10 Things that changed how I thought about building things that matter

Since moving to Silicon Valley four years ago, I’ve learned far more from actors in tech and entrepreneurship than any book or course. Here are 10 things that have changed how I think about building things that matter.

Hope and Opportunity

White Space is Everywhere, by John Lilly

I vehemently agree with both parts of this talk: right now is an exceptional time to be building things, and we should do this with the best people possible — people of integrity, intelligence, and energy.

The fun part is finding those great people to build with. I look for energy. What convinced me to join Greylock was the energizing, rapid-fire conversations I had during my interviews. The Thiel Foundation further structures this as Mentors help select new Fellows, asking us “Did you feel more or less energized after meeting this candidate?” I’ve always loved that approach, and now explicitly sense for it when finding people to work with.

Why are startups able to outmaneuver large competitors?, by Michael Wolfe

Michael explains how a startup called Lookout was able to beat large security companies like Symantec and McAfee in a new market. But this is really a case study in the dynamics behind The Innovator’s Dilemma, and how new players can beat incumbents in any industry. Seeing this happen play out time and again in Silicon Valley has caused me to be even more dismissive than Michael about competing with the big guys.


The Only Thing that Matters, by Marc Andreessen

This post is where Marc describes the now-universal concept of product-market fit. And it’s where my understanding of how startups work shifted from clean, linear progression to distinct phases of searching for product-market-fit, and scaling it from there.

And you can always feel product/market fit when it’s happening.” he writes.

He’s right. It’s what I felt in my first few weeks at AngelList, as the industry caught on to what we were building and flooded us with interest. I remember asking Naval at that time whether in all his successes he’d ever felt such a strong market pull. ‘Never,’ he replied.

Hidden in the tactical guidance about product-market fit is a beautiful idea that all we’re really doing is trying to create things that matter for people, and that when it works, we know.

Get One Thing Right, by Andy Dunn

Andy tells the story of creating Bonobo pants for a small but excited group of initial customers. But what he’s really talking about is focusing on getting one thing right. Just one thing. I love very different takes on this by Michael Wolfe and Jane ni Dhulchaointigh as well.

Consider that in the earliest days, our tech stack at AngelList was Wordpress, Wufoo, and Gmail. Using only that, some nugget of value was found, and then talented folks like Graham, Josh, and Milos set to work getting that right.

For most of us, this search is terrifying. We don’t want to admit when our offerings miss the mark (as they so often do). We want what we’re building to be valuable so we fill it with features, and uses, and buzzwords. But all that does is obscure the search for that one thing that people love.

Shaping Our Surroundings

Maker’s Schedule, Manager’s Schedule, by Paul Graham

Our effectiveness is influenced by the contexts we create for ourselves. This PG essay crystallizes that for one key element: time.

I first read this essay to better understand how to avoid annoying others on our team at Greylock. I wanted to give them space when they were deep into a problem. But it also helped me understand how to organize my own work, and led me to plan for larger chunks of deep dive work in the mornings, and connections and meetings with others in the afternoons. It’s a tactic that I’ve used for years.

Related: Flow, Joel Spolsky.

Invest in Lines, not Dots, by Mark Suster

Mark makes a case for building a relationship (‘a line’) with investors early from multiple connection points (‘dots’). Implicit in that is that he gets to see the slope of that line too: how fast people progress between those dots.

One surprising place this has popped up for me is in working with accelerators. Given the sheer number of them, it’s hard to determine at first which are great. It’s only in watching for the change in quality between cohorts that I can really tell. I found this to be the case with AngelPad, as their companies got stronger and stronger early on. To this day, they’re one of a few programs I’m happy to support, whenever they ask.

So, much more than just how to approach to building investor relationships, Mark’s post captured a general relationship philosophy that I believe, and gave good shorthand to talk about it.

Tactical Advice

Owning Your Recruiting, by Daniel Portillo

Whether sitting in on pitches from the best entrepreneurs, or watching my colleagues in action, working at Greylock has shown me how critical talent is to any company, and how it needs to be baked in early to culture and processes. Thankfully, Greylock Talent Partner Dan Portillo laid out his techniques for anyone to read. I’ve used his guidance myself, and recommended it more times than I can count.

Create a Market for Your Shares, by Babak Nivi and Naval Ravikant

Long before AngelList was a thing, Nivi and Naval created some of the best pro-founder education out there. This post by Nivi and Naval explains why fundraising works best when compressed into as short a time period as possible, even when it seems too intense to manage. It’s still a common piece of advice I give to fundraising founders.

The post captures some of their most important thoughts but is far from the only good one — not only should founders school themselves for a full day in their archives, but probably anyone with startup equity as well — employees, investors, and advisors too.

Multiple Posts, by Elad Gil

All of Elad’s pieces are worth reading, so it’s hard to pick just one. He’s one of the clearest high-signal writers on building companies that I’ve read. I’d start with his posts on hiring for culture fit, hiring for the ability to get shit done, raising your perspective 10X, avoiding bad advice, or what the main types of lock-in look like.

Keeping Perspective

Racism and Meritocracy, by Eric Ries

Eric has given founders an entire playbook on how to build young companies. And yet I think this piece on bias is his most important contribution. In 2012 we were talking about racism. In 2014, it’s gender. But bias is bias, and systematic discrimination is still discrimination.

Eric’s post helped crystallize for me what was already rumbling around in my head. We do work in a meritocracy, to a large degree. But not completely. And when the path of a founder, investor, or developer depends on thousands of actions of others, those small biases compound into deep unfairness.

I remembered this at Greylock while we looked for a new Analyst. We asked a few knowledgeable friends to review our job posting for unintentional bias or messaging. As they reviewed it, I was shocked at the hidden cues there were for male applicants (aggressive wording, or overuse of terms like ‘hacking’), and how that might have discouraged female applicants from applying. We made some adjustments and it seemed to help, as we ended up with a good range of applicants deep into the process.

(Related: How Etsy grew their number of female engineers by nearly 500% in one year)

What does the First Day of a 5+ Year Prison Sentence Feel Like?, by Kenyatta Leal

Kenyatta and his colleagues’ answers to questions about life and prison first introduced me to The Last Mile, a program that runs an accelerator inside several maximum security prisons. I’ve worked with them since then, and gotten to know some incredible people. I was shocked at their first demo day, when their pitches were communicated more convincingly than any accelerator I’ve seen. This context strips the daily bullshit and reveals what matters: people trying to better themselves, their lives, and their world in the purest way possible. It’s been a refreshing lesson for me, amidst the grind of daily life.

Check out Kenyatta’s post on what being part of the program meant for him.

So there’s 10+ resources to get started. And a few others also consistently deliver great insights — check out Andy Rachleff, Chris Dixon, Fred Wilson, and Jason Freedman. What have you read that changed your mind about how to build things that matter? Let me know in the comments.

I’ll be publishing a few more pieces shortly. Follow to be notified. Thanks for reading this far.

(Thanks to Eliza Schreiber and Ben Mathes for reading drafts of this and providing valuable feedback.)