Startups and the freedom myth


I’ve just finished reading Ryan Hoover’s post: Startups ≠ Freedom.

He writes:

People start companies to become “their own boss” for the same reason — they seek freedom. But in most cases, it’s ironically the exact opposite. As a founder, you’re responsible to your investors (assuming you take money), your team, and your users. There’s no “two week notice” like in a regular job. It’s empowering and scary. Many romanticize startups and ignore this reality when pursuing entrepreneurship.

This came at a poignant time for me.

When I first started doing entrepreneurial things, the driving factor was about creating freedom: freedom to focus on building things without constraints; to solve problems I was passionate about and to work with people I wanted to. Freedom to work to my own productivity rhythm and schedule. Freedom to say no, and yes to new things. Freedom to experiment and explore.

Five years ago, I quit my management job, sold most of my possessions, travelled the globe and lived in Airbnbs. I was consulting and bootstrapping my first company. It was an extremely liberated state of being – highly independent with full freedom of expression.

Being the CEO or founder of a investor-back startup is a very different experience. You taste a different sense of freedom. Like Ryan says, you’re empowered and have a ton of responsibility, but you aren’t free. It’s a huge commitment and you have to really want to do it. The desire to do it is innate.

I’m lucky in that while my day to day has changed since raising funding, our product is all about putting the ‘free’ in freelancing – connecting marketing, content and community professionals with remote work gigs. If I wasn’t working on CloudPeeps, I’d actually be a Peep! I’d work on clients like Beather, be a nomad like Briana in South East Asia and start fun side projects like Tom. Witnessing people take the next step on their journey and going independent inspires me all over again.

While this post is less to do with recommendations (asides from suggesting you read this related Paul Graham essay), one of the things I’ve found helpful in my funded startup journey is allowing myself the time to still ‘live’ and have fun. If you’re going to give everything to your startup for five-plus years, you may as well do it in a format that energizes and fulfills you.

For me, that’s getting out of the city now and then to work remotely. I’ve just spent 10 days in Mexico where RescueTime tells me I’ve been more productive than at home, where I’ve checked out local coworking spaces, got on an early-riser schedule, Slacked with my team, shamelessly Instagrammed, and still enjoyed the odd comically-touristy piña colada. :)

Celebrating character and what we do when no one is watching


Last Friday evening I got the chance to see The Theory of Everything starring Eddie Redmayne as Stephen Hawking. My friends know me as being particularly obsessed with the gloriousness that is Redmayne but I point to this movie not for his talent alone.

You see, I’ve been thinking a lot about character, relationships and giving recently. What I liked about this film is that it portrays the love, support, care and commitment Jane Wilde gave to her partner as he battled motor neuron disease. The story is as much about compassion and sacrifice as it is the career trajectory of a physics genius. In a way, the hero’s journey refreshingly revolves around Wilde as the carer, not Hawking.

This brings me to character. We very rarely highlight certain attributes of the people behind the scenes – especially in the entrepreneurial or business press. I’ve been reading Susan Cain’s book Quiet: The Power of Introverts in a World That Can’t Stop Talking and early on, she discusses personality traits that were celebrated prior to the explosion of ‘the salesman’ type. Attributes that were revered pre-1920s were described by words like: “citizenship, duty, honour, morals, manners and integrity”. After this time, etiquette guides focused more on being: “attractive, fascinating, dominant and energetic”.

The book has made me more conscious of what qualities I naturally value in people. It’s given me confidence to see through the ‘jazz hands’ exterior into someone’s core character set. I’m especially inspired by those who do good deeds but don’t share them. In the days of social media, we often broadcast actions for vapid reasons like attention. It’s what we do when no one is watching that counts.

You can easily judge the character of a person by how they treat those who can do nothing for them. ~ Malcolm S. Forbes

I’m also intrigued about the future of work, with the advent of distributed teams and technology as more and more of communication is going to be based online. Therefore, it’s not those who are the loudest or most self promotional in the workplace arena – verbal orators battling it out – but rather, the writers, the listeners, those with great awareness and perception. These people might not have been heard much in the past but they can be now when our days are spent on tools such as Slack.

The environment is changing from being optimized for extroverts to one where introverts can thrive too. How we hire and vet candidates will evolve as a result. We’re moving into the reputation and trust economy, led by the influx of review-filled marketplaces, where character is center stage.

I’m excited about where things are heading. :)

Image credit: The Theory of Everything

10 ways to win at professional time etiquette

time I think of the last year and a half I’ve spent in New York as professional finishing school. If there’s anywhere on this planet where people are stupendously busy, it’s this place. It definitely took me a few months to settle into the rhythm. Combine this experience with recently fundraising, and I now feel incredible mindful of everyone’s time. So, without ado, I wanted to share 10 tips on how to win at professional time etiquette:

1) For the love of humankind, be direct with asks

Growing up in England and Australia, I was taught to be the opposite of direct. Skirt around issues, don’t address things head on, be tirelessly polite and pad lots of superfluous info around a lone ask. What I’ve now learnt is that one of the kindest things you can do for someone’s time, is to be as direct as possible. Don’t ask someone for coffee if you can put something in a one-sentence email.

