One of the incredible side-effects of doing retreats 3 times a year with my startup is that I get the opportunity to travel and experience completely different cultures.
On top of spending a week and a half with the rest of the Buffer team on retreats, in the last two occasions I have made a decision to stay or continue traveling in the same area beyond the end of the retreat.
For our latest retreat at the start of the month, 16 of us were together in Cape Town and I have stayed here 2 weeks so far beyond the retreat. I’m not sure yet whether I will continue to stay longer, or whether I will return to San Francisco. This uncertainty in itself is an example of a new way of traveling which I’ve been experimenting with.
How I’ve adjusted my traveling in the last few years
I’ve been very lucky to be born in a time where there is such a thing as work that doesn’t depend on where you are. We’ve set up Buffer as a completely distributed team (now 20 people across 18 cities in 5 continents), and I’ve had the opportunity to travel a lot already during the Buffer journey.
Leo and I started Buffer in the UK, and after 8 months we moved to San Francisco. We spent 6 months in San Francisco, then 6 months in Hong Kong, and then 3 months in Tel Aviv. After that I lived in San Francisco again for the last year and a half, with a little traveling at time.
The result, for me, of traveling to so many different places is that I started to carry much less with me to each subsequent place. I realized that you really don’t need much to travel, or even to live. In fact, you don’t need much in life at all. I’ve become a big fan of one bag living.
In addition, these experiences were the first time I’d experienced “living” in a place rather than “visiting” a place. Being able to stay 3 months or 6 months meant that I could make new friends, discover the culture in a deeper way and experience working and living there. It relieved a lot of the pressure of “seeing all the sights” in a short space of time, and even on shorter trips now I don’t try to cram too much in.
Traveling around Asia
Our second Buffer retreat was in Thailand in December last year. 10 of us stayed in Bangkok for a few days and then in 2 villas in Pattaya for a week where we worked together and went on a boat trip to a nearby island.
After the retreat, I decided to experiment with traveling by myself, something which I hadn’t properly done before. It was an incredible experience, so freeing for everything to be in your control. Even just the fact that it’s down to only you to get around is interesting, you have to be the one to ask directions or make the effort to meet others, rather than relying on a friend (which I sometimes do).
When we do a retreat, it’s quite a busy time and we fit a lot into the week, not to mention the natural excitement and pressure of meeting people, sometimes for the first time. After Thailand, I decided to travel to Singapore for 6 days, then Taipei for 4 days and then make my way to Japan for Christmas to see my brother, his wife and my little nephew.
It was a great experience to see all these different places in the space of a few weeks. At the same time, I didn’t manage to feel a part of any of these places, I didn’t get past experiencing things on the surface.
Staying in Cape Town
My recent experience in Cape Town is in contrast somewhat to that of traveling around Asia. Rather than visiting other countries in Africa (which would be a lot of fun) I decided to simply stay in the retreat location of Cape Town for a few extra weeks. After the week of retreat, I found an AirBnB place and I could start to build my early morning routine go to the gym again. I found a few coffee shops and a co-working space, and I got to know some people. I did a speaking event and met the startup community here.
With each day that passed, I felt like I got some extra insights into how things work here. I met locals and learned some of the Afrikaans words and some of the differences in how they speak English, too. I quickly stopped feeling like a tourist, although I have been on Safari, hiked to the Lion’s Head and had a kitesurfing lesson. During the week I’ve worked just like I would anywhere else.
I’ve become much more spontaneous with my plans and let things flow based on who I meet and how I feel. I have accommodation for only a couple more days here in Cape Town, so this afternoon I’ll start looking on AirBnB again for the next part of the city to experience.
In the future, I think I’ll take every opportunity to stay a few weeks or even a few months in a place, rather than trying to visit as many places as possible. I’ve found it much more fulfilling to become part of a place rather than simply seeing a place, even if it I’m only temporarily part of it.
Photo credit: Dimitry B
We’ve recently reached the point with Buffer where I’ve started to think about a lot of key higher level choices. As a CEO these can be difficult decisions to make. I’ve been taking time to reflect and luckily I also have an awesome co-founder I regularly bounce these decisions off and an incredible team whom I sometimes get together with and have discussions about our direction.
Regardless of all the support I’m lucky to have, these decisions can sometimes be overwhelming to make. It’s easy to feel a lot of pressure due to the potential impact and consequences of the choices. One decision will literally take you down a completely different path than another.
