29. Your Next Bold Move: Business, Bravery, and the Power of Chess
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If you're ready to stop second-guessing yourself and start making bold moves with clarity, this episode will shift your mindset and your strategy.
In this energizing and deeply insightful conversation, Hailey Krajewski is joined by Ashley Lynn Priore—a nationally recognized chess innovator, civic disruptor, and founder of both Queen's Gambit and Queenside Ventures. Together, they unpack what it truly means to lead boldly, especially as a woman in spaces where you're often the only one like you in the room.
Ashley shares how her unconventional path from teaching chess at age eight to building a nonprofit and consulting firm has given her a rare lens on leadership, confidence, and strategy. Her secret? Treating life like a chessboard.
How Chess Became the Blueprint
Ashley dives into her origin story, revealing how a game traditionally dominated by white men became her tool for revolution. Through her experiences in competitive chess, teaching at her local library, and witnessing gendered assumptions firsthand, she found her mission: create inclusive spaces and use chess as a catalyst for critical thinking and leadership.
Why Strategy Starts With Inventory
Forget vague advice. Ashley lays out a clear, actionable way to define strategy: it's about taking stock of your current "chessboard" — your skills, limitations, opportunities, and pieces already in play. Before making your next move, she says, you have to know where you really stand.
Scaling Without Starting Over
In a world that glorifies constant pivoting and "what's next," Ashley challenges us to instead focus on what's already working. She shares how refining an existing offer or deepening current work often leads to greater impact than chasing the next shiny thing.
Claiming Your Seat at the Table (Even If It Wasn't Built for You)
Ashley talks candidly about navigating male-dominated spaces and overcoming "youthism" — a term for underestimating young people. Her insight? Confidence comes from knowing your value and refusing to shrink, even when others doubt you.
What You'll Learn in This Episode:
(00:15:47) How Ashley turned her childhood love of chess into a global movement
(00:26:25) A powerful definition of strategy that starts with self-awareness
(00:29:53) The surprising downside of constant rebranding or pivoting
(00:37:12) What "youthism" is — and how Ashley built credibility at a young age
(00:43:27) A daily mindset practice to build confidence by celebrating wins
(00:49:18) The difference between Queen's Gambit and Queenside Ventures (and how to work with Ashley)
Meet Ashley Lynn Priore
Ashley is a nationally recognized chess champion, entrepreneur, speaker, and civic disruptor. As the founder of Queen's Gambit, she empowers youth through strategic thinking and chess education. Through Queenside Ventures, Ashley advises CEOs, athletes, and mission-driven brands on how to lead with clarity, make bold moves, and build strategy rooted in purpose.
Final Thoughts
Your life is a chessboard. You don’t need more pieces—you need a clearer view of how they move. This episode will remind you that you already have what you need to make your next move with confidence, vision, and purpose.
