Reboot Podcast Episode #58 – The Joy of Surrender – with Simon Cant

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

Episode 58 // April 6, 2017


Simon Cant

Simon Cant

Managing Partner at Reinventure

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Episode Description

Simon Cant’s path to becoming a VC has been a windy road. Building on a career that includes stints as a lawyer, founder, consultant, director of a non-profit and advisor. Alongside his meandering career path, Simon has battled to slow the swing between a strong desire to exert control and an acute awareness of his own need to surrender.

In this conversation, Jerry leads Simon to remember that there is no such thing as a perfect surrender. That instead, surrender is a lifelong practice.

Simon Cant on TwitterGrace, VC & Surrender

Show Highlights

Top Quotes

“The dark side of wishing to heal the world is a wish to control the world.” – @jerrycolonna

“Here am I sort of telling corporates about their control instinct and you know, the journey that I’ve been on, is coming to terms with my own control instincts.” – @simoncant

“[In VC] you don’t actually know firstly, whether you’re doing a good job or whether you’re doing a terrible job.” – @simoncant

“My experiences that what serves founders best, is actually when you can really hold a vision for how they can be at their best.” – @simoncant

“The gift of surrender becomes the joy of surrender.” – @jerrycolonna

“It’s painful to look in that mirror.” – @jerrycolonna

“If you try as a funder, to sort of stand outside of the pit and pretend that you aren’t going to get hits by any of the mud that’s been flown, you’re kidding yourself.” – @simoncant

“I’m just trying to retroactively go back in time and save my 38-year-old self, from the pain that I suffered.” – @jerrycolonna

“I’m a mess and it’s okay. I’m great and it’s okay. “- @jerrycolonna

“One moment of wakefulness is worth a year of sleepfulness.”- Buddhist proverb

“We don’t practice awareness so that we’re aware constantly. We practice awareness so that we can come back to it, again and again.” – @jerrycolonna

“The best sales person is real.” – @jerrycolonna

Key Takeaways

Simon Cant is a partner with a VC fund in Australia, called Reinventure, a $100 million fund, investing in FinTec.

Simon has had a winding career path over the last 15 years including stints as a lawyer, founder, consultant, director of a non-profit and advisor. Along the way, he has noticed a pattern of tightening up (control) and loosening and tightening and loosening. He speaks to this in his Medium piece, “Grace, VC, and Surrender.”

Jerry shares that the dark side of wishing to heal the world is a wish to control the world. It’s the idea of wanting to control for a benevolent reason. Simon agrees and mentions that this realization is humorous to him as he often consulted to corporates to ease up on companies in which they had invested in while struggling to relinquish control himself.

VC is a hard enterprise to understand if you have been or are being successful, as the timeline for returns can be ten years or more. Simon shares that he takes on the stress of this uncertainty, not only for his own investment, but also the founders.

Jerry points out that this need to control and take on things is a reaction to fear, a fear of failure. And taking an attitude of “I’ve done everything I can do” (i.e. control) is a part of a longstanding pattern of tightness and control Simon has shared about. Simon mirrors that this is true and that the letting go really doesn’t just happen, it’s an active decision.

This process of actively letting go is the moment Jerry identifies as where the gift of surrender becomes the joy of surrender.

Part of the reason many people do not undergo a practice of radical self-inquiry is because it is often painful and they are unwilling to experience the pain.

Simon brings up that there exists a lot of inauthenticity in business. The “we’re crushing it” response to everything, when that is rarely the case, and that it can be a struggle to bring relationships to that authenticity, particularly in VC.

Jerry shares that people often ask him why is choosing to work in the VC and startup world. He shares that his first response is that he is “trying to retroactively go back in time and save my 38-year-old self, from the pain that I suffered.” He believes strongly in trying to pull others to a place of authenticity, and that Reboot’s work with this community uniquely positions them to impact many people.

Speaking further to authenticity, Jerry shares that “there’s a joy, even within the pain of living in a way in which your inner side, your inside matches the outside.”

Simon shares his personal experience that he tries to practice authenticity, but that he finds it challenging, particularly in the role of sales.

Jerry reminds Simon to first and foremost be gentle with himself and not judge his success by perfection, but rather to adopt the Buddhist principle that one moment of wakefulness, is worth a year of sleepfulness.

With regards to sales, Jerry reminds Simon of the warrior stance: a strong back and open heart. Just like the warrior stance has both a strong back and an open heart, a good investor can be sales-y and authentic.

Simon connects the experience of doing sales well to his experience of performing music. There is beauty in both. Like sales, Jerry reminds Simon that there are musical performances that are shallow, superficial and meaningless and there are performances that break your heart open. Both are performances, but one marries that authentic presence and heart. This is possible in sales (or VC) as well.