I am an investor in 9 companies: How and why I started angel investing

Written on 19th February, 2018

A lesser known fact about me is that I have invested in 9 companies. It’s something I’ve not written about yet (other than a quick mention on my /now page). So here we are.

The first investment I made was in Kate Kendall and CloudPeeps. I became an advisor to CloudPeeps fairly organically, having known Kate for many years in the industry. Being an advisor, I had a chance to chat regularly and get to know Kate. I loved the product and her approach, especially the culture and community she was carefully crafting.

Then in December 2014, I got some liquidity by selling a small number of Buffer shares in a funding round, and so I was in a position where I could invest. The timing was perfect, as CloudPeeps were fundraising and I had been advising and making introductions to help with that.

I invested $10k in CloudPeeps, and since then have gone on to invest in 8 more companies.

How I think about the financial risk and opportunity of angel investing

It’s now over 3 years since I made my first investment in a startup company, and I’m yet to see any kind of return what-so-ever. I think it’s worth noting that investing in early stage companies is one of the riskiest forms of investment that you could make.

When I took liquidity in our Series A funding, I knew that I had the option to make some investments. I didn’t know much at all about investing my money. I never had a large amount of savings growing up and so it was never something I needed to know about. When I got the liquidity, I gradually educated myself about the various types of investments I could make, and I also started making my first investments in startups.

I think about ways to invest on a spectrum:

  • Low-medium risk: 401k / bonds
  • Medium-high risk: stock market
  • Very high risk: cryptocurrency / startup investment

While cryptocurrency has massive volatility, what makes investing in startups even more risky is that the investment is totally non-liquid. You can’t take your money out by choice at any time, you are tied to the trajectory of the company and the decisions of the founders.

It’s a well known fact that most new companies fail. Investing at the very early stages of a company, is certainly high risk high reward. It’s most likely that the company fails, but if it succeeds then the return could be high, because the investment will have been made when the company is very small.

I made a decision that I need to be comfortable losing all the money I invest into startups. This shaped my investment methodology. I am using other investment methods to try to grow my wealth. Angel investing is as much for personal fulfillment and what I want to contribute, as it is a way for me to make large financial returns.

Making investments for my own personal fulfillment

Since the earlier days of being an entrepreneur, I always had a dream that I’d like to one day help others through both advice and investment. One of the mindsets that has helped me to work through some of the tougher moments has been knowing that I can help other founders with those very issues.

I’ve also learned over time that helping others is one of the things that brings me the most happiness. I saw investing in startups as a new way to help others, with not just the financial investment but by being available as an advisor to portfolio companies.

And through my investments I am able to be involved in the early stages of companies again, something which I love. Buffer is now 7.5 years old, 70+ people and doing over $17m per year in revenue. It’s a very exciting time for us, but definitely a little different from the earliest stages.

Trying to make a small positive impact with my investments

Something I’m passionate about with Buffer and as a personal philosophy, is to try to make positive changes in the industry through the work I do. With Buffer, this is through the product and the way we operate the company. We believe that we have the opportunity and the potential to push forward how companies are run for the better.

One key example of this within Buffer is remote working. We have a fully distributed team, and this means that everyone in the company has much more freedom than they would in an ordinary organization. Team members can move for their own fulfillment or for the needs they have. Some team members have been able to travel a lot, others have had the comfort in being able to move across the country or the world for their spouse’s career. And some are able to work in their home country, where they would otherwise need to move away to make a better salary for their family.

Other examples of our efforts to contribute to a better future are through our transparency (making all of our finances, salaries and more transparent), and we also recently made our first charitable contributions as a company.

I’ve also been inspired by Clif Bar and Patagonia, whose founders have shared the idea that when we make an investment in something, be it with our time or with funds, we should challenge ourselves to think beyond desiring a financial return on investment.

At the end of the year I want to look at our balance sheet and see that we were good stewards of our business—a company that we are preparing for a long-term future. We choose how we define shareholder value, and we include product integrity, our people, the community, and the earth in the balance sheets. - Gary Erickson, Clif Bar

The return on an investment can be in the form of a resulting meaningful contribution to society or a community, through the investment helping to solve inequality, or by helping to solve environmental issues.

By making investments in startups, I am able to make a small impact on other companies too. I can help founders think through less usual and more impactful ways of running their company. I can be an investor who advocates for companies not just generating a financial return but also doing good in the world.

