VVSEAI Event | Hard Truths by Vertex with Jack Selby, Member of PayPal Mafia (Singapore)

Jedidiah Asaf | 29 Jan 2024

Hard Truths by Vertex with Jack Selby, Member of PayPal Mafia(Singapore)

By Jedidiah Asaf Tallulembang

“What would digital payments and fintech look like today, if PayPal didn’t exist?”


That question was on my mind as I adjusted my camera, focusing on our speaker, Jack Selby, as he addressed our audience at the recent fireside chat event “Hard Truths by Vertex with Jack Selby” held at Vertex Ventures Southeast Asia & India’s Singapore office on 16 Jan 2024. Jack Selby is a member of the PayPal Mafia and the current Managing Director at Thiel Capital. During the hour-long conversation in front of more than 120 founders, investors and partners in the audience, we were hanging onto every word that Jack shared – valuable perspectives on crucial topics ranging from innovation to leadership. In this post-event recap, it is my pleasure to share the key highlights and takeaways that captured the essence of the discussion. Interested in watching the live recording? Tune in to the YouTube

About Jack Selby


Jack Selby looks tall in his video interviews that I scoured on the web. As I saw him entering the town hall of Vertex Ventures Southeast Asia & India’s Singapore office in the flesh, he is easily one head taller than the average person in Singapore. There is also this aura and presence to this man that you would see often on celebrities and accomplished individuals. Though Jack Selby has had a notable career in the technology industry, he is extremely humble too (you would probably agree if you see him that day or on the live recording). At the age of 24, Jack started as employee number 9 at PayPal where he held the position of Senior Vice President for Corporate/ International Development and played a significant role in the company's early development. Currently, he serves as the Managing Director of Thiel Capital, Peter Thiel's Family Office. In addition, Jack also founded an early-stage fund, AZ-VC, Arizona's largest venture capital fund. Jack’s extensive knowledge and experience in the technology ecosystem have earned him a reputation as a seasoned professional in the field.


Why Singapore?

Continuing from there, Jack Selby walked us through a behind-the-scenes journey of PayPal's early days, emphasizing useful learnings in the decision-making process that led to the company's success. Despite facing numerous challenges during the late 1990s and early 2000s, such as the dot-com bubble crash and the 2008 financial crisis, it’s remarkable how PayPal managed to navigate without a ‘playbook’ and yet achieved significant outcomes. Jack’s perspective provided a unique glimpse into the resilient and strategic thinking that propelled PayPal forward.

To our delight, Jack also gave us a fascinating look into PayPal's origins. He explained how the merger between Confinity and Elon Musk's X.com led to the birth of PayPal. Recounting the complexities of this collaboration, as well as his informative yet humble storytelling style allowed attendees to understand the intricate dynamics that set the stage for PayPal's transformative journey.

Entrepreneurship is about the fit, not for the faint of heart

"Today, everybody wanted to be an entrepreneur; however, it became so overblown almost like a game show," - Jack Selby


In today's world, entrepreneurship has become a buzzword that everyone seems to be chasing after. But the reality is far from what meets the eye. It's not as easy as flipping your palm and achieving success overnight. It takes hard work, dedication and perseverance to make it as an entrepreneur.


"Jack summarised it well when he reminded us that the life of an entrepreneur is not an escalator, but a roller coaster. I was reminded that while experienced founders have a couple more layers of grit and should be able to hunker down during tough times, these are nevertheless challenging fundraising times. Entrepreneurs must also care deeply about the macroeconomic environment and make educated, pivotal, even existential decisions for the business. This is a reminder for me to choose my business model with my eyes open and not assume that the headwinds will magically turn tail…“ shared by one of our attendees,

Lee Junxian, Jonah, cofounder and Chief Product Officer, GoodWhale


“Hold onto relationships that are beneficial. At PayPal, Jack worked closely with Peter Thiel and Elon Musk, and self-deprecatingly describes himself as "the dumbest guy in the room" (to laughter from the audience). Jack was only 24 when he met Peter Thiel, and their serendipitous meeting changed his life. Jack's advice to the audience is to do everything they can to hold onto beneficial relationships.”  shared by one of our attendees,

Joel Shen, Partner, Withers Tech Asia


Jack emphasized that not everyone is cut out for entrepreneurship, and it requires a special “temperament” and a lot of resilience. For me, or anyone considering entrepreneurship, we are reminded that it is not for the faint-hearted and demands a high degree of tenacity.

"Success in entrepreneurship requires equal parts grit and grandiosity. You're in for a challenging journey, so might as well aim for the stars.” - Jack Selby


What does he think of AI, Artificial Intelligence?

“AI is evolving into a staple ingredient for startups, enhancing efficiency in routine tasks and becoming integral to their success” -Jack Selby


As the event was approaching its end, Jack shared his thoughts on the upcoming trends for 2024. He pointed out the growing number of AI-related businesses and predicted that AI could soon become a ubiquitous ingredient for startups worldwide. Jack also emphasized the proven benefits of AI in improving efficiency for various industries, including startups. However, he also warned about the need to think big when considering investments in this area. The importance of a forward-thinking and expansive approach, acknowledging the balance between opportunity and risk in the dynamic landscape of AI is highly needed.

Behind that successful investor, Jack is also a big fan of independent movies. In fact, since he is also a film producer, maybe that’s why he is so good at storytelling. At the end of the event,  Jack gave the audience much food for thought when he drew the parallel between filmmaking and investing. Both businesses are tough, but the ceiling for positive outcomes is lower in independent filmmaking. Despite this, Jack still loves the art of filmmaking and wants to be a part of the independent industry.

"Jack answered questions with aplomb. I was especially impressed with his response to an unflattering question, which he freely admitted he had never heard before! " shared by one of our attendees,

Murli, Managing Partner, Tin Men Capital

My own takeway

During my current internship with Vertex and my previous one at an investment-related company, I met a lot of people who believed that the venture capital industry is very niche and doesn't offer much room for development beyond honing technical skills such as financial analysis and research. But for me, I realised that it's the complete opposite of the truth. At our last event in December, "From First $1 M in Funding to First $1 M in MRR," and now with Jack Selby's insights, I've come to appreciate that the investment industry and entrepreneurship offer more than just training in technical skills. I have personally derived many philosophical life lessons from these experienced investors and entrepreneurs. In my view after receiving insight from these people, I believe that entrepreneurship is more than just a business; it's a process of life.

About Jedidiah Asaf Tallulembang

I’m a current intern at Vertex Ventures Southeast Asia & India, with the Communications and Community team. Prior to this, I completed an IT security internship at MDI Ventures, the venture arm of Telkom Indonesia. I'm pursuing my degree in Computer Science in Cybersecurity, at the University of Wollongong. Outside of school and work, I’m a content creator on TikTok, commenting on trending Gen Z topics such as social issues in Bahasa Indonesia, you can find my profile at @ketutuptopi.

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