The $0-$10K/Day Case Study: Update 200

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Update 200


The big 200.

It’s the 200th update thus far to the case study. That’s certainly fun and a nice number.

I could easily sit here and talk about progress made over the past 200 updates. We made a ton of money this year and made a ton of progress towards our overall goals. There is certainly a lot that could be celebrated.

But, 200 isn’t anything. 200 is basic. It’s not worth my time, or yours, to write a ‘celebrate we made it to 200 posts’ type of post.

2,000 updates? Then maybe

This is an overarching theme I think. The sad reality of the world is everyone falls for the marshmallow test. Everyone wants everything, immediately. You need to work hard and for a long consistent time to get the results you actually want.

200 posts is eating the first marshmallow immediately instead of waiting for two.

The question that’s worth asking is; do I actually have to wait?


My wife was showing me an Instagrammer she follows that does different outfits and fashion stuff. The Instagrammer isn’t a famous last name, doesn’t have the looks of a model, and (to my untrained eye) didn’t look any better than the next person at picking out outfits.

Yet, she has a million followers and my wife is showing me her account on a Sunday afternoon.

My bet is the only reason she has a million followers is because she has >4,000 photos posted. That’s it. Nothing else.

That’s why we shouldn’t celebrate 200 posts together.

  • Don’t celebrate 200 posts, write 2,000
  • Don’t celebrate 400 photos on Instagram, celebrate 4,000
  • Don’t do 100 pushups, do 1,000
  • Don’t work 10 hours, work 10,000

I’m convinced more people can be successful if they actually do the fucking work.

Yesterday there were 1,365 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 need to re-write this article since my phases are different.

Wake up & sleep

On the Oura, I got a 79 sleep score with total sleep time of 6 hours and 5 minutes, resting heart rate of 58 BPM. Asleep 10:19-6:43am. Overall feeling OK.


I can’t exercise really well due to my foot issues. I’ve had some bleeding in my toe so the podiatrist put a bunch of stuff on it and I need to take it easy as  result.

Stress levels

Stress was probably 5/5, with 1 being the highest.

Low stress day. Taking things easy while starting the business. I’m also beyond confident in it.


Yesterday was OK. Veggies for lunch and Chinese for dinner.

Investment real estate

Nothing here. We decided against the townhome we were thinking about buying yesterday. It’s too much cash ~($800K) for not enough rent (~$5K). I need the cash to be lower or the rent higher for it to work for us.

I want ~8% Cash on Cash return, at a minimum.

CCIO: My business

I am extremely confident in this business. Things are looking good.


Limited interviews since it was the weekend. I’m picking them back up on Monday.

Goal is to get to 100 customers by my birthday on 10/28.

Content website business

Letting the sites sit.

Acquisition Entrepreneurship

Nothing. Years down the road.

Side Consulting

Two projects at the moment.

Market Analysis

Nothing yesterday

Project support

Nothing Yesterday

Sourcing new work


$10K/day website

Daily post.


Time with my wiife!



Rescue Time Daily Screenshot

Apparently rescue time isn’t working on my other computer. Time to fix that

What I made yesterday

Current Income  Streams

  • Consulting work: $731.80

Total:  $731.80

Planned income streams

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

Yesterday’s pro-rated amount of monthly & yearly expenses


Life Expenses: $80.73

  • Rent, utilities, Internet: $63.33
  • Phone Bill (iPhone): $1.57
  • Ladder Life Insurance: $0.83
  • Car (2018 Audi Q5): $15

CCIO’s Expenses: $2.53

  • G Suite accounts (2x; one for cold outreach, one for everything else): $0.40
  • Lemlist for cold outreach: $1.97
  • Bluehost domain name: $0.16

Health Expenses: $3.20

  • Peloton: $3.20

Productivity Expenses: $2.05

  • SuperHuman (to save time on email): $1.00
  • Rescue Time (to keep me honest on my productivity): $0.20
  • Evernote (to track everything): $0.27
  • Grammarly (to keep my emails looking okay0: $0.38
  • BackBlaze (to keep my files backed up): $0.20

Consulting Business Expenses: $6.10

  • Quickbooks (to track expenses): $0.40
  • G Suite email (for email): $0.20
  • Hiscox business insurance (for liability): $4
  • Gusto (to pay myself): $1.50

Content Business: $6.13

  • 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: $1.97

$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)

I made $731.80 and spent $102.85 with a bottom line of:

$628.95 daily earnings (pre-tax)

My plan for tomorrow

Tomorrow is Monday and I have to go back to the doctor. Going to be a lighter day with limited business work.

1,364 days until I turn $30. I’m making $10K a day 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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