My name is Kaishon Holloway and I believe advocacy is not just a noun, it's a verb. And I show up every single day to prove it.
I don't just give keynotes. I start conversations.
I'm a Keynote Conversationalist, Culture Transformation Agent, and HR Pop Star who turns ordinary events into conversations people are still talking about long after they end. I thrive in keynote, fireside chat, and panel discussion environments where the topic meets the audience exactly where they are. I don't speak at audiences. I speak with them. My sessions are warm, a little witty, deeply human, and grounded in 13+ years of lived experience inside some of the world's most recognizable organizations.
I started my career in tech at 19 and have since led work across Customer Advocacy, HR, Employer Branding, Employee Advocacy, Diversity and Inclusion, Marketing, Go-to-Market Strategy, and Social Impact at Indeed and Peloton.
My life's mission is to use my voice to effect positive change for the most vulnerable communities in our society. My passion sits at the intersection of technology, mental resilience, and self-actualization.
I live openly as a proud Gay, Black man with Bipolar Disorder and document that journey in my blog, Kaipolar Diaries. I don't share that to be brave. I share it because psychological safety is not a buzzword to me. It's personal. And when I stand on your stage and talk about mental wellness and building financial resilience before times of crisis, your audience knows that I mean it.
My signature topics:
▪ Mental Wellness in High Performance Environments: Thriving Without Burning Out
▪ The Rainy Day Plan: Building Financial Resilience Before Times of Crisis
My goal is simple: to empower myself and others one day at a time while building a better future for ALL.
Take care of yourself and be kind to others.
Speaker inquiries: kaishon@kaishonholloway.com
Speaking Topics
▪ Mental Wellness in High Performance Environments: Thriving Without Burning Out: High performance and mental wellness are not opposites. But for too long, hustle culture has convinced us otherwise. I spent 13+ years navigating some of the world's most demanding organizations while privately managing grief, burnout, and a Bipolar Type I diagnosis. In this session, I pull back the curtain on what it actually takes to sustain peak performance without sacrificing your mental health. Honest, practical, and delivered with my signature warmth and wit, this talk meets your people exactly where they are.
▪ The Rainy Day Plan: Building Financial Resilience Before Times of Crisis: Nobody plans for a mental health crisis. But the people who weather them best almost always have one thing in common: they prepared before the storm arrived. I learned this the hard way, accumulating over $30,000 in medical and personal debt across multiple hospitalizations and manic episodes. In this session, I share the hard-won financial and emotional strategies that helped me rebuild stability, protect my future self, and get ahead of the chaos before it hit. This session sits at the intersection of mental health, financial wellness, and radical self-advocacy, and it is unlike anything your audience has heard before.
Speaking Engagements
2020 - 2026
▪ Unilever: "Addressing Non-Inclusion" Panel
▪ Execs in the Know (CX Summit): "Empowering Employees through Technology" Panel
▪ East Coast Executives: "The Future of Work Conversation: Black Male Edition"
▪ McDonald's and Out & Equal: "Intersectionality: The Black & LGBT Experience" Panel
▪ Wonsulting (Amplify Virtual Conference): "LGBT+ Professionals" Panel
▪ Casper: "Building Inclusion" Panel
▪ National Urban League (Digital Career Success Series): "Escaping The Resume Black Hole"
▪ SONY: OutLoud Presents | The Grit and Glamour: The LGTBQ+ Experience at Work with Kaishon Holloway
▪ Business Insider: Skills You Need to Land a Job in Diversity and Inclusion
▪ CNBC: Why Being Single Is So Expensive In The U.S.
▪ New York Urban League Young Professionals: "Navigating Your Career & Mental Health Journey" Panel
▪ UConn Stamford Micro Internship Program: Professional Development Fireside Chat
▪ Out in Tech Miami: Diversity, Equity, and Inclusion in Tech Panel
▪ Out in Tech x Pridelines: LGBTQ+ Professionals & Entrepreneurs in Tech Panel
2019
▪ University of Connecticut Career Day
▪ Circle of Change Leadership Conference
▪ Pluto: "Intersections of Workplace Diversity & Inclusion" Panel
▪ Salesforce: "Imposter Syndrome: Myth or Reality?" Panel
2018
▪ IAMPHENOM (VX Conference): "Marketing the Employer Brand in a Candidate-Driven Market" Panel
See me in action
CNBC: Why Being Single Is So Expensive In The U.S.
The number of single Americans has been steadily rising for several decades. Today, 46.4% of U.S. adults never married, are divorced, or widowed. But a single life today can come with an additional challenge: financial anxiety. A 2023 survey by Match revealed that the top three stressors for single Americans, excluding Gen Z, were all financial. So what’s causing so much financial anxiety among single Americans?