The $0-$10K/Day Case Study: Day 160

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Day 160


I’m officially back into the swing of things. That’s exciting and it’s good to be back. But, there’s a fair bit of stress these days in my life.

On one hand, things are great and it’s thrilling to be able to spend time with family. On the other hand, I feel guilty when not working to some degree. The reason why is the real estate deal I wrote about yesterday. I need to make every possible penny between now and December in order to pull this deal off.

I feel pressure to make money in order to provide for my family, but I also feel pressure to be there for my son. It’s a weird and new trade-off that I’ve never thought about before. My guess is that I’m not unique in new Dad’s who think this. Either way, it’s a new emotion that I need to come to terms with.

Part of why I feel bad is nothing “bad” will happen if I stopped working. Without this real estate deal, my fiancee and I would make enough money to support ourselves and our family. We would be okay.

However, we would be okay for now. As we get older, expenses will inevitably increase. The little guy is expensive now and will continue to be expensive as we get older. It will also be even more important to be “there” and present for him.

So, grinding now while he is 30 days old to be able to buy investment real estate that will allow me to work less, make more, and spend more time with him should be the clear-cut decision.

It creates pressure. That’s what I’m feeling this morning as I look through the upcoming day I have and I reflect back on yesterday for the purposes of this case study.

I’m going to make it happen. It just might not be pretty in the process.

Yesterday there were 1,547 days until I turn 30 and need to make $10K a day passively. Here’s how I spent yesterday 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’m going to be updating the plan slightly…stay tuned.

Wake up & sleep:

The baby didn’t sleep super well last night. As a result, I got just 4 hours of sleep.

Coincidentally, Whoop liked the number 4 last night. It also had my recovery at 4%.

The fact I’m getting so little sleep but am still finding a way to work during the day is a clear sign to me that perhaps I was being a bit of a little bitch in my past every time I “couldn’t” get out of bed in the morning.

Obviously, I could have. I’m doing it now because I have to. I could have done it back then as well.


Whoop had me down at a day strain of 14.8, largely driven by a 30 minute workout with the Peloton. It was a great workout overall and I had a blast with it. These workouts are super helpful for me to maintain energy levels despite everything that is going on baby-related.

Stress levels

Stress isn’t bad. There is pressure to perform, but I’ll get it done.


Still sticking with the vegan diet in order to help energy levels as much as possible. I had coffee and oatmeal with berries for breakfast and noodles with tofu and veggies for dinner. Overall, not too bad.

The bad part was the soda I had. Time to cut those out too. I cut animal products out, why not cut out soda too?

My Day Job

I had a few things to do here, but nothing crazy. Probably sub 1 hour.

Investment real estate

Busy day here on two fronts.

On our 7 unit, I have been coordinating with a new PM. We are discussing a transition plan with him tomorrow, then I’ll probably call and give the other PM the heads up that they are fired.

Honestly, I think we could probably sue for negligence. I also can prove, in writing, that at best she was incompetently deceptive and at worse, lied to us. I really want to tell her off when firing her.

That’s not the right thing to do though. I don’t care about telling her what’s on my mind as she has personally lost us more than $18K. I care about her being pissy and not getting the keys to the new person. Once the keys are there and she is officially out of our lives, I’ll be much more willing to be transparent with her and with online review services exactly how I feel about her.

On the 49 unit acquisition deal, we had a call yesterday with the banker there. He wanted to go over deal terms, specifically interest rate and amortization. With interest rates being low, we’re going to lock in a 4% interest rate for 5 years. I’m happy with that and think it’s a good deal for everyone.

My Actual Business

I’ve put some thought into this during pat leave. This is definitely my focus in 2021.

Side Consulting

Up and running here with my first project.

Strategy development via data

I’m working with a firm on a strategic project by providing some pretty heavy data analytics to support the project. I spent yesterday going through the datasets to get familiar with them.

Sourcing new work

Heard from an old client that he is interested in working together. I’ll follow up with him today to see what the scoop is.

$10K/day website

I worked on a couple new posts on my phone while cradling the baby in the baby bjorn.


Lots of family time with the three of us!



Rescue Time Daily Screenshot

Not a ton of hours here as we wrap up into things

What I made today

Current Income  Streams

  • Job:  $170
  • Rental Income (13 rental units): $43
  • Consulting Project: $625

Total:  $838

Planned income streams

  • My business, which I’m calling CCIO
  • Content Websites (NOT $10K)
  • Micro-SAAS
  • Business Acquisitions
  • Franchises
  • Hotels
  • Dividend Income

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

CCIO 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: $2.30

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

$10K a day: $1.57

  • 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 $838, spent $160, which means….

Made $678 (pre-tax).

My plan for tomorrow

Tomorrow is Tuesday and I plan to:

  • Couple meetings with my new consulting client
  • Property management hand over
  • Call with a roof guy for our 7 unit (on top of everything else, there might be a roof issue)
  • Book time with the potential client who reached out

1,546 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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