Interview with Chad Willardson
How to Build Wealth Without Sacrificing Your Family with Chad Willardson
You set out to build wealth, then realized your family was getting the leftovers.
But it doesn’t have to be either-or, you can thrive in both.
Today, I’m talking with Chad Willardson—wealth advisor to 8 & 9-figure founders, serial entrepreneur, bestselling author, and father of five—who’s figured out how to scale his wealth and stay fully present for his family. He runs a successful wealth advisory firm, owns multiple businesses, travels by private jet, and still makes it to his kids’ games.
In this conversation, Chad reveals the exact frameworks he uses to buy back time, build lasting wealth, and prioritize what matters most—insights he expands on in his upcoming book, Fully Invested: Why Work-Life Balance Is a Total Lie.
You’ll learn how he structures investments, leverages debt without stress, and designs a calendar around his life, not just his work.
In this episode, you’ll learn:
✅The habits and systems Chad uses to prioritize family without sacrificing growth
✅The “buy, borrow, die” strategy that Chad uses to grow his wealth tax-free
✅The real cost (and benefit) of buying a private jet
✅The “Right Brain / Left Brain” executive assistant system that saved his time and sanity
Featured on This Episode: Chad Willardson
✅ What he does: Chad Willardson, CFF®, CRPC®, AWMA®, is the President and Founder of Pacific Capital, a family office services firm dedicated to helping high-net-worth entrepreneurs achieve lifestyle and financial freedom. Chad is also the Founder of Platinum Elevated, an exclusive coaching program for growth-focused entrepreneurs. As an elected City Treasurer managing $650 million for taxpayers, Chad brings unparalleled expertise in wealth management, cash flow strategies, and business growth. Beyond his professional achievements, Chad is deeply invested in his family and previously hosted The Smart Money Parenting Show, ranked the #2 podcast on Apple for Parenting, Kids & Family, where he shares actionable advice on raising money-smart kids and balancing success at work and home. With over 20 years of experience in wealth management, Chad continues to inspire entrepreneurs to win in business and at home.
💬 Words of wisdom: “I want to succeed big in business and at home—not either or.” – Chad Willardson
🔎 Where to find Chad Willardson: LinkedIn | Instagram | Amazon
Key Takeaways with Chad Willardson
- Chad’s Unorthodox Exit from Merrill Lynch
- The Financial Advisor Who Thinks Like an Entrepreneur
- Why He Walked Away from 75% of Clients
- How Chad Grew a $230M City Fund to $650M
- How Chad Builds His Own Portfolio
- Buy, Borrow, Die: Chad’s Wealth Building Strategy
- Chad’s Take on Crypto and Managing Risk
- Building Systems and People to Scale Freedom
- The Right Brain Left Brain EA System
- Is Flying Private Ever Worth the Cost?
- Is It Possible to Win at Work and at Home?
- Who’s in Your Inner Circle?
- Want to Know Your Real Priorities? Check Your Calendar
- Before You Invest Another Dollar, Ask This
- Why Most Financial Advisors Fail Entrepreneurs
Why Most Financial Advisors Fail Entrepreneurs
Inspiring Quotes
- “If you have great people and they’re trained well and they’re bought into your vision and mission, they’re loyal, they’re ethical, and they’re great at what they do, then the sky’s the limit for everyone. And when we grow, they grow.” – Chad Willardson
- “If you are an entrepreneur, you should be taking advice from entrepreneurs who understand your brain, your DNA, how you’re wired differently. Traditional financial advisors don’t understand entrepreneurs because they aren’t one.” – Chad Willardson
Resources
- Pacific Capital
- Pacific Capital on LinkedIn | Instagram | YouTube
- Chad Willardson
- Chad Willardson on LinkedIn | Instagram | Amazon
- Fully Invested: Why Work-Life Balance Is a Total Lie
- Wealth Wired Differently: 7 Advantages Entrepreneurs Miss Out on When Taking Financial Advice from Non-Entrepreneurs by Chad Willardson
- John Ruhlin
- Brad Lomenick
- Strategic Coach
- Dan Sullivan
- Free Zone Frontier
- Jerry Maguire
- Pareto Talent
- BELAY
- Nik Tarascio
- Warren Buffett
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Read the Full Transcript with Chad Willardson
Justin Donald: What’s up, Chad? Good to have you on the show.
Chad Willardson: Hey, thank you so much for having me on. This is awesome.
Justin Donald: This is fun. We’ve talked about it for a little while. I’m glad we could make it finally happen and after hanging out at a ton of events, I’ve been wanting to tell your story. And I first got a chance, I mean, I’d heard of you a bunch because we have a ton of mutual friends, the late John Ruhlin being one of them. But we just share so many mutual friends. And then we went to, let’s see, Brad Lomenick hosts a bunch of cool stuff from change agents to young guns to the family reunion gathering. And so, we hung out, I think, it was at change agents.
And then most recently, we’ve had a chance to cross paths a few times at Strategic Coach with Dan Sullivan, kind of their highest ticket mastermind, Free Zone Frontier. And I know you’re a huge supporter there. You speak on stage there and educate that community a lot, which is a very similar community, a very similar avatar to the Lifestyle Investor Mastermind. In fact, we’ve had several members from Free Zone Frontier, from Strategic Coach come in and join. And we had someone that just recently applied who is definitely playing the game of business and life at a high level. So, I’m excited about that.
