Kieran O'Connor

Entrepreneur.
Investor.
Author.

I work with VC-backed founders from Y Combinator, Sequoia, Index Ventures and a16z. I've built companies, deployed capital, written books, and hosted conversations that matter — with skin in the game at every stage.

Place. · Founder Tablez.AI · Founding CCO Clera · Founding Partner Calculated Risks Podcast 2× Published Author
Kieran O'Connor
$800K→$9.5M
VC Portfolio Growth
30K
YouTube Subscribers
16K
LinkedIn Followers
2×
Published Author
What I do

Three ways I create value

01
Entrepreneur & Operator

I build things I believe in — from the ground up, with real skin in the game. Currently Founder of Place., Founding CCO at Tablez.AI, and Founding Talent Partner at Clera.

02
Early Stage Investor

I actively invest into HealthTech, SportsTech and AI — reviewing pitch decks weekly. My portfolio has grown from $800K to $9.5M. I back exceptional, integrity-led founders.

03
Author & Podcast Host

Two Amazon-published books on recruitment and team psychology. Host of Calculated Risks — 38+ episodes with exited founders, investors, army commandos, and senior leaders.

Trusted by founders backed by
Y Combinator Sequoia Capital Index Ventures a16z + many more top-tier funds
Experience

Built through doing

Founding CCO
Tablez.AI · Self-employed

The last reservation tool — helping restaurants never miss another reservation. I'm driving commercial strategy as Founding CCO, building the go-to-market from the ground up in Dubai.

Apr 2026 – Present
Current · Dubai
Founding Talent Partner — Early Stage Specialist
Clera · Self-employed

The first AI talent agent — a personal headhunter acting on behalf of top talent. I work closely with the founding team on critical searches across EU and USA, connecting exceptional candidates to startups backed by a16z, Index, YC and more.

Mar 2026 – Present
Current · Remote
Founder — VC Search Partner, Pre-seed · Seed · Series A
Place. · Full-time

Early stage ecosystem enablers. I work exclusively with founding teams who've raised $800K–$9.5M, solving their most complex senior and key hires. Trusted by Y Combinator, Index Ventures and a16z. The people solution VCs actually recommend — relentless on aftercare, expectation management and deadline delivery.

Jan 2024 – Present
2 yrs 5 mos · Cardiff
Early-Stage Investor
Various Startups · Freelance

I actively invest into technology startups across HealthTech, SportsTech and AI. I review pitch decks weekly and back exceptional, integrity-led founders. Current portfolio:

Mous MousFY24/25 Revenue: £29.8M — first profitable year
Pie Tax Pie Tax100K app sign-ups · £250K+ total revenue
Prosper ex-Monzo, ex-Tandem all-star line-up
Zero The Sustainable Money App · First investment
Feb 2025 – Present
1 yr 4 mos · Remote
My Books

2× Amazon published

33 Ways To Become A Better Recruiter
Published June 2024 · KOC Publishing
33 Ways To Become A Better Recruiter & Human

"This book is not just about recruitment; it's about becoming the best version of yourself!" — Alex Kavel, Product Manager

View on Amazon →
Mind Over Metric
Published January 2026 · KOC Publishing
Mind Over Metric: The Psychology Behind Building Winning Teams

"An author who understands team building to as intricate a level as you can imagine." — Richard Lee, Founder of Innovators Uncensored

View on Amazon →

10% of profits donated to City Hospice

Podcast

Calculated Risks

Calculated Risks
Watch Here →

I host a one-hour conversation with entrepreneurs, senior executives and inspiring leaders — digging deep on the risks they've taken to get where they are today. Exited founders, angel investors, army commandos, humanitarian diplomats, and startup founders who've lived it.

38+
Episodes
2
Seasons
1hr
Per Episode
UAE
+UK
Based
Mahmoud Bartwai· Tomas Halgas· Mark Prendergrast· Dodge Woodall· Mark Reed· Irina Heaver· Sophie Smith· Chris Hewish· Idriss Al Rifai· Nick Bradley· David Gurle· Sakr Ereiqat· Ross McKenzie· Leigh Hussain· Cai Gwinnutt· Marco Oliver· George Bellwood· Leroy Brito· James Boyd· Julian Mensah· Justin Pike· Ammar Akhtar· Laura Gemmell· Hannah Williams· Ben Davies· Darryl Morton· Dan Stanley· Aimee Bateman· Mahmoud Bartwai· Tomas Halgas· Mark Prendergrast· Dodge Woodall· Mark Reed· Irina Heaver· Sophie Smith· Chris Hewish· Idriss Al Rifai· Nick Bradley· David Gurle· Sakr Ereiqat· Ross McKenzie· Leigh Hussain· Cai Gwinnutt· Marco Oliver· George Bellwood· Leroy Brito· James Boyd· Julian Mensah· Justin Pike· Ammar Akhtar· Laura Gemmell· Hannah Williams· Ben Davies· Darryl Morton· Dan Stanley· Aimee Bateman·
Omar Al Busaidy· Sayantan Biswas & VP Singh· Keenan Garvey & Kristian Harris· Chris Flynn· Kevin Smith· Oliver Smith· James Smith· Jayne Brewer· Manni Nagi· Joe Tannorella· Omar Al Busaidy· Sayantan Biswas & VP Singh· Keenan Garvey & Kristian Harris· Chris Flynn· Kevin Smith· Oliver Smith· James Smith· Jayne Brewer· Manni Nagi· Joe Tannorella·
Appear on the Podcast

Want to be a guest?

I'm always looking for entrepreneurs, investors, and leaders with stories worth telling. If you've taken calculated risks and have lessons to share, I'd love to have you on the show.

Get in touch