Business update, week 2
August 4, 2025 at 1:28 PM
Hello! My name is Jake. A few weeks ago, I quit my job with a plan of spending the next 6 months giving a serious go at starting a business. I’ve had vague plans around doing this in the past, but have never attempted it for real, so this is a new thing for me. I think I have the skills to be successful, but there’s certainly a strong chance that I’ll fail.
I intend to use this Substack to document the process, and hopefully provide others like me with a look at how one novice entrepreneur is approaching things. At a minimum, I’ll post once per week with an update on what I worked on the previous week, lessons learned, and goals for the following week. Maybe later on I’ll write about why I want to start a business, or branch out into other topics, but initially my focus will be making one post per week about the nitty-gritty details of what I’ve been trying.
I’m sure the format will evolve significantly over time but for now, my priority (both here and with the business) is to start imperfectly, prioritize action, and improve as I go.
My hope is that writing these progress updates will provide:
- Motivation: I don’t want to write an update that says I didn’t accomplish anything. On the flip side, it will be feel good to write updates where I get to brag about the milestones I hit
- Accountability: Writing my goals on paper and reviewing my results each week will make it harder to fool myself into thinking I’m progressing when I’m not
- Reflection and learning: Writing consolidates knowledge and organizes thoughts
- Track record / history: I imagine it will be neat to look back at prior updates and see where I was at different points in time
First, some brief context on my situation:
I currently have about a 12 month runway of living expenses, assuming I stick to my budget (and that I have no income). In order to avoid disaster, I’ve given myself a couple of checkpoints/guardrails:
- If I don’t reach at least $1000 / month of revenue by the end of the year, I’ll stop and look for a job
- If I drop below 4 months of living expenses remaining, I’ll stop and look for a job
So I have a bit of time, but if I want to hit that first checkpoint, I’ll need to see real progress fairly quickly.
What were my goals this week?
I didn’t have explicit goals set (goal for next week: write down specific goals!) but generally I was trying to start testing some of the ideas I brainstormed last week to see if they were actually good product ideas.
(Side note: this is technically week two for me. The main thing I did last week was make a big spreadsheet of ideas / problems to solve, linked above. The idea was quantity over quality and to start building a habit of identifying problems whose solutions could become products)
What did I accomplish this week?
Built out a concept for a ‘book club matchmaking service’
My vague theory is that lots of people want to join book clubs but don’t want to start one themselves and don’t know people that share their reading interests. Is this true? No idea really. I created a history book club on Bookclubs.com last December, made no attempt to get people to join aside from scheduling and attending meetings, and now 8 months later it has 70 members. Several of them told me something along the lines of “none of my friends care about history and all the other book clubs on Bookclubs.com are just the same pop fiction, this was such a good idea!” So maybe there are lots of people wanting to join book clubs of different varieties, but who don’t have a good way to find each other.
Anyway, I created a landing page, intake survey, and came up with some ideas for how to market the service. Then I convinced myself that this was a terrible idea that nobody would sign up for, so I didn’t actually do anything with it. I’m leaning against pursuing it further - theoretically I think it would work once lots of people were signed up, but its fatal flaw is that it probably needs on the order of 100-200 people to sign up for it to really work at all. So I’m nervous to try and get people to sign up - if only a few do then they won’t get what they paid for.
Cold emailed some auto-repair shops offering to build websites
I made a list of maybe 20 or 30 auto-repair businesses in Arlington and found that many of them had no website at all, or a very outdated one. I emailed several of them offering to send them a free website design concept. These felt like the type of emails that I myself would delete or send to spam if I received them. None of them got replies which I was not surprised by.
Honestly, I didn’t give this a good effort and am not sure I learned much - I do think ‘web design agency’ is not a terrible business but I would need to try harder to see if I could really land any clients, sending a few cold emails is not going to get me anywhere. A better approach would be something like:
- Make a few sample websites for whatever business type I’m targeting
- Make websites for a few places for free, primarily to get testimonials and learn what things they care about in their websites
- Put real effort into coming up with a pitch that could actually convince other businesses of the value of my service
- Try harder to get in touch with a real person from the businesses I’m targeting - call on the phone or show up in person to demo rather than cold emailing
- Any time I manage to talk to any real person, ask if there are any other people they can put me in touch with - then instead of all cold leads I get some lukewarm leads
The business model here would be something like $1000 site build plus $50-100/mo maintenance, raise prices over time as you get a track record, build tools to make the site-building faster, increase marketing, expand to adjacent markets, etc., etc.
