The Bootstrapped Founder Newsletter Episode 21 – April 3rd 2020

Dear founder,

I have had a lot of interesting discussions as a result of last week’s article on building or buying. More than ever, other technical founders reached out and shared their perspectives, which ranged from agreeing wholeheartedly to almost complete dismissal. In every case, I had a pleasant conversation that was — hopefully — enlightening for each participant. I can only encourage you to send me an email or hit me up on Twitter: there is a lot to learn from each other.

This week, let’s dive deeper into picking services: Making Tech Choices: Don’t Add Risk to an Already Risky Business.

When we decide to buy instead of building, we often do so because we know we have limited knowledge of the very field that we’re trying to buy a solution for: very few of us are experts in payments, authentication, invoicing, taxes AND the one thing that makes our businesses uniquely useful to solve critical problems.

So how can we find the best solution when we are ill-equipped to make that choice?

I propose that any founder looking for technology should find the best answer to one question: “Will you be able to use this well for a long time?

This question implies three kinds of alignment that need to exist for any given technology: Founder-Technology-Fit, Purpose-Technology-Fit, and Technology Durability.

You have Founder-Technology-Fit when you, the founder, have a clear understanding of the requirements and opportunities that come with the chosen technology — and that they fit your needs. There is always the risk that your choice will have some hidden caveat, making certain things hard or even impossible. Here are a few ways of increasing the likelihood of Founder-Technology-Fit:

  • If you know it, use it. Don’t learn new tech because it would be “worth learning.” You’re building a business, not a school. You want to get to the point of validation (or invalidation) as soon as possible, not spend two months building Hello-World-programs. If you ever want to make money in SaaS, the safe choice is to pick the technology you know and to build something from there.
  • Make sure you have all the knowledge you need to evaluate a piece of technology. Read up on other founders’ experiences with a service, study their status page, read blogs from the industry that they’re in. Get yourself into a position from which you can make a mostly unbiased choice.

Find technology that actually helps you with your business. You’ve made the best choice when Purpose-Technology-Fit is reached: good tech solves your business needs today and in the future. Here is what to look out for:

  • Beware of overly specific tools. They might serve your requirements right now, but what about a few months from now? What about a year? Can you be sure that your roadmap and theirs are aligned? I’ve made this mistake with FeedbackPanda. We picked a tiny niche hosting service for our production system because it was perfect for us at some point. Later, they experienced maintenance issues, and because there was no standardized way to interact with their system, we had to migrate our whole cluster over to a much bigger cloud hosting provider overnight. Not fun.
  • Consequentially, don’t discount the generalist solutions because they need more customization. The flexibility afforded by a system that can be expanded in the future is worth a few hours of extra effort. A business is an ongoing concern, and your product is a moving target. Don’t lock yourself in.

When we talk about Technology Durability, we’re not just looking at how stable the actual solution is. We’re interested in the long-term perspective of using that particular technology in your business. Here are a few guidelines for picking tech that won’t be a time-bomb for your service:

  • Choose popular technology. If there are a plethora of educational resources and excellent documentation, the chances are that many edge cases will have been found and solved already.
  • Look for vibrant communities. Learning will be more accessible when you have a lot of people who can help you understand new concepts and the error of your ways. A big community usually produces many helpful open-source libraries as well.
  • Choose mature technology. Most technology survives for a long time because it has proven itself to be durable, performant, and reliable. New tech might look exciting, but you can’t be sure that you do not only see the happy path. I made this mistake once, using MongoDB when it was relatively new, and the project really didn’t require a document-based database. I spent weeks building things like relationships that would have been already present and highly performant with a SQL solution.

Guidelines to Pick A Technology

Over the years, I have collected a list of attributes that technology should exhibit to be a good fit. It doesn’t have to have them all, but if it misses more marks than it hits, it might not be the right choice for a bootstrapped business. You’ll have enough work on your hands from serving a niche audience with a likely ever-changing problem. You don’t need to worry about your tech stack at the same time.

Technology that you can use well for a long time has these attributes:

  • It can be used to solve your problem. You can find stories of how other businesses have used this technology to fulfill a similar need to yours. You can evaluate the technology without spending months of your time.
  • It’s popular. You find a lot of resources and opinions about it on the web. There are books on the technology for beginners and experts alike.
  • It’s surrounded by vibrant communities. There are forums, Twitter communities, whole Slack instances dedicated to the technology, and they’re active.
  • It’s reliable. You can find a lot of established businesses that use it in their production systems without too many disastrous stories.
  • It’s scalable. Small businesses and big businesses are using this technology.
  • It’s extensible. You can find a lot of libraries and integrations for the technology. You can also find information on how you can get them to work.
  • It’s mature. You can find a history of how the technology was adapted to fulfill the real needs of the people using it.
  • It’s well-maintained. You can find recent and regular updates to the service, either in a changelog or in the source code itself. People who report their problems are responded to, and their concerns addressed.
  • It’s replaceable. You can find alternatives to the technology that you can use in its stead should it become problematic or ineffective.

If a technology you’re looking at checks all or most of these boxes, use it. If not, look for one that does. If you do this for all the choices you will need to make, you’ll end up with a very maintainable collection of technologies that will stand the test of time.

You can learn more about how to make tech choices on my blog in the article called Making Tech Choices: Don’t Add Risk to an Already Risky Business.

Links I found Interesting

Einar Vollset, a co-founder of TinySeed and no-bullshit twitter aficionado, released COVID-19 Business Relief: An Overview for Startups, Consultants, and Freelancers on the MicroConf website. If you’re affected by the economic chaos surrounding the pandemic and live in the US, this guide will help you find the right help, right now.

In the “real world,” we often talk about luxury goods as status signaling devices. Not so much in SaaS. Julian Lehr explains in Signaling as a Service how the attention economy of social signaling works at scale, and how artificial barriers to entrance aren’t working too well there. In essence, the actual value lies in making memberships free and monetizing signal amplification. With examples like Tinder and Fortnite, Julian shows how the amplification of signals at scale is the new Rolex. A very insightful read for anyone who wants to work on their brand and positioning.

I regularly think about cognitive bias ever since I started writing this newsletter and the articles on my blog. This week, I found something that summed up everything I ever went through as a developer when it comes to biases that hindered my learning and limited my journey: Cognitive Biases In Software Development by Stanislav Myachenkov. Not only are the examples hilarious, but this blog post also shows that new and seasoned developers alike aren’t safe from making the wrong choices.

Bootstrapping Success Stories I Noticed

I ran into the wonderfully designed website of Steven Yung, who turned his journey from developer to entrepreneur into a classic-video-game-like interface called From Dev to Maker. As an MMORPG fan, the idea of setting yourself quests to accomplish objectives and gain experience is very appealing. Enjoy this witty and joyful example of self-motivation.

Garrett Moon talks about Killing Your First Product and how TodayLaunch was sunset back in 2013 after two years. This post went 4/4 when it came to the mistakes I made with prior startups: wrong assumptions, no room to innovate, featuritis, and unsustainable business models. Been there, done that. Garrett is now working on CoSchedule, blogs a lot, and provides a very insightful perspective into marketing, writing, and building a brand — and it seems to work out much better this time around.

Thank you for reading this week’s edition of The Bootstrapped Founder. If you like what I wrote about, please forward the newsletter to anyone you think would enjoy it too.

If you want to help me share my thoughts and ideas with the world, please share this episode of the newsletter on Twitter or wherever you like, or reach out on Twitter at @arvidkahl.

See you next week!

Warm Regards from Berlin,