The $0-$10K/Day Case Study: Update 196

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Update 196


It’s been a long time since I last wrote here. A really long time.

Today is January 26th and my last post was October 11th. So, call it 3+ months.

There will be a ton of updates across all different dimensions below, but it’s safe to say that this ~100 day period was the most impactful period I’ve had in my professional and personal career.

I’ve been busy as shit. Before I dive into the actual update that you guys all deserve, let me talk about being busy and the concept of hard work for a second.

Stop saying you work hard…unless you actually do

One thing I feel pretty strongly about is that people mistakenly use the phrase “hard work.” It’s a phrase that gets thrown around a lot. Think about it: how many people say they don’t do “hard work?”

The problem is, “hard work” isn’t a fixed definition. Your definition of hard work could be very different than someone else’s. For example, someone who did “hard work” at a 9-5 is very different than someone who works in M&A at Goldman and works 9 am-4 am every single day.

The Goldman person clearly is working harder. However, if the 9-5 person doesn’t realize that there is another level of work (e.g: the “Goldman” level), the 9-5 person will struggle to reach their goals. Mr/Mrs. 9-5 is being outworked every day.

Personally, I’m sick of seeing people who work 9-5 complaining that they “work so hard” and should be entitled to the same level of financial rewards as someone who actually works hard. I think it’s frankly ridiculous.

That’s why I think we need to quantify what hard work is. Saying “85 hours a week” doesn’t really drive the point home because most people aren’t familiar with exactly the number of hours they work each week.

Instead, I say something along the lines of: “I woke up at 5am to get a head start on work and finished at 10pm.” That, my friends, is a 17 hour workday. Have 5 of those in a row and you are at 85 hours a week.

Tell me again, Mr/Mrs. 9-5, on how you work “so hard” when there are people out there working 5am-10pm?

This case study is raw. It’s emotional. It’s authentic. And it shows what it actually fucking takes to achieve your goals.

Sit down, stop complaining, and work.

The actual update: What has happened since we last spoke?

I’ll follow the standard update to the case study below, but it’s worth making a separate section here as a general update to discuss what has been happening!

Let’s start on the personal side of things first.

Personal Update

On the personal side of things, the most important update is that our little son continues to grow like a weed. He’s well under a year old, but is wearing clothes made for a three year old. My brother thinks we should start teaching him basketball.

As a positive development, his sleep is now noticeably better. It’s still not stellar, but it certainly is a lot better.

My wife is still the most important person in my life. She’s my partner in every sense of the word. She’s now back to work, and it’s far from easy with both of us balancing child care and work. We don’t have easy jobs, and it’s not a walk in the park to do all of this.

If it was, then everyone would be millionaires.

The more exciting thing going on is we have an offer accepted on a house for us to live in! It’s a new construction home in a great school district in the Chicago area.

I’ve personally been very hesitant to buy a home for us. As regular readers know, my wife and I strongly prefer to buy investment real estate instead of personal real estate.

However, this property we’re buying allows us to get outside (we can’t really go outside now due to COVID and being in a more populated area). It’s an element we can’t quantify, but certainly has value.

The other big benefit is we think this property can rent for ~$5,000 a month and shouldn’t ever have vacancy. Since our total out of pocket expense on the property is ~$3,000 (it’s this low because interest rates are low0, we expect we’ll move out at some point in a few years to have this be a rental.

Professional Update

The other side of things is that, professionally, things are booming.

Over the last four months, we’ve brought in $179,610 via consulting income. It’s been busy and a lot of hours, without a doubt. It’s also far from the goal of $10K/day.

But, I’m proud of the progress made. I wrote an article about how I did roughly that amount in my first year consulting, and now I’m able to do that in a third as much time. Annualized, it’s well over $500K and would build up a nest egg pretty quickly to buy businesses and real estate.

However, I’m about to quit consulting. Or, throttle it back ~90%.

It’s great, but it’s not scalable the way a business is. My projects are also entirely different, so I can’t systemitize the business. One project might be a lot of internal belief audits. Another is a market scan. Different projects means different systems and I can’t hire emmployees.

So, the biggest update on the professional side of things is that CCIO is now officially incorporated and funded (I transfered in $10K) and on it’s way!

Lets keep going with the update, shall we?

Yesterday there were 1,371 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

I used to track this with Whoop but I got really tired of it. Paying $30 a month was annoying, and then it took forever to update. I’ve switched over to Oura and it’s smaller, faster, and I think more accurate.

On the Oura, I got a 75 sleep score with total sleep time of 6 hours and 20 minutes, resting heart rate of 56 BPM. Asleep 12:10-7:22


Largely limited over the past few months. I had 674 active calorie burn because I took a long walk withe the baby in the middle of the day.

Stress levels

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

I feel a lot better now that consulting is slowing down. I feel fairly strong on the business side of things, so I’m doing OK.


Yesterday was incredibly unhealthy. Lots of chips and ice cream.

Probably didn’t help the sleep.

Investment real estate

There’s a somewhat interesting story here.

We are buying the personal home from a developer. There are three others that are similar and apparently there is someone who wants to rent one, but not buy it. In that case, we might try to buy another home as a rental ASAP.

I followed up with our agent yesterday to see if she had heard anything about the rental option.

CCIO: My business

This is the fun part! I did a fair amount of stuff yesterday!


I need to interview people in order to learn more. If I’m going to make this work (I am going to make this work), I need to understand both my customer and my competitiors.

In this case, my competition is actually freelancers. I’m product-izing a freelanced product. So, I went on UpWork and found ~10 people who work in this space and hired them all for one hour conversations.

I’m going to itnerview them all (starting later today actually) to understand, from their perspective:

  • Who their customers are
  • How they get customers
  • What makes customers happy

Then, I’ll go talk to customers.

It’s research/learning time.


I interviewed a few people yesterday to understand how much it would cost to get started with a website and how long it would take. I got quotes using WordPress and Webflow, and prices ranging from $7.5K to $1.2K.

Honestly, I went with the $1.2K

I think that’s sufficient to get the site up and running. If and when things are cranking and I have the budget, I’ll hire someone legit to make a legit site.

Outbound Sales

I anticipate a ton of the sales will come from cold outreach. So, I bought a different domain (to not break my main domain) and have it warming up on Lemlist. The goal is to have this email address super warm by the time I’m ready for cold outreach.

The question is: do I think switch to so I can do full outbound? I think so….but TBD!


My goal is 100 customers by my 27th birthday. That’s late October to get that done.

Content website business

I’ve slowed down here. I have a dozen sites out there just aging and get older and older. I’ll try to have their content ranking eventually, but for now, let’s just let these sites sit.

Acquisition Entrepreneurship

Nothing. Years down the road.

Side Consulting

Slowed way down.

Market Analysis

This project is still running, but not much going on here. Nothing yesterday.

Sourcing new work

I turned down a project yesterday.

$10K/day website

Literally nothing. I’m sorry


Lots of family time. Since things are slowing down, I got to spend time with the family yesterday. Long walk with the little guy.



Rescue Time Daily Screenshot

It’s been a while. I’ll start adding these in now that I’m back to working daily.

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 Wednesday and I have a couple itnerviews scheduled. Let’s get after it

1,370 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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