Make The Best Decision Today: Lessons From The Journey Of A Hippie-Raised Entrepreneur With Jason Weiss

“What is the best decision today?” All throughout his journey, Jason Weiss asks himself his question every day. Raised in a family of San Francisco hippies, Jason was used to living in the moment and not worrying too far ahead. In fact, the concept of success as defined in the dictionary is quite strange to him as he is constantly on the move. Jason Duncan follows his journey from backwoods California, to baseball, to bookselling, to being a lawyer involved in politics, to practicing in a firm that exclusively deals with a single famous person’s estate matters, and to being his own boss as the CEO of a company that provides wealth and estate advice to high net worth individuals. Listen in and see how Jason D’s five P’s hold up to Jason W’s colorful entrepreneurial journey. Spoiler alert: the fifth P fits perfectly to Jason W’s story. Listen in.

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Make The Best Decision Today: Lessons From The Journey Of A Hippie-Raised Entrepreneur With Jason Weiss

In this show, we interview the top entrepreneurs in America about how they got to success and how they grow incredible companies. I’ve got this theory that there are five keys to success that every entrepreneur uses to get to success. After years of casually and formally interviewing these successful entrepreneurs, I found out that there are five things that show up every single time. This show was born out of this. Let’s test this theory on camera and on a microphone with some amazingly successful entrepreneurs. Generally speaking, in the show, we only interview people who started their own business, not a family business or franchise. They have about $10 million or more in annual revenue with the business they started and they’ve earned and built a personal net worth of at least $5 million or more.

Our guest fits right within those categories. You’re going to be excited to know his story. He’s a great friend of mine and one of my personal advisors. I love to meet with this guy. I’ll tell you about him in a minute. Let’s talk about where we are. This show is syndicated by the C-Suite Radio Network. It goes out to all of the podcast players. Thank you to the C-Suite Radio Network for syndicating this show. Also, if you’re reading this on the blog only, you’re missing out. You should go and watch this on YouTube because we filmed this live and in-person at The Standard at The Smith House in Nashville, Tennessee, in the Matador Room on the third floor.

This is 18,000 square feet of Southern sophistication and style. It’s one of the top five cigar bars in the country and one of the top steakhouses in Nashville. I’m honored and privileged to be a member here and friends with the proprietor, the one and only, Joshua Sterling Smith, who’s kind enough to let us use the Matador Room for recording these episodes. If you’re in Nashville, you need to hit me up on LinkedIn or Instagram @TheRealJasonDuncan. Maybe we can meet up for a cigar or a nice glass of bourbon here in the Matador Room. Thank you for joining me now.

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I’ve got a special offer. For those of you who are readers of the blog, you can go to I’ve got a special tuition discount for any readers of the blog who wants to enroll as a student at Results University. We have three different levels that you can enroll at depending on what type of experience you want. We’ve got everything from just access to the courses online all the way up to get your very own personal business coach for the entire duration of your experience in the university. We want to thank Results University for sponsoring this episode.

I want to talk about a good friend of mine and a guest who’s sitting across the table from me here at the Matador Room. This guy, born to hippie parents in San Francisco in the ’70s, nominated as a Rhodes Scholar right out of high school. He graduated high school a year early and got drafted right out of high school to be a pitcher for the Colorado Rockies. He got a full baseball scholarship to Stanford University right out of high school, but ended up deciding to go to The University of Oklahoma where he played baseball. He learned how to sell books and went on later to get a Law degree.

He has worked in some amazing firms and worked for other attorneys and judges. He now owns and operates a company that provides advice to people who are high net-worth individuals, executive business owners, etc. We’re going to talk all about that. This guy is Jason Weiss, my good friend. There are two Jason’s on the show now. There’s Jason Weiss and there’s me, The Real Jason Duncan. Jason, thank you for being here.

Likewise, Jason. It’s good to be here.

We’ve known each other for a little while now, but even with some of these details that I dug up for this, I did not know the hippie parent thing in San Francisco. Tell us about that story.

If you go to San Francisco State in the late ’60s, I don’t think you had another choice other than the hippie parents. I still remember it at all. I’ll fast forward. I was in high school. My dad showed me where he grew up and things like that. I went to the Berkeley campus and said, “There’s a sign that says ‘Recycle or die.’ Do they mean that?” He went, “They do.” That was my introduction to the culture back then. They were in the thick of it in the ’60s. My mom intensely dated The Rolling Stones editor at that time. They were true in that culture, hippie parents from the ’60s.

[bctt tweet=”If you can’t explain something simply enough, then you don’t understand it well enough.” username=””]

How did the hippie parents turn out such an amazingly gifted and intelligent kid who could be a Rhodes Scholar nominee, graduated high school early and an amazing athlete, pitcher for the Rockies right of high school? How did that happen?

