Let me tell you a tale in reverse. Let’s start with the end, and then look at how we got there.
The conclusion
Meeting other writers can be fun. It’s really cool to meet the author of the best-selling book on finance in the past two years. It’s really cool to chat with the author of the best-selling book on finance of the past two years. Many of these topics had nothing to do with writing or finance.
You might ask me “How did you meet?” I’d say we met on Twitter, and then decided to meet up when Morgan visited NYC. It’s not the whole truth. The truth is, it’s not the whole story. This meeting should never have taken place. Our meeting was largely the result of a fluke.
Let’s get to the “how did we arrive here” part. Keep reading.
April 2019,
In 2019, during my senior year in college, I was offered the option to defer enrollment for full-time MBA programs at several top business schools. In a normal business cycle, students work for 2+years before applying to a business school. The deferred option changed the way that students applied to business school. They could apply as seniors in college and, if they were accepted, would work for 2-5 years prior to starting graduate studies.
My alma matter, Mercer University is a great school, but a regional degree in Georgia from a good university won’t impress any employers at the top. A degree from Columbia, Harvard or Booth (Chicago’s business school), however, would be a better choice.
I was 22 years old and had no idea of what I wanted to do in life. Pursuing an MBA at a top-10 school seemed like the obvious step to improve my future career prospects.
I spent months studying for the GMAT, applied to seven of the best business schools offering these deferred-enrollment programs, and landed interviews at Booth and Columbia.
Booth was the school I chose after researching both schools. Chicago was an exciting city, the campus was gorgeous, the school was higher ranked at the time and my girlfriend from Milwaukee wanted to return home. Booth seemed like a good choice, especially if I got accepted. In April, I flew from New York to Chicago for the interview.
Visiting Booth School of Business, April 2019. Not a huge fan of the tie.
The interview went well except for one minor hiccup: I was the lone applicant in my class without a full-time position lined up.
I decided to return to Mercer after graduating from college in May to play football for one more season the following fall. It wouldn’t be a big deal except that these deferred-enrollment programs require December graduates to apply to the following Spring (in this instance, May 2020).
I was in a strange position as a spring 2019 grad who would still be attending classes in fall 2019. I worried Booth would cancel my app and force me to reapply next year if they found out I would stay at Mercer one more semester. I wanted to secure a seat in grad school now, so my fall plans were kept a secret during my interview.
I had a finance intern with GEICO during the summer. When future plans were discussed in my interview I mentioned my internship and said that it would result in a full-time job offer at the end of the summer.
Conflict avoided? I thought so.
Two weeks later I flew back to New York for an interview at Columbia. When I arrived at JFK, I thought I would use the same story as a cover for my fall 2019 plans.
“Dear Jack Raines: This year’s cohort of Booth Scholars were very competitive and unfortunately, you were not accepted into the 2019 cohort. We hope Booth remains in your mind and that you will consider reapplying.
My hopes of using an MBA to launch me into a career in corporate finance were crumbling before my very eyes.
” Shit,” was my first thought. What if I also don’t get in to Columbia? Do I have to change my story if I don’t get in? Only 24 hours until my interview. “
When I was driving to the hotel in my taxi, I realized what I had done wrong.
I lost my advantage as a candidate by hiding my Fall 2019 plans. This almost guaranteed me a rejection.
It’s unlikely that being honest during my Booth interview would have secured my admission. After all, it was a highly competitive class. I could have lost to other applicants, or the school may have asked me to reapply for 2020.
If 200 students have the same GMAT score and academic background, then the candidate doing a summer intern with an insurance company will lose out to dozens of other candidates who are receiving full-time job offers from McKinsey Bain and Goldman, unless he can gain an advantage.
When the Columbia admissions officer questioned me about my plans, i told the truth.
“I am in a unique position where I will be graduating next semester but have the chance to play football again. After a concussion and multiple torn tendons, I was a walk-on and now I am a starter. It’s been my goal since I was in high school and I must see it through. “I know that this does not fit into the usual timeline for this program but I do hope that the admissions committee still considers my application.”
Two weeks later I received this email:
“Congratulations! “We are thrilled to welcome you at Columbia Business School!”
