43 Notes

Developer CEO vs Sales Guy CEO


I am a sales guy CEO. One quick look at my LinkedIn profile shows direct sales and partner sales and business development and marketing and sales management. The developers I work with tell me I am about as well versed in things technology as a sales guy CEO can hope to be - but I’m still a sales guy CEO.

This week I had the pleasure of meeting a developer CEO. He’s overseeing a rapidly growing startup that’s already raised multiple rounds of financing to go along with 1000’s of paying customers. We spent an hour talking opposite each other in a booth. 

After I left I thought “Hmm. He asked 80% of the questions and I asked 20%. What’s the significance of that?” So I thought about the conversation further. 

He had an appetite for data. He was curious to learn my thoughts around competition, markets, geographies, team structure around go to market etc. Generalized answers were great but specific answers were much better. Every time I thought he’d exhausted a line of questioning he had one more follow up. In short, he was (unsurprisingly) bright and relentless. I suspect in his mind the benefit of meeting was directly related to his perception of the quality of data in my answers. 

I, on the other hand, find myself answering questions and wondering “That’s a great question. I wonder why he asked that question? It’s interesting how that’s his follow up question. I wonder why he didn’t ask about x instead” I would observe his body language to mentally note when an area seemed to excite, agitate or bore him. I would wonder about the questions he didn’t ask. Most of my questions were “leader” questions. Generalized questions. My questions weren’t so important.  Where he took my generalized questions and drove them to specific topics - that was the interesting part. That let me know what’s on his mind.

Whereas he based the value of the meeting on the quality of the data I focus on how much I think I got an accurate snapshot of how the person thinks and operates. That will give me the context for assessing future activities by his company. Naturally I was also assessing the quality of his answers and he was probably making some observations about me separate to the content of my answers. Still, I was struck by the unique styles we had.

There’s no doubt his style and approach is working really well. It did make me wonder if the best leaders are capable of doing both. I started wondering about the leaders I admired most (at the macro and micro level) and backing into how they approach a new encounter. 

1649 Notes


No. 53 / Ross Moody / 55 Hi’s

60 Notes

[W]hen thinking about difficult, exciting, interesting activities, such as investing in a new business, or perhaps buying a $10 million lottery ticket, the brain areas associated with emotion — such as the midbrain dopamine system — become more active.

Images, colours, music, even social discussion means that the midbrain emotional area becomes dominant, and the rational part of the brain finds it hard to resist the temptation. The emotional centres of the brain simply tell the rational part to shape up or ship out.

The rational part of the brain agrees, and starts to look for evidence that supports the emotional brain — it becomes an ally in the search for reasons why the emotional choice is a good one.

The neuroscience of the constant tug-of-war between rationality and intuition in a world that sees them as a binary divide.    

(via bobulate)

1 Notes

My mission in life is to listen to my own voice as much as possible and follow my instincts. Whenever I do this, I always feel good about myself eventually and I get the glimpse of the freedom of being outside the Matrix. It’s a hard thing to do, but it’s worth it every time. I never lose when I trust myself.
Ji Lee in Self Reliance [Domino Project] (via ellesocial)

6 Notes

Empathy is the Most Powerful Leadership Tool


“Become the other person and go from there.” It’s the best piece of coaching advice I ever received, coming from Tanouye Roshi, and it applies equally to influence, negotiation, conflict, sales, teaching, and communication of all kinds. To become the other person is to listen so deeply that our own mind chatter stops; to listen with every pore on our body until we can sense how the other’s mind works. To become the other person is to feel into her emotional state, see through her eyes, think like she thinks, and see how she views us, our proposition, and the situation at hand. To write it out or read it in serial fashion makes it sound like a lengthy, time-consuming process, but in fact, deep empathy conveys its insights in a flash, and our ability to empathize deepens with practice, as we learn to quiet our own inner state.

(via Fast Company)


18 Notes

Why I’m helping startup founders


Last month I wrote about my discovery that helping others makes me happier than spending the time seeing a movie or doing some other “pleasure activity”. I briefly mentioned that I’ve been regularly helping startup founders, and since then I’ve had a few people get in touch to ask how I do it and, more importantly, why I started helping others in the first place.

It’s true that as a startup founder you have more than enough to do without helping others. However, helping others is something I’ve found to be very useful for many reasons, so I want to share some of my reasons for doing so and why I think you might want to start helping people too.

6 reasons I help startup founders

I enjoy helping people

One of the key reasons I help other startup founders is that I genuinely enjoy helping others. It gets me excited to hear about people’s challenges and about how to improve a situation. Whether they’re struggling to get traction, having difficulties with juggling a startup alongside work, or finding it hard to stay motivated, I get a thrill out of working with them to think of the best steps to take.