Helping founders achieve freedom and a maintain healthy mental wellbeing

Something I believe is not talked about or written about enough, is the toll that building a company can take on you as an individual. I’ve been through some very dark periods with Buffer, and I’ve hit some real lows along the way. I’ve been lucky to have a very caring team and family, and to be in a position where I was able to get help too. Working through challenges in this way has allowed me to have a much more balanced and healthy mindset to growing Buffer.

Unfortunately, I believe that as much as investors often try to be advocates of founders speaking up and sharing their challenges, often they are an additional burden in difficult times. Many investors don’t take a long-term approach that allows them to believe that helping a founder through hard times will ultimately give the best return.

All too often, I’ve also seen founders become constrained and lose freedom as their companies grow. They may have grown their company to several million dollars a year in revenue, and created fulfilling jobs for dozens of people, but they are overworked, and when they reach life milestones such as having a child, struggle to have time or take money out of the business to afford a better home.

I believe founders deserve better, and investors should support freedom and making a financial return along the way. I am a big proponent on founders maintaining freedom for themselves and their team, and taking a longer term sustainable approach to startup liquidity, instead of sacrificing health, finances and relationships for some hypothetical future exit.

With Buffer, I’ve been lucky to see a few different sides of startup investment. We have both angel investors and venture capital firms who have invested in Buffer, and I’ve seen a variety of styles with which people choose to operate. By being an investor, I can be a voice at the table of companies, to push for care around these issues and to provide balance compared to more traditional approaches. I’ve decided that beyond obvious bad behavior, I will always be on the founders’ side.

My process for making investments

Some angel investors have had a large exit with a previous startup, or had some other event which has put them in a position of a lot of wealth. I haven’t sold Buffer, and have no plans to anytime soon. By selling a portion of my shares, I’ve been able to get some liquidity, however I don’t have the level of wealth that other angel investors may have. In addition, since I am still running Buffer full-time, I also don’t have a lot of time to put into my angel investing activities.

Therefore, my process for making angel investments is more hobby than professional, and one optimized for the little time I have to invest. One way I have made things easier for myself is that I have, so far, always invested $10k. This is a hard and fast rule I have given to myself and communicate with companies I am in discussions with.

I am aware from my own experiences, that $10k doesn’t go too far for a startup and that it may not be desirable to have a small investor take up another slot on the cap table. I have found that with the ups and downs I’ve been through, many founders are excited to have me on board and get the additional advice beyond my investment. I feel lucky to be able to invest in the companies that will have me, and I will not be disappointed if I am turned down for being too small of an investor.

While I don’t have a lot of time to do extensive analysis, or treat my investments as a professional endeavor, I enjoy talking with founders and helping to solve problems. I therefore make time to be able to get on a call, or answer emails for founders.

Another decision which I’ve so far made, is that I will generally always do follow-on investment, when I can. If I can afford it, I will double down my investment when I get a chance in future rounds. My thought process on this is that since most companies fail, the ones that go on to raise more funding are more likely to be gaining success (this is definitely not a completely water-tight correlation, but I think it works well enough). This allows me to maintain my equity stake in a company as it raises more funding and I would otherwise be diluted.

My startup investment portfolio and timeline

I made my first angel investment in December 2014, and my last one in August 2016. Here’s the full timeline and my portfolio:

I invested $10k in all of these companies except for a couple which were in Euros and Pounds, where I invested a little more to make it 10k in the corresponding currency.

You may notice that I made all my investments in a 1.5 year period, and I’ve not made any in the last 1.5 years. There are a few key reasons for this. In Summer 2016, we had cashflow issues at Buffer, and as part of working through it I voluntarily reduced my salary by 40% until early 2017. This was a key reason I stopped making further investments.

In 2017, we had a number of big changes at Buffer, including my co-founder and our CTO leaving the company. I got heads down to help the company through the transition and I also made a decision to invest $250k of my own money into buying Buffer stock and providing liquidity to a couple of former team members. This has put my angel investing activities on hold for the time being.

Looking ahead

Although I have been in a holding pattern in terms of making further startup investments, I’ve very much enjoyed being an active angel investor so far. It’s been fun to be an active part of the founders’ journeys. I have so much more to learn to become a better startup investor and advisor, and I’m excited to continue this journey further. One of the key things I’ve taken away from this process is that if you don’t know much about something, one of the best ways to learn is to dive in and start doing it.

I have been lucky to have success with some of my other types of investments, and Buffer is doing great right now, so I think I will soon consider becoming more active in advising and making further startup investments.