2) Do double opt-in introductions

When I receive an email with the subject line: “Introduction…” my heart sinks. Connecting someone to another without asking the person if they want to opt-in, in a professional context, isn’t a favour to the recipient – it’s often a burden. In the days of overflowing inboxes, managing requests and day-to-day work – we can be plagued with guilt of not being on top of it all. The best referrers understand signal over noise – what each party is looking for. Over time when you build up trust in a professional relationship… use it wisely.

As Fred Wilson writes on AVC:

“When introducing two people who don’t know each other, ask each of them to opt-in to the introduction before making it.”

If you’re the one asking for an intro, include the context and a blurb that the introducer can easily copy across. Make it easy for people to help you.

3) Bcc the introducer post introduction

Once you have that intro, reply! It sounds super obvious but there’s been countless times when someone has sent an intro to me and the requester didn’t reply. Don’t be that person! When you do reply, move the person introducing you to bcc so they see you’re on it but you’re not clogging their inbox. Simply say thanks and that you’re moving the introducer to bcc in the email copy. No more getting stuck on irrelevant back and forths.

4) Don’t ask questions that you can easily google

Please don’t ask what someone’s email address is via social media when you can easily find it on the web. The same goes for other minutiae like addresses. If I’m sending a calendar invite through for a meeting, I’ll find the office address online (if it’s not on the website, look in their email signature, Foursquare/Yelp data and so forth).

If you’re reaching out to someone for advice, make sure you’ve read what’s out there first. Every man and his dog seems to have been interviewed about their journey or write a blog with their thoughts these days. Don’t make people repeat themselves.

5) Don’t abuse Facebook messages

This depends on personal preferences but I’m less of a fan of using Facebook messages for work comms. In a way, I’m glad Facebook is now splitting out the messenger app so I don’t have to install it and can switch off from another inbox to manage. If you want to say something important and have a request, don’t send it via Facebook. It’s likely just going to sit in someone’s ‘Other’ section unnoticed or just annoy them while they’re busy wading through the latest click bait in their feeds!

6) Calendar invites or it’s not happening

If you’ve arranged to meet someone or are hosting an event – calendar invite that thing up! Forget Facebook events invites or group text messages, New Yorkers send Paperless Post invites that you add straight into your calendar. It often takes weeks to get on people’s schedule here – you’ve got to make sure you’re literally on it. If you’re finding scheduling is taking up a lot of time, check out services like Zirtual or

7) Do phone calls

I have to admit, I used to hate phone calls… I’d much prefer an email. When I first moved to New York, I was surprised at all the phone call suggestions verse in-person meetings. The thing is, getting around the city takes a lot of time so why spend two hours out of your day commuting then having coffee, when you could fit it in an half-hour phone call. The same goes for email – if you’re forming work relationships, don’t ping emails back and forth, New Yorkers pick up the phone and hustle.

8) Do your background research

Preparation and research beforehand will make your meetings. Don’t spend time asking basic questions – the more you can deep dive, the livelier, more interesting and memorable the conversation will be. If you’re fundraising, for instance, go in knowing what companies/founders someone’s invested in, what their investment thesis is and if you’re at the right stage (e.g. What’s their average check size?). It’s likely not worth both of your time, if these things don’t align.

In terms of insights, Refresh is seriously a great app – it offers a nice (and often a bit too ‘stalkerish’) overview of the people you’re meeting with. It’s actually made it onto my phone’s homescreen it’s been that useful.

9) If you’re not 10 minutes early, you’re late

Australians are known, well, for being casual with time. It’s quite okay to ‘rock up’ five to 10 minutes late to a meeting there. I mean, it’s obviously not great manners but most people do it. Fast forward to when I moved to New York, and started working with my co-founder Shala who preaches arriving well beforehand. Over time, I’ve stopped scaring her by arriving in the nick of time – and now give myself 10-15 minutes before any meeting.

10) Follow through

Pipeline’s Natalia Oberti Noguera recently said at a conference:

“Fortune is in the follow up.”

All of the above tips are nothing if you don’t follow up and follow through. Following up makes it worth it and is the ‘getting stuff done’ part – make sure you get your follow ups done within a few days post-meeting.

Anything else to add? Leave a comment below!

