Bailey & Company

Managing Partners John Bailey and Alex Bailey make all investment decisions directly. Both brothers co-founded and operated Healthways and HealthStream before converting their wealth into a family office structure. They sit on portfolio-company boards and do not delegate allocation authority to external managers or a professional CIO.

Bailey & Company operates as a single family office deploying the Baileys' personal capital. It does not manage outside money, charge management fees, or market itself as a fund. The firm uses the permanent-capital advantages of a family office to hold positions without LP-driven exit timelines.

The firm concentrates on healthcare IT, digital health, and enterprise software — sectors where its principals have direct operating experience. HealthStream and Healthways, both co-founded by the Baileys, serve as the experiential anchor for diligence in these verticals. FinTech investments appear in the portfolio as adjacency bets where healthcare and payments overlap.

The firm's disclosed activity points to direct investments and co-investments alongside venture firms rather than broad fund-of-funds commitments. Its Palo Alto office facilitates co-investment sourcing with West Coast VCs, but Bailey & Company writes checks directly into companies, not into other managers' blind-pool vehicles.

The firm targets growth-stage and late-stage venture opportunities, consistent with its principals' preference for companies that have product-market fit and revenue traction. Early-stage bets are rare; the Baileys apply an operator's diligence lens that requires real customer contracts and unit economics.

The underlying wealth originates from healthcare services and technology entrepreneurship. John and Alex Bailey co-founded Healthways, a population-health management company that reached over $700 million in revenue, and HealthStream, a publicly traded healthcare workforce platform. The 2016 sale of Healthways to Sharecare crystallized a significant liquidity event.

No separate philanthropic foundation is publicly associated with Bailey & Company. The Baileys have been individually active in Nashville-area civic and healthcare workforce initiatives, but these activities appear to run through personal giving rather than a structured family-office philanthropic arm.