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!

Connect with Rossby Financial:

• (321) 209-0111
• Website: Rossby Financial
• Website: ROffice
• LinkedIn: Rossby Financial
• Instagram: @rossby_wealth

Connect with Andrew Evans:

• LinkedIn: Andrew Evans
• Email: aevans@rossbyfinancial.com

Connect with Leslie Lipscomb:

• LinkedIn: Leslie Lipscomb
• Website: Financial Independence Group
• (704) 971-7760

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.

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!

Connect with Rossby Financial:

• (321) 209-0111
• Website: Rossby Financial
• Website: ROffice
• LinkedIn: Rossby Financial
• Instagram: @rossby_wealth

Connect with Andrew Evans:

• LinkedIn: Andrew Evans
• Email: aevans@rossbyfinancial.com

Connect with Chad Ramberg:

• LinkedIn: Chad Ramberg
• Website: Box Professional Insurance
• chad.ramberg@boxproinsurance.com

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.

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:

• Lindsay Evans on Building Products People Actually Want (Ep. 2)
• Practical AI for Real-World Use with David Evans (Ep. 5)

Connect with Rossby Financial:

• (321) 209-0111
• Website: Rossby Financial
• Website: ROffice
• LinkedIn: Rossby Financial
• Instagram: @rossby_wealth

Connect with Andrew Evans:

• LinkedIn: Andrew Evans
• Email: aevans@rossbyfinancial.com

Connect with David Evans:

• LinkedIn: David Evans

Connect with RJ Malyk:

• LinkedIn: RJ Malyk