The choices to make when building a startup
It’s interesting for me to look back at some of the key choices which have made a huge difference to how Buffer looks today. Here are some that come to mind:
- being a distributed team (spread across 16 cities in 5 continents) rather than having everybody in the same city and office
- not raising a Series A (and having no investors on our board) when the usual cycle came around after our $450k Seed
- doing retreats 3 times a year (the last two were Pattaya, Thailand and Cape Town, South Africa)
- choosing to not have a sales team and instead focus on self-serve and word of mouth marketing
- serving small businesses rather than large enterprise customers
- establishing cultural values early and being disciplined about living to them
The questionable impact of each choice we make
The interesting thing about all of the choices I’ve shared above that relate specifically to Buffer is that there are examples of companies succeeding by making the opposite choices in each case. It’s incredibly difficult to say that each choice specifically played any role in any success we have had.
That isn’t to say that the choices haven’t changed the type of company we are. I think they have absolutely shaped what Buffer is today. However, if you were to try and attribute these choices purely to success (maybe take revenue as the metric), then I think we could probably be just as successful with different choices.
Ev Williams has a great example of this around the famous Google 20% time and whether we can say that this contributed to their success:
Google is one of the most successful companies ever. Google gives its employees the ability to spend 20% of their time on whatever they want. Therefore, 20% time is a great idea. Is it? Or was Google successful because theyre brilliant engineers who solved the right problem at the right timekilling it despite the lack of focus 20% time causes? I dont know, and neither does anyone else.
Let’s not always try to tie choices to success
One of the best books I’ve recently read around company culture is Joy at Work by Dennis Bakke. Bakke was the founder and CEO of AES which earned $8 billion in revenues and employed 50,000 people. A fascinating detail is that they achieved this with a highly unusual business philosophy and company culture.
One of the core values that Bakke set in place at AES was Fun. His quest was to create the most “fun” workplace ever. In his journey to fulfill this vision, he found that some supported him and others didn’t. Most notably, he mentioned that several board members had been very skeptical of his approaches but supported him a year later when AES had some of it’s fastest growth. Bakke argued that the value of Fun should not be tied to success nor failure:
I kept saying that our values were not responsible for the run-up in our share price and should not be blamed for any downturns in the future.
This was a point that took me a long time to understand. If we don’t attribute our choices to success or failure, how can we assess if we are on the right track? I think in this case, the point is that our values should hold true in either case, and we should stand by them.
This is the approach we have started to take at Buffer with our cultural values such as Happiness and Positivity or Defaulting to Transparency. I can’t say that creating a company where everyone is happy is something that will make us more successful, and I can’t say that being fully transparent about revenues, user numbers, salaries and other details helps us grow faster than other companies. These are simply values we have chosen to live by.
Even choices like serving small businesses rather than enterprise customers, or being distributed rather than having a single office are decisions which will be difficult to assess at any time. If we fail eventually, I don’t think we could easily tie it to a single one of these choices, and if we succeed we would be wrong to say it was because of these decisions. I think, therefore, the key is to use our intuition and make the changes we feel are right - both in order to succeed, and also to create the place we want to work.
Photo credit: DennisM2
For the first two years of Buffer we didn’t use C-level titles. In February last year it started to make much more sense for me to use the CEO title, and soon after Leo became CMO. We had grown up a little and were not just a bunch of people hacking on a product. There was a little more structure and it was helpful on the inside and from the outside to reflect that.
For half a year Leo used the CMO title, but it never felt quite right. The CMO role felt quite narrow and specialized, and Leo had much more to contribute than that. He had always helped me to think through other areas. In addition, Leo has a real growth mindset which made sense for marketing, but also for much more than that. The company was growing fast and it made sense for Leo to have more responsibilities than purely marketing.
How we initially structured the COO role
I asked Leo to become COO in November last year. I wasn’t really sure how that would work and what it would change, but I knew it would definitely be different. It felt right, and exciting.
Leo and I spoke and reflected on the key strengths he had and how we wanted to have him involved in all areas to push us further. The title felt perfect since I would describe Leo as someone who really thrives with operations. He will always get everything done in his list, no matter what. And he’ll always choose to have more in his list than anyone else. This is something I’m incredibly inspired by.
We structured ourselves with the analogy of a train. I would be thinking about laying the track ahead in the right direction, and Leo would help the train to run on time and move fast. In practice, this translated to Leo being in sync with every aspect of the company and helping us to improve (product, customer happiness, marketing, growth). He’d sync up regularly with everyone and be someone who could help with setting goals and brainstorming how to keep to them.
