Financial Independence
is a Journey
Worth Taking

We’ll be your financial guide so you can spend more time…

with family and friends

in the mountains

going on adventures

building your career

doing what you love

more info


Financial planning designed to help you get more out of life

Do you have these types of questions? We can help!

How much should I be saving and how should I allocate my cash flows in order to achieve / sustain financial independence?

What does financial independence look like for me and how do I get there?

How can I optimize my employee benefits?

Am I on track to retire and how should I plan for retirement?

What should I invest in and how should I allocate money among my investments?

How can I protect my family financially in case something happens to me?

People commonly spend a lifetime serving their financial choices. We specialize in the uncommon – using money to work for you and increase your freedom in life.

Jake Thorkildsen, ChFC®

Founder, Trailguide Financial, LLC

Getting Started

Introductory Meeting

This is a no-cost and no-pressure meeting just to see if we are good fit for each other. If you’d like to move forward, we may have another call to detail the relationship, costs, and start the onboarding process.

Getting to know you

Once we’ve decided to work together, we’ll start with a deep dive into your finances, life and career aspirations, values, financial independence goals, and much more. To build a financial plan for you, we have to know you first!

Plan Design

From here, we get to work designing a plan which is custom tailored to you. Your plan will cover the areas most important to you: cash flow, budgeting, investing, risk management, retirement planning, and more.


We believe financial planning is best done as part of an ongoing relational process – and we know that life happens fast! Once the plan is made, we’ll work together to implement it, keep it up to date, and guide you through your financial life stages.

Who We Serve

We are passionate about financial planning and believe that it should be undertaken as early in life as possible. The best time to start is right nowwhether you are retired, nearing retirement, or just graduated college! Accordingly, we enjoy working not just with folks nearing or in retirement, but also those in the early-to-mid career ‘accumulation’ stage – and we’ve setup our fee structure to be affordable and add value during whatever life stage you are in!

We’ve found the best advisor/client relationships occur when our values are mutually aligned. We most enjoy working with those who are drawn to the idea of using money as a tool to enhance freedom in life and the actualization of life values rather than simply having wealth accumulation be the end goal in and of itself. We place a high emphasis on the ‘WHY’ behind the how and what we use money to accomplish.

Our clients typically place a high value on family, freedom, friendship, and generosity. If this sounds like you, we should talk!

Financial Planning Areas of Emphasis

While it will look differently for each client, the chart below reveals a lot about how we approach financial planning. While much of industry is 90-100% focused on investing, we are much more focused on a holistic approach which encompasses the complex and unique interactions between many different areas of personal finance.

  • Financial Coaching / Planning
  • Investing & Retirement Planning
  • Cash Flow Management
  • Risk Management
  • Education Planning
  • Estate Planning
  • Tax Planning


  • Early to mid-career stage financial planning – we are passionate about helping those in this life stage create a foundation for success. So many choices are made during these years with dramatic implications for financial independence. We add value by guiding clients through these major life/financial decisions.
  • Real estate investors, agents, and brokers. We love real estate and Trailguide’s founder has an extensive real estate background. We find that those in this industry often have unique challenges and opportunities which we very much enjoy helping with.
  • Retirement planning  Whether retirement means 65, later, or much earlier – one of the chief concerns is allocating assets in such a way as to effectively mitigate the risk of the loss of ‘human capital’ (wages) and using financial capital (investments) to sustain our day-to-day cost of living. We can work together to create a financial and investment plan to help meet your goals.
  • Sudden wealth – when one receives an inheritance or life insurance, there are many factors to consider and we highly suggest seeking qualified financial advice. We are here to listen, understand, and patiently assist you through this challenging time by helping you make prudent financial decisions.


About Trailguide

Trailguide is an independent financial planning and investment management firm. We operate as a ‘fee-only’ firm, which means that we do not work on a commission basis – we feel this structure enables us to better serve our clients. We believe in transparency and the benefits of being an independent firm.

Trailguide was founded by Jake Thorkildsen. Jake is a husband and father who has the heart of a teacher and an adventurous spirit. He has the Chartered Financial Consultant® (ChFC®) designation, which is only attained after completion of a comprehensive educational program in financial planning. He graduated magna cum laude from the University of North Texas in 2008 with a degree in Finance at age 20.

Jake’s professional background includes wealth management, financial analysis, real estate investment, and private equity. Jake has a passion for personal finance and enjoys leveraging his multi-disciplinary financial background to help clients wisely manage their financial resources. In his free time, Jake enjoys spending time with family and friends, reading, hiking, mountain biking, and adventure motorcycling. He and his family live near Bend, Oregon.

Professional Affiliations

Let's chat - don't be shy!

We’d love to meet you and discuss whether working together could be a good fit – no cost, no pressure!