Monkey Masters: John Pleasants



For my second interview of Monkey Masters, I am thrilled to interview John Pleasants. 

To say that John is a “silicon valley” rock star would be an understatement.  During his career, John has led several public and private companies and created billions in market capitalization.  He has worked with and served on Boards for remarkable companies such as Expedia, Ticketmaster, Playdom, Revolution Health and some bike company named Peloton.

In short, John has just about seen and done it all (full bio at the end of the interview).  More importantly, he is a great human, father, husband and all-around wonderful guy.  I hope you enjoy episode two of Monkey Masters!

Why did you decide to become an entrepreneur? What 1-2 things from your life, your upbringing or professional experience drove you to eventually take the plunge into the great unknown?

I have always had the greatest respect for those who took the chances, who believed in their talents, who did not fear failure and set off with passion and conviction to change the status quo for the better. I wanted to take a swing at that level of creation and contribute myself.

What mental hurdles held you back and how did that manifest itself in your leadership/decision-making/personal well-being? 

Instilled/traditional paradigms of success. Fear of failure/lack of confidence, the pull of perceived security and responsibility VS adventure into the unknown and ego attachment to success in hand. 

What one piece of advice would you give to your previous self when you were first starting out?

Try to know who you really are and develop yourself to the fullest (which is no easy task), then play the song of life to the melody of your choosing. 

What was the biggest surprise for you about being an entrepreneur?  What do you know now that you wished you then?

The highs are high and the lows are really low. Remember the throughline, the reason you took the journey. There is no fail, only learning to be reapplied. Stay curious, stay creative, and stay gritty. Always be empathetic and kind to those around you… they have their challenges just like you. Stay connected to the cause, the present, and those with you. You will expand into success and love no matter the outcome – which will invariably differ from what you imagined. What a joyous trip it can be if you enable it to be so – that is in your control – 100%.

Who are your entrepreneurial (or life) heroes?

Richard Branson, Bono, and Sataoshi Nakamoto

I have a voice in my head that fills me with fear, uncertainty and doubt. I call him Mr. Monkey.  Do you have a voice like him? How does he try and screw with you? How do you quiet him (or her or it) down?

Mr. Monkey is always there. My goal is not to kill or hurt him… but to take his input for what it is but not be beholden to it. Listen to him, find the pearls, integrate appropriately on your team, then give him a banana and tell him to sit in the corner and watch the show 🙂


A huge thank you to John for participating in Monkey Masters! Be sure to to be on the lookout for my next interview and all future blogs here

AND if you haven’t yet… be sure to take The Entrepreneur Survival Test and test your skills. 

John Pleasants is a high-tech internet executive that has consistently led public and private companies to $ billions in market capitalization gains over the past 20 years. As a CEO and President, Pleasants has built and run start-ups as well as divisions of worldwide media, Internet and hardware conglomerates. In these consumer-facing businesses, some with significant enterprise customers and strategies, he has scaled business models in e-commerce transactions, subscriptions, advertising, content / service purchases and in-app transactions. Pleasants has overseen the acquisitions, mergers and integrations of 35 companies totaling ~$1.5 billion across all forms of gaming, global live event ticketing, online dating, local services and consumer-driven healthcare.

Pleasants has served on the board of three public companies: Expedia

(NASDAQ: EXPE), Ticketmaster (NASDAQ: TMCS) and the Leaf Group (NYSE: LEAF); and over a dozen private companies including: Peloton (NASDAQ: PTON), Playdom, Revolution Health, Ticketmaster-Online Citysearch, (NASDAQ: ACTV), Fastclick, The Artists Den, ScoreBig, Trebel Music, The Entertainment Software Association (ESA) and Saatchi Art Online. He is an advisor to Spark Labs Global Ventures, Scalefast, Big Box VR, Lolly, Ossix / 2U money, and The Leadership Now Project. He also actively invests in consumer-facing start-ups and political reform and philanthropic entities.


Monkey Masters: Jason Dorsey

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