March 20
I worked for five days in the corporate finance department of UPS’s Atlanta offices after finishing school in December. The pandemic sent everyone into an indefinite purgatory where we had to work remotely from home. As with most people now stuck in their apartments, I became bored. When I became bored, I began trading stocks. It was the most volatile market ever, and I had nothing else to do.
March 20,21
The whole stock trading thing worked. One year later, I had made about $400,000. After a few years of trading SPACs with good results, I wondered if anyone would pay me for writing about them.
After searching “how to earn money by writing about stocks”, I found that Seeking Alpha paid $100-150 per premium article. I created an account and began writing. I was able to write a decent piece that required minimal revisions in just 2-3 hours. It’s a good way to earn extra money for weekends.
July 20,21
My company wanted to see me in the office as soon as possible, but I was determined to travel before going to New York to attend business school. Both choices were in conflict, so I gave my two-week notice and purchased a one way ticket to Barcelona. But I also wanted to earn some money abroad. How was I going to achieve that?
Writing.
I have written 15 or more pieces for Seeking Alpha, and two chapters of a book that I’ve been working on called The inefficient market hypothesis. I then applied for a variety of remote writing jobs, including a staff writer position at Morning Brew and a part-time job at Collaborative Fund, where Morgan Housel also worked.
After I was worried that my resume might be overlooked, I sent examples of my work to Housel and Morning Brew CEO Austin Rief as well as other people who worked at the companies where I applied.
After a few weeks, I still had not received any job offers. I was in the classic “chicken or egg” dilemma. You need writing experience to land a job as a writer, but you can’t get that experience without a job.
Around this time I noticed that many people were publishing their blogs/newsletters through a website called Substack.
So I said to myself “Screw this, I’ll start a blog and write twice a week for the next few months. I will then reapply when I have more work.” I created a Substack named Young Money (only God can tell where this name comes from) and started writing.
August 20, 21
Before I flew to Barcelona, a few weeks ago, I noticed that the popular meme site “Litquidity”, had a newsletter called Exec Sum. It had about 100,000 readers.
I can sense opportunity!
I sent a message to Litquidity via Twitter saying, “I like your content and newsletter.” I’d like to be involved with Exec sum. Please let me know if interested. If you’re interested, I have a blog on finance called “Young Money”.
November 20,21
I was hired by Litquidity and became his editor (?) This is a position I hold today. This gig taught me how the newsletter business works and that you can make lots of cash if you have an engaged audience.
Then I thought, “Maybe a blog is not the best way to find a job.” This blog could become the job.
All I needed was an audience of thousands, right?
December 20, 21
Students in the deferred-enrollment cohort were required to have between 2-5 years relevant experience prior to an MBA. We had to notify Columbia about our experience at the time we submitted our intent to matriculate.
My 18-month work experience was a result of my extra football semester in 2019, and my decision to leave my job to travel in August. While hostel-hopping in Europe, writing a blog, and working on a finance-themed newsletter was not exactly “relevant experience before an MBA”, it wasn’t bad either.
When I submitted my application, I was about 6 months short of the 2-5 years relevant experience requirement. (depending on how you define relevant experience). Two weeks later, I wasn’t thinking about it until I got a call from a recruiter in Sevilla.
*ring ring*
” Is that Jack Raines?”
“Yes?”
” I am ______ from Columbia Business School. We had concerns about your …. experiences.
The 45-minute conversation consisted of Columbia telling me I needed to have more “relevant” experience and me saying what I was doing was more “relevant” than staring at a spreadsheet and clicking my mouse so I could appear online, as I had been doing for the past 18 months.
Let’s face it, everyone who works remotely is doing the same thing.
Columbia told me that I would need another year’s worth of “relevant” experience before I could begin my MBA program. However, they were open to hearing my request to send an email outlining why and how my current situation is relevant to my MBA and post-MBA plans.
Since business school was an important part of my plan for Fall 2022 and I’d made $0 by writing up to this point, I really really had to start at Columbia that fall.
The email that I sent to CBS Admissions was without doubt the best 2500 words I’ve ever written. The result:
It worked. I want to thank the admissions panel for re-examining my application.
May 20, 22
In December I returned to the States after spending a year in Europe. Then, for a couple of months, I went to Argentina. Young Money was big enough to generate revenue from ads and Litquidity’s business was also going well. I’d sorta, sorta turned a blogging into a business.
