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Negotiate Anything

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

Negotiate Anything

American Negotiation Institute

Education, Business, Self-improvement

4.7748 Ratings

🗓️ 23 October 2025

⏱️ 45 minutes

🧾️ Download transcript

Summary

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

Transcript

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0:00.0

Today's guest is Mahesh Guruswami, the chief product and technology officer at Kickstarter,

0:05.0

and the author of a powerful new book called How to Deliver Bad News and Get Away with it,

0:10.3

a manager's guide. And this is a no-nonsense exploration of leadership, authenticity, and mastering

0:16.2

tough conversations. Mahesh's story is the definition of courage and perspective. He went from earning

0:22.2

$40,000 a year in his first tech job to leading teams at one of the biggest companies in the world.

0:28.5

And along the way, he learned that real success isn't just about climbing higher. It's about

0:33.3

gratitude, clarity, and making bold choices when fear tells you to play it safe.

0:39.3

In this episode, we talk about the mindset that drives great leaders, the immigrant experience

0:43.6

that shaped him and his brilliant one-way door versus two-way door framework, a simple but

0:49.0

game-changing way to make better decisions in life and business.

0:53.6

This conversation will remind you that growth

0:55.9

doesn't always come from moving faster. Sometimes it comes from stepping back, taking a breath,

1:01.5

and rolling the dice on what truly matters. Let's jump in. So I'm like 40-some years old,

1:10.4

and I came here as an immigrant.

1:14.6

And, you know, for the last 20-some years, I've been in tech.

1:20.2

And, you know, like in the day-to-day workings of what you go through, you have all these problems, right?

1:28.6

It's like, this project is delayed. This conversation was not great. You know, this thing is like painful. But today I like

1:36.1

went out for a run and I came back and I told myself, I'm like way too blessed to be able to do

1:42.7

what I have to do, what I I can do be able to like live the

1:46.2

life that I can live and I think it's just like people should be more grateful for what they what they have

1:53.2

and it's obviously there's a lot of like hard work like bloods and sweat and tears like associated with it

1:59.0

which which I'm on a discount because we did work really hard to get to where we are. But, you know, just the fact that

...

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