On weekends, I drink. Sometimes heavily. During the week? Virtually never. It helps that I don’t run with a crowd who wants to grab drinks every night after work. Right now, I’m juggling a full-time job and my MBA at the University of Georgia. If I added midweek drinking, my work productivity and grades would tank faster than Bud Light sales in Texas.
There’s one exception to my “no weekday drinking” rule. Airports and hotels. No matter what time it is, no matter how tired I am, no matter how anti-social I feel, I’ll plant myself at the bar, order a cocktail, and strike up a conversation with whoever’s next to me. Not to get drunk, but to meet people from completely different walks of life. It’s a simple pleasure of mine. I’ve lived in Kansas, Oklahoma, and Georgia. The folks I meet at these bars are from everywhere else. I listen to their stories, learn about their cultures, and see how they’re tackling life. Listening is the key here. Ask questions, shut up, and let them go. People love talking about themselves and telling stories.
Ninety-nine percent of the time, I walk away better for it. On the rare occasion I get stuck talking to a moron, I simply pivot to the person on my other side. Problem solved. An hour or two at the bar won’t kill you, but it might make you wiser, richer, or at least entertained.
Last night, I was in California for work and sat next to a guy named Skip at the hotel bar. Skip’s a car collector, in town showing off his 1967 Porsche 911. (Pronounced Por-shuh, not Porsh. Skip didn’t let my mispronunciation slide.) We talked for hours, and at one point, he asked how old I thought he was. I guessed 60. He raised his thumb. I said 65. Wrong again. Skip is 76. The bartender overheard and made a noise suggesting she was just as dumbfounded as I was. With a full head of hair, fit physique, and barely a wrinkle, Skip looked amazing for his age. He says the secret is twofold. 1.) Loving what you do for work, and 2.) Marrying a younger woman. Skips wife is 60. Atta boy!
Skip started working as a stockbroker at Morgan Stanley when he was 30. After three decades, he’d had enough of being told to push products that weren’t in his clients’ best interest. The incentives were designed for him to hit his numbers and juice Morgan Stanley’s bottom line, not to do right by the customer. So, in 2005, he walked out with two colleagues and started his own firm. Today, they manage $500mm in assets for high-net-worth clients across California. Skip has a garage full of muscle cars, a house on a hill above some big lake north of San Francisco, and a much younger wife (again, atta boy). He is an undisputed success. But what stood out to me was the fact that he was a genuinely happy human being. In today’s society, having money and becoming successful is demonized. It’s associated with unhappy people who want to shit on the rest of the world. I’m scared this is creating a generation of “non-hustlers”. More than ever, it’s socially acceptable to float through life with no urge for success. I’m afraid this will ultimately have negative economic ramifications in the coming decades. The point, though, is that there are examples of folks who busted their ass, made a shit ton of money for themselves (and others), and are genuinely happy. As someone who has yet to “make it” financially, it’s good to be reminded of why it’s so important to work hard when you’re young. Thanks for setting a good example, Skip.
Skip’s a self proclaimed “Independent” and is not thrilled with the current administration. While I agreed with him on a few points, I couldn’t match his level of pessimism. Personally, I’m hopeful we can grow our way out of our current deficit situation, which, if not dealt with, will be a huge problem for my generation as well as my children’s generation. It seems like opening up the checkbook and “Investing” our way to prosperity is Trumps MO. This administration is not “fiscally conservative”, regardless of what they want you to believe. Tariffs will help, but Trump’s negotiation style is risky. So far, so good. But who knows what will happen. That said, as a 25 year old, I have to remain optimistic. Best case, I ride the wave and get rich. Worst case, I ride the wave and get wiped out. If I get wiped out, I’ll be in the same boat as everyone else. By the end of this administration, we’ll either be in an incredibly strong position, or picking through the rubble. I’ll bet on America coming out on top (with a strategic hedge or two). Even though Skip chooses not to share my level of optimism and hope, likely because he’s older and has a lower tolerance for risk and uncertainty, we see eye to eye on the following: My generation is unable to talk politics in a respectful manner, let alone at all. Half the time, it’s awkward to even bring up and discuss policies that’ll shape the future of our country because everyone is sensitive about hurt feelings. Instead, people hide out in their cozy little echo chambers on social media, letting the algorithm spoon feed them brain rot that reinforces whatever nonsense they already believe. It’s one of the biggest reasons we’re so divided as a country. If you haven’t challenged your beliefs lately, go sit at a hotel bar with a 76-year-old, or anyone who sees the world a little different than yourself. Then listen. You might not change your beliefs, but at least you’ll have a better understanding of the other side.
I was up early this morning to get a workout in. Had some time before my meetings, so I parked myself in the hotel lobby to answer emails, grab breakfast, and do a little people watching. Around 9:30, Skip strolls in and comes over to say hi before heading to the car show.
First thing out of his mouth: “You’re up early. You really are a morning bird!” I thought he was being sarcastic (by 9:30 I’ve usually been up for four hours). Then I remembered him saying last night that he’s not a morning person. The guy was dead serious.
Moral of the story? Work your ass off and build a life where 9:30 a.m. counts as “early”.
Going to a few hotel and airport bars won’t hurt along the way.
Yours in fiscal prudence,
Colten Penner
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