One of the most important decisions you’ll ever make is the one when you say, “I’m pulling the plug — now.”

When you’re in the middle of the ambush you’ve lost the advantage. You’ve been set up on the enemy’s X, you’re totally f#@ked.

You have to get off the X and shift the advantage so the enemy’s plan becomes off-script.

Make sense? But let’s talk about quitting and failing.

I told you about the winners our company launched — the Loadout Room, the Arms Guide, Fighter Sweep, the Spec Ops Channel— but there were losers, too. I’ve stood up at least half a dozen new sites at Hurricane that haven’t worked out.

We created a site for military spouses called Military Posh. I still believe that space has potential, but at the time we couldn’t get it right, or at least not fast enough. My model is: start a site, do our best to build it, and if it doesn’t grow or we can’t figure out some way to monetize it adequately, then we kill it. Typically, you’ll know within six months whether or not a site is working. In the case of Military Posh, the page views just weren’t there and we weren’t able to get the sponsors we needed. So after six months, we shelved it. We might find the right sponsor at some point; it’s still there, and we could have it back online in no time. But for now, it’s mothballed.

We started another site, Transition Hero, a military-to-civilian transition advice and jobs portal for vets, the only one of its kind online. We had a sponsor for a while, but we lost them and didn’t have the manpower to maintain the site properly without any solid ad revenue. I really believe in that concept and have high hopes that we’ll find a way to bring it back at some point. But I had to yank it. As with Military Posh, we took a loss on that one, but it wasn’t huge, because we hadn’t poured a great deal of investment into it.

For a while, we had a site called Hit the Woodline, a satirical blog in the style of the Onion, about military life. This was one of the few sites that we bought as an already-existing property and brought under our umbrella. I paid about 15 grand for it, but we never found the right person to run it, so it, too, is sitting on the inactive shelf.

I spent even more on, which I bought for 45 grand. To be clear, that $45,000 outlay was just for the domain name. Once we owned it, we scraped the site clean and started over from scratch. This is analogous to buying a physical property for the land and road frontage, tearing the existing structure down, and rebuilding from the foundation up.

I worked with for a while, a site run by my friend and former SEAL Mark Divine. Mark is a great guy and it’s a fine website, but once we built the site and Facebook page to over a million followers, he took it independent again. I’ve tested out bringing other popular blogs into our network and monetizing them but found that a lot of these smaller site owners had unrealistic expectations and lacked business experience, which caused problems. They thought they were going to make money right away, and it just doesn’t happen that way. Eventually, I decided it wasn’t worth the headache and that we should stick to investing in our own properties.

My point here is that every single one of these sites was a great idea, and I could have easily kept them going for a lot longer than I did — they could still be going today, draining our cash, our effort, and our focus — if I didn’t have a strong belief in recognizing when something’s not working and calling a tactical retreat. Fast.

My six-month yardstick generally works well for our websites. This is in part because the ongoing operational cost is not that high; if you were keeping open a retail storefront, it might be very different. Every project has its own tolerances and critical metrics. You have to establish your own key performance indicators, whether it’s revenue targets, traffic goals, profitability (or the break-even point), or whatever matters most. Plus you have to decide ahead of time how long you’ll give it before you pull the plug. And then follow your plan.

You have to get off the X.


This article was originally published in March 2021.