Through my blog, I not only gained more readers but also built a network with writers, operators and investors.
Traveling was still a great experience. Exploring Europe, South America. Visited friends in Austin from DC. This thought crept into my head: ” Is business school even necessary??”
Yeah, I was already in. The initial plan was to travel for a whole year, get my MBA and then work in consulting, IB, or whatever. I no longer wanted to work in consulting or investment banking. I wanted to keep writing, and continue to do so. I knew how to earn money by writing.
I could work from an Airbnb in Amsterdam, a hostel or beach shack on the Australian coast, or a beachside shack near Australia. Was it really my intention to stay in one place for two years?
It was the best decision for me, both professionally and personally. A Columbia MBA would give me more credibility with those who aren’t as tech-savvy. Business school would also provide me with a group of friends of people my age, doing interesting things. It was obvious to me that I would move to New York, but it was close to saying ” Screw it“.
After weighing all my options over a period of a month, I chose to return to school.
October 20, 2022
This brings us up to the present, when I met my favorite author in New York City.
You might be wondering ” What was the point of that ridiculously long monologue on the last two years in your life??”
This illustrates a concept that is often overlooked: Had things gone differently over the past two years, this meeting would not have happened.
If I never applied to business school or if Booth accepts me, or I am rejected by Columbia, or Columbia does not let me matriculate in the fall, or I decide that I do not need business school I will not move to New York. Morgan will not meet me if I do not move to New York in the fall.
If Covid doesn’t happen, I don’t work remote. If I don’t work remote, I don’t start trading stocks. If I do not start trading stocks, then I will not start writing about stock. If I do not start writing about stock, I will not apply for writing positions. If I am hired for a job as a writer, I do not have a blog. Litquidity will never contact me if I do not have a blog. If I do not connect with Litquidity I will not double down on my blog. If I do not double down on my blog, I will never meet Morgan.
Looking back at the past, we can see the path that led to our present reality. From where we started to where we are now, we can trace our steps easily.
We rarely consider the possible worlds, simply because we cannot see them. Our reality of what happened doesn’t exist in isolation. They weren’t predetermined. The things that didn’t occur played a major role in shaping what did.
If you change one thing from the past, the present will be unrecognizable.
In alternate realities, I could be in business school in Chicago or with friends in Charleston, Austin, DC, or even writing a blog in a hostel in Thailand. In a different reality, this blog would never have happened. I’m currently preparing for IB and consultancy interviews in New York.
This is true for much more than just two writers having coffee on a Tuesday morning in Manhattan.
Apple’s stock dropped 82% between the peak of Dot Com and December 2000. It went from $1.20 split-adjusted to $0.21. Apple has risen more than 100 times from its Dot Com high, and about 600x since its low.
Apple’s performance is often used by investors to illustrate the importance of a long-term approach.
You have to accept the setbacks in order to reap the rewards. “
What if something seemingly insignificant, like a decision or an action, went differently? What if Apple didn’t release its iPod in 2001 or iPhone in 2007 as planned? It’s possible that the company will never recover, or may even go bankrupt during the Great Financial Crisis.
Go back 10 years. What if Steve Jobs had never returned in the 1990s? Or what if Microsoft hadn’t invested $150M into a cash-poor Apple in order to quell government anti-trust whispers? Apple doesn’t exist today.
Amazon was another company that suffered a severe decline following the Dot Com Crash before recovering to become one the most valuable companies in the world. The Ecommerce giant exists only because it raised $672M of convertible bonds just weeks before the crash. Amazon would have been insolvent if they had waited just a month. Jeff Bezos might be working at a hedge-fund in 2022.
Each success story is the sum total of all those things that never happened. Avoiding an infinite number realities that could have led to failure.
Stock picking is difficult because you’re betting on variables that are yet to be realized. You have to predict future events, decisions, and innovations that are yet to come.
Now, it’s easy to think “Of course Should I have invested in Apple twenty years ago?“, but 20 years ago this was not the case.
In 2000, it was impossible to predict that the iPod and iPhone would exist, much less revolutionize the world. Amazon Web Services, Prime and Ecommerce were still based on physical books. Do you want to invest your money in a dying company and an online book store in 2000, when the tech industry was in turmoil? Did you really want to put all your chips into *that* basket in 2000?
