I’m a Partner at Contrary. Backed by the founders of Tesla, Reddit, and many more iconic companies, we identify top talent and invest in companies they start or join.

You can find me on TwitterLinkedInGitHub, and email.

I sometimes write or host discussions about things that interest me. Broadly speaking, that includes startups, investing, software, psychology, evolutionary biology, politics, and these questions.

My free time has been spent discovering new music, traveling to 49 states, and reading.

Check out my series of conversations with the founders of companies like Airbnb, OkCupid, and Vimeo.


Below are posts I’ve written for my blog or major online publications. If you’re hit with a paywall, contact me and I can send a copy.

First Principles Interviewing how to hire for insight rather than experience by asking the right questions

Opportunities (and challenges) in church tech part two of the church tech TC series

Jesus, SaaS, and Digital Tithing a TechCrunch article about the church tech market

Voodoo Games: Three Narrative Violations my TechCrunch piece about how Voodoo upends recent startup trends

Venture Investing in Eldertech my TechCrunch piece about trends and opportunities in eldertech

Creating Product Stickiness how businesses can become more defensible… out of thin air

Reinventing the Wheel why anti-tech pessimists think the way they do, and how to reverse-engineer that

2019 University Report a ranking and analysis of the top entrepreneurial ecosystems in the US

Analyzing Venture Opportunities Part 2: Thinking About People a list of things to consider when evaluating or pitching a team

Why Ownership Graphs Matter hidden complexity in politics and an interesting idea

Social Spaces on the Internet a handful of trends that will help shape social spaces online

The Paradox of Compound Interest saving and spending when opportunity cost compounds too

Getting Good at Startups general principles on becoming a good founder or investor as a student

3 Questions on Tech Companies a few brief thoughts on moats, successful teams, and evaluating people

Request for Startups a list of companies I’d start in another life

Competition Matters Less in Software what makes tech companies unique?

Senior: My Time at Umbrella some learnings from working at Umbrella

When Insiders Were Outsiders stories of people who hustled and struggled their way to where they are now

Notes on The Elephant in the Brain some context and notes on one of my favorite reads

Concise Ideas are One-Dimensional should we think about nuanced ideas where concision rules?

Worldview as Competitive Advantage do the typical value-add dimensions really matter for most investors?

Degrees of Freedom don’t make your startup’s gameplan needlessly complex

Buying IBM examples of upside/downside asymmetry

Go-To Essays and Books what I like to re-read and recommend

Getting Positive Feedback tips for founders who get really positive feedback in early validation efforts

Psychology in Product and Sales a list of concepts in social psychology with examples

Decision Making and Mental Models a toolkit for thinking more clearly and making better decisions

What Do You Optimize For? balancing serendipity and focus for optimal results

Simpson’s Paradox and Thinking Rationally in Venture Capital how empiricism and pattern recognition can go wrong

Existential Risk and Effective Altruism a primer on a fascinating concept in ethical philosophy

Analyzing Venture Opportunities Part 1: The Product and Market a list of things founders should always touch on when explaining their startup

The Flawed Economics of Robinhood: Why Users Are Better Off Without It the reasons why Robinhood’s business model is misaligned with users’ needs

A Clever Malware Tactic and Why There’s Nothing You Can Do About It how I came across an innovative scam

My App Marketing Story: 0 to 100k Downloads the strategy and tactics I used to successfully publish an Android app


V.F.S. Volume 2 – my second mix. This time, it’s more sophisticated with a workout/party vibe.

V.F.S. Volume 1 – my first ever mixtape. Inspired by ODESZA’s NO.SLEEP mixes.

Twitter-Tools – a Twitter API wrapper that makes basic analytics and data munging easier

Brick Breaker Free – in high school I taught myself Android and wrote a clone of the classic game Breakout. It was downloaded over 100,000 times before it was finally retired

Techwurk.org – I cofounded Techwurk in high school to connect charities with students interested in web design. Raised a small amount of money from investors.

Perspective – a Chrome extension that parses a web page looking for textual representations of dollar amounts. It then manipulates the DOM to replace each dollar value with a phrase representing potential charitable impact. For example, a page saying “buy now for $4.99!” would be changed to something like “buy now for enough money to donate an anti-malarial mosquito net!” This small project was inspired by FlipWord.

Neural Network Text Generator – a recurrent neural network architecture to generate coherent English based on a seed phrase (not published anywhere — ask me for source code).

Interest Matcher – a location-based web app that facilitates the discovery of events. Chill shared a lot of functionality with Yik Yak, but it is not anonymous. I built it with and handful of friends in Fall 2015. Now it’s offline and unmaintained — ask me for source code if interested.