Category: Finance
Building a Career with Purpose: Leslie Lipscomb on Women in Financial Services (Ep. 11)

Building a Career with Purpose: Leslie Lipscomb on Women in Financial Services (Ep. 11)

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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 her journey from hating her first insurance job to building a nearly 20-year career she loves. She shares how FIG’s technology platform helps advisors simplify their legacy business, the growth of women in financial services, and the meaningful “why” that drives her work every day. Leslie also discusses the challenges women advisors face and how organizations can better support them.

Leslie discusses:

  • Her path from a $30,000 millionaire at a big box insurance company to senior leadership at FIG
  • How advisors miss opportunities by not connecting their legacy book of business to technology platforms
  • The acceleration of women entering financial services and the confidence gap many still experience
  • The story behind FIG’s founding and the personal legacy that motivates her work after nearly two decades
  • Why women advisors are more likely to build sustainable succession plans than their male counterparts
  • And more!

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About our Guest: 

Leslie Lipscomb joined Financial Independence Group in 2006 as a Sales Consultant in the annuity division. During her 10 years as a consultant, Leslie was recognized as one of the most successful insurance Sales Consultants in the country.

In 2017, Leslie was promoted to Senior Vice President and currently leads a private client group that supports independent financial professionals across the country. Her private client group focuses heavily on comprehensive and holistic planning using life insurance, annuity and long term care products. In an ever-changing industry, Leslie plays a vital role in helping her agents build a business and marketing plan unique to each individual practice. Once a plan has been developed, Leslie and her team take a hands-on approach to ensure the plan is fully implemented.

Working for a family owned and operated company, Leslie prides herself on the fact that Financial Independence Group is truly an independent marketing organization which allows her to offer her agents and their clients an unbiased opinion when recommending insurance products. Leslie strives to work with her agents daily to assist them in fulfilling their client’s specific retirement or legacy needs. Leslie currently holds her Life and Health license as well as Medicare Supplement and Long Term Care license.

Leslie grew up in Charlotte, NC and graduated from Methodist University in 2005 with a Bachelor of Science in Business and Marketing. When she isn’t working with her agents, you can find her paddle boarding or boating on Lake Norman and spending time with her family. Leslie and her husband David reside in Cornelius, NC with their two dogs Jackson and Savannah.

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Understanding E&O Insurance: What Financial Advisors Need to Know with Chad Ramberg (Ep. 10)

Understanding E&O Insurance: What Financial Advisors Need to Know with Chad Ramberg (Ep. 10)

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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 adjuster to financial advisor to insurance specialist, explaining why most advisors misunderstand their coverage. He breaks down the lifecycle of claims, the importance of early intervention, and how group plans may leave advisors exposed.

Chad discusses:

  • Why his 20 years on the claims side revealed the problems with generic insurance coverage approaches
  • How claims volume correlates with market downturns and why severity matters more than frequency
  • The importance of calling for help before complaints escalate into formal claims
  • Why default deductibles and aggregate limits may not align with your actual risk exposure
  • How some firms collect more in premiums from advisors than their total coverage provides
  • And more!

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About Our Guest: 

Chad Ramberg has over 25+ years of experience in management, including GM/Director and Controller positions.

For the initial decades of his career, he held leadership positions in the claims division of the insurance industry. As his career in the claims sector drew to a close, he opted to channel his financial acumen into becoming a registered investment advisor. During his tenure as an advisor, he gained a profound respect for the day-to-day challenges RIAs face. Changing course, Chad discovered that he could make a more significant contribution to the financial services community by becoming an insurance advisor to advisors. Now, Chad has the privilege of engaging with advisors across the country, meeting their needs so they can focus on what they do best.

When Chad is not working, you may find him experiencing the great outdoors with his family, where he may be camping, hiking or riding through the mountains.

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Staying Relevant in the Age of AI with David Evans and RJ Malyk (Ep. 9)

Staying Relevant in the Age of AI with David Evans and RJ Malyk (Ep. 9)

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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 radio shaped his approach to AI, why embracing change matters, and how financial services can draw lessons from other fields facing disruption.

Key takeaways:

  • How RJ transitioned from radio to voiceover work and why AI pushed him to expand his skillset
  • The mindset shift needed to embrace change instead of resisting it
  • Parallels between AI’s disruption and past technological shifts like TurboTax and big-box retail
  • The importance of human interaction and personalization in industries threatened by automation
  • Why the 80/20 rule explains the balance between technology and human expertise across fields
  • And more!

Previous Episodes of Interest: 

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Building Trust and Flexibility in Business Development with Pamela Mule (Ep. 8)

Building Trust and Flexibility in Business Development with Pamela Mule (Ep. 8)

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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 shaping the future, and why saying “yes” can open doors to new opportunities.

