The $0-$10K/Day Case Study: Day 190

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Today is a big day. It’s a “500 day.”

You see, as I write this, there are 1,500 days until I turn 30. 1,500 days until I need to be making $10K a day passively. 1,500 days until “retirement” from the grind.

I’m not a guy who really focuses on the past. I don’t dwell on past mistakes or missed opportunities. I think in and about the future. That’s all that matters. Fuck, I count down, daily, how many days left until I’m 30. You can’t get much more future oriented than that.

But, with it being a 500 day, I think it’s worth thinking about what has been accomplished over the past 500 days.

  • 500 days ago, I told my then girlfriend about how it was a 500 day and she thought I was nuts. Now, she’s my fiancee and the love of my life
  • 500 days ago, we had picked out a name for a fictious daugther. Now, we have a real son who, when he’s not waking us up in the morning, is the greatest thing
  • 500 days ago, I worked for a big consulting firm. I worked crap hours for crap people making crap money while living  out of a hotel. Now, I work for myself (mostly) and make way more. I’ve sold $300K+ in consulting work, which is crazy because I just wrote the article about how I sold $174K in consulting.
  • 500 days ago, I had the wrong notion about startups (e.g: you don’t make money in startups). Now, I know the true path to make $10M+.
  • 500 days ago, I owned exactly no real estate. Now, my fiancee and I own 13 units with another 49 on the way.

As you can see, A lot has changed over the past 500 days. If I was 1% of the way to making $10K a day at 30 500 days ago, I’m easily ~10% of the way there.

You can get a hell of a lot of stuff done in 500 days. And I have 3X that (1,500 days) to get to $10K  a day.

I know I can make it. And I’m excited to bring you with me on that journey.

Yesterday there were 1,501 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 5 hours and 20 minutes from 11:09 pm to 5:56am, with two baby feeding breaks at night, for a total recovery score of 20% on the Whoop. Dog shit sleep and recovery.


I did a workout with a 10.7 strain score on Whoop and a total day strain of 16.2

Stress levels

Stress was probably 3/5: I’m really tired with the crappy recovery which I think is what helped make me not feel great.


Diet was solid again. Oatmeal for breakfast, and then a protein shake for dinner.

My Day Job

It was there. My day job is a  great example of a thing that drives me nuts but shouldn’t.

Investment real estate


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

Lots of stuff here. I wrote three articles and added them up to the site and my brother did the same. We need to get up to 1,000 articles pretty quickly to ensure we make money off of this damn thing.

I also put some job posts out there to try and find a writer t help write for me!

Acquisition Entrepreneurship

A few deals came my way that I looked through quickly.

Side Consulting

Not much.

Data Project

Nothing here today, pretty laid back day actually.

Presentation Project

Project done; time to get paid.

Market Research

Kickoff call with the clients. They mostly just wanted to talk, which was fine. Very limited action required on my side of things.

Market Analysis

Waiting for kickoff call.

Project Support

Waiting for kickoff call.

Sourcing new work

Firmly nothing for a while.

$10K/day website

Daily post


Family time 



Rescue Time Daily Screenshot

Day 190 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
  • 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 Friday and I have:

  • A couple of big calls
  • I need to do some work
  • Sleep

1,500 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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