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The Conversation With My Team I Still Regret
The tension every leader faces: projecting confidence while managing the inner storm.
Sep 24
•
Andrew Capland
6
Leadership Lessons from a VP of Product: How Getting Shushed in a C-Suite Meeting Redefined My Career
For Heidi Gibson (ex-GoDaddy, Typeform, Bill.com), it became a turning point that reshaped her leadership style, confidence, and career trajectory
Sep 17
•
Andrew Capland
The Unintentional Wiring of Startup Life: Your Worth = Your Productivity
Devin Reed (ex-Gong, Clari) built the perfect solo business on paper. A year in, he realized productivity wasn’t enough - and rewired how he measures…
Sep 10
•
Andrew Capland
2
August 2025
"I Had Imposter Syndrome Every 18 Months" – How Amplitude’s Former CPO Survived
He watched his peers get replaced. Each 18-month cycle brought new expectations, and new doubts. Here’s how he learned to survive when imposter syndrome…
Aug 28
•
Andrew Capland
The Hidden Habit That Makes You a Stronger Product Leader
(from a Head of Product Growth)
Aug 21
•
Andrew Capland
1
“Your Peer Said They’d Quit If We Promoted You” - How This VP of Growth Turned It Around
She thought the CMO promotion was locked in. Instead, a single comment from a colleague blew it up - and forced her to face blind spots she didn’t know…
Aug 13
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Andrew Capland
1
July 2025
Why VC-Backed Startups Are So Draining: The Toll on Families
I’ve worked inside 3 VC-backed companies. But, I’d never really heard the founder POV.
Jul 30
•
Andrew Capland
1
This Founder Had Weeks of Runway Left—Then Took a Risk That Saved the Company
Inside a founder’s last-ditch bet, and the conversation that saved it all.
Jul 23
•
Andrew Capland
1
“They said I was too nice.” - How this VP of Growth rewrote the rules of leadership
For tech leaders, is being nice a feature, or a bug?
Jul 17
•
Andrew Capland
2
What If the Feedback Isn’t About You at All?
The feedback wasn’t just unhelpful... it made her question who she was. Here’s what this marketing leader did next.
Jul 2
•
Andrew Capland
3
June 2025
“Are You Phasing Me Out?” - How This Marketing VP Responded in the Moment
What to do when a direct report asks the question you’re not ready to answer.
Jun 25
•
Andrew Capland
2
How to stop hustle culture from becoming your identity
She worked 80-hour weeks, slept in the office, and knew every answer - until her brain shut down and she walked out for good.
Jun 18
•
Andrew Capland
1
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