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  • Grow Your Network: Dr. Preston Cherry Is A Psychology-Powered Wealth Builder

Grow Your Network: Dr. Preston Cherry Is A Psychology-Powered Wealth Builder

HOW and WHY to connect with Preston

For years, I've been connecting with interesting people and documenting insights that might help my clients and myself. What was once private is now (mostly) public.

People often ask: "How do you know all these people?" and "How do you connect these (re: random) ideas?" The answer is simple: consistent relationship cultivation and thoughtful note taking. My north star is trusting my instincts, my maps are the constellations in these reflections.

This approach to multidisciplinary networking has helped dozens of clients, colleagues, and friends strengthen their networks and unlock new opportunities. Find my Personal Archive on CultishCreative.com, watch me build a better Personal Network on the Cultish Creative YouTube channel, and listen to Just Press Record on Spotify or Apple Podcasts, and follow me on social media (LinkedIn and X) - now distributed by Epsilon Theory.

You can also check out my work as Managing Director at Sunpointe, as a host on top investment YouTube channel Excess Returns, and as Senior Editor at Perscient.

Feel free to steal these ideas directly - that's what they're for! I can't promise you'll learn FROM me, but I guarantee you can learn something WITH me. Let's go. Count it off: 1-2-3-4!

Introducing... Dr. Preston Cherry!

Do you know Dr. Preston Cherry? He's the founder and president of Concurrent, author of "Wealth in the Key of Life," and someone who brings the psychology behind every financial decision into sharp focus.

If not, allow me to introduce you. He's a master at helping people understand the emotional and psychological drivers behind their money choices, combining behavioral finance with practical wealth-building strategies. I wanted to connect with him because he embodies something I value deeply: the courage to look in the mirror and do the honest self-work that leads to real transformation.

Our conversation is LIVE now on the Just Press Record YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear him break down the psychology of fear, rejection, and why most people need permission when they should be giving themselves courage.

THREE: That's The Magic Number of Lessons

In the meantime, I wanted to pull THREE KEY LESSONS from my time with Dr. Preston Cherry to share with you (and drop into my Personal Archive).

Read on and you'll find a quote with a lesson and a reflection you can Take to work with you, Bring home with you, and Leave behind with your legacy.

WORK: The Daily Self-Coaching Reality Check

"I do have to pump myself up every day. Everybody thinks that I'm like so extrovert all the time... but I do, and it's actually self coaching every morning because, you know, I don't want to hear the no."

-Dr. Preston Cherry, Just Press Record on Cultish Creative YouTube

Key Concept: Even the most confident-appearing professionals have to work at confidence daily. Dr. Cherry reveals that behind every bold exterior is often a disciplined practice of internal preparation. The difference between successful people and others isn't the absence of fear or self-doubt - it's the commitment to showing up and doing the work of self-coaching regardless of how they feel.

Personal Archive Note-To-Self: Everybody is just a regular person. I try to tell myself that a lot. I know it, but sometimes I just have to remember it.

Their lives or lifestyles may be miles or even lightyears from mine. Their accumulated experiences or bank accounts too. But, they woke up this morning and put their pants on one leg at a time too.

The last sip of coffee and a little music is a big one for me. It’s the final pep talk. The music choice comes down to the tone for the day. The difference between Fugazi days and Freddie Gibbs days, as one example, boils down to how much “everyman is in this with me” energy I need to start with, versus the “I will out-hustle the living universe in the next 20 minutes” vibes. Or, take Sturgill Simpson versus Charlie XCX days, those divide up into “let’s get philosophical where nobody else is expecting it,” as opposed to “this is not my life, that is not your life, but you are entranced by the multitudes in the universe it apparently contains.”

The point is, the music helps transfer the confidence of others into my own self-starting. I don't usually say it out loud to others (well, my wife hears about it, sometimes my dogs too), but Preston's honesty made me want to share it

Work question for you: What daily self-coaching routine could you establish to prepare yourself mentally for the challenges and rejections that come with pursuing your professional goals?

LIFE: The Mirror As Your Most Honest Advisor

"The mirror is an expensive audit or a wonderful audit. Either way, it helps us overcome these imperfections... and we gotta polish ourselves up in the mirror."

-Dr. Preston Cherry, Just Press Record on Cultish Creative YouTube

Key Concept: Self-awareness isn't just a nice-to-have personality trait - it's the foundation of all personal growth. Dr. Cherry's "emotional HSA" (Honest Self Audit) framework recognizes that we can't improve what we won't acknowledge. The mirror doesn't lie, and neither should we when we're looking at our own patterns, behaviors, and areas for growth.

Personal Archive Note-To-Self: In therapy, I learned to ask, “What am I feeling right now and should I harness it or let it go?” I don’t bring that thought into my mind enough. The emotional HSA is a reminder of the question.

The patterns and habits all start with an emotional trigger. They start with a “when this happens, that follows” approach. They’ll break you, if you let them.

And you don’t even need to change all the patterns. For the most part, you just have to recognize them. On the days when I ask, “How am I complicit in creating the things I say I don’t want,” I do the audit. I still do this often. I don’t always make progress on those days, but my framing is improved. It’s worth noticing it, because I know my chances of being better are there, if I’m noticing it.

Life Question For You: When you look in the mirror - literally and figuratively - what patterns or habits do you see that you've been avoiding addressing, and what would change if you stopped avoiding them?

LEGACY: Session Work Builds Superstars

"Most people work for somebody... sometimes you're not building somebody else's dream. You're doing that session work to build your dream... Michael Jackson was in the basement, you know, Motown... that man was 22 years old. So he had all this session work to hone in on the craft and then you can go be great."

-Dr. Preston Cherry, Just Press Record on Cultish Creative YouTube

Key Concept: The apprenticeship phase isn't wasted time - it's preparation for mastery. Dr. Cherry reminds us that even legends like Michael Jackson spent years learning, watching, and developing their craft before they could command the stage. Every "session" in your career, even the unglamorous ones, is building the foundation for your eventual breakthrough.

Personal Archive Note-To-Self: What I love about this idea, of apprenticeship, is it shows up at multiple phases in life. When we’re young, we’re looking for the people to learn under. It’s a myth that they’ll just find us. It’s a fact, and one I learned the hard way, that people can lord paths over you and put you in a faux-apprenticeship positions, without apprenticing anything because you’re too trusting.

So, the world is mean sometimes, you know? And you can learn from those lessons. You can go out and be an apprentice. You can, and should, once you have skills - become a person who finds others to apprentice under them, for the right reasons.

Had I not had the experiences I had, I don’t know if I’d be as aware or feel as strongly about this idea as I do. Knowing greatness can come out of it, as Preston reminded me with (re: Michael Jackson), is a wonderful thing. Nobody is great alone - it always takes a village.

Legacy question for you: How are you treating your current role as "session work" that's preparing you for something greater, and what skills are you honing now that will serve your bigger vision later?

BEFORE YOU GO: Be sure to...

You have a Personal Network and a Personal Archive just waiting for you to build them up stronger. Look at your work, look at your life, and look at your legacy - and then, start small in each category. Today it's one person and one reflection. Tomorrow? Who knows what connections you'll create.

Last thing: Don't forget to click reply/click here and tell me who you're adding to your network and why! Plus, if you already have your own Personal Archive too, let me know, I'm creating a database.