Sell the Position

5 min readDec 30, 2021

This post is about the best lesson I learned this year. And to tell you it, I’ve got to tell you a story.

I got married this past fall — we luckily snuck it in between Covid variants — and my mind has decided to treat the whole thing like a giant Magic Eye poster. Nearly everything is blurry, but a few moments leap out when I concentrate. Those moments involve my closest friends, family, wife, and dog.

And… one random conversation I had with a stranger. Which is why we’re here.

During cocktail hour I was introduced to one of my parents’ friends who’d been way up at a bank and was since retired. She was sharp as hell, hilarious, and wildly intimidating.

When I’m intimidated, I default to asking lots of questions, most of which are bad.

“So… what was your secret?”

A textbook intimidated Brian terrible question, but she answered without missing a beat.

“Selling the position.”

I asked what she meant.

“People on my team were responsible for making money. The way they made money was through investment strategies — buying stocks or a basket of stocks or some other financial instrument that they felt was undervalued. When these positions were doing poorly, they’d have to defend them to me, and they would — tooth and nail.”

She took a dramatic gulp of cab.

“They always swore this tanking position was about to turn because of this reason or that. My job was to decide whether to give them more leash or cut bait. For a long time, I’d listen to each pitch and make case by case decisions, and our team performed fine. Middle of the pack. Until I came up with a much better strategy.”

She leaned closer and took an even more dramatic cab gulp, possibly overdoing it, but I was hooked.

“I told them to sell the position. To go back to their desk and sell every dollar of whatever they were defending. Then, I told them to go home. In the morning, if they wanted to buy back what they’d just sold, they could, and they wouldn’t have to defend themselves to me. But, 95% of the time they wouldn’t. Selling the position broke the spell. They suddenly had a bunch of money at their disposal and could see all the other strategies clearly. With unlimited options, they almost never chose the thing they’d owned the day before.

Our team consistently outperformed because humans always overvalue what they already own — they get emotional about it — and we were able to remove that bias.

The key to life is creating an environment that makes it easy and painless to drop the things that aren’t working fast.”

My new wedding friend was describing Loss Aversion.

We’re all hardwired to value something we own twice what it’s worth. If a $10 bill falls out of your pocket, you’ll be twice as upset about losing it as you’d be happy if you found a $10 bill on the street.

Loss Aversion isn’t a secret. We’ve all heard about it. But selling the position is an extraordinary way of combating it.

I built a dating app called Find Your Lobster back in 2011. It was similar to Tinder and Hinge, but a bit earlier than both. A lot of the work was good — even great — especially the branding and marketing. People still tell me how funny that lobster was.

But when Tinder and Hinge launched, we got steamrolled. They were superior products with better strategies.

I won’t get into why our strategy was bad, but it was. And as the ground shifted under our feet, it was clear to anyone with eyes that our strategy was a long shot. Well, anyone but me. I was blinded — captured by the spell of the great work we’d done, the good reasons we’d gotten into the space in the first place, and the strategy that had been creative and unique 18 months ago. I trudged along a doomed path for another year.

I should’ve sold the position.

But practically… how would that even work? I couldn’t just quit Find Your Lobster then start it back up the next day?

How to Sell the Position

It’s easy to be jealous of my banker friend and write off the strategy as something you can’t do. Selling the position and buying it back are easy when you literally have a position in a marketplace you can sell and buy in a day.

And, maybe most importantly, the metric of what she was trying to do was clear: the team existed to make money.

Over the last few months we’ve worked on recreating this strategy practically with founders in Tacklebox. We’ve found a dead simple way to execute on it.

It starts with two questions, a whiteboard, and (sometimes) a bottle of wine.

  1. What do you want?
  2. If you had unlimited options available to get that thing — would you actively choose what you’re currently doing?

What we’ve realized is just the thought exercise of thinking through what you really want and seeing if you’d choose what you’re doing to get there is enough to break the Loss Aversion spell.

Here’s how it would’ve looked with Find Your Lobster.

If I’d asked myself what I wanted out of Find Your Lobster, I would’ve quickly realized my passion was in building a business, leading a team, and being creative around marketing. Trying to turn an insight into a product is like oxygen to me. Find Your Lobster had been a vehicle for that, but I was passionate about the process, not the customer. I didn’t really care if my customers got dates, which is about as big a red flag as you can have as an entrepreneur.

And if I’d done the exercise of “selling” Find Your Lobster while I was building it, I would’ve never bought it back. The first question would’ve made it clear I needed to do something where I was passionate about the person I was building for. And, ideally, be building lots of things.

I eventually got to what I do now, but the exercise would’ve saved 12 months.

These questions are hard — thus the wine — but important.

And don’t be afraid to use them on a smaller scale and on non-work things. If you’ve been doing something — anything — for a long time, and it seems like the reason you’re doing it is just because you’ve been doing it, sell the position. See if you’d buy it back.

We’ve all got way too much to offer. No need to settle for something we wouldn’t choose.

If you’ve got a startup idea you want to go after the right way, Tacklebox is now a monthly subscription. Sort of like a gym + personal trainer for your startup idea. Tacklebox gives you structure, strategy, and network — the formula we’ve used to help 350 super early-stage folks launch businesses now worth over a billion dollars. It’s 40% off until Jan 31. More details here. Reply with questions. Now, back to the story.




We help founders with full-time jobs validate their startup before they quit. The posts are tactics we use.