How Self Doubt Cost Me $18,000

Published about 1 year ago • 5 min read

Hello there. Tim here.

We started watching Ted Lasso last night. I hope it lives up to the hype.


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1 - How Self Doubt Cost Me $18,000

Throughout most of my life, the voices in my head have told me things like "you can't do that", or "you're not good enough", or "no one cares what you have to say."

I've built my confidence by forcing myself to do hard things and then through trial and error, I've discovered that I am capable of more than I thought. Believe me, it has not come easily. My default is fear and self doubt.

These days, I consider myself a confident person, but that's not to say that I breeze through life without self doubt and limiting beliefs. I regularly catch myself saying things to myself that I would never say to another person.

And these insults come at a cost.

This week, I will tell you a short story about how my self doubt cost me money and opportunity.

Getting Sponsorships for the Pod

As you know, I have been recording a weekly podcast for the better part of two years. The pod has been growing and it's one of my favorite projects.

Ethan and I have been exploring ways to turn it into a business. As of now, we have yet to monetize it.

Why not?

I am discovering that the reason I haven't monetized the show is because I'm scared.

The voices would say "no one wants to sponsor your show", or "just keep this is a hobby because you'll get rejected and embarrass yourself."

I have cost myself tens of thousands of dollars. If we sold just one sponsorship per show, we would have generated around ~$36,000. Split that in half between Ethan and I, that's $18,000 that I missed out on simply because I've been afraid.

Another Monumental Lesson

Recently, I struck up a conversation on LinkedIn with a young lad named Darren. I hired Darren's company to sell sponsorship deals for the podcast. (Just what I'm looking for).

Within a few days he put together a sponsorship deck and put other materials (such as a loom video describing the metrics of the show) together as a media kit.

You can see an example of one of the slides below.

Then, he sent me a spreadsheet of all the people / companies he thought would be a good fit to sponsor the show.

When he sent me the list, I was taken back, because the list was full of CEOs of multi million dollar companies.

Most notably, there was a company called HypeFury, which is one of my favorite products that I use every day.

Okay now listen up, because this is the important part of the story.

I said "damn you really think HypeFury would sponsor the show?"

He says "absolutely, you are a perfect fit."

I replied and said "How's that work? Do you submit the slides to the sales department or something?"

He says "No, I search for the CEO on LinkedIn and I message him and then I find his email and I send him an email."

I said "whhaaaaaaaaaahhhhtt????"

And Guess What? He Responded and Said He May to Sponsor the Show in Q3.

HypeFury would be a dream sponsor. I use the product every day. I've talked about it many times on the podcast and I can personally attest to how valuable it has been for my life and my business.

All this time, my dream sponsorship deal was simply a LinkedIn message away.

But my inner dialogue told me otherwise. My tiny voice of self doubt convinced me that these people were more important than me and would never respond to me and I painted this image in my head like I would be bothering them.

Come to find, he's not only interested but excited.

Don't Let Your Stupid Brain Trick You Into Thinking You're Not Good Enough.

Better to try and fail than never try at all.

However, I think you will find that trying and failing will actually lead you to the success you're looking for.

That is, is you're brave enough to ignore the voices in your head.


2 - When to Charge For Your Content | Subscriptions, Newsletters, and Membership Sites

This week, Ethan and I talked about content monetization and exactly how you should think about selling subscription products.

Ethan taught me so much this episode.

Most notably, he had an amazing insight as to the difference between personalities, entertainment, and education. It was brilliant.

We also spoke about ...

  • my idea for a membership site
  • how to position your membership site for sales
  • why membership sites are so profitable
  • how to create the ideal sales funnel

Click here to listen on iTunes and click here to listen on Spotify.


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4 - How I Went Viral on Twitter (It's Not What You Think)

This week, I posted my most viral piece of content ever.

As of right now (5:14 AM on 3/24) the Tweet reached nearly a half a million people.

How did I do it? You'll be surprised by the answer.

Click here to watch the full video.


5. Final Thought - "Companies vs. Investments"

Last week, I received a great piece of feedback about my newsletter.

Someone replied to the email and said ...

"You say you help people build multiple streams of income, but it looks like you spend all your time on the same companies. Where are the multiple streams?"

It was great feedback and it's something I will incorporate more into my content.

Here's the deal ...

There is a difference between having multiple businesses and multiple income streams.

It's not realistic to try and run multiple companies.

In order to create multiple streams of income, you need other people to run companies for you.

Here's a breakdown of my time

  • The majority of my days are spent writing proposals and closing deals for Stodzy. Without Stodzy, everything else falls apart.
  • I dedicate the other half of my time to running Copyblogger. However, my employee Stefanie does almost all of the work and my job is to manage The Copyblogger Academy. (I almost hit 1000 members!)
  • Fridays are my "fun days", where I write my newsletter and record the podcast.
  • That's it, every day, day after day.

Throughout the day, I am constantly fielding messages from my teammates who run other companies. Sometimes, I buy these companies out right and hire other people to manage them, and sometimes I invest into an already cash flow positive company.

Currently, I have 13 companies in my portfolio, automated investments in the stock market, a rental property, and a team of amazing people who are all working hard to build amazing products and services.

To be a good investor, you don't need fancy graphs and you don't need to be a math wizard. You need to understand people and you need to know how to incentivize people to do work that is beneficial for everyone.

That's how my money works for me.

I will write about these other companies more often.

Thanks for the feedback.

Love you guys. Talk to you next week.

Tim

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