Journal Entries: May 2025

Pivoting to an investment newsletter, deep dive on $THRY, exploring franchising, and the e-commerce pause

Note: this is a longer collection so I have inserted topic headers for each entry so you know what might be of interest

I am currently in a liminal period between my previous job as an analyst at a long-only fund, and whatever comes next (looking more and more like a newsletter). I tweet ~daily stream-of-consciousness reflections about my work and thoughts and then aggregate them here weekly. This helps clarify my thinking and documents my process, while hopefully sparking discussions with others. Sign up to follow along, and feel free to reach out to discuss anything of interest.

4/29/25

Topic: Networking, sleep schedule, deep work, flexibility

My brain is mush. I have many emails to go through and tasks to do. I need to get back to scheduling networking calls, the volume is too low. I need to keep reaching out. Keep learning. Keep narrowing it down. I had a call with a buyside recruiter today. I don’t know where I am at with that. There is some interesting stuff out there, though.

My sleep schedule is shifting much later. Call it 2am-10am. I do not want to give this up. I feel much better and more well rested. And the 10pm-2am deep work block is unrivaled. No one is going to schedule a call over this. I can count on it being there. There are no distractions, there is nothing else going on. I couldn’t do much else even if I wanted to. Why work in the middle of the day when so much else is going on? My prior schedule was greatly restricted and inefficient. It has been weird how slow I have been to realize and take full advantage of this flexibility. Oh, I can now go to that thing that happens on a weekday at 2pm? Didn’t even consider it.

4/30/25

Topic: Freelancing, budget analysis, job search timeline

If anyone has freelancing experience, please reach out.

I did some budget analysis. Assume job search takes 3 months. Depending on how frugal and lucky I am, I probably have to start looking somewhere between mid-July at the earliest and September at the latest. Let’s say mid-July. Not really a ton of time to figure something out. May start looking into freelancing as a way to extend runway.

5/2/25

Topic: Career paths (ETA, ecom, W2), focus, networking

Thinking more about timeline, focus, etc.

Pick entrepreneurial path by ~late May. Kick off traditional job search by ~mid-July. Gives me a month a half to get the ball rolling on whatever I end up choosing. I think that’s still a heck of a lot better than having to do it on nights and weekends (especially in those real early stages). So e.g. if I end up choosing ETA, that’s time spent learning the ins and outs of how deals work, building relationships with SMB owners, lenders, brokers, loan brokers, getting reps looking at deals, etc. If I choose ecom, that’s maybe a rep or two of iterating on a product to try to see if there is demand for it. I don’t really know where freelancing fits into all this. I don’t even know where I would start with something like that. I am also not sure if freelancing would be that much better vs the higher-quality end of W2s out there (remote, asynch hours, good W/L balance to allow for side projects, etc.). Kind of thinking if there is some kind of W2 role out that could align well with whatever I end up choosing. E.g. becoming a business broker is something that seems interesting, but not sure any of those roles have sufficient salary given it takes time to close the first deal to get commission. Also just considering unrelated things that seem like they’d afford me sufficient work/life balance to work on other stuff. Avery Smith Data Analytics Accelerator is an interesting community. Might go that route to bridge the gap. Maybe investing if it was a really, really good fit. That would hopefully be good for the capital angle, but probably not for the work-life/side project angle. Maybe sales just to learn the skillset. Digital advertising space is interesting (e.g. Adswerve internship for career switchers). This all still feels extremely blurry but is maybe starting to come together a bit more? I feel it moving in that direction, at least.

I miss focus. I miss it a lot. It is anxiety inducing and just emotionally difficult for me to be spread as thin as I am right now. Keeping an open mind is hard. Taking action and making progress is what seems to alleviate anxiety but this is just a stage where things move slow due to lack of focus. But I think it is the right decision, for a period of time. To learn a lot, do more networking than I otherwise would, try a couple different things. I still want to try some data analyst/engineering stuff. Ecom. ETA. Investing? Writing? Freelancing? I think the last week or two my networking volume has died down a bit which probably isn’t good at this stage. Need to reach out to more people about the areas of interest.

