Kevin O’Connor & The Offline Assistant LOSE At The Texas Supreme Court

Finally some good news and common sense from the Texas Supreme Court.

Here’s a summary:

Timothy Castleman and Castleman Consulting LLC
v. Internet Money Ltd. and Kevin O’Connor
from Lubbock County and the Amarillo Court of Appeals

REVERSED AND REMANDED, per curiam opinion:
The issue is whether Texas Citizens Participation Act, which exempts actions based on certain commercial speech, applies in this defamation case involving a customer’s statements complaining about a transaction gone wrong. O’Connor sent Castleman a cease-and-desist letter demanding that Castleman erase and retract all online statements about O’Connor and his company, publish apologies that O’Connor found “satisfactory” and pay O’Connor $315,000. When Castleman refused, O’Connor sued him for defamation. Castleman moved to dismiss the suit under the Citizens Participation Act, asserting that the action relates to and is in response to his exercise of his free-speech right. In response, O’Connor argued that the act does not apply because the action is not based on Castleman’s exercise of his free-speech right and, even if it were, the commercial-speech exemption applies. The appeals court held that the exemption applies, so the Castleman could not seek expedited dismissal under the act. The Supreme Court HOLDS Castleman was primarily engaged in the business of selling goods, his allegedly defamatory statements did not arise out of his sale of goods or services or his status as a seller of those goods and services. Castleman made the statements in his status as a customer or consumer of O’Connor’s services.

So now the case goes back down to the appellate court in Amarillo Texas for them to rule on the remaining issues.

One thing to note – the Texas Supreme Court mentioned the following:

“Castleman intended his statements to reach O’Connor’s actual or potential customers. His statements constituted protected speech warning those customers about the quality of O’Connor’s services, not pursuing business for himself.”

I like the words “protected speech” about as much as I do the First Amendment.

You can read the full decision below:

Kevin O’Connor & The Offline Assistant LOSE At The Texas Supreme Court – Decision by Tim Castleman on Scribd

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Shit Happens

So I sent you a couple of emails.

One telling you how I almost killed myself

One telling you to calm your tits – that I’m ok

That brings us to now …

This is not the original message I wanted to send you.

I had hoped to be able to tell you about this subscription box company I’m an investor in.

It went from 0 to 1000 customers in less than 90 days. For less than $500.

If that sounds like the hook of a salesletter or webinar – it’s because it is.

Well, actually it was.

See, we had a deal – I’d pick their brain and release a course on what they were doing.

Good. Good. Win – Win and all that.

Then I decide to change the plan.

Instead of the course, now I want to offer ongoing support, monthly calls, work, work and more work.

The founder says no.

I press and ask for bi-monthly calls.

Just 90 minutes every 60 days.

No again.

I walk.

No course.

The last 3+ months wasted.

Back to square one.

So here’s the new message I want to share with you – shit happens.

That above story (which is 100% true btw) sucks. It means an estimated loss of 6 figures, a recurring revenue stream, and something I could plant my flag on and make a name outside of just being the notes guy (which I love and am honored to do) all gone and completely out of my control.

All over 90 minutes.

And because I refuse to sell you a course without being able to support it when something goes wrong or without current knowledge of what’s working today.

I would never do that to you.

So shit happens.

Plan A got shot to shit (more about that another time).

Plan B got vetoed

So now we’re back to square one, we’ve hired some help, and we’re getting back on the horse … until the next time shit happens.

Keep your chin up.

Everyone gets knocked down, we’re just the ones to stubborn to get up and try again.

I’m rooting for you.


PS: Dating sucks. Like the worst thing ever. If you hate being married, you’ll punch yourself in the face before enjoying dating. Don’t do that. That shit hurts. Then you have to go on a date with a black eye and explain yourself.

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Doom and Gloom

Last week I wrote you a pretty bummer email explaining how 2017 was the worst year of my life.

