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Earn Your Leisure
Rashad Bilal and Troy Millings' Earn Your Leisure turned a finance podcast into a media and early-stage investment platform reaching millions weekly.
Earn Your Leisure
Rashad Bilal and Troy Millings founded Earn Your Leisure in 2019 as a podcast translating finance and entrepreneurship for a generation the legacy wealth industry had largely ignored. What began as conversations in a Bronx barbershop grew into a multimedia business that reaches millions weekly across YouTube, live events, and social platforms. The firm operates at the intersection of financial education and cultural influence — a media company whose audience relationship has proven deep enough to support event franchises, merchandise, and direct investment activity. Earn Your Leisure participates across early-stage venture, media production, and live experiential events. Their investment footprint includes backing for fintech startups, consumer brands, and platforms that align with their educational mission. The firm has placed capital into early-stage ventures like the neobank Greenwood and has explored partnership structures with established operators to bring financial products to their audience. Geographically, the firm concentrates its investments in the United States, with particular attention to founders operating in the Atlanta, New York, and Bay Area startup ecosystems, mirroring the cities where the firm maintains a physical presence. November 2023: The firm expanded its institutional relationships through a content and investment-focused partnership with a major financial services brand, signaling a maturation beyond independent creator revenue (per public record). The podcast network has grown to include multiple shows covering crypto, real estate, and small business ownership, with the main program routinely hosting asset managers, athletes, and corporate executives. The audience spans retail investors, aspiring founders, and financial professionals who use the platform as a sourcing layer for ideas and operators they might otherwise miss. Structurally, Earn Your Leisure is an audience-first media company that deploys capital opportunistically rather than through a committed fund vehicle — making it less a family office than a content studio with a venture sleeve. The firm monetizes through advertising, ticketed events like Invest Fest, and equity positions in companies that benefit from the audience exposure the platform can deliver. This distribution-advantage model — where deal flow originates from a trusted media brand rather than from LP networks or banker relationships — remains rare in institutional investing and forms the core of the firm's competitive distinctiveness.
General information
Firm type
Asset Manager
Year founded
2019
AUM
Undisclosed
Location
Region
North America
Country
United States
City
New York
Corporate office
New York, NY, United States
Additional offices
Menlo Park, CA · San Rafael, CA · San Francisco, CA · Boulder, CO · Berkeley, CA · Atlanta, GA
Principals
Rashad Bilal
Co-Founder
Troy Millings
Co-Founder
Sector focus
Frequently asked questions
Who founded Earn Your Leisure and what is their professional background?
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.
How does Earn Your Leisure source the deals it invests into?
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.
Is Earn Your Leisure a single family office or a media company?
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.
What investment stages does Earn Your Leisure typically target?
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.
Does Earn Your Leisure participate in fund commitments or only direct deals?
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.
What is Invest Fest and how does it relate to the investment business?
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.
Who runs investment decisions at Earn Your Leisure?
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.
Profile maintained by Altss using OSINT (open-source intelligence), regulatory filings, licensed data partners, and verified direct submissions. Read the methodology. Last updated: . Continuous refresh with full update cycles at least every 30 days.
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