Earn Your Leisure

Rashad Bilal is a financial advisor who built a practice in the New York area before co-founding the podcast. Troy Millings is a former educator and athletic director who brought his background in coaching and school administration into the firm's approach to community financial literacy. The two met through their shared Bronx network and recognized an unmet demand for investment and business education delivered in an accessible, culturally credible format.

Deal flow comes predominantly through the platform itself — founders appear on the podcast as guests, audience members surface opportunities, and the firm's event franchises create in-person networks that generate proprietary introductions. This inbound model is a structural departure from the typical GP fundraising process; companies often pursue Earn Your Leisure's audience exposure as much as its capital.

Earn Your Leisure is fundamentally a media company with direct investment activity. It does not manage third-party capital through a traditional fund structure, nor does it trace back to a single family's wealth. The firm generates revenue through content, live events, and brand partnerships, then allocates a portion of its balance sheet to venture investments that complement the content ecosystem.

The firm focuses on early-stage companies, typically pre-seed through Series A, where the Earn Your Leisure audience platform can meaningfully accelerate customer acquisition. Investments are concentrated in fintech, consumer technology, and culturally resonant brands that benefit from media-driven distribution.

The firm invests directly into operating companies and does not publicly disclose commitments to external fund vehicles. The known posture favors equity and equity-like instruments in startups where the founders value media amplification alongside capital, rather than passive LP stakes in institutional funds.

Invest Fest is Earn Your Leisure's annual live event that brings together thousands of attendees for panels, keynotes, and networking focused on investing and entrepreneurship. Speakers have included fund managers, professional athletes, and corporate executives. The conference serves simultaneously as a revenue stream, a brand tentpole, and an in-person sourcing channel for investment opportunities that emerge from attendee and speaker relationships.

Co-founders Rashad Bilal and Troy Millings make investment decisions jointly, drawing on Bilal's financial advisory background and the firm's internal research capabilities. The firm has not publicly named a dedicated investment committee or disclosed a formal CIO role, suggesting a founder-led decision process typical of operator-investor models at comparable scale.