5/3/25

Topic: LinkedIn strategy, online presence

I want to start using LinkedIn like I use Twitter but it feels unnatural. Will try to start taking small steps to flex the muscle. May dox on here soon too.

5/5/25

Topic: Entrepreneurship mindset, W2, SMB acquisition, ETA

Been sitting with some tension around letting go of the idea of being my own boss. At least in the near term. Or maybe just being okay with the possibility that it’s not the next step.

When I left my job, a lot of people reached out to congratulate me. Felt like a bold move toward entrepreneurship. I felt that too. So there’s been some hesitancy about going back into the workforce. Like I’d be letting people down. That was more yesterday’s struggle though. Feels lighter today.

Now it’s more logistical. Trying to build a bridge to where I want to go. Need to immerse in the SMB acquisition space. Get to know the people. Understand how long it really takes to get a deal done, what kind of capital is needed, and what to do in the meantime. Had a call about a remote role that could overlap with ETA—seems like there’s some potential there.

Wasn’t as productive today as I wanted to be. Have to be up early tomorrow for a meeting with a business broker, so calling it early tonight.

Also—still not sure if these Fiverr vector images are usable. They look pretty grainy. Waiting to hear back from suppliers.

5/11/25

Topic: ETA challenges, franchising, ecommerce, W2 options, LinkedIn

I haven’t written one of these in a week, as I do not know what to write. But I figure something is better than nothing, even if it lacks any kind of conclusiveness or organization.

I still feel pretty all over the place but will give a couple updates on a couple fronts.

ETA seems kind of out of reach right now. Maybe something lower cost (e.g. franchising a landscaping company) is more realistic. But the feedback I have received from various ecosystem participants leads me to believe that it’s highly uncertain whether I can get approved for a loan of any significant size. Feedback ranges from a polite “there’s no way, unless you can get a minority investor to PG and good luck with that” to “I have seen people in your shoes get a deal done before but it really depends on the details of the deal, it would help if [e.g. you had experience you don’t have, or other non-applicable/vague stuff.” I appreciate these people being honest with me, even though it’s hard to tell who just doesn’t want to help you or even have the conversation, and who does but is giving an honest assessment of your situation. Either way, it doesn’t seem like a fantastic way to spend most of my time right now. I’ll likely continue to build relationships and knowledge in the space out of long-term interest, but I don’t think it’s that pressing to really immerse myself in it right now. Still exploring lower cost options like franchising, and may continue to look at some deals here and there and maybe try to get further feedback. I am not sure.

Freelancing I still don’t even know where to start.

Ecommerce has been slow, I should have been more on top of that last week but kind of let it slip through the cracks. Next step is to do a sample order of ten units and try to sell them. Need to decide on supplier, platform, creative, etc.

Still trying to accept the possibility/likely reality of having to go back to W2 work in the near-term. Looking into e.g. a digital advertising internship, remote data analyst roles, etc. Part of me just thinks - I could just go all in on this data analyst stuff and focus on networking and skill development in that space and probably be in a very comfortable spot before too long. And just hang out there and build savings for a bit. But that might feel a bit like complacency. Idk still figuring out where this all fits.

I updated my LinkedIn profile but still find myself reluctant to post on there. Need to figure something out. Maybe start simple, just posting e.g. link to an interesting podcast and a few notes or something. Maybe there doesn’t have to be a big announcement post.

5/12/25

Topic: Franchising (Grounds Guys), partnership, LinkedIn

Several calls and webinars today. I am thinking about franchising as a near-medium term goal. It seems within reach for me financially, and while still higher risk than buying an existing business, not as high risk as some unproven startup.

