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Why Smart People Fail When the Work Gets Hard - Jack Delosa #132

September 28, 2025 · 1 h 31 min

Show notes

Jack Delosa's argument is that people do not fail because they lack ability, they fail because the work gets hard and the mind retreats into what is familiar. He says his best clients have rewired it the other way round: comfort is the warning sign, discomfort is confirmation.


Jack Delosa is the founder of The Entourage, a business education company.


What you will learn:


- Why he says the brain is built for survival rather than for success, and what that costs you

- How his top clients learned to read comfort as a warning and discomfort as a signpost

- What he calls a money making activity, and why most founders spend almost no time on it

- Why he goes after the biggest constraint in a business rather than its biggest opportunity

- How he hires A players, and why he says most people are recruiting from the wrong pool


Chapters

00:00 People do not avoid goals, they avoid hard

03:21 Frustration or inspiration, and which one moves you

07:51 Finding the mission inside the work you already do

11:22 Why some people take an extra year to understand it

16:48 Reading comfort as the warning sign

20:14 One step forward, three steps back, and why that is normal

24:21 Getting through the hard stretch

31:31 What separates the top one percent of his clients

35:54 Working through people instead of doing it yourself

39:41 Marketing and sales are the money making activities

44:22 Attack the biggest constraint, not the biggest opportunity

47:48 Thinking is the hardest work there is

56:35 Building a team that is at an all time high

1:00:14 How to actually hire an A player

1:05:38 Why everyone's org chart looks the same

1:09:50 Making organic content that does not feel like an ad

1:13:34 What comes after organic, and the funnel most people skip

1:17:37 Going pro on social, and copying the recipe

1:21:49 Business and plant medicine as vehicles for growth

1:25:34 Why AI's curve is different to the internet's


Jack Delosa builds people who keep going when the market doesn't. Property should work the same way.


Most properties only make money if the market does. The ones that pay for themselves from the day you settle are bought differently, and it comes down to four points.


Get the free guide: https://go.bothsides.au/score


Bothsides:

◼️ The weekly email - https://bothsides.au

◼️ Bothsides Buyers Agency - https://www.bothsidesbuyersagency.com.au

◼️ Dan - https://www.instagram.com/daniel_beardall/

◼️ Watch on YouTube - https://www.youtube.com/@bothsidespodcast


General information only. Not financial, tax, legal or credit advice. Bothsides is not a mortgage broker or credit provider.


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