If you're getting ready to raise—or already in the middle of it and not getting the responses you hoped for—this episode will change how you think about pitching. Jayla sits down with Diana Wilson, a seasoned executive who has raised over $100M and taken Deckers, the now-billion-dollar lifestyle brand, public. Diana unpacks one of the biggest reasons first-time founders fail to get funded: they're busy selling the beauty of their business, but never answering the one question every investor is silently asking—what's in it for me?

In this episode, you'll learn:

The financial mistakes that instantly weaken a pitch
Why "hockey stick" projections can destroy credibility
Diana's founder pet peeves—and why they might be costing you the deal
How to use milestones and funding tranches to tell a more believable story
The soft skills that make investors trust you
How to follow up in a way that builds long-term relationships

If you are building your first company and trying to raise money, this conversation will help you pitch smarter, avoid the mistakes that turn investors off, and understand what actually gets people to lean in.

Listen to the end when Jayla brings on a special guest who practicies live in front of Diana.

Don't have time to take notes? You can download Diana's Three Pillar Framework HERE for free.

Guest Bio:

Diana Wilson is a committed and success-driven leader who is passionate about helping companies and individuals turn uncertainty and change into opportunity and growth. With more than 30 years of experience across strategy, finance, and operations, she has raised over $100 million, led companies through high-stakes growth, including taking Deckers public, and built high-achieving teams that perform under pressure. Today, she advises leaders and early-stage founders through pivotal moments of growth and change. Connect with Diana on Linkedin and follow her substack Wit & Wisdom here. https://substack.com/@dianamwilson

About Your Host

Jayla Siciliano is an entrepreneur with 25+ years in consumer brands, product, and marketing. After raising her first angel round against all odds and later appearing on Shark Tank, where she closed a deal with Mark Cuban, she now helps founders become fundable, confident, and ready to attract the right investors. Entrepreneurship changed her life, and she's on a mission to help first-time founders raise their first round of angel funding and change theirs too.

Join the fund raising conversation with Jayla on LinkedIn.

Disclaimer

The information in this podcast is educational and general in nature and does not take into consideration the listener's personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice.