21 Hats Podcast

Hot Seat: Three Owners, No Easy Answers

10 snips
Feb 17, 2026
Ted Wolf, CEO of GuideWise, tech builder turned AI implementer. Jackie Russo, CEO of Brand Russo, agency leader and branding strategist. Kate Morgan, CEO of Boston Human Capital Partners, recruiter and fractional HR pro. They riff on hiring and talent readiness. They swap worst-job stories and resilience lessons. They debate crypto, smart ways to spend $10,000 on marketing, and whether agencies should hire other agencies.
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ADVICE

Hire For Motor, Not Just Resume

  • Hire by assessing life experience, problem-solving, and intellectual curiosity rather than just titles.
  • Push interviews to surface real drive by asking about high school, difficult situations, and concrete actions.
ANECDOTE

Dairy Farm Childhood Lesson

  • Ted worked on a dairy farm as a teen and learned quickly what he didn't want to do long-term.
  • The farmer paid him late but kept his word and used social rituals to build belonging.
ANECDOTE

Painful Early Care Work

  • Kate's worst job was at a state-run assisted living facility where cognitive decline made work emotionally hard.
  • She remembers awkward moments with residents that left a lasting impression.
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