Journal Entries: June 2025

Stream-of-consciousness writing about what's going on in my life

Going forward, I plan on shifting these journal entries to a weekly cadence instead of daily. Hopefully they come off as more coherent and thorough.

I’ll also be publishing research every other week. Next up is META on 7/7.

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The daily-to-monthly switch was made starting on 6/19, so feel free to skip to there to see the more thorough/organized updates.

Feedback is welcome is you happen to prefer one style or the other.

5/28/25

Worked more on Expedia. Did some networking stuff. Need to consider Beehiiv instead of Substack for newsletter. Anyone have thoughts on that? Also want to forecast my estimated probabilities of success and of certain milestones, events, etc. That is one thing I regret not doing more of in the past when I try new things (e.g. start a new job or something). Will probably write more about that at some point.

5/29/25.

There is still much to be figured out on the newsletter. Trying to set appropriate expectations for myself. Why am I doing this? What do I hope to get out of it? What do I expect to get out of it? What are my chances of monetary success? What can I do to increase them? What do I lose by doing that and is it worth it? What forms of success other than monetary could be in store?

Grateful for how many people have been willing to help and offer advice.

Considering doing regular Twitter Spaces. I NEED to exercise this podcast muscle. Fear. Anyone want to record something? I ought to reach out to people and just do it. Some have already offered. What am I waiting for? I know I need to do it, if for no other reason than I sort of want to and I feel fear standing in the way.

5/30/25

Major FOMO about ecommerce stuff. I really think the newsletter stuff requires 100% focus but I cannot seem to shake the idea that ecommerce has a better chance of making money. I have now spoken to several different people who run newsletters, and while advice is sort of all over the place, I think the one common thread is that the market is very saturated and it is going to be very difficult to scale, especially within a couple of months. This makes me wonder if it’s the right thing to focus on in such a single-minded manner.

I am not sure what I can do to differentiate. What I really want to do is work on the names that interest me. If I stuck to e.g. just working on alts ($KKR $APO $BX $CG $BUR etc.), maybe that would get more attention. But do I really want to do that? Would I enjoy that? I also wonder if there is just some other, maybe broader product to pursue. E.g. maybe I focus on the podcast/Spaces itself as the product that people are paying for, and forget the research or just do it occasionally. I am not sure. It seems like a grind. And then e.g. if I spend two months trying to build it up to no avail and late July comes and need to find work, now what? There are only a few funds I would want to work for. I’d still want to try the ecommerce at some point. And if pivoting industries, I’d need some time for skill development. So whatever I did build up to that point, how could I maintain it amid all of that?

I don’t know. Still exploring the idea and writing to build up the offering in the meantime. THRY and EXPE are done and ready to go. I think a 13F analysis is next.

5/31/25

Vibe coded some 13F stuff today. Did this same project about a year ago and it has gotten much much easier. These models get better and better. I did it with Claude 4 and Gemini 2.5 side by side to see which could get the first working prototype and Gemini 2.5 won. I had really been sleeping on Gemini until about a week ago. I tried it out and it’s now my top choice for most things.

I am unsure how to approach the newsletter in terms of when to make it paid vs launching with some free content. Need to think more about pricing, content, etc. Need to refine expectations and really figure out why I’m doing this and what I can reasonably expect to get out of it across different ways of viewing the payoff. Need to arrive at a realistic timeline. Figure out when and how to dox. Figure out podcast/Spaces. Other ways to add value. Other things worth paying for. Summarily, just need to make a plan and stick to it. I think I’ll probably post some kind of content this week.

One thing that I think helped a bit with the Ecommerce FOMO was I heard a Tim Ferriss quote where he basically said - what would you do if you knew it was going to fail? We will define fail as not reaching a point of sustainable income before I need to start job searching. And I think my answer is pretty clearly the newsletter (or broader investment media effort, whatever it ends up looking like).

6/1/25

I want to interview people - podcasts, Spaces, written, whatever. Probably my favorite part of being an allocator was grilling smart managers on their biggest positions.

Single-stock ideas are great. Also open to business, careers, whatever’s interesting. Anon or not. I’ll start doing outbound soon, but also open to inbound - DM me.

Spent most of the day rewriting my 13F analysis script to pull directly from EDGAR instead of an API provider.

6/2/25

Caught up on $CCOI today.

Need to publish articles. $THRY $EXPE ready to go. Need to figure out action plan for how to go about this next couple days. I may be overthinking it and just tweet it out. Maybe I do a larger announce later? IDK TBD.

