6 suggestions for an aspiring founder

This article is inspired by Startup Edition in response to “What advice would you give young entrepreneurs?”

I feel incredibly lucky that I managed to jump on board the path of building a startup. Having hit upon a product that solved a key pain for many people, Buffer has grown rather fast. We now have over 850,000 users and the team is 12 people.

When I reflect on how quickly things happened and what it has required of me, the first thing that comes to mind is Paul Graham's essay entitled How to Make Wealth. In particular, this part resonates with me:

You can think of a startup as a way to compress your whole working life into a few years. Imagine the stress of working for the Post Office for fifty years. In a startup you compress all this stress into three or four years.

There’s a lot to learn if you aspire to build a startup. I have thoroughly enjoyed the journey, and I can only recommend it to others. I can’t think of a better way to lead a fulfilling life. Here are 6 suggestions I have if you happen to be getting started along this road:

1. Experiment. Lots.

"If you’re not already doing a side project, I’d recommend starting one. Although they can complicate your schedule and make life busier, they are one of the few consistent keys I’ve observed in almost anyone who has impressive accomplishments." - Scott Young

I’ve mentioned previously that the Internet is littered with my past attempts to create a successful startup. Even before I knew I truly wanted to build a startup, I played around with countless side projects and they are spread across the web, too.

I think there is often a misconception that to be successful you need to focus and put all your eggs in one basket. That’s not how it happened for me. I tried a ton of different things, and I started Buffer on the side while working full-time as a freelance developer. The key is to focus once you have something that works, that gains traction and people love. Until then, I say experiment away.

2. Stay inspired.

"People often say that motivation doesn’t last. Well, neither does bathing - that’s why we recommend it daily." - Zig Ziglar

Looking back to the early days of my first startup attempt, I think something that kept me going was that I continually read books about startups and entrepreneurs and watched as many interviews of founders as I could find. In fact, I was especially humbled to be invited to share my story on Mixergy precisely because I have watched tens of interviews by Andrew Warner and they always inspired me to keep pushing forward.

It’s true that at some point you have to stop soaking up the motivation and actually get to work. However, I think a lot of people underestimate how powerful it can be to be take in the learnings of others. Especially in the early days when you might not necessarily be surrounded by others trying to do startups, I think staying inspired in this way can plant that spark inside to help you make it happen.

3. Travel the world and move.

"Travel is fatal to prejudice, bigotry, and narrow-mindedness." Mark Twain

Travel is something that I always thought would be fun, and I never imagined the impact it could have for me. From simply moving a hundred miles from my hometown of Sheffield to Birmingham in the UK, to then traveling several continents and living in San Francisco, Hong Kong and Tel Aviv, I’ve been extremely lucky to have experienced completely different cultures and meet great people.

I truly believe that if you choose to travel you’re immediately much more likely to succeed with whatever you are trying to do. Leaving what you know and stepping into uncertainty, you naturally become more open-minded and create new opportunities for yourself.

Interestingly, many have an attachment to their hometown and want to be there in order to help their town and others who live there. My belief is that you can do a lot more to help your hometown if you make the decision to leave. I’ve never once heard someone regretting their decision to travel.

4. Choose your friends wisely.

"You are the average of the five people you spend the most time with." - Jim Rohn

One of the most interesting side-effects of moving and traveling a lot has been that in every new place I have settled in, I have had the chance to rethink every part of my life. I reflect on what kind of place I want to live, how close I want to be to all amenities, what routine I want to adopt and even who I want to hang out around.

The clear example of the power of adjusting your group of friends is that your school friends probably aren’t all entrepreneurs. The thing with doing a startup is that it’s an unusual path and one where there are far more reasons it can go wrong than can go right. If you truly want to succeed, surrounding yourself with other optimists is one sure way to have much better odds. The cool thing is, these are really fun people to be around.

I strive every day to meet (and hire) more people I can learn from.

5. Stay laser focused on building something people want.

"In nearly every failed startup, the real problem was that customers didn’t want the product." - Paul Graham

It’s easy to get distracted when you begin your startup endeavors. You might take a look around and assume you need to incorporate, or raise funding, or countless other things that everyone seems to do.

In my experience, all that really matters is to try and find a real problem to solve. What it comes down to is whether you have hit product/market fit. If you have, you’ll know it, and you’ll start to get traction.

If what you’ve built isn’t working, keep experimenting with new ideas.

6. Be open and vocal

"If you have an apple, and I have an apple, and we swap, we each still only have one apple. But if you have an idea and I have an idea and we swap, we each have two ideas." - George Bernard Shaw

Before Buffer, I had a few previous startup ideas that weren’t too successful. One of the things that is easier to reflect on in hindsight is that luckily during that time I was Tweeting, blogging, going along to events and generally getting to know a lot of people.

When people ask me what my initial marketing was to get Buffer started, the truth I have to share is that my marketing consisted of sharing the idea with the 1,700 Twitter followers I had at the time. I attribute my previous openness to the fact that I had these followers to help me get Buffer started. As a result, I completely agree with Leah Bursque’s advice:

"Talk to every single person you meet about your idea. Talk until they tell you to shut up. Discover new questions and patterns so you can test and refine your idea. Then find more people to talk to."

What advice would you give to an aspiring startup founder? I’d love to hear your thoughts.

Read more on this topic from an awesome group of entrepreneurs at Startup Edition.

Photo credit: Robert Scoble

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 context is so important

I’ve had a few different experiences in the last couple of weeks which made me reach a big realisation. What I’ve discovered is that the context of any situation is very important. Hiten Shah clearly already understands this very well. This Tweet from him popped up with great timing for the thoughts I had in my mind, and it is what’s tipped me over the edge to write this post to share some of my further thinking around context:

Get context before you give advice.

