05 Jun

Kate Kendall in Conversation with Steph Stephan

This article was originally published on fridaybestmag.com
Kate Kendall in Conversation with Steph Stephan

Kate Kendall is a San Francisco-based, British-Australian entrepreneur and writer. She’s the co-founder and CEO of CloudPeeps — a new marketplace that connects businesses with remote, professional community managers. She also created The Fetch — a guide for professionals to share and discover what events are happening in their city.

Kate started out as a business journalist and turned to entrepreneurship after quitting her job in Melbourne, Australia, unable to ignore this feeling that there was another way to create her best work. I chatted to Kate from her home in San Francisco about becoming resilient, being a bitch versus speaking your mind, and why women don’t talk about power.

Connect with her on Twitter via @katekendall.


Your life as an entrepreneur kicked off when you left your full-time job at a magazine publishing company. What were those first steps like and how was the transition?

Quitting my job and going independent was definitely a huge learning curve and formative time in my life. You go from having a set understanding of your work life to wondering where your next pay cheque going to come from and what you are going to do when you get up in the morning. It’s kind of like taking the blue or the red pill in The Matrix: you know you need to do it, it’s going to be really hard process, but once you’ve done it you’ll never go back. And when you’re walking outside during office hours, you see that the world isn’t this frantic place where people do all their errands at lunchtime or on the weekend. You think, Is this real life? Am I cheating the system?

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Kate Kendall’s team at CloudPeeps embrace working remotely but they still love a good get-together. Here they are at a Freelance Friday co-working event

Do you think that there needs to be a certain amount of panic for the hustle to happen? To really put things into motion?

Totally, you need to be hungry and you need to have focus. And I mean, when I started The Fetch in 2011, I still consulted for that whole year. You can take risks and still feel safe. So I didn’t go and quit my job and then not have any money. I think that we’re often shown these Silicon Valley stereotypes where a guy quits his job, has 20 dollars in his pocket and he’s 22, so he can live on mattresses in someone’s house. But you can take risks smartly and the more that you dissect how other people did it the easier it is.


You think, Is this real life? Am I cheating the system?


In a talk at CreativeMornings a few years back you talked about the art of negotiating and not asking permission from other people. How did you learn that you don’t have to ask permission?

I was in a very long-term relationship until 2009 and it ended really abruptly. So when you get rattled and you feel like you don’t know what tomorrow will bring, everything becomes a lot more opportunistic and reactive to the environment. But in order to do that—and this is something I talk about in the CreativeMornings talk—you need a really good agile foundation. The agile lean start-up movement really reframed how I thought about the world.


Our intuition and our heart are a lot smarter than our head, so it’s almost like you need to chop your head off and let what you feel do the work!


Because it wasn’t too long after this that you sold all your stuff and moved to San Francisco, right?

Yeah, I did, and believe me, I was a hoarder. It was such a challenge at the time to let go, but I remember staring up at the ceiling in my house for years and just wanting to be in San Francisco. And so when I got off the plane for the first time [in San Francisco] I thought, I never want to go back!

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Kate getting some offline time in Canada

I often think that our intuition and our heart are a lot smarter than our head, so it’s almost like you need to chop your head off and let what you feel do the work! And then later you can reflect and understand the context and the greater meaning of what that was.

Agreed! So how would you describe what an authentic life is for you now?

I’d say that I’m basically doing what I love to do in terms of creating communities and building companies. Sometimes I think, Oh shit because there’s a lot of pressure, but I love that I’m able to focus on what matters and have people and opportunities around me that are the right ones to have. That has really come from learning how to say no and also curating the network that I have around me. It’s also resilience. I’ve been through enough now to know that whatever happens, I have the confidence to pick myself up.


If I am direct and speak up it’s not actually being a bitch. I think I’m being a bitch but I’m actually about mid-way through the scale.


How has the process of learning to say no worked for you?

Growing up I was taught a lot of people pleasing manners. Never say anything negative and be very well behaved. As I started to do more and share more, I found that by doing anything at all you’re going to get criticised. Even when I was people pleasing and trying to oblige everyone I still couldn’t win, and so it then had to balance because I was running out of time and energy. There was nothing left to give and so I started saying no.