They looked at things the same way I looked at things now. They looked at things very pragmatically. They didn’t see too far ahead in the future and as hippies “You live in the moment,” so to speak. They didn’t get too far ahead with planning. That’s one of our curses and things. We get too far ahead. We don’t live in the moment and see the moment for what it is. I’ve always had this unique ability to see the moment, not get too far extended, and live and thrive in that space.

When did you first remember playing baseball? That’s a big part of your story.

Again, back when I grew up, there weren’t all these leagues and everything else. After they became hippies in San Francisco, they left the Bay Area. They thought they were going to Oregon. We started driving to Oregon and our car broke down in a place called Grass Valley, California which is near Lake Tahoe. They went, “I guess we should live here.” That’s where I grew up and that’s how I ended up there. We found this acreage five acres, but it was part of a larger subdivision. My brother and I grabbed rocks and threw them to the furthest tree out there and, “Who could hit this tree?” That wasn’t quite baseball, but little did I know it was building my arm strength.

As I got to high school, I started pitching. I wasn’t the most accurate pitcher. Accuracy was not my skill but I had a very strong arm. Again, this the Forrest Gump approach of how I took things. I took one thing after another and the next thing I knew, I started pitching. College coaches started coming out and other sorts of people were coming. Sure enough, that’s what led me to be drafted in my senior year in high school.

Right out of senior high school, you graduated a year early but you got drafted by the Rockies to play plus you got this Stanford scholarship to play baseball. How did you end up making the decision on what to do about all that?

Again, my parents being more of the hippie generation, anti-establishment, if you will. The establishment was never in my purview. I didn’t even apply to a college until late into my senior year. I want to say probably I was graduating when I put my first college application. I thought I was going to a local junior college the whole time because that’s what you do. I got drafted professionally. My high school coach came in and said, “Jason, you’ve got very good grades. We’re talking about the nomination for a Rhodes scholarship. Where are you going to college?” I said, “I was thinking about the junior college down the street.” He said, “Have you thought about a four-year college?” I said, “Not really.” He went, “Can I make a couple of calls for you?” I said, “Sure. Why not? Do whatever you want to do.”

He made a couple of calls. He was calling me to the office in the middle of June. I remember I graduated probably 2 or 3 days. I’ve already graduated from high school and do not know where I’m going. He sat and he goes, “I’ve got two colleges that are very interested in talking to you. Stanford University who wants to offer you a scholarship based on being drafted, your grades and whatnot. The University of Oklahoma wants to take a look at you.” I went, “That sounds great.” He said, “The reason why is they wanted you in the College World Series.”

That meant nothing to me. I said, “First of all, no to Stanford. That’s across the street from me. That’s like going in your backyard. What’s Oklahoma like?” He went, “Let’s take a trip out there.” I’ve never been on an airplane. I’ve never done any of that so I went out to Oklahoma. Sure enough out there, I met Barry Switzer and Brian Bosworth. They happened to be there at the time. I flew home and said to my parents, “I’m choosing education.” They went, “That’s wonderful.” I said, “I’m going to The University of Oklahoma.” That’s how I got to Oklahoma.

In Oklahoma, you’ve got a degree in Law but that didn’t happen necessarily at Oklahoma. You got a degree in Business in Oklahoma. Is that correct?

The first three years of being in Oklahoma is you’re an athlete. I don’t even know if I had a major. If I had a major, it wasn’t something I was majorly majored in. In my junior year, I was still pitching and I got hurt. At that point, baseball and me were having a crossroads. I was hurt and I couldn’t play. At the same point, I want to be a college student. Baseball was done with me, but I happened to be done with baseball, too. Fortunately, we got to go to two College World Series when I was out there. We won a national championship. Baseball had been good to me, but I got to be a senior at The University of Oklahoma, which was fun.

TRAS Jason | The Best Decision Today
The Best Decision Today: Bookselling has all to do with hard work and abilities. Sales abilities significantly translate into entrepreneurship.


How did the bookselling come?

My one year being a college student, because the three years I’ve been a baseball player, I joined the fraternity. I’m going to live four years of college inside one year like, “I’m going to do that.” I did that. I met two college buddies of mine. They said, “What are you doing this summer?” I went, again, “I don’t know.” It was like the junior college thing. Remember, I’m graduating college. They said, “Why don’t you join us to sell books?” “Why not? Where is it?” “It’s at Nashville, Tennessee.” We came out here and I spent the summer selling books in North Carolina. Those two guys I lived with are still very close friends of mine. It’s been a great ride.

Who did you sell books for?

It was Southwestern Book Company. It’s a Nashville icon here in this area.

You and I both know there are so many successful entrepreneurs now in this town and other places. That’s where they got their start. Why do you think that is?

It instills in you work ethic and the ability to accept rejection. I remember this story when I was about to sell books. I was 21 years old. I just graduated. I called my mom and said, “Mom, I think I’m going to go sell books.” You’ve got to remember, hippie generation and all that kind of thing, we never were allowed to answer the door when a solicitor came like, “It’s the establishment who knows us here. We’re not answering the door for it. There are evil people who are knocking on the door.” My mom said, “Don’t go knock on anyone’s door.” I went, “How did the evil person go from knocking on the door to the inside of the door at this point?” It was an interesting thing. Bookselling is all to do about hard work the ability to accept projection.