A duty to the amazing community

During University I got hooked on the idea of creating a startup. Since then I’ve made many mistakes and learned a lot of lessons. One of the things I’ve been blown away by is the “pay it forward” culture of startups all around the globe. The very least I can do is try to contribute positively to this amazing community, wherever I happen to be.

Do you think I might be able to help you with your startup? Get in touch

Learning about success and failure

We all know that success doesn’t come overnight, and often there are failures along the way. I love meeting people so I can pass on the lessons from some of my failures and at the same time start to spot what works and what doesn’t through other people’s experiences.

A way to experience more startup challenges

There’s simply no way I can experience first-hand what’s involved with all the different types of startups, marketing approaches or technical challenges, even if I build many different startups throughout my career. Whilst it’s never the same to hear about someone else’s learning than to go through it yourself, by meeting other founders you can be exposed to much more and multiply your experience and knowledge.

An outstanding support network

Meeting lots of founders also gives me a fantastic group of people to call on whenever I have a challenge. I might meet an awesome Android developer who needs to chat about struggles of creating a startup such as validating their idea or gaining traction. If I’m having challenges with Android development, I can easily hit them up for help.

Practicing being an amazing advisor

I’ve heard many times before that the investors who succeed are the ones who are very good at recognising patterns. Mark Suster describes this well in his article Invest in Lines, not Dots:

“If you’re an investor looking at dots somebody else may be looking at lines. Meet entrepreneurs early and watch how they perform – maybe even at their previous startup. I always ask to meet people before they’re officially fund raising – well before actually. It helps me spot patterns.”

One of my aims is to be a fantastic advisor, and eventually do some angel investing too. I want to become someone people can call on who has lots of fantastic advice in many of the challenging areas of running a startup. I can only hope to achieve this by experiencing different aspects (bootstrapping, finding product/market fit, gaining traction, raising funding, hiring etc.) and through practicing being concise and useful in short advisory sessions.

Why you can start helping others now

When we were making just $20 per month with Buffer, I had the feeling that I couldn’t help people: I wasn’t successful yet! What I’ve found, however, is that I could help far more people when I was at that stage. I believe you can too, whatever stage you’re at.

Imagine you go to a conference and there’s a big guy on the stage who’s sold his 3rd company for a billion dollars. He’s so far away from the founder sat in the audience who’s just starting with their idea or maybe doesn’t even have an idea yet. The best you can hope to get is inspiration. The worst case is you actually feel stalled by how small the chance of this happening to you is.

With most people I meet, I find that I’m just a few steps ahead or behind. This means the learning is very fresh, the advice is actionable and the results feel achievable. I think this is much more powerful. Even if you’ve just had your idea and are starting to plan the steps ahead, how many people are there that haven’t even got to the idea stage yet?

Have you started helping others, or have you considered it? I’d love to hear about your thoughts and experiences.

Photo credit: Michael Scott

520 Notes


Travel doesn’t always require a plane.


Travel doesn’t always require a plane.

2 Notes

What if you dropped out of school and walked across the country? What if you decided grades were sort of silly, and instead read all the interesting things you could find? What if you volunteered some time in a developing country and met someone who’d never spent a moment thinking about Chandler and Monica? What if you tasted every taste, saw every sight, faced the things that frightened you, and got a couple of scuffs along the way? You have one life. Live it as you will, but perhaps take a moment to consider an alternative path. There is a wide chasm between the ways you could pass through existence and the lame-ass lives most choose. Besides, should you fail, you’ll at least have a couple of good stories to tell.

1 Notes

C.S. Lewis on Writing

What really matters is:– 

1. Always try to use the language so as to make quite clear what you mean and make sure your sentence couldn’t mean anything else.

2. Always prefer the plain direct word to the long, vague one. Don’timplement promises, but keep them.

3. Never use abstract nouns when concrete ones will do. If you mean “More people died” don’t say “Mortality rose.”

4. In writing. Don’t use adjectives which merely tell us how you want us to feel about the thing you are describing. I mean, instead of telling us a thing was “terrible,” describe it so that we’ll be terrified. Don’t say it was “delightful”; make us say “delightful” when we’ve read the description. You see, all those words (horrifying, wonderful, hideous, exquisite) are only like saying to your readers, “Please will you do my job for me.”

5. Don’t use words too big for the subject. Don’t say “infinitely” when you mean “very”; otherwise you’ll have no word left when you want to talk about something really infinite.


1 Notes

The only way to be creative over time—to not be undone by our expertise—is to experiment with ignorance.