Hiten Shah (@hnshah) August 30, 2012

Why we should seek context at all times

"Seek first to understand, then to be understood" - Stephen R Covey

The above quote is Habit 5 of Covey’s 7 Habits of Highly Effective People. I’ve read the book a couple of times, and I’ve read other content around the topic of gaining context, but it’s something which has only just “clicked” for me as to why it’s so important. Also, after now understanding the importance of context, I’ve found it to be very difficult to actually practice.

The premise is quite clear as to how vital context is: without context, we immediately jump in our heads to what we want to say next, based on the very first few words we hear from the other person. This is something I find myself doing far too frequently.

Most of us listen to someone with the intention of replying, and therefore as soon as we have a “reply” in mind, we stop listening and wait our turn to reply. No matter what remarkable new insights are uncovered in the subsequent words from the other person, it is likely that we now have a strong desire to share that initial thought we have about what to say back.

With context, on the other hand, we can achieve so much more. If we truly understand the background of the other person, we can tailor the approach for each occasion. I believe gaining or having context can be useful in so many scenarios:

  • giving advice
  • receiving advice
  • meeting a stranger
  • making friends
  • getting press
  • raising funding

The conversation that shocked me

I was recently in a Skype call with someone to try and help them with their current startup challenges. This is something I do several times a week, and it seems to be very useful for many.

In this particular Skype call, as normal I asked about the founder’s startup and what stage he was at. After uncovering a tiny amount of context about his previous experiences and where he was now at, I unfortunately slipped and switched to my own thinking about what the best next steps were for him.

I proceeded to advise him based on my previous experience. The experience I based my advice on was the following:

  • I had worked on an idea for a year and a half which I never charged for
  • I therefore generated no revenue, and consistently had to work on the side
  • Whilst I had a few thousand users of traction, I failed to raise funding

I advised him to charge for his product from day one, since that worked for me the after the first failure. I also advised him to aim for revenue and not worry so much about user numbers, since that’s what truly freed me from working on the side.

Luckily for me, he was very receptive of my advice even thought it was the wrong advice for the situation he was in. Even luckier, he went on to share extra information about his context which changed everything:

  • He had a previous startup for which he had hundreds of paying customers and good revenues
  • He was still making money from the idea and had runway to last almost indefinitely working on a new idea
  • He got into an incubator with the idea
  • He went to the valley to raise funding, but since he had low user numbers (even though they were all paying) he struggled to raise funding

I could now completely understand why, in fact, he shouldn’t just follow the advice I gave him. He had almost entirely the opposite previous experience to me, yet equally valuable and foundation building. He was perfectly poised to try an idea which could gain massive visibility rather than simply making money. Making some money was not his biggest challenge, as it was for me when I started.

Our opposite contexts meant that in fact opposite choices for next steps made complete sense. I was genuinely taken aback when I realised this.

Some techniques to uncover context

Practicing “searching for context” is something I’ve found to be very exciting. When you approach a conversation without any need to have the intent of replying, without any need to have a “smart” response, it changes the entire flow of the discussion.

Here are some of the things I’ve found very useful in trying to be focused on understanding the other person:

Give the other person your full attention

Whenever I have a Skype call, or whenever I get dinner with someone, or when we have a team standup, I turn my phone over and try to adjust my posture to lean forward, into the conversation, and focus on hearing every single word. It can be a challenge, and sometimes my mind drifts, but with conscious effort to do this, I have found I can “train the muscle” and focus for longer.

Remember that you don’t need to respond

I used to feel that I always had to respond if there was the slightest moment of silence between myself and someone I was speaking with. This assumption led me to prepare a response in my mind. As soon as the thought entered my mind, I would stop listening and wait for the other person to finish talking. I literally wouldn’t hear any more words, and sometimes I would even jump in before they had finished.

I’ve since realised that there is great pleasure in simply listening with the knowledge that I don’t need to respond. If I pause to think, and I say “hmm, that’s interesting” after the other person has spoken, that is something that is respected. Also, often if I pause for a little while, the other person will pick up again and if it’s a challenge we’re working on they might come to the solution by themselves. It’s much more powerful if they find the solution, than if I come up with it.

Ask lots of thoughtful questions

If it is indeed my turn to talk, I try to avoid “giving advice” or “stating my opinion” for as long as I possibly can. Instead, I ask questions based on the previous thing the other person just said. I listen very carefully and then once it is my turn, I simply respond with a genuine question of something I’m interested in based on the topic, but which he didn’t quite cover or for which I’d love to hear more detail.

If I have an idea to help the other person, I try to always present it as a question. I aim to guide them to my idea through questions. This means that if they reach the same idea and it’s the right thing for them, it will be much more ingrained and they will be much more likely to have determination to follow through.

Be open to whatever path the conversation takes

This final point is the one which I think has been the most powerful recent discovery for me. I’ve realised that if I simply sit, feel no need to respond, and focus on hearing every word and learning quickly about the other person’s context, then very often the conversation will go down a whole new path than the “initial thought” I had which I used to respond with or jump in and cut the conversation off with.

This is amazing, because I often learn so much. I get to walk down a whole new area of understanding, which I haven’t experienced, rather than just responding based on my experience, which I’ve already gained. The biggest bonus I find is when I can help the other person come up with a better solution suited to their context, by listening and asking questions. This is often a solution I never would have thought of based on my own context.

Do you ever catch yourself having a response in mind and struggling to listen to the other person? I’d love to hear your thoughts and experiences on the topic of context.

Photo credit: Donald Lee Pardue