‘S&J Investments’ Guide to Asymmetric Investing: High Floor, Higher Ceiling

Guide to asymmetric investment

My Personal Framework for outperforming the market through research and concentrated capital deployment

Note:

This is my own personal investing system. This is not gospel, it is not a known and accredited investing framework. It is not without risk. However this is how I have learned to invest and I have significantly outperformed the market with this framework during bull cycles.

It is not for everyone and it is higher risk than more traditional and diversified strategies. When drawdowns come in a concentrated portfolio it can be fast and aggressive, and you need to appropriately weigh that risk.

My Investing Origin Story: $50k to $800k in 6 Months

I didn’t realize it until recently, but for the last four years, I have been trying to recreate one specific moment in time.

My first massive win came during the SPAC craze of 2020 and 2021. For those who weren’t there, a SPAC (Special Purpose Acquisition Company) is essentially a “blank check” company that lists at $10. Until they merge with a target company, that money sits in a trust. That means no matter what happens, the stock has a hard floor at $10.

I realized the math was broken in my favor. I could park a massive amount of capital in a SPAC trading at $10.80. My downside was 80 cents (about 8%). My upside? If they announced a merger with a hot company, the stock could go to $20, $30, or $50.

I started using SPACs led by big Wall Street or Silicon Vally leaders as bank accounts. Park a large amount of money, wait for the announcement, I make 40% in a day.

Then, I discovered Warrants. These were essentially long-term call options attached to the SPACs. There was a bit more downside, but they gave me massive leverage on that upside.

I took $50,000 and turned it into $800,000 in six months.

I wasn’t a genius; I had just found a perfect asymmetric setup. High floor (guaranteed by the trust), unlimited upside (driven by the mania), and leverage (via warrants).

When the SPAC bubble popped (and I lost 200k in 4 days, taking me from $1M to $800k), that easy money vanished. But the principle stuck with me. I have spent the last four years refining a strategy to find that same risk/reward profile in the regular market.

This is how I do it.

1. Defining Assymmetic

In the investing world, “asymmetric” describes a scenario where the relationship between risk and reward is completely disconnected: in your favor.

My Definition: An asymmetric investment is a setup where the stock’s price floor is high because it is already trading at a compressed multiple relative to its peers. The downside is hypothetically mathematically limited because the stock is already “on sale.” Meanwhile, the upside ceiling is virtually uncapped due to a specific catalyst the market is ignoring.

  • Symmetric Trade: You bet $1 to make $1. (Coin flip).
  • Asymmetric Trade: You bet $1 to make $10, and if you lose, you only lose $0.20 because you bought the dollar for 20 cents from a guy who didn’t understand how much a dollar is worth….

We aren’t just looking for growth. We are looking for mispriced growth. We want stocks where the market has made a mistake.

2. Concentrated Portfolios

(This is optional for those who are on the aggressive side, your whole portfolio does not need to be looking for asymmetric bets. You could just try to allocate 20% of your capital to asymmetric plays to give your portfolio some beta.)

The core philosophy of asymmetric investing is Concentration. It is the confidence and opportunity to deploy a large amount of capital into a specific, concentrated place because you have done the work to verify the floor. When the math is broken in your favor, you don’t bet small. You bet big.

3. Find the Hot Table

Think about the movie 21 with Kevin Spacey. The MIT students weren’t gambling; they were counting cards. They were waiting for the deck to become “hot”: disproportionately stacked with face cards.

When the count was high, they signaled the spotter and shoved their chips into the middle of the table

4. How do these Set Ups Happen?

Markets are efficient eventually, but can be very inefficient in the short term. They react to headlines, not math.

Opportunities open up when:

  • Inflection Points: A company shifts from burning cash to printing cash. The algorithm hasn’t caught up to the new profitability yet.
  • The “Boring” Pivot: A company does something unsexy that becomes critical. $CRDO was a boring cable company until data centers needed their specific connectivity for AI. Suddenly, “boring” became “infrastructure.”
  • Strategic Acquisitions: The market hates complexity. When $SKYT bought the Fab 25 facility, the market saw “expenses.” We saw “capacity.” The market was wrong; we were right.
  • Policy & Macro: The market often misses second-order effects. Tariffs scared people away from energy, but for $TE, tariffs were a moat that protected their business.

