The Math Behind a Smart Flyer (And the One I Just Took)

As someone who answers dozens of subscriber questions per week and coaches people live via the Bootcamp….

I'm in a good position to see clear trends in what card flippers do wrong.

Here’s one of the most common:

Taking “flyers” as a core part of their investment strategy.

What’s a Flyer?

It’s a card with a low likelihood of actually turning into real profit down the road.

It’s the guy you buy because you’re a big fan of the team and you just want to root for him.

Or, you get sucked into playing the “what if” game…

Like “what if he plays like an MVP the rest of the season?”

Essentially, these are long-odds type investments. Perhaps they’ll pay off well if they hit, but they rarely do.

If you’re looking at a card that has a 50% chance or less of increasing in value, I’d consider that a flyer.

The worst kind, in my opinion, are the “penny stock” cards - the ones that could 10x if they hit, but are much more likely to drop to near-zero.

What’s Wrong With Flyers?

Now, I’m not one to suck all the fun out of investing in sports cards. There is certainly a hobby and fandom aspect that I never want to fully ignore. After all, you could invest in something blah like Forex.

But here are the main problems with this:

  1. Investors tying up too much capital in “flyers.” This could mean you’re paying hundreds of dollars on a gamble, or you’re just starting out and the first 2 cards you buy are flyers.

  2. You’re emotionally tied to the outcome. It’s harder to unload the card at the right time, especially if it’s moved against you.

  3. Most people I see fall back on “flyers” because they can’t find cards that qualify as good investments.

Here’s an example:

Let’s say that you love the Cowboys and specifically Dak Prescott. You’re a lifelong fan and think of Jerry Jones as your real-life uncle.

So, you go spend $400 on a nice Prescott card!

Your logic is that he’s:

  • A good QB

  • On a popular team

  • Many analysts project them to be better this year (a big whoopsie after week 1)

But here’s the problem:

There are too many issues stacked against him that turn this from a good investment to a high-risk flyer:

  • So much uncertainty on a defense that turned over most of the players (could be construed as a good thing, but again… it’s still uncertainty)

  • Dak kind of is who he is - a very good player who’s unlikely to become a top-5 QB.

  • Missed at least 5 games in 3 of the past 6 seasons

  • And, by far, the biggest reason of all, as mentioned in last week’s newsletter:

That’s his flagship Silver Prizm PSA 10 rookie, which has increased dramatically for nearly 2 years straight without a good reason.

Could that card keep rising enough to make the investment worth it?

Of course. But it seems like the Cowboys would have to be dominant and Dak would need an MVP-type season. It’s possible, but what realistically are the odds of that? 25%?

And here’s the thing:

I like taking flyers! It’s placing a small bet on a player I want to root for.

But the flyers I take still need to be rooted in logic and (mostly) fit proper investing frameworks.

As fun as they are, flushing money down the toilet kind of ruins the whole experience for me.

How to Take Flyers in a Smart Way

First, let me share with you what a perfect flip looks like for me:

  • Superstar or young player who could become one

  • Rookie, autograph, or rare parallel or insert with market appeal

  • Card is a top brand

  • I can stack 3+ real reasons the player should rise inside my hold window (which I usually define as 3 to 6 months)

  • The card’s pricing chart has shown previous highs that would result in a nice profit for me (or it’s a young player with a legit reason to hit new highs)

A flyer is someone who might break a rule or two but still follows most of the frameworks that lead to a likely increase.

Recent Flyer I Bought

I recently bought a Silver Prizm PSA 9 Austin Reaves rookie card.

It’s not a perfect flip candidate by any means. He’s a veteran with no chance of becoming a franchise superstar. He’s in Luka’s shadow and always will be. He’s actually a bit higher in price than he was recently.

But here’s why I did it:

  • I spent $81, while my average card purchase recently has been $250. It’s a small part of my portfolio.

  • I’m a massive Lakers fan, and I root harder for Reaves than anyone else in the NBA.

  • He’s the clear #2 on the Lakers (massive fan base) with LeBron gone.

  • He’s had stretches that prove he can definitely pass 25 points per game this season.

  • His pop count and price history are almost nonexistent, so I think his increased profile gives him room to grow.

I also like to use flyers to test a hypothesis, which in this case is: how high can a #2 player rise, even on a non-championship team? Plus, I think he’ll put up big stats, and putting some money on his card is another way to root for that.

Investing in something with a higher-than-usual chance to fail is the price I’m paying to continue learning more about the market and flipping as a whole.

What to Take Away

For most people reading this, just cutting out flyers altogether is the smart way to go. Wait until you’ve established a rhythm and stacked some wins with your card flipping.

It’s like they say with writing: Once you know the rules, then you can break them.

If you’re already at this stage, my advice is to still stack a few reasons why a card will go up in value.

Buying a card with no legit reason to go up in value is a straight-up gamble. If you can turn your flyers from a 30% chance of working out to 50%+, it’ll limit your losses and keep your overall portfolio more profitable.

And We’re Done!

Before you go: Here’s how I can help…

1) Casual Flipper Bootcamp - 6 live training sessions designed to teach you to be a profitable sports card flipper. Join the waiting list today.

2) HCL Investor - My best investment plays each week, including cards, pricing, timeline windows, and more. Delivered every Saturday.

3) Cards to Cash - My entire investing strategy playbook, available on Amazon. It currently has 95+ reviews with a 4.8 rating.