Have you ever thought about investing in startups? Are you an active investor? I’d love to hear any thoughts you have on this article in the comments below.

Photo credit: Vitaly

5 varieties of remote working in companies

Written on 13th March, 2017

I've recently found myself reflecting a lot on being a distributed team, and the nature of a company where the team works from remote locations to accomplish our work.

Scaling remote working has been a challenge as the team has grown. Remote companies are still relatively rare, and therefore all of us who are choosing to have a remote-friendly culture, need to both:

  • work through the normal challenges of growing as a company and as a team
  • also put time into figuring out how remote can scale, where there is no real pre-existing playbook

One of the significant commitments we've made recently at Buffer, is to approach our company growth goals in a long-term fashion, staying true to our culture of remote working. This means we deliberately make time to try to scale remote working, even if this may at times feel it comes at the expense of short-term financial growth.

It is my belief that working to develop a great remote working culture is an investment that will pay dividends for decades to come. If we can make this work over the long-term, we set the company up for many significant advantages and great freedom for us as a team.

The levels of remote working

In my reflections, I came to the realization that remote working is a scale, and there are actually a number of different options along across spectrum from "not remote" to "fully distributed".

1. Not remote / office-based culture

Obviously at the far end of the spectrum we have what is today perhaps the most typical working environment for companies. In this model, you have your whole team in one or more offices.

This means that you typically have set down working hours (strict or loosely enforced). You will work from the office all day, and not have too much flexibility in your day, nor will you have the option to choose the work environment you enjoy and find yourself most productive within.

Of course, office-based environments are also awesome for a whole bunch of reasons. You more naturally have close bonds and friendships forming. You can whiteboard and brainstorm, which can be very productive. If you have people who are junior in their role, they can very readily and easily get help so they don't get stuck.

2. Office-based with a work-from-home option

Some companies which operate from a single office, have started to give team members the option to work from home one or more days per week. This is a great start, and perhaps a perfect way to start to experiment with a remote working culture.

This small degree of remote-friendliness will already test the culture and require a few key changes to how work is done within a team. For example, those days that team members are working from home, the team will need to mostly communicate through email, chat tools, or some other means than the face-to-face methods which can be relied on without thinking about it in an office environment.

One key challenge when you start to experiment with this setup will be avoiding the people who work from home feeling left out of discussions that lead to key decisions. When you have the majority of the team in one place and a few people not in the office, it's easy for those people to feel like second class citizens.

3. A remote team, in a single time zone

This is where this start to get more truly remote. In this category you'll have companies which are more truly remote. However, some remote companies still choose to have the team mostly in one time zone, or very few largely overlapping time zones.

This is a truly remote setup, so the way work is done certainly is different from a team based within an office. Text-based communication and collaboration tools will come in here.

At the same time, in this setup, you still have a lot of hours of overlap, if not full overlap, with everyone in the team. So at least you can rely on someone being available when you need to get work done. Therefore, a lot of the day-to-day work can still be done in a synchronous fashion and work well.

4. A world-wide remote team spread across numerous time zones

A step further is to have a team where everyone is spread across different time zones. This means that asynchronous collaboration becomes even more vital. You'll likely just have a few hours of overlap with other people in your team, and so this setup requires a little more structure to make communication and collaboration efficient.

Sometimes companies set up this way, will choose to concentrate certain roles in the same time zone. Other times, it will be a completely location-independent setup. In either case, you generally have team members staying permanently in their location, for a long duration of time. So you can at least have some consistency of the setup of each team, and can set up some forms of synchronous communication at the times of overlap.

The challenges with a fully remote setup like this are numerous, however there are also many benefits. One key one is around-the-clock coverage of customer support or engineering.

5. A fully distributed team with nomadic team members

The most extreme case of remote working, in my mind, is a fully remote team where some of the members of the team are nomadic and traveling.

Since Buffer's distributed team setup is based around our vision to create a workplace of the future, and also around our value to live and work smarter, this is the ultimate level I am currently striving for us to reach.

Currently, we see some challenges in reaching this level of freedom for team members, and a collaboration system that can be efficient with this setup. A key milestone I believe of this level will be that work continues regardless of people moving locations. Of course, moving to a new place can affect productivity and this is for people to be mindful about. However, I do believe there is a way that collaboration can happen, where aside from those productivity challenges, work can happen in the exact same way, regardless of location. This is what is needed to truly be able to work efficiently with nomadic people in the team.

