The Outstanding Shift

The Outstanding Shift

Welcome to The Outstanding Shift with Andrew Evans from Rossby Financial. In this podcast, we help financial professionals cut through the noise, ditch outdated thinking, and rediscover the joy in their work. Join us as we explore bold new perspectives on the financial world, blending humor, clarity, and actionable insights. With Andrew’s years of expertise and special guest experts, we’ll uncover hidden treasures in the economic ecosystem, solve challenges, and make the Shift.

Episodes

October 20, 2026 • 35 mins

Operational drag can quietly steal hours from an advisor’s day. What changes when investment management becomes more repeatable, less manual, and easier for the team to run?

In this episode, Andrew Evans welcomes back Zachary Conway and Kelsey McKenna from Seeds to discuss how advisors can reduce time spent on trading, model setup, cash requests, tax-loss ...

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AI is changing how financial professionals work, but faster tools also raise new questions. 

How can advisors use AI while keeping judgment, review, and client care at the center?

In this episode, Andrew Evans and Lindsay Evans welcome Jesse Rosato, Chief Technology Officer at Nitrogen, for a conversation about AI, adv...

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AI is changing how advisors manage client notes, workflows, and follow-up. 

But when does helpful automation become a better way to run the whole client relationship?

In this episode, Andrew Evans talks with Thomas Clawson, CEO of Slant, about why advisor CRM systems are being rebuilt around AI. Thomas shares how Slant...

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What does independence actually look like for a financial advisor today? For many advisors, the answer is more complicated than simply “starting your own RIA.”

In this episode, Andrew Evans takes a look at what it really means to build an independent advisory business, and why many advisors are rethinking the traditional path. Instead of focusing so ...

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Most financial advisors think they need better marketing. What they may actually need is better storytelling.

In this episode, Andrew Evans sits down with Alexandra Zendrian, founder of A to Z Communications, to talk about the real difference between marketing and public relations, and why so many advisors misunderstand both. Allie shares how she accidentally be...

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Online reviews can shape whether a prospect reaches out or keeps scrolling. But for financial advisors, testimonials come with compliance concerns, disclosure requirements, and questions about where reviews should live.

In this episode, Andrew Evans speaks with Brian Thorp, Founder and CEO of Wealthtender and Editor-in-Chief, about how advisors can use client te...

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Most people leave conferences with a stack of business cards, a drained social battery, and no real follow-up plan.

In this episode of The Outstanding Shift, Andrew Evans sits down with Marie Loudin and Lori Zinaich to discuss what actually makes conferences worth the investment, especially for advisors, marketers, and business development professionals seeking ...

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Great financial advice is not just about what you recommend. It’s about how clients experience every step along the way.

What if the biggest gap in financial advice is not knowledge, but how that knowledge is delivered, explained, and felt by the client?

In this episode, Andrew Evans continues his conversation with Za...

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Most people don’t struggle because they lack information; they struggle because they can’t clearly see what they already have.

What if the real issue isn’t strategy, but how it’s communicated and understood?

In this episode, Andrew Evans interviews H. Adam Holt, CEO & Founder of Asset-Map, about ...

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Creating content can feel overwhelming, especially when time and skills don’t seem to align.

What actually works when it comes to video, and how can professionals stay relevant without burning out?

In this episode, Andrew Evans interviews Laura Garfield, Co-Founder of Idea Decanter, about why many advisors struggle wi...

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Advisors are working harder than ever, yet many still feel stuck delivering inconsistent client experiences. What if the issue is not effort, but how services, operations, and investment management are structured in the first place? In this episode, Andrew Evans speaks with Zach Conway, Founder and CEO of Seeds, and Kelsey McKenna, COO of Seeds, …

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Most business owners think launching a website is enough to start generating leads. But what happens after someone clicks? In this episode, Andrew Evans sits down with Cassia Watts, Co-Founder of HiveOne.io and Co-Creator of AnchorPoint, to unpack why most entrepreneurs struggle with marketing systems. They explore the limits of DIY website builders, the importance …

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Career paths rarely follow a straight line and sometimes the best opportunities come from unexpected places. What happens when you find yourself in a role that doesn’t align with your values? How do you discover work that truly matters? In this episode, Andrew Evans interviews Leslie Lipscomb, Senior Vice President at Financial Independence Group, about …

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Insurance often feels like an afterthought until something goes wrong. Are you confident your coverage actually protects you when it matters most? In this episode, Rossby Financial’s Founder Andrew Evans chats with Chad Ramberg, Founder & President of Box Professional Insurance, about errors and omissions insurance for financial advisors. Chad shares his journey from claims …

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Technology is advancing at lightning speed, leaving many professionals wondering how to adapt and thrive. In this episode, Andrew Evans is joined by his brother David Evans and producer RJ Malyk for a candid discussion on AI, resilience, and finding new ways to stay relevant in rapidly changing industries. RJ shares how his background in …

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Business development is often about numbers, but at its core, it’s about relationships, transparency, and growth. In this episode, Andrew Evans talks with Pamela Mule, VP of Business Development at J.W. Cole about her journey from compliance to leading recruiting and development. Pamela shares how she builds trust with advisors, the role of technology in …

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Representation in financial services isn’t just about numbers. It’s about visibility, mentorship, and meaningful change. In this episode, Andrew Evans talks with Melissa Reaktenwalt, MBA, CSRIC™, AIF®, Founder and CEO of EViE Financial Group, about her mission to bring more diversity and authenticity into the advisory space. Melissa shares how intentional visibility, openness to new …

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The WealthTech space is bursting with options, but more choices don’t always mean better solutions. Why are so many firms building one-off tools without considering the full advisor experience? And how can entrepreneurs design, grow, and even sell companies in this crowded market? In this episode of The Outstanding Shift, Andrew Evans talks with Larry …

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What does artificial intelligence really mean for industries like finance, and why do so many get it wrong? In this episode of The Outstanding Shift, Andrew Evans sits down with his brother, David Evans, Senior Machine Learning Model Developer at Duolingo, who had previous stints at Google and other major tech companies. Together, they dig …

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What happens when you ask Gen Z why the financial advisory industry “sucks?”You get the truth, and it’s exactly what the industry needs to hear. How do younger professionals really view financial advisors? What are they craving in a workplace, and where is the industry falling short? In this episode, Andrew Evans is joined by …

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