I'm about a quarter of the way through Ron Chernow's massive biography on President U.S. Grant, and it's shocking how much of a loser he was.

At the dawn of the Civil War, Grant was 39, battling alcoholism, had a string of failed business ventures, was swindled and stolen from multiple times and was pretty much broke and working as a lowly clerk in his fathers leather shop in Galena, IL while having his two younger brothers as his bosses.

And I find myself liking him MORE because his constant failures make him human and incredibly relatable.

This got me thinking about sharing my own investing mistakes and fighting the natural urge to keep them hidden and out of sight.

But through our mistakes, we learn, grow, evolve, and can help others by sharing our experiences.

I purchased my first share of Nexstar Media (NXST) on November 21, 2022, for $169.95, and it quickly became my top individual stock position.

It's a great company led by founder Perry Sook, but the technological shifts in their industry are undeniable and beyond management's control.

Which is why, despite record revenue, a fast-growing dividend, and high share buybacks, the stock price has been flat since February 2021. So, despite good financials, the stock market is saying they're seeing what's happening.

It kinda feels like investing in the best horse and buggy manufacturer, the Durant-Dort Carriage Company, in 1898, as the winds of technological change began to blow.

Broadcast TV's share of political ads dropped from 55% in 2020 to 48% in 2024, which shows that Nexstar's slice of the advertising pie is shrinking.

In the April Nielsen TV trends report, Nexstar's bread-and-butter broadcast was down 7% YOY while streaming continued to expand by 15%.

I ran a fun experiment and asked my 17 and 16-year-old daughters if they'd ever watch broadcast TV. My 16-year-old said, "What's broadcast?"😳

They said that they get their news from TikTok or YouTube, and they'd probably never sit down and watch broadcast television... and you know what? I can't remember the last time I did either because we're a cord-cutting family!

If you're like me and listen to lots of podcasts, it shouldn't be a surprise that Donald Trump is being called the first "podcast president." President Trump appeared on 14 podcasts, and his interview with Joe Rogan garnered more than 53 million views. With numbers like these, political ad dollars will follow the ears and eyeballs at an increasing pace.

I'm 47 as I write this, and I have many years of investing ahead. I want growth, not stagnation at best and gradual decline at worst, from the companies I'm invested in.

If I were 70 and living off dividend income, then a predictably and slowly melting ice cube that generates a lot of cash might work.

In 2003, I began investing a small amount in a company 401(k) plan, only using 1% to 3% of our pre-tax income. In 2018, I started buying penny stocks, then became serious about personal finance, and in 2025, I find myself analyzing demographic trends.

So while unwinding my biggest individual position feels like an admission of failure, it's a celebration of positive evolution.

Don't get me wrong, I love dividend income, and I joke that "dividends are one helluva drug."

However, I'm looking for a quality dividend growth company that's increasing its dominance, such as Costco (COST), rather than one that's fighting against fragmentation, like Nexstar Media (NXST).

We visit Costco 1-2 times a month, and my teenagers even suffer through it because of the free samples. They likely won't ever consume broadcast TV, but theres a high likelihood that they'll become Costco members.

In June, we have two vacations to pay for, including some additional expenses that popped up, so I'm taking this opportunity to unwind Nexstar. We are keeping a meticulous spreadsheet of everything we withdraw from our taxable "overflow" account and will replenish that bucket in time.

We don't know how our story ends, but like President Grant, if we continue to evolve and improve from our failures, the sky is the limit!

Hit reply and let me know what your biggest investing evolution has been. I'll respond to every reply!

Disclaimer: This is not investment advice, just one person's opinion that may be incorrect. Do your own research before making any investment decisions.

😁THANK YOU to all who responded to the last newsletter!!

Check out the portfolio on Blossom, the podcast, or see what’s cooking on YouTube.

And now, here is this week's portfolio activity...

Dividends Received This Week ~$17.70

McDonald's (MCD) | $17.70

Dividends Received Year to Date~

$2,598.96

Stocks Bought (AVERAGE)

1 Realty Income (O) | $57.24
3 Schwab International Dividend ETF (SCHY) | $27.406
1 Vanguard Total Stock Market ETF (VTI) | $293.50

Notable Ex-Dividends This Week + SSD Score

6/23 FedEx (FDX), 2.57% | 64S
6/24 Disney (DIS), 0.85% | 70S
6/27 British American Tobacco (BTI), 6.16% | 45BS
6/27 Philip Morris (PM), 2.95% | 70S
6/27 Medtronic (MDT), 3.29% | 99VS
6/27 Keurig Dr Pepper (KDP), 2.74% | 70S

🎙️Podcast of the week🎙️

The Value Play Hiding Behind...

Jun 18 · The Dividend Mailbox®

36:44

The Dividend Mailbox has a very interesting and very old value idea from across the pond. You might be interested in this iconic brand after listening to this one!

🎦If you missed it, check out the 5 rules I have for AFTER you buy a dividend stock!

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🎶Random music from the Dapper Dividends Jukebox🎶

Covenant - Dead Stars