I am wondering if I should partner with someone for it. So I can move ahead with it now rather than later, after I have saved more. The structure of this would probably look something like - they put $x up ($200k?). That pays for the startup costs. They get 40%. I get 60%. They are passive and I run the business, including a small salary of maybe $60-70k to start. Their cash infusion is treated like a loan - any net income goes to them until they recoup the $200k. After that, we split the profits 60/40. Or maybe they only do $100k and we do SBA for the rest. I don’t know, something along these lines. This is sort of a bet on me as much as anything else. Would need to be aligned about how we want to run the biz. And what kind of biz. Please reach out if you have any thoughts about this or have ever seen anything similar.

I’ve been looking at Grounds Guys, a landscaping franchise. I had one person who is an expert in the franchise space recommend against it. He said if I was doing something like landscaping, I’d be better off just starting my own. And that the franchise doesn’t add enough value for something like this where it is such a low barrier to entry, super fragmented, etc. I am not sure I agree with this. Their NPS is apparently 83. That is insane. Very professional. Clean trucks. Good equipment. Uniformed, professional crew. Post-visit report through a portal. Etc. They have a proven playbook. You get a territory and then they kick things off by reaching out to customers of the several other home services brands that Neighborly owns within the territory. They connect you with other franchisees, with a franchise business coach, they offer a whole backend support infrastructure for marketing, ads, answering calls, hiring, etc. Huge discounts/rebates from vendors. I’d need to verify this with employees but they said the problem is more hiring and retaining talent to be able to meet the amount of work that will be coming to you. To me, it seems interesting.

Was also told by this expert that it is best to have $100k post-close liquidity (Grounds Guys only requires $30k). And that with a small business like that, you do not want to try to do it part-time. The Neighborly guy gave me one example of a guy that needed to keep his FT job for a bit to qualify for the loan so he was working on the biz maybe 20h a week as it scaled up and was paying a GM to handle the rest and make sure it all ran smoothly. I don’t know. Both of these things (starting with low post-close liquidity and part-time) are definitely not ideal. So in principle, I think I agree with these points in a way that I don’t as much agree with the point on the business itself. But - maybe this is the risk I need to take? Of course it would be more comfortable to wait to be in a position where that doesn’t need to happen. But I do have a sense that time is passing me by. I want to start the process of wealth accumulation sooner rather than later and don’t have a sense for how to achieve this effectively (and in a way that is fulfilling) outside business ownership. And then the other alternative - bringing on an investor - is possibly an attractive option, but I 1) would be giving up some degree of control, to some extent, though it depends on the partner and how hands on they would need to be and how much desire for control they have, and 2) wouldn’t really even know how to find the right person for something like this. It may be of interest to someone with capital and experience but who doesn’t have the time to operate the business, but it’s still ultimately a big bet on me.

So - I don’t know. Still figuring it out and weighing options.

I finally posted on LinkedIn. Just some notes from an SBA webinar. It is sitting at 3 likes on 624 impressions. Safe to say I have a long way to go. Need to start posting regularly, commenting on other people’s stuff, etc.

5/13/25

Topic: Ecommerce (yoga mats), supplier selection, action vs. anxiety

Yoga mats- After evaluating ~12-15 suppliers, I have narrowed it down to four. Priced out ten unit sample order for each of them. Two are ~$400 total, the other two are ~$800 total. No idea how to approach this. Leaning toward cheaper ones. But maybe I should actually choose based on production order MOQ/unit cost? Idk. Alibaba apparently has pretty good buyer assurances (I feel funny even writing that) but I am not sure what exactly that means. Like, if it’s just a low quality print or material, do I get my money back? I don’t really know how any of this works. They have some verifications and other seller badges/stats. Maybe those give some comfort.

Need to pull the trigger soon and just keep it moving. Will learn along the way. A recurring theme with this has been that forward action feels good and alleviates anxiety. Bezos says that stress comes from inaction over things you can control. That never made sense to me within the context of public equities, but it is starting to make more sense now. Not exactly sure why it didn’t seem to apply in public equities. Long feedback loops, I guess?