Chad Willardson: And unbeknownst to you, yesterday morning, I was in a sauna in Utah. And I don’t know how the conversation came up, but someone in the sauna was like, “Oh, Chad, I read your stuff on LinkedIn. I know you don’t know me.” And he went through a couple cool things and then he said, “I think there’s someone I really would like to introduce you to. His name is Justin Donald.” He goes, “I really think you guys would click. I think you guys have a lot in common.” And I’m like, “You know what’s funny?” I said, “I think I’m going to be on his podcast show tomorrow afternoon.” And he was like, “What? Oh, my gosh.” And I should know his name, but it was a brief conversation in a sauna. He’s in Lifestyle Investor though. He is a member.
Justin Donald: Okay. It could be John Rampton.
Chad Willardson: He’s a doctor. I’m 100% certain he is a doctor who has maybe sold part of his practice. It had to do with dental or ortho or something. But he’s in your group for sure because he was talking it up big time.
Justin Donald: Love it. Well, it’s a fantastic community of people. We actually have a good number of medical professionals. It could have been Paresh. We probably have 10 to 15, maybe even stretch into 20 medical professionals that have had some sort of an exit, either full or partial over the last five to seven years.
Chad Willardson: That’s cool.
Justin Donald: Well, I’m excited to tell your story. I mean, you have all the accolades, you have all the abbreviations next to your name. I mean, basically, everything you can do in the financial world, you have schooling and education around it. You’ve been in wealth management and financial services for over 20 years, so you know the space, but you do it differently than a lot of the other financial gurus out there or money managers out there. And so, I want to highlight some of the cool things you do, but I also want to tell your story.
You have been helping ultra-high net worth individuals for quite some time. You’ve built up a very big practice. You sold that practice not too long ago. You’ve pivoted, you have some really cool coaching programs you do. So, let’s dig in. I want to know where it all got started and any of the details you can share on the exit, we’d love to know because that’s kind of our name and game. We do a lot of that inside our community.
Chad Willardson: Yeah. So, I started in wealth management directly out of college, so it’s been a while. I did an internship for my cousin who was a mutual fund manager at the time. I remember when I was in high school, my dad would cut out like Wall Street Journal clippings and he was on Fortune magazine and all this cool stuff, and I looked up to my cousin a lot. And so, when I was in college, I said, “Hey, can I do an internship and just shadow you? I’ll just do whatever you need me to do.” And I got to take notes. This is back in the day before AI note taking. So, I was taking notes.
Justin Donald: Real notes.
Chad Willardson: And real notes on all of his conference calls with companies that he was buying for his fund. And I got to do a lot of the stock chart analysis with him in his office, just a lot of the research stuff that an intern would do, but I really enjoyed it. And so, as soon as I graduated college, I immediately took a job opportunity at Merrill Lynch Wealth Management, spent nine years there, and decided to go out on my own and start all over.
Justin Donald: Smart move.
Chad Willardson: And that’s when I started Pacific Capital. Yeah, became an entrepreneur.
Justin Donald: Strategic for you. Yeah, it’s hard. A true entrepreneur cannot be caged in. And so, when you’re working for someone else and you just have the itch, oh, you just got to take the shot. You got to take the chance and see what happens because otherwise, you’re just always going to wonder. And in your case, you built quite the practice.
Chad Willardson: Yeah, it was like Jerry Maguire, where essentially, I walked out with my assistant and my boxes and said, “I’m out of here,” on a Monday morning. I was just like, “I can’t take this anymore.” And it was during, I guess, the Great Recession of banks and Wall Street, investment companies merging, and all this stuff. And so, Bank of America bought Merrill Lynch and it was not fun to work in that environment anymore. I felt like I was at the DMV. And if you’re familiar with the California DMV, it’s not a place you want to work, so…
Justin Donald: Well, one thing that is certain, it’s like, there’s nothing wrong with living inside of corporate America.
Chad Willardson: No.
Justin Donald: Unless you know that your time has come to an end, like that season can serve a lot of people. When you know the time is done, you got to move on. Life’s too short.
Chad Willardson: Yeah, I’m not someone that is great at just coloring within the lines, and so, I was never good at homework. I always questioned, couldn’t there be a better way? I was in school and I always thought like, I think we did an hour of productive work in this seven and a half hours I was in class, and it just was like, this doesn’t make sense to me. I know everyone else thinks like this is the track we got to go on, but I never felt, like I was doing what I should be doing when I was just sitting there listening to lectures all the time. So, eventually, it was inevitable.
Justin Donald: Yeah, a lot of people, it’s like the longer you’ve been in, the more they feel handcuffed to it because it’s like I’ve served my time, I’ve moved up the corporate ladder. I have a new title or a new designation. I’ve been given more territory or accounts. I have these big-name companies, and it can be hard to walk away from that.
Chad Willardson: Yeah, it was scary. Most of my inner circle thought it was a bad move. I had a big corner office and Merrill Lynch would fly me around as their poster child and have me speak to audiences and stuff. And they’d have the big commercials on TV. And so, how was I going to compete with these big brand companies? And so, it was definitely scary. I was 32 with three kids, soon to be five kids, and I was starting all over.
Justin Donald: Yeah. So, I know some of your differentiation. I’d love for you to explain it in your words, but like, as I see it, you stand for something different in the world of financial services. And so, in that world, I feel like you have a lot of people, and by the way, I think financial services can be great for many people. I don’t think they’re great for all of your net worth, like a lot of people do, but I think you have a lot of people that recommend products that they themselves don’t invest in. And then from a performance standpoint, you have the vast majority, 95% plus, that don’t outperform the index, right? And that was over a 15-year period of time, over a 30-year period of time, it’s less than 1%.
