Conversations with Offor

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Raw conversations about the decisions that define who you become. Host Ify Walker sits down with leaders across industries who've navigated their defining moments: the career pivots, the decisions that changed everything, the moments when leadership mattered most. These are honest conversations about what it takes to lead when the stakes are highest. For founders, executives, and anyone facing decisions that will define their path forward.

Episodes

  1. 07/23/2025

    Exit Interview: Building Democracy's Highway with Erin Hill

    At eight years old, Erin Hill announced she wanted to be president. At twenty-something, she joined a four-person political tech startup because she believed small-dollar donors could change democracy. Seventeen years later, she walked away from ActBlue after helping it process nearly $11 billion in political contributions. Erin's journey reveals what happens when public service meets entrepreneurship during the most transformative period in political fundraising history. From opening envelopes filled with five-dollar checks from first-time donors to leading a technology company through presidential elections, she shares the rarely told story of building infrastructure that holds democracy together. Through the 2009 crisis that nearly killed the organization, the relentless pressure of doubling volume every election cycle, and the isolation of leading when failure isn't an option, Erin explores what it means to carry responsibility for other people's dreams. She discusses the physical toll of the 2020 election, why she wished she'd built peer networks sooner, and the moment she realized the work had outgrown her. Key topics: Growing up in a family where public service was "part of the fabric"Joining a startup at the intersection of politics and technologyThe 2009 organizational crisis and how they survived itScaling from millions to billions while maintaining trustWhy leadership became more isolating as the company grewThe difference between being irreplaceable and being stuckHow to know when your leadership chapter is completeBuilding systems that outlast the founderThis conversation challenges the myth that great leaders should never step down and reveals why sometimes the most courageous decision is knowing when to let go.

    1h 41m

  2. 07/02/2025

    Exit Interview: Building Generational Wealth with Dr. Ebbie Parsons

    Dr. Ebbie Parsons had a negative $300,000 net worth, a three-month-old baby, and a half-million-dollar salary when he asked his wife: "Can I quit and start my own business?" Her answer changed everything. Ebbie's story traces from growing up in majority-Black Detroit where he learned relationship-building from his father, to walking away from corporate success to build Yardstick Management into a nationally recognized consulting firm. He takes us through the early struggles—including a fraudulent contractor who nearly destroyed everything—and the strategic decisions that led to an 8-figure exit. We explore what it really means to build generational wealth, from sacrificing sleep and health while refusing to compromise on family time, to the emotional complexity of selling what his wife called "their baby." Ebbie reveals why he chose to build in public long before it was trendy, how authenticity became his competitive advantage, and the moment he decided to spend $300,000 competing directly with McKinsey. Key topics: The difference between being rich versus wealthyBuilding relationships as your greatest business assetWhy he never hired employees for the first six yearsCreating multiple revenue streams for business resilienceThe real cost of entrepreneurial success on health and familyHow growing up seeing Black excellence shaped his confidenceWhat "enough" actually looks like—and when to walk away This conversation challenges assumptions about work-life balance and reveals why building generational wealth requires sacrifices most people aren't willing to make.

    1h 49m

  3. 06/18/2025

    Exit Interview: The Loneliness of Leadership with Carrie Siubutt

    Carrie Siubutt, former CEO of SimpleHealth, shares what happens when personal resilience meets professional burnout—and why stepping away can be the strongest decision you make. Carrie's journey spans from being diagnosed with a rare neurological condition at 11, to building a $75M telemedicine company with 200 employees, to facing regulatory changes and market turbulence that forced devastating choices. She opens up about the isolation of CEO leadership, the unique pressures facing leaders of color, and how wanting to be liked became her greatest vulnerability. We dive deep into what Carrie calls "the work twisties"—those moments when high-performing executives lose their footing and can't see a path forward. She reveals the physical and mental toll of executive burnout, the 12-month recovery process that followed, and how she's reinventing herself in an entirely new industry. This isn't about bouncing back—it's about the wisdom that comes from breaking down. Key topics: How disability became her leadership superpowerThe double standards facing CEOs of colorWhy wanting to be liked became her biggest weaknessLeading through regulatory crisis and market collapseRecognizing the signs of executive burnoutThe cost of caring too much about your teamBuilding sustainable recovery habits after trauma This conversation reveals why we need honest stories about executive mental health and the courage it takes to choose recovery over revenue.

    1h 33m

  4. 06/11/2025

    Exit Interview: The Work Twisties with Kanya Balakrishna

    Kanya Balakrishna, Co-Founder and CEO of The Future Project and Future Coach, shares a story most founders never tell publicly: what it's like when everything falls apart. In this raw conversation, Kanya takes us from building a $15M nonprofit with 120+ staff to facing a catastrophic funding crisis that forced the organization down to just 10 people. This isn't about failure or success—it's about the messy, instructive middle that doesn't make headlines. We explore what Kanya calls "the work twisties"—those moments when leaders lose their sense of position and can't see the path forward. She discusses the isolation of crisis leadership, the shame spiral that follows major setbacks, and how the pandemic unexpectedly created space for rebuilding something better. Key topics: ​The hidden costs of rapid nonprofit growth​Why "persistence" isn't always a strategy​The sacrifice trap that catches mission-driven leaders​How to lead when you can't see the way forward​Building company culture vs. making hard decisions​What it really takes to start over This conversation reveals why we need better language for the difficult phases of leadership and the importance of peer support during crisis.

    1h 53m

  5. SEASON 1, EPISODE 1 TRAILER

    Welcome to Exit Interview: Why We Need the Stories That Don't Make Headlines

    Exit Interview is a limited series exploring the entrepreneurial stories that don't make headlines - the complex realities of building, scaling, and ultimately stepping away from the companies you create. Host Ify Walker sits down with founders and first-time CEOs to discuss not just the beginning of their journey, but the end: the decisions that defined them, the costs they didn't anticipate, and what they learned about themselves when the stakes were highest.

    2 min

Trailer

About

Raw conversations about the decisions that define who you become. Host Ify Walker sits down with leaders across industries who've navigated their defining moments: the career pivots, the decisions that changed everything, the moments when leadership mattered most. These are honest conversations about what it takes to lead when the stakes are highest. For founders, executives, and anyone facing decisions that will define their path forward.

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