The $0-$10K/Day Case Study: Day 192

Share on facebook
Share on google
Share on twitter
Share on linkedin
Day 192


You know what is exciting?

Quitting your job!

I am feeling really good these days and very excited about the world. I’m excited that I’m finally able to go after the things I want to go after and am able to fully lead the entrepreneurial path.

Yesterday, for example, was a busy day. In fact, it was one of the longest days I’ve worked in a long time (from 6am to 9pm) but it was exciting because it was the start of something entrepreneurial. Sure, I have some “handover” work to do for my full time job. However, that work is absolutely on the back nine and I’m just about done.

This is so fucking exciting.

I do consulting, like crazy, for the next ~60-90 days.

2020 is about consulting.

2021 is about getting CCIO from $0 to ~$250K

2022 is about scaling CCIO from ~$250K to $1M (which should be easier than scaling from $0-$250K!) and investing this money into assets like real estate.

Lets fucking get it!

Yesterday there were 1,497 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:

No Whoop on so no sleep data.


No Peloton workout today, just some stretching at night. I ended up with a 15.2 strain score on the Whoop.

Stress levels

Stress was probably 2/5, with 1 being the highest. It was a really busy day (6am-9pm) so I was tired as hell.


Diet was crap. Oatmeal for breakfast, bad quality Chinese food for lunch, and then Farro for dinner, which helped rescue it a little bit.

My Day Job

Some hand over stuff here as I wrap up my job, but we’re pretty much approaching the end of the line here.

Investment real estate


CCIO: My business

Nothing-consulting through the end of the year to make money.

Content website business

Not much

Acquisition Entrepreneurship

Not much….got more deals set my way via Axial but haven’t pulled the trigger just yet.

Side Consulting

I’m slammed.

Data Project

A call here, and then I have some work to do later this week.

Presentation Project

I got paid and a nice note from the client. Always good when that happens!

Market Research

I sent an email or two here. I need to do a lot more tomorrow

Market Analysis

I had a quick call with the client. It went just OK…..I need to impress them this week so things continue going well.

Project Support

I had a call here and this went really well. I think they are impressed. Some follow up work here as a result.

Sourcing new work

That $50K project I mentioned yesterday ended up having a really, really good pitch call. I think I’ll sell that project too

$10K/day website

Daily post


Family time with my fiancee at night.



Rescue Time Daily Screenshot

Day 192 Rescue Time
There’s the 6am to 9pm day.

What I made today

Current Income  Streams

  • Job:  $170
  • Market Research: $220
  • Market Analysis: $634
  • Data: $94
  • Project Support: $525
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $1,708

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 $1,708 pent $114, which means….

Made $1,594 (pre-tax)

My plan for tomorrow

Tomorrow is Tuesday and I have:

  • 3-4 calls
  • Slide work for project support
  • Outlining work for the market analysis project
  • Handover work for my existing company

1,496 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

Leave a Replay


Sign up to learn from Dean’s mistakes as he tries to create $10,000 dollars a day in passive income

About Me

Recent Posts

Follow Us

Sign up to prepare for your own case study

Spam is for amateurs, as is selling your data

Scroll to Top