Optionality is a mind virus

Plus a Tech for Abundance event, extrapolating AI, and a new Slow newsletter

In August 2021 I wrote “Against Optionality” about tech’s obsession with optionality (things could be better elsewhere) and what that preoccupation ultimately costs (focus and compounding). Four years on, it’s worth revisiting that premise:

The tech ideal of being a bi-coastal, sexually-unmoored IC with a paid newsletter and a scout fund is fundamentally about optionality and flexibility. Total freedom with fallback options and alternatives aplenty. That desire for optionality and flexibility is a reflection of the belief that there might, at some point in the near future, be something/someone better to do/be.

Some of the particular watchwords and trades have changed in the last four years (scout funds and dating are out, pump groups and vibe coded micro-SaaS are in) but the feeling is still the same and the general trend has only intensified. This is an increasingly prevalent, potentially permanent element of startup culture. It’s a brainworm that has only burrowed deeper and it’s a(n unfortunate) reflection of our value system. I wrote:

Tech folks are primed to love optionality because in tech the outlier outcomes are so much better than the rest. The upper bound of possibility is so lucrative and fantastic (joining a company that goes public and mints you millions practically overnight, for example) that it’s so obviously worth it to continuously optimize around that.

Again, the mechanisms may have changed (it’s not going public but rather getting acquihired/HALO’d by an AI lab) but overall, still right on. Today we’re even more awash in opportunity and the possibilities feel even more boundless. If AI is really a paradigm shift, then by staying in one place you’re risking being left behind by superintelligence in the permanent underclass. Or so the thinking goes.

There are $100M signing bonuses out there for those job-hoppy enough to seize them! And as the upside has gone up, so too has the opportunity cost gone infinite.

The aspirational career path of the moment is fundamentally about independence and self reliance. Corporations/big brother aren’t going to help you, you have to help yourself and go get yours. If “no one is coming to save you,” then you have to keep doors open and preserve your options. And of course this idea is so central in the startup psyche that it naturally pervades the rest of your/our lives beyond work. It’s power law optimization for the everyday!

But it’s not without consequence. I wrote and still think:

Counterintuitively, being optionality-obsessed is just as fearful as it is optimistic. It reflects the fear of making the wrong choice just as much as hope for making the right one. What happens if I stay too long in the “wrong” job or date someone and it doesn’t work out or I miss out on that next shiny object that would have changed my life? I’d be ruined by opportunity cost! Optionality lets you preserve the chance that you’ll strike gold and minimize the risk of committing to the wrong thing but only by avoiding commitment at all.

Of course options aren’t free. You pay a premium for the right to choose later.¹ Sometimes that is well worth it: you should never rush through a one way door and there’s usually a lot of good work to do before committing. But often, “retaining optionality” is a thin excuse to avoid hard decisions (any decisions) because something better will come along.

This idea that there is always something better so you should never settle is a mind virus. It’s a deadly meme. You have to be present to accomplish, achieve, or enjoy things. You have be part of making something good/better rather than hoping someone else will do it for you. And it’s impossible to be present when you’re keeping an eye on the door. To truly lock in means to foreclose other possibilities. Otherwise you’re just cosplaying focus.

I don’t mean to be too moralizing or judgemental. I get the appeal and the feeling that you’re missing out. When I first wrote about optionality during the height of the Covid market mania, I felt like/was worried that I was missing out on all these other things. At the time I was considering going to work at a portfolio company and/or raising a small solo fund and/or and going truly bi-coastal; it seemed so easy and obvious. I could have it all, everywhere, right away. Against Optionality was an output of my trying to think through what that might cost me.

Since then quite a lot has changed for me. Four months after publishing that I quit the only full time job I had ever had. I got a dog. I got engaged.

But way more has stayed fundamentally the same. I’m still just a VC. I’m still living in Brooklyn. And in September I’ll be marrying the incredible woman I was dating in August 2021.

So do you need to stay with your boyfriend? Of course not. Do you need to have only one job for your whole life? No. Must you always make binding decisions quickly? Obviously not.

But there is huge value in sticking with things and letting gains compound over a long time. If you never commit to something (good or bad), you’ll have limited experience to recognize something really special when it does come along. Sometimes you have the burn the boats to see the costs of failure are pretty low and the upside from investing real time and effort are unimaginable.

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Tech for Abundance

New York is clearly at a crossroads and I see tremendous potential energy to harness for change. Next month I’m hosting an event with Abundance NY, Lux Capital, and Company Ventures in NYC. We’re bringing the startup and tech community together share ideas and hear from startup founders and leaders in government. We’ll be announcing the agenda and speakers as we get closer the event.

​New York City is in flux, politically and technologically. Old paradigms of liberal governance are being challenged by adherents of abundance as AI disrupts industries.

The City should be a great place to build a business AND should take full advantage of our entrepreneurial spirit to make government work better.

So What

Right now we’ve got two dinners scheduled for next month. In each, we’ll work on a single long range theme and work through its implications, extrapolations, and ripple effects.

• August: AI will keep getting better

• August: Attention is the new economic substrate

For the “Attention” dinner I’m super excited that Kylan Scanlon, author of In This Economy and one of my favorite creators, is coming to NY to co-host with me. She is one of my favorite thinkers and will make this really special. Sign up/apply to join the series here. Space will be limited.

We'll pull the thread and extrapolate out the ripples of the attention economy across work, markets, life.

Read on for my own AI extrapolations and I want to hear yours!

Slow Upload

Megan Lightcap, who runs the creator fund at Slow, is relaunching her newsletter with a four part series on how we underwrite media and creator entrepreneurs. It’s a great read for anyone who cares about the creator economy, consumer investing, and media.

I Wrote

• Startups don’t compete with one another nearly as much as they compete with inertia, default bias, entropy, and incumbents. So VC conflicts of interest basically don't exist/don't matter.

• I went to an AlleyCorp-hosted event to hear Zohran talk to the tech/startup/business community and spoke to Business Insider about it. My full quote to BI:

Zohran nailed it that government efficiency, outcomes, and effective service delivery have to be central to democratic politics. I was glad to see him being open to new ideas and working with people outside his base.

Over the last few months he’s done good a good job moderating on issues that matter to NY. Whether that’s because of an authentic commitment to pragmatism and listening to outside perspectives or if it’s just typical politicking to expand the base remains to be seen. If his evolution is sincere, it’s an encouraging sign about how he would govern.

I’m glad I went to the meeting. He’s probably going to be the mayor and whatever disagreements I have with him, much better to engage and have a voice than stand off to the side and pout.

1. That options trading is the preferred financial instrument of Gen Z is just too perfect/too literal an encapsulation of the wider cultural moment!