Pamela discusses:

  • The pitfalls of firms pushing advisors into proprietary boxes instead of prioritizing their needs
  • How genuine relationship building creates long-term recruiting success
  • The importance of adopting modern financial technology and AI tools to stay competitive
  • Why transparency in offers and payout grids matters in advisor recruiting
  • Advice for young professionals in business development: step outside your comfort zone and embrace new challenges
  • And more!

Connect with Rossby Financial: 

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Connect with Pamela Mule: 

About our Guest: 

As VP of Business Development and Recruiting at J.W. Cole Financial, Pamela Mule is passionate about helping independent financial advisors thrive. She focuses on building strong partnerships, identifying growth opportunities, and delivering tailored solutions that support advisors’ independence and long-term success. With a deep understanding of the broker-dealer landscape, Pamela works closely with financial professionals to connect them with the resources, culture, and flexibility they need to grow their businesses and serve their clients more effectively.

With over 15 years of experience in the financial services industry, Pamela has witnessed firsthand how the wrong environment can limit potential and how the right partner can unlock genuine growth. She is committed to partnering with advisors and their teams to explore what a future at J.W. Cole can look like, whether that means achieving true independence, developing a growth strategy, planning for succession, or leveraging innovative technology to modernize their practices. Her approach is consultative, strategic, and always centered on what’s best for the advisor and their clients.

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Building Representation and Openness in Financial Services with Melissa Reaktenwalt (Ep. 7)

Building Representation and Openness in Financial Services with Melissa Reaktenwalt (Ep. 7)

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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 talent, and personal practices for balance have shaped her firm and her life.

What to expect in this episode:

  • Melissa’s intentional efforts to create representation by showing up on stages, conferences, and podcasts
  • Why openness is key when bringing in younger talent and new voices into firms
  • The challenges smaller and younger firms face compared to “OG” legacy firms
  • The ongoing push for diversity, equity, and inclusion in financial services and why awareness isn’t enough
  • How Melissa balances leadership with personal wellbeing through intentional rest, rage runs, and trusting her team
  • And more!

Connect with Rossby Financial: 

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About Our Guest: 

As the Founder and CEO of EViE Financial Group, Melissa Reaktenwalt leverages nearly 20 years of experience in financial services along with credentials as a Chartered SRI Counselor (CSRIC™) and an Accredited Investment Fiduciary (AIF®) to help individuals and small businesses achieve financial wellness and sustainability. She specializes in socially responsible investing (SRI), aligning clients’ values and goals with their investment strategies and decisions, as well as whole-self financial planning.

Melissa is passionate about empowering clients with actionable education and guidance on managing their investments, planning for their financial future, and reaching meaningful milestones. She frequently shares her insights through public speaking, educational workshops, and writing, covering topics such as financial planning, wealth literacy, business ownership, firm growth, marketing, and diversity, equity, and inclusion (DEI).

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From WealthTech Chaos to Clarity with Larry Shumbres (Ep. 6)

From WealthTech Chaos to Clarity with Larry Shumbres (Ep. 6)

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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 Shumbres, CEO and Founder of Archive Intel, about the state of WealthTech, the power of user stories, and the steps to successfully grow and exit a tech company. Larry also shares insights on AI adoption and the importance of iterative product development.

Larry discusses:

  • The evolution of WealthTech and why too many disconnected tools frustrate advisors and firms
  • How the lack of user stories and persona mapping leads to gaps in product functionality
  • The importance of building for smaller firms first, iterating, and scaling up to enterprise clients
  • Why advisory firms risk falling behind if they avoid AI and how to integrate it effectively
  • Key metrics, processes, and readiness steps for selling a tech company at a strong valuation
  • And more!

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About our Guest: 

Larry Shumbres is a seasoned entrepreneur and prominent figure in the FinTech sector, is dedicated to elevating the investment journey for both advisors and institutions through innovative and regulatory-compliant technology. With a wealth of experience spanning over 20 years and affiliations with industry giants like Charles Schwab, Morningstar, and New York Life Investments, Larry’s expertise is widely acknowledged. He recently founded, developed, and successfully exited Totum Risk, a pioneering risk tolerance platform, to TIFIN. Prior achievements include building SmartVision by eVestment, acquired by Nasdaq, and leading the sales team at eMoney, culminating in their acquisition by Fidelity. A sought-after advisor, Larry sits on multiple corporate boards, contributes to NASDAQ as a writer, publishes articles in industry journals, and has been featured in interviews on Bloomberg.

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Practical AI for Real-World Use with David Evans (Ep. 5)

Practical AI for Real-World Use with David Evans (Ep. 5)

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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 into the myths, fears, and realities of AI, from its 70-year evolution to the transformative “Attention is All You Need” paper, and how today’s large language models (LLMs) can be powerful workflow tools rather than just flashy novelties.

