92 | Announcing Office Hours- Join us monthly
Summer is slow for investors. Don't waste it.
Fall fundraising starts now.
Use the summer to tighten your deck, build your investor list, fix the gaps, and get clear on your funding strategy—so when investors are ready to talk, you're ready too. Listen for what to do this summer to be ready for f…
93 | 5 Things to Do This Summer So Investors Take You Seriously This Fall
If your fundraising momentum stalled this winter or spring, summer is not the time to disappear. It is the time to fix the gaps before investors start paying attention again in the fall. In this episode, Jayla shares a simple 5-part summer reset plan to help early-stage founders turn customer conve…
94 | 10 Must-Dos Before Asking for Investor Introductions
Warm introductions can open doors, but only if you use them the right way. Too many early-stage founders ask for investor intros before they know whether that investor is actually a fit, which can lead to awkward asks, weak pitches, and getting ghosted. In this episode, Jayla breaks down the resear…
95 | Build Your Angel Investor List Before Fall & Stop Wasting Time On The Wrong Investors
Finding investors can feel like the most intimidating part of raising your first round, especially if you were not born into a wealthy, well-connected network.
But the answer is not to pitch everyone with "angel investor" in their LinkedIn bio or assume anyone with money could write you a check. T…
96 | Stop Pitching, Start a Relationship: Ethan Mayers on What Investors Really Want
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 fou…
97 | Fund the Next Milestone, Not the Billion-Dollar Dream
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. I…
98 | Why a $10,000 Check Can Open Bigger Funding Doors
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 wh…
99 | How to Reframe Red Flags So Investors Don't Run
Jayla Siciliano explains how founders can turn perceived red flags into clear, confidence-building narratives for investors. The episode focuses on a common fundraising mistake: overexplaining a situation that the founder is already anxious about, which can make a neutral fact sound like a major pr…
You Can Be 100% Committed Without Quitting Your Day Job
If you're afraid to talk to investors about funding your startup while you still have a day job, this episode is for you. Jayla talks about why splitting your time doesn't have to be a red flag in a first raise, and she highlights what investors actually care about instead.The big takeaway is simpl…
101 | 5 Signs You're Chasing The Wrong Investors
If you're a first-time founder trying to raise money and keep hearing crickets—or worse, polite rejections—this episode is for you.
In this episode, I'm breaking down the 5 biggest signs you're chasing the wrong investors and wasting time on people who were never going to fund you in the first pla…
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