You can read it here if you missed it:

First I want to take a second to thank everyone who took the time to write me with words of encouragement.

To them and to you I say thank you for reading.

But I also wanted to share this – the year wasn’t a total loss because of what I’m about to share with you next.

One of the most surprising things I discovered after my wife left was photography.

Five days after she split I bought a cheap starter camera (the Sony a5000 in case you’re wondering) and started using it to capture various concerts I attended.

(You can see some of my shots here:

As silly as it sounds, this cheap camera and forcing myself to go to live shows with it, dragged me out of bed most days when my depression was at its worst.

This little fun hobby quickly turned into a passion project and before I knew it some of my shots were being featured on online blogs and in different industry news stories and I was traveling across the US to capture them.

Not bad for a guy who took a photography class years ago and still (secretly of course) has no idea what the hell he is doing 😉

Anyway, some of you might be saying what’s in this email for me and for you I have the second surprising thing of 2017 which was this:

I made an investment (no it’s not crypto related) a few years back in a small startup.

In 2017 this startup made a major pivot from selling one off products to customers to a recurring based subscription model where we just sell the same customers, the same thing, each month.

And wouldn’t you know it – that investment was one of the smartest things I’ve done.

I can’t share numbers yet, but it looks like my investment has paid off handsomely and will continue to do so month after month.

I’m actually meeting with the founder of this company very soon (this week or next) and they have agreed to answer any and all questions to the best of their ability.

So I figured I’d bring you in on the process as well.

Start thinking of any and all questions you’d like answered (you can reply to this email and tell me) because I’ll be asking for them soon.

Right now I’m off to the doctors.

Talk soon,


PS: BTW, this new subscription service was started in less than 90 days, for less than $500, and produced a HUGE ROI the first month. I’ll see if I can share actual numbers soon.

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The Worst Year Of My Life

2017 was the worst year of my life.

At times, I thought I was secretly writing a country song.

Other times, I just wanted to die.

First, at the start of the year, my dog died.

Then, on January 12th, 2017, I walked into a empty house and a two line “Dear John” letter that simply read “Tim I have made the decision to leave. I’ll email you about the hockey tickets for your birthday next week.”

And with that, my wife of 7 years (together for 10), was gone without warning.

I spent the rest of 2017 deeply depressed, spending at least 25% of the year in bed.

Days became weeks and weeks became months with me having zero motivation or energy to do anything besides sleep the day away.

When I wasn’t stuck in bed, I tried to lift my spirits, drown my sorrows, and anything else I could think of to try and shake the depression.

I burred myself in food, drugs, sex, and rock n roll trying anything I could to numb the pain and try to make sense of what had happened.

I spent a month overseas, several weeks on the road, a lot of nights out, and very little of it sober, hoping something would magically change and make the pain disappear.

In reality I was just trying to escape the pain.

Escape this empty house, escape the hauntingly quiet nights alone and the reality that my life would never be the same.

Anytime the phone rang or someone was at my door I wished it was her coming back.

It never was.

She was my reason for living, the reason why I pushed so hard for the things I did, so that we could one day retire and spend our time traveling the world together.

I white knuckled through a few nights in 2017 where ending it all seemed like the best solution.

I know the experts say it’s a permanent solution to a temporary problem, but when you’re spending nights alone in a house that wasn’t built for you, re-reading every text, email, and social media post involving the two of you, torturing yourself with every memory and asking what you could have done differently, that light at the end of the tunnel gets darker and darker still.

To make matters worse everything else suffered in my life as a result of my depression.

– My health took a major decline
– For several months I became a shut in, to the point that my doctor asked me when the last time I saw the sun was and I couldn’t give him a date
– My other relationships (friends, family, and business) suffered because I lacked the energy to do anything else but just keep myself alive
– I tried to spend my way out of depression. I tell you more about this another time, but tl:dr – it didn’t work
– Overall, business FUCKING SUCKED.

