How Creativity Fuels Better Financial Leadership with Andrew Evans

How Creativity Fuels Better Financial Leadership with Andrew Evans

From Next Mile by Milemarker

February 17, 2026 · 47 min

About this episode

Andrew Evans discusses the intersection of creativity and financial leadership, sharing insights from his diverse career.

Episode 132: This week, Kyle Van Pelt talks with Andrew Evans, Chief Executive Officer of Rossby. Before Rossby, Andrew served as Executive Vice President at TAG Advisors and as a Securities Principal at Cambridge Investment Research. Andrew talks with Kyle about entrepreneurship, growth, and designing better businesses. With a background in musical theater and a career that spans mortgage brokerage and financial advising, Andrew shares the parallels between creative careers and financial services, why repeatable processes beat flashy marketing plans, and how thoughtful design can transform the advisor experience. In this episode: (00:00) - Intro (01:39) - Andrew's money moment (04:55) - Parallels between mortgage brokerage and financial advising (07:07) - How Andrew built his early book of business (11:50) - The financial-planning version of a closing credit (13:07) - Redefining traditional conferences with The Unconference (16:41) - How The Unconference generates the best business ideas (19:43) - What it means to drive business forward (25:04) - The concept of "less but better" in business and technology (28:39) - Designing intuitive systems and reducing operational friction…

People in this episode

Host: Kyle Van Pelt

Guest: Andrew Evans

Topics covered

  • financial leadership
  • creativity
  • entrepreneurship
  • business design
  • financial services

Keywords

  • financial leadership
  • creativity
  • business design
  • entrepreneurship
  • financial services
  • mortgage brokerage
  • advisor experience

Mentioned in this episode

Organizations: Rossby, TAG Advisors, Cambridge Investment Research

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