I think that your sales ability translated into entrepreneurship significantly. I don’t know any successful entrepreneurs who either themselves don’t understand the concepts of sales or have somebody on their immediate leadership team that handles that. Is that your experience as well?

Yes. When it comes to sales, it’s the Einstein line, “If you can’t explain something simply enough, you don’t understand it well enough.” A lot of times, people are selling something they don’t understand it well enough. They haven’t taken the time to understand what exactly they’re selling, whether it’s sales, advice or any of that. Whatever that widget is or services, if you don’t understand it well enough, trust me, you’re going to complicate with your explanation to the client. They’re not going to buy it because people buy things they understand.

You went from your four years of college in one year at Oklahoma in your senior year. Were you selling books that summer leading into that or is it after your senior year?

It was the summer after my senior year.

[bctt tweet=”When you prepare and put yourself in the arena for opportunities, that’s when you get lucky. ” username=””]

You’re selling books. You’re learning how to take rejection. You’re learning how to sell. You’re developing your acumen for handling those types of situations. When did law become a part of your story?

The bookselling ended because it was a summer job. I remember I had graduated college. I was selling books. I did realize early on selling books is not going to be a career. It’s going to be summer. I finished and went back to California. What else am I going to do? I have no job. I’m a college graduate, but I hadn’t thought far enough ahead to, “Maybe I should apply for a job.” Again, it was a progressive approach. I went back and baseball and sports weren’t there, but I still had competitive energy about me. What was going to fill that? I said, “I know what it is, politics. It seems competitive. It seems to fill that need. I’m going to go do that.”

Remember, I just came off the bookselling so I’ve got no fear. I’ll knock on any door and that kind of thing. This was in 1995, 1996. I went in and figured, “Let’s go into the governor of California. That’s the highest level there is.” I went into the governor’s office and this is when you could get to that point. I said to the secretary, “I’m here to see the governor.” The secretary said, “He’s not seeing anybody now.” I said, “That’s fine. I’m going to go sit over in that seat over there and wait for him to free up for a couple of minutes.” The secretary realized I wasn’t much of a threat and said, “He decide to have somebody else come see me.” The person who came to see me was one of his attorneys.

The attorney came over to me and started talking. I explained to him my past and he said, “Why don’t you become an intern for me?” I said, “Great.” I interned for the governor under the legal department. I was in there and said, “Everyone here is an attorney. If I’m going to keep this job, I better become an attorney, too.” There was a local law school there. I applied there and got in. The funny thing about that was you have to take the LSAT to go to law school. I could have gone to any single law school in the country too, but I chose this local law school in Sacramento.

Who was the governor then?

Governor Pete Wilson.

How has that relationship with Governor Wilson?

It was interesting. I had little interaction with him, but he’s got a legal staff of four attorneys at the time. The one who gave me the most tutelage at that time, he wasn’t that much older than me. He was probably 5, 6 years older than me. His dad was Chief Justice of the Supreme Court, which again led me to a lot of connections, which I was going into the work for the governor. They could have put me in the agricultural team, but they put me in the legal team. Through those connections, that grew. That’s where I met a lot of people through the governor.

You ended up getting your Juris Doctorate degree, right?

Yes, that’s correct.

You got your degree. Are you practicing law or you still only work in the political arena as an attorney for the governor’s office?

TRAS Jason | The Best Decision Today
The Best Decision Today: In politics, there is a lot of fun and power, but not enough money.


Once you get into the political arena, it’s the rooms inside of rooms approach. This is a powerful room, but then there’s the room that’s another powerful room. The governor’s office allowed me to get other opportunities. I got to clerk on two different Courts of Appeal, which is a very sought-after position for somebody in law school. I got to work for the United States Attorney’s Office for a period of time. I started not so much in politics but in the political spots that I worked in. When I graduated, I had a good resume and a very good opportunity, but it wasn’t in politics anymore at that point.

Your stint in law didn’t last because you’re not practicing law now. Is that correct?

That’s correct.

How long were you active in the law world as an attorney?

I realized quickly in politics, “A lot of fun and power, they pay you nothing.” I had student loans, all these law school loans and everything else. I was like, “I can be an attorney here for $32,000 or get a job in Silicon Valley, which is during the dot-com burst, and make a lot more money. Which one do I do?” I said, “Forget the altruistic avenue. I’m going to go down and make some money.” I joined a company down in Silicon Valley in 2000, 2001 period time frame. We were responsible for putting video on the internet. I tell them all the time, “My apologies, I’m the root of all evil. I am sorry we did that.” We were at the forefront of all that.