Image credit: The one and only Salvador Dali’s The Persistence of Memory

The Daily Gratitude: a complement to the stand-up meeting


I recently started a new company where I’ve been heads down doing a lot of testing and building. Part of this experience has been working with a new team – specifically my co-founder Shala, who is one of the fastest growing individuals I know.

From day one, we’ve started to think about our culture – and the focus on culture has been inspired a lot by our advisor Joel Gascoigne and the crew at Buffer. (You can view their culture deck here.)

Among many things, like kindness, humility and authenticity, we deeply value gratitude. The thing about gratitude though, is that it’s not just an attitude – it’s a practice.

Vulnerability research professor and TEDster Brene Brown discusses the cultivation of gratitude in these videos here and here.

“These folks shared in common a tangible gratitude practice. They either kept gratitude journals, they did a ‘1234’ every day, they said something out loud that they were grateful for, or they said grace at dinner.”


“It’s gratitude that makes us joyful.”

Joy is an incredible emotion to harbour while building a company as there’s always more that needs doing and moments of pure contentment are fleeting. Joy is like an energy snack you can pull out when you’re exhausted by the startup marathon.

There’s been a lot of focus on the practice of mindfulness – meditation, yoga, breathing and so on – but I’d say the practice of gratitude has as much of an impact on the balance and outlook of ‘self’.

Gratitude also has a scientific relationship on happiness. You may recall this Soul Pancake video that went viral last year.

With all this in mind, we’ve formalised our gratitude practice at CloudPeeps via ‘The Daily Gratitude’ – a verbal or written note of thanks we share at the end of the day. While our standup meetings in the morning talk about achievements, tasks and blockers, mostly related to work, it’s our gratitude sessions that reflect back on our progress and joy.

Here’s two examples from our sessions:

“I am feeling a deep resilience and confidence with what we’re doing – and that feels so good.”

“I am grateful to be able to completely trust you. Really awesome.”

What’s nice is that we’ve begun to incorporate some personal moments (like simply enjoying a walk in the park on a sunny evening), which means the process is more holistic and contextual.

So, have a go at practising a Daily Gratitude session – I’d love to hear how it goes.

Image credit: Oil Painting of the Dog Star, Deb Anderson

I can’t decide if I want to write in British or American English anymore so bear with me.

The joys and benefits of keeping a low profile online


“The monotony and solitude of a quiet life stimulates the creative mind.” ~Albert Einstein

In the age of the perfectly-lit selfie, the algorithm-gamed status update and the never-ending quest for more, we have become lost in the attention economy. We find ourselves in a tiring ‘sharing’ cycle – in an ongoing pursuit to be heard.

How many articles do you come across everyday telling you to create a ‘personal brand’ or build an online profile and following? It’s nauseating.

It’s going to be hard for me to continue writing this with a straight face. I mean, every time I use the term ‘personal brand’ I want to leave the internet forever. But, I’m fascinated by the sociological way we now represent and express ourselves online – crafting our lives in one neat communicable package.

I’d love to share something with you: I had a personal brand and I hated it.

Personal brands are incredibly limiting. They put you in a box that has defined values and then you continue to attract people and things to that box. This noise drowns out your deeper wants and needs. Personal brands grow exponentially and then you end up as a person known for being known, not for what you contribute.

Personal brands aren’t to be confused with reputation – the latter develops from primary sources: from first-hand interactions you have with people. Reputation is like a thoughtful LinkedIn reference from a ex-colleague while personal brand is those annoying LinkedIn endorsements (of which I’ve amassed ~1200 of, for many things I know nothing about).

So, back to the downsides of online profiles. I recommend you start by reading the founder of Lifehacker, Gina Trapani’s post on The Flip Side of a Big Audience. She articulates her experience well and summarises it to:

  •  You field a weekly flood of pitches
  • People who don’t know you make wildly inaccurate assumptions about things you say
  • You forget how to share with people who do know you
  • You get addicted to the approval of strangers
  • Your view of the world gets skewed
  • You’re a spam magnet and a troll target

The first one hit home. Before I moved cities, well countries – from Australia, and became a pseudo-recluse, I’d wake up daily to a stream of requests and asks from strangers. Even old school friends I hadn’t heard from in years would send Facebook messages wanting help. Jobs, intros, general promotion – you name it. If I met anyone in a professional setting and they were aware of my background, I’d literally see a change and flicker in their eyes while their brain pondered what they could get from me. For a while, 90% of communication that came my way was people wanting stuff. I became so accustomed to it that I was automatically on the defense, trying to protect my energy. I became completely flooded with incoming that when I needed help growing my company, I had no idea how to reach out or contact people myself.

You also forget which people are your friends and which are ‘industry friends’. Two of the loveliest people I’ve encountered over the past few years include one from a random Craigslist inspection and another on a long-haul flight.

And let’s not get into Gina’s post about being a troll target or how people treat you when you say no to their request.

