The $0-$10K/Day Case Study: Day 136

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I’m spending a lot of time thinking about the next step right now. I absolutely love what I’m doing, and love life in its entirety. I love consulting. I think anyone who wants to make money on the side should start with freelancing.

Consulting has taught me how to sell, how to get clients, and how to profitably go from $0 to $200K in a year.

My problem with consulting though is that I am bored. I think that’s because I’m “maxed out.”

I’m doing $200K in work a year right now. That’s about all I can do as-is right now.

The downside to consulting is that almost every project is different. I cannot build systems that allow for scalability.

Sure, I could hire a bunch of people. I could hire sales reps to grow the business.

However, the type of work I do is consulting for high profile private equity firms, hedge funds, top-tier startups, and senior executives at Fortune 500’s. You need to be a smart person to hang with these guys: they are Ivy Leaguers and can poke holes in logic in a second if you aren’t crisp in your thinking. That means I would need to hire equally smart people to be able to hang with them. They will run me $100K a year, or more.

I don’t think I want to scale a consulting business. Consulting has been good to me, for sure.

But, it’s time to scale my other business.

How I’m going to collect feedback for my business:

It’s time to get scraping.

I set up a new gmail account ( I’m now in the process of warming up that email account, which essentially means making it look like a real email. If a brand new email starts sending out a ton of emails, it looks like a fake account and that email will get flagged as spam. Then, everything I spend will go straight to spam and we don’t want that!

Next, I use LinkedIn. I have a paid LinkedIn account, which gives me access to something called Sales Navigator. Sales Nav essentially allows me to find do very detailed searches. For example, I could say I want to find all:

  • Directors of Strategy
  • Who live in NYC
  • Work for companies bigger than 500 people

Then, Linkedin will give me a list of everyone who fits that criteria. Let’s say that is 1,000 people.

Now, Linkedin’s value solely comes from the fact they own that data. Linkedin doesn’t let you export that data.

So, I break the rules a little bit and use a software called LinkedHelper that let’s me download all of those individuals in an Excel file.

I immediately take that file and then upload it to a nifty piece of software called or FindThatLead to find all of those people’s email addresses. This software will find ~75% of email addresses, so out of the initial  1,000 we’re down to ~750 people who have responded.

Then, I’ll use Neverbounce to verify that the email is real. I’ll get ~75% approval rate again, so now we’re down to ~560 valid prospects. This step is extremely important because it keeps my email address looking good. If I use shitty emails that bounce back, then it makes my email address look like spam.

Now, I’ll load these email addresses into Woodpecker, my favorite cold email sequence software. I’ll set up a multi-touch sequence to automatically email people for me and ask if they are willing to speak on the phone for 30 minutes so I can interview them.

I’d expect to see a ~5% response rate here. So, out of my 560 prospects, I  should expect 25 willing to hop on the phone.

I want to interview 150 people. So, I need 3,360 valid email addresses.

I’m warming up my email address now and will be ready to start blasting out emails within the next few weeks!

Sorry consulting-it’s time to start my own business!

Yesterday there were 1,612 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 5:25 am after going to bed at 10:47, for a total amount of sleep of 6 hours and 15 minutes. Not a great amount of sleep, which made me tired quickly during the actual day.

Recovery was at 47% as a result. I felt the lower recovery today.


I went on a run again. Solid 6.5 miles and a bit of an adventure around the entirety of Chicago. It was slow for me, but a great run and a good time to do so.

Stress levels

I was at a 3/5, with 1 being the highest. For some reason, things have been spiking there.


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

3/5 with 1 being the best.

My Day Job

It was a Friday. I had a few meetings that I attended, but nothing crazy.

Investment real estate

Nothing here

My Actual Business

I’m so excited on this!

Side Consulting

Still busy with lots of projects.

Business plan

Nothing here.

Financial modeling

Had a call here with the client. Some tweaks, but we’re still close to being done.


Nothing here.

Summary presentations

Ugh. This client is pissed. I also don’t really care. I’m pretty done with this project. It’s been dozens of hours so my take home is going to end up being below minimum wage.

Market Research & Customer  Interviews

I had a couple of calls here that went well, and I’ve been doing more prep like setting up my handover Google Drive here.

I’m excited for this one for sure.  I think things will go well here. I hired another researcher to get me more market data for $25.

Sourcing new work


$10K/day website

The daily post.


My fiancee and I spent some time together during the day (she was pretty busy actually) and watched Amazing Race together at night.

Definitely a good and fun day together.


Nothing misc today

Rescue Time Daily Screenshot

Back above 8 hours a day. I think my work week is tracking for ~55 hours or so this week.

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: $27.30

  • Gusto to pay myself: $1.50
  • Quickbooks to track expenses: $0.40
  • Google Business Email Account: $0.40
  • Fiverr for virtual support: $25
  • UpWork for slides:  $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 $1,038, spent $151, which means….

Made $887 (pre-tax)

My plan for tomorrow

Tomorrow I need to:

  • Sleep
  • Start doing some internet scraping
  • Maybe do some follow-ups here and there for work

Let’s get after it!

1,612 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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