Smart Money Brief

đŸ«š Ambition vs. Patience 😑

Good morning, traders


There’s a certain position I’ve been holding (and waiting on) for 16 years. Yes, sixteen. Not a typo. 

And yesterday morning, some news hit that finally sent that stock flying 40% in a single day. 

I’m going to share that story with you now. Not to brag, but to point out something critical that every trader needs to grasp: real conviction takes time to bear fruit. 

Sometimes, it takes years of holding through noise, distractions, and swings. Boy, there were some hard days and lots of doubt. 

But it was all worth it.

Back in the mess of the 2008 financial crisis, I had two trading mentors who kept pressing one idea: Fannie Mae and Freddie Mac are too important to go away. 

For context: In October 2007, Fannie Mae stock was trading for $68. Just one year later, it had cratered to a historic low of $0.47.

No one wanted to buy these stocks, obviously. There was zero greed, all fear. 

But beneath the rubble, there was a long-term opportunity brewing. Together, Fannie Mae and Freddie Mac backed nearly half of the single-family mortgage market in the U.S. That’s not a little niche play. That’s foundational. 

And when their stocks crashed, my mentors said, “Ben, they’re too big to fail.”

So I bought Federal National Mortgage Association, better known as Fannie Mae (OTC: FNMA).

I didn’t just dip a toe in, I believed in the thesis. I got in near the lows. But I didn’t trade it. 

I held the stock. For sixteen years.

There were false starts, wild swings, and a whole lot of political football. 

But I stuck with the idea because it wasn’t a short-term trade. It was a long-term bet built on a thesis that these companies would eventually be recapitalized and released from government conservatorship.

And then, this week, it finally happened. President Trump started talking about the companies, suggesting he might “take them public.” 

Image Courtesy of Axios

That alone pushed the stock up to $10.45. Sixteen years of conviction: Validated. At least in part.

This isn’t really about FNMA, though. It’s about what my long-term play teaches


The tension between ambition and patience.

Most of us who trade have ambition running through our veins. We want results. We chase progress. We hate stagnation. 

But it’s hard to be ambitious and patient simultaneously. Because ambition wants action. And patience says, “Not yet.”

If you’re going to build serious wealth through trading or investing, you need to learn how to hold both in balance. 

Whether it’s a swing trade that needs weeks or months to play out, a breakout that’s still coiling, or a decade-long thesis 
 ambition and patience need to be like yin and yang. 

With that in mind, let me show you my top setups of the day (and how to approach them with a healthy balance of both)


The 8 Best Smart Money Setups Right Now

Let’s shift gears to some setups and trade ideas from my recent live sessions


Peabody Energy (NYSE: BTU) – We’re watching for a move above $14.47 on the daily chart. There was unusual options activity targeting the May 30th $14.50 calls. Big orders. Smart money. Compression pattern setting up.

BTU chart: Year-to-date, daily candles — courtesy of TC2000

Etsy (NASDAQ: ETSY) – Sitting in a clean sideways consolidation with heavy premium buying at the ask. Multiple indicators lining up, and if we can get above $47.45, I like the June 20th $52 calls as a swing idea.

ETSY chart: Year-to-date, daily candles — courtesy of TC2000

MicroStrategy (NASDAQ: MSTR) – As Bitcoin hit all-time highs, MSTR popped. Watch the May $427.50 calls. BTC is driving the price action here.

MSTR chart: Year-to-date, daily candles — courtesy of TC2000

Marathon Digital Holdings (NASDAQ: MARA) – Still watching the $16.70 breakout for the June 6th $14 calls. Crypto’s tailwind hasn’t finished pushing just yet.

MARA chart: Year-to-date, daily candles — courtesy of TC2000

Robinhood (NASDAQ: HOOD) – Clean resistance at $25.28. Couldn’t break it yesterday, pre-market couldn’t either. But if it does, June 6th $26 calls are what I’m watching.

HOOD chart: Year-to-date, daily candles — courtesy of TC2000

Alphabet (NASDAQ: GOOGL) – Pulled back to support and bounced. I’m still holding positions here, and the June $620–$680 calls remain interesting. Strong structure. If the market firms up, I expect continuation.

GOOGL chart: Year-to-date, daily candles — courtesy of TC2000

Wells Fargo (NYSE: WFC) – Took a hit yesterday. I should’ve stopped out, didn’t. But it bounced off the 21 EMA on the daily. If it doesn’t hold there, I’ll cut it. But the structure is still intact.

WFC chart: Year-to-date, daily candles — courtesy of TC2000

Warby Parker (NYSE: WRBY) – Still waiting for the breakout from the bull pennant. Called out the $22.50 July calls. Patience required. If it doesn’t trigger, it doesn’t trigger. That’s trading.

WRBY chart: Year-to-date, daily candles — courtesy of TC2000

Trading and investing are about aligning your risk with your conviction. Sometimes, that conviction spans 16 years. Sometimes, it lasts five minutes. 

Either way, discipline is what lets you survive long enough for the wins to matter.

Patience isn’t glamorous. But it’s essential.

If you want to be around long enough to tell your own version of the Fannie Mae story, you’ll need both patience and ambition.

Happy trading,

Ben Sturgill

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