--- title: "How Creativity Fuels Better Financial Leadership with Andrew Evans" description: "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…" url: https://www.milemarker.co/podcast/how-creativity-fuels-better-financial-leadership-with-andrew-evans updated: 2026-02-17 --- [Now playing](https://www.milemarker.co/podcast) [Podcast**Next Mile**](https://www.milemarker.co/podcast) [Episodes](https://www.milemarker.co/podcast)[Guests](https://www.milemarker.co/podcast/guests) [YouTube](https://www.youtube.com/@milemarkerinc) [Apple](https://podcasts.apple.com/us/podcast/the-connected-advisor/id1691759257) [Spotify](https://open.spotify.com/show/0Lw8kHGnS1JJBMZLPYxc9S) Episode 132 · Feb 17, 2026 · 47 min # How Creativity Fuels Better Financial Leadership with Andrew Evans [**Andrew J. Evans***CEO/CCO, Rossby*](https://www.milemarker.co/podcast/guests/andrew-evans) [Apple Podcasts ↗](https://podcasts.apple.com/us/podcast/the-connected-advisor/id1691759257) [Spotify ↗](https://open.spotify.com/show/0Lw8kHGnS1JJBMZLPYxc9S) ## About this episode 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 - (32:22) - Creativity, patience, and building differently - (35:16) - Andrew's outlook on the future of the financial services industry - (44:13) - Andrew's Milemarket Minute **Key Takeaways** - Whether you're selling a mortgage or a financial plan, technical skills are just the baseline. The real growth comes from mastering interpersonal and psychological engagement and understanding the emotional drivers behind a client's financial decisions. - Plan a repeatable process. Growth becomes sustainable when your marketing and operations are simple enough to execute consistently every day. - Design for less but better. Complexity is the enemy of efficiency. In leadership and tech, aim for intuitive design that reduces clicks and surprises. Your goal should be to create a "source of truth" for data that lets your team spend less time on administration and more time on high-value work. - The best ideas at any conference or meeting rarely come from the person at the podium. They happen in the hallways, over coffee, or during shared activities. **Quotes** "Nobody gains great ideas by sitting there and being lectured at. It doesn't happen. The best stuff happens in the conversations on the edges." ~ Andrew Evans "You can't satisfy everyone. Whatever you've decided on for your firm's tech stack, someone is going to hate it. So, design for the firm's data integrity first, then let them pick their tools." ~ Andrew Evans "Focus on where your practice's source of truth is. That's where you really need your agent. Keep it focused. Keep it tight." ~ Andrew Evans **Links** - [Andrew Evans on LinkedIn](https://www.linkedin.com/in/andrewjevans/) - [Rossby Financial](https://rossbyfinancial.com/) - [Raymond James](https://www.raymondjames.com/) - [The Unconference](https://www.theunconference.live/2026) - [Kelsey McKenna](https://www.linkedin.com/in/kelseymckenna3/) - [Seeds Investor](https://useseeds.com/) - [Midquel McClendon](https://www.linkedin.com/in/midquel-mick-mcclendon-0b4851/) - [Capital Square](https://capitalsq.com/) - [The Design of Everyday Things](https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654) - [Redtail Technology](https://redtailtechnology.com/) - [Wealthbox](https://www.wealthbox.com/) - [Advisor360](https://www.advisor360.com/) - [eMoney Advisor](https://emoneyadvisor.com/) - [The Lord Of The Rings](https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411) **Connect with our hosts** - [Milemarker.co](https://www.milemarker.co/) - [Kyle on LinkedIn](https://www.linkedin.com/in/kylevanpelt/) - [Jud on LinkedIn](https://www.linkedin.com/in/judmackrill/) **Subscribe and stay in touch** - [Apple Podcasts](https://podcasts.apple.com/us/podcast/connected/id1691759257) - [Spotify](https://open.spotify.com/show/0Lw8kHGnS1JJBMZLPYxc9S) - [YouTube](https://www.youtube.com/@milemarkerinc) **Produce game-changing content with Turncast** Turncast helps your company grow by producing top-quality content and fostering transformative conversations. We specialize in content generation, podcasting, digital strategy, and audience growth for fintech and financial services companies. Learn more at [Turncast.com](https://www.turncast.com/). ## The write-up [Listen to this week’s episode](https://open.spotify.com/episode/5ElggAJ2YwsxOB2dvWTjtR) ## Episode 132 On this week’s episode of Next Mile, I sit down with [Andrew Evans](https://www.linkedin.com/in/andrewjevans/), Chief Executive Officer of [Rossby](https://rossbyfinancial.com/). Before