The Hidden Cost of Leadership: Why Doing the Right Thing Still Hurts

Mahesh Guruswamy — Chief Product and Technology Officer at Kickstarter and author of How to Deliver Bad News and Get Away with It — sits down with Kwame Christian to reveal the emotional side of leadership no one talks about. Buy the Book: How to Deliver Bad News and Get Away with It: A Manager's Guide by Mahesh Guruswamy⁠ From earning $40,000 in his first tech job to leading global teams, Mahesh learned that success isn’t about titles or wealth — it’s about courage, gratitude, and making the right call even when it hurts. In this powerful conversation, you’ll learn: Why the hardest decisions are often the right ones How to “roll the dice” and take bold career risks The secret to staying grounded in gratitude and perspective Why authenticity—not ambition—is the real mark of leadership If you’ve ever wondered why success can still feel empty, or why doing the right thing sometimes hurts the most — this episode will give you the clarity you’ve been looking for. Buy the Book: How to Deliver Bad News and Get Away with It: A Manager's Guide by Mahesh Guruswamy