The Founders' Journey

Rallyday Partners

On The Founders' Journey podcast, we explore the heart and soul of great founders and their journey to build the company of their dreams. Once a month in a 60-minute conversation, you will learn about emerging industries and innovative business models while discovering how to apply the founder’s mindset to your everyday work and life.

  1. Chip Conley, Founder and Executive Chairman, Modern Elder Academy (MEA)

    MAR 3

    Chip Conley, Founder and Executive Chairman, Modern Elder Academy (MEA)

    What happens after you build the company? After the exit? After the identity you wrapped yourself in no longer fits? In this no-BS conversation, Ryan Heckman sits down with Chip Conley, founder of Joie de Vivre Hospitality, former Head of Global Hospitality & Strategy at Airbnb, bestselling author, and founder of the Modern Elder Academy. Chip shares how he raised $1.1M at 26 to buy a broken-down motel in San Francisco, turning it into 52 boutique hotels before selling to Hyatt. But the most pivotal chapter was not the growth. It was the unraveling. Burnout, personal loss, and a near-death experience forced him to confront a deeper question: Who am I if I am not this company? That reckoning led him to Airbnb, where he joined as a 52-year-old mentor to Brian Chesky during the company’s meteoric rise. Together, they navigated scale versus soul, ego versus service, and what it means to lead from behind. This episode explores the difference between knowledge and wisdom, how to reframe accountability with your team, why midlife is a chrysalis not a crisis, and how founders can move from return on investment to ripple of impact. For founders focused on building value, this is a reminder that you are also building a life, including your own. Chip Conley is not an investor in one or more of Rallyday Partners private funds and did not receive any cash or non-cash compensation for participating in this podcast. To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com

    59 min
  2. David Gilberg, Founder, CEO & President of Elder Care Homecare

    12/02/2025

    David Gilberg, Founder, CEO & President of Elder Care Homecare

    In this episode of The Founders’ Journey, we sit down with David Gilberg, Founder, CEO, and President of Elder Care Homecare, who made the bold leap from investment banking at Morgan Stanley to building a purpose-driven home care company alongside his mother. What began as a small family practice rooted in compassion has grown into a leading concierge home care provider serving more than 600 patients daily across four states.  David shares how his mother’s lifelong commitment to seniors shaped Elder Care Homecare’s unique model, one that blends social work and nursing to deliver truly human-centered care. We talk about what it took to scale from a handful of clients to thousands of caregivers, the culture that keeps quality at the center, and the purpose statement that guides every decision the company makes. Listeners will hear powerful lessons on trading success for significance, staying grounded while growing fast, and what it means to “meet the moment” as a leader, parent, or founder. David’s journey is a reminder that real care is built one relationship, one heart at a time. David Gilberg is not an investor in one or more of Rallyday Partners private funds and did not receive any cash or non-cash compensation for participating in this podcast. To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com

    1h 1m

Ratings & Reviews

5
out of 5
13 Ratings

About

On The Founders' Journey podcast, we explore the heart and soul of great founders and their journey to build the company of their dreams. Once a month in a 60-minute conversation, you will learn about emerging industries and innovative business models while discovering how to apply the founder’s mindset to your everyday work and life.

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