It was an awesome opportunity. They paid me a little bit more of a base salary, but they gave me all kinds of stock options. I was like, “This is awesome. They invest in the next 2 to 3 years. This is going to be great. I’m going to make so much money.” One thing happened around 2001. They called it the bubble burst and companies were laying off. They kept the engineers, coders, and everything else. The 24-year-old attorney said, “We can outsource that guy.” At that point, they said, “Keep your stock options.” My strike price was at eight and the stock was going for four. I said, “The options are worth nothing.” That was my introduction to law, Silicon Valley and the financial process.

Here’s what I like about you. We’ve known each other for a while and I don’t know this story. I know parts of it, but this is very interesting. I think the readers are going to find it interesting as well. Now, you don’t do law and pitch baseballs. You’re certainly not a hippie. What is it that you’re doing now?

I’ll give you the next job I did, which leads me to what I do now. I was in San Francisco and I said, “I’m not part of the Silicon Valley. I’m going to join a law firm.” I joined a law firm. The law firm’s primary client was the estate of Tupac Shakur. Despite what you read, he had passed away. You got to think he had a lot of trademarks and intellectual property out there. We had a bird, dog, and all that stuff. In that role, you would ask a lot of context questions to the estate of what’s going on. Very few were legal questions because you’re just getting the context of things.

What I found out from that experience was, “The average client has seventeen different problems, but I’m legally here to do one.” That didn’t sit well with me because I’m competitive. I want to solve my clients, “Am I going to be an attorney and do the one legal issue you have or the seventeen other problems that you have going on?” I don’t whine my road at that point in my career, “Am I going to be the attorney who’s going to handle the transaction, lease, contract or whatever it is? Am I going to be an advisor who helps with everything else and punt the law stuff?” At that point, I chose to be an advisor. That’s what led to the Symphony.

Your company now is Symphony Advice. Based on the way that I understand it and my interaction with you, you provide advice in all the areas that a high net-worth person, an executive, or a business owner is going to need to know, whether that’s law, accounting, or financial advice, etc. You help pull that together like a symphony conductor. You put all the pieces together in the symphony so that person’s life is taken care of in all those areas. Is that the one?

[bctt tweet=”Never miss little opportunities to say “Thank you” to people.” username=””]

That’s correct. The benefit to me bouncing around so much in my first 25, 30 years of my life was I now have exposure to a lot of different areas. I wasn’t just plugged into an area and say, “This is what you’re going to be,” and then say, “I’m an advisor because of my past.” As I said, my past is dictated by the future, which is I’ve got exposure to a lot of different areas from being in finance, business and law. I now know enough areas to be able to provide advice to all those areas.

The way I like to say it is, “We’re going to give advice in this little window. It’s like we’re going to help a violin player play the violin, but we have no idea if that violin player is off-tune or singing it right with the right song with the rest of the symphony until we get them into the entire symphony.” What try to do for a client, I say, “Whatever you’re doing, let’s see how this makes sense in the entire symphony of whatever you’re doing.”

As a person who’s experienced your services, I can say that it is a refreshing way to take a look at those different aspects. We, entrepreneurs and the readers, suffer through unique circumstances whether it be law, tax issues, or estate planning that the average W-2 employee or the average person out there doesn’t have to suffer through. I can vouch for the way that you bring that together. I think that you’re doing a fantastic job. Let’s talk a little bit about the concept of success. From my experience with you as a friend and as someone who knows what you do personally, you’re very successful and good connector. You know a lot of people and good things. You execute at a high level. I want you to brag on yourself. Do you consider yourself to be successful? If so, why? If not, why not?

When you say the word successful, it gives a connotation, “I’ve reached a certain point.” I don’t ever think I’ve reached anywhere I live at the moment. I don’t say, “I’ve reached anywhere.” Now, I certainly feel blessed in the position I’m in. There’s that, but I still say we’re constantly refining ourselves. I think I’ve had successes. I’ve been successful. That’s my dad and other folks.

The dictionary definition of success is achieving the desired outcome. In some ways, certainly, you’re successful because you have achieved desired outcomes. You wanted to do X and you did X. You wanted to do Y and you did Y. You’re still working towards those things. That’s the cool thing about entrepreneurialism. When you started Symphony Advice, you had a goal. You’ve achieved that goal, but then once you achieved it, you’re like, “I’ve got another goal I want to do and I want another.” That’s the unique plight of an entrepreneur as the goals grow. Have you noticed that in your own story?

Yes. I would say this. The one thing I have learned and I’m very blessed that I was given this quality, which is I knew my talents but I was flexible enough to have life steer in the direction that wanted to steer me. Now very easily, if I put it on a piece of paper, Stanford or Oklahoma, it would not be the choice. If I said, “This job or this job? You would have chosen the other one.” I’m flexible enough to say, in this moment what makes the most sense is without this vision of like, “Twenty years from now, I’ll still be doing this.” I don’t look at it that way. I go, “What is the best decision now? I’ll make the best decision tomorrow and then I’ll make the best decision the next day.”

