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Had the dotcom bubble not burst I’d likely be an attorney. I’d accepted an offer at a law firm in San Francisco to work in their Securities practice, largely taking companies public or doing M&A.

In March of 2000, the firm called and said: “Good news bad news. Good news: you still have a job [unlike a lot of my law school classmates]. Bad news: we don’t need any more Securities lawyers, but we have lots of room in our Bankruptcy practice.”

Being a Bankruptcy lawyer didn’t sound like fun. A law professor’s brother was starting a B2B startup. He offered me a job. The startup was a colossal failure, but I was hooked on the idea of a group of people starting something from nothing.

Next ~8 years were painful with lots of ideas that went no where, but it all worked out. So, in the end, always remember that but for the dotcom bubble bursting, I’d be keeping track of my time in six minute increments.




Always remember that without the dotcom bubble, eastdakota would be counting in 6 minute increments :P

Sincerely, can you say more about the 8 years of pain? I’m curious how you navigated that, especially with/without relationships, family obligations, “runway” restrictions, etc

Edit: looking at the profile, eastdakota is CEO and cofounder of CloudFlare. There are probably interviews and Wikipedia pages that address my questions.


Those 8 years were painful. To make money, I worked as a bartender, an LSAT test prep instructor, as an adjunct law professor at a law school that was so bad it doesn’t exist anymore. I remember 4am at the bar in Chicago where I worked, cleaning up some patron’s puke off the floor, and thinking: I need to figure something else out.

All the time I was trying to find an idea for a startup. I still had the lawyer bit flipped on so lots of things I tried had a legal/regulatory bent. That was definitely a blind spot that held me back for a while.

The fun YC-related story on the founding of Cloudflare is that, before YC, Paul Graham used to host a conference called the “MIT Anti-Spam Conference.” He invited me the second year of the conference (2003, I think) to give a talk on how to write effective anti-spam laws. The very technical crowd was polite to the lawyer. I met a ton of interesting people, many of whom played outsized roles in machine learning over the next few years, including John Graham-Cumming, now Cloudflare’s CTO. Paul invited me back the following year saying I should do something similar.

I was pretty sure the audience wouldn’t tolerate the lawyer giving another talk about regulation, so I went to a young engineer on the team of the (bad) startup I was working on and suggested we build a system to track how spammers scrape your email addresses. He agreed to build the backend if I built the front end (which I largely stole from the hot startup of the time: LinkedIn). That turned into Project Honey Pot, which I gave a talk on at Paul’s conference. Project Honey Pot gave the initial seed of an idea that turned into Cloudflare. And the young engineer was Lee Holloway who cofounded Cloudflare with me and Michelle Zatlyn.

Lesson to me has always been even in times where you don’t feel like you’re making forward progress in your life and career, find ways to stay involved with interesting people and projects and chances are they’ll pay dividends in ways you don’t expect later in life.

I clearly remember walking back to Paul’s house in Cambridge after the 2004 conference where I’d presented Project Honey Pot. I believe he and Jessica had relatively recently started dating. They were talking about startups and how people didn’t understand how they worked. Paul suggested they should teach a class at MIT. And that, of course, is what later turned into YC.

There were other dramatic events that evening in Cambridge that I think sharpened all our minds and made us appreciate there’s no time like the present, but I’ll leave that story for another day.


I met a ton of interesting people, many of whom played outsized roles in machine learning over the next few years, including John Graham-Cumming, now Cloudflare’s CTO.

And the other way around. I met eastdakota which would later lead to me being at Cloudflare. Turns out networking (human and computer) is important.


And then, 20 years later, I meet a kid on the local playground who claims to be the son of one of the Cloudflare co-founders or CTO. I was thinking, wait, isn't JGC in Britain, not Boise? Even though the kid was visibly disappointed that I'm bearish on nVidia and LLMs, he strained my understanding of how puts work in stock trading. So that amusing conversation, sporadically interrupted by loading and unloading my toddler from the swingset, encouraged me to get more familiar with the broader investment market, beyond the simple kid invest products I've been working on the past four years. So thanks for that proverbial push on the swings, Cloudflare kid!


There's not a high chance that this piece of history will be lost "forever", it will just remain as a HN comment.

I wonder what would be the best way to harvest these and add them to, say, a wikipedia page. I'm pretty sure it's something that you could decently do with an LLM.


Which bar did you work at in Chicago? Was it in Hyde Park?


This is awesome. Thank you for sharing this.


Damn, what a turn of opportunities from just saying yes and showing up (and obviously a ton of hardwork and sacrifices). Thanks for sharing!

I can't resist ...

> There were other dramatic events that evening in Cambridge that I think sharpened all our minds and made us appreciate there’s no time like the present, but I’ll leave that story for another day.

> ... appreciate there’s no time like the present ...

The present is now! Some of us are dying to hear the story.


I’ve told it elsewhere. Some Googling around may turn it up.


I love how humble his origin story was, and how he didn't need to drop in where he is/who he is as part of it.

Amazing who you /meet/ here.


Definitely. I think this is true of the internet in general, we have an amazing ability to communicate with almost anyone, even busy experts in niche fields, if we just make/ask something that interests them. I don't think I appreciate that enough.


To be fair, if you had gone down bankruptcy you could have made a killing doing distressed during one of the most lucrative periods.


I have plenty of friends who went down that path. They’ve done very well as lawyers. But suffice it to say that if offered they’d readily trade places.


Maybe, although the people just getting into the field probably aren’t making the fortunes and there wouldn’t be the satisfaction of building something real.


Wow! You ended up building a not-so-small piece of today's internet. Congrats.

Edit: one question I have for you: besides the "sliding door" moment of dropping the lawyer career and choosing another one, what convinced you to abandon a law career entirely? Most other lawyers would have sticked there.




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