What if a stranger who had no idea what you did decided to introduce you anyway, purely on a feeling? In this episode, Aaron Vaccaro, President of Singularity University and Managing Director at West River Group, shares how a lunch he asked for in a college cafeteria led to a five minute phone call that shaped his entire career. Aaron helped take Topgolf from $90 million to over a billion in revenue as chief of staff to the CEO. He now leads the organization he first heard about on a podcast in college, teaching executives, governments, and militaries how to think clearly about AI and frontier technology. This conversation covers why most companies grab the wrong tool, and why the man who introduced him to his mentor did not even know what business the guy was in. [00:04:55] What He Does and Who He Serves President of Singularity University, where he has been for three years Founded almost 20 years ago by Peter Diamandis and Ray Kurzweil Delivers executive education for corporate, government, nonprofit, and military leaders Covers 17 technology areas including AI, quantum, biotech, and space [00:06:35] What Inspired Him Originally First heard about Singularity on a podcast in college in 2012 The insight was that leaders learn finance and strategy but not frontier technology The goal was teaching the best and brightest to solve global grand challenges Not building another app, but building companies that address hunger, water, and poverty [00:08:16] Why the Idea Fit Him Perfectly Was a physics then math major who also ran an investing club Originally wanted to study nuclear energy Loved entrepreneurship and the power of science to make breakthroughs Singularity seemed to combine both into the best of all possible worlds [00:08:40] From Investor to President Joined venture capital firm West River Group straight out of college Years later Singularity came across their desk raising capital At about 25 he pushed the firm to invest because he already knew the organization After the pandemic restructuring, West River became majority owner and he was drafted to lead [00:10:00] What Inspires Him Now Technology can create as many problems as it solves if not guided well Points to social media, misinformation, and cheaper fossil fuel extraction Still believes in the possibility technology creates Now focused on helping leaders implement it wisely and avoid leaving people behind [00:12:30] The Surreal Part Read Bold, Abundance, and The Singularity in college and saw the authors as celebrities Those same people are now on his speed dial and on the board he reports to Compares it to a Lakers fan ending up working in the front office Twenty-two year old Aaron would not have believed the path was possible [00:14:00] Why He Got Those Opportunities Every organization needs people willing to show up and run things Sometimes it is as simple as raising your hand and saying you care He volunteered for investments, capital raising, financial modeling, and the COVID restructuring He was learning most of it for the first time but was willing to do it [00:15:45] Be Genuinely Nice If you are smart, willing to solve problems, and people like working with you, it is not complicated Authenticity comes through, especially online where anyone can position themselves as anything People sniff out authenticity quickly Better to actually care about people than to perform caring [00:16:51] Client Impact: Bringing Executives to Silicon Valley Brings executive teams from the US, Spain, London, and Chile to the Bay Area Combines lectures and workshops with visits to Nvidia, Amazon, Microsoft, and startups First goal is awareness of what is actually happening on the cutting edge Second goal is foundational understanding of what these technologies can and cannot do [00:20:17] Start With the Problem, Not the Tool When you have a hammer, every problem looks like a nail AI is the big shiny hammer right now First figure out whether you are dealing with a nail, a screw, or a staple Use a hammer on a screw and you will get there, but you will damage a lot on the way [00:21:37] The UK Financial Firm Brought their entire executive team out for a few days Paired them with startups building agents for wealth managers The CEO believed they would be gone in five or ten years without change His leadership team believed everything was fine, so he brought them to be shaken up [00:23:31] Culture Change Down the Layers Now building an education program for the entire company The culture has both resistance to change and a lack of awareness Teaching principles of exponential change and how to look ahead With exponential technology you cannot know exactly where the puck is going [00:25:36] Ask What Is Not Going to Change Borrows a framework from Jeff Bezos Amazon assumed customers would always want better selection, fast delivery, and low prices No future customer will ask for slower delivery or less selection Optimize for the constants and let everything else evolve [00:28:12] Why Foresight Stays Flat Change accelerates every year on an exponential curve But at any point on that curve, our forward view remains linear People recognize the pattern behind them and still fail to project it forward We overestimate one year and underestimate ten [00:29:22] The Opposite Problem: The AI Happy CEO Working with an energy company whose new CEO is gung ho on AI They invested in an AI startup without knowing what they would do with it The incoming head of technology brought Singularity in to separate hype from noise The energy and willpower are there; it just needs direction [00:31:41] Building the Scariest Program Possible Works with branches of different militaries focused primarily on risk Technology companies now rival or exceed governments in cybersecurity capability He could build a program that leaves you optimistic or one that terrifies you For national security clients, he deliberately builds the frightening one [00:33:50] The $1.3 Million Phishing Scam A friend's business lost $1.3 million to social engineering Their bookkeeper was convinced the callers were the FBI and Treasury Department Money was wired out through a fraudulent account They recovered roughly $400,000 through the bank and FDIC [00:37:02] The Relationship That Changed Everything: Eric Anderson Aaron asked a university board member to lunch during his senior year That man said he knew an investor in Seattle but did not know what he did He made the introduction purely on a feeling that they would get along That investor was Eric Anderson, founder of West River Group [00:39:12] Five Minutes in the College Library The first call lasted less than five minutes Eric asked directly whether he needed money, a job, or an internship Aaron said an internship and Eric said come work with me this summer Two weeks later someone called to arrange it [00:40:44] The Call That Turned Into a Career After the summer he went to a master's program and was recruiting elsewhere Eric called in October offering a job as his right-hand man He had taken over Topgolf as CEO after a major investment Aaron worked part-time until graduation, then joined full-time in Seattle [00:41:50] From $90 Million to Over a Billion Served as chief of staff for about six years Covered finance, strategy, operations, and growth Topgolf grew from $90 million in revenue to just over $1.1 billion before being sold to Callaway Eric gave him agency to make mistakes, join boards, and get his hands dirty [00:43:00] Luck Paired with Work Says the people who influenced him most are his parents and then Eric They still speak nearly every day Calls it a crazy lucky break of meeting the right person at the right time But he worked 60 to 80 hour weeks for five-plus years to take advantage of it [00:44:47] Final Word: Step Away From the Chat Window There is enormous pressure to be on top of every new AI tool You will never keep up, and he calls that pressure total crap Tools are a means to an end, not the end themselves Go touch some grass, read a physical book, and think about the problem you are actually solving KEY QUOTES "We should be teaching the world's best and brightest not to be building apps like Twitter, but instead building companies that leverage these technologies to solve bigger problems in the world." - Aaron Vaccaro "Technology has the capacity to create as many problems as it solves if not implemented or guided correctly." - Aaron Vaccaro "When you have a hammer, every problem looks like a nail, and right now we have this big shiny hammer in AI." - Aaron Vaccaro CONNECT WITH AARON VACCARO Website: https://www.su.org LinkedIn: https://www.linkedin.com/in/aaronvaccaro Thanks for tuning in! 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