The $0-$10K/Day Case Study: Day 133

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Day 133


Twitter is absolutely a funny animal and it’s own beast. You don’t need to go far to see a bunch of bullshit, most of it political, and most of it completely missing the bigger picture. I’m talking about both sides of the aisle here as well!

But, there are some really interesting learnings there as well. I recently was on the phone with a senior executive at a fantastic company. This executive is relatively young. It naturally came up in conversation how he learned a lot of the content that helped him succeed at such a young age.

His  answer: Twitter

The way he viewed it, Twitter allowed him snippets of insight into how fantastic leaders like Paul Graham of YC fame and other well-known business minds think.

This is a fair point, because it’s helpful to understand as much as you possibly can from people who have been there and done that.

On the other side, there are two big downsides.

First, there are a lot of “armchair quarterbacks” on Twitter. You know the type: they haven’t actually done anything at all in their life but are quick to tell you why you are wrong and won’t succeed.

Secondly, a character-limited tweet doesn’t give you full insight into how someone thinks or does things. You might get brief snapshots, but you really need to the full-feature movie to understand. That’s the same problem with biographies. If someone writes a biography on Dean Woods down the line, there might be a chapter about how busy I felt while handling 9 projects at once. However, you don’t really see and appreciate that fully until you read the daily case study and see the full picture.

Bringing this back to Twitter. If you follow people who have  “been there and done that” and tweet frequently so you get a running stream of how they are thinking about something, then that is someone to learn from. That’s what this executive did, and that’s what I try to do too.

One account I follow and highly recommend is @Amysundae. She’s a partner at one of the best VC’s in the world (Sequoia), and is an alum of Harvard, Microsoft, Facebook, and Uber. She constantly says smart shit.

She tweeted this the other day:

On the surface, this makes sense. The skill-set of selling a high-priced product and delivering customer service on that product is important. Mark Cuban and others have echo’ed the idea that selling is one of the most important skill sets you can have.

But when you look at it from a deeper perspective, think about the context behind what she is saying:

  • She personally went to Harvard and works/worked at maybe 5 of the top 7 companies in the history of the world (Don’t think she was alive when Standard Oil was a thing!). She knows what makes a company works and “what good looks like.”
  • As a VC, she spends all day evaluating founders and business ideas to determine their merit. Her job is based on predicting success

When you think about these two factors, this five-lined tweet just saved you years of work from someone who knows exactly what the fuck they’re talking about.

Go try to sell something today. It doesn’t matter what it is (drugs and prostituting yourself don’t count). Get someone to give you money for a good and/or service.

That’s a more valuable learning experience than Harvard.

I went to Wharton (#1 business school). I learned more in my first six months selling than I did in my entire time at Wharton.

Go sell!

Yesterday there were 1,616 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 5:55 am after going to bed at 10:28, for a total amount of sleep of 6 hours and 44 minutes.

Recovery was at 72%, which is still a positive trend. That means it’s time for a big workout tomorrow and by doing a ~8 mile run tomorrow.


I did about 15 minutes of weights and abs in my apartment. Couple hundred pushups, nothing crazy.

Stress levels

I was at a 4/5, with 1 being the highest. It was a very busy day, but a successful day from a sales perspective (hence the piece about sales above!) so things are good on my side.


Diet was coffee and eggs for breakfast, some nothing for lunch, and dinner was chicken and vegetables.

Fairly normal day, making up on the veggies after not having any yesterday and in anticipation of the run tomorrow.

3/5 with 1 being the best.

My Day Job

It was Tuesday and work day, but I did shockingly little work for the day job. Maybe an hour or two here or there.

I think I’ll struggle to leave remote work and going back to normal work. Remote work has enabled me to do only a little bit of work and get away with it because my output is still good. I don’t need to pretend to look busy in the office for 8 hours.

It will be interesting to see what happens when remote work ends and if I can get away with not doing it anymore.

Investment real estate

Nothing here today.

My Actual Business

I have my business plan written. I’m going to begin executing on it in August.

Side Consulting

Busy as hell, but the project count below is declining.

Business plan

Heard back from this client. I have a call with him tomorrow

Financial modeling

I did a few hours of tweaks but we should be just about done now.

Financial modeling #2

I did some tweaks here, but nothing crazy.


A meeting or  two, but that’s it

Summary presentations

I was supposed to do this but ended up not doing it. It means my tomorrow is going to be busy as a result.

Market Sizing

I did the work here. It was actually a really fun project for a few hours. I found a website that lists the number of Shopify stores, which made the market sizing really straightforward to do.

Market Research & Customer  Interviews

This project is about to sell and go through. It’ll be a month or so of work for $12K. I’m excited for this because it’s right up my alley and a good price point.

Sourcing new work

I’m also negotiating with a Fortune 500 right now to work with them in a strategic capacity. If this one sells, I will have 9 projects going on at once. I need to throttle that back down.

$10K/day website

Daily case study post


My fiancee and I took a couple walks together


Nothing misc today

Rescue Time Daily Screenshot

Double-digit hours for the first time in a while! It was a busy day.

What I made today

Current Income  Streams

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

Total:  $993

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: $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: $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 $993, spent $119, which means….

Made $874 (pre-tax)

My plan for tomorrow

Tomorrow I need to:

  • Go for a run
  • Eat Healthier
  • Finish up the slides that I punted to today
  • A bunch of day job work
  • A couple small clean up things for projects
  • Hire a lawyer!

Let’s get after it!

1,615 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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