Episode 105

Who Dares Wins with Ollie Ollerton | Win the Day® podcast
September 20, 2022
Ollie Ollerton is a UK Special Forces operative, four-time bestselling author, and star of hit television series’ 'SAS: Who Dares Wins' and 'SAS Australia'.
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In this episode of Win the Day:

Heard of 007?

Well, today we get to sit down with a real life ‘00’.

Ollie Ollerton is a UK Special Forces operative, four-time bestselling author, and star of hit television series’ SAS: Who Dares Wins and SAS Australia.

Ollie’s military career began at the age of 18 when he joined the Royal Marine Commandos and toured operationally in Northern Ireland and Iraq for Operation Desert Storm. After five years as a Commando, Ollie was recommended for SAS Special Forces Selection. Only a handful of the 250 candidates made it through the grueling six-month selection process.

Ollie then spent six years in the Special Boat Service – the SBS – where he undertook high profile missions in counter narcotics, counter terrorism, homeland security, and humanitarian work.

After leaving the special forces, Ollie held roles as a private security contractor in Iraq, project manager for major infrastructure projects in the Middle East (where he also trained a 2,000-strong Iraqi guard force), and as a bodyguard instructor for private projects and government officials. In addition, Ollie infiltrated child sex trafficking rings in southeast Asia.

Today, he is the founder of BreakPoint, where he provides leadership and development courses to the corporate and public sector that leverages the special forces mindset. Ollie is also the author of four critically-rated books and founder of supplement brand Battle Ready Fuel.

In this episode:

  • How he made it through the most grueling special forces selection in the world – twice;
  • The most impactful moments from his special forces career;
  • His best tips and exercises to apply in civilian life; and
  • How you can turn your breaking point into your biggest strength.

Let’s WIN THE DAY with Ollie Ollerton!


0:17 Who is Ollie Ollerton

2:36 Interview starts

3:05 The importance of who you’re around

5:00 Being attacked at 10 years old

8:28 Learning from adversity

9:35 How to be inspired in your own life

11:54 SAS selection process

19:49 Leadership of self in special forces

23:05 First operation with Special Boat Service (SBS)

24:03 SAS assault on Iranian Embassy

27:19 Why are the SAS so good

31:50 Common traits between special forces (Delta, SEALs, SAS, SBS, etc.)

34:01 Breathe - Recalibrate - Deliver

38:45 Why process is more important than motivation

44:15 How to figure out what your personal mission is

47:35 Processing atrocities of war

51:08 Feeling empathy for the enemy

53:35 Why special forces struggle in civilian life

55:59 Hitting rock bottom (thinking about suicide)

1:05:23 Knowing if someone has what it takes

1:09:13 Ollie’s affirmation

1:11:23 Rocket Round


Resources / links mentioned:

🎯 Download your FREE Win the Day action plan

Ollie Ollerton website

📷 Ollie Ollerton Instagram

🌎 BreakPoint website

🎙 BreakPoint Podcast

💪 Battle Ready Fuel Store

📚 ‘Break Point’ by Ollie Ollerton

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💚 Give the Win the Day podcast a 5-star rating on Apple Podcasts

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💕 Win the Day Facebook group

📝 Win the Day newsletter [weekly LinkedIn exclusive]

Inspiring quotes in this episode:
  • "If you look at the people that you surround yourself with, you should admire the qualities they possess." - Ollie Ollerton
  • "My most negative experiences is where I've grown the most." - Ollie Ollerton
  • "Your break point is a short-term step into discomfort for long-term gain." - Ollie Ollerton
  • "Nothing was ever great unless at some point you doubted your ability to achieve it." - Ollie Ollerton
  • "The brain gives up way before the body." - Ollie Ollerton
  • "Leadership is about leadership of self." - Ollie Ollerton
  • "Your mind is the best weapon you've got." - Ollie Ollerton
  • "Under great stress, recalibrate to: 1. Let go of all the things that don't matter in that moment; and 2. Focus on the 1-2 things that do." - Ollie Ollerton
  • "Process is much more powerful than motivation." - Ollie Ollerton
  • "No plan survives first contact. Progress towards a goal is never linear." - Ollie Ollerton
  • "If you can't expose your weaknesses, you can't do anything about them." - Ollie Ollerton
  • "Your power has to be the purpose of what you are doing." - Ollie Ollerton
  • "Pain screams the loudest when it's dying. It's the birth of something new." - Ollie Ollerton
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