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What’s the Best That Could Happen? Madison Phipps on Building an Art Business in the Margins

Apr 1, 2026

Margo is joined by artist and illustrator Madison Phipps, the creative force behind Madison Phipps Studio. Known for her feminine, timeless botanical artwork rooted in nostalgia and storytelling, Madison shares how she’s built a growing art business while balancing motherhood and a full-time job. From painting in the quiet margins of her day to landing dream collaborations and launching collections, this conversation is a refreshing and honest look at what it really takes to pursue creativity in the “messy middle.”

Margo and Madison explore the mindset shifts, practical strategies, and courageous decisions that helped her turn a personal creative practice into a thriving business, without waiting until everything felt “ready.”

Margo and Madison discuss:

  • Using the question “what’s the best that could happen?” as a roadmap for growth and decision-making
  • How sharing her journey on TikTok helped her grow a community and gain visibility
  • Pitching yourself before you feel ready—and how cold outreach led to major opportunities
  • The inspiration behind her nostalgic, botanical artwork rooted in childhood memories
  • Launching and sustaining a snail mail print club as a recurring revenue stream
  • Lessons from collaborations, including her botanical collection with Paloma & Co
  • Balancing ambition, creativity, and family life without burning out

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