6/8/25

I am thinking about making the newsletter focused on alts (CG KKR etc.). I am also considering just keeping it free until I get to a certain free sub count. I will need to find a new job soon.

6/9/25

Released the THRY writeup. Very few views, no new subs. Not sure what I am doing but it is good to have gotten it out there. Will keep writing.

6/10/25

How do y’all manage and prioritize your obligations across life?

I have spent several hours over the course of the last two days getting to inbox zero (at least for one email address) and putting tasks into a board on Trello. I still have ~60 starred emails I need to go through, though. Board consists of labels that, so far, include Personal Tasks, Investing, and Content Ideas. This will likely be added to. Also created email folders which include, so far, Historical Archive (everything basically gets dealt with or moved here to achieve inbox zero), Content (for consumption), E-commerce, SBA/Franchising/ETA, Other Entrepreneurship Ideas, Personal Notes, W2s, and a couple others.

Historically I’ve mostly managed this via a Word document (or sometimes Excel/Sheets) and then just letting my emails kind of be whatever. Trying something new to see if it helps at all. Not sure what will come out of this, but hoping it results in greater focus by forcing me to prioritize and deal with things. Also want to use the system rather than it using me, though. We will see how it all goes.

6/19/25

Topics: this journaling practice, where to live, W2 (what and when), and the newsletter.

This Journaling Practice

Been slacking on these journals so I figured I should write one just for a high level update. I may shift to doing these on a weekly basis rather than daily, but try to put a little more time into them. Lots of times it’s the end of the night when I do these and I don’t have energy to do much more than a sentence or two, and I am not sure how valuable that is to me or anyone else. I also think ~4-5 larger and somewhat more coherent posts per month make for a better aggregated read than 30 smaller ones.

Location

I do not know where I want to live. I am evaluating a couple options. I currently live just outside Phoenix, AZ. I like it here. Warm weather is a must. I’ve built up a pretty decent community/support system. I am evaluating other options, though. The main one is probably Austin (either the city or Point Venture on Lake Travis). My friend just bought a house by Lake Travis and has offered to let me stay there for a pretty affordable price while I figure things out for a while. Being outside of a city was kind of cool, and the lake is beautiful. It would be good to live with a friend, but I also have really enjoyed living alone and having space to myself so it is a bit of a tradeoff. I grew up in MA and could move back there, but don’t really want to due to the winter. As a side note - I recently found out that at AltaRock, apparently the whole firm snowbirds down to Florida from Boston during the winter. Talk about a dream job, as if working there didn’t already seem good enough. My parents also just built a house in Florida, but it’s more or less in the middle of nowhere. I haven’t been there yet. I wonder if I could stay there for a little while. My aunt and uncle and a couple of other family friends are right next to them, too.

W2 - What

I’m going to have to go back to work soon-ish. I am not too sure what I want to do. I am open to contract work as well. I am very open to trying new things if the fit seems right and I am evaluating several options. It makes for an easier narrative when it’s like “I am just set on career path xyz” but I don’t want to be dishonest. I am interested in lots of different potential paths - public equities, data analyst, sales, PE/VC, content creation, ETA adjacent roles, and more. Part of me wants to make sure I stick to some basic requirements as far as the structure of the job goes - e.g. I’d really like to be remote. However, it’s tough to tell when the tradeoff might be worth it. E.g. If I can work for Warren Buffett but I need to move to Omaha, then you can catch me at Nebraska Furniture Mart next week. But how many jobs are worth sacrificing something as important as where you live and where you spend your day to day at? I am not sure.

Data analyst seems like an interesting path with good career options. I am considering spending some more time on developing the necessary skills. I already purchased Avery Smith’s Data Analytics Accelerator and that has been sitting unused for a while. That focuses on Excel, SQL, and Tableau from a skills perspective but also has a big emphasis on networking and developing a portfolio of projects. Zach Wilson has a six week data engineering course that looks interesting, too, but is definitely a step up in terms of skill development.

Public equities is public equities. I don’t think I’ll ever be able to fully go away. I love it. It will always play some role in my life. But is it the right industry to work in? It seems like such a small percentage of the seats in the industry are worth considering, for a variety of reasons. I think it is sort of a dying industry that is becoming increasingly difficult to perform in and to raise capital in. It’s kind of strange because we spend all of our time analyzing businesses and industries and trying to decide which ones are “good” or have a bright future. And it’s hard to then apply that same mindset to your own career. But nevertheless, if I do think that someone has it figured out on both the investment side and the business side, then it may be worth evaluating whether it is a strong fit in terms of personality, how the work is done, location and working style, etc. So I am still keeping my eye out, and also open to contract work here as well.