Like really sucked.

Overall business was down because I just didn’t have the energy or motivation to give a fuck about anything, including myself.

Seriously, at times I had to bribe myself with trinkets just to stay alive, so coming up with the next big thing or following whatever fad (Cryptocurrency ring a bell anyone) wasn’t happening.

Despite that, I still had (and have) tremendous guilt for not really being able to be here for you, my staff, or anyone else last year.

With all that being said, here’s what I want you to understand (and I’m writing this to myself as much as I am to you):

#1. You made it. If your 2017 rocked, congratulations and I hope you keep on kicking ass and taking names in 2018.

However, if your 2017 sucked big harry donkey dick balls like mine did, the good news is we’re both still alive and able to make the changes necessary to live a better life from this point forward.

#2. Growth comes from pain. I wouldn’t wish last year on anyone and I’m still dealing with the fallout from it this year. But, I didn’t die, and I know that in time (and if I do the work required) things will get better. I’ll learn from this, process it, and move on and improve my life because of it.

#3. Silver linings. After my wife abandoned our marriage I first let a small group of online friends know. Their messages, phone calls, text and emails at time breathed oxygen into my body when I felt I couldn’t go on. My local friends and family did the best the could to help me and my staff (and even several of the companies I work with) did everything they could to support me during the year.

When I finally went public (or at least Facebook official) about her leaving me, the outpouring of messages and support was like nothing else I had experienced in my life.

And even though everything seemed to go to shit business wise around me, there was one thing that happened to me (maybe it was dumb luck) that will change the way I do business forever, starting this year.

I’ll tell you about that when I find some more motivation and energy to write.

For now, I just wanted to say hi, give you an update on why I’ve been so quiet and share a little bit of what’s been going on behind the scenes.

Until next time,

PS: I’m ok by the way, or as ok as I can be right now.

I’m in therapy, on some new fancy head meds for the depression and trying to slowly get my life back together by staying home and working on my depression instead of traveling so much.

I still feel like I’m at the beginning, sometimes the grief and memories overwhelm me, and there are still days I have trouble getting out of bed.

For now, I’m just taking it one day at a time.

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Ep 53: Two Drink Tim

Tim Castleman returns and tell you about a sudden death, the end of an 11 year relationship, abandonment issues, previews his new Alicia Castleman voice and so … so … so much more

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Texas Supreme Court Appeal – Castleman Consulting Appeals The Offline Assistant Million Dollar Lawsuit Against Us

We battle on!

This time to the Supreme Court of Texas where I am asking them to throw out the million dollar lawsuit Kevin O’Connor and The Offline Assistant have brought against me.

We filed our petition and today we received word that the court is asking Kevin O’Connor and The Offline Assistant’s legal team to file a response to our petition.

They have until September 5th, 2017 to do so.

The Offline Assistant, Kevin O’Connor vs Castleman Consulting LLC by Tim Castleman on Scribd

If you’re unfamiliar with the case, or why we are being sued for a million bucks, you can read everything here:

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American Airlines Flight 3595 Issues

Today I was suppose to fly out of Lubbock (LBB) on American Airlines Flight 3595 to Dallas and then AA Flight 2583 to Detroit. When I went to check in today, I paid an addition $100 to fly first class to Detroit on top of the additional money I had already paid for an economy plus seat (aka no middle seat).

When I checked in the two previous flights showed delayed but my flight, 3595 was showing on time in the airport, via the app, and on the board. Around the time our plane was suppose to board – 5:45, the previous flight had just landed and started boarding so I went to the desk to ask for a flight update.

There was a plain clothes employee there who said that my flight (3595) was now delayed until 7:20 and that I would miss my flight to Detroit as a result. He said I could go to Dallas, but I’d have to stay in Dallas on my own dime because the delay was weather related. When I asked more questions, he said he had to go, grabbed his backpack, scanned his plane ticket and boarded the plane.

