The $0-$10K/Day Case Study: Day 193

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Well, lots of emotion going on here.

Right off the bat, I’m extremely excited. I’m excited as hell actually.

The reason why is because I’ve finally quit my job. I am now officially unemployed and ready to never have a boss again. I’m officially an entrepreneur.

I’m absolutely slammed right now as I work across multiple clients and try to keep my head above water to make sure things stay strong and don’t go sideways. I think they very easily could, so it’s important to make sure that things keep going in the right direction for at least the next few months.

I need to make it to thanksgiving to get through this shitstorm of a client world. I have just too many projects going on right now to keep things going in the right direction and to keep my head above water. By making it through to Thanksgiving, I can then lower my consulting output by a ton, still make good money, and allow myself to focus on building my business CCIO.

I quit my day job so I can build CCIO. I should really focus on that!

The other thing that is going on and top of mind right now is our 49 unit deal. Regular readers of the case study have heard me talk about that to no end. I know I’m beating it to death and talking about it too much.

Well, the sad news is that it looks like this deal just might now happen.

We have the cash and they have the interest to sell. There are two problems:

  • We’ve been told for a while that there is a mold issue. However, they have yet to figure out exactly what the problem is for months now, which is even worse than the fact there is a mold issue.
  • The pro-forma numbers they shared look great, while the actual numbers we just got are shit. Like, losing several thousand dollars a month shit

We are planning to go visit the property in a week for the inspection. I’m excited to do that, but I’m also thinking this deal isn’t going to happen. That’s disappointing, because we assumed a lot of money made from this building next year. It also sets back  our unit count. Getting to 500 units at 30 is the goal, but if these ~50 aren’t possible, that hurts.

My fiancee and I have been rather bummed about this for the past day or two. We’ll get up and dust ourselves off and go find another building, but it stinks.

Yesterday there were 1,494 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 need to adjust the phases because the phases are different now!

Wake up & sleep:

Whoop had me at 6 hours and 36 minutes of sleep, going to get bed 10:41 and waking up at 6:47 with some baby feeding time in between there.

Tota recovery was 53% and not amazing given the circumstances (e.g: no job!) but also understandable given the circumstances (a shit ton of consulting work).


I did a hard 45min workout on the Peloton for a total strain of 12.0 on Whoop and a day strain of 15.9. Overall, not too shabby. Pretty happy with those numbers.

Stress levels

Stress was probably 3/5, with 1 being the highest. Busy day, and disappointing about the real estate deal


Diet was crap. Oatmeal for breakfast, noodles for lunch, curry for dinner.

All tasty, all vegan. Will take it

Investment real estate

You saw about the real estate above. It’s a bummer.

CCIO: My business

I have talked with a few people (agencies and pros) that I might want to hire to end up working for me in this business and the business needs.

Nothing on this until November, but I am excited about it.

Content website business

Well, we probably won’t need the money to buy real estate anymore. With that in mind, I’m thinking I’ll invest a few grand per month into building up websites that make a bunch of money.

I’ll probably write a post or two about those businesses and what I’m doing with them and how I’m thinking about them, but the short and sweet of it is:

  • Start a website on a broad topic (e.g: Bike Riding)
  • Hire people to write a shit ton of content for me
  • Make money off the display ads
  • Start more websites

The number I have in my head is 50 websites getting 1M visitors a month. That should make me around ~$500K a month, or well more than $10K a day.

It will also take ~75,000 articles of average length 1,500 words, or more than 100M words.

So, you know, a shit ton of writing. That’s a lot of people to hire and a lot of content to write.

Acquisition Entrepreneurship

I’ve been talking with one guy about a business. It’s not crazy interesting because the company that supplies the company for sale could pretty easily put them out of business.

Side Consulting

I’m slammed.

Data Project

Nothing yesterday.

Market Research

Nothing yesterday.

Market Analysis

I spent most of the day on this building out some content because of a call with the client the next day.

Project Support

This was also busy. Between this and the other project, I’ll spend the majority of my time on these two projects.

Sourcing new work

I have a pitch call next week on another ~$30K project, but that should be about it.

$10K/day website

Daily post


Family time with my fiancee at night.



Rescue Time Daily Screenshot

Day 193 Rescue Time
Fairly standard start at 6am end at 9am kind of day.

What I made today

Current Income  Streams


  • Market Research: $220
  • Market Analysis: $634
  • Project Support: $487
  • Real Estate Cashflow (13 multi-family units): $65
  • Content sites: $0

Total:  $1,406

Planned income streams

  • My Business (CCIO)
  • Ads on $10K
  • Acquired businesses
  • Coaching
  • Acquired hotels
  • Dividend stocks (especially muni bonds)

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


Life Expenses: $100

  • Rent, utilities, Internet: $63.33
  • Phone Bill: $1.57
  • Health Insurance (COBRA): $19
  • 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

Content Business: $47.45

  • Bluehost for hosting (9 domains): $0.89
  • Bluehost for domain names(9 domains): $0.27
  • Ahrefs for keyword research: $3.00
  • Surfer SEO for content: $6.63
  • Full time employees (two writers): $36.66

$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 $1,406 pent $160, which means….

Made $1,246 (pre-tax)

My plan for tomorrow

Tomorrow is Friday and I have:

  • 3 calls, including a big one for the market research
  • Project support work
  • Market research work
  • Content business work

1,493 days until I turn $30. I’m making $10K a day passively by then

Dean Woods

Dean Woods

Dean has started multiple businesses, with two successes to date. Outside of starting businesses, Dean & his wife buy multifamily real estate and will soon start buying businesses. This case study is meant to cover the daily struggles it actually takes to be an entrepreneur & serve as a giant middle finger to the 'gurus' in rented Lamborghinis. Dean is an Alum of Boston Consulting Group and The Wharton School. He and his wife live in Chicago with their children

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