The $0-$10K/Day Case Study: Day 191

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Day 191


Man, what a day!

I woke up, planning to have it be a regular Friday. Of course, it wasn’t a regular Friday since it was a 500 day…1,500 days until I turn 30.

Maybe that’s why I was feeling a certain sort of way. I’m not sure.

Either way, I was halfway through my third meeting of the day for my day job, looked over to my fiancee, and started complaining about it.

She looked back and said: “Well, why don’t you just quit? You can quit any time.”

She was right, of course, and it felt great to be able to say it out loud.

So, we decided on the spot to have me quit. I called the people I needed to call, both bosses and friends, and I just hung out the rest of the day.

It felt fucking fantastic.

Quitting now just makes too much sense. For one, consulting is just making me too much money. 

I couldn’t wait. And I can’t wait to get started on everything I’m going to do!

Yesterday there were 1,500 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 50 minutes from 9:34 pm to 6:06am, with two baby feeding breaks at night, for a total recovery score of 47% on the Whoop. Not great, not horrible..


I did a quick Pelotonn workout (20min) with a 7.1 strain score on Whoop and a total day strain of 18.2

Stress levels

Stress was probably 5/5, with 1 being the highest. I was feeling really good because I quit!


Diet was crap. Oatmeal for breakfast, sugary bubble tea for lunch, and then leftover pasta for dinner.

My Day Job

Well, this line item will be gone shortly on my day to day!

Investment real estate


CCIO: My business

This is now going to be my focus and I am really excited.

Content website business

I put out a job description for this for UpWork and Honestly, I’d prefer to hire people on Online Jobs just because that feels a little more “legit.” After all, I am looking for full-time employees. However, I would like to get some people started in the next week so I may just have to default to UpWork to help get that going.

We’ll see what happens, but I need content creation up and running sooner rather than later!

Acquisition Entrepreneurship

Saw a great deal come through that makes steel inserts that go into commercial buildings. It does $7.75M a year in revenue and $2.25M in profit, so roughly 30% margins in a B2B space. The company is also 30 years old and has a really strong market perception.

I’m not in the market to buy for another ~4-5 years, but this is exactly the kind of business I want to buy. It’ll probably sell for ~5X profit, so maybe $10-11M sales price…10% down will be roughly $1.5M (including closing costs).

Ahhh, I love it.

Side Consulting

Busy busy busy.

Data Project

A few quick things here or there, but nothing crazy.

Presentation Project

A payment request has been submitted.

Market Research

I sent my first end of day update email here and am now off to the races on this one. This should be super easy as long as the client is super easy to work with. I’ll spend an hour or two on this per day and be done ASAP.

Market Analysis

We had a quick kickoff call. Going to be busy here.

Project Support

Waiting for kickoff call, although I did receive an email from them regarding updates.

Sourcing new work

So yesterday I said I wasn’t going to source more work for a while. However, I had another ~$50K project reach out so now I’m entertaining the idea of taking that one too.

$10K/day website

Daily post


Lots of family time this weekend!



Rescue Time Daily Screenshot

You can see that it was a lighter day today!

What I made today

Current Income  Streams

  • Job:  $170
  • Presentation project: $400
  • Market Research: $220
  • Market Analysis: $634
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $1,489

Planned income streams

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

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

Content Business: $10.79

  • 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

$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 $1,489 spent $114, which means….

Made $1,375 (pre-tax)

My plan for tomorrow

Tomorrow is Monnday and I have:

  • 5 or 6 calls to kickoff different projects
  • Slide work
  • Excel work
  • Figuring out when my last day is with my company!

1,497 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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