5. Key Terms

You need to understand the metrics that matter.

  • Market Cap: The total price tag of the company.
  • Revenue: Top-line sales. The raw fuel.
  • P/S (Price-to-Sales): The most critical metric for growth stocks. It is the Market Cap divided by Revenue.
  • Why it matters: If Peer A trades at 20x Sales and Peer B trades at 4x Sales, but they have the same growth rate, Peer B is the asymmetric opportunity. Peer B is the compressed spring.
  • There other ways to value a company. The point is to have a consistent measure of how you evaluate the price tag of a company in relation to its revenue and growth rate against its peers. You have to figure out if its cheap or expensive.

6. The Asymmetric Screener

When I run a screen, I am looking for a “Three-Legged Stool.”

  1. Undervalued: The stock must be cheap relative to its competitors (Low P/S). This provides the Safety Floor.
  2. Rapid Revenue Ramp: The business must be accelerating. This provides the Catalyst.
  3. Hot Sector: The market must care about this industry right now.

No Pre/Low Revenue Companies. I do not consider pre-revenue or minimal-revenue companies to be asymmetric. I also cut my teeth in SPAC era so I have seen big promises go unfulfilled.

  • Execution Risk: A company with a “promising technology” but $500k in revenue isn’t asymmetric; it’s fragile. They have to grow into their market cap. If they stumble on execution, the stock could tank and if they can’t execute you have a poor chance of recovery.
  • Backlog Risk: I have seen countless companies tout a “$100M backlog” and still fail. A backlog is just a list of promises until they have the operational chops to convert it into cash.
  • No Floor: With no meaningful revenue to anchor the valuation, there is no “floor.” You cannot calculate a P/S multiple on zero.
  • The Rule: I need to see the machine working. I want to see the revenue ramp already happening. This ensures near term catalysts during earnings if the company is actually undervalued. Each earnings should validate the re-rate.

Cold Sector = Dead Money (The

$SOFI

Trap)

You can find a company that is undervalued (Leg 1) and growing (Leg 2), but if the Sector (Leg 3) is cold, you will lose.

Look at

$SOFI

for the last two years. It was profitable. It was growing. It was cheap. But the market hated Fintech. It was “dead money.” You cannot fight the the ocean. You need the sector momentum at your back.

7. The “EBITDA Turn”: The Ultimate Catalyst

The most explosive moment in a stock’s life is rarely when it is mature. It is the exact quarter it flips from burning cash to printing cash.

  • The Mechanism: When a company posts its first positive EBITDA quarter, or hits FCF (Free Cash Flow) positive, the algorithmic models change. Institutional capital that is banned from buying money-losing stocks is suddenly allowed to enter.
  • The Play: I hunt for companies that are one quarter away from this flip. That is where the maximum asymmetry lies: buying just before the “institutional green light” turns on.

8. Identify Dilution Likelihood

If a company is cheap but has only 3 months of cash left, you need to build dilution into your plan.

  • The Runway Check: Before I buy, I check the cash balance vs. the burn rate. It doesn’t mean I won’t invest, but I might invest a smaller stake so I can protect myself.
  • Why? If they have to raise capital at a low share price, they dilute you. That raises the “floor” required to break even and kills your upside leverage. Again, I wouldn’t pass on the investment, but I am planning around it.

9. Don’t DCA, “Ape In” (as the kids say)

Conventional wisdom tells you to Dollar Cost Average (DCA). In asymmetric investing, DCA is a mistake.

If you have done your homework correctly, you have identified a stock that is trading near its valuation floor. The downside is already priced in. The spring is already compressed.

