How to Raise $20M by Breaking the #1 Fundraising Rule w/ Alexander Wulff

Seed Money

If you’re walking investors through your pitch deck slide-by-slide. Hiding the biggest risk in your business until the very end or treating meetings like job interviews, you’re making the same mistakes that keep founders stuck in the endless cycle of “we’ll pass for now.”

Fundraising isn’t just about your traction or your vision. It’s about breaking the pattern-recognition bias VCs use to filter out anything that doesn’t look like their last big win.

If you want to raise serious capital, you have to show them why you’re the outlier worth betting on.

Alexander Wulff has raised over $20 million (including an $8 million seed round) by doing the opposite of what founders are usually told. Today, he’s building Nume, an AI CFO built to replace the spreadsheet chaos founders like you deal with every week.

Why do we need to work hard for warm intros? Does presenting our pitch deck actually work against us?

In this episode, Alexander shares what actually works when you’re raising capital, especially when your model doesn’t fit the mold. You’ll learn how to lead with your biggest risk (instead of trying to hide it), and how to reframe the pitch deck as a teaser.

Topics Covered;

• How Alexander raised $20M+, including an $8M seed round

• The “tech plus service” strategy that scared off most VCs

• What 100+ failed VC pitches taught him about objection-handling

• Why cold outreach almost never works (and how to get warm intros fast)

• How to structure a pitch that starts with your biggest risk

• Why “average energy” founders rarely win VC money

• Why passion, performance, and “controlled craziness” matter more than polish

• Smart ways to use AI to make financial ops proactive, accurate, and founder-friendly

Guest Bio

Alexander Wulff is the co-founder and CEO of ScaleUp Finance, which began as a CFO-as-a-Service platform combining technology and human expertise to help startups manage their financial operations. Today, that vision has evolved into Nume—the world’s first true AI CFO, built to eliminate the spreadsheet chaos and reactive reporting that holds founders back. Alexander’s entrepreneurial journey started early. He published a bestselling book at just 19 and launched his first venture at 20, turning dormant university-held patents into a funded startup. His experience spans fundraising, fintech innovation, and scaling high-growth companies, and he brings a unique mix of operational insight and bold, contrarian thinking to everything he builds. Visit https://www.scaleup.finance/ to learn more and connect with Alex on LinkedIn.

About Your Host

Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she’s on a mission to help early-stage entrepreneurs turn their ideas into reality!

Connect:

Website: https://seedmoneypodcast.com/

Instagram: https://www.instagram.com/jaylasiciliano/

Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/