Restraint Is the Skill You Were Never Trained For

Most founders expect the sale itself to be the hard part: the negotiation, the diligence, the months of waiting for it to close. What blindsides them is the quiet that comes after. The deal is done; suddenly, nothing has to happen today, and they go and do something anyway.

It shows up in small ways. You check the portfolio before your first coffee. There's the friend's deal you take a call about, the banker's fund pitch you let run longer than you meant to. The money is parked in cash while the lawyers finish the structuring, and the parking is the part that nags, as if every quiet day is one you're wasting.

It looks like a discipline problem, a failure of restraint. It isn't. It's the engine that built the company, still running flat out, with nothing left to drive.

Making money and keeping it are opposite skills

Building a company is all about doing. You move first, you decide fast, you back yourself when the evidence is still thin, because if you wait for certainty, you've already lost. That bias to act isn't a flaw in a founder. It's one of the reasons there was a company to sell at all.

After the exit, the opposite is true, and almost nobody warns you. Looking after a large pile of money is mostly about what you don't do: the drop you don't panic-sell into, the hot fund you pass on, the position you leave alone for a decade so it can grow. It's closer to a defensive game than an attacking one, and most of the value comes from the mistakes you manage not to make. That's an odd thing to be good at when everything in your career so far has rewarded the opposite.

Knowing all this doesn't make the urge go away. The pull to act isn't a thought you can talk yourself out of, it's closer to who you are. Every move a founder makes is a small vote for the kind of person they are, and most founders have spent a decade or more voting, every day, for the one who does something. So you can read all of this, agree with it, and still feel your hand drifting toward the deal, because the part of you reaching for it isn't the part that read the argument. The drive that built the wealth doesn't switch off on command. You don't think your way out of it. You wait it out.

What the restless founder pays

All that motion has a real cost, and people have been measuring it for decades.

Two economists, Barber and Odean, went through the trading records of 66,465 households at a discount brokerage in 2000. The most active traders earned 11.4% per year, compared with a market that returned 17.9%. Same market, same window, and the whole gap came from their own trading. The study is 25 years old now and has been repeated so many times that it reads less like a finding than a rule: trading a lot quietly taxes your returns, and the people most sure of themselves tend to pay the most.

The same thing turns up in the world a lot of founders drift into after an exit: angel and early-stage investing. The most thorough study we have on angel returns, even though it's well over a decade old, found exactly this. Investors who kept pumping money into bets they already owned averaged 1.4x over 3.9 years. The ones who spread their money around and resisted doubling down averaged 3.6x over 3.3 years. More money, in less time, from doing less. Most of the deals, around 56%, lost money, and plenty of them were wiped out completely. The returns that did show up came from spreading bets and staying disciplined, not from going all-in on the one you'd already fallen for. It's old data, but it's the best there is, because the real numbers are private and almost nobody refreshes them.

You can see it in founders who've been open about it. Cory Janssen, who co-founded Investopedia, spent years half-starting things and avoiding the real work before he found his feet again. Dan Berger, who sold his events software company, Social Tables, for around $100m, has said straight out that the money and the freedom made things worse before they got better. Neither was short of brains or cash. What they were missing was somewhere to channel the part of themselves that only knows how to build. I dug into why this happens in why smart founders make terrible investors: the same things that make someone a great founder, the conviction, the speed, the pattern-matching, turn into liabilities the moment they're the ones writing the cheques. The short version is that the skill that got you here works against you now.

Restraint, and knowing when to act

None of this means the move is to freeze. Doing nothing out of fear is its own way to lose, only more slowly. And plenty of founders should build again. The numbers on second-time founders are good: they hold on to more of the company, raise faster, give away less, and tend to get higher valuations. Something like half of all founders go again, and for a real builder, that can be exactly the right call. The trap on the other side is the founder who shoves everything into the safest options he can find, goes quiet, and slowly becomes someone with nothing interesting left to say.

So the real skill is telling those two apart. Before you put money anywhere, the honest question is whether the move serves your money and your life, or whether it only serves the itch, the need to feel like you're back in the game for an afternoon. One is a real decision. The other is the same old reflex, looking for somewhere to point itself. Most founders can tell which is which if they slow down long enough to ask. Slowing down is the hard part.

The patience doesn't come from waiting to wake up one day as a calmer person. You decide that sitting still is part of the work now, and you build a setup around yourself that makes waiting the easy default instead of something you have to fight every morning. The same drive that built the money is what protects it, and the trick is to aim it somewhere new: to be deliberate about doing nothing when nothing is the right move.

I'm not writing this from some calm place above it all. Most of my own money is locked up in one illiquid holding I couldn't sell tomorrow even if I wanted to, so the discipline I keep having to practise is the unglamorous one: leaving the part I can move well enough alone, instead of tinkering with it to feel productive. I boxed for years, and everything that was trained into me pulls the other way here, the urge to move first, to commit, to throw the punch. These days, the hardest thing I do is sit on my hands.

From where I sit

Something I run into all the time is a founder who's been liquid for a year or so, itching to put real money to work, asking whether that itch is a good sign or a warning sign. The honest answer is that the feeling itself tells you nothing. It's the same buzz whether you're about to do something smart or something daft. What matters is what's underneath it.

Sometimes it's the real thing. The cash has been sitting for a year, you've done the boring structural work, you know exactly what you own and why, and you've found one or two things you believe in enough to hold even when they're down 30%. That's not restlessness, that's being ready, and waiting any longer would be nerves dressed up as patience. Other times, the money's been sitting there, the sitting feels like failure, and the urge to deploy is mostly about wanting to feel useful again. That kind doesn't much care what it buys. It wants to move. When I catch it in myself, the best thing to do is usually nothing, at least not that day.

I get to watch both versions up close in my day job. Most of what we run for clients is long-term portfolios with a clear mandate, so we barely trade, we rebalance once a quarter at most, and otherwise leave well alone. But we also run money with an absolute-return target, and there the job is to hunt for the rare setup where risk and reward are well in our favour. Those show up maybe a handful of times a year. Spotting them isn't the skill. The skill is having the discipline to wait, because you have to stay glued to the market the whole time, watching other things go by and hearing about people making money elsewhere. The pull to pile into something you don't even rate, because everyone else is, and you don't want to be the one who missed it, is constant. And the ideas that pay are almost never the ones the whole crowd is already in. Tuning out that noise and then moving hard when you do have conviction takes more out of you than anything else in the job.

This is the part I'm still working on. I've got a business partner who's traded markets for more than 30 years, and watching how he waits, how he holds his fire through all the noise and then moves decisively on the handful of calls he's sure of, has taught me more than any book has. He's usually right. That patience is the thing I'm trying to build in myself.

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New on the Site

If restraint is the skill, the sheer number of decisions is what it's up against. The most recent piece on the site looked at why the first year after an exit throws up more big financial decisions than years of running the company ever did, and why the quality of those decisions drops even when the founder hasn't got any worse at making them. When every day brings another reason to act, doing less on purpose only gets harder.

Read it: Decision Fatigue Costs More Than Bad Decisions