  • Why wait? If the stock is at the floor, every day you wait is a day you risk missing the launch.
  • The Strategy: I typically enter with 75% of my intended position size immediately.
  • The Logic: Since the probability of the stock going UP is significantly higher than it going DOWN (due to the asymmetric setup), “averaging in” usually just means you end up increasing your average cost basis as the stock rises.

Keep the remaining 25% in reserve just in case of a macro-market flush or a final test of support, but generally, when you see the hot table, you sit down.

10. Using the Chart

Fundamentals tell you what to buy. The chart tells you when. I never buy blindly. I look for Technical Confluence to confirm the asymmetric setup is ready to move.

  • Volume Spikes: I want to see institutional volume coming in. If the stock is up on light volume, I wait. If it pushes through resistance on massive volume, the “hot table” is open.
  • The Setup: I look for consolidation patterns (bull flags, bases) where price tightens. I enter my 75% position as it breaks out of that tightness, not while it’s falling.
  • Don’t Catch Knives: Even if the valuation is cheap, if the chart is in a structural downtrend, the “floor” might get lower. I wait for the reversal signal.
  • I use Gemini for all my Technical Analysis

11. Leverage with Options

This is where the strategy gets aggressive (and higher risk). Once you identify a high-floor asymmetric setup, I often look at Uncovered Calls (Long Calls).

  • The Logic: Because the valuation is already compressed, the likelihood of the stock crashing 50% is low. The “floor” protects you.
  • The Leverage: If the market wakes up and re-rates the stock from a 4x multiple to an 8x multiple, the stock price doubles (100% gain). But the call options? They can see 500% to 1,000% returns on that move.
  • Timing: This works best when the market hasn’t priced in the move yet. You are buying volatility when it is cheap.

12. Negative Asymmetry

Warning: This is what I see people get wrong the most. Just because a stock has huge upside potential doesn’t mean it’s an asymmetric investment.

This is the concept of “Priced for Perfection.”

If a stock is trading at 50x sales because everyone knows it’s going to take over the world, there is no edge. There is more risk here than people realize

  • Scenario A (They Win): The company executes perfectly. The stock goes up 10% because that was already the expectation.
  • Scenario B (They Stumble): They miss earnings by one penny, or guidance slows by 2%. The stock crashes 30% because the premium valuation collapses.

I don’t care if the company is going to cure cancer, if the valuation is already in the stratosphere, the math is against you.

13. Forget 3 and 5 Year Roadmaps

Investors love to ask: “Where will this company be in 5 years?” or “How will they possibly beat the market leader?”

My honest answer? I don’t care.

They don’t need to become Google to make you rich. They just need to revert to the mean.

  • The Math: If a company is mispriced at a $400M market cap but its revenue and growth suggest it should be trading at $2B, that is a 5x return waiting to happen.
  • The Catch-Up: I am not looking for the next “world beater.” I am looking for a mispriced asset that simply needs to “catch up” to its appropriate valuation to multiply my investment.
  • The Focus: This is about math, not storytelling. By the time the 5-year competitive landscape is actually settled, I’ve likely already sold for a 400% gain.

14. When to Sell

The hardest part isn’t buying; it’s selling. In this strategy, you sell when the asymmetry is gone.

  • Valuation Catch-Up: When your “cheap” stock catches up to its peers, or the P/S multiple expands to fair value.
  • Thesis Break: If the reason you bought (a specific product edge, a policy moat, or a unique capacity) changes, or if a competitor catches them, you sell. We need to be honest with ourselves. If the story changes, the math changes. Don’t hold onto a broken thesis hoping it fixes itself.
  • The Table Freezes: When the “hot table” goes cold, color up and leave.

Don’t fall in love with the ticker. Fall in love with the math.

Do Your Homework

In the end, none of this works if you don’t do the homework. Copying someone else’s investment when you haven’t done the homework is a recipe for disaster. If I had not done my homework on

$TE

I might have panic sold down 30% because I did not have confidence in my thesis or diligence.

Do your homework. Be responsible. Build a process you trust.