The $0-$10K/Day Case Study: Day 137

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Day 137


It’s an interesting time in the world right now.

Yesterday was Saturday, May 30th and downtown Chicago was absolutely destroyed. I saw videos of places I’ve walk by a thousand times get destroyed. There was a video of someone on the street near my old apartment shooting at someone in that apartment on a balcony.

There’s certainly a lot to say on the topic and I’m also not the right person to say most of it.

Instead, I’ll comment on things that I can speak more eloquently about: wealth, money, and the 1%.

There was a clear trend in what the protestors destroyed yesterday

Tracking the looting in Chicago yesterday, it’s clear that protesters went after locations and stores that symbolize wealth.

Any Chicagoan can tell you that Michigan Ave is not where the majority of wealth is concentrated in Chicago. The majority of wealth (downtown) is concentrated in the Gold Coast area. That’s where you will find the $58M penthouse, the Chanel and Hermes store, the Rolls Royce/Lamborghini dealership, and the Viagra triangle, so named because lots of old guys with money go to pick up 22-year-old girls looking for old guys with money.

It’s a nice area, but it’s not big. The streets are narrow. Michigan Ave is a large area and definitely more conducive to a protest. If I were protesting, Michigan Ave is where I would stay.

Yet, the protestors went to the extremely small but wealth area in the Gold Coast.

While there, sayings like: “Eat the Rich” and “Fuck Capitalism” were spray-painted onto the buildings.

I’m in the 0.1%. Here’s how I feel about the protests yesterday, and in general, targetting the 1%

My fiancee and I in the top 1% overall in the country, which required an income of $421K in 2018.

Financial Samurai states that the top 0.1% in the 27-31 age bracket is $300K a year. We definitely exceed that number as well. My math forecasts us at well over 25% higher than that for 2020.

So, here are three over-arching thoughts on how I feel about everything:

#1: I don’t think I’ve hurt anyone on my journey to get here

A lot of criticism I see about the 1% is that they “hurt the little guy” to get where they are. I genuinely don’t think I’ve done that, but please tell me if you feel differently.

I don’t have employees, so I don’t hurt people there.

I do hire freelancers. I have a guy in Bangladesh that I pay the equivalent of >$100/hour too. He lives in a nice part of town and is getting married soon.

You could say that I am hurting American jobs. However, when I post these jobs online (without a budget, I should add), Americans never apply. However, I get 50+ applications in 5 minutes from lower cost of living countries.

I also have gotten jobs, which means other people didn’t get the jobs that I applied for. However, that’s because I busted my ass to accepted to the top Business School in the world. I don’t think I can be accused of hurting anyone there: I applied and got accepted.

There are certainly some rich people who have taken advantage of others. I don’t think I have. It makes me hate the criticism that “all rich people hurt people.”

#2: I do not “buy” political elections and politicians

I have no clue where I would even start to do this. Like anyone, I have politicians I like and don’t like.

I’ve never donated politically. I don’t know how to “buy” someone to support my cause.

#3: I do not break the law or believe I am above the law

Could I break the law? I mean, maybe?

I sign a ton of NDA’s for consulting clients. I probably know information that would be considered insider information.

Guess what: I don’t trade stocks on that. I buy real estate.

The law applies to me, and everyone else.

Which leads to the biggest point of all: I don’t think I’ve done anything wrong

People have always protested against the wealthy and will continue to do so moving forward. I don’t believe I’ve done anything even remotely sketchy or wrong in my life.

That’s why I absolutely hate blanket statements like “eat the rich” and “fuck capitalism.”

I agree some rich people are dicks.

I also believe non rich people are dicks too.

I don’t think I fit into that category.

Yet, I’m still scared for my family. I don’t think an angry mob that is mad at a label I currently hold will care if I believe I’ve done anything wrong or not. I don’t think everyone who got beheaded in the French Revolution did something wrong.

I’m scared there will be more protests and violence against wealth. I’m scared my family will be targetted.

Yesterday there were 1,611 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 #1:  The Job & Side Hustle Phase.  You can read more about the phases and my plan to get to $10K/a day at 30 here.

Wake up & sleep:

I woke up at 8:12 am after going to bed at 12:06, for a total amount of sleep of 7 hours and 36 minutes.It was a good amount of sleep, but lower than ideal recovery at 49%. I think I need to get more sleep ASAP and stretch to get recovery up because this is going to be a busy week.


No exercise for me today.

Stress levels

I was at a 2/5, with 1 being the highest. As I mentioned above, I’m worried for my family security with everything going on.


Diet was coffee, and cereal.

3/5 with 1 being the best.

My Day Job

It was a Saturday.

Investment real estate

Nothing here

My Actual Business

I did a bunch more reading online on Reddit. I’m looking to read posts from my target user to understand what they complain about.

When your target user complains, it means a product or service that fixes that complaint is of value to them.

Side Consulting

Still busy with lots of projects.

Business plan

Nothing here.

Financial modeling

I made some tweaks to the model. There’s a lot of work here, so I hired my model guy to take it for me because I am so busy.


Nothing here.

Summary presentations

Nothing here

Market Research & Customer  Interviews

Lots of work here getting things set up and ready to go.

Sourcing new work


$10K/day website

The daily post.


Fiancee time.


Nothing misc today

Rescue Time Daily Screenshot

Solid 6 hours, which I think is a solid Saturday.

What I made today

Current Income  Streams

  • Job:  $170
  • Rental Income (13 rental units): $43
  • Business Plan: $145
  • Framework: $250
  • Customer Interviews: $430

Total:  $1,038

Planned income streams

  • My Actual Busines
  • Local Serviced Based Business
  • Affiliate
  • WordPress Maintenance Site
  • Dividend Income
  • Micro-SAAS’s
  • Hotels

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
  • Groceries: $0

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: $33.30

  • Gusto to pay myself: $1.50
  • Quickbooks to track expenses: $0.40
  • Google Business Email Account: $0.40
  • Fiverr for virtual support: $0
  • UpWork for slides:  $0
  • UpWork for my financial modeler

$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 $1,038, spent $156, which means….

Made $882 (pre-tax)

My plan for tomorrow

Tomorrow I need to:

  • Sleep
  • Get Ready for a BUSY Monday with one of my main clients (the market scan one)

Let’s get after it!

1,611 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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