New Digital Playbook
The First CTO
The Job Nobody Explains
A playbook for the loneliest job in startups
From the creator of ReqRes - used by 30,000+ developers every month
Launch price £99 - Save 30%
"The hardest part isn't the technical fires - it's the isolation."
- From the conversation that started this book
You're making decisions alone that could sink the company. You're hiring engineers for the first time and terrified of getting it wrong.
Your founder changes priorities every week and you're the one who has to make sense of it.
You're context-switching between architecture spikes and homepage copy. You're wondering if what you're feeling is normal or a red flag.
And there's no one else who holds the full context - no one who understands the weight of it.
You're isolated. You're improvising. And nobody told you this is what the job would actually be.
"The job isn't one job. It's five jobs in a trench coat."
This playbook is everything I learned the hard way - so you don't have to.
What's Inside
Five parts, zero theory
The tactical handbook for first-time CTOs who are making it up as they go
War stories from building fintech platforms where real money moved to real governments - and what I learned the hard way about security, hiring, founders, and staying sane.
- How the job changes at 5 people, 15 people, 30 people
- The founder relationship - your real boss, your real constraint
- Making architecture decisions at 2am with incomplete information
- "Good enough" as a discipline
- Your first hire matters more than your first architecture decision
- The expensive mistakes I made so you don't have to
- Knowing what not to build
- When to say no (and how to say it without losing trust)
- Why "I'll just fix it myself" is the most expensive sentence in startups
- What success looks like (it's not what you think)
Chapter content subject to change in final version
Who This Is For
If you're wondering whether you're doing it right
- You just became CTO and you're making it up as you go
- You're the only technical voice in a room full of business decisions
- You're wondering if you should have taken this job at all
- You're managing a founder who changes priorities every week
- You're context-switching between architecture spikes and homepage copy
- You're wondering if what you're feeling is normal or a red flag
- You're isolated - there's no one else who holds the full context
- You're a senior engineer wondering if you're ready for the CTO job
About Me
I've made every mistake in this book
I'm Ben Howdle. I've been CTO at two early-stage startups:
- Letter (3.5 years) - Built the platform from zero, led the engineering team, worked directly with the CEO
- WorkMade (1.5 years) - Promoted from engineer to CTO, managed 6 engineers, shipped financial infrastructure handling real money and tax data
I've also spent 15 years shipping products for companies like Clerk, GoDaddy, Cisco, and Soho House.
I've been where you are. I've made the hiring mistakes, the architecture calls with incomplete information, the founder management failures. This playbook is what I wish I'd had when I started.
What People Say
From people I've worked with
"Ben intuitively knows where to cut corners for speed and where shortcuts would come back to haunt us."
"Ben had the rare ability to turn an idea from concept yesterday to a working build in production today. He knew exactly where to focus our energy for the biggest impact."
"His early contributions have saved a potentially limitless amount of developer time, pain and costs down the line."
Limited Pre-Order Pricing
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Digital delivery on launch
Need More Support?
Work with me directly
The playbook gives you the playbook. But if you need someone in your corner for the day-to-day - architecture reviews, hiring decisions, managing up to founders - I offer monthly CTO coaching retainers.
CTO Coaching & Advisory
Weekly calls, unlimited async access, architecture & hiring reviews
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Have questions? Email me at hello@benhowdle.im