Sales is good fuel for my competitive spirit, plus being excellent in terms of skill and character development.

There are a few areas that are still of entrepreneurial interest to me (ETA, franchising, ecommerce, etc.) and I’d be open to those.

Content creation has always been something on my radar. E.g. I think there was a Capital Allocators Head of Content role that seemed interesting, but maybe too administrative-heavy for me. There was a role at Tikr I saw. These sorts of things seem to pop up now and again.

Along the lines of sales and content creation, there are also a lot of e.g. AI startups out there focused on equity research. I think I have a good background and network for some of those. Or even something like Tegus/AlphaSense. I think working at a startup like that where I really understand and am passionate about the product, industry, customers, etc. would be cool.

PE/VC I’d be open to if something really unique came along. Sort of similar situation to public equities.

W2 - When

I could start applying now, or I could start applying in late July. I don’t know when. I feel pressure to start sooner rather than later, but I am honestly not sure if that is my own drive or if that is just me worrying what other people think. I want to practice the skill of trusting God and being comfortable in challenging situations. And burning cash is certainly not a naturally comfortable situation! So, yes, I do think some of this drive to get moving comes from within. But there’s also definitely an element of fear. Around having a resume gap. Around the awkward conversation when people ask me how the job search is going. Etc. But deep down, my intuition is that everything is going to be fine as long as I stay close to God. And my “fine” doesn’t necessarily match society’s “fine”. It’s just to say that - when you talk to people about this stuff, even though they don’t say it directly, there is an underlying tone of the “the sky is falling, you are crazy, you need to do something now or things are going to end up very, very bad for you”. And I just don’t think that is useful or true. If God wants me to go work some manual labor job to pay the bills for some period of time, I am not afraid to that. But I don’t think I am going to end up homeless or hungry or anything like that. But for a lot of people, going from public equities to manual labor is the social/emotional equivalent of going homeless or hungry. Still trying to make sense of all this and decide the best path forward.

Newsletter

This is clearly a long-haul type project. The subscribers are trickling in but it is slow. I have requested two podcasts guests so far and both basically said yes but that they are busy and to reach out in a couple weeks. I am excited for that. I have published on THRY and EXPE and have a 13F analysis in the works that will probably go out Monday. While the trickle of subscribers has been somewhat discouraging, the quality of some of the subscribers shows I am on the right path and that my content clears a certain quality bar to get these people to sign up. E.g. it was cool to see the founder/PM of one of the funds on my 13F list, who I have never spoken to, sign up. But right now - I am just focused on getting the work out. I am sort of doxing myself in some ways, e.g. I posted a link on my LinkedIn. But the formal “big reveal”/call to action on here and more branding/marketing efforts are still TBD on timing. I have around 400 free subscribers right now. If I charge $40 month and assume a 2.5% conversion from free to paid, then it’s probably best for me to turn the paywall on when I get to 4-5k free subscribers. That is a very long road. But I believe I can get there someday if I am consistent and if, over time, I get better at those branding/marketing elements and find what works best for me. E.g. I am excited to try podcasting as a way to grow top of funnel, and I think it is something I could potentially be good at. TikTok or YT videos? Not so much, but if I want to be thorough maybe I end up trying that at some point, too. Maybe AI generated. But I don’t know the quality of subscribers that comes from that either. Lastly - still not sure on what the focus of the newsletter will be in terms of generalist vs some niche. I was surprised at the poll results that suggested much more interest in generalist vs publicly traded alt asset mgrs. But I still have the freedom to e.g. focus primarily on alts for a couple/few months and see how subscribers track with that.

6/29/25

I Am Open To Work

I am starting to look at some different opportunities. I am mainly interested in contract/consulting work, but also open to certain remote roles.

My primary area of expertise, as well as my network, is in public equity investing and so this is where most opportunities seem to be popping up so far. I think there are very few roles within public equity that align with what I am looking for from both a craft/investment philosophy perspective as well as a quality of life (i.e. remote) perspective. And even fewer that would allow me to continue to work on the newsletter and other media. I want to make sure I hold a high bar for myself on each of these fronts. I’d probably rather try something entirely new than repeat previous mistakes (“I don’t like X about this opportunity, or Y seems off, or maybe Z will change over time, but I know I can do the job so we will see how it goes…”) because it’s an industry I am comfortable in.

