Mike Steadman is not your typical VC. A former Marine infantry officer, three-time national boxing champion, and self-described "underdog and misfit," Mike came up through bootstrapping businesses before landing at Context VC as a venture partner -- a path that gives him a sharp eye for what separates founders who get funded from those who don't. His advice throughout this episode is grounded, tactical, and refreshingly honest.
What makes this episode worth your time is how Mike frames fundraising as a second product that founders have to build and sell in parallel with their actual business -- and most founders are wildly underprepared for it. He walks through everything from how to build a hyper-targeted VC list using your "unfair advantages," to why your LinkedIn profile matters more than your pitch deck at the pre-seed stage, to how to behave in a GP meeting when a term sheet offer might land in real time. He also doesn't shy away from the harder truths: that you need to be talking to far more investors than you think, that warm reputation checks are a real part of diligence, and that closing the round is just the start of the hard work.
