Episode 35: Wealth Begins With Self-Awareness with Richard Coyne & Bill Zahller

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In this episode, Dave Wolcott joins the Road Less Travel Show to share the personal journey that shaped his approach to wealth, leadership, and purpose. From growing up in a middle-class household in Connecticut to serving four years in the U.S. Marine Corps, Dave reflects on the lessons of leadership, integrity, and teamwork that stayed with him long after his military service. After transitioning into corporate America, he found himself frustrated by the lack of mission and purpose—until discovering Robert Kiyosaki’s Cashflow Quadrant, a moment that fundamentally changed how he viewed business, investing, and financial freedom.

Dave unpacks how years of running a technology consulting business while investing “underground” in alternative assets ultimately led to the creation of Pantheon and his book, The Holistic Wealth Strategy. He offers practical advice for anyone considering a major career or life pivot, emphasizing the importance of self-awareness, doubling down on your strengths, and building a team to support the areas where you’re not naturally wired. Dave also highlights tools like the Kolbe Index to better understand your instinctive strengths, avoid burnout, and design a path aligned with who you truly are—both in business and in life.

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How’s going everyone and welcome to a special solo series of Wealth Strategy Secrets of the Ultra Wealthy. I’m your host, Dave Wolcott. We get a lot of the same questions from our investors about infinite banking, tax efficiency, asset protection, strategy stacking, and how to actually build wealth outside of Wall Street. And we get it, we know you’re busy. So in this series, I’m breaking down complex wealth strategy topics into short tactical episodes that you can actually use to build legacy wealth. Whether you’re just starting your journey or fine tuning your portfolio, these episodes are designed to give you high impact insights in just a few minutes. So let’s dive in.

I’m your cohost, Richard Coyne. And I’m your cohost, Bill Zahler. On today’s show, we have Dave Wolcott. Dave, we’re so glad you’re here and thanks for joining. Yeah, thanks for the opportunity to be here, connect with the audience and connect with you guys. Absolutely. Yeah. Thank Dave for being on the Roadless Travel Show. Can you tell us a little bit about your former career and how long you were along that path?

Yeah, sure. Well, it’s starting to get a little bit long now, but you know, I like probably many of the listeners was raised in a middle-class family in Connecticut. And I’ll tell you, I can remember to this day, my mother’s voice saying, if you don’t go to school, get good grades, you’re never gonna get into college and get a job, right? And that was really conventional wisdom. So I followed down that path. I went to the George Washington University in DC um and then did the ROTC program. got into the Marine Corps uh after that. that was the opportunity for me to really give back and learn some additional skills that you don’t get in the corporate world really. Things like leadership, uh integrity, teamwork, and things like that. And spent about four years in the Marines, had an awesome time, and grateful to be on the show today. It’s actually Veterans Day. So this is very timely. It’s really a great experience.

And then when I left the Marine Corps, it was interesting because I transitioned into corporate America, which transitioning from the military is actually quite challenging for many folks out there. And I became really frustrated with the lack of uh purpose, the lack of mission that was really in a lot of corporate organizations. that bureaucracy and uh people doing things that weren’t in keeping with having good integrity and such. So I really became very frustrated with that. And then luckily in 2000, I had an opportunity to pick up a copy of Robert Kiyosaki’s Cashflow Quadrant. And that was really a huge light bulb moment for me, right? Coming out of the military, going into corporate and really looking at that cashflow quadrant and understanding that, you you have to be a business owner and an investor if you’re really going to play this game and, you know, succeed in life.

So I forged down that path and created a technology consulting business, ran that for about 13 years, which Richard and I have some roots there, which is really cool. I used to work together as partners there. And then uh all during that time as well, I’ve been investing into alternative assets. So into things like multifamily real estate. But I invested in a lot of different asset classes in the alternative space. And all of this learning, you have to really do what I would call underground. right, especially in the early 2000s, there wasn’t a lot of information out there or resources available. So I was constantly, you know, reading books, listening to podcasts, right, finding information wherever I could.

And eventually, you know, through that, you know, 15 years of really investing in everything, as well as running businesses, um I created Pantheon. which is essentially my business too. You oftentimes entrepreneurs build a business from, which is a business that they know, right? Because they come from some type of background and they transition that. But for me, Pantheon is everything, is really a culmination of all of my experiences and my learnings m and kind of transitioning now into a place where oh I can really help others and really, you know, have a huge, much greater impact on sharing all of these different experiences, different tactics and strategies. And so that’s where we are today. And essentially that’s in the book. We have a book called the Holistic Wealth Strategy came out last year and really encompasses all of uh that experience.

So Dave, what advice would you give somebody who’s considering making a path change?

You know, the first thing is really, it’s all about understanding yourself, Richard, right? The more you can understand yourself. And again, there’s so much conventional wisdom out there, right? Which is, you for instance, we have to be, wear all these hats and do the best we can across like multiple different areas, right? But in reality, in business, right? What you wanna do is double down on your strengths. and what you’re really good at. And then build a team around you for people to do the other things that you don’t like to do or you don’t really do well.

For instance, I don’t like doing projects around the house. So I don’t spend my weekends doing that. If I was gonna spend time, I’d rather be on my business or having quality time with my friends. There’s actually a test that I think is really excellent. nobody has really heard of it before. It’s kind of the foundation of that strategic coach. It’s called Colby, K-O-L-B-E, and you can do colby.com. And you can take this quick 20 minute assessment around your, it’s all around your co-native abilities they talk about, which is essentially your instinctual wiring and how you’re wired.

So for instance, as an entrepreneur, can you take an idea? and completely run with it? Or are you someone who likes to really get into the details, you’re kind of risk averse and things like this. But the more you can really understand about yourself and figuring out any blind spots you have and also just understanding those strengths so that we can be better at what our strengths are. Think about top athletes in the world, right? I mean, if you’re a quarterback, right? All you’re doing is you’re working on your skills in that specific role. You’re not trying to play different roles on the field and practice your kicking, right, on Fridays, things like that, right?

So I think it’s really good advice and we mastermind with our family. And I talked to my kids, have all kind of left college. we talk about this a lot about really understanding yourself and your strengths and then how you can apply that.

Thanks for tuning into our special solo series. If this episode sparked something for you and you’re ready to learn more, head over to holisticwealthstrategy.com and download a free copy of my book. You’ll also get access to our investor community where we share exclusive educational content, new opportunities and resources designed to help you accelerate your path to freedom. And if you wanna take it even further, book a call with our team to learn about our virtual family office services or join our mastermind group where we go deep into building true. generational wealth. I’ll see you on the next episode.