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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