The $0-$10K/Day Case Study: Day 187

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Day 187


This will be short because I can barely keep my head above water right now.

I have too much fucking work.

Which, is a good thing. We’ll get to buy the real estate we want.

I just might combust in the process

Yesterday there were 1,504 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 12 minutes from 12:51 am to 8:27am, with baby feeding breaks at night, for a total recovery score of 76%. I clearly slept like shit, and late, so I’m not sure why this recovery was decent.


I didn’t exercise.

Stress levels

Stress was probably 3/5.


Diet was fine, nothing bad nothing great. I think a standard assortment of random stuff.

My Day Job

I literally didn’t do anything because I was trying to keep my head above water.

Investment real estate

Nothing. Keep the cashflow coming.

CCIO: My business

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

Content website business

I spent an hour or two here getting started with keyword research for Ahrefs and then creating a bunch of content outlines with Surfer SEO. With both of those in mind, I was able to get my brother up and running to start writing.

I plan to start writing as well as soon as I have an opportunity to do so.

Acquisition Entrepreneurship

I analyzed my first Axial deal. It was a $10M company in the trucking space with ~15% margins and recurring B2B revenue. I love B2B, and I love recurring revenue.

I hate trucking, simply because self-driving trucks will change the industry. I’m not willing to bet $10m that I can correctly guess that.

Side Consulting

It’s a world.

Data Project

We had a couple of calls here. The client is interested in introducing some new Excel models into our day-to-day, so my job is going to build out a model(s) that allow us to do some nifty analytics. Overall, I think it’s going in the right direction here but I’m behind on what I should be done with at this point.

Presentation Project

Lots of meetings and lots of powerpoint adjustments here

Market Research

Nothing, waiting for a kickoff call.

Sourcing new work

Still have proposals out. One of my proposals asked to hop on the phone tomorrow morning, which is usually a good sign or a request to ask for more info.

$10K/day website

Daily post


As much time as possible with my fiancee.



Rescue Time Daily Screenshot

It felt way longer than this. I think that’s because I don’t have any breaks and I’m cranking 100% of the time. I might try to introduce a break tomorrow.

What I made today

Current Income  Streams

  • Job:  $170
  • Presentation project: $400
  • Data Project: $1,000
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $1,635

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

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 $1,635 spent $114, which means….

Made $1,521 (pre-tax)

My plan for tomorrow

Tomorrow is Tuesday and I have:

  • A follow-up call on a proposal
  • Get close to finishing up the presentation project
  • Some day job work that I’ve put off thus far
  • Data project modeling

1,503 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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