Some struggles and learnings with the CEO/COO balance
One of the things that spurred the role adjustment for Leo was that we were right in the middle of going through our quiet pivot. We had realized that growth had slowed with the vision we were currently on, and we made adjustments. In some ways we were moving at our slowest pace for some time and we knew we needed to make some changes. We adjusted the vision and it felt appropriate to rethink our roles too.
We spent about 3 weeks with the “Leo kicks Buffer into a higher gear across all areas” setup. I think it was a welcome change from everyone in the team, however right away something didn’t feel quite right for me.
Leo and I were both excited about his role being to help us move faster. I was happy to try and stay focused on figuring out where we need to go in various areas and with the company as a whole. The problem we found, was that it was almost impossible to clearly separate these two processes. If Leo was working with someone to try and set goals and keep to them, he inevitably had to make decisions which affected our direction.
It felt like with the new structure we were suddenly both involved in every decision. The goal of the new role for Leo was to speed things up, but with both of us discussing every decision, things were sometimes grinding to a halt, especially in cases where we didn’t immediately agree.
This put a lot of strain on our relationship as co-founders, and it’s probably the only time I can think of in the whole lifetime of Buffer so far where I’ve had some really tough conversations with Leo. It was exacerbated by the fact we were hitting some of our slowest growth months ever and both felt pressure to pick things back up. I was confused and needed to quickly figure out why it wasn’t working.
How we came to the current CEO/COO structure
In the first week of December we were in Thailand for our second company retreat. It was during our time there that Leo and I had a lot of lengthy walking meetings around Pattaya about the structure of our roles. We talked a lot. I couldn’t think of a more perfect setting for us to figure these things out. We’re both optimistic people and despite the tough conversations we knew we’d come to a conclusion about how things should work. We had gratitude for how lucky we were to be in Thailand and had built a company to a stage where this problem had arisen.
I’m the kind of person who likes to solve problems. I guess that’s why I naturally enjoyed programming (though I rarely code anymore). Therefore, I always like to try and talk things out until we can agree. As an introvert, however, I often do some of my best thinking and have inspiration when I spend time alone to contemplate. So, after several days of discussions with Leo, one evening I took to my room and started reading up everything I could find about the COO role.
I was surprised by how many different definitions of the COO role there were out there. This really confused me at first. For example, one person may say it’s the CEO’s job to motivate and manage the team as a whole and ensure execution of day-to-day tasks, whereas another person may say it’s the COO’s job to manage day-to-day running of a company and help the CEO have room to think on a higher level.
Everything became clear to me when I found this key insight:
"There is commonality across different businesses between the roles of CMO, CFO and most other executive functions, but not so with the COO, where the roles are hugely varied. Maybe the best way to think about it is that the COO does the things that the CEO doesn’t." - Nic Brisbourne
If you look at the job descriptions of various COOs, you’ll find that they could be completely different from each other, sometimes even opposing. The reason is that it all depends on the strengths of the CEO. It was starting to make sense to me that the best CEO/COO relationships are when the two are very complementary to each other. This got me excited since Leo and I have always found we excel in different areas.
"A COO’s value is designed to be complimentary to the CEO. The truth is that no CEO, no matter how experienced, can possibly cover the complex aspects of managing all the functions of a technology company. Its better to divide and conquer. By recruiting a COO, the CEO can focus on the aspects of the role that he/she truly excels at and enjoys the most." - Firas Raouf
So I got to work brainstorming all the areas of the company and which I felt confident about running myself. Once I did that, it became clear how Leo and I should work together. I hopped onto a call with Leo to explain my discovery.
What Leo and I do as COO and CEO
When I shared my learnings around the COO role and how we could work together, Leo was receptive to the adjustments and we were both really excited for the new structure. We’ve used this structure for the last three and a half months and it is working incredibly well.
The key thing we have done is to determine our key areas of focus and embrace the idea that we should not be the key person running anything. It was a key learning that if we’re running something ourselves, we’re not doing it as well as it could be done and we’re also neglecting other areas. So we aim to fire ourselves repeatedly and move to a position where we’re helping with higher level vision, coaching and we’re “being reported to”. This has started to work very well, and it feels like we’re moving faster than ever.
Here’s how Leo and I work together now:
For a while, and especially after the previous experience of stepping on each others’ toes, we tried to make these areas completely separated. Over time, we found there is a lot of natural overlap. Our advisor Hiten shared an analogy which helped us a lot (I’m paraphrasing here):
"Think of it like Batman and Robin. So if Product leads a project, it’s Batman and Growth supports with the right numbers and is Robin."
