“Just Ask” Is the #1 Career Skill (Pay, Promotions, Power)

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 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 🐯👯‍♀️ We’re the Tiger Sisters — your Wall Street & Silicon Valley big sisters Decoding Money • Power • Love ✨ New episodes every Monday | Shorts all week ✨ 💌 Want to partner with us? Sponsorships: [email protected] Why trust us? ▫️ Cherie Brooke Luo — 100M+ views demystifying tech, finance & MBAs ▫️ Jean Luo — ex-Goldman Sachs, ex-Snapchat exec, 50+ AI patents, startup investor ▫️ Together: 4 Ivy League degrees • built billion-dollar products • two startups — decoded for you What you’ll get (and keep): ▫️ 🚀 Ivy League cheat sheets — no $250K tuition ▫️ Personal finance playbooks (salary, investing, negotiation) ▫️ Networking scripts behind $100M+ deals & job offers ▫️ Real conversations with CEOs, operators & investors ▫️ Mindset resets — clarity without the pricey coach ▫️ Systems for career, money, and long-term growth 💛 LET’S CONNECT ~ CHERIE ~ Instagram — /cherie.brooke TikTok — /cherie.brooke Substack — cherieluo.substack.com LinkedIn — /cherie-luo ~ JEAN ~ Instagram — /jeanluo_ LinkedIn — /jeanluo 👉 Hit Subscribe & tap the 🔔, then leave a ⭐️⭐️⭐️⭐️⭐️ review on Spotify & Apple Podcasts. It takes 10 seconds and makes a massive difference in helping new people discover Tiger Sisters. 🛍️ Items: 🍵 Sisters Matcha — www.sistersmatcha.com 🌀 Everything else — https://amzn.to/3z0dx5b