Now, you happen to be part of the 1%, and I think part of what’s nice for you is you appeal to lifestyle, which resonates deeply with me. You appeal to family and making decisions that are best for the family, when maybe that’s not the best financial on paper decision, but it’s the best overall return. And then you’re big on financial freedom, which I think is hard to find in your industry.
Chad Willardson: Yeah. I think that my industry is a sea of sameness. I don’t fit in at all. I’m an absolute misfit when I go to the conferences. Some people maybe don’t wear a suit these days, but I’ve not been wearing a suit to these things for 10 years. I always stand out, but I just believe differently. Financial advisors typically just recommend the stock market and nothing else and they really are against real estate often, they’re against private investments. And forget talking about tax stuff or forget talking about cryptocurrency. They won’t touch it with a 10-foot pole. And I appeal more to the open-minded entrepreneur because I am one. That’s what I am. So, I’m more of a peer to our clients than I am a financial advisor in a big corporation. I’m more their brainstorming partner and I talk to them about their big ideas. And I’m not opposed to saying, hey, let’s look at other options for investments. And you don’t need to have 100% of your money in the stock market. So, I’m a big fan of the stock market, but I’m just more open and objective. And I’m also an entrepreneur. I’ve founded multiple companies. And so, we can talk as peers to our entrepreneurial clients and not where they have that language barrier between financial professional and entrepreneur, where they’re not in sync and they don’t feel understood at all.
Justin Donald: Yep. Yeah, that makes a lot of sense. And for me, I study asset allocations of single-family offices, so that’s the billionaire class. And the newest UBS report came out. JP Morgan’s report is going to come out any day now. Goldman’s report is going to come out. And I love looking at these. And then there’s the separate groups that kind of aggregate all these single-family office data. And it is very clear, every single year, and we’re seeing a trend that alternative investments continue to increase in total percentage allocation. So, generally, in the financial services space, I see a lot of people that don’t want to let go of the dollars that they’re managing because they get paid on assets under management even though the wealthiest people in the world are generally somewhere between 50% and 60% of their net worth in alternative investments, like private equity, private credit, and real estate, among other things.
Chad Willardson: Yeah, a little bit of bias in our industry, I would say.
Justin Donald: Yeah. Well, I love that you do it differently. And recently, I mean, within the last few years, you were able to sell that practice. I would imagine that it’s…
Chad Willardson: Yeah. So, I basically sold a portion of it, which is the– we’ve been ratcheting up our floor of the clients we serve. So, I didn’t sell the business, but I essentially transitioned 75% of our clients in the business, and those are the clients that aren’t entrepreneurs with at least $25 million invested in their investment accounts with us. So, we’re actively working with our high-end entrepreneur clients and we’re building with those types of new clientele. And then the legacy clients that were sub 25 million, we’ve found a great partnership firm to handle and work with those.
Justin Donald: I love it. Now, here’s the thing, you live a great life. You have a beautiful family.
Chad Willardson: Thank you.
Justin Donald: You always show your pictures of your family and I feel like you guys are you know GQ cover of whatever. I mean, you guys…
Chad Willardson: I don’t know about that, but thank you.
Justin Donald: Wonderful family. You live a killer life. You fly private. You travel to really cool exotic places. I mean, you’ve built this incredible lifestyle. You had an exit big enough that you could just walk away, as my understanding. So, why are you still continuing with this upper tier, this high-net worth tier over $25 million? You could just be done, so why?
Chad Willardson: Yeah, I love what I do. I love the people I work with. It stimulates growth. I’m relentless on growth, and so, my primary business is Pacific Capital. That’s wealth management, family office services for those entrepreneurs. Secondary business is sports. I have a sports complex. We’re opening up another sports complex in LA and we own travel volleyball teams for club volleyball and travel basketball for AAU. And so, we host Nike and Adidas tournaments every weekend. And then a third business is my elevated mastermind group for entrepreneurs. So, those three businesses are tied into things that I’m excited about that I focus on, I read about, I study about, I talk about. So, it’s not anything I need to walk away from. I mean, I’m fortunate and blessed enough to do just the stuff that I’m good at, that I love to do, and have other people help with everything else. So, there’s no reason to walk away and do nothing. I get excited about all this stuff.
Justin Donald: That’s awesome. And you are also an elected city treasurer managing $650 million of taxpayer money.
Chad Willardson: That’s right.
Justin Donald: So, I mean, that’s big time too.
Chad Willardson: Yeah, I mean, it doesn’t take a ton of time for me, but it’s a big deal. When I was first elected in 2016, it was an account that was worth $230 million, and our credit rating for the city was AA minus. And we had a looming debt crisis for our city that’s 170,000 residents here in our city in Southern California, and so, I’m happy to report, I changed some things financially around in the last nine years, saved the city, I think, $170 million in interest in debt costs, refinanced some debt for the future, worked out a deal, issued a bond, got our credit rating up to AA plus, and then grew the portfolio from $229 million to $650 million in the last nine years. So, as a volunteer, by the way, I donate 100% of that salary to charity. So, I do not get paid, but it’s something I really felt strongly about to help our community.
Justin Donald: That’s awesome. Well, I love that you’re using your skills to better your community, better the world, and that you don’t have to profiteer from it. That’s very big, very admirable.