I believe open source can be a great inspiration for the kind of asynchronous collaboration that is needed for this setup. Synchronous chat tools are problematic. At the same time, to cultivate culture and create bonds, synchronous chat tools and video calls can be effective here too. The key, it seems, is to separate "how work happens" from those synchronous communications.

Do you do remote working at your company? Which level are you at, or do you see yourself a different level I've not covered here? What do you think is worth striving for? I'd love to hear from you in the comments.

Photo credit: ricardo

The Power of Company Retreats: Thoughts after the 8th Buffer Retreat

Written on 9th March, 2017

By now we have a fairly long history of doing retreats at Buffer. We’re now a 75 person team, and we just wrapped up our 8th company retreat in Madrid, Spain. Here’s a quick history of retreat locations, timeline and size over time:

  1. San Francisco & Lake Tahoe, U.S.A. (August 2013, 8 people)
  2. Bangkok & Pattaya City, Thailand (November 2013, 10 people)
  3. Cape Town, South Africa (April 2014, 16 people)
  4. New York, U.S.A. (September 2014, 25 people)
  5. Sydney, Australia (February 2015, 26 people)
  6. Reykjavik, Iceland (July 2015, 31 people, 40+ with partners & family)
  7. Hawaii, U.S.A (February 2016, 67 people, 90+ with partners & family)
  8. Madrid, Spain (February 2017, 73 people, 100+ with partners & family)

It’s been a wild ride for us at Buffer, to this point where the regular company retreat is a very clear part of our culture. Each retreat has felt a little different, and the nature of the retreat evolves as the company grows and our vision and culture advances.

The purpose of a retreat, from a CEO perspective

As CEO of a 75 person remote team, I see the retreats as an essential part of the work we do together. I firmly believe that if we would operate the company without these regular face to face gatherings, we would be less effective and feel less connected.

When we were a team of less than 30 people, the retreats felt like they could be a productive day-to-day work time for us. A shift towards working together, but continuing with the projects we happened to be working on. In addition, when we were smaller, we would do the retreats more regularly (around every 4–7 months). By doing them more frequently, and having a smaller team, the retreat itself was not as much of a monumental event, because it would come around again quite fast. Today, we do it less frequently: this retreat was 1 year after our last one in Hawaii.

As a result, today our retreats serve less of a purpose of immediate productivity, and are more geared towards long-term productivity and meaningful connectedness of the team. We focus all of our sessions throughout the week on brainstorms and higher level discussions that will have an impact for months going forward.

As CEO, I find that beyond the opportunity I have to provide leadership, set vision and create alignment, the real purpose of retreats is to listen. I try my best to float in and out of different groups, whether for lunch or dinner, in sessions during the day, activities on off days or drinks in the evening. In these very different groups, I am part of the conversation but also sitting and listening, and trying to take a lot in. Of course there will always be blind spots for me as a leader, and so I lean on the leads I work with too, but I try my best to be present and soaking up the joys and frustrations that I hear expressed. Each retreat is an opportunity to take this in, and try to act to improve our culture and working processes further.

Timing of a retreat

The context within which a retreat happens is a key component of how it will feel, and the goals we try to have in mind.

2016 was a difficult year for Buffer, we had layoffs and then at the start of this year, my co-founder Leo and I came to the conclusion for him to move on from Buffer. Our CTO Sunil also decided to leave the company at this time too. A lot of change for a single year. It’s been rocky. We’re now in a great position and have rebuilt our cash reserves to over $2.4m since the low point of $1.3m around our cash flow crisis.

As a result, at retreat it was important to acknowledge the past year. Morale is still in recovery from those ups and downs, and the team gathering in Madrid could not have come at a better time. We had sessions in which people could open up about those feelings, and we also had a lot of serendipitous conversations around the future.

All in all, I think we did a good job of acknowledging the challenges, and also sharing the excitement with each other about our future. We shifted towards this throughout the week, and almost all teams focused on their vision for 2017. I shared a lot of my own ideas around the company and product vision going forward, and we have a huge number of opportunities based on our solid foundation of products, customers, culture and profitability.

Being a key part of retreat as an introverted CEO

I am lucky to have an incredible team I work with on retreat, and this year Stephanie really took on the task wholly and I didn’t need to be too involved in the planning. At the same time, I am leading the retreat in many ways, I officially start it and I run many sessions. Especially since retreats are not cheap (our budget for Madrid was $400,000) I strive to reflect on how we get the most out of the time and take a lot of personal responsibility for that.