This is how we approach everything now. The Batman and Robin method helps us have one person who makes that final call, but we can both support each other too.
How do you structure how you work with your co-founder or business partners? I’d love to hear any thoughts, questions or advice you have!
Photo credit: Hans Splinter
In the last 6 months, we’ve quietly shifted the direction of Buffer. Our adjustment is now almost complete and we’re charging ahead with our new vision. It’s interesting to reflect on how we came to realize that a change was needed, and how we went about finding our new path.
The original vision
The earliest idea of where we wanted to take Buffer was that we aimed to be a sharing standard:
Our vision is to become a new sharing standard across the web and apps, and to set the bar for great customer support.
For us, the idea with this was to be a very widespread consumer product with a low price point. We had been inspired by Evernote and casually used the phrase “The Evernote of Social Media” to describe Buffer. Evernote at the time had tens of millions of users and its business model was super simple: an optional pro version at $5/mo.
In the beginning, we had a $5/mo plan and a $20/mo plan, in line with this philosophy. Over time we adjusted our price to $10/mo and dropped the higher priced plan. Interestingly, for some time we had a $100/mo plan and people very readily paid that to manage additional social media accounts and team members. At the time, however, we were entirely focused on becoming a widespread tool and decided we must stay simple. We ditched the higher priced plan and attempted to scale as a platform rather than adding more power to the product itself. If we wanted to be a button across the web and apps, it had to be a simple idea.
What we learned attempting our original vision
In some ways I wish we had perhaps realized sooner that our vision to be a sharing standard was not going to work. At the same time, we gained many benefits by pushing ourselves to be a widespread product used by many individuals and small businesses.
Growth slowed, conversion rates dropped
We made a lot of progress in becoming a sharing standard. We made partnerships with Feedly, Pocket, Echofon, Reeder, TweetCaster and many other apps and services. I believe these integrations are still incredibly useful for our users (I personally am using the Feedly and Pocket integrations daily).
One of the key learnings we had in fulfilling a large part of our original vision was that partnerships and integrations rarely give you distribution. A key part of this vision working for us was tied to the integrations leading to many new Buffer users. We certainly got a good number, however we always had much more success with signups direct from our own web and mobile apps.
Not only did we not get a significant number of new users from the integrations, we also observed a drastic drop in conversion rates (to active users and eventually paying customers) for people who came from 3rd party apps. In hindsight this is not too surprising, since these users are not in that app primarily to use Buffer.
The benefits of freemium
While we found many flaws in our original vision and eventually decided that we needed to make an adjustment, I couldn’t be happier with the result of that journey.
Luckily for us, generating revenue was always a key focus (we charged from day 1). Therefore, even though we focused on having a wide reach, we always looked at our conversion rates and cared about revenue. In the journey of growing to 1 million users, we grew to significant revenues, to the extent we could be profitable and not have pressure to raise further funding.
In addition to building a profitable business, we have a true freemium / SaaS scenario and scale to be able to grow by understanding user patterns and running a/b tests and other experiments. We have 2,500 new users every day and consistent conversion rates to our $10/mo awesome plan as well as $50+/mo business plans.
I’ve observed that as startups grow, they tend to move up market. They introduce more powerful offerings and charge more. They start doing enterprise sales. We’re even on this journey now. At the same time, it’s incredibly powerful to have a free or lower priced product and have a large top of the funnel. We’re lucky to have both, and it’s much harder to try to fill that room at the bottom later.
The valley of death
Something that’s become increasingly clear to me as I’ve traveled this path is that I think there is a dangerous middle ground between trying to be super widespread and mainstream (and monetizing via ads) and focusing much more on value and power (and monetizing via subscription payments).
The way I see it, is that if you want to monetize through ads you probably need 100M+ users. If you want to build a solid freemium offering you only need a few million users, if that. Pure SaaS and it’s even less. But if you build something that people won’t pay for directly and end up with only 10 or 20 million users, you might be in a tough spot.
We’re now completely focused on building a world-class freemium and SaaS product to solve problems around social media.
The new vision for Buffer
As a result of our learnings and reflection on the slowing growth, Leo and I had a series of conversations towards the end of last year and decided on our new vision:
The vision for Buffer is to be the simplest and most powerful social media tool, and to set the bar for great customer support.