Rossby, Andrew served as Executive Vice President at TAG Advisors and as a Securities Principal at Cambridge Investment Research. Andrew discusses entrepreneurship, growth, and designing better businesses. With a background in musical theater and a career spanning mortgage brokerage and financial advising, he 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. #### **Key Takeaways** - Whether you’re selling a mortgage or a financial plan, technical skills are just the baseline. The real growth comes from mastering interpersonal and psychological engagement and understanding the emotional drivers behind a client’s financial decisions. - Plan a repeatable process. Growth becomes sustainable when your marketing and operations are simple enough to execute consistently every day. - Design for less but better. Complexity is the enemy of efficiency. In leadership and tech, aim for intuitive design that reduces clicks and surprises. Your goal should be to create a “source of truth” for data that lets your team spend less time on administration and more time on high-value work. - The best ideas at any conference or meeting rarely come from the person at the podium. They happen in the hallways, over coffee, or during shared activities. #### **Quotes** “Nobody gains great ideas by sitting there and being lectured at. It doesn’t happen. The best stuff happens in the conversations on the edges.” ~ [Andrew Evans](https://www.linkedin.com/in/andrewjevans/) “You can’t satisfy everyone. Whatever you’ve decided on for your firm’s tech stack, someone is going to hate it. So, design for the firm’s data integrity first, then let them pick their tools.” ~ [Andrew Evans](https://www.linkedin.com/in/andrewjevans/) “Focus on where your practice’s source of truth is. That’s where you really need your agent. Keep it focused. Keep it tight.” ~ [Andrew Evans](https://www.linkedin.com/in/andrewjevans/) #### **Links** - [Andrew Evans on LinkedIn](https://www.linkedin.com/in/andrewjevans/) - [Rossby Financial](https://rossbyfinancial.com/) - [Raymond James](https://www.raymondjames.com/) - [The Unconference](https://www.theunconference.live/2026) - [Kelsey McKenna](https://www.linkedin.com/in/kelseymckenna3/) - [Seeds Investor](https://useseeds.com/) - [Midquel McClendon](https://www.linkedin.com/in/midquel-mick-mcclendon-0b4851/) - [Capital Square](https://capitalsq.com/) - [The Design of Everyday Things](https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654) - [Redtail Technology](https://redtailtechnology.com/) - [Wealthbox](https://www.wealthbox.com/) - [Advisor360](https://www.advisor360.com/) - [eMoney Advisor](https://emoneyadvisor.com/) - [The Lord Of The Rings](https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411) #### **Connect with our hosts** - [Milemarker.co](https://www.milemarker.co/) - [Kyle on LinkedIn](https://www.linkedin.com/in/kylevanpelt/) - [Jud on LinkedIn](https://www.linkedin.com/in/judmackrill/) #### **Subscribe and stay in touch** - [Apple Podcasts](https://podcasts.apple.com/us/podcast/connected/id1691759257) - [Spotify](https://open.spotify.com/show/0Lw8kHGnS1JJBMZLPYxc9S) - [YouTube](https://youtu.be/lUiv6FsEreg) **While there, please don’t forget to Download, Like, and Subscribe.** If you’d like to schedule a time to talk with me about anything we cover on our podcast or [Milemarker](https://www.milemarker.co/), [click here for 15 minutes](https://meetings.hubspot.com/kyle-van-pelt). Kyle Van Pelt [**Andrew J. Evans***CEO/CCO, Rossby*](https://www.milemarker.co/podcast/guests/andrew-evans) Next Mile Conversations with the people building the next era of wealth management, hosted by Kyle Van Pelt. New episodes every Tuesday. [Get the newsletter →](https://www.milemarker.co/resources/newsletter) [Talk to Milemarker →](https://www.milemarker.co/contact) ## Keep listening Ep. 170 · Nov 10, 2026 · 27 min ### [Building a Boutique at Scale with Leah Sciabarrasi](https://www.milemarker.co/podcast/building-a-boutique-at-scale-with-leah-sciabarrasi) Leah Sciabarrasi, Crestwood Advisors Ep. 157 · Aug 11, 2026 · 27 min ### [The Power of Radical Hospitality in Financial Advice with Libby Buckley](https://www.milemarker.co/podcast/the-power-of-radical-hospitality-in-financial-advice-with-libby-buckley) Libby Buckley, Parable Wealth Partners Ep. 155 · Jul 28, 2026 · 32 min ### [How Behavioral Data Creates Better Client Relationships with Julie Littlechild](https://www.milemarker.co/podcast/how-behavioral-data-creates-better-client-relationships-with-julie-littlechild) Julie Littlechild, Absolute Engagement