Suggested questions

1You’ve spoken openly about achieving external success while internally struggling with loneliness and addiction. What finally made you realize something had to change?

2Why do you believe so many high-performing leaders silently suffer, even when they appear successful on the outside?

3In your experience, what’s the difference between being surrounded by people and actually feeling connected?

4What does “executive loneliness” really look like behind closed doors?

5You often talk about vulnerability as a leadership strength. Why do so many leaders still fear it?

6What happens to a leader - and a company culture - when people feel they must always appear strong?

7You’ve shared publicly about your hospitalization and recovery journey. Looking back now, what was the biggest lesson from that period of your life?

8What did rebuilding your life teach you about identity, purpose, and self-worth?

9How did sobriety change the way you lead, communicate, and build relationships?

10What would you say to executives or entrepreneurs who secretly feel burned out, lost, or emotionally exhausted?

11Was there a defining moment where you shifted from chasing success to pursuing meaning?

12You created the framework “Holistic Leadership.” What does that mean beyond the typical corporate definition of leadership?

13Why do you believe leadership today requires emotional fitness, not just professional competence?

14Your framework includes Surrender, Purpose, Connection, Goals, and Discipline. Which of these steps do leaders struggle with the most?

15How can leaders pursue high performance without sacrificing their mental health, relationships, or identity?

16What are some daily disciplines that have had the biggest impact on your wellbeing and performance?

17You speak frequently about modern masculinity. What conversations do men still avoid having?

18Why do you think vulnerability is still uncomfortable for many men in leadership positions?

19What role has your Men’s Group played in helping leaders open up and support one another?

20What are some warning signs that a leader may be struggling emotionally, even if they seem highly successful?

21How can organizations create psychological safety without it becoming just another corporate buzzword?

22You’re a top-performing Ironman athlete. How has endurance sport shaped your mindset in business and life?

23What parallels do you see between endurance racing and overcoming adversity in leadership?

24How do discipline and recovery work together in achieving sustainable high performance?

25Many people admire discipline, but few understand consistency. What keeps you committed on difficult days?

26You often ask people: “What is your purpose, and what legacy do you want to leave behind?” Why are those questions so important to you?

27What does living a “limitless life” actually mean to you today?

28If success alone doesn’t create fulfillment, what does?

29What kind of conversations do you hope leaders are having more openly five years from now?

30What is one truth about leadership that you wish more people understood earlier in life?

31What was your real rock bottom moment?

32Can successful leaders still feel deeply lonely?

33Why is vulnerability so difficult for executives?

34What does holistic leadership actually look like in practice?

35How do you balance ambition with wellbeing?

36What saved your life?

37What does masculinity mean to you today?

38Why do so many leaders struggle silently?

39How can leaders build genuine connection?

40What legacy are you trying to leave behind?