The $0-$10K/Day Case Study: Day 180

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Day 180


There are a lot of things going on these days. It makes stress happen perhaps more frequently than I should.

Yesterday, for example, I bounced between a dozen different pieces of work. Some clients had questions, some didn’t, and I was pitching on new work left and right.

Some of it was high value add, some of it wasn’t.

Either way, I need to simplify. I need to remove a lot of this bullshit from my day-to-day so I can focus on growing a business. That’s always been the goal, so shouldn’t I try to knock down any and all barriers that get in the way of that goal?

Last night, our little baby started crying at 2 in the morning so I was walking with him up and down the hallways to try and calm him down and help him go back to sleep. It got me thinking about this website, $10K.

I firmly intend to make money from this website, largely through advertising. If your site gets >10,000 visitors a month, you can sign up for something called Ezoic that puts ads on your site. If you get >65,000 a month, then you can sign up for something called Mediavine that lets you put higher-earning ads onto your site.

In my model for 2021, I assume right now roughly ~$7,500 a month in consulting income from Q1-Q3. That’s about half of what I am doing now.

What if instead of consulting income I replace that with advertising income?

Well, it should simplify down my day. Rather than unpredictability born from unique clients that have different objectives every few months, I can instead perform the same action consistently each day (namely, write!).

That predictability would save me a shit ton of time and stress, which would be great.

What’s the catch?

It sounds great in theory: have advertising replace my consulting income to the tune of $7,500 per month and then focus my time entirely on growing other businesses.

It’s a safe assumption to say that I can earn $12.50 in advertising per 1,000 visitors to $10K. To get to $7,500 per month, that means I need ($7,500/12.50) x 1,000 = 600,000 visitors per month onto this website.

That is an absolute shit ton of visitors.

No worries though, how do I get that many?

I write a shit ton.

If you post something three times a day, Google decides it really starts loving your website a lot more than it does if you post one time a day.

I’m going to start writing a lot more and sharing my thoughts on a broader range of business-related topics. I get paid thousands of dollars for my thoughts, maybe I should make them free on a blog and see what happens!

Yesterday there were 1,517 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:

Overall pretty solid day here. 8 hours and 31 minutes of sleep, going to bed at 10:19 and waking up at 8:52 with a total recovery score of 88% on Whoop. That’s a lot better than I would have expected, and I think helped my morning feel pretty productive.


I did a 20 minute Peloton ride, which led to a total day strain of 17.6 on Whoop. This strain is way higher than I would have expected, which I think is driven by the stress I felt during the day bouncing between clients.

Stress levels

Call it 2/5 on the stress, with 1 being the highest.

It’s driven for sure by the number of clients and things competing for my attention. On one hand, that’s great. On the other, I feel bouncy, not settled, and slammed.


Oatmeal, coffee, vegan pad thai, vegan quesadillas.

I have enough shit going on that if eating vegan gives me even the slightest boost, I need to do it.

My Day Job

I did not do a single here at all. Not a one.

Not too bad at all if you ask me!

Investment real estate

Pretty good day here if you ask me.

We heard from the insurance adjuster on our 7 unit deal after a storm blew through the area a couple of weeks back. Long story short, we’re going to get a fair amount of support from insurance. For example, we’re getting a bunch of siding, a new window, storm door, and most importantly, a new roof.

That roof part is extremely exciting. Our roof was approaching ~15 years old and would have needed a full replacement relatively soon. We would have needed to pay $10-$20K out of pocket for that roof.

However, the storm ended up destroying the roof prematurely. As a result, insurance will now buy us a brand new roof for the low price of our ~$5K deductible.

That’s a huge cost saving for us. If we decide to sell, it will be a lot easier to do so now with a new roof. If we decide to keep the property, it will save us a bunch of money whenever the original roof would have failed.

CCIO: My business

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

Side Consulting

I am not doing a ton of work right now here, which is a bit worrisome. I wish I had more work here.

Data Project

I had a quick call and some emails, but nothing crazy here. A pretty light day.

Sourcing new work

I applied for a lot more jobs today and followed up with some past clients to try and secure a new project.

I would very much like some more work.

$10K/day website

I talked about this above. I have a bunch of “stuff” to do here.


Time with the baby and fiancee.


I did a quick write up for that new potential job of mine!

Rescue Time Daily Screenshot

Day 180 Rescue Time
These are rookie numbers. Time to pump this up

What I made today

Current Income  Streams

  • Job:  $170
  • Consulting for data project: $75
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $310

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 $310 spent $103, which means….

Made $207 (pre-tax)

My plan for tomorrow

Tomorrow is Wednesday, and I have to:

  • Couple of posts on $10K
  • Pitch on new work
  • More work on that sample project for my potential new boss
  • A quick deck for my data client

1,516 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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