The Game Is Rigged. Here’s How You Win Anyway (High Agency + Start Before You’re Ready) | Investor Kofi Ampadu episode artwork

EPISODE · Jun 8, 2026 · 1H 15M

The Game Is Rigged. Here’s How You Win Anyway (High Agency + Start Before You’re Ready) | Investor Kofi Ampadu

from Tiger Sisters · host Cherie Brooke Luo and Jean Luo

Sign up for our newsletter here: https://cherieluo.substack.com/subscribeWelcome to the very first installment in our new series called Tiger Sisters: Director’s Cuts. In these episodes, we revisit some of our favorite conversations from the past. Today, we’re digging back into our incredible episode with investor and 2x-founder, Kofi Ampadu. From navigating systems that weren’t built for you to betting on yourself before you feel "ready," Kofi shares the frameworks that shaped his career. He also reflects on how he's now living a version of the life he envisioned more than a decade ago. Tune in for lessons and new reflections on: ✅How to succeed when the rules of the game aren't designed for you✅Why high-agency people focus on what they can control✅The importance of writing down your goals (and sharing them with someone else!)✅ Why waiting for the "perfect time" can quietly derail your dreams✅ How Kofi evaluates whether he's having a good year, month, week, and day✅ What founders, investors, and ambitious people can learn from long-term thinkingThis episode is packed with frameworks and new reflections that you’ll want to apply TODAY! Follow Kofi: @kofiampaduTimestamps:01:06: Introducing the Director’s Cut Series 01:58: How to watch this episode 04:43: Introducing Kofi to the audience 05:32: How Kofi learned to navigate rooms where he was different 07:55: The importance of highlighting wins for founders of color09:31: A framework for making “the game” more fair for yourself 11:31: Inside Kofi’s journaling habit and takeaways 13:33: Making a life plan (and sharing it with a friend!)15:01: Kofi’s early side-hustles (hello DoorDash?!)21:53: How to be the captain of your own ship22:58: Kofi’s early founder days living with his sister30:18: Kofi and his wife’s “brown bag” research lunches 34:26: 3 Ways Kofi determines if he “won his day” 43:28: How failure is actually healthy47:30: Red Flags in investing 52:15: True or False questions 55:44: Cherie’s biggest takeaways from the episode 57:35: Jean’s reflections on “the rules of the game” being rigged1:01:22: Cherie and Jean reflect on the fear of failure1:02:17: Why more companies should be funding women1:05:55: Cherie’s reflections on Kofi’s family stories 1:10:07: Jean’s reflections on Kofi’s tracking systems 1:14:17: Closing thoughts 🐯👯‍♀️ 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] 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 youWhat 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.brookeTikTok — /cherie.brookeSubstack — cherieluo.substack.comLinkedIn — /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

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The Game Is Rigged. Here’s How You Win Anyway (High Agency + Start Before You’re Ready) | Investor Kofi Ampadu

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