Chad Willardson: Thank you.
Justin Donald: I’m curious, so you help people manage their wealth, and I’m sure there are tons of things you like seeing people get into, but then you’ve got your own family wealth. What are some of the differences in what you have, some of your high-net worth clients invest in versus what you invest in? And I’m sure there’s overlap. I’m sure there’s a lot of what you like for you, you probably should share with your community, which is what I do. So, I’m curious about that. And you do a lot with cash-flowing deals.
Chad Willardson: Yeah, that’s a great question. I don’t think a lot of financial advisors eat their own cooking, but I 100% do, which is why I relate to the higher end entrepreneur because I’m thinking like them in my own family life and my own financial situations. So, it’s easy to share ideas peer to peer. And the overlap is strong. Let me think. I mean, own commercial real estate, residential real estate, so do most of our clients. I own private equity and I invest in venture capital, so do most of our clients. I own a lot in the stock market. I use leverage and debt to enhance returns and to enhance growth in my business and in my investment portfolio, which most of our clients do as well. So, there’s a lot of similarities.
One thing I don’t personally own are bonds. I’m just not much of a lender. I’m more of a growth investor and owner. So, some of our clients definitely are in the tax-free bond space and they like having a more balanced portfolio where I’m just all growth, foot down on the pedal all the way. So, that might be one difference.
Justin Donald: I like it. So, tax-free bonds being municipal bonds would be like one example of that. Now, you had said something that I think is really important for people to understand. You said on your stock portfolio, you leverage the assets there by borrowing against them to invest in other alternative assets because in that instance, it’s debt that’s making the acquisition, so it’s a non-taxable event, versus if you sold stock, you had capital gains if there were gains, there likely would be gains for how long you’ve been in it. And then that is lowering the overall return profile than if you had that gain that you were taxed on, right? So, I’d love to hear you share a little more on this. We’re actually going to be talking about this at our upcoming September live event, is how to properly use leverage in all the different asset classes and the types of deals you should consider and not consider.
Chad Willardson: Yeah. This is the truth. I was very early on to this idea in 2003 at Merrill Lynch, when they started offering programs where you could borrow against your investment accounts. I was like, man, this is a way where, if a client wants to do a real estate deal, they don’t have to sell stocks, pay capital gains, take their horses out of the race. They could literally keep their stocks invested in compounding and growing, use that, pledge that as collateral, and still do the real estate deal. And it’s worked out. I mean, it’s worked out for our clients and for us to use both sides of the balance sheet strategically. If it’s a great investment, my philosophy is buy low and sell never. And I talk about, I love the buy, borrow, and die strategy, where it’s just like, I’m going to use my assets and the cash flow to buy new investments. I’m not going to be buying and selling. So, I’ve never been a trader. I’ve never been someone who’s a house flipper. I’m more of a long-term investor, and that’s been my strategy.
Justin Donald: Yeah. That’s very similar to me. I’ve sold very few assets even when I’ve gotten compelling offers. Although there’s one I regret and I probably should have just sold it during COVID, pre-COVID, during that ramp-up of crazy unreasonable prices, I probably should have pulled the trigger on a couple of assets. But like you, I mean, I’m in it for the long haul and there’s so much you can do when you can borrow against it. And by the way, this is what the wealthy do, wealthy people, the billionaire class usually has 15% to 25% of their net worth. I’ve seen it as high as 30% and as low as 5%. I mean, some true entrepreneurs will have nothing in the stock market because they want everything in their own businesses. But generally, that’s the spread. And then they borrow against that to buy more assets. And so, you’re doing that, which is great. My big question on that though is, years ago, it was a no-brainer because interest rates were so low. Based on where they are today and what are you seeing right now for those types of rates, but do you still think that that is a strong strategy? Like, is that still wise?
Chad Willardson: It depends on each client’s situation. And as a fiduciary, we review that and make sure that it makes sense for them. In most cases, it still makes sense for them. We can get rates that are in the fives right now.
Justin Donald: That’s great. That’s still a no-brainer.
Chad Willardson: Still no brainer and depending on your situation, consult with your tax advisor, but you may be able to write off a portion of your interest, so it’s even the net cost is less than the fives, so it still makes a lot of sense to use both sides of your balance sheet.
Justin Donald: And you mentioned earlier that you’re even a fan of crypto. And I’d love to hear, even what you’re recommending or sharing with your clients, I would say most projects are very much a gamble, but you’ve got 10-ish that are a lot more established, and then you’ve got Bitcoin, which is the front runner that I don’t think that there are too many people out there at this point that don’t think it’s going to continue growing and becoming something greater than it is. But I’d love your thought on it.
Chad Willardson: Yeah. I’m not a crypto expert by any means. I have friends that are experts. I definitely do. I’ve got a friend that has $200 million in crypto and he’s a very, very well-known guy that is an expert. So, I’m not an expert, but I do own three or four of the primary Ethereum and Solana and Bitcoin. And the way I look at it personally for myself is that it has to be money that I’m okay, if it went to zero, it’s not going to affect our lifestyle. And so, that’s kind of how I’ve always looked at it because it is very volatile compared to other investments I’m in.
Justin Donald: Yeah, and by the way, I like telling people in our community, anything you invest, you probably need to get comfortable with the fact that it could go to zero. I mean, even though there’s a lot of ways you can de-risk it, even though we have an incredible track record, I just want people always thinking that, yes, there is risk. Very few things are absolutely risk free. So, only invest what you’re willing to lose. But if you do a good enough job vetting the deals, vetting the sponsors, doing a good enough job of asset allocation and diversification, you should have a lot more wins than losses that would overall have a net positive growth on your portfolio.
