The $0-$10K/Day Case Study: Day 189

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Day 189


Things are smoking now. Lots of really good shit going on right now. Let’s see how we can keep that good shit moving.

So, first, right off the bat, I talked last post about how I ended up selling two of my five largest projects of all time in the same day. Yesterday was a really good day.

Yesterday was, arguably, even better. Yesterday was about signing those contracts and getting things all done and dusted. The contracts are now all signed and good to go so we are in a great spot now. Unless something catastrophic happens, we’re now in the necessary position to buy the properties we want to buy and to have enough cash leftover that it won’t kill us to do so.

With that in mind, there were a couple of big decisions that my fiancee and I needed to make in order to ensure that we are well set up for the future. Interestingly, all of them were about jobs. Namely:

  • What to do about my current day job?
  • What to do about the job I’m currently interviewing for?
  • What should I do if I’m not working a full-time job?

The context to keep in mind here is that we just had a baby who is just a few months old. There is also a pandemic going on and I firmly believe we arne’t through the worst of it yet. It’s objectively a horrible time to not have the security of a full-time job.

That being said, we decided to say “fuck it.” Here’s the plan, and then we’ll discuss why we made the decisions we did.

  • I will quit my current job at some point in the next 2 weeks
  • I will withdrawal from the interview process (even though it’s 99% I get the job)
  • I will devote 100% of my time towards building my business, CCIO

We made this decision because, well, why the hell not?

I’ve busted my ass over the past year to make nearly $200K in consulting. I have nearly $100K in consulting coming my way in the next two months. We’ll own $2.5m in cashflowing real estate by the end of the year.

Said differently: I hustled to make money and now we’re putting it into cashflowing assets to make more money. I didn’t blow it buying a fancy car.

Those assets (real estate) will give enough of a financial safety net that it will be possible for me to focus on growing a business. As we’ve talked about before, the business is how you make $10M+ in net worth.

I am pumped up. Let’s do this shit.

Yesterday there were 1,502 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 7 hours and 35 minutes from 9:27 pm to 6:57am, with two baby feeding breaks at night, for a total recovery score of 91% on the Whoop. Yesterday felt really good, so the recovery score checks out.

The other thing to note here was the day before was my first day in a  while eating fully healthy, which led to a great recovery score. I don’t think it’s a coincidence.

Eating healthy can objectively suck. That being said, if it makes me 10% better ever day, it’s a sacrifice worth making if it gets me to $10K a day at 30.


I did an Alex Touissant ride on the Peloton (he’s a total badass) and did fairly well. The ride was a 9.8 difficulty and my total day strain on the Whoop was 16.4

Stress levels

Stress was probably 4/5: I’m feeling good with everything and that we have a really solid plan moving forward for next year.


Diet was solid again. Oatmeal for breakfast, spinach salad lunch, and then Tofu Curry for dinner.

My Day Job

Quitting soon!

Investment real estate

Nothing. Keep the cashflow coming.

CCIO: My business

TBD on this for now. It’s coming in Q1 of 2021. Here’s my business plan

It’s also the focus of 2021.

Content website business

I did some more research today on Ahrefs for keywords and then created the Surfer SEO instances here for the content explorer. I’m pretty excited about it.

Acquisition Entrepreneurship

Nothing crazy. Just evaluating deals here and there. I won’t buy anything for a few years.

Side Consulting

Mostly signing contracts.

Data Project

I did some Excel work, but nothing crazy.

Presentation Project

This was really light, with the project to be done tomorrow.

Market Research

Nothing, waiting for kickoff call.

Market Analysis

Signing the contract, waiting for kickoff call.

Project Support

Signing the contract, waiting for kickoff call.

Sourcing new work

Firmly nothing for a while.

$10K/day website

Daily post


Family time 


I had an interview (went really well) for that other job but I need to take myself out of the process now.

Rescue Time Daily Screenshot

Day 189 Rescue Time
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
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $855

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 $855 spent $114, which means….

Made $741 (pre-tax)

My plan for tomorrow

Tomorrow is Thursday and I have:

  • Some data project work
  • A market research kick off call
  • Some bullshit work for my day job
  • Write a job posting for my content sites
  • Write for my content sites

1,501 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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