The $0-$10K/Day Case Study: Day 135

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Day 135


Objectively, things are really good.

I have a loving family, a lot of clients, and a solid income. We own more than 10 income producing units. I have clients signing up constantly to work with me.

But, something feels off. I don’t feel good.

One thing that YC talks about is founder depression, where company leaders feel sad and deal with a lot of emotions. I don’t think I’m depressed, not at all, but I don’t feel as good as I theoretically should.

My hypothesis was that thing that felt off to me was my debt. I had a fair amount of it and I thought that debt was weighing me down as an anchor.

Turns out, it wasn’t the debt. I paid it off in full and honestly didn’t really feel anything in the process.

I’m not quite sure what it is, but it’s on me to figure that out as I move forward. My guess is the disjointed nature of my day, bouncing between so many clients, is playing a big part here.

This is the side of entrepreneurship you don’t see on Instagram. I’m not posting pictures in a Lamborghini right now using #entrepreneur.

I’m grinding, and wearing myself down in the process.

I think I need to exit consulting ASAP and begin to move into building my actual business.

Is my timeline right? I’m not sure anymore

I’ve written here before that I have a big plan for my business. My plan has been to try and grow it, starting Q1 of next year.

I’m wondering now if instead it makes more sense to accelerate that timeline. That helps me get out of consulting sooner and then allows me to zero in and focus on growing the business.

On the plus side, that would be a ton of fun and help me grow a lot more. On the downside, it means lowering my income because the business will make less than consulting does.

Of course, that is a BIG assumption. I’m not actually sure if that is true or not. I’m assuming that consulting is more profitable than the business.

Maybe that assumption is wrong and I shouldn’t be thinking about it that way?

It’s time to start scraping emails and conducting customer discovery interviews.

Yesterday there were 1,613 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 #1:  The Job & Side Hustle Phase.  You can read more about the phases and my plan to get to $10K/a day at 30 here.

Wake up & sleep:

I woke up at 7:33 am after going to bed at 11:19, for a total amount of sleep of 7 hours and 20 minutes. My mind was spinning last night, which was great, but it meant I needed to take a Unisom to fall asleep. That blows because it made my morning all groggy.

Recovery was at 70% though so I was pretty happy about that.


No exercise outside of some pushups and sit-ups at home. Basic workouts and staying active are always goods things.

Stress levels

I was at a 2/5, with 1 being the highest. For some reason, things have been spiking there.


Diet was coffee, some noodles for lunch, and dinner was pasta. Generic and bland.

3/5 with 1 being the best.

My Day Job

It was a Thursday and I’m not sure what I did for work during the day.

Investment real estate

We heard from the property management team that has been struggling to rent our building. They got an application from someone that seems very good. His pre-tax income is 4X monthly rent, nothing wrong in his background checks (read: no arrests), and his credit score is 720+.

Those are really the only things you need to know about prospective tenants. Actually, knowing more isn’t a good idea.

Fair Housing Laws are designed so shitty landlords don’t discriminate against possible tenants. For that reason, I just want to stick to the pure numbers:

  • Income to rent ratio (number)
  • Credit  score (number)
  • Number of arrests/sexual assault convictions (number)

If those numbers are all good, then I don’t care about anything else. I don’t need to know their name when they apply, I don’t need to know their gender, I don’t need to know anything. The only reason I know it’s a “he” because the property manager referred to the applicant as “he” in her email.

Let’s hope the property manager gets him into the building, that he pays rent on time, and stays for a while!

My Actual Business

I talked about this a bunch above. I think it’s time for me to start going after this more aggressively.

Side Consulting

Still busy with lots of projects.

Business plan

Nothing here. I think it’s just a little touch-ups here and there.

Financial modeling



A couple of  meetings

Summary presentations

A couple of tweaks, but nothing crazy

Market Sizing

A few hours of work, but not much

Market Research & Customer  Interviews

A couple hours of learning about the industry. I hired my researcher on Fiverr to find me analyst reports, 10k’s, info about companies raising money, and more. It costs me $30, but saves me dozens of hours of research. Once she comes back to me with the material, I’ll sit down and read it all in a day or two.

Sourcing new work

Nothing…..I don’t want to source new work for a while.

$10K/day website

The daily post.


A nice day and night together with my fiancee. I love that we’re both working from home right now


Nothing misc today

Rescue Time Daily Screenshot

I’m actually extremely surprised that this is under 7 hours. I absolutely expected it to be much higher.
I might be really burned out and in need of a laid back few days!

What I made today

Current Income  Streams

  • Job:  $170
  • Rental Income (13 rental units): $43
  • Business Plan: $145
  • Framework: $250
  • Customer Interviews: $430

Total:  $1,038

Planned income streams

  • My Actual Busines
  • Local Serviced Based Business
  • Affiliate
  • WordPress Maintenance Site
  • Dividend Income
  • Micro-SAAS’s
  • Hotels

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
  • Groceries: $0

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: $2.05

  • 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

Consulting Business Expenses: $52.30

  • Gusto to pay myself: $1.50
  • Quickbooks to track expenses: $0.40
  • Google Business Email Account: $0.40
  • Fiverr for virtual support: $30
  • UpWork for slides:  $20

$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 $1,038, spent $169, which means….

Made $869 (pre-tax)

My plan for tomorrow

Tomorrow I need to:

  • Finish up with some work for my new client on the interview side
  • Blow through my inbox
  • Go for a run

Let’s get after it!

1,613 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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