A letter to into the abyss


My hope for you is that you read this without anger or judgement and an open mind.

How is it, that the business is going to do a million dollars in a single year and my personal business will do less than that yet I’m not the one currently struggling for money?

How is it that for the last two years, when I was stuck in bed with depression, or having to deal life bullshit, angry ex wives and bitter ex contractors, money wasn’t a major concern for me?

I haven’t emailed my list or even sold anything to them in months yet I’m not worried.

Hell I didn’t even take a single payment from our joint business until July.

Finally, how is it that you made $300k in PROFIT one year and the next year you needed to borrow money to keep from losing your house?

How is that all possible?

I’m not saying any of this to anger or shame you.

When I decided to invest with you, it’s because I not only wanted to help you (yes xxx, I actually do love and care about you and your family) but also I wanted to try and show you a different way of running a profitable business.

To you, getting health insurance and having the business pay for it is no big deal. Maybe you feel entitled to it, you work hard, haven’t had it in X number of years, etc.

To me, every additional cost you saddle the business with represents a larger monthly risk it must meet. You’re asking the company, that wasn’t profitable until just recently, to not only absorb your salary (plus the payroll taxes each month), but now also the health care cost.

It’s only an additional $7200 a year right now but as you know health insurance has been going up and up and up so who knows what it will be next year or the year after that.

All of this after one year of this new company, with minimal profit and growth.

So now the company has to make close to $6,000 dollars each month just to pay your salary and healthcare and that’s only to break even. If you raid the profits above that, then there isn’t enough money to cover that monthly cost in the slower months.

The bigger the monthly expenses, the more you have to work just to cover them and when shit happens (like the shirt business dying off, people suddenly quitting the box business, the seasonality of the summer – all of which you’ve experienced) you strain the business and if you put too big of a strain on it, you’ll break it and the next time you break it, it’s permanent.

That’s $18,000 in PROFIT you have to make the other 9 months just to cover your salary over the summer, let alone the cost of goods, fulfillment, etc of those normal months.

Whether you want to admit it or not, money management has been a huge issue for you and it’s the reason you needed to be bailed out in the first place.

You’re also the reason that after the bailout, the business bank account was down to $2500 (even though we agreed to keep $7500 in there) and when I showed that to you, you took an additional $1k out the next day.

To me that clearly showed either a lack of understanding of the situation or a lack of respect for my real world warning. It’s also the reason I had to prevent you from doing that again.

Yet when it came to saying no to you guys continuing to use business money to bail out your personal debts and put yourself out of business, suddenly I felt like I was dealing with children who were upset that I wouldn’t let them raid the cookie jar right before dinner.

XXX, if I had let you guys do that, you’d be out of business by now. There was no way you had the capital or personal savings to withstand those personal expenses being paid from the business account plus the slow months that followed.

Then where would you have been? What would you have done with no capital to invest in something new? What would have happened to you, your house, and your family then?

Seriously, stop and think about that. I know, I know positive affirmation and all that bullshit, but there’s a reason why I always plan for a rainy day, grow slowly, and I’m risk adverse.

Instead of seeing that, you and whoever else you’re listening to have decided that I’m the issue.

The guy who has made less profit than you have, yet doesn’t worry about money, is the issue?

The guy who has always tried to work with you, bailed you out in the first place and tried to find a solution to your issues, is suddenly is a huge asshole because he won’t let you do what you want, when you want?

Also, lets not forget, you owed me 5 figures in past due payments as well during all of this but none of that seems to matter to you, it’s only what I’ve done to you or said no to that seems to be the issue.

But instead of listening to me, you’ve just decided that you’re doing your own thing now.

We both understood the agreement. XXX profit split after the first few months of our agreement.

You were the one who changed that when you demanded a salary and then doubled it above our agreed amount.

You also changed the bookkeeper, the bank account, and whatever else you wanted because you wanted to have total control over the money and checkbook.

The same person who has repeatedly had issues with their personal finances, has admitted to not being able to keep the books up correctly, and twice had to ask others to bail them out of foreclosure wanted full control over the money vs the guy who has none of these issues?

You were the one who cooked up this whole co-ceo title and asked the business to pay an additional salary when we weren’t making any money.

Why do you need two people to run a business that has it’s fulfillment now 100% outsourced?

Because you don’t like talking to vendors on the phone?

And because of that we need to hire your family, full time, for an additional salary so they can call people vs an hourly employee who can do the same?

