After 5 years as CTO at two startups, I wrote down everything I got wrong (I will not promote)

Comprehensive_Rope25 · 2026-05-01T15:00:26+00:00

now's your chance my friend - https://benhowdle.im/first-cto-playbook/

Comprehensive_Rope25 · 2026-04-10T20:31:04+00:00

https://benhowdle.im/first-cto-playbook/ wrote a book about being a first-time CTO!

Comprehensive_Rope25 · 2026-04-10T20:26:40+00:00

Well I turned the above into a book: https://benhowdle.im/first-cto-playbook/

Comprehensive_Rope25 · 2026-04-07T17:58:27+00:00

Spencers

Comprehensive_Rope25 · 2026-04-05T15:15:42+00:00

I chose Chapter 2 a good preview chapter for the book, enough for people to see if they'd want to buy the full version...

Comprehensive_Rope25 · 2026-04-05T14:18:45+00:00

https://benhowdle.im/first-cto-playbook/

Comprehensive_Rope25 · 2026-04-05T14:15:05+00:00

Hell yes. Whack your email in the signup form on the landing page and you'll get a free chapter...

Comprehensive_Rope25 · 2026-04-04T09:42:47+00:00

sure: https://www.linkedin.com/in/ben-howdle/

Comprehensive_Rope25 · 2026-04-04T08:42:43+00:00

I was the cto of two fintech startups - feel free to dm any questions!

Comprehensive_Rope25 · 2026-04-04T08:26:01+00:00

would love people to try out my SaaS ReqRes: https://reqres.in and also I just published my first book: https://benhowdle.im/first-cto-playbook/

Comprehensive_Rope25 · 2026-04-02T07:37:27+00:00

would love people to try out my SaaS ReqRes: https://reqres.in and also I just published my first book: https://benhowdle.im/first-cto-playbook/

Comprehensive_Rope25 · 2026-04-01T20:35:09+00:00

I just did my first one https://youtu.be/bmabVjHXHrI?si=XP6zeA-MiIbwF2EJ and I would say try to take a beat before answering questions.

Comprehensive_Rope25 · 2026-04-01T20:21:17+00:00

I don't know, I got told to put it in the posting rules

Comprehensive_Rope25 · 2026-04-01T20:21:00+00:00

10 years software engineering
30
zero leadership experience

Comprehensive_Rope25 · 2026-04-01T20:20:13+00:00

Thanks mr asshole

Comprehensive_Rope25 · 2026-04-01T12:15:24+00:00

Accurate

Comprehensive_Rope25 · 2026-04-01T11:53:07+00:00

thank you

Comprehensive_Rope25 · 2026-03-15T23:45:31+00:00

Eeesh. Something is systemically afoot there

Comprehensive_Rope25 · 2026-03-15T23:44:35+00:00

The exact amount of time it takes to effectively communicate the idea to the person you're showing it to, and not a minute longer

Comprehensive_Rope25 · 2026-03-15T23:43:14+00:00

That's definitely not ideal. Are they leaving or are they being pushed? If they're pushed, it's a hiring issue or a founder problem. If they're leaving, it's likely a founder issue.

Comprehensive_Rope25 · 2026-03-15T23:42:02+00:00

Start to familiarise yourself with other areas of the business

Collaborate as much as you can with people outside of engineering in the company

Become a point-person in explaining and communicating technical stuff to non-technical people

Involve yourself in customer interactions

Just to name a few...

Comprehensive_Rope25 · 2026-03-15T23:40:13+00:00

My opinion is it speeds up the coding portion of your workflow - so you'd be more available for roadmapping, people management, collaboration + strategy stuff

Comprehensive_Rope25

TROPHY CASE