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Make it your business to know yourself, which is the most difficult lesson in the world.” – Miguel De Cervantes


On Monday morning earlier last week, my partner Jerry Colonna and I (in our role as Scale Coaches) met a group of entrepreneurs from the Upscale programme at the top of the Ace Hotel in Shoreditch for a discussion about the challenges of entrepreneurship and why resilience is a key element of leadership. The few moments of sunshine early that morning shone brilliantly on the room of CEOs and founders who gathered round for Jerry’s talk “Standing Still With Your Hair On Fire: The Challenges of Entrepreneurship. (Note: in case you missed it, you can check out Jerry’s talk from the 2013 Pioneers Conference for similar content.)

One of the first questions Jerry posed to the group was “Why did you start your company? Why do you do what you do?” In other words, why are you signing up for this emotional roller-coaster ride of entrepreneurship?

A brave soul opened up about why he was doing his current startup by saying: “I had a startup that I quit working on to do something safe: go back to school and get a salary. We had a good product then. Shortly after I quit, a competitor with a similar product that was not as good as ours was bought by Google. I know our product was better. I regret that I was so close and missed my chance. I want to do this again.”

“How do you feel sharing this to the group here today?” Jerry asked.

Upscale Jerry Colonna 3

With his hand on his chest and a slight tremble in his voice, the brave soul replied: “I feel very vulnerable.”

The room was quiet in the way rooms get when there’s attentive listening and empathy. Jerry looked at the man’s co-founder, who was sitting right next to him, and asked: “What do you think of this guy right now that he’s revealed that?” The man’s co-founder answered with solid conviction: “I’d walk through walls for him.”

Turning back to the whole group who showed up that morning, Jerry asked, “How many of you would work for this guy?” Everyone raised their hand with the sort of awe that comes when one recognises a strong leader.

We witness this happen repeatedly in our work. The moment a leader faces the heart of the challenge or what their work means to them, is a moment in which a leader can connect deeper with their purpose and the purpose of their company. While it’s often a vulnerable place, that connection is forged in the heart and is something that employees, customers or investors can get behind.

Later that day, I sat with a pair of co-founders in a one on one session. One of them asked, “Ok, what do you see most often? What do I need to watch out for?” I smiled. He wanted the checklist of things to do, read, know and have in place so they would be all set in the face of the uncertainty that is startup life. That list doesn’t exist, of course, except in a very general sense. No one has an antidote to uncertainty. What I find that does kill startups in big and small ways is a leader’s lack of willingness to grow authentically in their role.

So often we see entrepreneurs trying to fit into the startup mould, versus creating something out of the box. Fitting into something prescribed by the latest top ten list, or modelling your company after the hottest startup in the headlines leaves something to be desired. That something is what you would like, what you want to build, and how you want to build it. What values are you infusing in your organisation and why? What kind of company do you want to build? What kind of adult do you want to be? These questions come from a place within you and, likely, haven’t been written up in a blog post for mass consumption yet. Being an authentic leader means bringing all of you into your work, not leaving the best parts of you at the door.

Upscale Jerry Colonna

As a coaching company, we are with our clients as they go through a lot: fundraising, short runways, crucial hires, critical fires, building a top notch management team, managing board members, scaling challenges, co-founder conflict, etc. Each issue has it’s own nuances in each company context, and each challenge can be moved through with clarity and mindfulness. How someone is as a leader in the face of and through all that comes your way is key. These crucial moments are where true leadership emerges.

There are very real issues that leaders face in their startups. Being authentic through it all is a challenging and fulfilling practice. Challenging in that it will provoke some of your deepest fears and feelings. Fulfilling in that increasing your awareness of those feelings creates freedom for how you choose to respond to them.

How can you use the challenges inherent in startup and upscaling life to enhance your leadership and resiliency?

These are the questions our work at Reboot revolves around. My partners and I have identified an equation, what Jerry will often refer to as “the bet,” which guides all we do. That equation is ‘Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership + Greater Resiliency’. Reboot is a coaching company, yes. But more than that, Reboot exists as a container for us to do our work as humans. We believe that work can be the way we achieve our fullest selves.

Jerry Colonna

I invite you to explore your relationship to your work even further. Below are five topics that are important for the sake of your own well being and the well being of your company. I’ve paired each item below with a useful resource for further reading, discovery and reflection on your own leadership style. It’s a mix of practical skills + radical self inquiry + shared experiences.

Managing Co-founder Conflict

How’s your co-founder relationship? 65% of startups fail as a result of co-founder conflict. My partner Khalid Halim just released a 4 part series on co-founder conflict touching on the topics of How Conflicts between Co-founders can Kill Startups, The Founder Who Doesn’t Scale, Who Decides What, and The Forgotten Co-founder.

Connecting to Purpose

What kind of leader do you want to be? What kind of company do you want to build? How can you connect to purpose and lead from that place? We’ve created a 5 day self-guided email course to help you reboot your leadership and reboot your life. Each day has a short written piece, an audio clip, and some thought provoking prompts that are bound to open up meaningful conversations amongst peers, partners and significant others.

How to Avoid Burnout

The startup life is an intense and intensely personal experience. Poet David Whyte said, “Work is where we can make ourselves; work is where we can break ourselves.” We’ve seen so much of the making and breaking in this world of fast paced startups, big exits, and failures. Perhaps the greatest detriment has been the rise in burnout and depression in the startup community. What follows is our absolute best advice on how to navigate the startup world without losing yourself in the fire. It starts with radical self inquiry. We’ve put together a series of prompts to reflect upon and ignite your own process of self-inquiry so you can avoid burnout.

Having Difficult Conversations

One of the hardest things about being a leader is having difficult conversations. The fear of having the conversation can prevent us from having them, yet these often are the most important conversations to have for the sake of your team, your product, and your company. Being authentic during these conversations is the most effective approach, which requires you to be fierce. However, being fierce doesn’t mean being ferocious. Being fierce means cutting through your own delusion or the delusion in your organisation, moving past paralysing fear and saying what isn’t being said. What tends to happen is a sense of relief or release of built up tension. Jerry’s 20-minute Being Fierce presentation at the ‘Spark Capital Sessions’ speaks to the importance of this for leaders at any level of an organisation brilliantly.

Know You’re Not Alone

A core tenet of everything we do at Reboot is the belief that sharing experiences with peers (a cohort of similarly-experienced people) is an essential element in creating personal resilience. There’s magic in knowing you’re not alone. This is why we created our Peer Groups to provide practical leadership skills and radical self inquiry support for leaders.

One way to join the conversation on things that founders struggle with is to listen to our podcast. The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. In each episode, entrepreneurs, CEO’s, and startup leaders discuss with Jerry the emotional and psychological challenges they face daily as leaders.

One of our recent episodes – Episode #31 Why Being Real Matters – features Evgeny Shadchnev of Makers Academy in London. We have a couple more episodes featuring Londoners: Episode #30 Who Do You Turn To – with Yancey Strickler of Kickstarter & Ian Hogarth of Songkick, and Episode #12 The Journey After the Journey – with Polar Explorer Ben Saunders, who spoke at the launch of Upscale.


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