Chad Willardson: It makes sense.
Justin Donald: So, something else that I think you’re brilliant at, and I don’t know if everyone in in your ecosystem knows this, but we talk a lot about leverage even from the standpoint of like systems. And so, it’s not just capital, although that’s important, but systems and people. And I think you do a brilliant job with the people that you hire, the way that you use executive assistants, the way that you use virtual assistants. And so, we’ve had a bunch of our partners and groups that we work with, Pareto Talent and BELAY and a number of other groups out there that just do some pretty cool things, operator groups and platforms where they’ll place operators inside your business.
Chad Willardson: Yeah, leverage for time, to me, is number one. That’s been a focus. I’ve been a big believer for probably 15 years of buying back your time and being strategic about what you do. I’m also very, very willing, Justin, to admit I’m not good at a lot of things.
Justin Donald: That’s good.
Chad Willardson: So, I don’t spend time doing things I’m not good at or that I really dislike and sometimes to the dismay of my wife. And she finally accepted I’m not building anything. Like, I’m not a builder. I’m not a handyman. We’re going to call someone for that. So, I have three full-time assistants, two are local here in Orange County, California. One is virtual overseas, but they’d handle 99% of the stuff that comes to me, and I handle the 1% that absolutely must be handled by me. So, they’re not coming onto your show. That’s something that’s handled by me, but I enjoy that, so I’m going to keep doing stuff like that. So, I just believe that if you have great people and they’re trained well and they’re bought into your vision and mission, they’re loyal, they’re ethical, and they’re great at what they do, then the sky’s the limit for everyone. And when we grow, they grow.
Justin Donald: And you’ve separated into two different categories if memory serves me correctly, and I’d love for you to share that because your approach to this was the first I had heard of this and the way your two executive assistants kind of play off of each other and figure out who handles what I thought is just brilliant, and we have tried to emulate some of that with my executive team as well.
Chad Willardson: The reason it’s the first time you’ve heard it is because I made it up.
Justin Donald: There it is. There it is.
Chad Willardson: Through mistakes and struggle, and then finally, an aha moment where I was like, this makes so much sense. So, I have a right brain and I have a left brain. And so, one assistant is my right brain and one assistant is my left brain. And it’s really that simple. Everything that is organizational, financial, and really like spreadsheet numbers driven is my left brain assistant and everything that is creative, personal, fun, and spontaneous is my right brain assistant. And so, they’ve got a very long list of duties and tasks, and it’s clear. Is this organizational/financial business? Or is this personal marketing, PR, branding, fun, stuff like that? Then it’s going to be right brain. So, they work very well together, thankfully. They’re both in the Newport Beach area, but yeah, it just finally worked itself out to be that clear separation. And I realize it makes all the difference.
Justin Donald: Yeah, that’s awesome. Well, I love that. We’ve taken from that. We’ve used it. It’s been great for our corporate structure and I think it’s just a wonderful way to kind of look at the different roles and tasks that people have and finding strengths that match up with it. And so, you live a killer lifestyle. You’ve taken some awesome trips. One of the things that I think is one of the most fun parts of getting to the higher levels of net worth, the higher levels of cash flow, like one of the greatest perks to me is flying private. And that is an expensive and sometimes unreasonable price point, but when you get to a certain level of net worth or a certain level of cash flow, it really can become a rounding error, as crazy as that sounds.
I interviewed a guy, Nik Tarascio, who owns a charter company, and so, we did a whole episode on private aviation and what that looks like. When do you buy a plane? When do you do fractional? When do you do jet cards?
Chad Willardson: I should listen to that one. I should listen and learn.
Justin Donald: It’s awesome. When do you go in on a plane with four people versus owning your own? And when do you upgrade to the next plane? But I’m curious for you, like, when did you make that decision? What was the impetus to kind of move in that direction? Obviously, with the bigger family, that kind of helps.
Chad Willardson: No, it was complete frustration. That was the only reason. It was never on my goal board, never on my vision board. I had never flown private once in my life and I bought a private jet myself. Sight unseen, never test flown, I didn’t see the inside. I mean, I saw pictures, but I was so sick of travel during the COVID stuff and just the hassles, the delays, the flight cancellations, depending on their schedules, where I said, I can’t do this anymore. It’s just not going to work for me. And so, that was it.
And I had people say, “No way, man. You got to try it out. You got to do a membership, do a jet car, charter it out, buy one with five people.” And I thought that defeats my purpose, which is total freedom. So, did I do it the right way? Or it probably goes against everything you guys shared on that show. But I mean, it’s worked out and it’s been, I don’t know, three and a half, four years now, and I probably spend $4 million a year. But I mean, does it ever make financial sense? Absolutely not. There’s no way you can justify it.
Someone says, how many times do you have to fly? Or, oh, well, you take your whole family and it has 11 seats for passengers. And I’m like, it does not ever financially pencil out to be like some smart financial deal. It’s not for money, it’s for freedom and flexibility and opportunities like being able to, we flew to the Kentucky Derby. We went with a bunch of friends and business associates and we saw the Kentucky Derby and it was my senior in high school, his playoff, big playoff volleyball match. And we saw the Kentucky Derby and we flew back and made it in time to see his entire match. And there’s no chance in the world that we could do both. And that happens honestly, Justin, on a weekly basis, where there’s stuff that I’m able to participate in with my family and it doesn’t compromise business or family. I get to do both.
