The $0-$10K/Day Case Study: Day 176

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Day 176


Is it bad if I tell my CEO to go fuck himself?

Seriously, is it?

One thing that has always helped me in my career in speaking my mind and being super transparent. People I work with constantly tell me I’m one of the most transparent people they’ve worked with. I just had a call with someone who might want to buy our 7 unit and I started the call by telling him everything that is wrong with the property.

I’m thinking I’ll do the same with my current CEO.

The guy is condescending and flat-out a horrible manager of people. If you read “The No Asshole Rule”, the definitive book about assholes in business, the best way to define them is by asking a certain question: “Do people feel energized, the same, or less energy after dealing with the person in question?”

If there is someone in your company who sucks the energy out of everyone they deal with, then they are an asshole.

The CEO is an asshole.

He got on my case yesterday for something that was his fault. I realized I had way less energy than before dealing with him, and it made me want to quit so much.

How to be a good manager

Here’s how I’m going to work as a CEO for my company CCIO that I start next year, and for acquired companies:

  • Give everyone a copy of “The No Asshole Rule”
  • Set one company-wide goal (North Star Metric) and constantly repeat it
  • Hire great people, pay them well, and share the profits
  • Take out the roadblocks from their day

It’s really simple. You’d be amazed the impact a great culture can have on business though.

Yesterday there were 1,525 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:

No whoop, but I think I slept okay.


I did a 30-minute recovery Peloton ride. I need to do a better Peloton ride tomorrow.

Stress levels

Call it 4/5 on the stress, with 5 being the highest.


Vegan stuff, including Blaze vegan pizza. Highly, highly recommend.

In fact, it got me looking into how to acquire a Blaze franchise.

My Day Job

See asshole conversation above

Investment real estate

We had a call with the banker who is providing the funding for our next 49 unit real estate deal. It ended up being an incredibly important call because he tipped his hand on a couple of things a banker normally wouldn’t.

I think the deal we are doing right now is a bit of a stretch on whether we should be approved for it. We don’t have the cash for a 20% downpayment, so we’re doing 10% down, 10% seller-financed, 80% bank financed. We barely have the cash for the 10% down as well.

He told us that the bank didn’t even let him finish pointing out the specifics of the deal, they just approved the loan in less than 30 seconds, and that the bank is really excited to continue working with us. They helped provide the funds for our earlier 6 unit purchase.

That means, even though we thought this might be a stretch, we actually are sitting in the driver’s seat here regarding future deals.

The question is: how much further can we push this? Can we get a loan on another property that’s even bigger with less down? I’m starting to think we might be able too, and have a property in mind.

CCIO: My business

This is going to be big during Q4 and next year.

Side Consulting

So many meetings.

Data/strategy work

I got paid here and I updated a couple of files for the team before fully peacing out.

Huge data project

I did some emailing with clients here, but nothing crazy. Tomorrow might end up being a lot busier.

Sourcing new work

I need to email with my contact to see if any of these potential new projects might land.

$10K/day website

Daily post


Time with the baby and fiancee.



Rescue Time Daily Screenshot

What I made today

Current Income  Streams

  • Job:  $170
  • Consulting Project: $350
  • Real Estate Cashflow (13 multi-family units): $65

Total:  $585

Planned income streams

  • My Business (CCIO)
  • WordPress Maintenance Site
  • Content sites
  • Micro-SAAS’s
  • Acquired businesses

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

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 $585 spent $103, which means….

Made $482 (pre-tax)

My plan for tomorrow

Tomorrow is Wednesday, and I have to:

  • Light work for my consulting client on excel
  • Probably some random things that will pop up during the day…doesn’t seem like it will be a busy day

1,524 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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