Money Monday Blog

This past weekend, I had a once in a lifetime opportunity (thanks to one of my business partners, Toby Eng) and I went to a charity event at Michael Jordan's old house in Chicago. It was everything I thought it would be and there was a Jump Man logo in many areas of the home to remind me where I was, if I ever forgot. It was an epic night, and it got me thinking about the GOAT. It is the inspiration for today's blog.

We even have this debate in our office, and it’s almost always generational. For some, LeBron is the obvious answer. For others, there’s only one GOAT, Michael Jordan.

I was a teenager during Jordan’s prime, and I can tell you, it was fun to be a basketball fan then. The NBA wasn’t just entertaining, it was electric. There’s a stat that perfectly captures it, during the two seasons Jordan stepped away to play baseball, NBA TV ratings fell by nearly 50 percent. Not just for Bulls games, but for the entire league. That’s how much his presence elevated the sport.

Jordan played 15 seasons, made six NBA Finals, and won all six, taking home the Finals MVP trophy every single time. LeBron? He’s made it to 10 Finals and won four with three different teams. He’s the all-time scoring leader, a model of durability, and one of the most skilled, intelligent players the game has ever seen.

LeBron might be one of the nicer superstars ever, Michael could be brutal. He was relentless, demanding, and sometimes downright hard on his teammates. But he made everyone around him better. He raised the standard so high that excellence was the only acceptable option.

That was the magic of The Last Dance (released for streaming during COVID). Decades later, you could still feel it, that competitive fire, the refusal to lose, the extra gear in the biggest games. From the Flu Game in ’97 to that shot over Bryon Russell in ’98, Jordan’s defining moments weren’t just highlights, they were proof that when the stakes were highest, he was at his absolute best.

In business and in life, you want people on your team who show up for you in the big moments, who have confidence not only when things are easy but when the stakes are high, and when the pressure is on. I think that’s also what you want in a financial advisor, a steady hand when you need guidance during life’s biggest decisions. Whether it’s selling a business, navigating a career transition, or deciding how to secure your family’s future, you want someone who rises to the moment when it matters most.

LeBron is greatness personified, but, for me, the GOAT will always be the one who never blinked in the biggest moments.

“You are the average of the five people you spend the most time with.” — Jim Rohn

It’s one of those quotes that’s so simple, it’s easy to scroll past. But when I reflect on it through the lens of parenting, it takes on new meaning.

Every time we encourage our kids to join a team…

Every time we nudge them toward the kid who’s kind, focused, and curious…

Every time we gently steer them away from the chaos…

What we are really doing is helping them choose a new kind of normal. Because normal is just what you’re used to.

When your friends study hard, it feels normal to study hard. When your friends are chasing big goals, that feels normal too. But when your group shrugs off effort or mocks success, that becomes normal just as quickly.

And here’s the weird part: You’re the one who picked those friends in the first place. Which means you chose your normal.

This has been bouncing around in my head a lot lately, not just as a dad, but as a grown up.

In the last 30 years, I’ve been fortunate to have some great friendships. Not always perfect. But consistently filled with people who hold me to a higher standard. Who dream big, do hard things, love well, and challenge me to do the same. Their version of normal? It’s shaped mine.

I don’t think we talk enough about this as adults. We spend time thinking about our diet, our money, our habits, but who we spend our time with? That’s shaping all of the above.

So maybe the question to ask isn’t just “What do I want out of life?” Maybe it’s: “Who already lives that way?” And then: “How can I spend more time with them?”

Choose your people. Choose your normal. Choose your life.

One of the hardest parts of advising clients in retirement is knowing when to say “yes” and when to say “pause.”

I love seeing clients finally buy the boat they’ve always wanted, take the dream trip, remodel the kitchen they’ve been talking about for years. These moments are why they saved. They’re why we plan.

But when you’re retired, you can’t just earn more money. Every big expense pulls from the same pool of resources that has to last decades. One “just this once” is fine, but a series of them can quietly become a pattern.

Most advisors plan in straight lines (similar monthly expenses every month), but real life plays out in curves. It’s also hard to anticipate and financially model how many “just once” things may come up in a client’s lifetime.

The tension is real. Say “yes” to everything now, and we might be forced to say “no” later when it matters most. Say “no” too often, and life passes by with a pile of money and a list of missed moments.

A solid financial plan, portfolio and the right financial tools are a large part of the the solution. The harder part is the human element, knowing when the additional spending or purchase leads to more happiness and knowing when it is more for more’s sake.