When the employee finally finished checking in the previous flight he set out to “help” me. He said he could get me to Detroit by way of Dallas, then flying to Phoenix, and taking the red eye to get me into Detroit at 6am.

When I told him that wouldn’t work, he rescheduled me for a flight 5785 the following day at 8:15am the following day and then flight AA 43 to Detroit. When I asked if he was rebooking me for the same flight I paid for (First class), he said no that the flights had been checked in full for first class and that he wouldn’t be able to get me the same ticket and that I should get a refund for my extra seat purchases (both first class and economy plus).

What he didn’t tell me is that he booked me in a middle seat for my flight to Detroit.

So I went from FIRST CLASS, to an economy middle seat and being told there was nothing more they would do for me.

So I called your AA reservation number and talked with Tanya. Actually that’s not true, I called, got placed on hold and then had to wait 30 minutes for a call back from her.

When we talked she said the following:

Because I had already checked in (I hadn’t) for the flight, she would need to cancel all my tickets and start over. So she did.

But, then when she did that she said the plane tickets were in control of the airport and she could not assign me any seats and I’d have to wait til I showed up to the airport to get my seat assigned.

The problem is, I already had my seats assigned from the gate agent – including an exit row seat from Lubbock to Dallas and now I have no seat assignments.

I went from an economy plus, then first class to a middle seat, and now unknown.
I had an exit row seat for my flight out of Lubbock (5785) and now I have nothing.

And here’s the best part – Tanya told me that I HAVE to call you guys after my flights to get a refund for my extra ticket and first class purchase even though you guys can’t honor my ticket.

That’s right, I have to do the work for you to give me back my money because you can’t fly me the way I paid to be.

This is on top of the now 1.5 hours I’ve spent on hold and calling or waiting for call back from your travel center.

So AA, explain to me how this is fair to me, the customer.

I paid for my flight, I showed up on time, NO ONE notified anyone in the airport about the delays until it was too late to be put on the earlier flight. Then I had to be rebooked the following day, in the morning, with no guaranteed seats and the ones I did have are now gone due to your ticket agents error.

So tell me, is this how American Airlines responds to these issue? I called your reservation desk, they can’t help, the ticket desk can’t help or refund me my money.

So I don’t want to hear you’re sorry, I don’t want an apology, I want to know what ACTIONS you’re going to take to make this right for me as a customer?

At a minimum I want all of my money refunded for the extra seats I bought (economy plus and then first class), I do not want to do a middle seat for my flight to Detroit, and I expect some type of compensation for my time and frustration of having to deal with this.

Original Flights:
LBB to DFW: AA 3595
DFW to Detroit: AA 2583 – Economy Plus, then First Class

Gate Agent Change
LBB to DFW: AA 5785 – Exit Row Seat
DFW to Detroit: AA 43 – Economy, 22D Middle Seat

Reservation Agent Change
LBB to DFW: AA 5785 – Seat Unknown
DFW to Detroit: AA 43 – Seat Unknown


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The Best Thing I’ve Bought In 2017 – Marketing In Your Car Podcast

This is the best thing I’ve purchased in January 2017:

As soon as I bought it, I started to tear into the transcripts – because lets be honest who has 42.5 hours to listen to all the recordings :). I’ve gotten so much value from the transcripts that I spent my own money turning them into a full fledged kindle book for me to read through each morning.

Before I get out of bed, I simply turn on my e-reader and breeze through several episodes in a matter of minutes (instead of hours) and after each reading session my mind is buzzing with new ideas that I can start and implement quickly.

Here’s an example. In a recent episode Russell talked about taking your art (what you do) and turning it into a science (a predictable and repeatable pattern). In the episode he gave several actionable steps on how to do this and even explained how he used this same process with his Inner Circle members and to write his first book.

Minutes after reading about this, I had my own plan and process laid out to share with my team to get the same results that he did.

All that from a single episode.

