Who is Dean Woods?

You can call me Dean….hi!

That’s not actually my real name, but it doesn’t really matter much. I’ll tell you a little more about me though.
As of the most recent update to this page, I’m 25 years old, married, live in Chicago, and make approximately 8X the average American salary. I love my family, spend fall weekends watching football, and make my family breakfast and dinner every day.
From a business perspective, I graduated with honors from The Wharton School, routinely ranked as the number one business school in the world. After graduation, I worked for Boston Consulting Group (BCG), routinely ranked with McKinsey as the top firm in the world, where I advised Fortune 500’s on how to handle their most pressing issues.
Since leaving BCG, my entrepreneurial path has covered a variety of themes. I’ve learned, and write about:
  • Bullshit business models
  • Consulting
  • Starting a company
  • Growing a company
  • Buying a small business (typically $2-$5M EBITDA), sometimes called a search fund
  • Multi-Family investment real estate
While I write my wealth building plan in far more detail elsewhere, the high-level strategy is simple: build cash flow positive businesses, like consulting, then invest heavily in cash flow positive assets like multifamily real estate.

The Goal

My goal and expectation is to make $10,000 dollars a day, passively, by the age of 30. If you notice on every page of this website, there is a day counter that logs how much time is left. I live by that day counter.
The goal is a world where I can control what I do, when I do it, who I do it with, and who I do it for. If I want to get out of bed at 10AM then go watch my child’s after school sports game or their play, then I want to be able to do that. If I want to focus on my businesses because I love the value they provide to the world, then I want to be able to do that and focus on that. $10K/ day is really freedom.
$10K a day is the goal. And I’m working on that goal publicly.

What is the $10K a day case study?

The case study is my public journey to reach $10K a day at 30. Every work day, I’ll write a post on the case study that highlights exactly what I did yesterday, what I’m doing tomorrow, and what I’m thinking about in this journey. In short, you will have a front row seat into my office, my head, and what the day-to-day looks like.
As a warning, it’s not going to be pretty. I’m not going to be talking about how amazing my life is flying around on a private jet or what new penthouse apartment I’m going to buy.
I’m going to write about stress. I’m going write about how worried I am about different things. I’m going to write about drinking so much coffee that my stomach hurts from the acid.
I’m going to show you the real world of entrepreneurship and why it really sucks. I’m writing this case study publicly for a few reasons.

#1: There is a fundamental misunderstanding on how to make and achieve wealth >$10M

Here’s a really interesting thought exercise: do you know how to get $10 million in your bank account?
You probably have a good idea on how to get to a million dollars (invest in the markets and leave it there forever) and how to get to a billion dollars (start the next Uber), but do you actually know how to do $10M?
Asked differently: do you know how to make significantly more money than you can just by living frugally and investing, without launching a big new startup?
Here’s what I mean:
Investing in a $401K won’t get you to $10M
You’d need to put $50,000 into the markets every year for 35 years at 8% return. Very few can afford to do that put that much money into the market for that long.
You won’t get to $10M via corporate
Let’s say you bust your ass and make $1M+ or more per year for a Fortune 500. Most Fortune 500’s have ~50 employees who make that much out of a 100,000+ employees, so the odds are against you anyways to get to $1M in salary.
If you do make it, you’ll get there at the end of your career (say 50 years old) and will only work for a few years at $1M salary. When you make$500K post taxes, you need work for ~20 years, or until 70, to get to $10M.
Starting and selling a startup isn’t the big driver of money either
There are a lot more people worth $10M+ than those who started and sold a company venture backed startup (350,000 American families worth $10M vs <1,000 startups)
So, how do you actually make $10M?
This part is fundamentally misunderstood. My hope is the daily case study how to make $10M, consistently, and allow you to live the life you want.
Answer: it’s not live a shitty life and depriving yourself of Starbucks.

#2: I wish this already existed

If you look in any book store or success-oriented website, you’ll find countless case studies and examples of how people have reached their goals in business and life. I’ve read them all, and if you’re on this website, you’ve probably read them too.
There is a huge fundamental flaw: they are all retroactive.
It’s one thing to hear successful people talk about the slog they went through for years as they built their business. It’s almost taken for granted. However, there isn’t a great example of a daily look of the shit, stress, disapproval, and failure you go through. I would pay good money for access to Mark Cuban’s and Brian Chesky’s daily thought process as they built their businesses.
I’m not saying I’m going to be Mark Cuban. But I hope this case study provides some value to someone out there interested in going down this path.

