The $0-$10K/Day Case Study: Day 167

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Day 167


Things are nuts right now. They were nuts yesterday, which is the goal of this post. I’ll focus on yesterday for this piece.

Overall, it was real estate & day job & consulting that all came into play.

I’ll describe in each sections below what happened, but the headline is this: I am easily working four full-time jobs right now, plus have a baby at home (call it five full-time jobs then!)

  • The real estate took 4+ hours between new and existing property
  • My existing consulting contract had a ton of work
  • My new consulting contract negotiation and signing took forever
  • My day job was simply annoying because it’s a shit show and takes time from my day-to-day

My day job is the one to focus on.

It’s a startup that is at an interesting point. There are a limited number of “pros” at this company who know what they are doing and talking about. A large percent of the company does not know what “good” looks like and are therefore really struggling to deliver value to the business.

I call things “amateur hour” in conversation with a friend of mine who works there and I think is highly capable.

The job isn’t a significant amount of my time, but it is a significant amount of my day-to-day stress and annoyance. I’m annoyed every time I need to divert time from my consulting to the company because the company is doing silly things and is going to go out of business.

The inevitable happened yesterday in that one of the talented people in the company quit.

It got me thinking that it’s time for me to leave too.

My fiancee and I talked and we decided I’ll leave no later than when her maternity leave is over with. At that point, I’ll go full-time on consulting. That will get rid of my salary, but it will free up time to do more consulting.

It’s objectively risky to leave a stable job for unstable consulting during the time of COVID

It could be really risky to leave a stable job, only to find that consulting hiring isn’t happening because of COVID.

But, let’s look at the “what do you have to believe to be true” analysis:

  • Since scaling my consulting, my worst month has been $14,000 in income (pre-tax)
  • My day job is roughly ~$5,000 a month (post-tax)

That means the “what you have to believe to be true” is that you’d have to believe I’d only do 35% ($5K/$14K) of my worst month ever to match my day job salary.

I think, when looked at through this lens, I think I’ll be able to at least match my consulting salary. I don’t think I’ll go to zero.

Quitting a job to be an entrepreneur makes health insurance important

When quitting, health insurance becomes even more important to think about. With that in mind, I need to find a way to get covered.

There are a couple of different ways I could do this, but the one that makes the most sense is to just join my fiancee’s plan. With that in mind, we’ll need to figure out how best to do this.

Yesterday there were 1,540 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:

Whoop didn’t work for me! Not a lot of sleep though with the baby.


No exercise today. I’m looking forward to hopefully doing a Peloton tomorrow.

Stress levels

Monday was a 1/5 stress day, with 1 being the highest.


Diet was coffee, and then vegan quesadilla for lunch and noodles for dinner. Largely vegan, but I had a Sprecher’s soda for 300 calories so not great there.

My Day Job

Random asks that caused stressed, and a key employee quitting.

Investment real estate

Two big developments here from the real estate investing front.

Our Illinois 7 unit

This building has been a thorn in our side and we’re looking to sell it as a result.

However, yesterday was an interesting day. A Tornado level storm blew through and damaged the roof and a lot of the siding on the property. As a result, our PM and realtor both think we’ll be able to get an insurance claim in to replace the roof and a lot of the building.

If we can get the place fixed up, then it’s more attractive to sell and it’s also more attractive to keep.

We have been planning to sell because our PM sucked. We only know about the damage because our new PM was at our property within an hour of the storm passing.

Maybe we don’t sell because this new PM is good.

The 49 unit deal

We had scheduled to go inspect the buildings this week. Unfortunately, the PM tested positive for COVID. We are hoping she feels better! For safety, she asked we postpone.

With that in mind, we are bumping out the inspection to early October and then can close on the deal in December.

This is better for safety from a COVID perspective, and better from a safety perspective, That gives us a few more months of data to know how many tenants are paying rent or not with COVID.

I don’t think COVID will be as big of an issue for these 49 units than it will be for a property in downtown Philadelphia or so, since these 49 units are much more remote. There are way few cases in this county since it’s remote, so hopefully, people stay healthy and life remains relatively normal.

This also solves the “how do we go to the inspection with a baby” question. No need to charter a plane anymore!

CCIO: My business

Nothing right now. Coming soon!

Side Consulting

Busy day here

Data/strategy work

I had a ton of work here to update a PowerPoint. It was a bit frustrating because I disagree strongly with what the client is asking for (it doesn’t make sense, and they’ll discover that later) but they’ve made it clear they want to leave it as-is.

New huge project

Well, I sold a big project. I’ll have a huge engagement kicking off later this week. For that in mind, that means I’ll be totally slammed balancing both of these consulting engagements.

Yesterday was a busy day to sign contracts and get everything signed up and ready to go.

With this deal, I should have enough cash on hand to close the real estate deal.

Sourcing new work

I actually fired a client. I had a guy hire me for $100 to do like ~5 hours worth of work. I took it because I think there is a lot of potential for bigger follow on projects.

But then, he wanted to chat on the phone a lot. And when I (politely) told him I don’t have time, he was shocked. He acted like he was the most important client in the world.

Bro, you are paying me $100. My other client is paying $50,000.

Giving you the same amount of time would be silly.

$10K/day website

Daily post


Time with the baby and fiancee!



Rescue Time Daily Screenshot

This excludes hours on the phone!

What I made today

Current Income  Streams

  • Job:  $170
  • Consulting Project: $650

Total:  $820

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: $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: $6

  • Gusto to pay myself: $1.50
  • Quickbooks to track expenses: $0.40
  • Google Business Email Account: $0.40
  • Fiverr for virtual support: $0
  • Hiscox business insurance: $4

$10K a day: $12.42

  • 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
  • Rhino Rank for SEO: $10.83

Real Estate Investing: $0.52

  • Legal Zoom Registered Agent (all LLC’s): $0.52

Today’s Income (pre-tax)

Topline of $820, spent $123, which means….

Made $697 (pre-tax)

My plan for tomorrow

Tomorrow is Tuesday, and I need to do:

  • Main consulting client work
  • TBD

1,539 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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