The retreat itself is a week packed with so much energy and happiness. We are all incredibly excited to see each other after a year apart, and this year around 25 people were on retreat for the first time, meeting almost all the team for the first time.

I am an introvert, around 85–90% introvert vs extrovert in most tests I take. In the past, this has at times led to debilitating situations after long periods of social stimulation. Around 4–5 years ago, I started to understand myself much more clearly, and I now find in general I can take the action I need to in order to feel recharged most of the time.

During retreat, I took a 20–45 minute solo walk each day during the week. At an appropriate time in the afternoon between sessions, I’d just head out of our work space and go walk up the nearby hill. After a day with a lot of social interactions, my mind can feel clouded and I find it hard to think and articulate clearly when I am drained. It’s always fascinating to me how quickly I can recover from this and feel energized, sharp and ready to be amongst people again. A few times this was essential was before my fireside chat with the community at Google Campus Madrid, before our Sunday welcome drinks and before our Wednesday evening team dinner.

I have found that it absolutely is possible for me to enjoy the whole week, as long as I remember to be aware of my energy levels and take care of myself.

It’s been a hugely rewarding and energizing week. I am pumped for the rest of 2017, and I am confident we’re going to achieve some great things together. If there’s any single takeaway for me from the retreat, it is the reminder that I get to work with the best team on Earth.

Photo credit: Nico Trinkhaus

3 reasons you shouldn't outsource your startup, and what to do instead

Written on 21st May, 2015

One of my favorite things to do is to help others who are at an earlier stage of the startup journey. I had a lot of false starts before Buffer. I enjoy sharing my lessons from those failed attempts, and I also enjoy getting my mind back into those early days challenges, now that Buffer is almost 5 years old.

In the last week, I’ve had 5 sessions (typically around 30 minutes, in person or via Hangouts) where I’ve tried to help someone. I was surprised to hear the same challenge come up in 3 of those 5 sessions this week, so I thought it might be a worthwhile blog post topic too.

The thought process of outsourcing your startup

I think if you’re not technical and can’t code, it’s very natural to think that you can’t progress much with your startup idea unless you find help. Often the first thought is to either find a technical co-founder, or to outsource building the minimum viable product to a firm or a freelancer.

In my experience, both these options are almost always the less optimal approach for succeeding with your startup as quickly as possible.

Here’s why I think you shouldn’t outsource your startup:

1. Your goals and a freelancer’s goals are completely misaligned

If you think about it, the goal of a freelancer or a creative agency or firm is to serve many different clients, and to ultimately make money. Your goal when you have a startup idea is to reach product/market fit and make something that can get traction.

A big problem with these 2 differing goals is that the successful path for a freelancer to reach their goal is very different to the successful path for startup founders to reach product/market fit.

One of the easiest problems for a freelancer to encounter is scope-creep of client projects. If the freelancer or agency is setting a fixed price for the project, they need to take many steps to ensure that the scope of the project doesn’t grow beyond what was initially budgeted for. This means that in the beginning, they are going to want to set down a very defined specification of what this project involves. A freelancer’s goal is to make money and a key ‘tool’ for success is to be quite exhaustive with defining the initial specification for a project, and to avoid changes to the spec along the way if at all possible.

As a startup, your goal is to reach product/market fit. There’s a great insight Matt Mullenweg once shared which really puts into perspective why as startup founders we should launch as early as possible:

“Usage is like oxygen for ideas. You can never fully anticipate how an audience is going to react to something you’ve created until it’s out there. That means every moment you’re working on something without it being in the public it’s actually dying, deprived of the oxygen of the real world.”

Therefore, the ideal approach for creating a successful startup is to put it out there as soon as possible and then iterate from there based on the new information that comes from usage and from doing customer development. This is almost completely at odds with the approach most freelancers will want you to take. Not only that, most freelancers or agencies are building websites for more established or more predictable businesses and they often don’t understand the nature of startups.

It’s not that a contractor or agency is doing it wrong, they’re just optimizing for their most common type of client project: to create a website. For example, it might be a website for a restaurant, a coffee shop, or a golf club. In the words of Eric Ries, these are ‘known problem, known solution’ situations. We know what a restaurant website should do. It should have a menu, show you where the restaurant is, etc. With startups, we live in a world of ‘unknown problem, unknown solution’ situations. We don’t know whether our new idea will work. It takes a whole different approach, and I think this is almost always misaligned with the way a freelancer will approach things.

