Knowing Me, Knowing You
Knowing Me, Knowing You – The Podcast For The Future of Wealth Management
The Knowing Me, Knowing You Podcast is where forward-thinking wealth managers, tech innovators, and engaged clients come together to explore the future of client discovery and engagement to drive growth.
Through candid conversations with industry leaders, behavioral finance experts, and innovators, we uncover new ways to personalize advice, strengthen advisor-client relationships, and drive business growth.
Whether you're an advisor looking to differentiate, a fintech leader shaping the future, or a client who wants more alignment between money and purpose—this podcast is for you.
Better conversations. Smarter decisions. Stronger connections. Subscribe now.
Knowing Me, Knowing You
61. Defining a Range of Good with Natalie Taylor
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In this episode, I sit down with Natalie Taylor, CFP®, nationally recognized financial planner, fintech consultant, and founder of the Goodland Group, to explore what it really means to deliver advice that works in real life and not just on paper. With over 20 years in financial planning and a decade building inside fintechs like Learnvest, SoFi, Monarch Money, and Ellevest, Natalie brings a rare and refreshing perspective on what human-centered planning actually looks like in practice.
We talk about why the "do it with you" model is the underserved middle ground that clients actually want, how defining a range of good decisions replaces the pressure of a single right answer, and why co-creating goals with clients leads to dramatically higher follow-through. Natalie also shares her "choose your regrets" framework for equity compensation decisions, how she uses base hit versus home run goal buckets to establish risk capacity, and why she sees goals not as a fixed destination but as an evolving container.
If you are an advisor looking to move beyond the hundred-page plan and build relationships where clients actually implement the advice, this conversation will shift how you think about discovery, empowerment, and what it means to truly know your client.
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