Solopreneur owner of 20k/month Rails app wants to give inside view

Ten years ago I built a niche marketplace and have been living from the revenue ever since. It was designed to be a lifestyle business from the get-go so I spent a ton of time initially optimizing and automating everything.

I want to create a stream that gives a behind-the-scenes, nothing-hidden, look at what I've built and how I work, but I've no idea which topics are most interesting. If I learned one thing in creating my business, it's that it's all too easy to create something that no-one wants.

So what topics would you like to be covered?

Some ideas I had were

**Coding**

1. generating a maximally enjoyable development environment (e.g. seeding data, simulating cron, mirroring production as much as possible etc.)
2. removing brittleness from integration tests that run on circleci
3. dealing with the shitshow that is sales tax accounting across multiple currencies
4. detecting and recovering from production bugs asap
5. dealing with the real-world mess that is imperfect user input (e.g. when they type emails with a leading space or inconsistent capitalization; when they create a tag that is almost the same as a previous one — like E Guitar vs. Electric Guitar—and now your data is split across two areas)
6. discussing the 8+ year consequences of certain architectural/software design issues
7. streamlining massive amounts of config
8. multi-redundant systems of backup to prevent disaster
9. designing error messages and a logging strategy that speeds up recovery from errors
10. a tour of the most evil, insidious bugs I dealt with over the years (I keep a diary for them)
11. payment systems in-depth (refunds, errors etc.)
12. caching systems for performance

**Business/marketing**

1. how I use data to decide to add/remove a feature
2. AB testing a web app
3. technical SEO (microdata, site structure for internal links, google's tools, sitemaps, etc.) — I get 85% of my traffic (and therefore revenue) from SEO, so I know a thing or two
4. how I use JS and integration tests on all tracking code (critical to get right in my business)
5. auto-email systems to previous customers for extra sales
6. Adwords workflow to drive revenue
7. Analytics workflow to figure out what content working
8. Writing copy that gets sales (what worked for me vs. didn't)

*If there's something you're interested in but don't see mentioned above, please do share.*

**EDIT:** Wow, it seems very clear there's interest! Awesome, I am now extra motivated.

(Currently traveling so it's unlikely I'll really get going until I'm back home in late March)

44 thoughts on “Solopreneur owner of 20k/month Rails app wants to give inside view”

  1. > discussing the 8+ year consequences of certain architectural/software design issues

    I’d be pretty curious about that! But what also what worked! I’ve worked on a few older projects and the main thing I’ve found that gives me confidence in the code is a damn good set of factories 🙂

    Reply
  2. This will be a fascinating presentation! I’m curious about cashflow management, especially in the early days. Did you implement any special tactics to bridge yourself over from month to month? How did you “survive” until you got to a sufficient cashflow for base living and full-time dedication? What was life like during this time? How did you push out your customer base to achieve this threshold? Was there a particular marketing and even sales strategy that worked for you?

    Reply
  3. That’s all great, thanks for willing to share.

    Some more ideas:

    * How to get feedback from users
    * How to plan for new features
    * Cross browser compatibility
    * How did you came up with a fair price/subscription value
    * subscription vs one time payment?
    * How to not over engineer a functioning application
    * Did you follow Rails folders architecture? If not would be nice to see how you have organized the app.
    * FE frameworks?
    * Indispensable gems?
    * If it is data intensive, how to model in order to cut DB size

    Reply
  4. I would love to learn about your experience!

    My biggest challenge has been – finding the trade-off between development time (which is fun!) and business-building time (networking, marketing, soliciting users, getting feedback, building sales funnel, etc). So I’d love to head your approach to that!

    Reply
  5. I like all of the topics. I’d also add testing, as when working as a single dev, one usually needs to draw a line and test only the most important parts of an app. I’d love to hear your experience with that long term — what did you prioritize and how it turned out.

    Reply
  6. I would love to hear about

    > dealing with the real-world mess that is imperfect user input (e.g. when they type emails with a leading space or inconsistent capitalization; when they create a tag that is almost the same as a previous one — like E Guitar vs. Electric Guitar—and now your data is split across two areas)

    > discussing the 8+ year consequences of certain architectural/software design issues

    > streamlining massive amounts of config

    > multi-redundant systems of backup to prevent disaster

    Reply
  7. Honestly, from just your post here and the fact that you’ve managed to create a succesful endeavor for yourself, is enough for me to want to hear most everything you have to share.

    Great idea, and good topics already!

    If anything, I’d add topics and themes around mental strength, ups and downs of going solo, stuff like that.

    (edit: wording)

    Reply
  8. I am CPA and work with small businesses, several in the e-commerce space. I haven’t found a consistently good solution to integrate sales data (and payment processor fees, lags on funds being delivered, etc.) into an accounting system like QuickBooks or Xero. Any insight into what you’re using would be great!

    Also sales tax – are you using TaxJar or Avalara? Something else?

    This being what most people consider the boring stuff means a severe lack of tutorials/guides for integrating with even the most common platforms like Shopify or woocommerce. This would be so valuable for small business accountants! Thanks again!

    Reply
  9. Nice! It would be great.

    I have 10+ years as a CEO/CTO in RoR companies and I would be super happy to give/receive feedbacks!

    RemindMe! 2 weeks

    Reply
  10. **For Coding**

    General infrastructure

    * How do you decide which cloud service provider to use? (ex: Heroku then switch to AWS when there’s more users/need or start with AWS, etc.)

    **For Business / Marketing**

    UI/UX design

    * How do you get a site to look good and provide a good experience for users?

    * Do you hire outside designers?

    * How do you decide what price to set? Contract structure?


    Thank you for doing this. Sounds super informative!

    Reply
  11. Personally I’m interested in #6 because the decisions we make now will have consequences in the future (whichever way we go)……..would be interested to hear your take………also interested in how your trap/log in production (i.e. #9).

    **Summary: #6 and #9**

    Reply
  12. I’d be interested how you would tackle apps in a marketplace ecosystem: think ‘App Store’ or Google Play Store or Shopify App Store.

    Reply
  13. \- Which has been your biggest regrets of doing/not doing so far? Why?
    \- If you could start over again, what would you do differently with the experience gained in the process? (Mostly IT perspective)

    Reply

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