That’s good advice from the perspective of someone studying success and entrepreneurs. My questions now are going to lead to these five keys that I alluded to in the intro. Every entrepreneur that I’ve interviewed whether formally like this, informally over a cigar, or a glass of whiskey, I asked them questions about, “How did you do that?” For you, how did you build Symphony Advice to be this amazingly successful advising company for people that you serve? What I found is that these five things show up every time. We’ll go through these one at a time.

The first one I find and probably the most important is the concept of passion. When I explain passion, I always have to give some definitions as qualifiers because a lot of times when you say passion, people think, “I have a lot of passion about that or a passion in that. I love that thing.” That is certainly one side of passion. There was probably a time in your past where law or baseball was a passion of yours. When you’re dating, girls were a passion but passion has another side that leads to success.

Passion means the willingness to endure or suffer. For instance, The Passion of the Christ didn’t mean that Jesus was excited to go to the cross joyful looking for it or looking forward to it, but he was willing to suffer and endure for a greater cause. In your story, building Symphony Advice to be a very successful advising firm. Can you tell the readers about how passion is a place where you had to suffer? Can you tell us a little story about how that might have played into your story?

We all know the saying of Malcolm Gladwell, 10,000 hours. It goes along with the Bruce Lee saying, “He’s not worried about somebody who’s practiced 10,000 moves. He’s worried about the person who’s practiced 10,001 certain kicks.” I would say this, “We know the hours, but nobody wants to put in the hours.” If you know that to be true, you’ve got to put in the hours. When you get to 9,000, they didn’t say it’s 9,000 hours. They said it’s 10,000 hours. You’ve got to put in the hours to get there. There’s no shortcut to that. There’s no way around that. That’s when somebody says, “If you can’t explain it simply enough, you don’t understand it well enough.” You know that person hasn’t put in the hours because it’s still confusing.

For you as an advisor, the last guy you met, I don’t know who that is. You’re very private, which is rightfully so in what you do. I have no idea who these people would be. I’m just making this up. The last person that you met with who’s worth gazillions of dollars and you’re helping them figure out all these pieces to the symphony, they’re trying to make beautiful music, too. When did Symphony Advice start? What year?

TRAS Jason | The Best Decision Today
The Best Decision Today: If you are a hundred percent present in the moment, amazing things will come.


It’s 2005.

On 2005, day one out of the gate, shingles hung, business cards are printed, and ink was drawn on the cards. Could you have had a meeting with that guy that day?

Probably because I go back to my bookselling days which my job is to knock on the door and say what I want to say. I wouldn’t have had the confidence I would have had now. You’re right about that. I talked about both sides of the 10,000 hours. I still would have had the confidence. It may not be as successful, granted, but you got to have confidence in what you’re doing.

You went through the suffering part of learning how to go through selling books. I’m sure all the times that people slammed their doors on your face, told you to get off their porch or called you ugly names. That suffering prepared you for what you are going to do later as a professional advisor, right?

Yes, that’s right. I tell people this, too. You’d have to put in the hours, but you’ve got to show up in the arena. I tell them all the time, “Have you been to a play?” They say, “I’ve been to a play.” I go, “Did they get every line right in the play?” They go, “I don’t know.” I go, “It’s because you never script.” I said, “Be willing to knock on the door, cold call, and engage in the meeting. They don’t know the script. They don’t know what you’re supposed to say but you get in there. Give yourself the best. That’s how you get the 10,000 hours.”

Theodore Roosevelt had the very famous comment, “It’s not the critic, but it’s the one who gets in the arena that we applaud.” I butchered the crap out of that, but the readers get the idea. It’s not only passion. It’s the willingness to endure and your willingness to put in the 10,000 hours. By the way, that’s from the Outliers book from Malcolm Gladwell. If you haven’t read any of his stuff, you should go read Malcolm’s. Everything he wrote was fantastic. The second key to success that I’ve found in successful entrepreneurs like you is being at the right place at the right time. For you, I’m thinking back to the story you told a moment ago and correct me if I’m wrong. The right place, right time for you is where the car broke down. Had the car gone all the way to Oregon, this story might not have ever happened the way that it did. Is that the way you see it?

Yes. It’s the old luck definition, which is preparation and opportunity. You can constantly look for opportunities and not be prepared, or you can constantly prepare and never have opportunities. When you prepare and put yourself in the arena for opportunities, you get lucky.

Your right place at the right time was the car broke down in Northern California and you’ve got to set up a shop there. Life started. You were throwing rocks at trees. You became a good pitcher then you went to school. All of those things led to the place where you are now, but then there are other places. The right place at the right time is that you were at Oklahoma and not Stanford. How different is your life now because Oklahoma happened? Would you have gone to sell books had you been at Stanford? Maybe or maybe not. Your story, as much as anybody else’s, there are plenty of places, but there are others that I don’t know about that you can go, “That is a place. I was in the right place at the right time that helped me be successful.”