That’s why this job isn’t just about math, it’s about nuance. I’m not just managing money, I’m managing possibility. And the art of advice is living in that uncomfortable middle, helping “today you” enjoy life without robbing “future you” of freedom.

Written By: Shawn Peck, COO of LiveWell Capital

On a recent business trip, an unexpected observation tied together how small decisions can lead to success or failure in life and financial well-being.

While moving thru security, I noticed two men interacting with airport personnel while a third man stood motionless having his hands tucked inside an old sweatshirt. I watched and tried to imagine where they were headed and what brought them together. As they walked away, I noticed handcuffs on the third man and my “encounter” slowly drifted from mind until noticing them boarding my plane. This traveling crew was seated in the last row with now clearly the prisoner securely positioned in the window seat starring out into the distance. I wondered about his life’s story and what set of decisions, those both small and significant, would haven take him from a life of potential to a life of prison and confinement. My thoughts then transitioned to how this could relate to our financial life and the seemingly small decisions which can take us from a life of growth and prosperity to one of unwanted risk and disappointment. How often in life do we undervalue and overlook the small decisions such as…

- Consistent Contributions: Automated savings, power of compounding interest, regular investments.

- Spending Wisely: Creating budgets, what’s needed vs. wanted, avoiding high-cost debt.

- Smart Portfolios: Diversifying investments, being patient, understanding risk.

Collectively, these small, informed decisions will help achieve long-term financial goals and prevent a life of unfulfilled expectations and potential.

“The bottleneck is never the market. It’s always you.” — Alex Hormozi

If you own a business, this quote feels deeply personal. (Also by market, Alex doesn’t mean the stock market, which is what I usually write about, he is referring to the market and environment that our businesses operate in.)

It’s oddly freeing, and deeply uncomfortable. Because if you’re honest, brutally honest, most of the constraints in your business aren’t out there. They’re in here. In your mindset. Your systems. Your beliefs about what’s possible. Your willingness to let go.

I’ve learned this the hard way, and maybe you have too: Small thinking is seductive. It feels responsible. Grounded. “Wise.” But often, it’s just a clever disguise for fear. And small thinking shows up subtly:

• “We’re not ready to scale that yet.”

• “We can’t afford to hire someone better.”

• “That sounds like a big investment right now.”

• “Let’s just keep it how it is for now.”

But what if that line of thinking is the bottleneck?

The market might not be holding you back. Your mindset might be. We love to blame the market. The competition. The talent pool. The software. The client. The economy. But none of those things are more powerful than the internal decisions we’re making every day as leaders.

The real question is: Are you building your business to match your capacity, or your vision?

Business Problems Usually Fall into 4 Buckets:

1. Mindset – You haven’t allowed yourself to think bigger.

2. Delegation – It’s so tempting to believe you are the one that has to do everything, this will be the death of a larger vision.

3. Systems – You’re relying on heroic effort instead of repeatable processes.

4. Strategy – You’re solving today’s problem instead of designing for tomorrow’s scale.

And most of those decisions? They roll up to you. That’s the hard part, but it’s also the empowering part. Letting go to grow.

If you’re anything like me, you’re good at keeping a lot of plates spinning. But eventually, the best thing you can do for your business is to put a few of those plates down. Growth doesn’t always come from doing more. Sometimes it comes from getting out of the way.

Final Thought

If you’re the business owner, just settle in on the truth that most things really are your fault. And once you accept that, not with guilt but with clarity, you unlock the power to change almost anything. Not because the market changed. But because you did.

Here’s to thinking bigger this week and building a business that’s no longer bottle necked by small thinking!

“Money makes you more of who you already are.” - Dave Ramsey

We’ve all heard the stories…

The small town man who won $100 million and was bankrupt five years later. The young couple who split a Powerball jackpot only to split up, and split their fortune, soon after.

Statistically, nearly 70% of lottery winners lose it all within a few years. Bankruptcy, broken relationships, lost purpose.

Why? Because instant wealth doesn’t create capacity, it exposes it.

Money reveals the gaps in our mindset, not just our bank account. It magnifies both our strengths and our weaknesses.

When wealth comes slowly, through work, stewardship, smart decisions, we mature as it grows. We learn how to manage risk. We build competence, which breeds confidence. We develop identity beyond the commas in our net worth.

But sudden wealth skips that whole process. The inner scaffolding hasn’t been built. And the weight of wealth crushes what wasn’t ready to carry it.

This isn’t just about lottery winners. It’s about all of us... it's easier to chase windfall moments than it is to chase wisdom...

