John Cortale

Founder of The Cortale Group

John Cortale is a Wealth Advisor and the founder of the Cortale Group headquartered in Washington, DC. For over 20 years now, he has been leveraging his vast investment experience to provide comprehensive investment solutions to families and individuals, tailoring his advice for their unique needs and circumstances. John was born and raised in Long Island, New York and currently resides in Bethesda, MD with his wife. Academically, he graduated from the University of Maryland with a dual degree in Finance and Accounting.

Wealth advisory is much more than just a job for John. He has a deep appreciation for how important and how relatively undervalued high-quality investment advice can be for families and individuals. Healthy financial outcomes don’t just happen, they require careful strategic thinking and a solid plan that is implemented in a tailor-made fashion, in step with the contextual surroundings that a family finds themselves in. Over his career he has continued to refine the tenets of his 4-step planning process: determining retirement goals, performing comprehensive stress tests, determining the desired retirement income, and looking after succession planning for after you’re gone. He brings his two decades of experience as a wealth advisor to the table with every client he works with. He’s seen the good, bad, and the ugly – and has the experience to maneuver through whatever waters a client might find themselves in.

On the personal side, John is an avid golfer (with a rather temperamental short game) as well as a global citizen who feels most alive when traveling and experiencing different cultures and cuisines. Most importantly, John appreciates spending quality time with his close-knit family and friends – an ethos that he extends to his clients, treating them with empathy and respect.

Where did the idea for The Cortale Group come from?

I knew from very young that a desk job wasn’t going to suit me. The idea of staring at a computer for hours at a time sounded like torture, and so I steered away from that as best I could. Instead, I wanted to create something of my own where I could really work with people and make a difference in their lives. My financial background gave me the skills to help people with their financial health, something very close to my heart, and I simply haven’t looked back. The Cortale Group represents my dent in the universe, my way of giving back to people – helping them put their best foot forward financially and securing them a retirement they can enjoy, rather than stress about.

What does your typical day look like and how do you make it productive?

I’m a routine-based creature. If there’s too much freeform time in my calendar, something is wrong. I like to structure things as much as possible so I can hold myself accountable and keep building momentum through the day. A typical day will start with a cardio workout which gets the blood pumping and keeps me clear mentally. Then I’ll normally move into a team meeting to touch base with everyone, before racing through a packed day of client meetings. No day is the same, but the structure remains in place to keep me doing what I should be doing, wasting as little time as possible. This means that when I go home to my family, I can rest easy knowing that I’ve squeezed as much as possible out of the day.

How do you bring ideas to life?

Ideas are fragile things; they can appear for a moment and then vanish immediately if you don’t start executing on them. Luckily, I have an incredible team around me whose combined creativity and strategic insights help to nurture fledging ideas and bring them to life. At my best, I’m acting as a facilitator and enabler, providing the resources and support to my team so that they can feel empowered and capable of turning an idea into a fully-fledged concept. When this happens, it can feel like magic – and it’s the sort of stuff that I live for.

What’s one trend that excites you?

This is a difficult one, because the world is in truly unprecedented times at present. I would say that virtual meetings has been a trend that has transformed our business and will continue to do so in the future. This pandemic has forced us to translate a lot of our client interaction to virtual settings and while this has been challenging at times, it has also allowed me to be much more present and engaged with our client base because I haven’t lost all that time in commuting between meetings. In-person meetings won’t go away by any stretch of the imagination, but the virtual versions are a fantastic addition to our ability to service clients holistically.

What is one habit of yours that makes you more productive as an entrepreneur?

It’s tempting to mention some productivity hack here, but the real answer is a keen self-awareness. I’ve really spent a lot of time with my own thoughts, reflecting on who I am as a leader and entrepreneur, and that work pays dividends in a multitude of ways that I could never have expected. Self-awareness is a superpower when you can be honest with yourself and leverage your strengths and weaknesses accordingly, in business and in life. My habitual structure for this includes running, working out, journaling, yoga, etc. Anything to clear the mental cobwebs and spend some time with myself. It’s a gamechanger, I tell you.

What advice would you give your younger self?

I think I would tell a younger version of me to appreciate quality relationships more. I was very ambitious as a youngster and was always striving to improve myself, but in that race, I think I took certain people for granted. As I look back now, everything I value in my life comes down to the quality of my relationships – and I now realize that that’s all that matters.

Tell us something that’s true that almost nobody agrees with you on.

I think that the greatest existential threat we face is a dwindling concentration span. The smartphone generation and the constant digital distractions have completely devastated our ability to focus on one task for an extended period of time, and that is what is needed to do great things. I worry about how we’re going to turn this tide around so we don’t just drown in the minutiae of life.\

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Go first. It’s amazing how many people will wait for problems to arrive and then seek to fix them. If you are proactive and you’re consistently trying to stay one step ahead, you don’t have to go into damage control because you have your finger on the pulse. This is especially true with client services businesses. We are always engaging with clients to keep communication channels open and anticipate their needs before they realize it. By doing this, you hold your destiny in your hands.

What is one strategy that has helped you grow your business?

Constant communication. As a team, we make a point, on a daily basis, of setting up meetings and calls with your clients so that we are at their disposal whenever they need. We have some tech solutions behind the scenes that help us do this at scale, and this proactivity has built an incredible amount of trust which translates into happy clients and increased referrals. Even in the world of investing, people management matters and the better we can communicate, the more we are going to grow.

What is one failure you had as an entrepreneur, and how did you overcome it?

I have a tendency to want to take on everything myself and I’ve found myself stretched too thin on more than one occasion. It comes from a good place but has drastic consequences when I can’t handle what I’ve heaped onto my plate. To overcome it, I’ve been fighting my instincts and looking to install a talented team of individuals who I can delegate projects too without worrying about the results. This has greatly improved our overall efficiency and removes me as a bottleneck.

What is one business idea that you’re willing to give away to our readers?

Some smart financial planner out there is going to start a coaching business that is aimed exclusively at young people who are starting their careers. Often these young professionals have a lot of student debt and can be a bit overwhelmed by the mountain in front of them. If you could help them build some good financial habits, provide some accountability, and empower them to take control of their financial future, I think you’d have an exceptional business that would not only be sustainable but make a real social impact as well.

What is the best $100 you recently spent? What and why?

Acupuncture. I can’t describe to you how powerful it has been for relieving the stress and tension that builds up from running a business. After I’m done, I feel like a new man. Every. Single. Time.

What is one piece of software or a web service that helps you be productive?

I’m normally tool agnostic so don’t like giving very specific recommendations, because everyone’s situation is different, but I will swear by some sort of to-do list software which tracks team tasks. We use one that helps to keep all of our next actions in one place and it’s been incredibly helpful, especially with us all operating remotely.

What is the one book that you recommend our community should read and why?

Rich Dad, Poor Dad” by Robert Kiyosaki is an absolute classic and one that I’ve read many times. It’s a mindset book disguised as an investment book and it does a great job at stressing the importance of financial literacy and independence – both for your financial health and for your mental health. It’s a simple read, and you can get a lot out of it – to apply immediately to your life.

What is your favorite quote?

“Creativity is intelligence having fun.”

Key Learnings:

• Learn about yourself by consistently training your empathy and putting yourself in the shoes of somebody else.
• It’s only when you have done the work to know yourself fully, that you can begin to actually help others.
• Find your own definition of success and aim for that. Don’t just follow someone else’s definition.
• At the end of the day, you have to enjoy what you’re doing. If you aren’t then make a change. Life is too short to do it any other way.


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