Todd Wolfson

Software Engineer

June 24, 2021

I'm a startup engineer. 3x first engineer, former Uber engineer, and have worked at many more startups.

After recently returning to work, it has become clear that knowledge I've picked up over the years, isn't knowledge shared by my similarly aged yet new to startup peers. For reference, here's my LinkedIn profile.

As a result, I'd like to document all the lessons I've experienced and been reminded of.

Please keep in mind that these are guidelines, not rules.

Every decision is a business decision

At a startup, any decision 1 person makes has a significantly larger impact due to the size of the company.

e.g. 1 person at a 3 person startup is 1/3 the company, whereas at a 10,000 person company it's 1/10,000 (handwaving over hierarchy details).

In practice, this most frequently cascades from a person's forward velocity being interrupted, into team and company velocity being impacted.

Terminology: Team implies internally looking, company implies external

Scenario (Underdog.io): You launched by using a Google Forms to intake customers and manage everything via email. Once a month, 2 users try to sign-up concurrently which leads to an error page.
What do you do?

a. Focus time elsewhere - People will try again and it's infrequent enough
b. Revisit when it's once a day - It's painful and upsetting but we can tolerate it for a little longer
c. Unacceptable - Move to a formal database like PostgreSQL
d. Something else

What we did: We weighed out the options (e.g. time/effort vs value) and decided to go with (c) Move to a formal database. We wanted a stellar experience for our users and treating them poorly wasn't inline with that.

To reiterate, this decision was founded in user experience not technical perfection.

For those curious why one might use Google Forms instead of a database from the get-go: Without customers and getting product feedback, we can't guarantee that people will want what we're building.

Negative example (Find Work): As part of building Find Work, I built a lot of visual testing, thinking that it would help reduce bugs. In practice, it ate a lot more time than it saved and should only have been done during large CSS migrations.

Build exactly what you need

"Build exactly what you need and nothing more" is how I frame this in my mind (also sometimes YAGNI or JIT).

When we try to predict what we'll need for the future, we almost always get it wrong. And thus we do a lot of extra work (both building and maintenance) for little gain.

This can come up in many ways:

  • Excessive services (e.g. API + web app + admin tools, when 1 monolith would have sufficed)
    • High maintenance costs for: Concurrent feature development and deployment, writing API interfacing code per endpoint
  • Anticipating a feature that's not being built yet
    • Added costs: Thinking, building, and maintaining new logic edge cases which aren't even being used
    • Following this rule doesn't mean writing yourself into a corner, building with openness in mind should always be followed
    • Exception to the rule: Can be ignored if feature is next in the queue
  • Anticipating data model correctness
    • Cost: Building out something which falls flat in practice and having to rebuild it again
    • Best handled by experimenting with UX prototype first to verify it feels right (complex state in Cynefin framework)
  • Many more varieties

Stronger rant on anticipating features: Startup goals and directions change swiftly.

In 1 day, you might pivot your whole product, shift your target audience, or change engineering priorities.

In all these cases, shipping frequent small well-contained PRs (easily removed features) is critical for maintaining high business velocity and a tight feedback loop.

Scenario (Underdog.io): You're building the data model to save resume/CV storage paths for candidates. We might want to have resume history in the future.
What do you do?

a. Don't build historical support yet - We don't need it and it will significantly complicate logic
b. Build historical support now - We feel confident enough that this will be a feature we support
c. Build audit table for future backfill - A little more work but can backfill into historical info
d. Something else

What we did: (a) Refuse to build historical support yet. Among the massive backlog of other work to be done, it was at least 6 months away before being a practical need. This is a relatively clear-cut example, others may be a lot more muddy.

Negative example (Underdog.io): When I joined, we had 2 light services talking directly to the same database. This was impractical for database migrations and model updates. I weighed combining them into 1 service or building a third API service.

I went with the latter which wound up costing a lot more hours with API interfacing code yet little benefit for our scale.

Invest in fundamentals

The early architecture and service(s) your company settles on will be with you for a while (e.g. at least 2 years).

As a result, it makes sense to establish fundamentals that help team happiness, confidence, and velocity.

My short list is:

  • Quick and easy deploys - One click or script with easy revert plan (something will go wrong eventually)
  • Fast deploys - Ship a feature and be able to check it while it's still in your headspace
  • Error monitoring (e.g. Sentry) - Know when something broke in production, don't rely on customers telling you (bad experience for them too)
  • Linting - Catch errors early (e.g. typo'd variables) and help keep code simple and consistent
  • Basic testing - Nothing complex needed but something so you can dive into TDD when practical
  • CI - Know when linting or tests break, and prevent accidental drift

When all these efforts are summed together, the seconds here and there accrue into many hours saved when done early in the 2+ year journey.

