It Doesn’t Have to Be This Hard | Claude Silver, Chief Heart Officer at VaynerX
Wed Dec 17 2025
From a 93‑day Outward Bound in the Colorado Rockies to hiding her sexuality at work and now holding impossible DEI conversations as Chief Heart Officer at VaynerX, Claude Silver shares why being yourself at work is both risky and necessary: change the song in your head, remove shame, add tenderness, and stop asking humans to act like machines.
Key Takeaways
• Back‑nine season: joyful service, big heart, total goofball.
• Wilderness wake‑up: 93‑day Outward Bound → “get another song in your head.”
• Dyslexia turned from school pain into one of her superpowers.
• Hiding that she was gay at work led to shame and a fragmented life.
• Emotional optimism: feelings as data for hard DEI + culture conversations.
• The weight of “impossible” topics (racism, Oct 7) as a white Jewish leader.
• Macro: remove shame, add tenderness; let people be “normally messy” at work.
• Goal isn’t “I love myself” overnight—just helping people get to “I like myself.”
Timestamps
00:00 Intro
01:20 “Who are you in this season?” — back nine, joyful service, goofball
02:10 Taurus energy, love of human behavior, and being Chief Heart Officer
03:30 Telling Gary V she’d write a book & why Be Yourself at Work exists
05:30 93‑day Outward Bound story & “you better get another song in your head”
09:05 Colorado / Leadville / Denver and mountain metaphors
10:40 Learning differences: dyslexia, dyscalculia, school pain → superpower
12:20 Abandoning herself by hiding she was gay at work; shame and a double life
18:01 Brutal DEI day: emotional optimism, accountability, and a hard convo.
24:50 The weight of “impossible” topics as a white Jewish leader
32:52 Macro vision: Helping people get to “I like myself.”
37:48 Where to find Claude
Links
Learn more about Claude Silver
Learn more about Jolie Shapiro
Learn more about Revenue Mind
More
From a 93‑day Outward Bound in the Colorado Rockies to hiding her sexuality at work and now holding impossible DEI conversations as Chief Heart Officer at VaynerX, Claude Silver shares why being yourself at work is both risky and necessary: change the song in your head, remove shame, add tenderness, and stop asking humans to act like machines. Key Takeaways • Back‑nine season: joyful service, big heart, total goofball. • Wilderness wake‑up: 93‑day Outward Bound → “get another song in your head.” • Dyslexia turned from school pain into one of her superpowers. • Hiding that she was gay at work led to shame and a fragmented life. • Emotional optimism: feelings as data for hard DEI + culture conversations. • The weight of “impossible” topics (racism, Oct 7) as a white Jewish leader. • Macro: remove shame, add tenderness; let people be “normally messy” at work. • Goal isn’t “I love myself” overnight—just helping people get to “I like myself.” Timestamps 00:00 Intro 01:20 “Who are you in this season?” — back nine, joyful service, goofball 02:10 Taurus energy, love of human behavior, and being Chief Heart Officer 03:30 Telling Gary V she’d write a book & why Be Yourself at Work exists 05:30 93‑day Outward Bound story & “you better get another song in your head” 09:05 Colorado / Leadville / Denver and mountain metaphors 10:40 Learning differences: dyslexia, dyscalculia, school pain → superpower 12:20 Abandoning herself by hiding she was gay at work; shame and a double life 18:01 Brutal DEI day: emotional optimism, accountability, and a hard convo. 24:50 The weight of “impossible” topics as a white Jewish leader 32:52 Macro vision: Helping people get to “I like myself.” 37:48 Where to find Claude Links Learn more about Claude Silver Learn more about Jolie Shapiro Learn more about Revenue Mind