The Power of Writing
A handful of stories about the internet and unexpected investing careers.
Nobody knew Bill.
He was an up-and-coming analyst studying a nascent industry.
Bill had set out to study the internet and the many high-tech companies that, somehow or another, made a profit from this newfangled infrastructure.
In his own words: “It was immediately clear to me that a sell side analyst that was more well known would be more powerful.”
Bill needed to get his name out. But how?
A weekly fax would do the trick (we’re in the 1990’s in case you can’t tell). How about a newsletter that would cover his ideas on this evolving industry?
So, Bill pumped his colleagues for contacts. This worked, but only a little bit. He needed to get in front of more eyeballs.
As luck would have it, Bill’s old boss got him into a tech conference out in Phoenix. This was Stewart Alsop’s Agenda conference.
PalmPilots were being sold in the lobby. To entice buyers, each attendee of the conference had his or her contact information preloaded into the device.
For $200, Bill got access to Larry Ellison, Bill Gates and several hundred other tech leaders.
He began spamming them with his newsletter.
And it grew.
That’s how Above the Crowd was born. Bill Gurley would go on to join Benchmark, where his writings led him to all kinds of interesting connections… and investments.
Uber, OpenTable, Zillow, Nextdoor, Grubhub and many more.
But Bill isn’t the only investor who’s career was jumpstarted by a blog.
Money Managers
Dave Waters grew up in a town with no stop lights.
He had zero connections and knew nothing about investing.
Back in 2012, Dave started a weird blog about weird companies.
He covered things like the Los Angeles Athletic Club, which went up 5x in the five years after his writing.
There was Maxus Realty Trust - a weird collection of commercial properties and multifamily housing in Kansas City. This stock went up 10x in the 8 years after his writing, before selling off assets and returning capital to shareholders.
There was Monarch Cement - a 100 year old cement business in Kansas. That one is up 4x since Dave wrote about it in 2019.
Anyway, you get the picture. These were small, sleepy companies.
One day, about a year after Dave started his blog, a reader contacted him asking if he might like to manage some money.
Then another reader did the same.
It’s hard to imagine a less scalable strategy. Who was going to give money to a random guy on the internet to buy pieces of far flung businesses?
Dave is managing $80MM+ today. He’s smashed his benchmarks since starting the fund.
Turns out the internet is a big place.
Check out Dave’s writings here: Alluvial Capital Substack
John Huber started writing a blog in 2012.
He’d made a piddly sum of money from real estate and decided to commit to the craft he loved - public market investing.
He told me the blog started as a way to connect with other investors. He just wanted to learn.
His writings started to get traction, and again, people contacted him to see if he might like to manage their money.
John started with $2mm under management in 2013. He now manages ~$120mm.
John says almost every dollar he raised came from his writings.
Last year he gave a talk to students at NC State University. His number one piece of advice for the students was to go out and write publicly on a topic they’re passionate about.
“It’s a free call option”, he says.
You can read John’s blog here: Base Hit Investing
There were a couple of really good podcast episodes from Dave and John on The Business Brew with Bill Brewster. You should check them out:
Dave Waters on The Business Brew
John Huber on The Business Brew
Tim Ferriss
Tim Ferriss famously wrote “The 4-Hour Workweek” in 2007.
You almost certainly know the book. But that’s not the interesting part.
Tim parlayed his reputation built from writing into an angel investing career. He was less interested in making money and more interested in earning a real world MBA.
His goal was to spend $100k over a couple years investing and learning - an equivalent sum to what he would’ve spent on business school.
Of course, he did make money - and a whole hell of a lot of it.
He was one of the first three advisors to Uber - helping with marketing strategies.
He was the first advisor to Shopify.
He made early investments in Facebook and Twitter.
While it’s not publicly known, I’d estimate Ferriss made more than $100mm from these investments.
As the angel investing career slowed down, he launched The Tim Ferriss Show. A longform interview podcast.
I’d estimate this podcast earns ~$10mm in annual revenue today.
Here’s a great interview of Tim telling his story:
Other Writing Successes
Of course, it doesn’t have to be a blog or a book. You could write a letter. My buddy Joe Raymond has a cool story:
Joe’s typewriter led him to an evening with Charlie Munger. It has taken him to all kinds of other cool places over the years.
Joe also writes a blog about old companies. It’s been my favorite discovery this year.
Pieter Levels is an indie hacker and solopreneur.
He makes ~$3mm a year from spinning up little projects on his own.
Things like an AI photo editor. A resource for indie hackers to figure out where they may want to work from next. All kinds of little things.
Pieter has an audience of 700k people on Twitter (X).
Recently, Pieter shared that he’s making $10k/month from Twitter (X) payouts.
Of course, this is nothing to him. And he has a huge audience that he can leverage in all kinds of different ways. But still, it’s cool that someone is making 6 figures just from writing their thoughts on the internet.
Putting It All Together
What do all these guys have in common?
They went down a path that was interesting to them and found a way to leverage their thoughts. Largely through the internet.
Personally, writing has opened doors for me that I would’ve never imagined.
I can’t believe some of the people who will read this post. It’s incredible.
There is a monetary aspect to it, sure. I get paid a few bucks from subscribers. More importantly, I get compelling investment ideas sent to me from time to time. I made three investments in the past year which came directly from subscribers.
The internet created the greatest reputational lever our species has ever known.
You do a little bit of good and get tenfold in return.
You do a little bit of bad - at a Coldplay concert, say - and you lose your job.
My advice - do a little bit of good.
Do it where the world can see.
DISCLAIMER: THIS IS NOT INVESTMENT ADVICE. I MAY OWN SECURITIES MENTIONED IN THIS ARTICLE. THIS IS NOT A RECOMENDATION TO BUY THESE STOCKS OR ANY OTHER STOCK. I MAY BUY OR SELL ANY SECURITY AT ANY TIME. I MAY NOT TELL YOU IF AND WHEN I BUY OR SELL. THESE STOCKS ARE ILLIQUID AND YOU SHOULD UNDERSTAND THE IMPLICATIONS OF THAT IF YOU BUY THEM. THIS IS NOT TAX, LEGAL OR FINANCIAL ADVICE. I AM NOT YOUR FIDUCIARY. THIS IS THE INTERNET AND YOU’RE LISTENING TO A GUY NAMED DIRT.



