On this episode of the Stride 2 Freedom Podcast, Chris Welton of Northwestern Mutual breaks down financial planning in a way that’s simple, strategic, and—dare we say—even fun.
A Clearer Financial Path for Business Owners
Many business owners put off financial planning because it feels overwhelming or they don’t yet see themselves as “wealthy enough.” Chris hits this nail on the head: “You can never be too early, but you can be late,” reminding us that waiting often means missing out on opportunities that could compound—not just the numbers, but the impact over time.
Why “Hope Is Not a Plan”
Inspired by Atul Gawande’s philosophy, Chris emphasizes that success isn’t about wishful thinking—it’s about hard, purposeful planning. He likens planning to powerful surgical checklists, but for your finances. It doesn’t promise perfect results, but it ensures you’re set up to control the inputs that drive your outcome.
The Power of Listening—and a One-Page Checklist
Chris builds his plans with two key ingredients:
- Listening first: “This might be the first time I felt really listened to cohesively… I’ve said things out loud that I hadn’t realized I was thinking.”
- One-page simplicity: Beneath a 60-plus-page analysis, lies a powerful one-page checklist: “Here’s what to do, when, and why. Here’s the bottom line.”
The combination creates clarity—and lets clients move forward with confidence, not confusion.
The “Triangle” Approach: Business, Personal & Legacy
What’s unique about Chris’s process is the balance he brings between three interconnected circles:
- Business: Cash flow, employee retention, and enterprise value tools like non-qualified deferred compensation.
- Personal: Insurance planning, retirement vehicles like cash-balance plans, and fiduciary wealth management.
- Legacy: Estate plans, gifting strategies, and the value of planning now while interest rates are low.
As a business owner himself, Chris understands that business and personal finances are inseparable—and this balanced approach shows it.
When Should You Start the Conversation?
Chris describes the mindset he looks for—more than balance sheet size, it’s an “affluent mindset.” This includes business owners generating multimillion-dollar revenues with complexity around structure, taxes, and intentional growth.
If you’re running a business that provides for your family, transitions slowly over time, or feels like your biggest asset, this conversation may already be more relevant than you think.
How Working with Chris Works
Chris offers flexible ways to engage:
- Free initial brainstorming sessions: 20–30 minutes to dream, listen, or explore the road ahead.
- Fee-for-plan: Deep-dive financial plans crafted until clients are satisfied.
- Fiduciary asset management: Where appropriate, Chris can manage client assets with full care, transparency, and independence.
- Insurance and legacy structures: Reviewing buy-sell agreements, life-insurance strategies, and tax-efficient protections for both you and your business.
Why It Matters—and What’s Often Misunderstood
The wealth management industry often comes with marketing noise and confusing jargon. Chris flips that model:
- Client-first philosophy: “What’s good for the client, good things for us will follow.”
- Relatable expertise: With roots in Wall Street deal-making and everyday business leadership, he brings both technical strength and human understanding.
Your Next Step: Don’t Wait—Plan
Listeners—or Stride clients—are already in Chris’s target zone. Whether you’re a solo professional with high income or the owner of a growing team, there’s value here. And before thinking you’re “not big enough” for wealth management—let Chris reframe the game:
“Don’t limit yourself in terms of too big or too small… open the horizons and be open to learning new things and the opportunities that arise.”
Conclusion: Make Simplicity Your Superpower
– Start early: You can be too late—but never too early.
– Embrace a plan: Bring structure and clarity to your financial future.
– Think in three dimensions: Integrate your business, personal life, and legacy into one holistic plan.
– Keep it simple: A one-page checklist can change the game.
Ready to feel confident and in control—whether for your business, your family, or the legacy you’ll leave? Reach out via the original post or schedule your free session with Stride’s advisory team today.
In this Freedom Speaker Series episode with Chris Welton, you will learn:
- The importance and value of a wealth advisor
- The simple power of a plan and checklist
- How to establish a strong client / advisor relationship
We are fortunate to have Chris available to spend time with us on this edition of Stride 2 Freedom. If there is a speaker you’d like us to interview, let us know. Stay well. Stay safe. Stay healthy.
Show Notes and Links From Episode:
Chris Welton
Northwestern Mutual
