In February of 2021 I was asked to do a technical evaluation for a startup. The team had 7-10 engineers but lacked senior technical leadership, and the investment team and CEO wanted to make sure they were on track. I've sent this to a few other fractional CTOs who found it helpful, and maybe you will, too.

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Technical Evaluation of a Startup

Most of this is pretty nice. A couple points:
<ol>
<li>Heroku</li>
</ol>
This is terrible advice. Not the idea of having someone else manage your infra, but choice of vendor. There are other vendors that provide better products at more competitive prices, such as <a href="http://render.com" target="_blank" rel="noopener nofollow">render.com</a> or <a href="http://fly.io" target="_blank" rel="noopener nofollow">fly.io</a>. Heroku was the original name in this space, but the competition has passed them by on every level, from features to pricing and engineering velocity.
<ol start="2">
<li>Custom Authentication</li>
</ol>
The point made in the article is “if you want to move off of custom auth”, which is an odd thing to bring up. Perhaps they were asked to comment on the state of auth, which in my opinion earns a ✅ for not reinventing the wheel. Nothing wrong with the OWASP, but this recommendation is directly at odds with the other recommendation to self-manage infra as a means of saving engineering resources.

I think it’s one of the best articles i’ve read so far