The $0-$10K/Day Case Study: Day 171

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day 171


Jeez, it’s been a few days. I’m working my way through my big ass list of shit to do. I apologize for falling behind here; not my intention. It’s Tuesday. I think my last post here was Thursday. My bad team.

I’m feeling feisty right now even though I’ve fallen behind. I’m going to keep the bold thoughts coming.

The other day, I wrote about how saying wealthy people got “lucky” is naive as fuck.

Today, I’m going to write something somewhat similarly bold.

Here it is: you will never reach true wealth if you are a shitty manager of people.

At my day job, my CEO is a shitty manager. He is dismissive of effort, dismissive of people’s (very legitimate) issues with his strategy, and not pleasant to be around.

But worst of all, his arrogance and condescension to the team is palpable. He uses phrases like “You do understand why you are wrong” all the time. He also talks about “market perspective” and how he is the only one who truly understands this industry.

Bro, you have a negative burn business that’s several years too old to not be in the eight figures of revenue range. BTW: most of your team is more credentialed than you are.

For that reason, the talent is actively leaving or talking about leaving when he isn’t in the room. My guess is most of the “legit” talent will be gone in less than 6-12 months.

This is a really important point, so it’s important to underscore: this company could be very successful.

The CEO being an asshole to his talent, and not including them in his strategy setting, is the single reason why the company won’t succeed. The strategy changes every single day. I have no clue what our company “goal” is.

Here’s the reality: managing people is how you make money.

Your job as a CEO is to assemble a fantastic team, set a north star metric for the team to shoot for, and then spend all of your time removing obstacles in their way.

You are not supposed to be telling them what to do. Your job is to make it easier for them to do their job. For example, if someone can’t get what they need to be done because they need specific software, your role is to get them that software ASAP and then get out of their way.

Wealthy people know this. You’d be surprised exactly how good of a boss people who are worth >$100M are.

Yesterday there were 1,533 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:

Sleep was actually really decent yesterday. I got 7 hours and 45 minutes and was 80% recovered.

Not bad at all for the baby being home!


No workout, which was less good! I’ll do that as soon as I can.

Stress levels

Tuesday was a 3/5 stress day, with 1 being the highest. Not too bad heere.


Diet was coffee, leftover curry and then spinach for dinner. All vegan.

The recovery was only decent because of the good diet.

My Day Job

Nothing. I really can’t wait to just pull the plug here.

Investment real estate

Nothing here

CCIO: My business

Couple conversations with my fiancee here about this. She has really good insight so working together on this project is really fun.

Side Consulting

I’m slammed.

Data/strategy work

I did some slides and some Excel modeling here. Nothing horrible, nothing super light either.

New huge project

Not much here

Sourcing new work

Nothing here. Optimally things stay this way for a while.

$10K/day website



Time with the baby and fiancee!



Rescue Time Daily Screenshot

This is underreporting time I spent working on my other computer. The reality is Mac can’t handle the work I need it to do, so I have to use a Lenovo sometimes for excel

What I made today

Current Income  Streams

  • Job:  $170
  • Consulting Project: $650

Total:  $820

Planned income streams

  • My Business (CCIO)
  • WordPress Maintenance Site
  • Content sites
  • Micro-SAAS’s
  • Acquired businesses

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


Life Expenses: $89.73

  • Rent, utilities, Internet: $63.33
  • Phone Bill: $1.57
  • Heath 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: $12.00

  • Peloton: $3.20
  • Gainful Protein Powder: $1.80
  • Care/of Vitamin pack: $3.00
  • 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: $6

  • Gusto to pay myself: $1.50
  • Quickbooks to track expenses: $0.40
  • Google Business Email Account: $0.40
  • Fiverr for virtual support: $0
  • Hiscox business insurance: $4

$10K a day: $12.42

  • 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
  • Rhino Rank for SEO: $10.83

Real Estate Investing: $0.52

  • Legal Zoom Registered Agent (all LLC’s): $0.52

Today’s Income (pre-tax)

Topline of $1,165, spent $2,123, which means….

Made $597 (pre-tax)

My plan for tomorrow

Tomorrow is Wednesday, and I need to do:

  • Finish up some work my international client
  • do some day job work
  • call my grandparents

1,532 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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