The Learning Leader Show With Ryan Hawk

266: Ryan Caldbeck - CircleUp CEO: How To Build The Frameworks Of Your Life & Career

Jul 15, 2018
Ryan Caldbeck, founder and CEO of CircleUp and builder of Helio, shares his framework-driven approach to leadership and hiring. He discusses sustaining excellence through persistence, passion, drive, and values. Hear stories about finding purpose, building teams, codifying culture traits like horsepower and integrity, and transitioning from individual contributor to manager.
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INSIGHT

Four Traits That Sustain Excellence

  • Sustained excellence relies on persistence, a focused passion, a motor (drive), and clear values.
  • Ryan Caldbeck links passion to irrational persistence and values to a decision-making framework that prevents short-term derailment.
ANECDOTE

How A Missed Question Led To Founding CircleUp

  • Ryan Caldbeck recounted ignoring a college coach's advice to pursue passion and instead followed expected career steps into consulting and private equity.
  • After a decade he used a multi-month 'five whys' exercise with his then-girlfriend to discover his passion: helping others thrive, which led to CircleUp.
ADVICE

Write Hiring Frameworks Before You Interview

  • Create explicit frameworks for hiring and operations so teammates can move quickly without micromanagement.
  • Define traits to evaluate, hiring loops, decision owners, and interview counts to avoid ad hoc, inconsistent hiring.
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