The Content Trenches: What It Really Takes to Win With Video | #122: Jack Gaisford
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Jack Gaisford is the founder of The Content Club™, a community helping founders create confident and consistent videos that drive real business results. Before launching it, he spent seven years running his agency Odyssey, producing thousands of videos for brands like Microsoft, Xbox and Panasonic. That experience led him to realise the biggest wins come when founders learn to master video themselves.
In this episode, Jack shares his journey from early YouTube experiments to becoming one of LinkedIn’s original video creators. You’ll hear practical advice on building your brand with video across LinkedIn and YouTube, stories from helping founders turn content into clients, and the mindset that’s kept him showing up for years while growing a business and enjoying family life.
Connect with Jack:
https://www.linkedin.com/in/jackgaisford/
https://www.instagram.com/jackgaisford
https://www.youtube.com/c/JackGaisford
https://the-content-club.co.uk/
Timestamps:
00:00 – Why clients from content stay longer and trust more
00:46 – The myth of quick wins and 90-day success
01:00 – Intro and welcome
01:22 – Who is Jack Gaisford and what is The Content Club™
01:55 – Early YouTube experiments and teaching himself video
02:24 – Growing a gaming channel to 15K subs before shutting it down
03:07 – Bullying, quitting YouTube, and what he wishes he did differently
04:51 – Why Gen Z dreams of becoming YouTubers
05:45 – Where content creation is heading in the next 5–10 years
07:36 – Starting YouTube again after years on LinkedIn
08:24 – YouTube vs LinkedIn: platforms with different incentives
09:25 – Data obsession, analytics and A/B testing on YouTube
11:12 – Why YouTube is still Jack’s favourite platform
13:19 – The creators and channels that inspire him
16:22 – LinkedIn beginnings: early video hacks with his dad’s company
18:02 – Building his first agency and landing global brands
18:55 – Why he shut the agency and launched The Content Club™
19:41 – LinkedIn as a huge untapped opportunity for creators
22:09 – How to stand out and break through the noise
24:29 – Jack’s advice: go harder and commit longer than others
27:49 – Why most content success is a long road, not quick wins
28:46 – £2M in revenue from organic LinkedIn content alone
30:10 – Is video still growing on LinkedIn?
31:58 – How social media has shifted from social to relevance
34:47 – What really makes content work in 2025
36:45 – Why you only learn by doing the thing
37:34 – The personal “why” that keeps Jack showing up
40:05 – Gaming, Rocket League, and switching off
41:26 – Gym, health, and balancing work and life
43:57 – Where to find Jack online
44:30 – Final advice for anyone struggling with content creation
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168 episodes