The $0-$10K/Day Case Study: Day 144

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Day 144


One thing that’s talked about a lot is the concept of timing.

Many people love to claim that it isn’t a “good time” for them to go into entrepreneurship. Maybe it’s work, maybe it’s family responsibilities, or maybe a combination of all of the above.

Many other people like to criticize that concept. They say “there is no such thing as a good time so just start.”

Both of these lines of thinking are missing the point. In short, they’re both wrong.

Here’s why: it is inwardly focused rather than externally focused.

The biggest mistake people make in business is thinking that anyone gives a shit about them and what they want to do. The customer does not care it’s not a good time, or if you should just start. The customer cares about one thing and one thing only: solving their problem.

Starting off your business thinking about whether it is a good time for you is starting off your business on the wrong foot. You need to start by thinking about your customer and what matters most for them.

Amazon is the classic example of a company that does this right. Jeff Bezos has repeatedly said he believes two things:

  • Customers want products cheaper
  • Customers want products faster

Everything Amazon does is in pursuit of those two things. From the design of the app, to the launch of Alexa (voice ordering), to Prime, to the acquisition of Ring, is designed to get products to customers faster and cheaper.

Focus on what your customer wants, at their core, and then the business success will follow.

How do I think about what timing is best for my customers?

Put yourself in their shoes: when will getting cold-called to sign up for your service be welcome and when will it be annoying?

Most likely, your target customer will be more receptive to speaking when they are less busy. If you call in the middle of a meeting, then you will piss them off.

For example, I live in Chicago. Since it’s cold as shit here, the real estate market grinds to a halt during the winter since no one wants to move then. It’s not uncommon to see the entire winter go by with very few houses added to the MLS. Once you hit May, houses start showing up on the market and then selling ASAP.

My guess is that Chicago-based realtors make ~80% of their yearly income during May-August.

Let’s say you wanted to sell something to Chicago based real estate agents, such as a service that builds websites for them. Trying to call and pitch a realtor this service in July is going to be straight-up dumb. Not only are you interrupting them while they are busy, but the fact you call now shows a fundamental misunderstanding of their day-to-day and when they are busy. Why should they buy from you when you don’t understand their business?

The message is this: align your timing with your customers, not what is most convenient for you.

Yesterday there were 1,604 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:

I woke up at 6:29 am after going to bed at 11:05, for a total amount of sleep of 6 hours and 36 minutes. Recovery was 65%

Not a bad day, as I felt good amounts of energy up until maybe 8 o’clock. I crashed at 8 though.


I didn’t exercise much, just a walk around the neighborhood with my fiancee and some workouts at home. All in, day strain was a measly 5.4.

Stress levels

I was at a 3/5, with 1 being the highest. It was a busy day, but I felt in control of the day.


Diet was coffee, fried rice for lunch, and then a chickpea salad for dinner.

2/5 with 1 being the best. Better, probably because I actually took the time to cook something for dinner.

My Day Job

I had two calls that I dialed into, but that was it.

One thing I’ve always prided myself on, especially during my first job out of college in MBB, was being able to not do a lot of work but make them think I do a lot of work. It’s a function of being able to say something smart on command. That makes your company think you’ve been deeply thinking about it, even if you haven’t. I’m now two  jobs into my professional career and I have awesome reviews across both of those jobs.

If you want to practice this skill, try forcing yourself to give a one-minute speech on a ridiculous topic with no prep time.

Example: explain why Fetty Wap’s “Trap Queen” is beautiful poetry.

5, 4, 3, 2, 1……..start talking.

It’s a lot harder than you would expect. I used to make my students practice this back at business school, and now they all work for Goldman Sachs or McKinsey.

It really works.

Investment real estate


My Actual Business

I spent a ton of time here yesterday building out my Excel tracker for what I need to help grow things. Essentially, my goal was to understand how revenue grows if I add in a few more customers per month.

As I outlined in my plan for the business, my startup will be B2B and at a price point of $300/month. If I want the business to do $170K in revenue in it’s first year (about what I did with consulting), assuming no growth, I need to average $14K in revenue per month. At $300 per customer, that means I need to average 46 customers per month.

That doesn’t seem that hard!

I also spent a fair amount of time yesterday reading online. I’ve found at least a dozen companies that do what I want to do. All of them look like complete shit. They have horrible websites, it’s not clear why they are better, and there is no one to contact for more information.

I’m going to smoke these guys.

Side Consulting

I did some work, but things are slowing down here. That’s exciting, because it allows me to focus on family and the business now!

Business plan

I did some light finish up work here. This project is almost done and should be wrapped this week.

Financial modeling

Nothing, although I’ll need to start moving on this shortly


Nothing right now

Summary presentation


Market Research & Customer  Interviews

The bulk of my day. I spent some time here outlining what the final deliverable will look like and then I shared that over with my client. Always good to get alignment earlier  rather than later.

Sourcing new work

A follow-up email with a potential Fortune 500 client. They are really slow to sign up to things.

$10K/day website

Daily post


Time with my fiancee



Rescue Time Daily Screenshot

Surprised that was a 10 hour day yesterday. Will take it though.

What I made today

Current Income  Streams

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

Total:  $893

Planned income streams

  • My Startup
  • Local Serviced Based Business  (cleaning business)
  • Affiliate
  • WordPress Maintenance Site
  • Content sites
  • Franchises
  • Dividend Income (municipal bonds)
  • 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

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: $2

  • 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: $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 $893, spent $119, which means….

Made $774 (pre-tax)

My plan for tomorrow

Tomorrow is Tuesday, and going to be totally slammed

  • Hire my modeling expert to help me out with the financial model
  • Do ~4 interviews with people for my market scan project
  • Schedule more  interviews for market scan


1,603 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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