Justin Donald: Yeah, I love that. And I love the hierarchy of like, hey, I’ll spend more to buy more time with my family, which we’re going to start talking about here in just a moment because I know, this is a huge platform that you like to speak on. I think, with a lot of people, they have a big exit, and back when you bought it, you could do 100% bonus depreciation and that can make sense if you– does buying your own jet ever really make sense financially on paper? Probably not.
Chad Willardson: Probably not.
Justin Donald: Warren Buffett calls his plane the indispensable, like, it’s just, you can never make financial sense around it. But can you help amplify it by getting that full write-off and offsetting a huge capital gain? I think that there are scenarios where it definitely makes sense and…
Chad Willardson: Yeah, you can take a little bit of the edge off a little bit.
Justin Donald: Help justify it, right?
Chad Willardson: Yeah.
Justin Donald: So, one of the cool things that you talk a lot about is your fully invested lifestyle and that’s a philosophy that you have that helps entrepreneurs succeed by prioritizing family first and then health and then fulfillment alongside business growth. So, a lot of entrepreneurs, it’s everything at the cost of the business. So, I’m going to put in all these hours and I’m going to do all these things, and it’s at the cost of the family, right? The business takes precedence over the family. But you’re the total opposite of that and you even prioritize your life and strategize your financial decisions around that. So, I’d love for you to share some thoughts there because I think this is a powerful premise or idea or way to live life.
Chad Willardson: I wrote an article for entrepreneur that kind of went viral, and it was called Why the Hustle Culture is a Big Lie, and it’s because I felt so much pressure from all these successful gurus online talking about you got to get up at three o’clock in the morning and you got to– if you’re not willing to give up sleep, you may not eat for three days, you got to put in 120 hours and this and that. And I felt like, man, the messaging is, this is part of what’s destroying families. It’s destroying families, it’s destroying faith. It’s like sacrifice everything to be successful. And so, I decided personally that that was not for me.
And I just wanted to take a different route, which was, I want to succeed big in business and at home, not either/or. And so, I’m not giving up big goals. I’m still sacrificing, I’m just sacrificing a lot of personal waste. Like, I’ve never watched one thing on Netflix my entire life. Nothing, like zero. I don’t have an account, never had an account. I’ve never seen anything. Yes, I probably missed an amazing documentary or series or something. I’ve never done it. So, like, I have watched maybe one movie every two years total.
Justin Donald: Wow. I just watched Mission Impossible yesterday.
Chad Willardson: I know, I know.
Justin Donald: It just came out. I love movies. I love shows.
Chad Willardson: I know. I haven’t seen it.
Justin Donald: I was going to joke and say, you don’t have Netflix because you have HBO and Hulu and half of TV, but I know you don’t.
Chad Willardson: I have none of that stuff. My movie this year was King of Kings, like that was the…
Justin Donald: Nice.
Chad Willardson: I think that’s what it’s called. Do you know what I’m talking about? It’s like cartoon. Yeah, I think it was called King of Kings or something like that, but that was the one movie for the year. So, I believe that you do have to sacrifice a lot to be successful, but I think we can be better about choosing what to sacrifice. So, I would rather be fully invested in my family and fully invested in my business. And I think you can do both successfully. And that’s what my next book is called, Fully Invested. That’s what it’s about.
Justin Donald: I love that. That’s awesome. Well, I remember in a previous business I was in, the mantra, the overall culture and theme of that business and even from top-down executives down to the base level was your work ethic is your badge of honor. And that’s the most important thing. And you put in the hours and you do what you need to do. And I think, for me, early on in life, that was probably a good move because it sharpened up my discipline. It allowed me to show that I could excel and outwork other people. And it was also before I had really developed a lot of skills.
Chad Willardson: Right.
Justin Donald: But the irony is that’s the exact opposite of the way that the smartest people, the wealthiest people do it because if you have great skills, then why are you going to sacrifice those skills to put in more work, right? The smartest people can figure out how to work less, put the right people in place, put the right systems in place, the right leverage all across the board, capital included, and grow it even more than if they were doing it all themselves or putting in the long 120-hour grind weeks.
Chad Willardson: And what do you have to show if you’re working 100, 120 hours a week? I mean, if you continue that for years, your family’s going to be broken and your health is going to be poor. And so, who cares if your business is successful and you’ve got lots of money if you’ve got no personal life, no family relationships, and no health, like I don’t see the point in that.
Justin Donald: Totally. So, what are some practical strategies then for entrepreneurs and for those in corporate America to win in both business and in home life, but without sacrificing one for the other? You said you’ve done both successfully. I know very few people that have done both successfully. I know a lot of people that have crushed it in business and their family is falling apart after many divorces, many relationships with kids that are just broken. I know a lot of people that have done very well on the family side, but really struggle financially. I mean, the great parents, wonderful human beings, but it’s a struggle to put food on the table. So, how on earth do you do both?
Chad Willardson: You’re going to have to buy the book, Justin. I’m just kidding.
Justin Donald: I like it.
