The $0-$10K/Day Case Study: Day 181

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It’s been a few days since I’ve posted here. I figured it’s time for a new post.

Last week, I re-wrote the about page of $10K. In that page, I promised to give you the unvarnished truth as the reader about what my life is like and what is on my mind as I attempt this $0-$10K a day journey.

Well, here’s the reality of it.

Yesterday, while sitting on the couch, I just broke down in tears and started crying. I couldn’t contain myself or control myself. The stress, pressure, and hard work, coupled with raising a newborn, just got to me.

You could fairly say that this is the world’s smallest violin and I shouldn’t be busy and sad or stressed. But, the reality is, I am. This life isn’t easy. I chose it, but it isn’t easy.

It would be easy to not work hard and push myself for more. It would be easy to not set an early morning alarm, it would be easy to skip the Peloton workout, easy to not make one more sales call, easy to sit on my couch and criticize others.

But, that exact mentality is why most people are wealthy.

You need to push yourself to be wealthy. You need to push yourself to live an extraordinary life. I’m going to do just that.


Yesterday there were 1,512 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’ve been sleeping 6-8 hours pretty consistently the past few days. Whoop has my recovery in the 50-60% range though.


I’ve done only two Peloton workouts in the past week or so. Optimally, this number should be a lot higher.

Stress levels

I’m randomly crying in my living room. I’ll let you answer that one


I’ve actually not been super vegan here, which isn’t great. I can and should be a lot more vegan here. I think the decrease in vegan eating is why my recovery is lower even though I have had fairly decent sleep.

My Day Job

This is just a waste of time. I’m looking forward to jettisoning this.

Investment real estate

Nothing here, as it should be.

CCIO: My business

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

Side Consulting

Same old same old.

Data Project

This has been more time-intensive as of the last few days and should continue to be so over the next few as well.

The main thing I have to do is figure out how someone else screwed up an Excel model. It’s actually more complicated than you would expect, so we’ll see what happens.

Sourcing new work

I had a good pitch call for some work. It’s helpful because this project was for a former McKinsey dude so we spoke the same language. I used a fair amount of “MBB language”, such as “stickies” to make him feel comfortable. At the end of the call, he said he had a few more calls but was going to go with me.

Build comfort in sales prospects if you want to really sell!

$10K/day website

I rewrote the about page.


Time with the baby and fiancee.


Nothing much here

Rescue Time Daily Screenshot

I’ve averaged about ~7 or 8 hours of work this past week. Not a ton.

What I made today

Current Income  Streams

  • Job:  $170
  • Consulting for data project: $1,000
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $1,235

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

$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 $1,235 spent $103, which means….

Made $1,132 (pre-tax)

My plan for tomorrow

Tomorrow is Tuesday, and I have to:

  • 6 hours or more of meetings with my day job and a variety of clients
  • Debug that damn excel model!

1,511 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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