FAQs

Frequently Asked Questions
Where did the name 'Trailguide Financial' come from?

I am an outdoors enthusiast (Jake – Trailguide’s Founder – speaking) and for those who know me, it’s no surprise that I chose an “outdoorsy” name. I’ve found that the best part of an outdoor adventure often is the joy of exploring the unknown. And while just picking a direction and going can lead to a great adventure in the outdoors, this is the last thing we want to do with our finances!

I view personal finance as a series of trails we can take – sometimes it looks like a web, and frequently there’s no sign pointing the way for us! Or there are a hundred different signs all saying different things! My vision for this firm is to be your financial guide pointing the way and cutting out all the ‘noise’ so you can focus on the things you love most.

What do you mean by 'financial planning'?

We view financial planning as an activity which takes place on an ongoing relational basis and covers multiple areas. Investing is certainly an important aspect of financial planning, but far from the only aspect. For too long has ‘financial advising’ been synonymous with ‘investing’!

At Trailguide, we tackle areas like investing, cash flow planning and budgeting, financial coaching, tax planning, estate planning, risk management, education planning, employee benefit optimization, and more – all within the context of your specific values and goals. Our financial planning process goes far beyond investment management and instead focuses on helping you get more out of life – using your money as a tool to increase your freedom and achieve the things which are most important to you.

We provide guidance, clarity, focus, accountability, and help you enjoy your money and the process of pursuing, achieving, and sustaining financial independence.

Do you manage investments?

Yes!

We believe there is substantial evidence pointing to the value of utilzing an adviser who brings a disciplined approach to investment management. We will work with you to develop and implement an evidence-based investment strategy designed to meet your goals.

How is Trailguide compensated?

Trailguide’s compensation for client work comes exclusively from our clients in a transparent manner. In the industry, this is called ‘fee-only’ – and it means we do not receive commissions from ‘selling’ products.

We believe one of the largest problems in the financial services industry is conflicts of interest and lack of transparency when it comes to fee structure. When advisers accept commissions from financial companies for selling their products, it lends itself to this question from clients – “Is my adviser recommending this because its best for me or because its most lucrative for them?” Certainly, there are pros and cons to every fee structure, but Trailguide believes its clients should never have to wonder about this! Which is why we do not accept commissions for recommending certain products to clients – in fact, one of the main reasons we are an independent firm is so that we are not beholden to any family of funds, insurance company, or other financial product provider. We work for our clients, not for companies who sell financial products.

Client fees will be spelled out in plain english prior to beginning to work together.

Are you able to work with me remotely?

Yes! We are a location independent firm. We love working with clients in Oregon where we’re located, but we utilize technology to meet via video conference with clients – so as long as you have an internet connection, we’re probably good to go! This allows us to meet with you wherever you live, subject to various regulatory requirements (our concern, not yours!).

How do you work with clients locally?

Trailguide operates from a ‘home office’ and we do not conduct client meetings from there. Often times, local clients will want to meet via video conference simply because of how convenient it is.

However, it is also nice to meet face to face sometimes! To that end, we can meet in a convenient location in Bend, Sisters, Redmond, Prineville, or Madras. We are also often in the Eugene area.

What are your hours? Can you meet in the evening or weekend?

Generally, we are available 8:30AM to 5:00PM PST Monday – Friday. However, we believe that one of the ‘obstacles’ some face in deciding to work with a financial planner is that it simply is not convenient!

Clients should not have to take time off work and drive across town every time they meet with their financial planner! That is why we offer video conferencing as our standard meeting method and may also meet with clients on certain evenings and weekends.

What is your experience with real estate investing?

I (Jake – Trailguide’s Founder) have an extensive real estate investment background and have been involved in well over a billion dollars worth of transactions between working in special servicing (working out deals that have gone bad), commercial real estate lending, and in acquisitions for a real estate focused private equity firm where I specialized in finding, analyzing, and acquiring multifamily properties amongst other interesting work such as engineering the various capital structures utilized in acquiring real estate.

My love for real estate began in college thanks to a particularly interesting professor. I purchased my first property soon after graduating from college and began renting the rooms out to friends – I was ‘house hacking’ before that was really even a term. I love working with real estate investors and agents/brokers because 1) I understand and love real estate, as well, and 2) I therefore understand the unique cash flow, investment, and life planning / goals of people in real estate.

I leverage my real estate experience for Trailguide clients to help them make real estate decisions which are aligned with their goals, values, and fit within their overall financial plan.

Do I need to have a certain amount of money to work with Trailguide?

Nope! We meet you wherever you are in your financial journey. We are passionate about financial planning and believe the best time to start financial planning is right now. While much of the industry has minimums of $500,000 to $1,000,000, we do not have any miminum asset requirement to be a financial planning client. That said, we do have a $100,000 minimum assets under management requirement for clients who only wish to engage us for investment management. See the investment management section on the Services page for more information.

One of the driving reasons for starting Trailguide was to offer an affordable way for young adults (people in their 20s, 30s, and 40s) to have access to a qualified financial planner, in addition to serving the needs of those in or nearing retirement.

Whether you are just out of college and want to start off on the right path, solidly into your career and looking at retirement planning, or already retired – we’d like to chat with you!

Want to learn more?

We’d love to chat with you!