Why every founder needs an ‘Oh Shit Document’, with Mat Bennett.

ByKelly Molson

In this episode of Lifestyle is a Plan, I’m joined by Agency Advisor Mat Bennett.

Mat started his agency in the early days of the web and ran it for 25 years before selling and exiting. He now advises founders of small UK digital and creative agencies, helping them make better decisions sooner.

His style is direct and pragmatic: fewer frameworks, more decisions, trade-offs, and follow-through. He calls it “velocity, not speed” -momentum plus direction, not just activity.
Mat’s strength is commercial judgement: positioning, pricing, focus, and delivery constraints. He writes at matbennett.com, sends a fortnightly email called Try This, and runs a quarterly Agency Loop survey.

“If you disappeared from your business for a few weeks, with no notice and no laptop, what would break first?” This is a question Agency Advisor Mat frequently asks founders he supports, to understand where the agency still depends entirely on them.

But it comes from a place of lived experience. Whilst running a busy, growing agency, Mat was suddenly hospitalised for a series of prolonged spells following a cancer diagnosis.

A heads up – we do talk about cancer diagnosis and baby loss in this episode, so please pause this episode for another time if you need to.

What you’ll discover:

  • Why every founder needs an Oh Shit document
  • What are the key things that document should contain
  • Why we all need to structure our businesses to allow for “thinking time”
  • How the process of writing down operating procedures identifies inefficiencies
  • How selling a business can be a strategic safety move
  • How strategic co-ownership can be a critical resilience tactic
  • What Mat would do differently this time around as a solo founder

If you’re a founder who’s ever worried about what would happen if you had to step away unexpectedly, this episode is an important listen.

Listen here

Guest details

Website: https://www.matbennett.com/

LinkedIn: https://www.linkedin.com/in/matbennett/

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2Bobs: https://2bobs.com/

Brought to you by

Lifestyle is a Plan is brought to you by me, Kelly Molson – an agency advisor on a mission to support solo founders build the agency they want.

I’m here to show the agency world that “lifestyle agency” isn’t a cop out. It’s the future of sustainable growth.

Join my Lifestyle is a Plan newsletter at kellymolson.co.uk.

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