Context VC

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Early-stage investor focused on military veteran founders, leveraging veteran-operator leadership, conferences, events, research and an integrated content/media stack to deliver outsized brand and distribution advantages.
Stages they invest in
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Can They Lead?
No
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Location
San Francisco
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Geographies They Invest in
USA
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Context VC
Stages
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Sectors
Under-represented founders
Fintech
Defense
Consumer
AI
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Avg Check
N/A
Leads?
No
N/A
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Industries
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What Makes them Unique

Context VC is a community-driven early-stage fund that builds the entire military veteran startup ecosystem through conferences, events, research reports, and online communities, positioning itself as the primary hub for veteran founders rather than just another investor. The fund combines unusual veteran-operator DNA at the leadership level with an integrated content and media stack that gives portfolio companies outsized brand and distribution advantages relative to the fund's size.

Video Interview

On treating fundraising like the main mission it actually is

"If you need VC to build the product and that becomes the main effort, like the main friction point, it's like you can't even do your thing if you can't raise the capital -- then you need to treat that and prioritize it like it deserves."

"Iron" Mike Steadman | Context VC

On being ready to negotiate the moment you're in the room

"If your number one goal is to raise venture capital and you get a GP in front of you, the person that can make the investment decision, and he's on the call with you, that is the most important meeting in the world. Whatever you got after that, cancel it. The other thing is be prepared to potentially receive an offer on that call... be prepared to do live negotiation right then, not I'm gonna send an email... because all that stuff saws momentum."

"Iron" Mike Steadman | Context VC

On the volume of outreach founders dramatically underestimate

"One of our portfolio companies that just closed at seed -- they were like, man, we talked to 150, 200 VCs, they'll tell you, and they track it on spreadsheets with notes. Just understand at a tactical level what it takes to actually make it happen. Get a spreadsheet, fill it in with 200 names, notes, follow-up dates, and freaking work it."

"Iron" Mike Steadman | Context VC

On what VCs are really evaluating before they even open your pitch deck

"Who is this person? What is the market they're going after? Why are they the ones to go after this market? We ain't even got to the pitch deck yet... your LinkedIn profile is like a landing page these days because it tells a story."

"Iron" Mike Steadman | Context VC

On why early-stage founders keep skipping the most important step

"Founders think they can skip the grunt work. You don't just get to 100 customers. Every great company was built off of one customer at a time. Eventually you're able to scale it and get lots of them, but when you're going zero to one, you need to manually onboard your customers -- and people just think they don't have to do that."

"Iron" Mike Steadman | Context VC

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