Let me give you a quick story. This was several years ago. This was my largest client I’ve ever had I’m about to tell you. I wasn’t a great public speaker. I could speak in small groups, but I wasn’t a great public speaker. I wanted to hone my skills a little bit. I was still in California at that time. I said, “I need practice speaking to groups. How am I going to do that?” It was like, “I don’t want to speak to a group because it’ll go bad so I need to practice on a group.” I had this great idea that I’m going to join the Chamber of Commerce, not in my city, but in a city across town like a different city’s chamber. I joined them and they have a luncheon there where people can come for free luncheon and I can speak to them. That’s how I’m going to learn to speak.

I set this free luncheon up. Twenty people showed up. Nineteen of them wanted the free lunch, I’m sure. I talked about whatever I talked about that day. I met a guy in the room. The guy owned at a large engineering firm in the Bay Area. We started doing business. Again, that was my largest client to date. Two years into it, I went back to him and said, “Mike, I know why I was there. Why were you at the Chamber of Commerce luncheon? You’re two hours away from there. Why were you there?” He said, “I didn’t know how to get involved in group meetings. It was the first year and I figured I’d try a Chamber of Commerce in a city I’m not involved in.” I told that story to say, “You got to show up. You got to put in the hours. You got this preparation and opportunity to get decisions like that. There are many of those where it’s the right place at the right time, but it’s because you prepared and put yourself out there.”

Many people misunderstand the concept of networking. What you did that day, a lot of people would misclassify as low-level networking, “Chambers of Commerce are notorious. I have a bad reputation for that.” I have had a very good experience with chambers as a VU for different reasons, but there are a lot of people who look at that and go, “That’s terrible. That’s crappy networking.” The thing is they misunderstand that work is in the word “network.” You have to do something. You did something. You put yourself in a place where it turned into success for you. Had you not been there, it would not happen.

[bctt tweet=”If you ask the right questions, you will get the right answers.” username=””]

I’ll also say this when it comes to that. Check your ego at the door. We used to do this thing, my two buddies at bookselling. We did this dance in the open parking lot. That’s not humiliating. Remember, we’re going to go sell books door-to-door so I don’t know which one is more humiliating. The point being is this if we all don’t check our ego and we think something is too low for us or it doesn’t meet our standards, I never would have been at that Chamber of Commerce. I never would have got my largest client. I never think I’m too good for any room or any situation.

It’s the place where you were being at the Chamber of Commerce meeting, but you put yourself in that place. It was very fascinating. The third P in these 5 Ps of Success is people. Most of the time, everybody can point to a person or persons that had those people or that person not intersected their life, life would be completely different. It’s the George Bailey effect. If you’ve watched the movie, it’s a Wonderful Life, you’ve got this guy named George Bailey who grew up in this little town in Bedford Falls.

He was having a hard time. The little building alone he has is about to go under. It’s going to be called by the bank. He was contemplating suicide and an angel came and said, “Don’t do this. Let me show you what life would be like if you didn’t exist.” It was completely different. The town’s name was different. Is there a George Bailey in your life? Is there a person that you can point to and go, “Had I not met that guy or that woman or have been at this place with these people, I wouldn’t be the success I am now?”

My dad is first on the list, but I’ll give you a second story. I was a little boy. I was eight years old. I’m going to make a number, something like 8, 9, 10. My dad would take me once a year to a baseball game. We went down to watch the San Francisco Giants play at Candlestick Park. I’d get right to the room and I make him be there five hours early or whatever because we’ve got to go one game. We were there early in the game. I was on the railing. I saw a guy named Dusty Baker out there. I think it was at the end of his career at this point. I yelled to him, “Mr. Baker.” He came over and I wanted him to sign something. He took his batting gloves off he was wearing, signed those, and gave me those. He was amazing.

I was a little boy. I went back to my seat and sat down. My dad said, “Do you know what you do for somebody who does something nice?” I went, “What’s that?” He went, “You write him a thank you note.” I went, “Okay.” I went home. I was 8 or 9 years old. This was in 1981, 1982. I wrote to San Francisco Giants, “Dusty Baker, thank you very much for signing these batting gloves. San Francisco, California.” I had no address. I sent it off. About a month or two months later, the phone rang. My mom said, “Jason, the phone is for you.”

I got the phone. It was Dusty Baker talking to me about, “Thank you for the notes. You’re welcome.” I didn’t say a word, but he was probably like, “Are you going to say something?” I was stunned. Long story short was Dusty called me about every month. He’s one of my closest friends to this day. The point is, “Never miss these little opportunities to say thank you to people.” With Dusty, he recognized a young man. He recognized somebody and he poured into me. Dad told me, “When you meet people, pour into them. You don’t know what that means to that person.” That story always stuck with me.

I remember you telling me a part of that story at some time in the past and you were the person who introduced me to Dusty. I remember talking to him on the phone one time and going, “I can’t believe I’m talking to Dusty Baker.” That’s phenomenal. That’s a great story. You said dad was first and I see dad in that story where he did that. Is there something else about your dad that helped get you to where you are besides how you got to send that thank you note?

