First time here? Start at the beginning → Chapter 1:

Does This Count as a Cease and Desist?

Forgot where things ended with the hooker? Read Chapter 4 for a refresher.

Well hello again! I’ll pick right up where we left off, yes — the gnarly details of the email from the hooker is exactly where the *almost* cease & desist came to me and Joe. Plenty more drama incoming!

By the time Chapter 4 was published, this blog was getting some attention, in the first couple of weeks (4 posts, around 20,000 views).

We had not heard from the seller for a while, which surprised us as we thought he’d have kept an eye on us… but he didn’t.

Finally, as is always the case with this saga… I wake up to drama. Eyes open, roll over, pick up my iPhone and look at my dashboard.

Oh shit.

This time it’s Joe calling me early in the morning. Recently missed calls from Joe starting at 6 AM (multiple calls), and 1 missed call from the seller.


In addition to calls, there were some love notes from the seller.

Want to see? I know the answer:

Does This Count as a Cease and Desist
Does This Count as a Cease and Desist

This isn’t quite a Cease and Desist, but also not a “Hey Guys, I don’t like what you’re doing — could we find a solution?”. This is the seller showing the warped world he lives in. Before calling my lawyer or Joe, I wanted to re-read all of this and digest it.

When we talked, our gut reactions were the same, this was a guy seeing RED, he wasn’t rational or realistic. That can be dangerous, so let’s assess the validity of the issues raised in the text.


  • Timing: You can’t be sued within ten hours of deciding you want to litigate. He’d need to consult his lawyer, have the lawyer write up a formal complaint, and that would need to be filed with the court. It can be quick, but a few days minimum.
  • Fabricated Claims: I’m not a fiction writer. You guys know what I do for a living. Why would I make this stuff up? I wish I was dreaming, but this is the reality.
  • District Attorney of New York: This guy doesn’t have any business outside of me and Joe in the State of New York. This one is total bullshit.
  • Divulging of Sensitive Information: This one has some merit, but it was on our email server (an asset we acquired), proves that the seller misrepresented several clauses in the purchase agreement and we redacted any sensitive information from the message. This one wouldn’t hold up.
  • Slander: We never mentioned him by name, but I understand his point. Again, we are not under NDA and everything we’re posting is kosher, it’s all been reviewed by our attorney.
  • Time Demand: No issue with that one.

This guy is erratic and clearly has never been in a lawsuit.

Right then, he began calling me at 7 AM. I ignored.

By 8 AM I was on the phone with my lawyer reviewing the situation when the seller called again, I ignored.

JG (as you remember from previous chapters), our lawyer felt it was best that we took the content down and focused on the rescue mission at hand.

Me and Joe? We felt that the seller had no legitimate beef and although he’d not succeed if we went the legal route — we didn’t want to add another responsibility to our plates. Replying to an official complaint that would come from the seller’s lawyer would require a lot of our energy, and we’d incur new fees that are earmarked for way more important stuff.

Decision made — no time for this nonsense…

Yes — we saved the business, the rescue mission is mostly done. But we’re not even close to where we want to be, we’ve got a LONG way to go. We took the high road and agreed that focus was the best thing for us. We’d let the seller win this round.

So… I pulled the posts offline, Joe made sure the seller knew our stance regarding our published content. Here is the reply to the above demand:

Does This Count as a Cease and Desist
Yes, I do drop my kid off at school regularly.

It was time to dig in even deeper into MailTag.

As our inboxes were inundated with emails from “blog fans” asking for more articles, a new wave of customer issues came up, a popular customer service ticket would read something like this:

I feel like my PING’s aren’t sending. Can someone let me know if it’s working?

What are PING’s anyway, and why are they important?

(replace this YT with the website PINGs on YT)

As you can see above, PING’s are quite a weapon. Personally, I wouldn’t use them much. I don’t do sales for a living anymore and don’t have enormous needs for email automation… Anyway, the voice of the crowd told us that it was a major draw to MailTag. We don’t want to drop the feature. We’ve already invested three weeks in our workaround and we haven’t yet had a breakthrough.

We hacked up a temporary solution to PING’s for our users, but it’s only meant to be a placeholder as we get the planned solution in order. It was barely passable, I’d rate it as a 4/10, we needed to get to a 9 or 10.

The team was stuck, we got on the phone and talked about a few different approaches. The next step was additional prototyping, and we had a different solution that no one had thought of prior. This one should take about a week to produce, and a couple of days of testing before we roll it out. My mood: cautiously optimistic.

After 10 days of development, the team is complaining about the inherited codebase giving them trouble (a lot more on this one in a future post). They are working around the clock, and we accept the fact that there is certainly some technical debt here.

Technical debt (also known as design debt or code debt) is a concept in software development that reflects the implied cost of additional rework caused by choosing an easy (limited) solution now instead of using a better approach that would take longer.

Another 10 days pass.

Does This Count as a Cease and Desist

Fuck. What a waste of time, effort and money.

This is where, as an entrepreneur — you can have dark moments. After getting punched so many times, naturally — you don’t want to get slugged again. To be very clear, we are getting our asses kicked on the technical side of things.

I found myself thinking back to the summer when we were making DidTheyOpen, our wish for a distressed company to come our way for purchase. The whole point was that it would be easier. My mind began racing back to June — wanting to point fingers and blame someone.

Who’s idea was this buying a company thing anyway?

Let’s check Slack:

Yep, my idea… Sorry Joe.

I had some flashbacks, and difficult questions continue to enter my mind, this is something all entrepreneurs deal with:

Was it a mistake to buy a company? Would we have been better off starting from scratch like our original plan? This is a nasty headache.

My answer? No. It was the right move. We are ahead of “zero”.

My next wave of neurosis kicked in:

Should we have re-built the entire system from scratch instead of patching it up EVERYWHERE?

We can’t afford to look into the past, let’s take stock on where we are at as a write this, both from a business perspective and a product perspective.

Business: October monthly revenue is pacing to land at around 2x expectation revenue from pre-acquisition. September was just a hair under our pre-acquisition MRR expectation, so we have done very well to recover revenue. We successfully saved and recovered a lot of the user-base, and acquired some new customers. Solid.

Product: Tracking and Scheduled emails, both functional sans Gmail OAuth API. A major victory. PING’s however, has proven to be more challenging.

Do we have another solution to PINGs? The team knows how I like my bad news to be delivered to me by now — with actionable alternatives. A new plan is presented, once again, the prototype looks good. We approve the plan (and last-ditch effort to save PINGs).

Engineering gets back to work….

Another 10 days pass, we are now at 2 months of effort on PING’s… we did NOT account for this. Remember our 40% price reduction from Chapter 3? Feels to me like we got ripped off, again. This one is on us, though.

Anyway — I digress… 🗣DRUMROLL PLEASE…

Does This Count as a Cease and Desist, drumroll

The team sends the message we were waiting for:

“PINGs are finished and on our staging server, please go ahead and test them out”.

(The Staging Server is the final testing ground before releasing the updates to the general public.)

We test heavily all day on a Saturday, and they work at a 9/10 level of user experience. Joe and I give the green light to release the updates to the live server, and just like that: We are officially full-featured and finally have the technology in the state that we thought we were acquiring. 🎉

What’s next? An angry ex-investor slides into DM looking for answers about the seller….and, did I file a police report for harassment?

See you next time ✌🏽


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