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.
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
"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
Website: https://www.su.org
LinkedIn: https://www.linkedin.com/in/aaronvaccaro
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