The Mergers Podcast

Tech, Banking & Surviving 2008 [Thomas Hughes, Workera]

The Mergers

Tom Hughes’ career has been anything but normal.

He started out as a Dublin kid tracking stock prices on BBC Ceefax, went into equity research before the ’08 crash, and then got 'super-fired' like thousands of others.

From there he somehow blagged his way into Bloomberg with a bold doorstep pitch. He’s moved through private capital research (Gartner), relationship intelligence (Affinity), commercial leadership roles, and now into the world of AI and enterprise upskilling at Workera - where an “AI mentor” isn’t just hype, it’s the actual product.

In this episode we talk about bouncing back from setbacks, breaking into tech from finance, why not every conversation needs to have an immediate outcome, and what AI is really changing inside big organisations.

What You’ll Learn:

  • How to recover from losing your job in a downturn (and why persistence matters most).
  • The “just show up” story: how Tom literally forced his way into a Bloomberg interview and walked out with a job.
  • What shifted after the financial crisis: moving from gut feel to data, risk, and tooling in banking, PE & VC.
  • Inside AI transformation: why skills benchmarking and agentic assessment matter... and why most teams are miles behind!
  • A masterclass on sales and partnerships at scale
  • Networking that lasts: why being useful first (not transactional) is the key to compounding relationships.

Chapters
00:00 — Sponsor & disclaimer (Cadro, FCA-regulated)
01:27 — Live at The Bottle Cocktail Shop; meet Tom Hughes
02:17 — Dublin roots, Ceefax and learning markets at age 8
08:46 — Getting fired in ’08; the empty trading floors moment
10:58 — A year of rejections & café CVs → the pivot into tech
20:43 — Newspaper ad → Bloomberg: calling reception, finding the hiring lead, and turning up without an invite
24:10 — Why AI won’t replace hustle; what hiring managers really value in salespeople
25:27 — From Bloomberg’s “no negotiation” culture to startup chaos; Gartner → Affinity → VC ecosystem
30:11 — AI readiness vs reality: assessing skills at massive scale; agentic assessments
35:22 — Coaching at scale with Gong/Clari; fewer blind spots, better forecasts
37:57 — Networking that works: why long-term compounding beats short-term transactions


Disclaimer
This episode of The Mergers Podcast is sponsored by Cadro Technologies Limited, an FCA-regulated investment firm. Sponsorship does not imply endorsement of any views expressed in this podcast. The information discussed is provided for general informational and educational purposes only, does not constitute investment advice, and should not be relied upon as a basis for making investment decisions. The hosts and guests speak in a personal capacity. If you are considering investing, you should obtain independent financial advice tailored to your individual circumstances.