What are your top 3 challenges?

There are a few key things which looking back I remember I was very bad at. One of them was asking people for advice.

I think a key turning point with this was when we raised funding for Buffer last year. We quickly learned that in order to get a meeting with an investor, we’d need a good introduction from someone they knew. Since we weren’t asking & pitching that person, we realised we should ask them for advice. It was only then that I discovered the power of knowing our current key challenges.

Anyone wants to help you

I think one of the big myths is that people are too busy to give advice, or that people don’t want to help you. The reality I’ve found is that everyone wants to help you, and the key is deciding you want their help, and approaching them with a definite question. People love to talk about themselves, and love being asked about the challenges they’ve overcome.

"Most people don’t get those experiences because they never ask. I’ve never found anybody that didn’t want to help me if I asked them for help." - Steve Jobs

Always have 3 things in mind that you want help with

After I realised that people genuinely want to help, a powerful habit I’ve developed is to always have in mind my top 3 challenges. Here are my current 3:

  1. Hiring. We need more engineers and I’m working almost full-time on that task right now. How do you approach hiring?
  2. CEO role. Now that we’re 7 people and hiring 2-3 more engineers as well, I’ve realised my role is changing a lot. What was the transition like for you from a handful of people to 10+?
  3. Growth. We’re 100% focused on growth right now, and we’ve found mobile will be key. What are the key growth drivers for you?

Having these three challenges easily to mind is super powerful. It means that if I happen to have the chance to meet someone, I can always get a lot of value, and make a good impression. Just yesterday I had a chance to ask someone about the growth challenge. What’s more, smart people who you want to speak with will like it, because I’ve found most successful people want to maximise the time they spend having interesting discussions around ideas, rather than talking about people or events:

"Great minds discuss ideas, average minds discuss events, small minds discuss people." - Eleanor Roosevelt

How to know what you want help with

In order to figure out your 3 things you would love help with, you’ll need to actually spend time reflecting on what is holding you back. Some of the key changes I’ve made within Buffer have come into my mind during my evening walk, when I spent time with the laptop closed.

Gabriel Weinberg talked about a similar concept in his recent article on why you should avoid working at full capacity:

"I think you have to consciously not work on things, which is always hard to do."

This is one of the hardest things to do as a startup founder, and the easy thing to do is to work all hours and sacrifice your sleep and health.

Go out there with your purpose in mind

Once you’ve figured out what you need help with, and you have it easily to mind, the key is to get out there, take some risks and ask people for help. I often talk about my experience of first landing in the bay area with friends who have had success out here, and we always came to a similar conclusion: silicon valley can truly accelerate your success, so long as you know what you want to achieve. As soon as people figure out what you are trying to do, they will do all they can to help. The pay it forward culture here is very real.

Have you had success in asking others for help? What is the best way you’ve found to make the most of the chances you get?

Photo credit: Karel Seidl

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