Rebecca Cassava — CEO & Co-founder of Dealmaker

Dealmaker is a digital fundraising platform that allows founders to easily raise capital by building an online investor funnel—making selling shares as simple as selling products online.

⭐ What We Discuss in This Episode

1. What Dealmaker Actually Does

A platform that lets founders set up an online storefront to sell equity

Helps founders drive traffic to their investment offering

Supports everything from seed rounds to $75M+ community-led raises

Enables thousands of small investors to join, support, and evangelize the brand

2. The Power of Community Capital

Why thousands of believers beat a few controlling investors

How community investors are 54% more engaged

Real examples like Boxabl raising hundreds of millions

Why community rounds give founders more control and fewer strings attached

3. Who Should Use This Type of Raise

Companies with a message that resonates quickly online

Consumer-facing brands, tech, robotics, real estate, and emerging industries

Any founder who can explain their value visually or in a 30-second TikTok

4. How Rebecca Built Dealmaker

Using her legal background to help founders access capital more easily

Raising capital for Dealmaker three times using her own platform

Leveraging her own community to generate explosive growth

Why “eating your own dog food” accelerated the company

5. Growth Challenges & Scaling Up

Rebecca shares the biggest hurdles she and her team faced:

Saying “no” to customers that weren’t a good fit

Implementing organizational structure as a fast-growing startup

Taking the vision out of her head and putting it on paper

Setting KPIs to drive accountability

Killing bets that aren’t supported by data

She discusses how the Scaling Up One-Page Strategic Plan helped:

Clarify the company’s long-term vision

Communicate direction clearly and repeatedly

Hold the team to measurable outcomes

6. Advice for Founders Scared to Raise Capital

You set the terms—no unwanted board seats or controlling investors

A community raise lets you maintain power while gaining capital

Raising even $300K–$1M can completely change your trajectory

A conversation with the team can clarify whether you’re ready and how to prepare

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