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Why Most Startups Fail And How To Prevent It with Jack Delosa

28 minutes

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From 100 hour weeks in business to building long-lasting success

Tell us if this sounds familiar. Entrepreneur starts business. Entrepreneur has strong intuition and passion to get it off the ground. Business starts growing. Entrepreneur starts doing everything, working 80, 90, 100 hour weeks. Entrepreneur feels stuck and worries they're falling out of love with their business. What should they do?
This is one of the most common experiences we see at The Entourage. Whether the business owner has reached their absolute capacity or are just starting to feel the struggle a bit too much, it's important to take a step back and understand exactly what is happening and why.
That's why we asked our Founder and 5x AFR Young Rich Lister, Jack Delosa, to come on this episode of The Make It Happen Show to teach you exactly how you can go from this reactive and chaotic startup to a business that can run without you always being there.
If you want to start building a business that can actually scale beyond you, this is the episode for you.

Topics covered in this episode:

  • 1:16 - Introducing Jack Delosa
  • 2:44 - How the journey of an entrepreneur is nearly always the same
  • 3:55 - Why so many business owners feel trapped by their business
  • 5:41 - The paradigm shift that every business owner needs to understand
  • 6:50 - The #1 misconception people have about being an entrepreneur
  • 8:01 - Why being in a startup is a terrible place to stay in long-term
  • 8:48 - The 4 hats that every single business owner wears
  • 11:48 - How to stop being the bottleneck and gain more freedom in your business
  • 14:48 - The top strategy to avoiding burnout while increasing business growth
  • 18:28 - The core barrier that prevents startups from improving their marketing
  • 20:55 - Systemising the main part of your business that generates revenue
  • 22:52 - If you do this one thing, you don't have a business, you have a job
  • 23:22 - The last 3 fundamental elements to a successful business


In this episode, you will learn:

  • What the role of the business owner is meant to be
  • The common challenges that arise as a business grows
  • The #1 shift you need to succeed in business
  • The 6 core elements to business
  • Why structure in business will give you leverage for more freedom
  • And more!
Headshot of Jack Delosa, Founer of The Entourage on The Make It Happen Show

"We often go into business in search of freedom but what happens is the larger the business grows, the more it serves to inhibit our freedom. "

— Jack Delosa




Great insight for business owners and super practical takeaways!

Bruce Casanovic

Amazing guests, great insights into their journey and what has helped make their businesses successful. Great to hear how some of the guests have navigated challenge as well. Loads of good practice takeaways.

Perfect for the Monday commute


Great to listen to on the commute to work on Monday mornings. Great content, well delivered and plenty of insights from industry leaders in a variety of fields. Good to see the entourage getting out there with a podcast series

Top-shelf guests. Top-shelf conversations.


This is so awesome, so helpful, and so fresh. Right from the get-go, the team at The Entourage have brought out the big names in the Aussie entrepreneur and business space to have conversations that every business owner should listen to. I can't wait to see who they bring on next.

Amazing guests


Loved the episode with Tim Fung, Airtasker CEO! You guys are getting some awesome guests in! Thank you!

Entourage on point again!

Adz Rodger

Great content again from The Entourage! Particularly like the 1st episode and the points Tim Fung made about making sure you make time to map out the future and don't get stuck on day to day 'work', as well as the observation that you really need to be strategic about your people management and not just try to save money. Two awesome take homes I have already taken action on!

For entrepreneurs and non-trepeneurs alike


Well this was one of the best things I’ve heard in a while. I’m by no means the target demographic, having zero business or entrepreneurial experience at all. Luckily the advice given for business growth and success is remarkably applicable to personal growth and success. Loved the conversational style, by the end of the podcast I felt like I knew both Tims personally, which is a great mark of engagement. And I loved hearing about the humble beginnings of Airtasker from the founder himself. Give this a listen if you’re craving a bit of personal or professional inspiration.


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