The $0-$10K/Day Case Study: Day 183

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Day 183


Little column A, little column B.

One thing I’m learning about entrepreneurship is that the swing in emotions is fucking real.

Of course, that’s something you hear about when you read entrepreneurial books and listen to interviews with entrepreneurs. They all talk about the emotional swings you get and the highs and lows. Emotional swings are not unexpected going in, so it doesn’t feel like it’s going to hit you.

If you know it’s coming, then it should “soften” the blow.

It really doesn’t help.

A few days ago, I was crying randomly on my couch. Then, I had a really good and successful day where I felt like I was crushing it. Then, I had another day that went like shit and I was working from 6am to 7pm and was feeling like shit.

It’s just way too cyclical. It hits you and you don’t expect it.

I’m not sure how to best take care of mental health at this point, but I think the best goal is to take as much as I can from “unpredictable” to predictable.

For example, the consulting work has been extremely lucrative, but also highly unpredictable. It involves me constantly pitching new clients, and bouncing back and forth between different projects.

Yesterday, I had to join a meeting at 6am. That sounds early for a meeting because it is.

So, let’s get rid of unpredictable in favor of predictable.

I’ve worked two full-time jobs for greater than a year

I have my current full-time job and consulting.

Next year, I want to launch CCIO and double down on the website business. Those are predictable because, as my fiancee said, they are both work that is 100% under my control.

Here’s what I want to do then:

  • If I get the job that I want, then I’ll quit my current job and consulting. That will enable me to focus on growing the business and learning a new skillset
  • If I don’t get the job I want, I’ll quit my current job and keep consulting. That will give me an income while I start the business.

The constant is that the business will happen no matter what. The reason why is the business is what will allow my very good consulting income to turn into a recurring, stable income. I need to be willing to potentially sacrifice that stability in order to make a scalable business with recurring income.

Yesterday there were 1,51o days until I turn 30 and need to make $10K a day passively. Here’s how I spent it in pursuit of that goal

The current phase of the plan

I’m in Phase #3:  The Business Phase.  You can read more about the phases and my plan to get to $10K/a day at 30 here.

I still consult, and I still have a job. I’m looking forward to removing both of those ASAP.

Wake up & sleep:

I slept 6 hours and 29 minutes from 10:57om to 5:35am for a total recovery score of 62%. Not bad.


No workout at all; not even some abs or stretching. My day strain score was really high for not working out at a 15.4. I think that’s because I’m relatively stressed with the emotional swing.

Stress levels

Stress was probably a 2/5, with 1 being the highest. I didn’t randomly start crying, so I guess that’s a plus.


I had oatmeal for breakfast, Swedish pancakes delivered, coffee, bubble tea delivered, and then vegetarian indian food over rice for dinner. I spent money on delivery and it showed. It also was not healthy.

Not great.

My Day Job

This is actually getting really interesting.

The company is starting to ask me to do more work and is giving me disparate projects to work on. I’m happy to do so, but it thus far hasn’t really moved the needle for me. I still think the company isn’t well-positioned and well lead to achieve what it wants to achieve.

And, candidly, the talent agrees. The most experienced individual in the company just quit out of frustration with the company.

That’s now the third valuable employee to leave in the last ~60 days or so. I’m excited to see what is going to happen now that talent is running out the door. That’s not because I’m excited to see a company fail from a malicious perspective. I’m more excited to see what “failure” looks like so I can learn from it.

I’ve already learned one big lesson: the problem with this company is culture-driven, largely from the CEO. He changes his mind, condescends, and shifts priorities faster than you can count to three.

Lesson learned: fix the cultural issues if you want to have a successful company.

Investment real estate

We renewed the registered agent for the next year for one of our LLC’s. $120 bucks, and now we are protected for another year.

Nice and easy.

CCIO: My business

TBD on this for now. It’s coming in Q1 of 2021

Content website business

I plan on launching a business that makes money via online advertising. I essentially need websites, and a lot of them getting a lot of views per month.

My younger brother is actually bored at home and looking for a new project to work on. I might conscript him and sign him up to start writing some content for me on this website.

If I can get to him publish ~50 pages of content for me very quickly, that would be a huge win. I’d love to have him up and running on the content as soon as possible.

I need to flesh this thinking out a bit more.

Side Consulting

Same old same old.

Data Project

A couple of calls, some Excel work, and I had to make a powerpoint late last night. We’ll see what happens here shortly.

Presentation Project

I just started a one week project to help a company make a board of directors presentation. It should be an intense week, but a good week.

Sourcing new work

I had a big pitch call yesterday for a ~$75K project. I’m not sure if this is going to happen, but I really want it to.

$10K/day website

Daily post





Rescue Time Daily Screenshot

Standard day, full of a shit ton of work.

What I made today

Current Income  Streams

  • Job:  $170
  • Consulting for data project: $530
  • Presentation project: $400
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $1,165

Planned income streams

  • My Business (CCIO)
  • Ads on $10K
  • Content sites
  • Acquired businesses
  • Coaching

Today’s pro-rated amount of monthly & yearly expenses


Life Expenses: $89.73

  • Rent, utilities, Internet: $63.33
  • Phone Bill: $1.57
  • Health Insurance: $8.90
  • Ladder Life Insurance: $0.83
  • TrueBill for Budget tracking: $0.10
  • Car: $15

My Startup’s Expenses: $0.16

  • Bluehost Domain name: $0.16

Health Expenses: $4.20

  • Peloton: $3.20
  • Whoop fitness tracker: $1.00

Productivity Expenses: $2.25

  • SuperHuman to save time on email: $1.00
  • Rescue Time to keep me honest on my productivity: $0.20
  • Fantastical as my main calendar: $0.20
  • Evernote to track everything: $0.27
  • Grammarly to keep my emails looking okay: $0.38
  • BackBlaze to keep my files backed up: $0.20

Consulting Business Expenses: $4.80

  • Quickbooks to track expenses: $0.40
  • Google Business Email Account: $0.40
  • Fiverr for virtual support: $0
  • Hiscox business insurance: $4

$10K a day: $1.59

  • Kinsta for hosting: $1.00
  • Bluehost for domain names: $0.03
  • WP Rocket for speed: $0.14
  • Link Whisper for SEO: $0.14
  • Elementor for site design: $0.14
  • Astra for theme: $0.14

Real Estate Investing: $0.52

  • Legal Zoom Registered Agent (all LLC’s): $0.52

Today’s Income (pre-tax)

Topline of $1,164 spent $103, which means….

Made $1,062 (pre-tax)

My plan for tomorrow

Tomorrow is Wednesday, and I have to:

  • Couple hours of meetings for big projects
  • Build an outline for that powerpoint client
  • Follow up with that big client with the $75k pitch
  • Try to land a few new clients?

1,509 days until I turn $30. I’m making $10K a day passively by then

Dean Woods

Dean Woods

Dean’s goal is to create $10,000/day in passive income through entrepreneurship. Too many people write “success porn” that skates over the struggles many face in entrepreneurship. His goal is to create something real that highlights the lack of sleep, disappointment from family, and setbacks you really face in entrepreneurship. The hope is that $10K a day swill inspire someone else out there to make their entrepreneurship dreams happen. Dean Woods is side hustling and working a full time job to kickstart his entrepreneurial path. Prior to this life, Dean was a management consultant. Dean graduated with honors from The Wharton School.

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