If we had done that when you wanted to, can you honestly say you’d still be in business?

Maybe you think – why does he get 30% of everything? He does nothing, hasn’t helped, and worse (based on your actions afterwards) won’t let me spend every penny in the account.

How dare I right?

You seem to forget that without that bailout, you’d already be out of business and there would be nothing to fight over because there would be no business.

You forget that me forcing you not to spend every last dime in the business account is the reason why you’re still in business today.

What am I suppose to do when you don’t want to do the things to help yourself out long term?

I hired a business coach, you wanted nothing to do with him.

I offered to make and market a course, but you didn’t want to talk on a regular basis to make it recurring project vs a one time thing.

I even sold you the shirt business back as a sign of goodwill, and still I’m the issue?

More for you, less profit for the business, more risk for the business.

You’d apparently rather listen to a mom who sells crystals online, or another one who had to get a 9 to 5 job because she couldn’t handle running a business or maybe you listen to your wife with zero business experience – all over me, your actual business partner and the one who had the money (and experience) to help you in the first place.

I don’t really know what the point is for this email is because I worry you’re unable change your perception of me or look at the meaning behind my message to you instead of the anger.

Maybe you just focus on the X% I get and not the X% plus salary you get? I don’t know.

But what I do know is how to run a profitable and sustainable business.

Instead of trying to take every cent out of the business, creating a huge monthly payroll expenses, and spend, spend, spend – look at the past pitfalls you’ve had and make a plan to overcome those.

Save a year of expenses (or even just start with 3 to 6 months worth), have a positive subscriber growth and a few years in the business to see what the ups and downs are (like last December) and THEN start taking the fruits of your labor.

This is your golden goose XXX, don’t kill it by asking it to lay too many eggs, too soon.

I really do want the best for you.
I really do still worry about you.
I am still here to help with my time and experience.

Where you go, your reaction to this email and what you do from here is your choice.

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Starting Again

Since last week I’ve received over 250 email responses (thank you for the replies btw) to me announcing that I’m heading in a new direction and want to dramatically change the way we interact and help each other.

Naturally, along with those emails, came your questions.

– How do I get started or start over?
– How do you prevent burnout and overwhelm?
– What opportunities do you focus on and which ones do you ignore?
– How to keep moving forward and actually accomplish your goals?

Your questions give me the perfect opportunity to preview how I to help you going forward.

So this Thursday, September 27th at 7pm CST (USA), I’m going to help you live and in real time to answer any and all of your questions.

For now, I’m referring to Thursday night as the first of our fireside chats and this one is on “Starting Again”

Here’s what you need to know about them:

1. Keep your wallet in your pants.

No fancy titles, no logos, sales pages or even slides. You get you, me, and 100% content only to actually help you and answer your questions vs a prepared presentation meant to just impress you.

2. This one is on me.

In the future, I’m going to charge $200 for these type of workshops, but this one is on me. Since it’s free, I’m not going to hammer your inbox with daily reminders to attend and I’m ONLY going to send out the replay via GoToWebinar so even if you can’t make it live to ask your questions, signing up now is the only way to get a copy of the replay.

3. You and your questions dictate the direction.

No prepared slide deck, no sales pitches, just you and your questions getting answered, your problems getting addressed and us working together to make a real impact on your life and business. YOUR QUESTIONS DICTATE THE DIRECTION, so bring them with you because I won’t be leaving until every question is answered.

You can sign up for Thursday nights Fireside Chat on “Starting Again” here:

Everyone that signs up will get a replay of the call and everyone that shows up will get their questions answered.

I can’t wait to hang out and chat Thursday night so we both can start moving in this brand new direction.

Again, this is 100% content, nothing is for sale, and this time it’s on me.

See you Thursday.


PS: For the “non-newbies” reading this, don’t worry I’m not just open to helping those just getting started. You can bring your questions too and I’ll be sending you a special email soon.

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When All Is Lost, Do This

Get yourself a hobby.


When my ex-wife abandoned our marriage without warning almost two years ago I was devastated (to put it lightly).

I went from having endless energy and excitement about life, business, and more to being lucky to stay up past 8pm.

My normal bedtime of 2am was replaced by 20 hours of non-stop sleeping, depression and thoughts of worse.

My entire world, and my “normal” day to day life vanished.

Lucky for me salvation came in the form of an after Black Friday sale at Best Buy.

Suddenly I found myself the owner of a super cheap camera (Sony a5000 if you care) and one really shitty lens.

