Start Up Bros, 10x Hustlers, & Gurus Should Leave

Another decision I made recently is that I plan to continue going against a disturbing problem I’m sure you’ve noticed the past few years online:

The problem of …
– Start Up Bros
– Software Kingpins
– Large Staff, Larger Offices, and a HUGE Payroll
– Hustle, Go In Early, Stay Up Late, Neglect Friends & Family in the process
– Launch A Product, Burn The List, Repeat Cycle

Now I’m not saying that route isn’t successful – it is and I’m sure you’ve seen its results.

But are you sure you know the rest of the story?

The massive payroll, the need to never stop working, the late night and forgotten weekends just to name a few issues I’ve seen.

And while I respect the giants in our industry (I’m looking at you ClickFunnels, Digital Marketer and many more) I have zero desire to be like them in terms of size, staff, and even yes sales & profit.

That’s right, I’ve decided that I don’t want to make every last dollar possible at the expense of building a life, business, or lifestyle I hate in the process.

There will be no 6am wake up calls, no TPS reports (quick, name that movie), no huge staff or army of outsourcers that I have to constantly pay and as a result have to keep coming up with the latest and greatest thing or shove another affiliate product down your throat just to make payroll.

Instead, I am working on simplifying things and keeping my expenses low, so I can enjoy life on my terms.

Because here’s the truth (based on 10 years experience and watching a few of my fellow friends make the switch) … there is VERY little you CAN’T do making a consistent five figures per month.

I know for some of you that seems impossible and for some of you that number represents a bad month.

But to me, that number represents total freedom.

To live the life I want, the way I want.

To take all the vacations I can handle, drive a nice car, live in a nice neighborhood and take care of all of my friends and families wants and needs oh and save a little for a rainy day.

Sure, I won’t be shooting a video from a helicopter, with my super model wife, and tricked out car collect anytime soon but I also don’t have deal with the stress and frustration those folks face.

So if you want to be the next Elon Musk, Facebook, Huge Fortune 500 company with a company manual, an HR department and more – maybe I’m not for you and you’d be better served by someone else.

However, if you’re interested in being a lean, green, money printing (and enjoying your life) machine then you’re in the right place.

If you want to live life on your terms, making or supporting things you care about, and enjoying life in the process – then you’re in the right place.

And even if you’re lost and only know what you DON’T want vs what you DO – well, I’m glad to help until you figure things out.


PS: Maybe I can’t help you, maybe I’m not the one you should listen to and take advice from. If you’re looking to become a software and info giant I recommend these folks.

If an agency based business or one that needs more strategic work – these guys have always treated me right.

Either way, I wish you the best on your journey and hope our paths cross again soon.

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Did You Win The Deadpool?

Remember a few months ago when I was telling you how much 2017 sucked?

Well 2018 went all “hold my beer and watch this ..” on me apparently because it hasn’t been any better.

If fact, it’s been a lot worse and that’s why I found myself “involuntarily retired” for most of this year.

“Involuntarily retired” is a fancy way of saying “totally lost, totally depressed and at times feeling totally defeated.”

That all changed last weekend.

How you ask?

Well, it involved a top secret trip, some of the best wings of my life, and trying to steal my phone back from a crackhead, at 3am, in another country.

More on that another time …

Here’s why this is important to you.

I’ve made some very tough decisions about my business going forward and I want to share the first few decisions with you today.

My first decision is, I’m taking 100% of my products offline to the general public in the coming weeks.

I’ve decided to remove every project I’ve worked on in the last 10 years from the net so that by the end of 2018, no one will be able to buy any of them again. I’ll explain why in a moment.

The second change I’m making is this – for the foreseeable future – I’m no longer promoting affiliate products.

I’m doing both of these things because I want to fundamentally change the way we interact and how I help you.

– More customer focused (on exactly your needs, wants and desires)
– Simplicity (not only from a customer support level but also on how I can help you)
– Making a real impact and change (no cookie cutter, one size fits all solution)
– More of a conversation, than shouting from on high

I’ll share more of my plans, thoughts, and ideas soon – but for now I just wanted to reach out and tell you that if you picked today for me to die in the deadpool, I’m sorry to disappoint you.

I’m very much alive and I’m excited to share what I’m up.

The first question I have for you is this – where is the best place to interact with you?

A. Facebook Group (OMG not another one)

B. Private Forum (1990s called and they want their sweater back)

Just hit reply and let me know which one you prefer. I’ll be here waiting for your answer.


PS: No, this isn’t the start of some high end group coaching (although there is nothing wrong with that). This is 100% happening with or without you and there is nothing for sale in this email. You’re welcome 😉

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Kevin O’Connor & The Offline Assistant Ordered To Pay Legal Fees

I didn’t notice this until after my last post, but the Supreme Court of Texas sent a judgement to the lower court stating that Kevin O’Connor & The Offline Assistant MUST pay me for my legal fees associated with defending my name and reputation with this lawsuit.

I will update you when and if he pays ….

Kevin O’Connor & The Offline Assistant ORDERED TO PAY by Tim Castleman on Scribd

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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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