225: The Secret That Makes Teams Never Quit on You | Aaron Vaccaro
Release Date:Β
October 7, 2025
Release Date: Oct 7
Leadership isnβt about the titleβitβs 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 Topgolfβs 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 itβs 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 trustβwhether you have a title or not.
What Youβll Learn:
Why outcome over ego separates outstanding leaders from the rest
How to navigate imposter syndromeβand why vulnerability still matters in leadership
What 51/49 hiring means: Putting culture above skills for lasting success
Aaronβs 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
In This Episode:
00:00 β Why influence, not titles, defines real leadership
01:13 β Learning to put outcome over ego in crisis and growth
05:41 β Meeting a mentor (and how trust is built for the long-term)
07:01 β Navigating imposter syndrome and getting over self-doubt
09:09 β How relentless vision (and smart negotiation) turned Topgolf into a giant
14:48 β Scaling culture: The power of hiring 51% on values
18:03 β Tactics to embed core values beyond a poster on the wall
22:08 β Rising into the presidentβs seat at Singularity University
25:10 β Leadership is influence, not control (and how to lead without a title)
28:54 β Embracing tough conversations: Grace, truth, and feedback
33:16 β Setting new leaders up for success (and how to onboard well)
35:37 β βDeep learningβ as a shortcut to experience
38:28 β Aaronβs top three leadership books for new managers
40:52 β Finding time to read and keep learning as a senior leader
42:27 β Discipline, identity, and doing what needs to be done
46:09 β Defining your leadership identity after sports or big transitions
47:47 β Becoming the kind of leader people truly donβt want to let down
50:39 β Leadership mistakes: Lessons from tough meetings and letting things fester
54:37 β Balancing grace, truthβand knowing when itβs time to part ways
56:38 β Trusting again after being let down as a leader
58:53 β Why Aaron looks up to Winston Churchill
60:39 β The importance of mentoring, giving back, and keeping it cool to care
62:05 β Final takeaway: Make it cool to careβin 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 Topgolfβs 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 Andersonβs 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.
