100% sure. Staying in exploration (vs exploitation) will do me well and reduce the existential burden of this next decision.

You mustn’t please everyone. I trust a lot of people. There’s advice that says this is good: “have friends from a variety of fields”. Hearing advice on Twitter makes it harder (even we all try to ignore it). Especially when you spend too much time on it.

Our actions are most determined by the people we admire and call friends. Friends provide a frame you can stick with. Viewing the world through a network makes the network that much more important. One of my goals for 2020 is to limit the amount of people I try to impress. It might mean getting farther away from some friends, but it’s the only way to keep my sanity.

Practically, picking 8-10 people who’s opinion I value allows me to answer a few questions I’ve been contemplating. Am I giving up by getting a job again? Is it foolish to start a business that has a prerequisite assumption of raising VC? Should my identity be tied to my work? Do I have a responsibility to work on problems that help the most people? The only way I keep consistent answers to these questions is to keep my friend group consistent.

These are rough ideas and I don’t review or edit. Feel free to unsubscribe at any time.