…the business owner selling for a big multiple.

…the executive cashing out Stock Options.

…the entrepreneur hoping for a lucky exit.

Or even, society trying to solve poverty with a payout instead of a pathway.

Wealth alone doesn’t solve as much as we think it will. Competence does. Character does. Community does.

Alex Hormozi said it well: “Confidence comes from competence.”

When you know how to add value, to steward wealth, to lead others, to invest wisely then confidence and lasting wealth follow.

So, what can we learn from lottery winners?

5 Lessons for All of Us:

1. Don’t wish for sudden wealth, wish for growing wisdom.

2. Wealth is a byproduct of adding value over time.

3. Competence compounds faster than money.

4. Stewardship is a skill, not a status.

5. The people around you shape your success, choose them wisely.

If you’re a financial advisor, this is why our work matters. We don’t just manage money; we help people build the competence and character to steward it well.

And if you’re a client, or just anyone hoping for a better financial future, maybe the goal isn’t a jackpot. Maybe it’s growing into the kind of person who could handle it, even if it never comes.

"We don’t stop playing because we grow old; we grow old because we stop playing." — Tag (2018)

There’s a reason this quote resonates so deeply. It’s not just a catchy line from a comedy; it speaks to something fundamental about life. My son and I watched the movie Tag the other night, the movie is based on the real-life story of ten childhood friends who, refusing to let distance, careers, or adulthood get in the way, have been playing the same game of tag for over 30 years. Every May, no matter where they are physically or where they are in life, they find a way to tag (or dodge) one another, keeping the spirit of their childhood alive.

It’s a reminder of something many of us have forgotten, how to play.

At some point, between career aspirations, back-to-back meetings, endless emails, and the all-consuming responsibilities of adulthood, we stop playing. We trade playgrounds for boardrooms, bike rides for carpools, and laughter for logistical planning. Life starts to feel more like a to-do list than an adventure.

But what if we built play back into our lives? Not just as something we do on vacation, but as a daily rhythm. What if we prioritized fun and connection with the same urgency that we prioritize deadlines? What if we allowed ourselves to be a little more spontaneous, a little less rigid, and a lot more present?

The men in Tag could have easily let their game die out, just as most childhood traditions do. But they made a conscious decision to keep it alive. And in doing so, they not only strengthened their friendships but also refused to let life become just a series of obligations.

Maybe we don’t need to start an elaborate game of tag (although, why not?). But it could simply be about adding some more fun to each day or week, something simple like…

• Make time for fun traditions with friends

• Play that silly game with our kids

• Family dance parties

• Laugh more, even when times are tough

• Games with your work team

• Pursue hobbies simply for fun

Because play isn’t just for kids, it’s for anyone who wants to feel alive. And if we’re lucky, we’ll realize that growing older doesn’t mean we have to grow old.

Tag—you’re it.

It’s funny how one sentence, just a few words, can make you rethink whole areas of your life. That’s the power of a great quote. A well-placed phrase has a way of cutting through the noise, simplifying complex ideas, and leaving a lasting impact. Here are ten quotes that have been on my mind recently, each carrying a nugget of wisdom worth reflecting on.

My Current Favorite Quotes

1. “We suffer more in our imagination than in reality.” – Seneca

2. “If you are the smartest person in the room, then you’re in the wrong room.” – Confucius

3. “The rate of return on money never saved is always zero.” – Unknown

4. “It’s never too late to be what you might have been.” – George Eliot

5. “Never put a comma where God put a period, and never put a period where God put a comma.” – Mark Batterson

6. “Care what other people think, and you will always be their prisoner.” – Lao Tzu

7. “Our life is what our thoughts make it.” – Marcus Aurelius

8. “Nothing will cost you more in life than a predetermined belief that things aren’t going to work out.” – Donald Miller

9. “Spending money to show people how much money you have is the quickest way to have less money.” – Morgan Housel

10. “Without vision, the people perish.” – Proverbs 29:18

The best quotes have a way of sticking with us, reshaping the way we think, and reminding us of what really matters. Maybe one of these struck a chord with you today. If so, let it sink in, sometimes a few words are all it takes to change everything.

I turned 47 this year. My kids turned 11 and 15. Which means, almost daily, I find myself standing in two different worlds - the one I grew up in and the one they’re growing up in.

