What does it actually mean to be a first-time CTO at a startup — and how is that role nothing like what most people expect?
In this episode, Mike sits down with Ben Howdle, author of The First CTO, to unpack five years of hard-won lessons across two fintech startups. Ben shares the raw, unfiltered truth about growing into the CTO title, why imposter syndrome nearly got in the way, and how admitting his weaknesses turned out to be his greatest strength.
In this episode:
- How Ben stumbled into software through factory automation and WordPress
- The difference between a startup CTO and an enterprise CTO (and why they're almost incompatible)
- Building your first team from your personal network — and why gut instinct still matters
- The "tech council" advisory board strategy for early-stage hiring
- Managing engineers across wildly different time zones
- Why the CTO role is more sales than engineering
- How AI is reshaping hiring, code review, and the value of "taste" and judgment
- What new engineers should be developing right now that has nothing to do with code
Ben's book, The First CTO, is written for anyone who just landed (or stumbled into) their first CTO role and wants the honest stories — not the polished LinkedIn version.
Resources
Pre-order The First CTO: https://benhowdle.im/first-cto-playbook/
LinkedIn: https://www.linkedin.com/in/ben-howdle/
Ben Howdle: https://benhowdle.im/
────────────────────────────────
LISTEN ON ALL PLATFORMS
Spotify
https://open.spotify.com/show/1V4SjmlnG2sntDnck8UrGW
Apple Podcasts
https://podcasts.apple.com/us/podcast/strictly-from-nowhere-a-podcast-experiment-by-cause/id1804380172
iHeart Radio
https://www.iheart.com/podcast/269-strictly-from-nowhere-a-po-315649122/
YouTube
https://www.youtube.com/channel/UCWAstEyCK6YsKVTTRsQr37w
SUPPORT THE SHOW
Patreon
http://patreon.com/StrictlyFromNowhere
CONNECT WITH US
LinkedIn
https://www.linkedin.com/company/strictly-from-nowhere
Website
https://strictlyfromnowhere.com
────────────────────────────────
FOLLOW JUSTIN ABRAMS | @cuzzinjustin
LinkedIn
https://www.linkedin.com/in/cuzzinjustin/
Instagram
https://www.instagram.com/cuzzinjustin/
TikTok
https://www.tiktok.com/@cuzzinjustin
Facebook
https://www.facebook.com/cuzzinjustin24
Website
https://www.cuzzinjustin.com
────────────────────────────────
FOLLOW MIKE RISPOLI | @mike_rispoli_cto
LinkedIn
https://www.linkedin.com/in/michael-rispoli-cto/
Instagram
https://www.instagram.com/mike_rispoli_cto/
X
https://x.com/michael_rispoli
TikTok
https://www.tiktok.com/@mike_rispoli
Website
https://michaelrispoli.com/
────────────────────────────────
CAUSE OF A KIND | @causeofakind
Website
https://www.causeofakind.com
LinkedIn
https://www.linkedin.com/company/cause-of-a-kind
Instagram
https://www.instagram.com/causeofakind/
X
https://x.com/causeofakind
TikTok
https://www.tiktok.com/@causeofakind
Newsletter Signup
http://eepurl.com/gcc-yj
Newsletter Archive
https://us16.campaign-archive.com/home/?u=847ea1526d6523a41ef1eb5a5&id=48d53e9627
────────────────────────────────
OPEN SOURCE PROJECTS
CodeDojo
https://github.com/Cause-of-a-Kind/code-dojo-core
OCR Ruby GEM
https://activestorage-ocr-demo.fly.dev/
────────────────────────────────
COMMUNITY INITIATIVES
Long Island Technologists
https://www.longislandtechnologists.com
https://www.linkedin.com/company/long-island-technologists-networking
https://www.instagram.com/longislandtechnologists/
────────────────────────────────
Fin Forecasting - Never Lose Money On A Project Again
https://www.finforecasting.com
https://www.linkedin.com/company/fin-forecasting
────────────────────────────────
Brought to you by Cause of a Kind
A boutique software development and startup studio from Long Island, New York
Stand up. Show up. Build.