Hi, I'm Andy 👋, founder of Two Trails Financial Planning

andy headshot looking at camera

The Essentials

  • Former teacher

  • 9+ years of experience in financial services

  • Master of Science in Financial Planning

  • Named one of Money Magazine’s “Best Financial Planners”

  • Certified Financial Planner (CFP®) professional 

  • Certified Friendly and Approachable Person (CFAP)*

  • Proud husband and father

*I definitely made this one up, but it’s true!

What's Andy like outside of work?

When I'm not creating financial plans or meeting with clients, you can typically find me:

  • Reading

  • Hanging out at the lake with family and friends

  • Hiking

  • Traveling (27 countries and counting!)

  • Enthusiastically ignoring our monthly food budget at our local farmer's market

  • Visiting family and friends in my home state of Colorado

baxley family
andy and kids

Fun Facts About Andy

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My most important people: Yi (my wife), Kai (1), and Bo (3)
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My top 5 personal values: family, meaningful work, connection, curiosity, challenge
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My happy place: Promontory Point, Chicago
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My hero: My dad (he never missed a baseball practice!)
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Favorite travel destinations: Iceland, Japan, or any of the national parks
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Favorite personal finance book: The Psychology of Money by Morgan Housel
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Favorite musician: Fred Again.. 
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Favorite movie: Arrival 
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What I'm thinking about: How to be a great dad and how to provide a level of personalized service that makes my clients say "wow”
Andy’s Professional Journey
My interest in financial planning began unexpectedly in 2013 while teaching English in South Korea. A chance encounter with the book "Millionaire Teacher" revealed a profound truth: financial security and abundance aren’t just for the wealthy; they’re achievable for anyone with the right knowledge and plan.
This insight ignited my curiosity. I devoured every personal finance book and blog I could find, eager to share my newfound knowledge with friends and colleagues. It wasn't long before I realized that this interest could be more than just a hobby—it was my calling.
My professional journey in financial services began in 2015 at Fidelity Investments, where I became a top performer in both retail and institutional advisory roles. In 2017, I transitioned to TIAA, initially joining a pilot team of advisors tasked with redefining how TIAA delivered financial advice at scale to its core clients. This innovative experience led to my promotion as a Wealth Management Advisor at TIAA in 2019, where I helped high net worth and ultra-high net worth clients plan for retirement. While this experience was invaluable, I found myself spread thin across hundreds of clients. Driven by a desire for deeper client relationships, I joined The Planning Center in 2020, a firm I had long respected and admired for their unique life-centered approach to financial planning. There, I refined my approach working closely with about 50 families. I also had the opportunity to learn what it takes to run a successful, client-focused advisory firm.
Where you’ve seen Andy:
cnbcyahoo financeinvestment newsmoneywall street journalusa todaykiplinger
The Two Trails Approach
As a financial planner, I'm driven by the belief that money is a tool for crafting a life of purpose and fulfillment. My approach goes beyond numbers. With an academic background in psychology, I dive deep into my clients' motivations, personal stories around money, and sources of joy. I believe that true financial planning is a collaborative process that empowers individuals to make informed decisions aligned with their values.
The name "Two Trails Financial Planning" embodies the core of my philosophy. The first trail represents the default path, the status quo—the one we often follow due to expectations, societal norms, or inertia. The second trail is the creative path—the one that excites and inspires us, feels authentic, and maybe a little scary. It requires courage and planning to successfully follow this path, but in my experience, it's also where fulfillment lies.
My own experience of leaving a secure, well-paying job to start Two Trails was a pivotal moment. Despite the fears and uncertainties inherent to any entrepreneurial endeavor, I knew I'd always regret not trying. Taking that leap has filled me with an energy and enthusiasm for my work that I never thought possible, allowing me to provide a truly exceptional experience for my clients.
baxley family
andy and yi smiling
The Two Trails Purpose
At Two Trails, I've built a practice with two core goals: to provide unparalleled service to a select group of families, and to be present for my own family—my wife Yi and our boys, Bo and Kai—in the same way my father was for me. My dad, also a small business owner, showed me that it's possible to build a successful career without sacrificing what matters most—time with loved ones. 
This philosophy is at the heart of my practice. I help my clients find balance between preparing for the future and living fully in the present. Because while it's crucial to plan for tomorrow, we must also embrace the life we want today.
Whether you're looking to optimize your finances, plan for a major life transition, align your money with your values, or simply gain more clarity and confidence in your financial decisions, I'd be honored to join you on your journey. Together, we'll create a financial plan that not only secures your future but also enriches your present.
Let's find your trail and build a life you can be proud of—starting now.
Let's Connect

If you're looking for a guide to help navigate your own “two trail moments”, I'd love to connect and learn more about your unique situation. Together, we can chart a course that aligns your money, time, and talents with what (and who) truly matters to you.

Schedule a Consultation