Fun Raising

Emily Lindberg brings a genuinely rare perspective to the VC world -- a PhD in biomechanics from UC Berkeley who transitioned into venture through Nucleate, a student-run VC focused on bio companies. That scientific background shapes everything about how Undeterred evaluates deals, and Emily is refreshingly candid about what that means in practice. She emphasizes that even when a fund loves your technology, it has to fit the financial structure of the fund and its return requirements -- a reality many first-time founders overlook entirely.

On the question of what gets a founder into the room, Emily reinforces something that often gets lost: cold outreach can genuinely work, but only if it's targeted and concise. Undeterred reviews everything, but founders need to respect how little time is actually spent on each deck. The clarity of your story matters more than polish or design -- and interestingly, Emily notes that a scrappy-looking deck can sometimes work in a founder's favor if it means they've been overlooked by others.

Where Emily really shines is in her advice around the later stages of a raise. She pushes founders hard on the idea that choosing an investor is a decade-long partnership, not just a transaction. Optimizing for valuation over fit is one of the most common and costly mistakes she sees. And once the round closes, she flags a pattern she sees repeatedly: founders going heads-down on tech and losing touch with customers -- the very people whose urgency and engagement will determine whether the company survives.

Leo brings a rare combination to the table: technical depth as a mechanical engineer with a PhD from MIT, operator experience as a former founder, and the analytical rigor of a McKinsey diligence background. That blend makes his fundraising advice unusually grounded. Where many investors speak in generalities, Leo is specific. He walks founders through how to build their investor CRM, explaining why identifying who leads versus who follows is the most important filter. He also breaks down what he actually looks at first in a pitch deck, including the ask slide, the why now, unit economics, and team, giving founders a clear hierarchy to design around rather than guessing.

One of the more tactical and under-appreciated pieces of advice Leo shares is around calendar density. He argues that talking to too few investors is itself a strategic mistake, not just a numbers game. Without enough conversations happening simultaneously, founders lose negotiating leverage, struggle to build syndicate followers, and can't generate the quiet momentum that nudges VCs to move faster. He also introduces a clever tip around using an FAQ inside a Docsend data room to gauge which VCs are actually doing their homework, a small but revealing signal founders can use to prioritize their time.

Leo closes with a sharp framework for the three phases of fundraising: getting the first meeting, moving VCs through diligence, and landing the first term sheet. He is direct that the first term sheet is the domino that makes everything else fall, and that the art of getting it is about subtly conveying momentum, such as mentioning upcoming site visits from other investors, without overselling. For first-time founders who have never navigated that third phase, this episode is one of the clearest explanations of how that game actually works.

Leo brings a rare dual perspective to fundraising advice: he thinks like an engineer and communicates like an investor. One of the most useful threads throughout the episode is his emphasis on respecting a VC's time and attention. With 50 to 100 cold emails landing in his inbox every week, Leo makes it clear that founders who stand out do so not by explaining everything upfront, but by treating their outreach more like a movie trailer than a plot summary. Two or three genuinely compelling data points, delivered concisely, will outperform a five-paragraph essay every time.

Leo is also refreshingly honest about what happens during the diligence phase and what kills momentum. His take on chasing disengaged investors is one of the sharpest pieces of advice in the episode: if a VC isn't visibly excited after your first meeting, no amount of follow-up is going to move them into the top 1% of their deal flow. The time you spend trying to convert a skeptic is time you are not spending with someone who is already leaning in. This is a mindset shift many first-time founders need to hear.

Finally, Leo makes a strong case for stage-appropriate, seed-specific funds over multi-stage giants when building out a cap table. He backs it up with his own data, noting that at Humba, roughly 65 to 70 percent of portfolio companies graduate to a Series A, but in only about 15 percent of cases does the multi-stage fund that wrote the seed check end up leading that next round. Taking money from a big name fund does not guarantee easier future fundraising, and if that fund passes on your A, it can actively hurt you by sending a bad signal to the market.

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.

Jesse brings a rare dual perspective to this episode. Having built and sold his own company before becoming a VC, he speaks to founders as someone who has genuinely sat on both sides of the table. One of the most refreshing threads throughout the conversation is his honesty about what VCs actually go off of at the pre-seed stage: almost nothing. With data rooms described as "ghost towns," Jesse explains that social proof and momentum matter disproportionately, not because VCs are lazy, but because there is simply very little else to evaluate. This reframes the fundraising process less as a merit contest and more as a momentum-building exercise, with strategic meeting sequencing playing a bigger role than most founders realize.

Jesse also gives unusually direct feedback on pitch decks, pushing back on some of the most common slides founders spend hours perfecting. The TAM/SAM/SOM slide, the hockey stick revenue projection, and the bloated advisory board are all called out as doing more harm than good in most cases. Instead, he wants to see a team slide with punchy, concrete achievements, early evidence of traction, and a go-to-market rooted in a specific ICP rather than a list of channels. His two-by-two framework of "conviction versus coachability" is a memorable and genuinely useful lens for founders thinking about how they come across in that critical first meeting.

Perhaps the most underrated part of this episode is Jesse's advice on what to look for in a VC. He pushes founders hard to actually interview their investors, asking about reserve strategy, deployment cycle, and how they show up when things go sideways. He also makes a pointed case for matching fund size to your ambitions, noting that smaller funds have many more "paths to victory" and can generate strong returns without needing a unicorn outcome from every bet. For first-time founders who default to chasing the biggest name brand funds, this is a perspective worth sitting with.