When it comes to new things to try, there is a lot I am open to. Sales, FP&A/IR, data analytics, content creation, and much more. I am almost less concerned about the descriptive nature of the work itself (i.e. the job description/title) and more concerned about other qualitative factors such as - how much freedom and autonomy does the role provide? If it is lacking, where does it make up for it (e.g. financial upside)? What are the opportunities for character and skill development (sales roles stand out here)? Who are the people I am working with? Do we think about the work similarly? Do we think about life similarly? And so on.

I’ll consider this a sort of soft launch of my search and would appreciate any introductions to people you think might be worth speaking with.

I Still Don’t Know Where I Want To Live

I am in Chandler, AZ. I still can’t believe people choose to live in places where it snows. I am running as far away from the cold as possible.

Besides moving somewhere else in the Phoenix area, the only other real candidate right now is still Austin (either in the city or Point Venture). I’ve built up a lot of connections and support in the Phoenix area that I am really grateful for, and that is one of the main things that makes me wonder whether I even should move. But I have a couple of friends in Austin. Living in the city would probably make it easier to recreate that network, but it’s also fairly expensive. Plus, I have come to like cities less over time. Point Venture has a much more relaxed feel to it, which I think would be good for me at this time in my life. I am trying to change how I think about work, money, and life in general and I think an environment like Point Venture is more conducive to those changes. I’d imagine it’s easy to get caught up in the hedonic treadmill living in the city.

Newsletter

The rough buildup of how I am thinking about this: I could probably go full-time on this if I am able to hit $4k/mo take home pay. That would be $48k a year, or $68,600 pretax. Given processing fees and Substack’s take, I would need $78,900 subscription revenue. That is $6,600 per month. If I charge $360/yr ($30/mo, though the monthly rate would be higher than that to incentivize annual) I need 206 subscribers. Assuming a 2.5% conversion from free to paid, I need 8,240 subscribers. I am only at ~430 right now.

That is a long way to go! I have only written three pieces so far, but they each generate a very small number of subscribers. I might spend 20 hours researching and writing up THRY or EXPE or a 13F analysis, and then only get 10-20 subscribers.

I need to focus on high leverage activities. It’s tough, because I also want to have a library of high quality research built up so that people 1) can immediately get value out of it when they do subscribe after I put up a paywall, and 2) trust the work. But in the sense that free subscribers is sort of my most important metric right now to get me to where I want to go, high-quality research is not really serving me well. I want to try other things like podcasts, written interviews with FinTwit people, etc. I need to figure out some combination of the two - keep generating high quality research on the one hand (at whatever rate/cadence/depth makes most sense), and grow the top of funnel on the other.

I still have a lot to learn here and I am not totally sure if I am thinking of it correctly. E.g. I hear some people say - “don’t focus on your free subscriber count, just focus on the quality of your work. And the quality of your subscribers. And turn the paywall on early.” And - I don’t know which is right. I am looking into Wes Pearce’s course about how to grow on Substack. I feel a little lost right now about how to approach it but I will continue to write and be consistent anyway. Probably one writeup every other week for the foreseeable future. The next one will be META, a week from tomorrow.

There are still dozens of granular details to figure out around - when do I dox? Podcasts or written or Twitter spaces? Do I try short form video? 30m podcasts or regular length? How integrated is this with my marketing/consulting efforts? Is this basically my marketing engine for that? How do I figure out what to charge for that? Is that basically the bottom of the funnel and the paid newsletter sub is actually the middle of the funnel? Who do I ask to recommend me? How? Who do I ask on the pod? How? What other channels do I have available to me? And much, much more. For now - I need to just focus on keeping the momentum going. As long I don’t stop, I think good things will come out of it. It will be a little more ambiguous if I decide to go into something like data analytics or sales full-time. Then there is definitely less overlap/synergy. I wonder if my writing would evolve accordingly.

Miscellaneous Other Ramblings

I face a tremendous amount of uncertainty in my life right now. Where to live. Where to work. What to do for work. Where to apply. When to apply. What consulting opportunities to be open to. How to price them.

It is uncomfortable. I think if I continue down a path of greater freedom, autonomy, and agency - this is the downside of it. I am learning to live with the discomfort. It is mostly spiritual, and trusting God to provide. Not rushing things. I want to rush things. I want clarity now. I want income now. I want status now. I want awkward conversations about what I am doing with my life to end now. I want the cash burn to end now.