Andrew and David discuss:

  • Why finance has been slow to adopt AI and what is really behind that hesitation
  • The surprising ways AI can (and cannot) think
  • Practical, compliance-conscious steps for integrating AI into your daily work
  • How to spot hype versus real utility in an AI tool
  • And more!

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About Our Guest:

David Evans is a Senior Machine Learning Model Developer at Duolingo, specializing in large language model applications for language learning. With a career that spans Google, multiple tech startups, and cutting-edge AI research, David brings a unique perspective on how AI is built, deployed, and adapted to solve real-world problems. His current work focuses on creating high-quality, freeform conversation experiences for Duolingo Max users, blending technical expertise with an understanding of human learning.

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Why Gen Z Thinks Finance Needs a Makeover with Caileigh Carfang & Drew Keesee (Ep. 4)

Why Gen Z Thinks Finance Needs a Makeover with Caileigh Carfang & Drew Keesee (Ep. 4)

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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 Caileigh Carfang, Administrator at Rossby Financial, and Drew Keesee, Technical Liaison at Rossbyl. Together, they take an unfiltered look at what Gen Z wants from financial services, both as clients and as professionals. 

Key Points:

  • Gen Z perceives financial advisors as unnecessary due to the abundance of online information, yet many overlook the importance of guidance and accountability
  • The financial industry often feels exclusive or intimidating to younger and less affluent individuals, especially women
  • There’s a strong need for consolidation of tools and better workflow systems to reduce stress and complexity for both advisors and staff
  • Over-reliance on automation and AI has led to a loss of genuine human interaction, which Gen Z values more than expected
  • A shift in mindset is happening, with younger generations craving personalized advice and authentic relationships in their financial journeys
  • And more!

Previous Episodes of Interest:

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Building a Future-Ready Firm and Living with Curiosity with Frances Toler (Ep. 3)

Building a Future-Ready Firm and Living with Curiosity with Frances Toler (Ep. 3)

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What does it take to build a financial practice that thrives beyond your own career and still leaves you time to pursue passions?

In this episode of The Outstanding Shift, Andrew Evans sits down with Frances Toler of Toler Financial to discuss intentional business structuring, succession planning, and the balance between personal identity and professional life. 

Fran also shares her deep love for birding, how nature fuels her curiosity, and why exploring outside the office matters just as much as growth within it.

Fran discusses:

  • The challenges seasoned advisors face in retiring and why many avoid it
  • Strategies for creating a multi-owner, department-led firm for long-term continuity
  • How to maintain personal identity without letting your practice completely define you
  • The value of curiosity and nature exploration as personal and professional inspiration
  • Birding as a gateway to understanding the interconnectedness of the natural world
  • And more!

Resources:

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About our Guest: 

Frances Toler, CEO of Toler Financial Group, provides fee-based financial planning and investment management for a diverse clientele. Fran celebrates over 23 years of experience in helping people, families, and businesses discover, plan, and implement strategies to achieve the security and prosperity they value. Many of her clients seek out her experience with sustainable investment options, income strategies, and a “planning first” approach.

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Lindsay Evans on Building Products People Actually Want (Ep. 2)

Lindsay Evans on Building Products People Actually Want (Ep. 2)

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Do your products solve real problems or are they just shiny distractions?

Lindsay Grace Evans, VP of Product at Kare Technologies, joins her husband and host Andrew Evans to unpack what it takes to create meaningful products and services.

They explore how curiosity, transparency, and intentional iteration lead to better outcomes for both businesses and their clients.

This episode is a must-listen for anyone trying to shift from good intentions to outstanding impact.

Key Takeaways:

  • The importance of understanding the deeper “why” behind what customers say they want
  • How product design should focus on outcomes and emotional impact, not just functional features
  • The role of failure, iteration, and curiosity in building better products and services
  • How oversaturation and complexity (especially in fintech) dilute effectiveness and client satisfaction
  • How advisors and companies can engage users meaningfully through dialogue, not just surveys
  • And more!

Connect with Rossby Financial: 

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Connect with Lindsay Grace Evans: 

About our Guest: 

Lindsay Grace Evans is a passionate product leader dedicated to enhancing the user experience and expanding access to care for older adults. Growing up surrounded by grandparents and great-grandparents, she developed a deep sense of empathy, patience, and a drive to solve complex problems,  values that continue to shape her approach to leadership and innovation. Combining this personal connection with her expertise in product strategy, she is committed to delivering innovative, data-driven solutions that improve the quality of life for seniors, caregivers, and care teams alike. She believes the most impactful products stem from a balance of quantitative insights and deep human understanding, ensuring that technology not only solves problems but also reflects the needs, dignity, and experiences of the people it serves.

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