Leadership isn’t about the title—it’s about the courage to care, the power of vision, and the ability to influence without control. 

In this thought-provoking episode, Damon sits down with Aaron Vaccaro, President of Singularity University and a key architect behind Topgolf’s explosive growth, to unpack the mindset and methods that turn good leaders into great ones. Aaron shares lessons from the frontlines of scaling billion-dollar visions, battling imposter syndrome, and building cultures where it’s actually cool to care. From navigating chaotic turnarounds to learning how to truly let go of ego, this episode delivers actionable insights and candid stories for leaders at every stage of their journey. 

Tune in for practical wisdom, leadership book recommendations, and the real secrets to earning trust—whether you have a title or not. 

In this episode, you’ll learn: 

• Why outcome over ego separates outstanding leaders from the rest 
• How to navigate imposter syndrome—and why vulnerability still matters in leadership 
• What 51/49 hiring means: Putting culture above skills for lasting success 
• Aaron’s playbook for building (and maintaining) a values-driven culture 
• The difference between leadership by control and leadership by influence 
• How deep learning, not just experience, can accelerate your leadership journey 

Timestamps: 

00:00 – Why influence, not titles, defines real leadership 

01:13 – Learning to put outcome over ego in crisis and growth 

05:41 – Meeting a mentor (and how trust is built for the long-term) 

07:01 – Navigating imposter syndrome and getting over self-doubt 

09:09 – How relentless vision (and smart negotiation) turned Topgolf into a giant 

14:48 – Scaling culture: The power of hiring 51% on values 

18:03 – Tactics to embed core values beyond a poster on the wall 

22:08 – Rising into the president’s seat at Singularity University 

25:10 – Leadership is influence, not control (and how to lead without a title) 

28:54 – Embracing tough conversations: Grace, truth, and feedback 

33:16 – Setting new leaders up for success (and how to onboard well) 

35:37 – “Deep learning” as a shortcut to experience 

38:28 – Aaron’s top three leadership books for new managers 

40:52 – Finding time to read and keep learning as a senior leader 

42:27 – Discipline, identity, and doing what needs to be done 

46:09 – Defining your leadership identity after sports or big transitions 

47:47 – Becoming the kind of leader people truly don’t want to let down 

50:39 – Leadership mistakes: Lessons from tough meetings and letting things fester 

54:37 – Balancing grace, truth—and knowing when it’s time to part ways 

56:38 – Trusting again after being let down as a leader 

58:53 – Why Aaron looks up to Winston Churchill 

60:39 – The importance of mentoring, giving back, and keeping it cool to care 

62:05 – Final takeaway: Make it cool to care—in your culture and your life 

About Aaron Vaccaro 

Aaron Vaccaro is the President of Singularity University and has been instrumental in scaling high-growth ventures, notably Topgolf’s rise as a global brand. Known for orchestrating successful turnarounds and helping companies live their core values, Aaron has led strategic acquisitions, built innovative cultures, and mentored teams to think bigger and bolder. With roots as Eric Anderson’s chief of staff and an impressive trajectory through multiple leadership roles before 35, Aaron brings a rare blend of humility, vision, and operational grit to every team he leads. 

Resources & Mentions 

• Connect with Aaron Vaccaro on LinkedIn 
• Learn about Singularity University 
• Canoeing the Mountains by Tod Bolsinger 
• Atomic Habits by James Clear 

Podcast Contact Information: 

Website: www.learnit.com 

Email: podcast@learnit.com 

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