Deck to Check Recap: Five Essential Takeaways for Founders

Deck to Check with Angel the Angel returned this month—and let’s just say, if there’s a room where founders actually get answers (not just platitudes), this is it. With Angel Gambino leading the charge and a cameo from the formidable Gale Wilkinson, the session delivered a wealth of practical advice for founders navigating today’s unpredictable market.

Markets might feel as stable as a house of cards—uncertain macro conditions, an uninspiring IPO window, AI hype reaching fever pitch—but Angel and Gale cut through the noise with the kind of candid feedback and frameworks that help you focus on what actually moves the needle.

Event Highlights: Angel and Gale’s Top Insights

Both Angel and Gale brought the room back to fundamentals: founders win when they ask the right questions from the very beginning. Here’s a swift tour through the five big ones they challenged attendees to answer—and why they matter.

1. What Do You Truly Love (and What’s Your Edge)?

Angel kicked things off by stressing true founder passion and domain experience. She challenged everyone to build in a space they genuinely care about—with networks and know-how to back it up. Gale doubled down, asking founders to name actual customers and design partners they could reach out to today. The day’s refrain? That unfair advantage is usually earned, not invented.

2. What Are Your Specific Goals (and Your Number)?

No more generic vision statements. Angel and Gale pushed every founder to define crystal-clear business, impact, and life goals. They encouraged modeling personal financial “numbers” and exit scenarios. Gale offered up practical frameworks for mapping revenue, ownership, and the real odds of hitting big exits versus building smaller, more profitable companies.

3. Should You Even Chase VC?

Gale didn't mince words: not every great company is a VC-fit, and most founders will get better outcomes without taking the classic venture path. The discussion broke down the trade-offs between raising from angels, using debt, chasing profitability, or scaling for a moonshot. Angel pressed founders to get comfortable with why and when to choose certain funding paths—and how staying capital efficient can keep the dream (and your equity) alive.

You can learn more about alternative funding paths from our previous Mentor MasterClasses with Grace Belangia, startup ecosystem builder and founder of The Clubhou.se here, and Marcia Dawood, Chair of the SEC Advisory Committee for Small Business Capital Formation here

4. Are You Hitting the Right Traction Milestones?

If you don’t know your benchmarks, you’re already behind. Angel mapped out must-hit metrics for many startups across multiple sectors ($2M ARR in two years, $5M the year after, $100M for true venture scale) and stressed moving at a pace that matches aspiration. Gale encouraged founders to embrace fast feedback loops and iterate messaging, ICP targeting, and go-to-market approach in real time, not theoretical time.

5. How Much Should You Really Raise?

The loudest applause came after a conversation about capital efficiency. Both speakers agreed: Don’t let easy money tempt you. Only raise what you need to hit the next critical milestone and always know your true resource requirements. The advice: “Milestones first, dollars second.” Staying lean keeps options wide open.

Why Deck to Check Works

What makes Deck to Check virtual events so effective? It’s the trusted, candid environment: founders and investors in the same room, asking hard questions, and giving honest answers. No conference-stage ego, just operators and investors who’ve been in the trenches—ready to sanity-check your pitch, numbers, and plan.

• Active feedback: Direct, personalized advice you can put to work immediately.

• Intimate connections: Smaller groups foster deeper conversations—think quality over quantity.

• Growth mindset: Founders leave with clarity and concrete next steps, not just inspiration.

  
  

You can register for an upcoming Deck to Check here. 

Mercury: Powering the Community

Thanks to Mercury for their ongoing support—connecting founders with banking designed to keep them moving quickly and confidently. Their team is on hand to help all Deck to Check attendees open accounts with lightning speed. More on that here.

Closing Thoughts

Summing up, this session of Deck to Check was a masterclass in founder focus—how to ask sharper questions, benchmark your progress, and chart a smarter path to fundraising success (or even ditch it for a cleaner play). If you’re a founder or investor looking to get real answers, actionable frameworks, and a direct line to seasoned experts, this is your room.

Hope to see you at the next session—bring your toughest question and your boldest goal.