Positive example (Standard Cyborg): When I joined, the deployment process was not standardized, slow, and easily error-prone.

  • Internal library: Required manual build, commit, and push
  • Web app: Build internal library, commit, push, and deploy to Heroku via git push
  • Lambda: Depended on developer computer's existing dependencies and running multiple commands like installing and zipping by hand. Also dependent on internal library

After formalizing and standardizing these, the process was smoothed out and deploys became trivial.

Stick to boring and simple

Being clever or using shiny technology is often a good way to make our future selves waste time. This has been well laid out by @mcfunley's Choose Boring Technology.

Examples I've seen time and time again:

  • Using a non-SQL database (e.g. MongoDB) - Eventually run into querying, performance, and/or integration issues
  • Adding a different language or framework to the existing stack - Now every existing and new engineer needs to learn this as well
  • Choosing a new language or framework (e.g. under 2 years old) - Likely will run into performance issues, only does 80% of what you need but won't find out until 3 months later, or the API will change on you
  • Rewriting a service from scratch instead of progressively fixing the existing one - Takes a lot more time and little company value is actually gained

If you're starting outright, I highly recommend using:

  • PostgreSQL - Has less footguns than MySQL and better open source ecosystem support
  • Django or Rails - Has a lot more batteries included than DIY middleware stacking needed for Flask, Express, and Sinatra
  • Bootstrap - Well thought out design system with plenty of components
    • Only practical if your designs lean into Bootstrap patterns, otherwise will be fighting Bootstrap
  • That's it, nothing else is usually needed for a web app

Positive example (Standard Cyborg): The stack was Rails and Bootstrap. We were able to turnaround features in an afternoon due to all the tooling Rails provided and no excess work like API interfacing.

Negative example (Verbling): This was in React's early days. All the shiny libraries were being used (e.g. React, GraphQL, MongoDB) and as a result, there was a lackluster ecosystem to support them (e.g. no admin tooling, running into MongoDB issues, no React server-side rendering).

It was probably great to use in the beginning but clearly it was reaching a breaking point without any practical benefit to the company.

Do it right the first time

Also phrased as "fix it now or it will never get fixed".

As mentioned in Build exactly what you need, startup priorities can change within a day. The time you thought you had to formalize feature X is now gone and is unlikely to come back within the next 3 months.

Do it right the first time. Take the time to formalize the PR to stand the test of time. It doesn't need to be bullet proof but it shouldn't have any footguns in it either.

If there's not enough time to formalize it properly, then consider deferral by leveraging error monitoring and defensive programming to be aware of when it breaks (e.g. assert calls for unexpected values).

Positive example (Standard Cyborg): I built a prototyped solution with O(n^2) runtime for some vertex properties. It worked great but we'd inevitably run into issues for larger meshes (more vertices, bigger n). As a result, we took the time to code up an O(n) solution before landing the PR.

A deferral solution would have been an assert or Sentry.captureException call for when the vertex count is too high.

Negative example (Underdog.io): We were adding created_at and updated_at columns to our models but we messed up the casing (i.e. createdAt).

We had to do a painful migration to fix all of this, though the alternative would be one-off casing issues occuring for the rest of the codebase's lifetime.

Fix as you go

Some issues have been long standing or are architectural so they skip the "fix it now" guideline.

For these, I'll often adopt a "run and gun" style to resolve them.

I start by documenting everything I see (e.g. personal note, catch-all task, or knowledge base document). When I next have some downtime (e.g. waiting for feedback on a feature), then I work on these tasks.

Sometimes this resolves via directly opening a PR for the feature.

Other times, it involves writing up a proof of concept (PoC), showing a demo to other engineers, and getting their support/consent.

Positive example (SilviaTerra): We were using Django REST Framework but mostly for its JSON request/response logic, not actual REST resources. I wrote up a PoC, pitched it, and we progressively shrunk/simplified the codebase (endpoint by endpoint) over the course of 1 month.

Negative example (Verbling): The testing system was slow and brittle. The engineering velocity was greatly reduced due to limited attempts to improve it. Without intervention, it would continue to get slower and impact company velocity.

What did I leave out

There's some lessons that felt like they were either too much opinion, not specific to startups, or require their own article. Here's a quick rundown:

  • Resumable work (not significant enough to dive into)
  • What and when to test (opinion)
  • Documentation can help organization scale (opinion)
  • Bus factor (well-established in open source)
  • 1:10:100 time investment between design, development, and post-release fixes (not specific to startups)
  • Backpressure, how and when to push back against work/timeline as well as compromise (not specific to startups)
  • Build vs buy (not specific to startups)
  • Time estimation and zooming in like a coastline (not specific to startups)
  • Optimal time investing (might become its own article)
  • Probably many more lessons
  • If there's something that you'd like to be included, please let me know

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