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JR Gondeck is the sharpest financial mind I’ve had on this show. He’s a Wealth Advisor & Managing Director at The Lerner Group. Not to mention he’s been featured in Forbes, Barron’s, VP at a big bank and has 4 kiddos!
JR works with families to promote intentional communication and drive collaboration between all generations. In fact, he recently co-authored a book titled, Family Value at Risk, which details the importance of inclusive and intentional communication among family members “to leave a legacy wealthier than money.”
JR leverages his deep knowledge of global financial markets and passion for investing to guide clients through market trends. He’s an advocate of financial literacy and hosts family meetings to connect with the next generation.
In this episode, we discuss JR’s thoughts on Bitcoin—whether he believes in its potential as a long-term currency. He focuses on its limiting factors and compares the cryptocurrency to gold.
JR and I also talk about the importance of knowing one’s Net Worth. He says he’s always surprised by how many people don’t know their Net Worth, which he says is crucial to know, adding, “Detail everything—from 401K accounts, insurance, investments you’ve made, mortgage & interest rates—so that you really know what the bottom line number is.”
Especially at our age (JD & I are the same age), he says, “It’s critical you know where everything is and how it’s titled.”
Why is this so important (that you know your Net Worth)?
Number one. It allows for better decision-making, both short-term (can you buy a new car with the motherf*ckin’ driver seat sittin’ in the middle?) and long-term (can you and your son Weezy get a house by the water?)
This conversation was fun. My guest was sharp as they come. He makes many predictions during this episode that have already come true!
But perhaps the most impactful part of the discussion, for me at least, was how he now has me thinking about multi-generational financial strategy. Whereas I considered myself a long-term thinker before now, JR has me adding pages to the ‘ole financial playbook.
Hope you learn as much as I did!
Other topics discussed:
- How JR deals with Chicago’s miserable climate
- Adjusting through the tough months of “lockdown”
- What got JR into training & fitness
- Overcoming the limiting factor of Bitcoin
- How has JR’s profession changed since the 80s
- Transaction-based business vs relationship & family-driven business
- The concept of fiduciary
- Investment return vs wealth return
- Should you know your parents’ Net Worth?
- Opening a 529 account for your kids
- People focusing more on income vs. Net Worth
- Leasing a car vs. buying a car
- JR’s mentor was a student of Milton Friedman’s
- Phil Donahue episode with Milton Friedman as the guest
- Maximizing shareholder-value
- Investing in individual stocks on behalf of clients
- Shortcomings of mutual funds
- How much cash his clients keep “on the sidelines”
- Inflation, stock prices, house prices
- Technology advances & efficiencies in car-manufacturing
- Switching to electric vehicles
- Buying stocks of companies you use
- Roblox (RBLX) IPO
- Importance of structuring your time
- Moms going thru difficult times during the pandemic
- Getting a Financial Advisor in your age demographic
- Proactive Gifting
- Why our dads are hesitant to spend money to make memories
- People naturally want to save and see their assets continue to appreciate
- Pros and cons of starting a trust
- JR’s crisis-investing playbook (used 3x in past 20 years)
- Benefits of dollar cost-averaging (DCA)
- How hyper-rationality may have harmed JR’s personal relationships
- Benefits of having a life coach
- Why JR believes his marriage failed
- Getting a Match-maker & how it works
- Three connections JR looks for in a woman
- Going through a mid-life crisis
- Why JR is a big fan of Ayn Rand
- Why JR doesn’t own Tesla stock
Questions asked:
- How do you deal with being forced indoors in Chicago?
- Does that mean COVID wasn’t a big adjustment for you since you’re forced indoors half the year anyway?
- Do you have a sports background? Is that what got you into exercise?
- Can I ask you about Bitcoin?
- How do they overcome its limiting factor? Is it a matter of continuing to divide Bitcoin by way of halving?
- How has your profession changed since the 80s & 90s? Would you have made more money doing [your job] back then?
- Can you explain what a fiduciary means? Is that something that was around back then?
- Does being proactive mean contacting your clients more than quarterly?
- Do you think we should know exactly what our parents’ net worth is?
- If one of your clients is buying a car tomorrow & they have no idea how much to spend on a car, what would you tell them?
- Is there a federal/state tax law in getting a tax credit up to $10,000 when you trade in a car?
- Is there an investor that you admire most?
- Have you seen the Phil Donahue episode with Milton Friedman as guest?
- Do you invest in individual stocks on behalf of your clients?
- How come there’s not as much talk about mutual funds anymore?
- How much cash, as a percentage of Net Worth, do your clients on average keep on the sidelines?
- Haven’t we been worried about inflation since 2008-2009?
- In 2003, when I bought my first SUV, it was about 2 years old. It had about 25,000-30,000 miles on it & I paid about $20,000 for it. Just recently, I bought my wife an SUV for $20,000 and is about 2 years old & has the same miles on it. How can that be?
- Is it possible that we’ll still be talking about [the prospect of] electric cars 30 years from now?
- Are you a proponent of buying stocks of companies that you use?
- Can you give me an example of something you’ve learned from your kids that you’ve been able to use to benefit not only you, but also your clients?
- Can you walk me through your structured time?
- Do you have a boss?
- Do you think it’s important for someone to have a financial advisor that’s roughly their own age?
- What is the average size of a portfolio for your clients?
- Wouldn’t it better to put $10,000 in a 529 plan now rather than do $100 a month for many years?
- Can you give me advantages & disadvantages of starting a trust?
- What would you say is the average age that a grandkid would gain access to the money that’s designated by the deceased?
- Do you ever see situations where trustees are paid a little bit?
- Has your tendency toward hyper-rationality harmed you in your personal relationships at all?
- What went wrong in your marriage?
- Was your oldest kid devastated by the news [of your divorce]?
- Are you using apps to try to meet people?
- Can you give me an idea how the Match-maker stuff works?
- How does the fee structure work in a Match-maker service?
- How did you find your Match-maker?
- Can you give me an idea what you’re looking for in a woman?
- Would you call what you went through a mid-life crisis?
- How did you get into Ayn Rand?
- What is it about Rand that appeals to you?
- Now that you’re single, do you find yourself driving a nicer car, wearing nicer clothes, and keeping fit?
- Do you own Tesla stock?
- Do you think America is due for a divorce?
- Which social media apps are you on?
Fun questions:
- Is social media net positive or net negative for society?
- Do you think not wanting something is just as good as having it?
- If you could organize a dinner party of 6 guests, and have either every one you’ve ever hurt or everyone who has ever hurt you, which would you choose?
- If someone offered you $100,000 worth of stock of either Spotify, Amazon, or Tesla, which would you take?
- In their prime, who are you taking on a dinner date– Heather Locklear, Kathy Ireland, or Christie Brinkley?
- Same question: Cameron Diaz, Alicia Silverstone, or Christine Taylor?
Listen here:
Connect with JR:
- LinkedIn: JR Gondeck
- Twitter: @GondeckJr
