Bringing Humanity Back into Retirement Planning with Jason Weaver

This week, Kyle Van Pelt talks with Jason Weaver, Managing Partner of Weaver Consulting Group. With nearly three decades of experience in the financial services industry, Jason leads with a people-first philosophy rooted in mentorship, emotional intelligence, and community. 

Kyle and Jason unpack why financial planning today requires more than performance charts and retirement projections. Jason describes his mentorship-first approach to helping young people break free from the instant gratification of sports gambling and develop healthier, long-term investing habits. By fostering in-person community, accountability partnerships, and meaningful client events, he’s building trust and transformation that lasts beyond market cycles. Their conversation highlights how true advisory work is ultimately about alignment—connecting money with personal values, emotional well-being, and the relationships that support growth across a lifetime.

In this episode:

• (00:00) - Intro

• (00:50) - Jason's money moment

• (04:11) - The rise of sports gambling and its impact on young investors

• (08:03) - How Jason helps teens shift from gambling to investing through mentorship

• (12:32) - Jason’s five core beliefs and how they shape behavior and financial decisions

• (17:10) - Why in-person community is essential for trust and transformation

• (19:24) - Bringing humanity back into retirement planning

• (21:52) - Balancing tech and touch: using digital tools to deepen relationships

• (24:08) - Inside the Weaver Consulting Group tech stack

• (27:39) - Jason’s outlook on the future of the financial services industry

• (30:04) - Jason's Milemarker Minute

Key Takeaways

• Real financial planning is about people, not products. Numbers and strategies matter, but lasting transformation happens through human connection. Advisors create the most impact when they understand clients’ values, emotions, and identity—not just their balance sheets.

• Short-term dopamine behaviors can derail long-term wealth. Sports gambling and similar instant-gratification habits literally retrain the brain. Helping young people shift from betting to investing starts with awareness, accountability, and a supportive community.

• In-person relationships build trust that technology cannot replace. Face-to-face conversations, shared experiences, and community events deepen connection and reinforce healthy financial mindsets. Digital tools can support—but never substitute—the human element.

• Use technology as an amplifier, not a replacement for advisory work. Tech should simplify workflows, enhance communication, and provide clarity—not create more noise. The most effective firms pair smart systems with authentic, values-driven guidance.

Quotes

"We individualize the planning experience and then educate people to understand the strategies we've chosen together to make sure that we can help them have a wonderful life." ~ Jason Weaver

"People don't want just a plan. They want alignment between their money, their values, and their well-being." ~ Jason Weaver

"Invest in yourself first. At the end of the day, your greatest return is yourself." ~ Jason Weaver

Links 

• Jason Weaver on LinkedIn

• Weaver Consulting Group

• Ameriprise Financial

• Fidelity Investments

• Vanguard

• Orion Advisor Solutions

• Redtail Technology

• eMoney Advisor

• Charles Schwab

• The Hum

• The Law of Success

Connect with our hosts

• Milemarker.co

• Kyle on LinkedIn

• Jud on LinkedIn

Subscribe and stay in touch

• Apple Podcasts

• Spotify

• YouTube

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