After spending 2013 purposefully quiet and concentrating internally, I am so grateful for the space that has been created. Space is important as it allows you to experiment away from people’s view. If you’re an entrepreneur you especially need this freedom to explore while your offering finds its true place. And the thing is, you must be comfortable being misunderstood during this time. The people around you might not have any idea what you’re working on. They might not know where to place you. It’s okay – it’s all part of the hero’s journey.

“I believe you have to be willing to be misunderstood if you’re going to innovate.” ~ Jeff Bezos

To finish, let’s include an obligatory Ralph Waldo Emerson quote. In the Self-Reliance essay, he discusses the need for ‘each individual to avoid conformity and false consistency and follow his or her own instincts and ideas’. He writes:

“Ah, so you shall be sure to be misunderstood.’ — Is it so bad, then, to be misunderstood? Pythagoras was misunderstood, and Socrates, and Jesus, and Luther, and Copernicus, and Galileo, and Newton, and every pure and wise spirit that ever took flesh. To be great is to be misunderstood.”

So, here’s to 2014. You’ll find me in the corner – popping up to say hello to share what we’re creating but not for the sake of it.

Image credit: Madison Latimer

How to keep believing in yourself

Simon Pemberton

I stood there catching my breath. A gush of thoughts were racing in my mind. “You don’t even believe in me,” I sighed to my best friend. “No one does.”

It’s funny how as soon as the words left my mouth, it dawned on me. A metaphorical mirror – a projection of my own reality. I’d hit a wall. Exhausted physically and emotionally from working 100-hour weeks, it was now as clear as day: I had lost my way in believing in me.

This wasn’t about others, it was about my own relationship with myself.

Usually fueled by a quiet confidence, I’d become worn down. Paralysed from making decisions as big as the best way to issue company stock right down to the minutiae of which Instagram filter to use. I was plagued with self doubt. Which was the best way forward? What are all the possible outcomes? Are things succeeding or failing? Who can and will help me?

Some people think they’re awesome. They even outwardly share the sentiment. From a young age, parents coo to them how special they are. Unfortunately, I’ve battled with feeling the opposite for most of my life. Couple this with an energetic drive and you have a delicate tension to balance.

The thing about entrepreneurship is that you’re forever operating outside a box – or known boundaries. That’s why some of the greatest innovators are ignorant to begin with.

“The trouble with the world is that the stupid are cocksure and the intelligent are full of doubt.” ~Bertrand Russell

This freedom can be crippling. Your confidence can be built to egocentric levels one day and smashed down to nothing the next. You contemplate how taking a job would feel like a sweet retirement. You are drowning in advice and critical feedback from everyone, and forget what it was like when you were in that position. You look around at everyone’s social media showreels and wonder if they are going through the same.

“Entrepreneurs have struggled silently. There’s a sense that they can’t talk about it, that it’s a weakness.”

It’s only now that publications like Inc. are uncovering tales from founders with articles such as The Psychological Price of Entrepreneurship. While one of the most-loved conferences by web geeks, Brooklyn Beta, created the space to host and share these conversations at this year’s event. Leading startup incubator Y Combinator also recently funded 7 Cups of Tea – a mental health platform that connects you with qualified listeners.

We’re only just beginning to rejoice in what sharing in this area can be like.

With some space, it’s been almost comical to personally reflect on my progress. How our company can be profiled in a national newspaper one day, an incredible co-founder join me the next and our growth be up 50% month/month in November – and still feel this way. Which brings me to:

“Never let the things you want make you forget the things you have.”

It’s natural we want to keep pushing, but it’s important to recall the wins so you can curb any self doubt. One helpful tool is iDoneThis, which will show you what you did rather than your to-do list. The Minimalists discuss in the Costs and Benefits of Awareness how:

“Our standards change whenever we are infected with a new awareness. We scrutinize ourselves more. The more we scrutinize, the more the spotlight brightens, and the more our imperfections stand out.”

In How to Believe in Yourself in the Face of Overwhelming Self-Doubt on Tiny Buddha, Melissa Ng recommends to be careful with who you surround yourself with. When you are rebuilding your belief, keep away from toxic people who will tell you “No” or “You can’t”. I often divide people into two groups – your ‘critics’ and your ‘cheerleaders’. Your critics are crucial for providing awareness that helps you grow, but in times of self-criticism and doubt, devote time to your cheerleaders who will egg you on and boost you up.

Ng also says: “Self-doubt never disappears. Over time, you just get better at dealing with it. It will greet you every time you fall out of your comfort zone and whenever you strive to do something great. But know that it’s not something you have to fear or resent. Your doubts are only thoughts, not your future.”

Now excuse me while I go remember and appreciate I might actually know stuff. :)

Image credit: Simon Pemberton