Seed Money

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98 | Why a $10,000 Check Can Open Bigger Funding Doors

September 22, 2026

Jayla Siciliano breaks down why early-stage founders should not dismiss small checks when raising their first round. The episode focuses on how a modest commitment can create the validation needed to unlock larger angel, strategic, and investor conversations later.In this episode, Jayla explains why most founders are not ready for VC funding right away and why smaller early checks can matter more than the dollar amount itself. She also shares how founders without wealthy networks can still bu...

97 | Fund the Next Milestone, Not the Billion-Dollar Dream

September 15, 2026

In this episode, Jayla explains why waiting until January to set annual goals can sabotage fundraising plans, and why fall is a better time to map out milestones, funding needs, and investor strategy. And she's sharing practical fundraising advice from her recent Seed Money office hours sessions. If you're raising money in the next 6 to 12 months, this episode is about setting the right goals before the year gets away from you. Key topics Jayla argues that January is the worst time to set g...

96 | Stop Pitching, Start a Relationship: Ethan Mayers on What Investors Really Want

September 02, 2026

In this episode Jayla Siciliano sits down with Ethan Mayers, also known as "The Pitch Destroyer," to unpack what investors actually want, how founders should approach fundraising, and why relationship-building matters more than "the ask". Ethan shares hard-won perspective from years of helping founders sharpen their pitch, build stronger investor relationships, and understand the real purpose of a pitch deck: not to close a deal, but to start a conversation. He explains why investors are ofte...