About The Firm, Fees and Jake
About Oak Street Investments
Oak Street Investments, founded by Denver-based investment advisor Jacob Milder, is a fee-only investment management and comprehensive financial and tax planning and tax preparation firm with a mission to help clients clarify, plan for, and achieve their financial goals. Fee-only means that we are fiduciaries in every engagement, and that our compensation comes directly and only from our clients; never from product sales, commissions or referral agreements.
We combine a low-overhead operational structure with the latest technology to offer our services at a transparent, fair price.
Why Flat Fees
It's really fairly simple: it's a win-win structure for clients and the Firm. In early 2019, after evaluating my then-current client base and business goals, I began transitioning the Firm to a flat-fee model. I recognized only a loose correlation between the time I spent working with a household and that household's wealth.
By using a flat fee for many clients, I can build the firm exactly as I want, support my family, and provide a top-notch, highly customized client experience in a transparent, ethical way (fee-only) without charging high-net-worth clients tens of thousands of dollars per year.
Building a single-member (plus admin) flat-fee Firm means there are some trade-offs: With limited "seats on the bus," unfortunately I cannot serve clients seeking a more limited engagement or those without assets to manage because of these capacity constraints.
...And The Challenges of the Model
After a few years of charging one fee for every household, regardless of complexity or wealth, I came to see some of the fundamental drawbacks to the model; most notably inflation. My operating costs were rapidly increasing, and while there was a small increase in the flat fee new clients paid, fees were not keeping up. Worse, adjusting clients' (flat) fees required signing new agreements - something neither of us wanted.
The traditional 1% AUM model solves for inflation over time with market growth, but that fee seems anchored by industry norms rather than client value. After much time, research, and modeling, I decided to add a low AUM fee for households over a threshold. I genuinely believe this structure, while not perfect, is fair, reasonable, and in my clients' best interest.
About Jake
Hi! My name is Jacob "Jake" Milder, and I'm a Denver investment advisor, Certified Financial Planner™, Chartered Financial Consultant®, Enrolled Agent with the IRS and the founder of Oak Street Investments. I started the firm to provide a less conflicted, enjoyable and more transparent client experience.
I was born, raised, and educated in St. Louis (Washington University in St. Louis for any WU Bears fans) and began my career as a research analyst for a Registered Investment Advisor (RIA) in Clayton, Missouri.
My career in Finance started where most do- at the bottom of the corporate ladder, working as an intern at a leading insurance company. Five years later, I was managing a team of 40 when I accepted a position in Chicago as a VP at Goldman Sachs, managing a team for mutual fund distribution and the occasional private equity offering. In 2014, I moved back to Denver and shortly thereafter launched Oak Street Investment Advisors, LLC.
In my 20+ year tenure in financial services, I've worked with hundreds of financial advisors and their clients to help them build stronger relationships and better financial plans and portfolios. Yet I've only come across a handful whom I would trust with my friends' and family's money: people who not only place the interests of the client ahead of their own but are also honest and clear about their fees, investment philosophies, and financial planning process.
I love what I do and have fun doing it, so when clients choose to work with me, they know they get the true, transparent, and authentic Jake — imperfections, bad jokes, opinions (sometimes unsolicited), and all!
Today, I live in South Denver with my family and two dogs (yes, they're also part of the family). When I'm not working, you'll find me spending time with my family, hiking, woodworking (I'm not good), crosswording, skiing, playing tennis, meditating, and memorizing useless car facts because I can't help it! In 2026, I earned my black belt in Tae Kwon Do, almost 40 years after starting (I paused classes for a few decades). I'm a subpar golfer - not in a good way, an avid reader of financial publications, and a javaphile - I had to look it up, but I'm sure you can figure it out!
How I Can Help
While every financial plan is unique, I may be able to help you:
- Feel more secure and confident about your future (and your family’s future)
- Connect with other professionals, such as accountants, attorneys, and insurance brokers —without referral fees, revenue shares or commissions
- Save thousands of dollars by transitioning from high-cost to low-cost investments
- Allocate income in order to maximize tax savings
- Form a more strategic loan payoff plan
- Evaluate the right retirement plan for your small business
- Determine how much to save and where to save it
- ...and a whole lot more.
Most importantly, my clients feel a sense of relief in hiring an investment advisor they know is competent, ethical, transparent, and fun. There's a sense of confidence that comes with knowing you're on the right path and you have a partner with financial expertise walking it with you. There's also a sense of freedom, of re-discovered time that can be allocated away from your financial life and toward the things that matter to you most.
I do limit — and will always limit — the number of clients I take on to ensure a quality and personal relationship with each and every one of those I work with. Reach out today to ask about my availability and to see if we may be a good fit for one another.
