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Our mission is to inspire our clients to make informed financial decisions through ample information, clear communication and excellent customer service, all while exceeding their expectations. Drakes and Associates helps friends and neighbors throughout the greater Wisconsin and Michigan area work toward their financial goals through the use of insurance and investment products. We are rooted in the community and have developed our business by creating close, personal relationships with our clients. When you have financial concerns, we want to help you address them.

Market fluctuations and economic uncertainty can present challenges for your financial strategy, and it may take more than just market performance to provide you with the confidence you deserve for your financial future. That’s why we are committed to earning your trust, thoroughly understanding your goals and dreams, and helping you feel confident in your financial strategies. With Drakes and Associates, helping you meet your financial needs is our first priority.

It’s our responsibility to evaluate and assess your financial situation and only make recommendations that are in your best interest, and we do so with integrity and transparency. Our experienced professionals are not just knowledgeable about finances, we also understand the importance of priorities, family and confidence in your financial future.

Schedule a complimentary consultation

Contact us at or call us at 414-409-7226 to schedule a time to discuss your financial situation and the potential role of insurance or investments in your financial strategy. 

Tony Drake, CFP®

Tony Drake was born and raised in Milwaukee. He graduated from Pius XI High School and went on to receive his insurance licenses, post-graduate certificate from DePaul University and CFP® designation. Tony is an Investment Advisor Representative. With over 15 years of experience in the financial industry, Tony has served clients from all over the country and specializes in asset preservation, retirement planning and tax reduction strategies.

In addition to serving his clients, he trains and mentors other financial professionals all over the country. He has made appearances on Milwaukee’s FOX-6, CBS-58, TMJ4, WISN-12, NASDAQ, USA Today, Forbes, US News, CNBC, MSN, PBS, Wall Street Journal, TheStreet, Yahoo! Finance, Investopedia, Market Watch and Kiplinger. Additionally, he hosts the “Retirement Ready” podcast and radio show on 620 WTMJ-AM Saturdays at 11 a.m.

Tony lives in Oconomowoc and has three beautiful children. As a family, they participate in waterskiing tournaments all over the country and love sports and spending time together. Tony bow hunts and owns Wirehaired Pointing Griffons — you can often find him pheasant hunting with friends.

It’s never too late to take the first step or get a second opinion.


Drake and Associates’ mission is to inspire our clients to make informed financial decisions through ample information, clear communication and excellent customer service, all while exceeding their expectations. Our primary areas of focus include retirement income strategies, wealth management and conservative retirement planning.


Financial Independence

It is important to feel you have control over your future. At Drake and Associates, we offer our experience and knowledge to design a specific plan of action that helps you work toward your financial independence.


One-on-One Meetings

At Drake and Associates, we hold informational webinars for our clients and the greater community that feature information on specific topics, such as retirement income strategies and wealth management. We strive to keep you up to date on issues that matter to you, your family and your financial well-being. Whenever you attend a webinar, feel free to schedule a one-on-one, no-obligation meeting. 

Retirement Planning Kit

Our helpful retirement kit includes three guides that address topics you should consider when planning your retirement. Enter your information to get your guides!

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