Fly like an eagle: Soaring from the doom loop to the hope loop

If you’re a founder who’s tired of hearing all the bad news, you’re probably wondering how to snap out of the doom loop and get yourself onto the hope loop.

We pick up our conversation with Khailee Ng, managing partner at 500 Global, for the second part of our special two-part series. He taps into the compounding grief and loss of control that many founders have faced in the downturn. Khailee also offers a blueprint for how founders can heal themselves and stack the odds in their favor.

In this episode, we cover:

• The founder’s inner journey: Why rejection hurts more than we think, and how healing from past experiences is essential for forward momentum.
• Second foundings: What it means to reinvent your business – and yourself – in a world shaped by AI, new geographies, and changing capital dynamics.
• Global mindsets: Why Southeast Asian founders need to look beyond their region for both inspiration and opportunity.
• Stacking the odds: How to ship, iterate, and last long enough to win.

As Khailee puts it, “Hope is not something you find. It’s something you build. And building starts by taking back control – over your story, your strategy, and your future.”

Listen now to part two of this special two-part conversation: YouTube | Spotify | Apple

Timestamps
00:30 – Part 1 recap
02:30 – “I’m not here to motivate you”
04:45 – Why rejection hurts so damn much
07:40 – Fork in the road: fundraise or fire?
12:10 – Your “second founding” starts now
15:00 – Building your own hope loop
17:30 – The geography myth
21:25 – Death by risk aversion
29:10 – The “right to win” starts with three things
35:50 – Don’t be a duck; fly like an eagle

60/40 is a bi-weekly podcast hosted by Prashanth Ranganathan, Peter Bithos, and Maria Li.