The list below consists of representative personal investments.

Direct (Seed)
Protocol Labs - Protocol Labs is an open-source research, development, and deployment laboratory. Its projects include IPFS, Filecoin, libp2p, and many more.
On Deck - On Deck’s mission is to expand the global startup economy. It helps people start and scale companies, get impactful jobs, and invest in their careers.
AltoIRA - With a self-directed IRA from Alto, you can invest your retirement dollars in alternative assets.
Equi - Equi uses technology to unlock elite investing. Its vision is for a world where anyone can have a portfolio to rival the most sophisticated family offices.
Banana - Banana is building machine learning infrastructure for the digital economy.
Onward - Onward helps co-parents track and manage shared expenses for their children.
Allocate - Allocate provides a new way to access top-tier venture capital.
AbstractOps - AbstractOps is building the operating system for scaling companies.
Grasshopper Kids - Grasshopper helps kids discover their passions through hands-on learning experiences led by teachers at your house, on your schedule.
Passthrough - Passthrough’s mission is to organize and structure investor identity information and make that information interoperable.
Flow Club - Flow Club lets users host remote coworking sessions designed to help people get into a productive flow state.
Operator - Operator's platform makes it easy to collect data from any business and get customizable metrics on their performance.

Haystack - Haystack is an institutional venture capital firm focused on early-stage investments.
Ubiquity Ventures - Ubiquity Ventures provides seed capital for "software beyond the screen" startups.
Runway Fund & Community Fund - Investing in the best companies that come out of On Deck fellowships.
Gilgamesh Fintech Ventures - Gilgamesh is an early stage venture capital fund focused on fintech in the Americas.
The Operator Fund - The Operator Fund is an early stage fund led by the founders of AbstractOps.
Allocate Alpha Fund - Allocate’s Alpha Fund provides investors with unique exposure to a portfolio of high performing, access-constrained venture funds.
Allocate Premier Access Fund - Allocate Premier Access provides investors with exposure to a diversified pool of top venture capital funds across stages and sectors.
MKT1 Capital - MKT1 Capital is founded by marketing leaders and invests in Seed & Series A SaaS startups who want help building their marketing function.

Bitcoin, first in March 2013
Ethereum, first in the presale August 2014
Various other projects since then