The $0-$10K/Day Case Study: Day 161

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Day 161


This is unbelievably hard.
I’m now 24 hours into working and being a dad. The past month has been great because I’ve been able to largely be off and spend time with my fiancée and the little one. I’ve loved it
Yesterday was the first day where I had to do both dad and work. It didn’t go well.
He had barely slept the night before, so I was exhausted. I made a bunch of mistakes that I normally wouldn’t have made. That made work take longer as I worked to fix those mistakes.
His mom was with him most of the day, but that made me feel guilty because I wanted to be with them since they are what matters to me. There’s a horrible feeling when your child is crying. My fiancée told me she’d handle it and I should go back to work.
That sucks to hear. That sucks to see.
So, what’s the ‘so what’ to my complaining here?
Three things come to mind
First, I was a little bitch for complaining of being tired and not working through less hours before. This is hard and I’m surviving, so I was definitely a little bitch back then!
Second, the next month is going to probably be about the same. The baby is one month old, and we keep seeing two months as the point when babies get good at sleeping, at least to the point you aren’t exhausted on a day to day basis.
Third, I have to figure this out and get it done. I need to balance what is essentially two full time jobs, being the best dad possible, and being the best fiancée/husband possible. The stakes are high and I can’t mess up on any of those areas.
Again, this is hard. But I can’t be a little bitch about it. I need to be the best I possibly can across all of those dimensions, without complaining. My family deserves as much.

Yesterday there were 1,546 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:

Sleep was low as you’d expect. I got 2 hours and 25 minutes, with an overall 17% recovery score. Talk about not a lot of sleep and a shitty recovery!


Whoop had me down at a day strain of 14.8, even though I didn’t end up working out there.

Stress levels

Not a lot of stress, mostly just not a lot of sleep.


Diet was relatively small in that I didn’t have a lot of food. That’s of course not healthy, but I didn’t really have time to do much else. I ended up having coffee and cookies for breakfast, spinach and beans for lunch, and then ordered Indian food for dinner.

Overall, it was vegan so that’s always a plus.

My Day Job

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

Investment real estate

Fun day here.
We started with a call with the guy we’d like to be our new PM. He impressed us, and he told us that we need to have everything rented by Thanksgiving or it won’t rent this year since people don’t move in the cold.
Today is early August, so we have three months until then.
Our existing PM contract says we need to give them a 30 day notice if we want to cancel. In other words, lose 1 of 3 months the other guy will need to rent the units.
That’s too tight of a turnaround.
So, I checked Stessa and saw that we paid roughly $75 a month to the PM consistently to manage it for us. We offered the PM the $75 for this month if we can have the other guy managing it within the week.
Why do this?
Essentially, we’re “buying” our new PM an extra month to get the units rented. I’m

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

The hours are about right, but coupled with no sleep, is a total killer.

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: $129.73

  • 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
  • Ordered Indian Food: $40

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 $200, which means….

Made $638 (pre-tax).

My plan for tomorrow

Tomorrow is Wednesday and I plan to:

  • Couple meetings with my new consulting client
  • Sign new property management contract
  • Lots of new excel work for that new consulting client

1,545 days until I turn 30. I’m making $10K a day passively by then

Dean Woods

Dean Woods

Dean’s goal is to create $10,000/day in passive income through entrepreneurship. Too many people write “success porn” that skates over the struggles many face in entrepreneurship. His goal is to create something real that highlights the lack of sleep, disappointment from family, and setbacks you really face in entrepreneurship. The hope is that $10K a day swill inspire someone else out there to make their entrepreneurship dreams happen. Dean Woods is side hustling and working a full time job to kickstart his entrepreneurial path. Prior to this life, Dean was a management consultant. Dean graduated with honors from The Wharton School.

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