And that’s just a single thing I picked up from the 257 lessons Russell Brunson shared here:

Life, business, time management, team building, scaling, success and yes, even the failures.

Where else can you learn from a guy who has been battle tested over the last decade and shares openly about the highs and lows of running a million dollar business for so cheap?

So here’s my advice to do – buy the MP3 player – and then throw it away. <shocked face>

Yes, I’m serious, because for me (and I bet for you) the hidden gold are the transcripts.

Not only will they cost you next to nothing – they’re something you can take with you anywhere and read whenever you need a boost, some direction, or just want to get your mind fired up.

To make it even easier, anyone who picks up a copy of the transcripts, just post below and I’ll send you a copy of the kindle book I had created out of them.

That way you can read them on any device at any time AND you can take notes, make highlights, and more so you can really use and absorb this information.

This has been one of the best things I’ve purchased this month and I can’t wait to see how it impacts you and your business as well.

Grab yours before midnight tonight (1/31):


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Tell Me Already

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Castleman Consulting Appeals The Offline Assistant Million Dollar Lawsuit Against Us

Here’s a legal update on The Offline Assistant & Kevin O’Connor’s million dollar lawsuit against us.

We have appealed the ruling made here in Lubbock to let the case continue.

Here is our appeal paperwork, filed with the courts in Amarillo Texas.

Castleman Consulting vs. The Offline Assistant Appeal Paperwork by Tim Castleman on Scribd

Once we filed our paperwork, Mr. O’Connor’s legal team requested and received a 20 day extension and at the end of that extension, they filed the following response.

The Offline Assistant’s Response To Our Appeal Request by Tim Castleman on Scribd

After their filing, we were granted an additional 20 days to file a response to their response (confusing I know). Here it is.

To me (as a non lawyer, with zero facts supported and purely 100% opinion based) – my lawyers did an excellent job with this answer and it addresses several real and possibly false statements made in their filing against us.

Castleman Consulting LLC Reply To Offline Assistant’s Appeal Paperwork by Tim Castleman on Scribd

For those needing a quick recap, read the various blog post on the topic but here’s my 100% opinion based timeline of events:

Nov 2015 – We notice almost 8k in over ordering by Kevin’s company The Offline Assistant. We double check our numbers (by pulling credit card statements, orders) and give Kevin several opportunities to settle with us for less money (5k at one point) but refuses to accept fault and eventually he stops answering my emails.

Dec 2015 – I send a legal demand letter asking for repayment.

Dec 2015 – Kevin’s first lawyer responds and instead of settling, he wants us to remove all of our content, write a public apology (that Kevin as to approve), and pay Kevin $315,000 in damages. This is less than a month after we discovered the error.

Mar 2016 – Kevin officially sues us (making all of this public record), but now he’s got a new lawyer, and wants up to a million dollars in damages.

Aug / Sept 2016 – Kevin begins having our content falsely (my opinion) blocked in Ireland and when I reach out his lawyer asking him to stop, he doesn’t. As a result, I have no other option but to repost the videos and provide updates on each one via various social channels.

Oct 2016 – We appeal the Anti-Slapp case to the Court of Appeals in Amarillo Texas.

Early Nov 2016 – Kevin’s lawyers file for an extension and push the appeal deadline to the 30th of November.

November 30, 2016 – Kevin’s lawyers submit their paperwork opposing our appeal.

December 19, 2016 – We file our response to their opposing paperwork and now await the appellate courts decision.

By the way, once we received notice of their failed attempt at a temporary restraining order, I personally reached out to Kevin and gave him one last chance to settle with us before allowing the courts to decide our fate.

How was this offer received by Kevin? His legal team sent over a second request for another temporary restraining order that as of today (1/9/17 @ 4:06pm) I have yet to receive any legal notification to stop posting these updates or contacting Kevin himself.

So now we wait for the courts to decide and all previous offers of settlement by me have been taken off the table.

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