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How’s this for an office space? For Kate, great work can happen anywhere in the world, tiny houses included

I then realised that if I am direct and speak up it’s not actually being a bitch. I think I’m being a bitch but I’m actually about mid-way through the scale. So I find that we have to go really hard-core in our thinking because we might then move the needle a little bit.


The thing about resentment is it’s like swallowing poison and hoping the other person dies.


I guess the other thing that sometimes comes as a result of voicing your opinion is conflict. And especially as women, we’re taught to not ruffle any feathers. How do you deal with conflict?

Until 2013 or 2014, my way of dealing with conflict was to feel like something had happened and then completely shut down communicating afterwards. So I’d pretend that it had never happened or we’d just go our separate ways. And then in 2014, I had this motto of a year of forgiveness. I approached the year with an attitude of forgiving everyone and everything that had ever happened. I just wiped the whole thing clean because the thing about resentment is it’s like swallowing poison and hoping the other person dies. 2014 was an amazing year because I just stopped caring.

Was it really that simple?

[Laughs] You have to read a lot about it. It was a practise, like building any habit and I just became really conscious of it. Every time you notice yourself having some sort of sentiment, or holding on to it, it’s about having that awareness to let go. You also tend to know what you don’t let go of after a while.

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Hello, San Francisco! Kate loves a daily walk to the Golden Gate Bridge

As an entrepreneur, have you ever found it hard to ask for help? What do you think gets in the way of reaching out?

I think once you become quite resilient you get used to being very self-sufficient. Most of the time you’ve been able to figure it out yourself, and the more that you can figure it out yourself, the more you get rewarded. But there comes a time when you do need help and I think I’ve been notoriously bad at it. The Fetch was an amazing experience but often every Sunday night I’d be up at 4am still editing the email newsletters to get them out. Everything was around helping others and for long-term sustainability you need to know how to get help yourself. So when we started CloudPeeps, from day one we got three advisors on board and they have all been so amazing.


The only way to lead is to do it in a way that’s true to you.


I see you as a leader as much as an entrepreneur. What do you think makes a good leader and how do you personally like to lead?

A lot of people think professional CEOs look and act a certain way and I feel like I have had pressure in the past from people who expect a certain level of style. But the only way to lead is to do it in a way that’s true to you. I find that I am more on the introverted side, so I don’t want to be in people’s faces all day long. I want to create a company where everyone is empowered to think and knows what they need to work on. I also really like to have transparency, so everyone at CloudPeeps knows exactly what’s happening, our challenges and what we need to do. There is nothing really shielded from anyone and I think that comes from a place of strength.

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Ever wondered if you really need to be sitting in an office? Kate likes to give the CloudPeeps team a copy of Remote by 37 Signals

On that note of sharing and transparency, what do you wish we had more conversations about?

I wish we had more conversations about our own struggles. When I first quit my job I had no idea that how I felt was normal. We need to share what it’s like to take these leaps or to run out of money. And it gets back to killing the divide between what we think is professional and personal, because some of the best leaders and the most professional CEOs are actually highly emotional, vulnerable, intelligent people.


Women do not talk about power. Power is freedom. It doesn’t mean a suit necessarily, or being a 50-year-old man.


Is that what you were touching on earlier when you were saying you had some pressure to turn up in a particular style?

I think it also comes down to being a 30-year-old woman. There’s an extroverted hustler type that people associate with being CEO and I’m a bit like, yes, you can network 24/7 but you also need to build the company. It’s just a different way. And that’s why I respect Joel Gascoigne from Buffer because he’s shown how an introverted leader can build a company and guide people.

One other thing that’s really interesting is reclaiming what it is to be powerful and not having power as an ugly word. Women do not talk about power. Power is freedom, it doesn’t mean a suit necessarily, or being a 50-year-old man. You can still hold your own, navigate situations and get results in a very different format.

So how does that work for you on a personal level?

I think it’s about knowing when to take perspectives on board and still make the decision that you want to make. How you go about making those decisions is power. You listen to everything available but if you follow everyone else, you’ll never know what you stand for. And often there is no clear answer.

Twitter_Kate-Kendall

Last question before we wrap up. What are the guiding philosophies that you keep coming back to?

It’s definitely to be grateful, to be resilient and to surround yourself with the right people.

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