Image of roadsign with question mark on a maze

Hard Questions and Pithy Answers

I was interviewed by Callum Lang and his Enterprize Zone on his podcast and then I was invited to post answers to challenging questions in 100 words or less. Turns out, short answers require more attention than long ones! Here are the questions and answers so far.


What belief do you hold about your industry that is not shared by many?

What has surprised me most as a therapist for professional money managers, active traders, and entrepreneurs is many are not mentally and emotionally prepared for success. The typical pattern is hard work, executing a viable process, and then start making consistent progress. Then something happens. Not a little something, but a big something. They give much of it away in a short period of time. They have stepped out of a familiar context of struggle, one they know they can survive, into an unknown context that shifts their place in the world.

What makes you most optimistic about the future of your industry?

The cultural divide is widening. Personal emotional and intellectual conflicts around politics, money, and wealth are intensifying. Sounds pretty pessimistic! However, where there is emotional intensity, there is an opportunity for people who want to live a joyful life in rapport with their values, beliefs, and behaviors. The coaching and therapy industry can now provide a clear step-by-step path based on how our brain actually works. Using simulations, exercises, private coaching, and group support, personal peace is possible. Our industry has moved from never-ending psychoanalysis to methods that invite new behaviors that serve us better.

What misconception do people outside of your industry hold about it?

As a therapist, coach, and trainer for professional money managers and entrepreneurs, people that are struggling with major issues believe you have to be “broken” to need a coach. This obviously does not apply to physical sports, where you are crazy NOT to have a coach. But in the financial industry, any appearance of weakness is avoided. As a result, capable people outside of our industry often stay stuck in self-created stories that no longer serve them to avoid the risk of appearing weak. This avoidance can limit the options on their life’s menu that increase their power and success.

What coming technological advancement do you expect to have the biggest impact on your business?

As a therapist for professional money managers and entrepreneurs, my goal is to invite my clients to expand their rapport with all parts of themselves and the world they live in. One of the biggest entries to their internal landscape is their physiology. I watch every tick on their face, their breathing, and posture. By expanding these clues, we clarify the various conflicts that keep them from their goals. With more online work, this becomes more challenging. What if my clients had sensors that charted their physiology in real-time while we talked? I could see immediately when we hit a subconscious hot spot.

What do you wish your prospects would understand before they talk to you?

I wish my prospects would understand that our conversations are going to dive below issues, symptoms, behaviors, and even beliefs. Within the first hour, we will be unearthing the driving force behind behaviors that do not serve the client. This process starts with awareness, acceptance, and creating a new foundation to ask what we want. This can only be accomplished with established trust between us and the parts of ourselves that are no longer in rapport with our intentions.

What are your clients really buying? (the feeling beyond the product or service you provide)

Hope. Hope that their future is better than their current state. As a therapist and coach for professional money managers, entrepreneurs, and career-focused people, I get fewer new clients who say that everything is great and they want to make it better and more new clients who feel at the end of their rope. Hope typically consists of an expectation of external events. My clients shift from outcome to process. This shift gives them the feeling of agency over their own lives which, in turn, increases hope. Agency doesn’t change the externals immediately but changes the mindset dramatically.

What skill have you developed since leaving formal education that has been most useful in your career?

The skill from my training at NLP Marin has been by far the most useful in not only my career but my life. NLP (Neuro-Linguistic Programming) started as a set of clinical tools derived empirically from some of the most successful therapeutic innovators. Despite its contentious history, NLP Marin provides a human framework from neuroscience models from the original assorted tools. This framework has made a difference not only in my personal life but how my clients have been able to move from a context of conflict to one of rapport with themselves and their world.

Pitch your business to a complete stranger who knows nothing about your industry:

When asked, I respond. “I work with entrepreneurs, professional money managers, traders, and career people who feel stuck, frustrated, and conflicted about their financial results and success.” LISTEN….LISTEN…LISTEN…I then reflect back on the essence of what I heard. Once they feel heard, they talk more freely and I pay more attention to the process of what they are doing than the content. “It sounds like…… Did I understand correctly? LISTEN…LISTEN…LISTEN. More often than not, this elicits their personal story and concerns. The “pitch” is the process itself, not the sales words.

