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The Next $50,000 Challenge?

Posted May 09, 2026

Davis Wilson

By Davis Wilson

The Next $50,000 Challenge?

Welcome back to the Saturday Q&A where we cut through the market noise and get to your most pressing questions.

No topic is off limits.

Keep sending in your emails to AskDavis@paradigmpressgroup.com.

Let’s dive in:

I LOVED the Paradigm $50,000 Trading Challenge. I learned so much in April. Thank you all! Now… the big question is will you be doing it again?? – Amanda

I’m glad you enjoyed it and learned something along the way!
I had a lot of fun following the action too. And I still laugh thinking about the fact that Ron (the winner) ignored his phone for a few days.
Apparently, he saw he was around 200th place heading into the final day and figured he had no shot… so he stopped checking altogether.
As for another challenge, my guess is we do something similar again soon.
Stay tuned.

New Berkshire CEO Greg Abel seems content in just minting money through the business they already own. I think he’s afraid to tarnish the Buffett name and legacy and won’t do anything until he’s dead and buried. He surely doesn’t want to be second guessed on every move. This is the exact same situation Kalen DeBoer is in following Nick Saban as the head coach of Alabama football. – James

Well said, James. And great comparison with DeBoer following Saban.
Following a legend is one of the hardest jobs in business or sports. Every decision gets compared to the person before you.
And in Abel’s case, he’s replacing arguably the greatest investor of all time.
So I do think there’s an incentive to play things conservatively early on and prove stability first.
That was one of my biggest takeaways from the shareholder meeting. The focus was much more on operating Berkshire’s existing businesses well versus making bold investment moves.
That said, Berkshire’s massive cash pile almost forces action eventually.
At some point, Abel is going to have to put his own stamp on the company.

Hello Davis, I’ve only been investing for a few years, and I’ve had some luck now and then. But mostly longer holds. I have many triple-digit winners and one 3,600% winner with STRL – which I’ve sold half three times already. Is there any kind of general rule about what point you should take some of those gains? Maybe sell half at some point? – John

John, this is one of those questions where you could ask 100 professionals and get 100 different answers.
In fact, my best friend is a financial advisor at Merrill Lynch. I sent him your question just to get his take.
His response was basically a college essay sent over text message.
Here’s the gist:
It depends on your time horizon, your risk tolerance, and how large the position is relative to your portfolio.
The longer your time horizon and the higher your risk tolerance, the more room you have to let winners run.
Personally, I think most investors sell their biggest winners too early.
Some of my best-performing investments came from simply buying great companies and holding them for years.
As I write this, my original Nvidia position from 2017 is up roughly 8,500%.
I held it because the thesis kept getting stronger, not weaker.

Do you think we should continue to hold cryptocurrency? – Eva

Yes! I believe a small percentage of any long-term portfolio should be allocated to cryptocurrencies.
I believe the risk of not owning crypto can be a lot more damaging to your future returns than the risk of losing a relatively small investment.
You can read my full thoughts here.

Any thoughts on buying Meta Platforms (META)? – Earl

Absolutely! Meta is still one of my favorite stocks.
The company just reported fantastic earnings results – beating revenue and earnings expectations – yet the stock sank because of higher spending guidance.
It’s also one of the biggest and earliest beneficiaries of artificial intelligence.
I own the stock in my personal portfolio, and after the selloff I think this stock is a buy once again.

Important Update: Follow The Million Mission on Twitter/X

Big news: I just launched a Twitter/X account so you can follow along with The Million Mission in real time. If you want quicker insights, early reactions to breaking news, and a closer look at how I’m navigating the road to $1 million – this is where I’ll be.

Come hang out, ask questions, and follow the Mission as it happens @DavisPWilson.

Another Important Update: The Million Mission website is live!

I’ve gotten plenty of feedback regarding where to find previous alerts. Well, The Million Mission website is finally live and you can check out archived alerts here.

Portfolio Overview

Here’s what I’m currently holding in The Million Mission portfolio:

Fannie Mae (FNMA) – 2,500 shares @ $7.25/share

Uber Technologies (UBER) – 200 shares @ $80/share

Nvidia (NVDA) – 200 shares @ $179/share

Special Shoutouts

Thank you to those who emailed in kind words and thoughtful comments.

Thanks for being along for the Mission.

Please keep the emails coming.

Talk to you on Monday.

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