S2E8: Founders: The Easy Way to Land Angels, Fast - Jaclyn Johnson, CEO - Cherub

Jaclyn Johnson is a powerhouse entrepreneur, investor, and advocate for women in business.

By 35, she had already launched and sold two multimillion-dollar companies, including Create & Cultivate, a first-of-its-kind platform for female entrepreneurs that scaled to eight-figure revenue and partnered with Fortune 500 brands like Amazon, Mastercard, and Microsoft.

Now, she’s back with Cherub, a double-sided marketplace designed to bridge the gap between underrepresented founders and democratizing access to category-defining companies. As both an angel investor and advisor, Jaclyn has backed businesses like Away, Live Tinted, and Chillhouse, bringing hard-won experience from her own journey into the founder–funding relationship.

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In this conversation, we break down:

• Jaclyn’s origin story: why she built Cherub
• How she approaches angel investing and the lessons she’s learned
• What makes a great angel pitch (and what doesn’t)
• The realities of being an accredited investor
• Why representation in funding isn’t just moral, it’s market-changing

Chapters

00:00 The Importance of Angel Investments

02:49 Jaclyn’s Journey as a Founder and Investor

05:41 Understanding Angel Investors vs. Venture Capitalists

08:28 The Role of Angel Advisors

11:23 Building Relationships with Angels

14:15 The Power of Brand Fame

17:25 Cherub’s Mission and Deal Flow

20:07 Educating Angels and Standardizing Investments

23:13 Creating Effective Fundraising Pages

26:12 The Role of Analytics in Fundraising

29:04 Onboarding Founders to Cherub

32:01 Connecting with Angels: Best Practices

35:03 Diversifying the Investment Landscape

37:58 The Future of Angel Investing

40:35 Special Offers for Founders on Cherub

Guest Bio

Jaclyn Johnson is the founder of Cherub and creator of Create & Cultivate, which she scaled to an eight-figure exit while reshaping how brands and communities support female entrepreneurs. Named a Forbes 30 Under 30 and an Adweek Disruptor, Jaclyn is an angel investor and advisor to companies including Away, Live Tinted, and Chillhouse. She’s dedicated to making capital and community more accessible for underrepresented founders while equipping the next generation of women entrepreneurs to scale.

Who Should Listen

• Founders raising their first angel round
• Entrepreneurs seeking representation and resources
• People curious about Angel Investing and how to get started
• Operators looking to understand the angel landscape

Music Credit

“Neptuno” – Phondupe (Album: Onykia)

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