Hiring feels a lot different when it’s your own money

I recently posted a part-time marketing job description to help me with a bunch of tactical stuff for Toofr.

I need help writing, SEO position tracking, supporting customers, and generally moving the ball downfield on all of my websites.

I posted on Craigslist, HireClub, and Remoteok.io. Over the last few days I received about 50 emails and set up calls with a dozen of them. I’ve asked two of those people I called to do a SEO assignment for me as a final step. I’m currently waiting to hear back.

It’s been a nerve-wracking experience. Here’s why.

I feel really sensitive about compensation. The rest of the process was, for the most part, by the hiring playbook we developed at Scripted. We simply offered market rates, maybe a bit lower, and that was that.

The reason I feel differently now, of course, is obvious.

At Scripted, and this would be true for any venture-backed startup, you’re not really spending your own money. If you make a mistake, it hurts, but it doesn’t impact your own paycheck. You shrug it off and try again, careful not to waste any additional time and money.

With Toofr, it’s not that simple. The money I’m paying to this marketer is coming directly out of my paycheck. It’s basically like I’m opening up my own wallet and paying them.

I’ve hired contractors before but that was before Toofr became my main source of income. When it really was just a side project I felt more generous. I cared less and, frankly, I didn’t have a choice. I needed the help because I was at Scripted all day and if Toofr broke I needed someone else to fix it.

Today I can do everything but it’s probably not the best thing for me to do. I need to specialize if Toofr’s going to graduate into the $30K MRR club.

When you’re bootstrapped the stakes are higher. Hiring the wrong person is not something you can just shrug off if you don’t get right.

This time it’s much more personal.

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