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Fireside Chat with Jason Portnoy: Adding by Subtracting

Saturday Jan 21,2017

Tags :  fireside, chat, jason, portnoy


Adding by Subtracting? Here’s What You Can Learn From Jason Portnoy, Former PayPal Executive

On 15 Nov 2017, Jason Portnoy, currently managing partner of Oakhouse Partners and ex-VP of Finance at PayPal was invited by IIE for a fireside chat at Singapore Management University (SMU). Jason was an early employee of PayPal and was with the company through from its hyper-growth stage to its IPO and subsequent $1.5 billion dollar acquisition by eBay. On top of being the managing partner at Oakhouse Partners, he is also the founding partner of Subtraction Capital, a venture capital fund that invests in early-stage enterprise software companies. He graduated from the University of Colorado Boulder with a Bachelor’s degree in Chemical Engineering as well as Stanford University with a Master’s degree in Management Science and Engineering.

Working closely with CEOs and assisting with capital funding, team management and navigating through complex negotiations, Jason helps companies advance and scale through hyper-growth periods. With over 15 years of experience in the entrepreneurship landscape, Jason shared his experiences and tips throughout the years to young student entrepreneurs at SMU. For those interested in starting their own business or aspiring to become a successful venture capitalist, read on below for Jason’s tips!


  1. Personal Growth Is Equally Important
    Having a successful business is not just about the growth of the company. One of the keys to success from Jason’s point of view as an experienced venture capitalist, especially for a founding company, is that the company cannot grow faster than the CEO. Commitment to personal growth and building relations is one of the most crucial and essential career progression for an entrepreneur. With time, as you build good relations, set goals, develop your potential and talent, people will start to gravitate towards you and your ideas.


  1. Even When You’re Successful, Mentors Are Still Important
    Mentors are often associate with people early in the careers but that’s not always the case. Even as a successful venture capitalist with more than 15 years of experience under his belt, Jason believes that mentorship is a long-term and constant learning experience regardless of where you stand in life. Mentorship is not only restricted to personal, one-to-one coaching as well. It could be as simple as watching YouTube videos and listen to interviews with CEOs to learn and observe how they think and act. One of the most memorable mentorship experience for Jason was during his PayPal days, where he had incredible opportunities to attend meetings with investors and witness the pitching process for PayPal IPO. He described himself as a very lucky and privileged 25-year old back then and even though he was very young and green, he was always working hard, absorbing and listening to everything he could.


  1. Adding by Subtracting
    Jason introduced the concept of ‘Energy Curve’ during the fireside chat and described how we can utilise it to manage our careers. He often uses a scale of -5 to +5 to map out his energy level after every activity, with -5 being very unenthusiastic and +5 being very energized and eager. Gradually, he was able to observe clear patterns on the type of activities he preferred or the kind of people he enjoyed working with. Thereafter, he will begin to ‘subtract’ by eliminating activities or people that was causing his low energy. The reasoning behind the concept of ‘Energy Curve’ is that it really allows one to shift their focus and energy on things that they are really passionate about. This simple activity became a game changer for Jason as he was able to really concentrate on doing things he believed in. It is a perfect tool for entrepreneurs to really focus on their goals and not allow distractions get in their way.




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