2. It gets you into the wrong mindset of what it takes to get a product off the ground

Very much related to the first challenge, I believe that if you are thinking about outsourcing your startup, you likely already have the wrong mindset about how to create a successful startup.

I’m lucky to have been coding since I was around 12. When I got into startups, I was lucky to have that part of the equation taken care of. What I realized after a few years in the game was that my technical ability blinded me from what it takes to make a successful product. I just kept building, and that’s not the main part of succeeding with a startup.

I think that often if someone is thinking about outsourcing their startup, they’re also under the false impression that the key to succeeding with their idea is to get it built.

The idea itself is often way off, and most likely won’t work once you put it out there.

What it takes to create a successful product is eliminating all the unvalidated aspects, and finding something that users or customers truly want, that has product/market fit and can get traction. The interesting part about this, is that coding is actually not at all required to achieve this.

It’s my belief that, especially today, you can create a fully working (albeit potentially somewhat manual) version of your startup without coding at all. You can use tools such as Wufoo, Unbounce, WordPress, Google Forms, and other things to string together a set of interactions. You can fill in the gaps with hustling and manual work yourself. It won’t scale, but ironically that is the key to initially growth and understanding what is working and what isn’t.

Without coding at all, I think you can have an early (far from perfect) product and even start to get traction if you iterate and solve the unvalidated aspects of your idea. Once you start to get traction, so many doors will open up for getting help to code the product and make it much more beautiful.

Any decent coder is tired of hearing an idea guy come along and try to get them to build their startup. On the other hand, a decent coder will be extremely interested by a startup put together with no code that is getting really good traction. That’s something they can have a big impact on and has already been shown that it has huge potential.

3. The founding team should wear every hat

The other belief I have for why you shouldn’t outsource your startup is: the founding team should wear every hat. Here’s why:

  • it gives you the mindset that you can make anything happen, you just need to figure out the hacks and shortcuts to do it with your current capabilities
  • you retain full control over all parts of the process and can adapt and iterate super fast
  • when you reach the point of hiring people, you’ll know the difference between someone great and someone not so good
  • you’ll have a level of passion across many different areas of the startup. That can more easily help you be great at multiple things as you grow. It’s hard to hire passion and hard for someone else to thrive in something the founder doesn’t get excited about.

Therefore, I highly recommend you and your co-founders do absolutely everything in the beginning. In the early days, between the two of us Leo and I did development, design, database and sysadmin work, customer support, marketing, and more. I even built the first version of the Android app before we invited Sunil to the team to take it over. There’s almost nothing we do at Buffer now that myself or Leo haven’t done in the early days of the company. As a result, I get super excited about how far we can take things across all areas of the company, and I can speak on a deep level with anyone in any area.

What to do instead

I honestly believe that building your product yourself is the most optimal and in fact the fastest path to creating a successful startup.

It might seem counter-intuitive that building the product yourself could be the fastest way to success, when you don’t even have any coding ability at all. The thing is, I’m not talking about coding - I’m talking about building your product. In any way that you can. That could mean zero coding, or it could mean picking up things here and there (which I think is great, too).

The reason I think it’s the fastest path is that I believe you’ll struggle to find a great technical co-founder if all you have is your idea. And, I think if you work with a freelancer or agency, it’s unlikely you’ll have a working relationship that lets you cycle through the build-measure-learn loop and iterate towards product/market fit.

So, my recommended approach is to hack it together yourself, and at the same time keep meeting technical people in your local startup community. I believe there’s an inflection point where what you have is attractive enough for a technical co-founder to jump on board. If you don’t have a technical co-founder (or someone technical willing to join as first employee), I think you just keep hacking and doing customer development and validating your assumptions, to create something that gets traction.

What are your thoughts on creating a startup if you’re not technical? I’d love to hear from you in the comments!

ILO in Asia and the Pacific

11 cities in 3 months: The highs and lows of digital nomad lifestyle

Written on 6th May, 2015

In December, my friend and co-worker Brian casually mentioned to me that he would love to go traveling and explore Asia. I love Asia. I lived in Japan as a kid for 3.5 years, and I lived in Hong Kong for 6 months in 2012. It was a no brainer for me to jump on the opportunity and travel around Asia with Brian.

At Buffer, we’re a fully distributed team. We’re currently 31 people spread across 22 cities. We all work remotely, and it is a lot of fun. This also gives us the freedom to choose to be anywhere in the world, and to move or travel if we wish. Everyone is trusted to balance this with their productivity and getting the results for the teams they’re part of.

