“5 Things To Look For When Hiring a Financial Planner or Financial Adviser”, with Tony Drake and Tyler Gallagher

Tyler Gallagher
Dec 6, 2019 · 7 min read

Hire an advisor who has strategic relationships with other experts. We work with CPAs, elder law attorneys, estate planning attorneys and insurance experts. There are a lot of moving parts to your retirement plan, and it’s important these parts are working together.

As part of our series about what one should look for when hiring a financial planner or adviser, I had the pleasure of interviewing Tony Drake, CFP®. Tony is a CERTIFIED FINANCIAL PLANNER™and the founder and CEO of Drake & Associates in Waukesha, Wis. Tony is an Investment Adviser Representative and has helped clients prepare for retirement for more than a decade. He specializes in asset preservation, retirement planning and tax strategies. Tony hosts The Retirement Ready Show on WTMJ Radio each week and is featured regularly on TV stations in Milwaukee. Tony has been quoted in several national publications, including Forbes, The Wall Street Journal, USA Today, US News & World Report and Buzzfeed. Tony is passionate about building strong relationships with his clients so he can help them build a strong plan for their retirement. He trains and mentors other advisers around the country, conducts educational seminars and regularly speaks at national conferences, including a recent talk at the NASDAQ exchange.


Thank you so much for doing this with us, Tony! Our readers would love to ‘get to know you’ a bit more. Can you tell us a story about what brought you to this specific career path?

grandparents on my mom’s side were children of the Great Depression. They were great savers but terrified to spend their money. They did very little in retirement and could have enjoyed themselves more than they did. On my dad’s side, my grandfather jokes that he is living too long. We have had to make adjustments to ensure he doesn’t run out of money.

These experiences have shown me that people need financial education and retirement planning help. Married couples come into our office terrified to retire; they want to retire and enjoy their life but are afraid to spend their money. There is nothing more rewarding than walking them through the numbers in a way they understand and explaining how they can achieve a lasting, meaningful retirement. The end result is often tears of joy, because for the first time ever, they feel confident and comfortable entering retirement. To have so many people trust you with such an emotional decision is an incredible feeling.

Can you share a story about the most humorous mistake you made when you were first starting in the industry? Can you tell us what lesson or takeaway you learned from that?

My first office was in the basement of an old building. I was anxious and excited about starting my business and would look out the window to watch as each new client pulled into the parking lot. The windows were up high, and I could see their feet as they came up the sidewalk. One day, I saw an old, rusty pickup truck pull in. A man wearing dirty shoes and worn jeans walks toward my office. I immediately made an assumption that this man didn’t have any money saved and I wouldn’t be able to help him. That couldn’t have been further from the truth; this man is still a client today. He’s a wonderful person and is a multi-millionaire who doesn’t value material things. This was a great lesson to not judge a book by its cover.

Are you working on any exciting new projects now? How do you think that will help people?

We are growing and recently bought a building and remodeled to build a classroom right in our office. At Drake & Associates, we believe in education first. This is why we conduct seminars and talk about retirement each week on our radio show. We are launching a monthly education series to encourage people to come in and learn about various financial topics at no cost. Investing in our own classroom gives us the freedom to schedule more classes and with very little notice. If the media is talking about a looming recession, we can schedule a class and educate people on what is happening.

There are so many people preparing for retirement who do not understand their finances and might be intimidated. We pride ourselves on educating people at a level where they are comfortable. We want our clients to play an active role in the financial planning process and to understand the decisions they are making. Education removes a lot of fear and anxiety.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Is there a takeaway or lesson that others can learn from that?

Success really came when we started focusing on the client experience. We are focused on being different and showing we truly care about the people we work with. We understand talking about retirement, long term care and estate planning is uncomfortable. The experience we created makes our clients feel comfortable, and they trust us with these complex and often intimate topics. From having each client’s favorite drink available in the office when they visit to remembering birthdays, the little details make a big difference.

What three pieces of advice would you give to your colleagues in the finance field to thrive and avoid burnout? Can you give a story or example?

1. Find a niche you’re good at and stop trying to be everything to everyone. I started by focusing on health insurance and Medicare supplements, but it’s hard to be an expert on money and stay up-to-date on healthcare. It’s better for our clients if I focus on what I do well and bring in outside experts. We work with CPAs, estate planning attorneys and Medicare experts so our clients can reap the benefits of a holistic financial plan.

2. Stand on your values. For me, family is important. I used to work 12 hours a day, six days a week. As my kids started growing up, I realized I didn’t want to miss things and I needed to be more present in their lives. I don’t want to look back and regret not being there for them.

3. Our work is more than just numbers on paper. When managing clients’ money, it can be easy to see a bunch of zeros on a statement. However, we are dealing with people’s lives. This money is their life’s work; it’s important we understand their fear and anxiety. We focus on bringing clients joy, peace and happiness instead of sales and commissions.

Ok. Thank you for all of that. Let’s now move to the core focus of our interview. As an “finance insider”, you know much more about the finance industry than most consumers. If your loved one wanted to hire a financial advisor (not you :-)), which 5 things would you advise them to find out about before committing? Can you give an example or story for each?

1. Be sure your financial advisor is a fiduciary. As a fiduciary, I am legally required to act in my clients’ best interest. Advisors who are not held to the fiduciary standard only have to make recommendations that are suitable.

2. Ask if your financial advisor has a third party custodian. We don’t hold our clients’ assets; we use a third party custodian who holds the assets and creates our clients’ statements. Nothing can ever be falsified.

3. Find out how your financial advisor gets paid. Ask pointed questions: Are you a fiduciary? What are my internal costs? What is my total cost? Your advisor should be able to answer these questions, and it should be a simple, clear conversation.

4. Pay attention to customer service and remember this will be a long-term relationship. Send an email or leave a voicemail to see how long it takes to get a response. Our relationships with clients are about more than money. Look for an advisor who will help you reach your financial goals for the rest of your life. This person should adjust to your needs and can answer your financial questions in a way that’s easy for you to understand.

5. Hire an advisor who has strategic relationships with other experts. We work with CPAs, elder law attorneys, estate planning attorneys and insurance experts. There are a lot of moving parts to your retirement plan, and it’s important these parts are working together.

I think most people think that financial advisors are for very wealthy people. This is likely not actually true. Can you explain who would most benefit from hiring a financial advisor and why? Can you give an example?

Anybody who feels they are not good with money or doesn’t know where to start should hire a financial advisor. Regardless of how much money you have, a financial advisor can help you become educated and feel confident in your finances. Even if you feel you have a good grasp on your financial situation, a financial advisor can help you create a comprehensive retirement plan that integrates tax strategies, a Social Security strategy and is conscious of internal costs. We all have different goals and are in a different place financially. A good fiduciary advisor will look at your unique situation in a dynamic way that will benefit you long-term.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My parents were both factory workers. We didn’t have much growing up, but we did have a lot of love. My parents really stressed the importance of education, learning new things and encouraged me to ask questions. They instilled a belief in me that if I worked hard, I can be anything I want to be. This work ethic has gone a long way in my life. I appreciate the way my mom and dad raised me; I never dreamed of living the life I have today.

How can our readers follow you on social media?

Twitter — @TonyDrakeCFP

LinkedIn — https://www.linkedin.com/in/tony-drake-cfp/

Facebook — https://www.facebook.com/Drakeandassociates/

Thank you so much for joining us. This was very inspirational.

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Tyler Gallagher

Written by

CEO and Founder of Regal Assets

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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