5/15/25

Topic: Travel, light workload

Visiting a friend in Point Venture, TX. About an hour west of Austin.

Workload is limited.

5/23/25

Topic: Investment newsletter decision, $THRY analysis

I am pretty sure I am going to do an investment newsletter as my next step, for reasons I will probably elaborate on at some point. I will also expand on my vision for it.

Worked on THRY today. It was my first deep work block devoted to a stock in a little while. Felt good. Probably too hard pile, though.

5/24/25

Topic: Newsletter strategy, podcasting, $THRY, AI writing

More thinking about the newsletter. Increasingly convicted this is the path for the near term. Excited to talk with several other newsletter authors in the coming weeks. Also kind of want to do a podcast. Need to post more on LinkedIn. Dox myself here. I think the newsletter will be less pitch-oriented and just an unbiased presentation of facts, logic, and thought processes on whatever stock I am interested in at the moment. And then maybe additional info in the appendix that gives me a closer look at my process. E.g. more rambling thoughts about investing lessons in general that apply, next steps, list of interesting potential excerpts, question list, etc. Hopefully helpful for professionals while also providing educational value to aspiring investors and/or retail investors.

Writing with AI is kind of weird/challenging. It feels clunky, like vibe coding. Lots of “no, that’s not quite right, do it this way.” And then sometimes it makes it worse and you circle back to a previous iteration.

Another deep work block on THRY today. I started listening to Cliff Sosin on the Invest Like the Best podcast and I like the idea of contained vs uncontained businesses. I think THRY seems too hard because it seems uncontained. SaaS biz has wide range of outcomes and tough to get comfort around probability distribution of those outcomes.

I liked listening to the podcast. I’m probably only 20-30m in, though. I have been thinking of more kinds of writing I can do. Sometimes when I am listening to a podcast I write notes in the iPhone notes app. Just riffing. What if I published those?

5/25/25

Topic: Fear & faith, newsletter launch, $THRY, ecommerce paralysis

I feel a great deal of fear. I am afraid I am going to launch and get no sign-ups. I spoke with some friends at church about fear today. “Do not be afraid”, or some variation thereof, appears in the Bible 365 times. It is the most common command in Scripture. So is fear a sin? I do not think feeling fear is sin. Fear is a human emotion. But it can also serve as an indication that we have a wrong belief or mindset. Right belief always trusts God. It is not my newsletter plan that will save me or provide for me. It is Jesus. I think fear crosses into sin when we let it determine our actions. So I will keep writing and prepare for the launch. Probably around June 2nd or thereabouts.

I am going to San Diego for a bit next week. Let me know if you are in the area.

I finished the THRY writeup today. Probably final edits tomorrow. It’s my first real writeup on a stock in a while. Rusty! But glad to get the wheels turning.

I have major analysis paralysis on the yoga mat sample order. What a disaster. Frozen in place. I must carve out the time and do something, anything.

5/26/25

Topic: THRY, newsletter focus, pausing ecommerce

Completed final edits on $THRY. It is good to go. Waiting to get this domain name issue sorted out.

I am thinking I may put a pin in e-commerce for at least a couple of months. If I have any shot at having this newsletter sustain me sooner rather than later, I think I need to be 100% focused. It is scary and uncomfortable to commit to something like that, but I am thinking it is necessary.

5/27/25

Topic: $EXPE, podcasting, LinkedIn, time management

Doing an earnings update on $EXPE. Reach out if you’re following! (Been in the space a couple years). Might release it free ahead of newsletter.

Also, anyone want to do a practice podcast? Short run, maybe we release it? I ask Qs, you look smart. Good deal, yeah?

This, and LinkedIn, are things I need more reps on – stuff that's uncomfortable.

Need to be more specific w/ timeblocks to get everything done. Not ideal doing them (or these work journals) last thing. Wonder if I should move those to the front of the day. Probably get more views on these, too.