Being a fully distributed team, we still believe it is super important to meet and spend time with each other face-to-face. As a result, we have team retreats at different locations around the world every 5 months.

In December, our next upcoming retreat was Sydney. The result was that Brian was interested in traveling around Asia, I was keen too, and we had our Sydney retreat coming up. So we decided to spend a month in Asia and ‘travel’ our way to Sydney.

And that’s how it all started for me.

How an idea to travel around Asia turned into being a digital nomad in 11 cities in 3 months

I spent some time thinking and decided to take the plunge and give up my apartment in San Francisco and become a digital nomad with no fixed location. I had been in San Francisco about a year and was craving exploring again, having done a lot of travel in the 4.5 years since starting Buffer (which even contributed to us becoming a distributed team).

It just so happened that I needed to obtain a new US visa (I’ve obtained it now and have the O-1 visa) and I was required to go to a US consulate outside the country to get it, so I decided to make that one of my tasks while in Sydney.

I also had been lucky to be invited to speak on a SXSW panel which got approved, so that was a definite destination for the middle of March in my travel plans. I’ve found through my travels that I really enjoy breaking up long flights, so I chose to spend 2 weeks in Santa Monica to break up my travel to Austin for SXSW. Knowing that I’d only spend a few days in Austin for SXSW, I chose to spend a week in Houston right afterwards to get a more full experience of Texas (my first time in the state!).

All these factors combined, here’s where I ended up spending my time during the first 3 months of 2015:

  • San Francisco, California (May 2014 → Jan 2nd)
  • Tokyo, Japan (Jan 3rd → Jan 11th)
  • Seoul, South Korea (Jan 11th → Jan 18th)
  • Singapore (Jan 18th → Jan 27th)
  • Jakarta, Indonesia (Jan 27th → Jan 28th)
  • Singapore (Jan 28th → Jan 31st)
  • Sydney, Australia (Feb 1st → Mar 3rd)
  • Santa Monica, California (Mar 3rd → Mar 14th)
  • Austin, Texas (Mar 14th → Mar 16th)
  • Houston, Texas (Mar 16th → Mar 21st)
  • Honolulu, Hawaii (Mar 21st → June/July)

I spent time in 11 cities in 3 months, and stayed in 14 different places (2 hotels, 11 AirBnB apartments, 1 friend’s place).

Here’s how that looks on a map:

Why I decided to become a digital nomad again

The last 5 years have included a lot of travel for me. Here’s a rough timeline:

  • October 2010 - July 2011: Birmingham, UK
  • July 2011 - December 2011: San Francisco
  • January 2012 - June 2012: Hong Kong
  • June 2012 - August 2012: Tel Aviv, Israel
  • September 2012 - November 2013: San Francisco
  • December 2013: Traveling around Asia
  • January 2014 - March 2014: San Francisco
  • April 2014 - May 2014: Cape Town, South Africa
  • June 2014 - December 2014: San Francisco

As a result, I’m certainly not new to the idea of traveling. At the same time, I had been pretty settled in San Francisco for most of the last 2 years with some traveling around our team retreats. To give up my apartment and become a full digital nomad was an extra step. Here’s what made me take that step:

I feel like there’s so much to see, and I want to explore more while I’m (somewhat) young and single and have the flexibility

I started Buffer when I was 23 and I literally felt like I’d live forever back then, and that I don’t age. Having worked on Buffer for almost 5 years, I’ve realized that is quite a long time, and I’ve been getting older during those years. I expect that naturally I might be in a position some time in my thirties where I’ll want to settle in one place. In the meantime, I feel like there is so much of the world to explore, and I want to get out there and see it.

I have the opportunity to be an example of a whole new way of living your life

“Observe the masses and do the opposite.” - James Caan

A theme for my life for the last 5 years while building Buffer has been to always take the path less traveled, both personally and as a company. That’s how we ended up choosing to be super transparent, work as a distributed team, do a very unconventional $3.5m round of funding, be self-managed with no bosses amongst other less traditional choices.

Therefore, I felt a strong urge and that I might regret it if I don’t take this opportunity to become a digital nomad and be an example of a whole new way of living. It’s currently very rare to live in this way, moving around the world and working, with all your belongings in a single bag. Not only is it already rare to be a digital nomad, it felt less common still to be a digital nomad as part of a larger team with VC funding. I felt like it could be great for me to be an example of this being possible, and to explore it and share my learnings. Of course, it’s a lot of fun too.

