Today we’d like to introduce you to Jake Milder.
Jake, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
I was born, raised and educated in St. Louis. I began my career in financial services at a Registered Investment Advisor (RIA) in Clayton, Missouri shortly after graduation. In 2005, I moved to Denver and began working for a life insurance company (Jackson), where I worked for over five years. It was a good experience and I earned a number of securities licenses, learned about the industry and importantly, learned about working with- and managing- other people. In 2010, I moved to Chicago to lead an internal sales team at Goldman Sachs. While it was an excellent opportunity, what set that experience apart from others was the people. I learned a tremendous amount from those working for me, those I worked closely with and those under whom I worked. Having earned my Certified Financial Planner designation while at Goldman, in 2012, I began working as the financial planner for a team at a large wirehouse (merrill lynch) for a couple of years before moving back to Denver in 2014, where I’ve (thankfully) been since.
Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Absolutely not! I believe few people in their final years reflect on their lives- personal and professional- and say, “yup, that’s exactly how I intended everything to go,” and that’s certainly been the case for me. Some of the hardest moments of my professional life were losing my job through no fault of my own. Sometimes in business, there are decisions made at the top that many, if not most within the organization won’t understand and are often outside of their control. As more time passes, I’m better able to see these obstacles as opportunities I used to gain perspective, hone my skills and can now recognize that I would not be where I am today, doing what I love, without these setbacks.
Please tell us about Oak Street Investments.
Oak Street Investments is a fee-only, comprehensive financial planning and investment management firm committed to providing transparent, unconflicted advice in the best interests of our clients. Oak Street Investments is a Registered Investment Advisor and acts as a fiduciary in every engagement. My goal is to help clients clarify, plan for and achieve their financial goals while saving them time, money and helping them avoid costly mistakes. Fee-only means that my compensation comes directly (and only) from clients, never from commissions, product sales, referral fees or other methods. I believe this minimizes or eliminates potential conflicts of interests.
I charge core clients (those utilizing our financial planning and wealth management services) a single, flat fee, regardless of whether they have $500K or $5MM. This better compensates me for my time, not your success. As technology improves, it allows me to manage assets in a more efficient way, and I think many clients are catching on that it doesn’t take their advisor five times as long to manage $5MM as it does to manage $1MM.! Yet many clients still pay almost five times more!
I setup Oak Street Investments to offer a different solution.
I founded Oak Street Investments after spending my entire career working with and listening to other financial advisors. I spent years listening to how advisors ran their businesses, put their clients in questionable investments based on their own compensation, or didn’t service their clients because they were “too small.” I began planning Oak Street Investments in 2013 and launched in early 2017.
I’m proud to be fee-only and am part of some great organizations that educate people on the various conflicts inherent within the financial planning/wealth management space. While I don’t believe there are many ill-intentioned advisors, the structure and incentives of many firms can make it difficult for clients to understand whose interests are coming first.
Do you look back particularly fondly on any memories from childhood?
Growing up, I was fortunate enough to be sent off to camp for the Summer. Some of my best memories are there, in Northern Wisconsin, waterskiing, horseback riding and just being a kid. Now that I’m a parent, I can see that it’s likely those were some of my parent’s best memories of my childhood too!
Contact Info:
- Address: 5500 Greenwood Plaza Blvd, Suite 130
Ste. 1500 - Website: www.oakstreetinvestments.com
- Phone: 7205156822
- Email: info@oakstreetinvestments.com
- Facebook: facebook.com/oakstreetinvestments
- Twitter: OakStreetIA

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