Short-Term Thinking | Issue ooo

Hello and welcome to the first issue of Short-Term Thinking! 

First and foremost - thank you. It means so much to me that you signed up for this newsletter before I wrote a single word. Many of you are among the people that I respect the most in our little real estate/STR corner of Twitter (I’m never calling it X) and it has been extremely gratifying to see the signups roll in. You have my sincere gratitude and I hope to provide some value to you in the coming months and years with this newsletter.

The Rundown

1. Who is YoC?

2. Why Create Content?

3. Why a Newsletter?

4. A Sidebar on Distribution and Monetization

5. What You Can Expect From Short-Term Thinking

6. Asks

I. Who is YoC?

I’m not ready to be fully public still, but if you want more background on my experience I’d encourage you to read the interview I did with James Timmons back in February where I go into more depth on my history in the short-term rental space. My background, in short:

• Started my career in equity research, spent almost a decade on the buy-side

• Joined a STR operator as the first full-time employee and helped grow that from 30 apartments under management to ~1000 in 2.5 years

• Burned out

• Now own/operate a small portfolio of luxury short-term rentals, tweet occasionally, and have a whole mess of toddlers running around the house

And as many of you already know, if you send a couple thoughtful messages and we chat on the phone you’ll find out who am I pretty quickly, it’s really not a big secret.

II. Why Create Content?

56 weeks ago I poured my second glass of wine (ok, third - but they were small pours) and started a Twitter account with the intent of actually posting. I’ve had a (private) Twitter account since January 2011 and have been following all the usual suspects on RETwit/SMBTwit from the very beginning without contributing anything. I watched people build businesses, make friends, find clients, and create partnerships for a decade without doing anything myself.

After posting something just about every day for the past year now, it’s hard not to look back at those eleven years lurking with anything but regret. Having now experienced just a taste of the magic that can occur when you put your thoughts out publicly - the relationships, the deals you see, the new friends, the cool experiences - it’s hard not to feel more than a twinge of regret about what might have been, the doors that might have opened and roads I didn’t know to explore.

The best articulation of that experience and what I am trying to accomplish with my posting is Jason Roberts’ concept of “Luck Surface Area”, which I will take the liberty of slightly modifying for our purposes here:

“The amount of serendipity that will occur in your professional life is directly proportional to the degree to which you convey your passion, proficiency, and integrity, combined with the total number of people to whom this is effectively communicated and demonstrated.”

That’s why we’re here, and that’s why I love this particular articulation of the idea - because by its nature serendipity is unpredictable. Even if I don’t know exactly what it will look like and don’t have an end goal in mind, I know that if I keep putting out interesting, thoughtful ideas on a consistent basis that cool things with continue to happen. To someone who is reflexively private like myself the second part of that statement has and will always be the most difficult - after all, I’m still just a dumb handle with a yellow house/star avatar. But the fact of the matter is that if you don’t let people know what you are doing then nobody will ever know.

Which leads us to…

III. Why a Newsletter?

First and foremost I want to write more - I had forgotten how much I enjoy doing it and the benefits that can come from it. I find that when I am forced to put my thoughts down in a clear, concise manner it helps to crystalize & sharpen my thinking. I want to spend more time on projects and put out higher quality work, and Twitter is not the greatest forum for that.

Up until now, my only internet presence has been Twitter. Twitter is many things, but most of all it is an excellent distribution platform, maybe the best that has ever been created for the written word. However, it is such a great distribution platform because it is algorithmically driven, and I want to create work that exists outside of that unforgiving reality. 

Twitter rewards certain behaviors (combativeness, braggadocio, acerbity, etc.) that are in direct opposition to how I want to convey myself and run counter to what I am trying to accomplish. A newsletter is a far better venue to demonstrate my proficiency and integrity - a more permanent and lasting vehicle to discuss an industry I continue to find endlessly fascinating.

Don’t worry (or maybe you should worry about me…), I still plan to be just as active on Twitter both because I (mostly) enjoy doing it, and it is such a great distribution platform. Every day I am getting exposed to new people and new people are finding my work. To put it in simple terms, Twitter is for reach, and Short-Term Thinking is for depth.

IV. A Sidebar on Distribution and Monetization

There are two sides of content creation - distribution (gaining attention) and monetization (utilizing that attention). I’ve spent a lot of time thinking about this after listening to Chris Paik on Invest Like the Best, specifically this passage:

In many ways the first part of the equation (gain attention) is the easiest - create interesting content and produce it regularly. There is so much information out there about how to “grow” on social media and to me that stuff gets boring and gross pretty quickly. Far more interesting to me recently, is what you should do with that audience because the “correct” answer can be wildly different for different people and more often than not the “monetization” is not monetary at all.

At this point, I don’t have anything to promote or sell or any service to offer, so the highest-value way that I can think of to “monetize” the small audience I’ve grown is clear to me: build as many meaningful relationships as possible.

I have already met at least a dozen people through Twitter that I could see being investors, partners, friends, advisors, clients, or mentees. Short-Term Thinking is ideally a place where I want to deepen those relationships, to build up more credibility, to engender more trust. And that’s why it’s important for me to have a creative outlet where the “success” of a post is not virality, but the number of thoughtful responses received. Not retweets, but phone chats and coffees & beers enjoyed together. Not follower count, but the number of investments we have partnered on. 

As you all probably know, this has not the best time to be putting money to work in short-term rentals, or real estate generally. I haven’t made a new investment since April 2021. To use a physics analogy, I have decided to use this fallow period to build up as much potential energy as possible, so that when the market tells us to be buyers I can turn that into more kinetic energy than I otherwise would have have at my disposal.

More than anything my goal is to be the first person you think of when you think of short-term rentals. If you’re thinking about a new market, or bringing in an investor, or looking for an advisor, or want a second set of eyes on your underwriting for a new property - I want you to think of me and be comfortable reaching out.

V. What You Can Expect from Short-Term Thinking

I don’t want to be too prescriptive before sending off a single post so this is all subject to change and evolve. However, as I’ve been thinking about this project I have kept two guiding principles at the forefront:

1. Do Good Work: You can expect high-quality, original work. Think my most thoughtful Twitter content, but with more time spent on it. I’m also looking forward to doing interviews with people I respect and admire, spending more time with STR data, sharing my underwriting and qualitative market/property analysis in more detail, analysis on companies in the STR space, and more.

2. Attention is Sacred: I want you to know that I deeply value any and all time that you spend reading my thoughts, and I endeavor to always respect that precious resource. On the Internet, there is nothing more valuable than attention. I am planning to put something out every other week, but I want you to know that if I don’t have anything that meets a very high quality bar I am going to default to not putting anything out rather than sending something I think is mediocre. If it’s in your inbox, it’s because I have something to say and I think it’s good, not because I felt the need to stick to a regimented schedule.

VI: My Asks

1. As I said before, I genuinely would love to hear from you. Please know that my inbox is always open and if you email me I promise to get back to you within 24 hours.

2. If you think someone might enjoy a particular issue of STT, please forward it to them!

3. I’m learning on the fly here - if you want to see more (or less of something), please let me know - all feedback (especially critical feedback) is sincerely appreciated!

See you next week for a recap of Q3 earnings season for the hospitality industry!

-YoC