When we decided to make the change, we chose to approach it in a lean way. We didn’t talk too much about it until it really started working. To begin with, we simply brought back higher priced plans and reached out to some key customers hitting the limits of existing plans.
Fast forward to today, we have over 1,000 business customers and it already contributes 15% of our revenue. I’m excited about our new path. We’ve found it is incredibly fun to work with larger customers who have real problems and a need for a powerful social media solution.
Have you made any key decisions around changing the direction of your startup? I’d love to hear about your experiences and learnings. If you have any questions about the journey we’ve had with Buffer or our new direction, leave a comment below!
Photo credit: takasuii
I’ve always found it interesting to think about co-founder relationships. I’ve been in a few myself, some which were not completely successful and then more recently working with Leo for the last 3 years has been an absolute joy. It’s fascinating to me how co-founders need to be different in many ways and at the same time have shared values they are aligned on. It’s a real art to find someone who you work well with and trust.
I recently watched a video of an interview with DHH from Basecamp and found the audience question on co-founders interesting and very in-line with my own experiences on what makes a good match.
Complementing each other in skill-set
"When two men in business always agree, one of them is unnecessary." - William Wrigley Jr
I think it’s super valuable to have different strengths as founders. I often see fantastic products from great engineers and product people, where I believe the product should be used by far more people. It’s probably because the founders are not naturally inclined to do marketing, and so keep working on the product.
"I see a number of startups where the founders are too alike. Either they agree on everything or even worse they do the same thing. Like starting a company with two programmers - I don’t think that’s a good idea. I think you need skills, and you need mentality, to complement each other." - DHH
In the early days of Buffer, I reached a point with the product where it had a couple hundred users and some paying customers, and I knew in my head that I needed to switch to marketing. There was validation that the product in the exact form it was in, was already useful to people. There was clearly more people out there who would find it valuable as well. However as a developer it was a real challenge to be effective at switching to marketing instead of fixing bugs or building out new features. Luckily for me, that’s when Leo came on board as my co-founder and had a massive impact since he was a great marketer.
It’s also useful to have different mindsets on the business aspects too:
"For me and Jason on skills, Jason was all about design and I was all about programming. So that was just a natural fit right there. On running the business, Jason is more of a risk-taker and I’m more conservative. I’m more about running the numbers and making sure everything’s alright, and Jason’s more like let’s just rip away everything and try something new and take a leap. I think you need both of those things to pull the business in the right way." - DHH
For me and Leo, we’re both scrappy and take the lean mindset. At the same time, Leo is probably more inclined to push something out of the door extremely early, whereas I like to be a little more calculated and logical and get the best balance of learning and not wasting time by building something out without validation, but still shipping something quite polished.
One of the most interesting ways Leo and I complement each other is on “doing” vs “reflecting”. I often joke that if Leo and I each have a daily todo list with 5 items on it, there is absolutely no question that Leo will get through his 5 tasks. For me, I struggle at times to get through everything. I work hard to be productive, however I also like to take time to reflect on the direction we’re going and ponder changes. We both aspire to be more like each other in this regard: I’d love to just crank through more, and Leo says to me he’d like to reflect more and sometimes realize not to do some tasks. We talk very regularly and help each other, and we end up at a nice equilibrium.
Aligned with each other on values and vision
"At the same time, you have to have some overlap too. Jason and I obviously share a lot of opinions about how to run a business and what is important and our values are incredibly alike, in terms of creating a sustainable long-term business that does well for both its customers and its employees. So you can’t just be polar opposites and expect that everything’s going to be daisy. There’s got to be overlap on important cultural values in the company, but outside of that seek as much diversity as you can." - DHH
The hard part of finding a great co-founder is that you want to sufficiently complement each other, but at the same time it’s vital to agree on fundamental values and what you want to do with the company. If one of you wants to flip the company within a couple of years and the other wants to make it their life’s work, it’s going to be difficult to agree on key decisions.
From an early stage it became clear that Leo and I were very aligned on many of the values which became the Buffer culture. I introduced Leo to How to Win Friends and Influence People and we spent countless hours discussing the principles and examples. Leo has always had tremendous gratitude for the opportunities he has had and is one of the most positive and happy people I know, and that was something I aspired to focus on more. I always enjoyed being very open and transparent about my learnings and progress and this came completely naturally to Leo too and he enjoyed pushing us further in that direction.
How did you meet your co-founder and what are the key ways in which you complement each other? I’d love to hear about your experiences
P.S. We need help with many areas of Buffer right now, to complement the existing great team. Check out our openings