What would constitute a perfect day for you?

  • Two coaching clients who had an “ah-ha” moment
  • A lively and energetic live group meeting on an issue of money and success
  • Playing with grandkids at a playground, then playing monster for them
  • Romantic dinner with my wife and ……….

Name 3 things you and your best clients have in common:

  • A sense of humor
  • Curiosity
  • Motivation to make the world a better place

What in your business are you most grateful about?

As an author and coach for people who want to expand their money mindset, I get to play with my curiosity and creativity. Without constraints, I can play mindset simulations while jogging or in the shower. I can be playful with clients and test different types of invitations to behavior and beliefs that serve the client better. Without physical constraints, my mind can enjoy an open-ended world of reframing our beliefs and models about the world and our relationship to money.

If you were starting your business from scratch today, what would be the biggest change?

If I look back at my many business ventures, there is one major pattern that repeats itself that hasn’t served me well. As a philosophy major, I tend to think of big ideas, concepts, and a vision for the future. As a result, I had the tendency to plan big and start big. This approach has been hit and miss. I now look at a process of “minimal viable product.” Start small, adapt, communicate with the potential audience, and adapt again. I can still maintain the big vision, and at the same time, stay in contact with the real world.

What have you dreamt of doing for a long time but still haven’t done?

With a background in philosophy and psychology and building a trading firm, I have always wanted to write a book on our relationship and the psychology of money. Well, that is now finished. (“A Private Conversation with Money) What happens after that dream comes true? What happens after we get that promotion, buy the mansion, go public or create wealth? What is interesting to me is the displaced meaning we apply to those accomplishments. If the motivation was to fill a hole in our hearts or meaning in life, what happens if those higher-level needs weren’t filled? Do we create another difficult challenge? Or do we become aware of our deeper desires?

Where will you be in 20 years? What does an average day look like?

I will most likely be in an urn above my wife’s fireplace. On the other hand, the urn could be in the attic under the Christmas decorations. I prefer to think the former, but the latter is more likely. My days look pretty much the same. I have at last attained the ultimate transformation from a conflicted imperfect being to absolute peace. If I could contemplate my pre-urn life, I would feel the satisfaction of remembering only the positive parts of my life…raising a family, business successes, and adventures. Life in the urn is simple and easy.

What is the greatest accomplishment in your life?

Family: Building a family that fixed some of the dysfunction I grew up with.
Business: Starting a series of businesses that gave me a wide range of skills.
Personal: Letting go of the thought that I have the absolute truth and comfort with not knowing.
Mission: Creating a Money-Positive community that builds rapport with money, meaning, and success.

What mistake have you made that you learned the most from?

The biggest mistake is the process of “building it and they will come.” The poster child for this was my vision during the dot com boom. I believed the trading exchange future would be all electronic. I sold my exchange seats and my trading firm, convinced that all trading would migrate to electronic transactions. My prediction was right and early. The industry wasn’t ready yet for my concept and I lost the company during the dot com crash. Now I check myself with the “minimal viable product.” Can I introduce a product that starts with current customer validation?

What is your fondest memory of something that happened in your business?

The fondest memory was “counting the cash.” My first business, while I was still in high school, was blowing glass and sales at fairs across the country. Later it was in shopping malls in the mid-west during the holiday shopping season. Every night, we would have big bags of cash to count. (I date myself because this was before credit cards become ubiquitous). What a pleasure to sort, orient, wrap and count large piles of green dollars, even though I was exhausted every night.

Your business is destroyed, what one thing can never be taken from you?

What can never be taken away is my agency and ability to determine how I experience the business loss. One of the “tells” I look for in my clients is how they ascribe meaning to an event. Where does meaning come from for them? Is meaning packaged with the event? (He made me feel XYZ) Or, does the client have the ability to determine the experience for themselves? (He did XYZ and this is how I choose to experience it.) Developing the powerful agency ability is natural for some, and takes time for others. Start with awareness without judgment. Just notice where your experience originates – externally or internally?

Leave a Comment:

>