When I was their age, it was the late ’80s and early ’90s. I remember riding my bike around the neighborhood until there was nobody left playing basketball or soccer. I knew roughly when I needed to be home for dinner. I remember there were a couple of days a year where the arrival of my report card determined whether the evening was going to be a celebration or a quiet one. My parents encouraged me to study - my mom, who had a PhD in English, gave me extra help in writing (sometimes more than a little 😀) - but beyond that, they didn’t know what I got on every quiz or whether I turned in every worksheet. If a teacher had something to say, they said it during a conference or a casual run-in. There was a kind of distance between school and home, and I think that distance gave me some space to grow.

Today? It’s different. Through platforms like Canvas, we can see our kids’ grades in real time. We can know when something hasn’t been turned in, often before they do. My wife and I know when a test was taken and how they did on it - sometimes before they’ve even processed it themselves. That space I had growing up, it’s mostly gone for them.

And the choices today are endless. Kids don’t just pick classes, they curate schedules. There are online forums, spreadsheets, and peer-reviewed methodologies for how hard or easy to make your high school experience (our son enters high school in the fall). Tutors exist for individual subjects. Strength and conditioning coaches exist for youth sports. Club teams now run year-round, and not just for the elite. Even in college, apps like Life360 can tell you whether your kid made it to class—or whether they were out too late, or spent the night somewhere you weren’t expecting.

The access is constant. And if we’re honest, so is the temptation.

We want our kids to be independent, resilient, motivated. We say we want them to create their own fun, to fail and get back up, to figure things out. But technology keeps whispering: you could intervene. You could check that assignment. You could remind them about that quiz. You could email that coach. You could fix it.

I don’t know what my parents would have done if they’d had this kind of access. Maybe they would’ve shown more restraint. Maybe not. But I do know it’s easier than ever for us to get involved - and harder than ever for our kids to get any real space.

And here’s the twist: we spend a lot of time talking about how technology is affecting our kids. But maybe it’s affecting us just as much. Maybe the constant connection isn’t just fueling their anxiety, maybe it’s fueling ours. Maybe the same tools that were built to help us guide and support them are actually amplifying our own fears and creating pressure we pass down without even realizing it.

I’ve started to wonder maybe the issue isn’t how much screen time they have—but how much we have. Maybe their games, their shows, their online worlds are a kind of escape from our constant supervision. Maybe they need a break not from tech, but from our interaction with it. From us seeing everything, knowing everything, weighing in on everything.

I don’t have the answers. I’m not sure if the answer is to delete Canvas or just check it less. I don’t know whether we’re supposed to step back entirely or just become more aware of when and why we step in. But I do know this: we can’t expect our kids to become self-reliant, self-motivated, and joyful, if every part of their lives is curated, measured, optimized, and supervised.

Sometimes, I think the best thing we can do as parents is to step back - not out of disinterest, but out of love. Not to abandon, but to allow. To give our kids the same gift we had, even if we didn’t realize it at the time: the gift of space.

And maybe, in giving them that, we give ourselves a little freedom too.

"Nothing will cost you more in life than a predetermined belief that things aren't going to work out" - Donald Miller

I’ve reflected on this quote a lot lately (I love Donald Miller), and the more I think about it, the more I realize just how true it is. It’s ironic, really—because if you’re an optimist, this message resonates instantly. But if you’re a pessimist, you might dismiss it as just another feel-good platitude. And that’s the tricky part: I’m not even sure optimism can be taught. It seems like people are either wired to see the possibilities or the pitfalls. (Side note: That sounds like a close-minded thought in a blog about optimism, but most of my experience in trying to convert pessimists to optimists have failed… converting mindsets for people hellbent on seeing the negative in life might be the only thing I’m pessimistic about).

Here’s the thing: optimists have a huge advantage in life. They see doors where others see walls. They find opportunities in setbacks, learn from failure, and believe that tomorrow can be better than today. This mindset doesn’t just change outcomes; it changes the way life is lived. There’s a self-fulfilling prophecy to it: if you believe things will work out, you’re more likely to keep trying, adapt, and find solutions.

On the other hand, pessimism can be a heavy burden. A predetermined belief that things won’t work out often becomes a self-fulfilling prophecy too. When you expect failure, you stop trying—or worse, you don’t even start. Life becomes smaller, possibilities more limited, and dreams fainter.

So, is writing about this a waste of time? Maybe. If you’re wired for pessimism, I can’t promise that a few paragraphs will change that. But if there’s even a small chance that someone might reconsider their outlook, that they might challenge their default assumptions, then it’s worth it.

Because the cost of a closed mind is just too high. And the reward for even a glimmer of optimism? Well, that can be life changing.