My dad still has an incredible ability to prioritize things. He knew that his marriage was first. He knew kids. He knew where is business ranked. I’ll tell you a story. This was several years ago. I had an office very close to my house. During the day, Mike, my wife, and the two kids would come over and see me at the office. I’d play around with them. It was awesome to see the kids. Work would get over and then I’d go home. I’d see them checking up on work, email and things like that. I thought, “When I’m at work, I’m distracted. When I’m home, I’m distracted. This makes no sense. My dad would never do this.” I came up with the thing that my dad would always say, “Be 100% present 100% of the time.” I think a lot of things is if we are 100% present, not lukewarm in the moment, but 100% present 100% of the time, amazing things can be done.

I can say as someone who knows you, that is in fact of who you are. Your dad has instilled that very successfully in you. The fourth P of Success that I talk about is preparation. The way I mean it is that you got to be prepared and have the know-how to pull off what it is you’re going to do. For example, you are now an advisor to some powerful and wealthy individuals and executives. You do a very good job of helping them in some sensitive areas of their life. They’re not going to hire just any dude who calls them and shows up. No matter how persistent they are, they’re not going to hire anybody to do that because you’re looking into some very personal things, financials, estate planning, which gets into a lot of private areas. How did you prepare to become the successful advisor that you are now?

It started early on when I was an attorney. I was in law firms. When I was still a law student, I was in the litigation department. The head litigator asked me. He went, “How would you approach a deposition?” I went, “I don’t know. How should I approach a deposition?” He went, “What would you say?” I said, “That’s the guy if he did it.” He went, “You wouldn’t do that. Would you ask him his name?” He went, “I tell you what. When you go on a date, do you ask the person to marry? Is that your first question, ‘Will you marry me?’ or do you get to know them?” I said, “Yes, I get to know them.” He said, “In asking questions, there’s an arc in a story to asking questions. If you ask one question at the beginning of the conversation and he asked that same question at the end, you might get two different answers.”

If you can understand the ability to ask questions like a deposition, you’ll be very successful in garnering information. What I practice and hone and prided myself in is the ability to ask the right questions to people. If you get the right questions, you’ll get answers and it’ll reveal things that they weren’t normally going to do. Based on that, trust can be developed. If you just ask people constantly, “How are you doing now?” You’re only going to get skin-deep. That person will never trust you because you’re at skin level. It’s the ability to ask good questions to get into know the person who garners trust in them and you.

TRAS Jason | The Best Decision Today
The Best Decision Today: People will invest in you when they have a really clear idea of what you’re doing.


I 100% believe that better questions lead to better answers. You’re never going to know what you want to know if you don’t learn how to ask questions. I see that in you and I completely get that’s what’s led to the success.

People always said to me, “How do I get to the questions?” I said, “Whatever question you want to ask, go three years back in that story.” If you wanted to say, “How did you become Symphony Advice?” you don’t just ask them how they got there. You say, “What were the years leading up to that?” We so badly want to know the answer to our question. We want to ask, but we forget the groundwork and foundation that need to be laid prior to that question.

The fifth P to this idea that I’ve got this theory about these 5 Ps of Success is plan. Most of the time, when I mentioned that without any explanation, people immediately think I mean business plan. They may say, “When I started Symphony Advice several years ago, I wrote a business plan.” That may or may not have contributed to the success of many people’s stories, but more often than not, I found that most successful entrepreneurs I know don’t have written business plans. What I mean by plan when I mention plan is I’m talking about financial resources. I’m talking about specifically the ability to obtain and deploy those resources so that you can be successful.

As an advisor, your need for resources is ongoing supporting costs of staying in business. You don’t have a cost of goods sold. You don’t have a product necessarily that your product you had to create to sell. You’ve got intellectual things that you’re sharing with people and connecting. It may or may not have required a ton of resources for you to start. Tell us what plan did you have to obtain resources to get Symphony Advice off the ground and be successful?

You got to have a clear idea of where you’re going and what you’re good at. People will invest and give you resources when they have a clear idea of what you’re doing. It’s like anything else. I take it always to the dating principle. If you are somebody who’s acting like somebody you’re not, nobody will want to marry you. It’s when you become to act like the person you are that people will find interest in you. That’s the principle you need to do. It’s when you become clear about who you are, where you’re going, and what you’re good at, then people will come and ask for resources. You’re not the if you’re not the You don’t need the neon sofa and everything if that’s not you. Be who you are and people will find you out.

If an entrepreneur is sitting down with you and they’re saying, “Jason, I’m starting out. I know you’re an advisor to these high net-worth people. These entrepreneurs are already successful. They’re making a lot of money, but I’m just getting started.” What piece of advice or couple of pieces of advice would you give to that person starting out knowing what you know now as a successful entrepreneur?

