From Setbacks to Strategy with Barry Jolly

Barry Jolly didn’t grow up dreaming of building a media agency. In fact, by his own admission, he drifted for years, working hard, doing what he was told, and playing it safe in a corporate career. Until one unexpected trip to London lit a fire he couldn’t put out.

What followed was far from smooth. His first venture crumbled overnight when the affiliate marketing company he partnered with was exposed as a fraud, wiping out his income and credibility in one swoop. But instead of walking away, Barry doubled down.

He started again. This time for real.

In this episode, James Fleming sits down with Barry for a real, unfiltered conversation about what it takes to get back up after a hit, the truth about agency life, and how he’s grown Jolly Media into a results-driven, values-led company in one of the most challenging industries out there.

Barry opens up about the imposter syndrome, the unpaid invoices, the client mistakes, and the lonely moments most founders keep quiet. But through it all, one thing’s clear, he’s not here to fake it. He’s here to build something that lasts.

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Key moments:

✔️ The failed affiliate venture that wiped out six figures overnight

✔️ How his uncle’s belief planted the first seed of entrepreneurship

✔️ From hotel rooms to hustle: juggling a startup with a full-time job

✔️ The personal lessons that shaped Jolly Media’s values and approach

✔️ Building trust in a broken marketing industry

✔️ Why most agencies overpromise and how Barry’s team does things differently

✔️ Becoming the go-to in renewables through speed, transparency, and strategy

✔️ The moment it all clicked, rethinking marketing around audience awareness

✔️ Why he’s now building a media group and acquiring agencies

✔️ Letting go of control and learning how to lead

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Follow James Fleming:

LinkedIn → https://www.linkedin.com/in/jamesflemingtpwtd/

 

Success or Excuses Instagram → https://www.instagram.com/successorexcusespodcast?igsh=OW51MzlrazkwMXc%3D&utm_source=qr

 

YouTube → https://www.youtube.com/@SuccessorExcusesPodcast

 

Website → https://thepowerwithintraining.com/

 

Follow Barry Jolly:

LinkedIn → https://www.linkedin.com/in/barry-jolly-30a114220/

 

Website → https://jollymediamarketing.com/

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