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Tim Hsia
Partner at Context VC and Co-Founder of The Milvet
Tim Hsia is a prominent entrepreneur and investor, serving as the founder and Managing Partner of Context Ventures, a venture capital firm that focuses on investing in consumer startups and military veteran founders. He has a diverse background that includes military service, entrepreneurship, and venture capital.
Education and Military Background
Tim Hsia graduated as a distinguished honor graduate from the United States Military Academy at West Point, where he double majored in Military History and Environmental Engineering. He was commissioned as an infantry officer in the U.S. Army and deployed twice to Iraq. After transitioning from active duty in 2010, he pursued further education at Stanford University, earning both a JD and an MBA by 2014.1
Career in Entrepreneurship and Venture Capital
Hsia is not only the founder of Context Ventures but also has a history of founding and leading other companies. He previously established Media Mobilize, an online advertising network and marketing agency. His venture capital investments include notable companies such as Workflow (acquired by Apple), Morning Brew (acquired by Business Insider), and Thredup (which went public) among others.1
Contributions and Interests
In addition to his business ventures, Tim Hsia is actively involved in nonprofit work. He co-founded Service to School, which helps transitioning servicemembers and veterans gain admission to top colleges and graduate schools. He also serves on the board of the Marine’s Memorial Association in San Francisco. Hsia is a published writer, contributing to various publications including The Los Angeles Times and The New York Times.1
Hsia's interests include running, learning about history, and spending time with his family, reflecting a well-rounded personal and professional life.1
Highlights
Executive Summary: America’s Associations & The Military Veteran Club
1/ Alexis de Tocqueville, one of the first and keenest observers of American democracy in the 1830s, noted that unlike Europe, Americans like to associate and join clubs. I find this concept powerful and personally relatable because the next two weeks embody the power of associations:
⚡ Last night in Denver, our teams at Context VC, The Military Veteran, VetraFi held a fun military veteran get together (including some pictures here)
🎖 Today I'm in Washington DC attending a Business Executives for National Security (BENS) dinner. It'll be great to listen and learn from the Palantir Technologies CEO and Gina Raimondo, of the United States Department of Commerce
🧠 Tomorrow and Friday I’ll be in Manhattan attending the Council on Foreign Relations National Conference
🔥 Next week, we are hosting another military veteran get together in Chicago
🎓 Next week is also the Service to School Summit in Chicago!
2/ I won’t try to paraphrase Tocqueville, so here are some good quotes of his on the uniquely American predilection to associate:
“In democratic peoples, associations must take the place of the powerful particular persons whom equality of conditions has made disappear.
As soon as several of the inhabitants of the United States have conceived a sentiment or an idea that they want to produce in the world, they seek each other out; and when they have found each other, they unite. From then on, they are no longer isolated men, but a power one sees from afar, whose actions serve as an example; a power that speaks, and to which one listens.
…
There is nothing, according to me, that deserves more to attract our regard than the intellectual and moral associations of America. We easily perceive the political and industrial associations of the Americans, but the others escape us; and if we discover them, we understand them badly because we have almost never seen anything analogous. One ought however to recognize that they are as necessary as the first to the American people, and perhaps more so.”
- Alexis de Tocqueville in Democracy in America
3/ I spend a lot of my time associating with military veterans. At Stanford Law School, a professor told me that its university could be likened to a powerful union group. That might be true, but I believe the most powerful association is the military veteran group. I believe it’s perhaps the most exclusive and yet also inclusive group.
4/ Yesterday evening was a really fun get-together of military veterans in Denver. Thank you Charlie Kelly of Stifel Bank Stiefel Bank for sponsoring this event!
Thank you Eric Shu & Aaron Stachel for helping promote this event and sharing more about your venture firms!
5/ Thank you France Q. Hoang, Shawn Olds, & boodleAI team for sharing, how you all are building generative AI tools for teams.
6/ It was great meeting and catching up with a ton of fantastic and positive military veterans in Denver 🙏!
Executive Summary: Investing in Military Veteran-Led Founders & Startups
1/ At Context VC, we invest in three distinct categories at the pre-seed/seed stage:
🎖 Military Veteran-Led Founders & Startups 💸 Fintech Startups 💡 Consumer Startups
We are both serious and joking when we say we want to be in the friends, family, and fools round. We just want to be treated like friends and family and not make foolish investment decisions.
2/ To date, the vast majority of our investments have been into military veteran-led founders & startups. These military veteran founders have built companies across a range of industries: Fintech, Proptech, B2B Saas, Consumer, Defense Tech, AI, etc…
These founders range from all backgrounds: enlisted, officer, US Navy, United States Marine Corps, US Army, ROTC, Service Academy, West Coast, East Coast, Texas, etc…
Here are just a few of the startups we have invested in: ⚡ Aaron Kline at Boom & Bucket ⚡ Luke Hutchison at Perfect Venue ⚡ Kris Sandor at Readyly ⚡ Timothy Herman at UpEquity ⚡ Sonny Tai at Actuate ⚡ Chris H. at Azibo ⚡ Marco Nelson at RentCheck ⚡ Bradley Genser at Farther ⚡ Garrett Smith & Andrew Dixon at Reveal Technology ⚡ France Q. Hoang & Shawn Olds at boodleAI ⚡ Brendan Aronson & The Military Veteran ⚡ Lucas Babbitt at Atomic Insights ⚡ The team at Wove ⚡ And soon we'll be able to share another company we are incubating with K. Holden Lindblom.
3/ We strongly believe that military veterans can build massive companies. History supports this thesis given the success of military veteran founders such as:
⚡ Fred Smith of FedEx ⚡ Bob Parsons of GoDaddy ⚡ Phil Knight of Nike ⚡ Vinny Viola of Virtu Financial ⚡ Kathy Hildreth of M1 Support Services ⚡ Stephen Schwarzman of Blackstone, and many others.
➡ We’ve written a book about these founders See comments below.
4/ Recent history suggests that the Post 9/11 era of military veterans are building fantastic companies
⚡ Blake Hall of ID.me ⚡ Taylor Justice & Dan Brillman of Unite Us ⚡ Roxanne Petraeus of Ethena ⚡ Socrates Rosenfeld of Jane Technologies ⚡ Henry Ward of Carta
5/ Along with a portfolio company, The Military Veteran, we host a number of events for military veterans broadly and roughly average an event a month.
We have a number of upcoming events we’ll be hosting or co-hosting across the United States, from New York to Denver to Seattle to Chicago. We also have our annual Military Veteran Startup Conference we host.
➡ To learn more about these events, sign up for our email newsletter, link in the comments below.
6/ In 2022, we published a study on Military Veteran Startup Trends.
➡ Link in comments below.
7/ In 2023, we published the top 150 Military Veteran Led Startups.
➡ Yes, you are starting to see a pattern here, link in comments below.
8/ If you are a military veteran startup founder with grand ambitions to build a category defining and consequential startup/company, then please message the Context Ventures team and myself!