What do you do well? What do you do better than anyone else? Let’s have a narrative around that. I’ve got people wanting to buy window washing companies, “If you’re the best window washer, we want to have a conversation with you.” I have people who are involved in sheet metal, restaurants and hotels. What are you good at? They all want to buy what you’re good at, but the problem is, if you don’t know what you’re good at, how are they supposed to find that out for you?

What if somebody says, “I don’t know.” What do you do with that?

Ask people around you who you trust. I’ll say this in a different direction. I have a client who invests. They will always ask me, “Did you invest?” They don’t do due diligence. They’ve got a couple of trusted people and they will say, “Did you invest?” If they invest, they’ll invest. The point being is this. You may not know what you’re good at. Find the people who know you best. They’ll tell you what you’re good at.

Not everybody who sits across the table for me do I know as well as I think I know you, but I’ve learned so much now in our conversation that I didn’t know. This is for your own edification. I may say all this and you go, “I don’t want that in there.” I’m going to tell you. You are such an impressive person. I’m not blowing smoke here. When you and I met, we were sitting at a table at a breakfast. It was a networking breakfast that we were at. Again, it goes back to networking, right place at the right time. Not only were you at the right place at the right time and was I, but we also, hopefully, we’re the right people for each other for different parts of our lives. You handed me your business card. We were talking and it said Symphony on it. I thought you were with The Symphony here in Nashville. You were like, “No.” You explained it.

That led to a coffee meeting at Starbucks. I happened to be studying about some particular investing things and you started asking me questions. I can honestly say this. My life is at a different place because I know Jason Weiss had we not met that day at that networking. I don’t know if it’s as dramatic as you meeting that guy at that chamber thing, but I think that it might be because you’ve introduced me to so many amazing people. You’ve helped me do so many amazing things in my own life. I’m saying this for the benefit of the readers and for you. I want you to know how much I appreciate you. I don’t think I’ve told you that enough and now I’m doing it publicly. Knowing this story makes me even more impressed. You’re a very impressive individual. I knew you were successful, but now, I get a lot better picture. I hope the readers are appreciating this. How can readers get in touch with Jason Weiss?

[bctt tweet=”If you don’t know what you’re good at, find the people who know you best. They will tell you what it is.” username=””]

I believe we have a link through our website. The best way to get through to me is our Contact Us pages there.

That’s You can go to his website. You can log in there. If there’s a contact, you can reach out to Jason that way. He doesn’t participate in all other social media. He’s way too busy of a man to not be distracted by those other things. He’s got too much else going on with his family and all the other stuff that’s happening. Jason, is there anything that I didn’t ask or something you wanted to say specifically in regards to success or anything else?

No, but I would say this. Whenever you start a business, it seems like the elephant is in front of you. You’ve got so much to do, but remember that famous line, “It’s just one bite.” How do you eat an elephant? One bite at a time? That’s even for people with so much going on. I say this to my wife and three little kids, “We’re not going to solve everything now, but if we can solve one thing and take the elephant with one bite, we’ll get there eventually.”

There you have it, everybody. We’ve looked at yet another successful entrepreneur. Jason Weiss has given us his story about how these 5 Ps have played a part in his story of success as a Colorado Rockies, Oklahoma baseball pitcher, a bookseller, an attorney, a law clerk, and now as the proprietor, CEO and Founder of Symphony Advice, working as an advisor for a lot of amazing people. His success story started with passion. There was a right place at the right time. There were the right people in his story. He prepared well and he had a plan.

If you are interested in knowing how you can be successful like Jason and the other guests have been, there is a way to understand that probability. It is through The 5 Ps of Success Assessment. You can get this and download it for free on my website at It’s 100% free. When you complete the assessment, it’ll give you a personalized report that gives you your odds or probability of success with regard to a specific venture. You’ll have to fill out what your venture is and what you’re trying to accomplish.

Here’s what people tell me when they take the assessment. They say, “If it comes back with low probability, what does that mean?” Here’s what that means. That doesn’t mean you can’t be successful. It means that thing that you’re in might not work. It’s like what Jason Weiss said, “Find out what you’re good at.” You may have a great idea, but you don’t have the ability to execute it. The 5 Ps of Success Assessment will help you identify that. In like manner, it’s going to tell you what you shouldn’t pursue, but it also helps you get clarity on what you should pursue. Go to and download that assessment.

Occasionally, about once every six weeks or so, I do a five-day challenge with anybody who wants to sign up for that. That does cost a little bit of money. That five-day challenge is five back-to-back days with a whole group of people where we go through not only that assessment, but we dive deeper into the concepts of the 5 Ps so that you know how to apply those to your life as an entrepreneur and a business leader. I want to thank the C-Suite Network for syndicating this. I want to thank you too, Joshua Sterling Smith and The Standard here in Nashville for hosting us here in the Matador Room. This has been another fantastic episode with me, the Real Jason Duncan. I will see you on the next episode. Until then, remember, Jesus is King.

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