What if the most important skill for your career, relationships, and life… is simply learning how to ask? Today, we sit down with former CEO of Match Group, Mandy Ginsberg, to explore what really happens at the intersection of love, data, power, and reinvention. From scaling the business behind Tinder and Match, to serving on nearly 14 boards (and counting) throughout her career, Mandy teaches the art of making high stakes decisions.

We get into:

✅Why “just ask” is one of the most underrated career skills (and why women are less likely to do it)

✅The real impact of asking for raises, promotions, and opportunities, and how it compounds over time

✅How to recognize when it’s time to leave (even at the top) and how to reinvent yourself

✅The mindset shift from operator → board member

✅How top companies think about compensation, incentives, and the psychology of risk

✅The power of community-building as a leadership skill

✅ How to intentionally build relationships that compound across your entire career

Plus, we explore the human side of leadership; from running a company alongside your closest collaborator, to learning that you don’t have to be the star player to build something iconic.

If you’ve ever wondered how to ask for more, when to walk away, or how to navigate power in your career, this episode is your playbook. Because at every level, you don’t get what you deserve… you get what you ask for.

Timestamps:

00:27: Meet Mandy (Match Group CEO)

02:00: The evolution of dating apps

06:54: Knowing when to leave

07:24: Leadership and self-doubt

09:05: From operator to board member

10:14: What makes a great board member?

10:42: Crisis leadership (JCPenney)

11:00: Disrupting your own business

12:24: First board seat (Care.com)

13:58: Staying close to innovation

14:18: Board “superpowers”

16:25: Compensation as psychology

18:02: Equity vs cash decisions

18:43: Most people avoid risk

20:23: Pay transparency origins

20:47: Scaling Match Group

21:16: Women & under-asking

31:17: Power of networks

31:47: Investing in relationships

34:06: Mild & Wild Question Game

38:23: Competition vs self

38:53: Internal drive

39:14: Outro

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