Bad Decisions Podcast

#76 No BS Conversation about AI & ARTISTS with Jess Wiseman

26 snips
Dec 19, 2025
Jess Wiseman, a multidisciplinary artist and creative director, shares her journey through the creative landscape. She discusses overcoming fears and the impact of self-awareness on growth. Jess delves into the importance of consistency and outreach in building a successful career, emphasizing the role of AI in transforming creation. She advocates for embracing imperfection and prioritizing intention over perfection. Through personal anecdotes, she highlights the balance between creative freedom and the constraints that drive innovation, offering invaluable insights for creators.
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ADVICE

Outreach: Make The Yes Easy

  • Do hyper-personalized outreach: find the right person, research them, and make a frictionless, specific ask.
  • Offer over-delivery or an initial free piece to get a foot in the door and convert to paid work.
ANECDOTE

A Painting Sent To Conor McGregor

  • Jess mailed a 100-hour painting to Conor McGregor via his chef and the piece was received but never returned.
  • She persisted and later landed KSI after continuing cold outreach despite setbacks.
INSIGHT

Momentum Beats Constant Zigzags

  • Insight: Choose a momentum mindset over constant mastery zigzags to scale sustainably.
  • Long-term focus plus processes beat repeated short bursts of beginner-to-burnout cycles.
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