Chad Willardson: No, it’s coming out in September, Fully Invested. So, the tagline is Why Work-Life Balance is a Total Lie, and then it’s seven strategies to win big in business and at home. One of them, I think, taking a fully invested approach, a fully invested leader knows how to communicate, how to work well with others, fosters a feedback culture and puts the right people around them, whether that’s in your business or your family life. So, being able to have discernment of the people in your inner circle, in your family and your business, I think, is critical to success. The people I admire who are really succeeding, they have great people around them and they have people that are willing to tell them the truth. They have people that know what their values are and will hold them accountable. And I think that’s important in your business and your family life.
So, if you don’t have anyone in your circle that will say, hey, Justin, like, you’ve been working for long hours. You missed your kids’ recital, you missed your kids’ basketball game. Your wife hasn’t gone on a date with you in over a month. Like, your health is looking kind of poor. Like, I don’t care that you’ve grown your membership in Lifestyle Investor group, but what are you doing, man? If you don’t have anyone like that, to me, that’s a dangerous situation we can put ourselves in. So, one of the things we need to have is honesty, a feedback culture, and have those conversations about what matters to us and what are we doing in our calendars. So a fully invested leader has a very intentional calendar.
Justin Donald: Yes.
Chad Willardson: Too many entrepreneurs, if you look at their calendar, everything is business. I think it’s very important to put family commitments in your calendar ahead of time because what’s in my calendar usually sticks. I’m not canceling everything all the time. Stuff’s flexible, but if I have important appointments in the calendar, I’m going to meet those appointments. So, I try to put family commitments with my wife or my kids or my parents in the calendar, reserve a time, and it may not be clear where it’s going to be, but I have a commitment that I made. I’m going to put it there, and that helps me make sure that I’m staying aligned with my family and aligned in my business.
Justin Donald: I had a huge epiphany because I thought I was really living life as a top-notch family man. And I would tell people, I’m a family man first and I’m a businessman second. And I had a friend call me on it and he said, “Well, we can put it to the test.” And I said, “Sure. How?” And he goes, “Let me see your calendar.” And I showed my calendar. And by the way, I do believe I had leveled up being a family man. So, I was way better than I was, but in my mind, I thought I was way better in that season than what actually was happening. And so, when I looked at my calendar, I was just appalled that my family was still being squeezed in to the openings versus put all the family stuff in first, work the business around it, and then you’re really living as a family man first, businessman second. And that’s been a huge transformation for me, even when I thought I was there already and had this wake-up call that, whoa, maybe I’m doing better, but like, I’m not competing against anyone else. I can’t be like, oh, I’m a better dad than so-and-so or I’m a better husband than so-and-so. It’s always compared to me.
And my wife’s good at reminding me that. Like, how are you based on where you want to be, where you want to show up for your family? And that’s, for us, something that’s been huge is getting regular weekly date nights, regular quarterly overnights, regular annual vacations, just the two of us for a week. We’ll do some couple stuff too, but those are the deal breakers. We’ve got to do it. And then having activities that we can do together, like pickleball, or my wife loves going on walks. I don’t necessarily love walks. She loves them, so I just do them, and it’s a great way to talk and connect.
Chad Willardson: Yeah, it’s awesome.
Justin Donald: We have our family, marriage, and planning day that we do for a full day, sometimes two days, every year to kick off the year, to look back at the past 12 months and forward on the next 12 months. And these have just been game changers for our relationship.
Chad Willardson: Yeah, those are amazing. Amazing habits. One thing we did for Easter dinner at my sister’s house, there were 20, 25 of us, and everyone put their cell phones on this table in the front lobby and one of the kids drew around it and put the names next to it. And for four hours, we just had like actually great conversations. Great actual conversations at Easter dinner was cool.
Justin Donald: That’s so good.
Justin Donald: We’ve got friends, Steven, back home is a member of the Lifestyle Investor Mastermind, a good friend here in Austin, and one of the things I’m so impressed with his kids on, we’ve got one, I think, that’s 17 and one that’s 15. And it might be 17 and 16. But they, with their friends, initiate, all right, phones in the basket or phones stacked down the table and as kids, as youth, as teenagers, they are doing this self-governed. And it is so cool to see, it is so inspiring to see those young leaders really getting what life is about and putting relationships first.
Chad Willardson: Yeah. They’ll be successful in the future. No doubt. They understand it already.
Justin Donald: 100%. Now, what are some formulas that you use to help entrepreneurs earn more, stress less, live a life more fully lived? I think you’ve got smarter systems and you are intentional about your wealth building. So, I’d love to know any formulas or systems that you can share.
Chad Willardson: Yeah. So, that’s a great question, Justin. For Pacific Capital, we have a lot of trademark processes that really hone in on whether it’s tax mitigation or financial freedom. I would say the overarching theme, at least on the wealth building side, is that everything we do is extremely specific and goal based first. A lot of people come to me first and say, “I’ve got this amount of money and I’m looking to invest. What should I invest in? What can I get great returns on?” And we inevitably always go back to what’s the money for? Like, what are you doing this for? What gets you up in the morning? What gets you excited?
And everyone’s different. People, we have a client who, they started a car wash. Well, it turned into a car wash empire really, but it started with one car wash. And 20 years later now, the car wash business they have is worth about $3 billion.
Justin Donald: Wow.
Chad Willardson: And it started with a couple college buddies who started a car wash business. And their goals are very different, the partners in that business. And we help overarching strategy with the partners, but when it comes to their individual wealth management plan, we’re talking with each of them very differently. There are different phases of life, different kids or grandkids situation. The husband and wife have different goals than the other partners, and so, it’s very fascinating to us to be on the inside of those individual meetings and then to talk strategy and planning with the whole group together. But recognizing, it’s kind of like, I have five kids. Each kid is very, very different. They came from the same parents. They’re in the same house, but they are very different people. And that’s the same with our clients.
