The Optionality Game

On this episode of The Optionality Game, we were honored to interview Arun Rao. Arun leads Meta's core machine learning and artificial intelligence team, overseeing more than 200 engineers to tackle some of the thorniest AI issues while impacting the online experience of almost 3 billion people every day. He is also a professor, author, and an avid reader. 

During the interview, we discuss: 

- Arun's career journey through finance, startups, and big tech

- The past, present, and future of artificial intelligence

- Crypto, web3, and the metaverse 

Alfston and I hope that you enjoy this episode as much as we enjoyed recording it. As always, let us know about any questions, comments, or suggestions. 

As we continuously explore new formats for The Optionality Game, we're launching a special segment called Future Focus. In these episodes, we're still interviewing successful businesspeople, but focusing more on the guest's expertise and less on their personal background. 

Our guest today is Nick Adams, a co-founder and managing partner at Differential Ventures. We chat about the definition of AI, Nick's skepticism of some AI concepts, AI's effect on employment, which jobs cannot be automated, and existential risk from AI. 

We also hear about Nick's journey from a history major and law school to the world of venture capital and some investments along the way!

We hope you enjoy this conversation as much as we did. As always, please let us know about any feedback or suggestions. 

In the ninth episode of the podcast, we chat with Larry Paul, the Managing Partner of Laurel Crown Partners and owner of the Pittsburgh Steelers. Larry has certainly taken the path less traveled, initially completing Harvard Medical School before pursuing a career on wall street. By successfully drawing parallels between his vastly different experiences, Larry has excelled in the fields of investment banking, private equity, and philanthropy. 

Please enjoy our conversation and let us know about any questions, comments, or suggestions!

In the eighth episode of the podcast, we chat with the CMO of Axonius, a unicorn and one of the world's fastest growing cybersecurity companies. Nathan completed his undergraduate degree at Northeastern and went on to lead marketing efforts at wildly successful SaaS startups including CloudLock, Intralinks, and Hexadite. Now, Nathan is on a mission for Axonius to become the fastest cybersecurity company to reach $100m ARR. We learn about Nathan's approach to mentorship, philanthropy, and how his strong conviction in the company has led him to the unexpected. 

Please enjoy our conversation and let us know about any questions, comments, or suggestions!

In the seventh episode of the podcast, we chat with private equity veteran Larry Lavine. Larry completed his undergraduate degree at Northeastern before becoming a Baker Scholar at Harvard Business School. Then, he began his career in investment banking in the seventies. He climbed the ranks and eventually became a Senior Managing Director at Ripplewood Holdings, an interesting and reclusive $10 billion private equity fund. 

After a series of episodes on tech founders and VCs, Larry is at the other end of the spectrum as a quintessential Wall Street financier. He is also a personal friend and mentor to Alfston and Cooper, and we've been looking forward to recording his famous anecdotes on the Optionality Game. 

Please enjoy our conversation and let us know about any questions, comments, or suggestions! 

In our sixth episode, our guest is Elissa Couglin, the Director of Platform & Strategic Partnerships at Unity Technologies. She is a jack-of-all-trades, filling a variety of roles in companies from IBM to Vanity Fair to Google. We chat about culture at tech firms, the applications of Unity's technology, and Elissa's journey to find herself in her career. 

We hope you enjoy this conversation as much as we did! Please let us know any comments or questions. 

In our sixth episode, we chat with Nathan Burke, the CMO of Axonius, a cybersecurity asset management platform that recently raised $100m at a $1.2 billion valuation. Two of the past companies he led marketing efforts for, Cloudlock and Hexadite, were acquired by Cisco and Microsoft. We learn about how Nathan got his start in marketing, thinks about building teams, and maintaining a competitive edge. Nathan has a wealth of knowledge in both cybersecurity and marketing and is one of the most passionate entrepreneurs we have talked to. 

In our fifth episode we chat with Ron Jones, the founder of Bungee America and one of the creators of the sport, Bungee Jumping. Ron has lived several lives as we learn about his experience as one of the youngest competitors in the Iron Man Triathlon (16:00), becoming a chiropractor while going to school on a bull riding scholarship (24:00) and his first time ever Bungee Jumping (32:00). After trying various careers, Ron had finally been able to combine his passion with helping others conquer their biggest fears. We hope you enjoy this conversation as much as we did! If you are ever in Los Angeles, we highly recommend visiting Ron and his team in the Angeles National Forest.

In our fourth episode, we chat with Michael Gasiorek, a man with a LinkedIn as long as a CVS receipt. He is currently Head of Growth at TrustToken and the CEO/founder of Truth Cartel. 

We discuss his journey from Poland to Silicon Valley, the definition of a tribe (around 21:00), and one's ability to learn empathy (around 40:30). 

Tune in every other Friday for episodes with one of the first bungee jumpers, the CMO of a cybersecurity unicorn, and many others! 

In our third episode, we have a conversation with Jason Corwin, the founder of Safely Finance, a startup that finances your apartment's security deposit. 

We discuss his journey from firefighter to founder, going through Y-Combinator twice, and founding a company as a father. 

Tune in every other Friday for new episodes with founders, investors, thought leaders, and everyone in between.