Big downside here is that it is easier than ever to build a website so not only can more places do it themselves, more people can also do it for them. So at least for generic types of sites, it's probably pretty hard to get many clients. If I pursue web design, I may be better off trying to sell the more bespoke web-design skills I have and go for higher prices / fewer clients.
Learned about auto-repair shop business models and common pain points
I spent about a day learning about the auto-repair business. My goal was to understand the finances at a high level and what the most common issues shops run into are. Aside from the most common - bad reputation / bad reviews, shortage of skilled technicians, I was able to identify one concrete thing that seems like a solvable issue:
Slow customer consent for new charges - shops can only charge up to a certain amount without a customer’s explicit consent, otherwise they’re liable for any excess charges. After they diagnose an issue, they have to contact the customer and get their consent to proceed before they begin work. If they can’t reach the customer, the car sits in a bay for potentially many hours. These are non billable hours (techs aren’t doing any work in the bay), so this reduces the productivity of that bay.
Some shop-management software has features to help with this - in particular, ability to text customers, share pictures of any issues, and ask for consent to proceed, but lots of shops don’t use this software or don’t effectively use that specific feature. Seems like there should be ways to speed up this process.
That said I’m still mostly guessing here because I don’t know any shop owners or have an obvious way to talk to one about whether this is actually a big issue.
Researched personal chef businesses
I saw a post on Reddit (r/nova) where someone was looking for a person to do meal prep for their family once per week, at their home. This led to me reading about “personal chefs” - this is a business where someone shows up to your house once per week for maybe 3-4 hours, cooks you meals for the week, and then cleans everything up and leaves. A typical rate would be $350 / visit + cost of groceries.
Some nice things about this business - almost no startup costs (just cooking equipment and basic insurance, plus ability to cook and plan effectively) and no commercial kitchen shenanigans because cooking is done in the client’s home. Each client gives recurring revenue, typically weekly. 5 clients at $350 / week is $7k / month, for maybe 25 hours of work.
The big downside is that it seems like a hard business to grow to a large scale - you can hire more cooks, but labor cost still scales with # of clients. So to grow it you need to expand to private events, get commercial kitchen access, do lower cost / higher volume meal kit delivery, other things like that. I also don’t see a ton of opportunities to use my tech/software skills to add efficiency, although I haven’t spent a ton of time brainstorming on that. All in all though it’s an interesting idea and one I’ll keep in mind.
Tennis partner matching?
Didn’t research this but I saw multiple people on r/nova looking for tennis partners in the 2 days I’ve been monitoring it. I am convinced that in general matchmaking across a wide range of activities/interests is a real problem to be solved, but unfortunately, any kind of service here struggles from a formidable cold start problem
Did I meet my goals:
Not really. I don’t think it was a failed week because I learned a lot about several different business models, but I didn’t do real tests of any ideas. I made the book club matchmaking site but don’t have a clear idea for how to get a first cohort of users (and also lack conviction to continue with the idea).
An issue is that most of my ideas aren’t specified narrowly enough right now, and I also don’t have specific enough ‘target customers’ or ‘users’ who I could theoretically design a demo product for or speak to about their problems.
What’s working / what isn’t?
I was all over the place this week, researching completely disparate topics each day, often multiple in a single day. Aside from this driving me a little bit insane, I don’t think it was especially productive. I don’t feel like I really got much closer to having an actual product idea to proceed with, I felt like I was mostly just doing random research. I would probably be better off at least sticking to one general topic for a week, and try to dig a little deeper and identify and connect with potential users.
Generally speaking, I feel that if someone came to me and said, “Jake, I have this specific problem, can you solve it”, I would probably be able to in many cases. Or if I sat down with an expert from almost any profession and talked to them about the most frustrating parts of their work, I think I’d come up with some concrete ideas.
But at the moment my product ideas are very wide ranging and I don’t have any clear target users. So I’m just sort of vaguely researching different businesses and trying to guess at what problems people have. This doesn’t seem like a good way to do things.
What are my goals for next week?
- Focus on just one or maybe two problem areas, rather than going down a bunch of different rabbit holes
- Identify some people in my areas of focus that I realistically could talk to in order to learn about any problems they’re dealing with
Final thoughts
All things considered, I'm pretty happy with what I’ve accomplished in two weeks and feel that I’m getting the right systems and feedback mechanisms in place.
Two weeks from now, I’d like to have a much clearer set of users I’m trying to serve and narrower problem spaces to build products from.
Bye until next week!
Jake