Three contrarian moves that start with a Post-It, not a prediction: barbell cash, ugly-duration buys, and a deliberate anti-round.

The Post-It Rule: ring-fence cash, then go hunting

I keep a stack of Post-It notes in the inside pocket of my laptop bag for one reason: when a financial setback hits, my brain wants to turn the whole situation into one big, dramatic decision. New plan. New thesis. New everything. That is exactly when I try to force a tiny constraint onto myself.

Here is the rule I write, in Sharpie, on a single note: “This cash is not an investment opinion.” Then I pick a number and ring-fence it. Not “some” cash. A specific amount that is boring on purpose. If I was running a small operating budget, it would be 6 to 12 months of burn. If I am personal, it is the money that keeps my mortgage and insurance from becoming a second crisis. That note goes on the inside cover of my notebook, the one I open in board meetings. It is visible. It stops me from reaching for the wrong lever.

Only after that do I do the contrarian part: I separate “I need to feel safe” from “I need to make money.” The setback usually tempts people to either freeze (100% cash) or swing for the fences (all-in on whatever is down the most). The Post-It forces a barbell. One end is dull: T-bills or a government money market fund. The other end is hunting ground, and I treat it like a deal screen from the top: what is mispriced because others have constraints I do not have? Who has redemptions? Who has a maturity wall? Who needs a buyer by Friday to avoid a covenant problem?

This is the part that feels different from armchair advice. The “hunting” list is not a mood board. It is a short sheet with three columns: forced seller, time pressure, and what I can underwrite without lying to myself. I have literally done this in an airport lounge after a rough capital call, notebook open, Post-It staring at me, and it kept me from turning liquidity into therapy.

Buying ugly duration when everyone wants short and clean

After a setback, the default instinct is to shorten everything. Short-term bills, short-term contracts, short-term commitments. I get it. You want optionality. But if the whole room crowds into “short and safe,” the mispricing tends to show up in the stuff that is longer, messier, and harder to explain in one slide.

I am not talking about making a heroic rate call. I am talking about hunting for duration that is accidentally cheap because it became socially unacceptable in the last twelve months. The most common example I see: good businesses with longer-dated cash flows that get punished when the discount rate rises, even if their actual operations did not deteriorate. Another one: credit instruments where the headline looks scary (lower-rated, longer maturity), but the structure or collateral is better than the label suggests.

From the top, this is where you stop reading headlines and start reading documents. I pull up the actual maturity schedule, not the marketing deck. I want to know: when is the wall, who owns the paper, what happens if refinancing costs 200 basis points more than plan? If I cannot answer those without hand-waving, I pass. If I can, I size it small and insist on a margin of safety that is a number, not a vibe.

The contrarian move is not “buy long-term because it is contrarian.” It is buying long-term selectively when you are being paid to accept duration that others cannot hold due to mandates, redemptions, or quarterly optics. You can feel the optics pressure in the language people use: “We just need to de-risk into year-end.” That is code for forced behavior.

I have done this with boring tools, not exotic ones. Investment-grade bonds trading at discounts because nobody wants to explain mark-to-market pain, and even certain preferreds where the structure is plain but the market has thrown them into the “avoid” pile. If you are operating at a high altitude, you are not trying to win the argument on Twitter. You are trying to buy future cash flows at a price that makes you comfortable being early and quiet.

The anti-round: invest to avoid the next raise, not to chase the last

Here is the most useful contrarian strategy I have watched entrepreneurs use after getting punched in the mouth financially: they stop optimizing for a great next round and start optimizing for a world where they never need one.

I call it the anti-round, and it shows up in tiny, unsexy decisions. Instead of adding headcount because “we need to look like we are growing,” they re-cut the org chart so one strong operator can run a whole lane without three support hires. Instead of expanding into a second product line, they delete it and push the flagship until margins are undeniable. Instead of a fancy rebrand, they fix activation in the first five minutes of the product, because that is what moves retention, and retention is what stops you from spending like a desperate person.

From the top, this is a capital allocation move, not a motivational one. You are essentially investing in runway extension the way others invest in growth. That can mean paying down a line of credit that has ugly covenants. It can mean buying out an expensive service contract early to lower monthly burn. It can mean paying for a migration off a vendor that is quietly taxing you every month (anyone who has stared at a ballooning AWS bill knows the feeling). None of that feels like a “win” on demo day. It feels like plumbing. And plumbing keeps buildings standing.

The hands-on tell is how the CEO talks in the room right after a setback. The ones who are about to recover start asking for a simple dashboard: cash balance, weekly net burn, gross margin, and one leading indicator tied to demand (pipeline velocity, trial-to-paid, whatever is honest for the business). Then they make one or two deliberate bets that reduce dependency on outside capital. The ones who are spiraling start asking for a new story.

If you are investing alongside them, this changes how you underwrite. You are no longer only buying upside. You are buying independence: a business that can survive a bad market and still be around when valuations normalize. It is contrarian because it is boring, and boring is often where the opportunity hides after everyone has been humbled.