So, the strategies and the filters and frameworks, how to be fully invested, a lot of those sit in the elevated business. The financial and wealth management frameworks and filters are in the Pacific Capital business, but the overarching theme is it starts with knowing where you want to go and what you want to achieve. And having a process and systems and accountability and coaching and support, I think that’s critical for success.
Justin Donald: Well, I love that. And when we onboard new Lifestyle Investor Mastermind members, there’s this protocol that they follow. And we had a session that we did. But it’s our first recommended session for them to get into, and it’s number one. I want you to figure out and get really clear, total clarity on what your goals are this year and beyond, what your dreams are, what are things that would be exciting and inspiring to accomplish. Same for your loved ones, for your spouse, for your kids, like what are their goals? What are their dreams, and getting clear on that?
Second is your investment criteria. What are the things that you should or shouldn’t be investing in based on what you want? Like, what are you looking for? Are you looking for long-term type of holds with a bigger IRR, but no liquidity? Or are you looking for cash flow? Those really matter. And how long has the sponsor been in business? And how many deals have they done? Have they ever lost money? How many times? Why? How have they corrected? I mean, there’s just so many things to kind of build that investment criteria.
And the third thing is figuring out that financial freedom number. What is that on a monthly and annual basis? Like, how do you buy your time back truly? How do you buy it back financially? How do you buy it back from systems and people and help that way? And then asset allocation, what is your asset allocation today? What should it be? Like, what do you want to move towards? And then, oh, yeah, by the way, here’s what the wealthiest people in the world do as a model.
And so, like all of those to us are so important when we onboard someone and bring them into our community and into our ecosystem because culturally, those are the things that matter most. It’s hard to say, you should invest in this or you should invest in that. I don’t know. We need to know all this, just like what you’re saying, like you’ve got to understand that. And unlike you, I don’t advise, right? I’m just teaching. I love to teach. And I know you do a lot of that too. And we’ll bring people in and we’ll have these awesome deals. But just because a deal’s awesome for one person doesn’t mean it’s awesome for another person.
If someone needs cash flow, they probably shouldn’t be investing in venture, and vice versa, right? And if someone has all the cash flow they need, they may not need an extra bit of surplus cash flow. They might be living in surplus and need to kind of allocate more capital. And so, each person’s situation is different.
Chad Willardson: Yeah, and that process helps, probably helps so many of your clients and members really just think about and like really reset themselves and think about what they want out of life and what they want out of their money.
Justin Donald: For sure. I mean, most people when they apply to the mastermind, the questions in the application are questions that they’ve never answered, they’ve never shared with anyone, they’ve never even discussed in many cases with their spouse.
Chad Willardson: Interesting.
Justin Donald: And it’s fascinating and it’s like, hey, as a community, how do we get good at this stuff? Or as a nation, like, how do we get good at this if we’re not willing to talk about it or if we don’t even know what it is?
Chad Willardson: Right, right.
Justin Donald: Like, if we don’t know of that worth, yeah.
Chad Willardson: You can’t hit a target. You can’t see.
Justin Donald: That’s right.
Chad Willardson: And so, you’re helping them set targets and really clarify what they want before they even join, which is awesome.
Justin Donald: Yeah. Well, before we wrap, I’d love to just know why you think traditional financial advisors often fail entrepreneurs and how you’ve tailored your approach really to help reduce stress and help produce that true lifestyle freedom, kind of your differentiation.
Chad Willardson: Sure. So, as a father to five kids, no offense to any non-parents out there, but I would not take parenting advice from someone who’s never had a kid. If I’m trying to get fit and go to the gym, I’m not taking fitness advice from someone who’s unhealthy and doesn’t work out. And in that same manner, entrepreneurs are wired differently. You can see the book in the background, Wealth Wired Differently.
So, if you are an entrepreneur, you should be taking advice from entrepreneurs who understand your brain, your DNA, how you’re wired differently. Traditional financial advisors don’t understand entrepreneurs because they aren’t one. They are an employee of a large firm. They’re an agent, they’re a broker. They are someone who is working under the management of many layers of people who are giving them lots of directions and instructions. An entrepreneur is open, they’re idea focused, they think differently, and so, therefore, their money advice should be wired differently as well. And that’s what we do.
That’s why I’ve been referred to many professional athletes in the last three years. I’ve taken none of them. It’s very tempting. I love sports, but I know that I’m not the best advisor to professional athletes. But I could say we’re the best wealth management team for entrepreneurs at a high level because we just get them, we absolutely get them. And when they talk to us, they say, “Wow, finally, someone actually understands what I’m trying to say.”
Justin Donald: Yeah, that’s awesome. Well, this has been so much fun, Chad. I appreciate you carving out some time and joining us. Where can our audience learn more about you and about your books?
Chad Willardson: ChadWillardson.com, or find me on LinkedIn. I’m there every day.
Justin Donald: Love it. Well, I’d love to wrap up this session asking our audience a question. I ask it every single week. But it’s an important one and just think about this and figure out for you what it looks like this time and what you can take from Chad today to really live this in your life. So, my question each week is this, what is one step you can take today to move towards financial freedom and really, just living the life you desire that’s on your terms, so again, not a life by default, but a life by design? Thanks for tuning in, and we’ll catch you next week.
Chad Willardson: Thank you, Justin.
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