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“Don’t make any assumptions.” With Tyler Gallagher & Kyle Winkfield

It’s not about assets under management, commissions, fees or premiums. This is about people’s lives. When you figure out that you play a major role in the trajectory of their lives, it should frame how you approach their money and planning. It’s not about you or your firm, or your sales quotas. I had the […]

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It’s not about assets under management, commissions, fees or premiums. This is about people’s lives. When you figure out that you play a major role in the trajectory of their lives, it should frame how you approach their money and planning. It’s not about you or your firm, or your sales quotas.


I had the pleasure of interviewing Kyle Winkfield. Kyle Winkfield is a breath of fresh air to the financial industry, empowering clients and public audiences through education and straight-forward concepts. Personal finance is a topic that unnerves many Americans and the barrage of industry jargon and fast talk leaves most uncertain about what is best for them and their families. A portfolio is not a plan, and what sets Kyle’s clients apart from the rest is they have a written plan for retirement achieving financial freedom and lifestyle security. Known for his passion and heartfelt teaching style, Kyle’s voice is often heard on the air, in print or online.


Thank you so much for doing this with us! 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?

I grew up in a household that avoided discussing money. Whenever the conversation about money was brought up, it was surrounded with negative energy. “Put that down” “We can’t afford that” “That’s for rich people” and just straight up “No.” What drew me to the field was a desire to be financially successful as an adult. I figured the best way to learn about money was to work with it; the best way to have command of something is to teach it to others.

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?

I had two family members come in for a meeting, both with the same last name, but a substantial age gap, so I assumed they were a parent and child. I made the mistake of saying “what provisions do you want to establish for your son here”? They started raucously laughing. They quickly clarified that they were a couple that had been married for two years. I laughed and said “oh wow, you’ve got game!” We all had another good laugh and got back to estate planning.

The lesson? Don’t make any assumptions based on age, appearance, gender, etc.

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

Yes, stay tuned!

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?

The real tipping point for me was when I found out the difference between a captive agency and the being an independent advisor. I realized that the large big name firm I began my career at was only allowed to advise people to purchase the products of that firm/brand, even if the client needed a strategy that wasn’t incorporating these financial products.

The only way that you can truly provide unbiased advice is being free to access all the products and strategies available in the marketplace. The key is having access to all it. Considering these large big name firms don’t offer all products and strategies under the sun, they control your access and manage your awareness of the real options available. In fact, these firms would create a negative narrative to steer clients away from learning more about all the options.

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. It’s not about assets under management, commissions, fees or premiums. This is about people’s lives. When you figure out that you play a major role in the trajectory of their lives, it should frame how you approach their money and planning. It’s not about you or your firm, or your sales quotas.
  2. The majority of the actions you take professionally each day are the result of habits. Your success or lack thereof is tied to two to three key habits you execute daily.
  3. You won’t ever feel stressed or burned out if you’re always doing what is in the best interests of the people you’re serving. I’ve been in this industry for 20 years and have weathered three financial crises (tech bubble, the financial crisis of 2008 and now the COVID-19 crisis). Clients never have called me in a panic; in fact in the past two months I’ve received so many thank you calls and gift baskets, which is an amazing feeling. These gestures are completely opposite from what other professionals in my field experience. You should be planning for your clients’ financial future in such a way that you don’t have to worry about panicked phone calls from clients when the market goes down.

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. Are they an independent financial professional? If the advisor you’re interviewing works for a large big name brand firm, or one that is backed by a major logo’d firm, they most likely are not. As I mentioned earlier, the inherent problem with big logo’d firms is that they only advise you of the products and strategies they offer.
  2. Are they a fiduciary? A true fiduciary puts the best interests of the client first, no matter what. In the financial industry, a real fiduciary offers unbiased guidance in both investment and insurance products and strategies. You cannot be a true fiduciary if you only have access or licensing to one category of strategies and products. For example, there are investment-only fiduciaries who offer unbiased advice for investment-only products, but they are not fiduciaries in a full financial sense. They only advise on investments in the market.
  3. What is their focus or expertise? Like the medical profession, just because you’re have an MD attached to your title, doesn’t mean that you should be performing heart surgery. If you’re seeking retirement planning and income security, you need to be speaking to someone whose specialty is retirement income planning.
  4. Test their product agnosticism. Are they biased, leaning toward investment products or only insurance-based products? You want them to look at products as tools and not have a bias; the products employed should be 100% reflective of the client’s needs and wants.
  5. What is their “Why”? Why are they in this industry? If you’re trusting someone with your financial future, your life savings, it’s important to be comfortable with who they are as a person in addition to the aforementioned.

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?

Financial advisors are not a one-stop shop, they have varying specialties. As a result, it’s not so much who benefits the most from hiring one, it’s more about what do you need when you’re looking for one? There are advisories who focus on debt management and elimination, there are those who focus on investing, or there are those who specialize in retirement income planning. The type of advisor you need or would benefit the most from depends on where you are in life and what your priorities are.

For example, someone who is preparing for retirement should seek an advisor whose focus is preservation, making sure their savings will last them through their retirement years, not an advisor whose main objective is asset growth. At the end of the day, it is really important to figure out what you need. Everyone benefits from financial guidance, just like everyone benefits from having healthcare, it’s not something for just one segment of a population.

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 wife. Being an independent advisor is a more difficult path to take in our industry simply because we do not have the financial backing marketing dollars to promote our brand and our agenda nor name recognition branding like the large logo’d firms. It’s a double challenge to be both an independent financial advisor and a business owner, and without the support of my wife, I don’t know if I would have made it to where I am today. She believed in what I was doing and cashed out retirement savings plans to finance the company in the early years (that’s not advice I would give to any clients, but thanks so much Ash!).

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

As boring as this advice may be, it’s the most relevant advice I could possibly provide given our current times — save. Save like your life depends on it. Many households are not currently positioned for saving any money given the current crisis we face, but I don’t think I have to explain why saving is so critical. American culture has fallen victim to excess; most Americans are all about current lifestyle comforts over future lifestyle requirements. I think this pandemic and quarantine is reinforcement enough of how much you can really live (happily) without, and why saving for tomorrow’s unknowns is so critical.

How can our readers follow you on social media?

Instagram: https://www.instagram.com/finleyalexanderwealth/

Facebook: https://www.facebook.com/FinleyAlexanderWealthMgmt/

Twitter: https://twitter.com/WealthFinley

YouTube: https://www.youtube.com/channel/UCRxemVR4uaP07kn2XXEz-NA

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