Mike Steadman

Venture Partner, Context VC
Mike Steadman, a former Marine Corps infantry officer, three-time national boxing champion and venture partner, helps veteran and overlooked founders define and own market categories via his Category Whisperer approach.
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Geos their fund invests in
USA
Mike Steadman
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Sectors their fund invests in
Under-represented founders
Fintech
Defense
Consumer
AI
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Leads?
No
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About Mike Steadman

Mike Steadman is a former Marine Corps infantry officer and three-time national boxing champion who works as a venture partner at Context VC, where he specializes in helping founders define and own new market categories rather than just building features. He focuses specifically on military veteran founders and other overlooked entrepreneurs through his Category Whisperer approach, combining his combat and boxing background with category design expertise to pressure-test startup narratives and positioning.

Mike Steadman's Interests

What they've been talking about across their social media accounts
  • Bias toward relentless execution and real world building over theoretical learning. Startups pitching should highlight concrete actions and traction because classroom style presentations and endless planning are seen as inferior to simply getting to work and building things.
  • Deep appreciation for extreme personal accountability and an intense work ethic. Success is framed as doing the difficult things others avoid, waking up before dawn, and dropping any past grievances to focus solely on what can be controlled today. References to endurance athlete David Goggins and author Malcolm Gladwell show a major respect for gritty, disciplined routines.
  • Strong advocacy for military veterans and founders of color. Hosts a podcast specifically geared toward discussing how to raise capital for underrepresented veteran entrepreneurs, drawing heavily on a personal background linked to the Naval Academy and military service. This is a massive warm introduction angle for founders fitting that profile or building in that space.
  • Prioritizes genuine character and intrinsic motivation rather than just chasing a massive financial exit. Expresses distaste for companies that treat diversity or social impact as a superficial public relations move, looking instead for founders who truly love the daily grind of entrepreneurship and define their success by more than just dollars.
  • Actively cultivating a daily writing habit and working on long form fiction. Currently developing a novel centered on a minority military officer navigating complex societal issues, and actively asking the community for accountability to write every single day. Asking about the progress of this book would be a highly effective and personalized icebreaker.

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."
Mike Steadman
Venture Partner, 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."
Mike Steadman
Venture Partner, 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."
Mike Steadman
Venture Partner, 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."
Mike Steadman
Venture Partner, 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."
Mike Steadman
Venture Partner, Context VC

About their Fund

Sectors
Under-represented founders, Fintech, Defense, Consumer, AI
Rounds
Pre-Seed - Seed
Avg Check Size

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.

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