Earn Your Leisure – Episode Summary

Episode Title: The INSANE Reality of Being the Poster Child for Funding You Can't Get
Date: February 15, 2026
Guest: Jessica Spalding (Founder, Harlem Chocolate Factory)
Hosts: Rashad Bilal & Troy Millings

Episode Overview

This episode features an unflinching, real-time case study of entrepreneurship with Jessica Spalding, founder of Harlem Chocolate Factory. The discussion centers on the harsh realities of building a small business as a Black woman, focusing on the pitfalls of being a “poster child” for funding—and the painful gap between perception and reality. Spalding shares a first-hand account of scaling challenges, capital struggles, and what happens when media attention brings not opportunities, but new obstacles.

Key Discussion Points

1. Jessica Spalding’s Entrepreneurial Journey (03:22)

• Origin Story: Jessica started Harlem Chocolate Factory in 2015 after winning a $15,000 business plan competition while she was unemployed—an opportunity she discovered at the library with her children.
• Rapid Growth and Media Attention: Early media exposure (including mentions from Sam Adams and Oprah) led to a flood of orders, forcing Jessica to scale quickly/inadequately from a two-foot table to a small commercial kitchen.
• Business Model Shifts: Initially focused on wholesale and corporate gifting, Jessica had to pivot to retail and brick-and-mortar—transforming the business model and creating labor-intensive customer service obligations.
  • “I'm spending 45 minutes explaining to people why my chocolate costs more than what's at the corner store.” (05:09)

2. The Double-Edged Sword of More Orders (06:39)

• Growth ≠ Profitability: Friends' well-intentioned support (“let me get you more orders”) was overwhelming rather than helpful.
  • “You're actually low key, drowning me.” – Jessica Spalding (06:39)
• Jessica describes how more small, piecemeal orders actually worsened financial and operational strain, especially with limited production capacity.

3. Rethinking the Business Model (08:00)

• New Direction: Focus on high-volume, contracted partnerships (“it rhymes with All Star”) and pivot away from individual consumer sales.
• Strategic Scaling: Emphasizes the need for breakpoints that allow real economies of scale—especially in chocolate manufacturing, where co-packers are only viable at high order volumes.
• Investor Skepticism: Investors pushed for a grocery store channel, but Jessica insisted, “that's where our business would go to die. Because that's what everybody else did and that's why their businesses are closing.” (09:22)

4. Learning to Define the “Right” Model (11:20)

• Advice for Entrepreneurs: Start with metrics that allow for sustainability and personal income. Don’t get caught chasing the biggest market—sometimes, smaller-scale, higher-margin models are more sustainable.
• Jessica candidly critiques the prevalent image of the successful Black woman founder, which is often used for PR while masking real revenue struggles.
  • “Black women... We're the most educated, most everything. But the reality is we make the least amount of revenue out of every group.” (11:35)
• Emphasizes the importance of a business model that secures owner livelihood from the beginning, not just operations.

5. The Hidden Costs of Direct-to-Consumer (13:39)

• Hiring staff and operational support is essential—volunteer labor (family, community) isn’t reliable or fair.
• Technological aid (AI, etc.) helps, but cannot replace human capital needs in retail.

6. The Illusion of Support – Poster Child Without Funding (15:49)

• Jessica became the public face of NYC’s Funds Finder website—but when she applied for capital, she was offered nothing.

  • Podcast Host (17:26): “You were essentially the poster child for that. Your face was on there.”
  • Jessica (17:35): “Yes.”
  • Podcast Host (17:35): “But you couldn't get funding.”
  • Jessica (17:38): “Zero funding options available is what it said to me.”

• Public Perception vs. Reality: Recognition brings assumptions of success—which can actually reduce community support when it’s most urgently needed.

7. Systemic Roadblocks to Funding (21:38)

• Shifting Criteria & Goalposts: Funding was easier to access when Jessica’s story fit a “supportable” narrative (single mother, no job). As she grew and succeeded, institutions imposed ever-changing demands, repeatedly denying her capital at critical growth moments:
  • Get contract → Prove sales → Show invoices → Wait for payment → Still denied for “risk” reasons.
  • “That's when I realized, like, oh, everybody's lying to me. Y'all hate me, and let me just stop.” (23:53)
• Marketing vs. Real Support: Jessica reflects on being used as a symbol for empowerment while getting little tangible backing.

8. The GoFundMe Appeal & Community Ownership (25:14)

• Immediate Needs: Raising $50,000 to clear debt and cover deposits to fulfill new contracts—bridge funding needed now, as formal options drag out for weeks/months.
• Vision for the Future: Hopes to eventually enable community participation through shared ownership structures.

Notable Quotes & Memorable Moments

• On being publicly celebrated but unsupported
  “People were like, responding to our GoFundMe by saying, like, well, you on funds finder? Or there's like, hey, I found the link to the New York City funds finder. Go on there. Like, oh, wait, your face is on there.” – Jessica Spalding (17:45)

• On endless moving targets from funders
  “The goalpost moves. It was get a contract and come back. Come with a contract. Yeah, but how do we know it sells?” – Jessica Spalding (22:57)

• On the emotional toll of entrepreneurship
  “I'm basically breaking even in this retail space. So it's just. It's led us to really, really, really pay attention to how we need to shift the model and...do the thing that I was afraid to do in the first place, which is go after what we truly needed.” (06:55)

• On support systems and their limitations
  “My cousin want to come work for me. My cousin bills ain't gonna go nowhere. I have to pay her for the day. She can't volunteer.” – Jessica Spalding (13:54)

• Keen Observation About PR & Funding
  “I think that black women are the marketing. I think that it's very, very easy. I think that's the way in to prove that you show support for the community.” – Jessica Spalding (19:05)

Timestamps for Key Moments

• Jessica’s business beginnings & early growth: 03:22–05:50
• Problems with too many small orders: 06:39–07:38
• New business model direction & scaling: 08:00–10:43
• Advice on business models and income: 11:20–14:30
• Funding struggles & the Funds Finder paradox: 15:49–18:55
• Institutional goalpost shifting: 21:52–24:26
• Roots in Harlem/community ties: 21:20–21:36
• GoFundMe explained: 25:14–26:48

How to Support & Stay Connected

• Donate or learn more: harlemchocolatefactory.com
• Instagram: @harlemchocolatefactory

Tone and Takeaway

This episode is candid, urgent, and inspiring—a corrective to the myth of guaranteed entrepreneurial progress. Jessica’s story is both a cautionary tale and a rallying cry: real sustainability requires more than publicity, more even than hard work. It needs access, infrastructure, and honest support. The Earn Your Leisure hosts applaud her transparency and encourage direct community backing during this critical juncture.