Like, really really shitty.

But I showed up at The Bluelight and started taking photos of the bands as my new hobby.

I SUCKED, at first.

Seeing all of my photos after the first few shows made me want to puke.

They were dark, out of focus, needed editing, and more. To be nice, they were complete and utter dogshit.

Except to me.

Because to me, they were everything.

The shows (and the shitty photos that followed) kept me going.

One lens turned into two, then four, then many many more.

Every bad day I encountered seemed to matter less.

Where I had failed as a husband, friend, business man, and son – I found joy and excitement in photography.

When things got really dark and the thought of ending it all overtook me, I’d bargain with myself.

If I could just stay alive another week, well then I could buy or borrow this lens or that camera would to keep my heart beating.

Those trinkets and the bribes to keep me alive “just one more day” kept me steady when the world only seemed dark.

In time, my photos started to suck less.

Some even started calling them good.

I still secretly hate(d) 99% of them.

But none of that really mattered.

Those shutter clicks transformed into heartbeats and in time those photos started traveling around the world.

Album covers, tour posters, magazines, and more.

It’s apparently easy to get press when you work for free 😉

Again none of that mattered to me.

I wasn’t doing this for money, fame or fake internet points (although I’ll accept all of them), this was the one thing I could do to take my mind off of the rest of the world collapsing around me. The one thing I could do to see real growth, accomplishment, and improvement over time.

The leaps and bounds I had made in income and impact that now seemed common place to me online, I was now able to fully see and appreciate them though photography.

I’m currently writing this at 2am.

I’ve got photos downloading in the background, a stack of candy and diet coke next to me and a smile that you couldn’t wipe off my face or pay me enough to ignore.

I’m going to spend the next few hours (ok days) pouring over the 479 photos I took tonight and editing 10 to 20 of them.

If I’m lucky, I’ll see the sun rise across my face before I’m done. And I’ll still be smiling, full of joy and a feeling of accomplishment outside of the business world.

So the next time all seems lost.

The next time you don’t see a light at the end of the tunnel or a way out.

Try something new. Try something fun. Try something different.

When all is lost, before you give up, try this.

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This Got Chris’s Panties In A Twist

Oh no … it looks like my last email made Chris angry.
Now before I share my reply, let me tell you why this reply had me laughing.

First, Chris isn’t forced to be on my list or in my life.

Regardless of that, Chris didn’t like the fact that I’ve decided to focus on what matters most to me, even IF that means improving my overall happiness in life and how I run my business.

But here’s the ironic part Chris seemed to miss. I said 5 figures a month represents total freedom and the ability to enjoy my life how I wanted to right?

Well, if Chris had done some middle school math he would see that that means my WORST year would still be $120,000 ($10k a month for 12 months) and if I really busted my ass I could make as much as $1,188,000 ($99k a month for 12 months) just making 5 figures per month.

Apparently that’s not good enough for Chris and people like him.

To them, people like us, who choose happiness, success, and a healthy profit over burning out, 10xing it, and bitcoin bros (more like shitcoin last I looked) are underachievers.

If that’s true, well I’m here to say I’m a proud underachiever.

I guess if I wanted to get my ego involved I could have pointed out to Chris I paid my first house off at 31, I am debt free except for the new house payment, have sold millions of dollars online, and a bunch of other accomplishments that only make me feel better.

But I didn’t, because Chris forgot the most important thing I’ve learned in 2018 and that is this … I’m only interested in the people walking towards the light, not away from it.

I lack the time, energy, and frankly emotion I had 10 years ago (when I started online) to try and drag people kicking and screaming into success.

I’m done with having a ton of employees, fancy funnels, paid traffic this and that and all of the other complications I once thought I needed to add to my life because they worked for other people or I had to do the same as person X.

This new direction is simply what works best for me and I believe it’s one of the easiest ways to start and sustain an online business. Oh and you can also make a shitload of money for not a ton of work which to me sounds a lot better than 594 Facebook Ad Sets to make an additional 3 cents per transaction (ugh).

So if you’re like Chris, here’s my reply to him (and you).
I hope you have a great weekend with your friends and family.


PS: I’m well aware that Frank the Tank and Ed Dale had a course called underachievers. It turns out they sold that company to Russell Brunson a few years back which means I’ve now stolen the name from 3 different smart people. I’m not 100% sure, but I think that means it’s legally mine now.

If not, I guess Russell and I can wrestle at the next ClickFunnels event.

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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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