Own your mistakes

Josh Sherman
3 min read
Entrepreneurship

I fucked up recently.

Nothing that put any lives in danger, fortunately.

You see, I started doing a re-engagement campaign to reach out to all of my users that weren’t currently on my semi-monthly product update newsletter list.

This is actually something that’s come up quite a few times over the last year or so with some of my peers. Sitting on these emails was probably a gold mine. Low hanging fruit, they’d say.

It’s just that easy.

Well, maybe it could have been, if I didn’t fuck things up.

I thought I had crossed all of my T’s and dotted all of my I’s. I scrubbed my list with my own script. I paid to run the list through a cleaning service. I made sure to space out my sends and kept a close eye on my bounce and complaint rate.

Where I dropped the ball was on my copy.

I threw a post script in the email letting folks know that if you responded to the message I’d hook you up with a discount.

I completely failed to qualify the discount as only being available to users looking to upgrade from free to paid.

And of course I was hit up by a handful of already paying customers looking for their discount, most of which were already on grandfathered in pricing.

I sat on the requests for a short bit of time before starting to field the inquiries. A loss of revenue can really fuck with a small company, but if I’ve learned anything from my wife’s blog, negative press can be even worse.

Channelling my inner Jocko, I went full on with the Extreme Ownership and decided to honor the requests.

With that, without making things too difficult for folks, I explained how I fucked up and tried to find some concession that got them their discount, but also helped me out in the process.

For any customers that were on monthly, I offered up the option to switch to yearly in exchange for the discount.

Obviously this only works on folks already on monthly, so there were some folks that I couldn’t make that pitch to. For them, I hit them up with a customer survey with the 5 brilliant StoryBrand questions that easily translate into testimonials.

Not everybody filled out the survey, but nearly everybody I offered the switch to yearly to, took it. There was one lone individual saint that after I laid out the discount for going to yearly, felt their current rate was solid and didn’t want to take advantage of a small business owner like themselves.

The obvious lesson learned is that I absolutely need to qualify any future discounts, or the more likely scenario, never discount the brand like that ever again.

The less obvious lesson is that I should probably be trying to up sell monthly customers to yearly more often, especially since we’ve moved away from even offering up monthly plans anymore.

Even with a loss of annual revenue this week, by owning the mistake and trying to make the discount mutually beneficial, I was able to close out one of the highest revenue weeks of the year.

No more fuck ups for a while though, seriously.

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About Josh

Husband. Father. Pug dad. Born again Linux user. Founder of Holiday API, Backend Engineering Manager and Emoji Specialist at Mailshake, and author of the best damn Lorem Ipsum Library for PHP.

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