#3: Reset both the “Entrepreneur” and the “CEO” narrative

There are two absolutely ridiculous narratives out there in the world right now. Both are wrong, and both negatively impact the world’s perception of business.
First is the “entrepreneur” narrative. If I see one more video of of a 17 year old “guru” with a rented Lamborghini telling me how “Dropshipping is the shit,” I’m going to lose my fucking mind. These guys are not only morons, they use deceptive advertising to take money from people who need it.
However, they also hurt the country’s entrepreneurial spirit. There are so many people out there who tried to launch a Shopify dropshipping store in a “four hour work week,” failed, and thought they weren’t meant to be entrepreneurs so they stopped trying.
I believe if these dipshit guru’s hadn’t pushed the “success is easy” message, more people would go into entrepreneurship with the expectations of significant struggle to make it work. I think better expectations keeps people in entrepreneurship. This case study hopes to be a calming voice on the other side that shows entrepreneurship is fucking difficult.
The second is the “CEO” narrative. There are people setting up guillotine’s outside of Jeff Bezos’s house because “CEOs are overpaid and don’t work while their employees do everything.”
Not only is this beyond wrong, it shows a functional naivety in the person who says it. I’d bet anything that person hasn’t met a CEO. I’ve yet to meet anyone who actually knows a Fortune 500 CEO dismiss the amount of work they put in.
I work with and for CEOs. I am a CEO. We all work 100+ hours a week. We all see a therapist to deal with the stress.
Also, as of this writing, Jeff Bezos is worth $200B and Amazon’s market cap is $1.7T. Grossly simplifying, that means he created $1.5B in value for other people.
Again, at this time, the largest owners of Amazon stock are Vanguard, Blackrock, T. Rowe Price, etc. Guess who invests their money there? Retirees and pension funds.
Said differently: Bezos has created $1.5T in value and retirees are benefiting.
Again, this case study should hopefully provide at least one data point in the opposite direction to the common, bullshit, and frankly naive narrative.

#4: Keep me honest

I’m going to reach the goal of $10K a day at 30. That is just going to happen because failure isn’t an option. Every day, I’ll keep working to achieve it.
But, it helps keep me honest on that daily pursuit if I write it here. It forces me to calculate the exact amount I made each day. Since $10,000 is a nice easy number, it’s easy for me to see what percent of the way I am to $10K.

The case study ground rules

Let’s set some ground rules for this case study. These rules are how I’ll run everything on this site and should hopefully be fair to you. The list of ground rules might expand over the years, and I’m 100% open to new ones. Feel free to send me any new ideas for ground rules.
For now, here’s what I have in mind:
#1:You are not going to be sold a bullshit course, or any course 
As you can see from above, I think the Lamborghini course sellers are parasites. I’m not going to join that group.
#2: You get the most possible transparency
You’ll get daily insight into what my wife and I are thinking about and talking about. You get full access to our personal finances in the form of a daily case study post. I’ll catalog revenue, costs, and profits and where those line items are going.
This ground rule is phrased as “most possible” for a reason. A lot of my work is under NDA and I don’t want to publicly break NDA. For example, I’ll describe a client as a “technology company” instead of “Apple.”
#3: No Bullshit
I’m not going to bullshit you. When something is difficult, I’ll tell you. I’m not going to coddle you as a reader and tell you that your wildest dreams are possible with 4 hours of work a week and 3 easy payments of $997.
That is pretty much lying to you. I’m not going to lie to you. You can handle the truth.
#4: I’m not going to give you the “get rich quick” guide or the “step by step guide” 
If you are looking to get rich quick, then this is the wrong site for you. Tai Lopez and Project Life Mastery are happy to take your money in exchange for selling you false promises. Don’t say I didn’t warn you.
Similarly, I won’t write the bullshit guides about “how to start a blog” that show you each literal step in creating a website. There are unlimited articles online that show you that.
#5: If you troll others in the comments, you need to back up your claim with credentials
My favorite person online is the individual who gives out financial advice but doesn’t have a dime to their name. Similarly, wantrepreneurs who critique strategy but haven’t gotten off the couch.
If this is you, please know that your strongly held opinion holds no weight here. If this is you and you want to learn from others instead of bash others, then welcome!
#6: Strong opinions loosely held is our intellectual duty
On the contrarian point to ground rule #4: if you see something in this site and disagree with it, it is your intellectual duty to speak up! None of us have all the answers, or even some of them! We are all here to learn and that only happens when we disagree and engage in intellectually interesting conversations.
So please speak up and share your thoughts. Let’s all learn from each other.

On Dean Woods

Dean Woods is not my name. In fact, it’s about the most generic name that my wife and I could come up with.
This case study is completely anonymous. Everything in here will not have my real name. I will also not provide the exact address of property we own for that reason as well.
There are a couple reasons why:
  • Out of respect for my clients, who didn’t sign up to get their work talked about on the world-wide web
  • Out of respect for our tenants, who don’t want to get harassed. I also don’t want them knowing they’re paying rent to a couple under the age of 30.
  • Out of respect for my wife. She has a day job, and while the most supportive person in the world and the love of my life, she also didn’t sign up to have her day job compromised in any way because her husband was discussing financial matters online
Let’s all reach $10K a day together, the old fashion way and the only damn way to do it: with a shit ton of grueling work. Here’s just one story of work.
This is the $10K a day case study

Updated Summer 2020
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