>600 subscribers

Don't Die of Heart Disease
During my "hiatus" I've been doing research in a variety of different areas that interest me. After a personal experience with basal c...
The Deal
Founders have little to no diversification. They are all in on one idea, company, and mission. It's an insanely high-risk, high-reward endeavor. As founders become increasingly wary of this level of risk concentration, they begin to think about ways to mitigate it. One idea I've heard repeatedly is the notion that a group of founders can self-assemble and contribute a percentage of their equity in their company to a shared pool. That way, if they fail and one of the other founders in the grou...

Sequoia Wants It Hard
I have seen a lot of young first-time founders play it fast and loose in their fundraising processes the past several years. It’s been frothy times, so I think it brings out a lot of strange behavior. It got me thinking of when I was a young founder and the things I’d do, particularly one specific story that I tell people when I get asked “what not to do” when fundraising. Back in 2010 Steve and I launched GroupMe to much fanfare. It got a lot of attention out the gate because we built it at ...

Don't Die of Heart Disease
During my "hiatus" I've been doing research in a variety of different areas that interest me. After a personal experience with basal c...
The Deal
Founders have little to no diversification. They are all in on one idea, company, and mission. It's an insanely high-risk, high-reward endeavor. As founders become increasingly wary of this level of risk concentration, they begin to think about ways to mitigate it. One idea I've heard repeatedly is the notion that a group of founders can self-assemble and contribute a percentage of their equity in their company to a shared pool. That way, if they fail and one of the other founders in the grou...

Sequoia Wants It Hard
I have seen a lot of young first-time founders play it fast and loose in their fundraising processes the past several years. It’s been frothy times, so I think it brings out a lot of strange behavior. It got me thinking of when I was a young founder and the things I’d do, particularly one specific story that I tell people when I get asked “what not to do” when fundraising. Back in 2010 Steve and I launched GroupMe to much fanfare. It got a lot of attention out the gate because we built it at ...
Share Dialog
Share Dialog
Last year I publicly shared my goals for 2022. I like having a public record of this. Diving in, here's how I stacked up against my goals from last year. I am really happy with my achievement rate. If these were OKRs I'd consider it a successful year.

I like a tops-down approach for personal goal setting, beginning with answering the question: "If I were 80 years old, what would I regret / not regret having done over the course of my life?" From there I like to list out my ten-year goals at a very high-level, and then dig into annual goals.
This year I have updated my regret minimization framework:
By the time I'm 80 years old, I won't regret having spent an abundance of quality time with my family, having read and retained the learnings of terrific books and being knowledgeable about the world (both the way things work and why they work that way), knowing myself and what makes me truly happy, having traveled and explored the world to my heart’s liking, spending time in nature, feeling like I’ve made people’s lives better and contributed to civilizational progress through my professional endeavors, and investing in the relationships that matter most with friends and family.
I've also updated my long-term (10 year time horizon) goals. I really like how these are simple and more about the way I will feel in ten years instead of objective numerical measures of success.

And finally, I modified my goals for 2023. These aren't a major departure from 2022, they're really more of a continuation of what has been. I think it's good that these are iterative and evolutionary - it makes them feel doable and realistic and hopefully will enable the progress to compound over a ten year period.

Here's to a fun and meaningful 2023!
Last year I publicly shared my goals for 2022. I like having a public record of this. Diving in, here's how I stacked up against my goals from last year. I am really happy with my achievement rate. If these were OKRs I'd consider it a successful year.

I like a tops-down approach for personal goal setting, beginning with answering the question: "If I were 80 years old, what would I regret / not regret having done over the course of my life?" From there I like to list out my ten-year goals at a very high-level, and then dig into annual goals.
This year I have updated my regret minimization framework:
By the time I'm 80 years old, I won't regret having spent an abundance of quality time with my family, having read and retained the learnings of terrific books and being knowledgeable about the world (both the way things work and why they work that way), knowing myself and what makes me truly happy, having traveled and explored the world to my heart’s liking, spending time in nature, feeling like I’ve made people’s lives better and contributed to civilizational progress through my professional endeavors, and investing in the relationships that matter most with friends and family.
I've also updated my long-term (10 year time horizon) goals. I really like how these are simple and more about the way I will feel in ten years instead of objective numerical measures of success.

And finally, I modified my goals for 2023. These aren't a major departure from 2022, they're really more of a continuation of what has been. I think it's good that these are iterative and evolutionary - it makes them feel doable and realistic and hopefully will enable the progress to compound over a ten year period.

Here's to a fun and meaningful 2023!
No comments yet