All Episodes

July 24, 2025 55 mins

What if the very traits you've been taught to hide—like being selfish, nosy, or even manipulative—are actually your greatest unfair advantage?

That’s the bold idea Jenny Wood explores in Wild Courage—a framework she developed after nearly two decades at Google, where she rose through the ranks, led billion-dollar business units, and launched initiatives that reached over 50,000 employees across 100+ countries.

Eventually, success on paper wasn’t enough. Jenny felt burned out and boxed in—stuck between achievement and alignment. That turning point led her to redefine what real courage looks like in business and life.

In this episode, she unpacks the 9 traits society often labels as “too much” or “too aggressive”—and shows how to reclaim them as strategic tools for influence, opportunity, and a life you actually want. Whether you’re looking to land the promotion, launch your business, or stop playing small, this conversation will challenge everything you thought you knew about confidence, leadership, and courage.


In this episode, you’ll learn: 


1.) The wild subway story that changed Jenny’s life—and the mindset shift that helped her take bold action in the face of fear.

2.) Discover the 9 unconventional traits that define Wild Courage—and how they unlock greater influence, freedom, and business growth.

3.) Why “manipulative” might be your most powerful leadership trait—and how to use it to build trust, influence, and high-leverage relationships.

4.) Why replacing your salary may be the wrong goal—and how to build confidence, earn through passive income, and design a life that truly aligns with what matters most.


Show Notes: LifestyleInvestor.com/248


Tax Strategy Masterclass

If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax


Strategy Session 

For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation


The Lifestyle Investor Insider

Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider


Rate & Review

If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple PodcastsSpotifyor wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.


Connect with Justin Donald



See Privacy Policy at


Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Special Summer Offer: Exclusively on Apple Podcasts, try our Dateline Premium subscription completely free for one month! With Dateline Premium, you get every episode ad-free plus exclusive bonus content.

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.