I wanted to try truly experiencing solo travel

In my many travels in the last 5 years, I’ve always traveled with others (usually my co-founder Leo) other than one trip to Asia. I had read a lot about the joys (and the challenges) of solo traveling and I wanted to experiment with it. I found myself in a position where Leo was interested in travel, but not until later in the year, and he was focusing on building himself into communities more in San Francisco (something I admire, and will later describe, is a challenge I have).

The situation posed the perfect chance for me to try solo traveling. I felt especially excited as an introvert who feels quite happy to be alone. Solo traveling felt like it provides the perfect balance of being able to always find the alone time I need, but also being very incentivized to get out and meet new people myself, since I don’t have someone I know to rely on for my need for socializing. I actually find it exciting and much easier to meet new people when I’m by myself.

Some of the high points and successes in my 3 months of travel

Looking back, it was an incredible 3 months, a period of time I think I will long remember. Here are some of the high points:

1. I spent a month traveling with my friend and co-worker Brian, it was so much fun

If you have the opportunity to travel with a friend, be sure to take it. I was already great friends with Brian, but I think traveling around Asia with him for a month really gave us a chance to get to know each other even better. There were so many fun things we experienced together, like a traditional sumo wrestling practice, getting drinks with Japanese and struggling with the language barrier, traveling out to the North/South Korea demilitarized zone, and many more. I think we’ll both always look back on and laugh about some of those awesome times. What’s more, I think it makes our working relationship better too.

2. Experiencing some of the top cultural landmarks and sights in the world, all in just a few months

“A new psychology study suggests that buying life experiences rather than material possessions leads to greater happiness for both the consumer and those around them.” ScienceDaily

On the whole, I worked a normal week most weeks, and I did all of my travel between places and relocating to new accommodation on weekend days. So, I maintained a decent level of productivity (more on that later). Despite that, I had the incredible chance to fit in a crazy number of experiences into the 3 month period.

In the 3 month period, I had a chance to experience some absolutely incredible sights. The view from the Tokyo Skytree was awesome. I visited several temples in both Tokyo and Seoul. I had dinner at a ninja themed restaurant. I had drinks on top of the Marina Bay Sands in Singapore. I experienced Ludovico Einaudi in the Sydney Opera House and saw a movie at an open air cinema with a view of the Opera House and the Sydney Harbour Bridge. I went surfing at Bondi Beach and Manly Beach in Sydney and at Waikiki and Diamond Head in Hawaii. I went for evening walks along Santa Monica beach. I ate breakfast in Beverly Hills and saw the Hollywood Sign. I experienced the SXSW conference and had dinner with Eric Ries, Tim O’Reilly and others in Austin, and I went to a Rodeo in Houston. And that’s cutting the list short.

I’m very aware how lucky I am to experience all of this. Many days I wake up and can’t quite believe it. I would guess that for many, this could be a list of things you’d see in a lifetime. It was truly a highlight to see so much in such a short space of time, and kept me energized.

When we did our $3.5m funding round at the end of last year, Leo and I were lucky to each sell a small portion of our shares and receive liquidity. I’m particularly happy that so far I’ve spent zero on any substantial new material possessions, and the only spending I’ve done has been on travel and experiences, as well as some investments. It’s early to tell, but so far this feels like one of the best uses for money. That doesn’t mean I’ve spent a lot on travel or these experiences. I believe this kind of travel is less out of reach than many people think.

3. Meeting lots of new people and catching up with friends

The cool thing about being in a new place is that you can’t help but meet new people. I find that I have this energy and excitement whenever I set foot in a new city, I feel like just the way I walk around with that extra curiosity and enthusiasm makes me more likely to get talking with people. I also find I’m more eager to reach out and meet people, whether by Tweeting that I’m around, or by meeting people through an existing friend in the city.

It was so much fun to catch up with old friends in almost all the cities I was in, and through those people meet new friends who I will stay in touch with for years to come. And one thing I’ve found in the past is that we live in a time where many people travel, and so it’s not at all out of the question that I’ll be hanging out with some of these people in a completely different city in the future.

4. Keeping up my gym routine while traveling

One of the things I was happiest about while traveling was that I almost completely kept up my gym routine. I found an awesome Gold’s Gym in Tokyo. In Seoul I struggled and found that there aren’t too many gyms, but once I arrived in Singapore I was eager to get back to my exercise routine and signed myself up for a 2 week pass at Fitness First and went several times a week.

All in all, I had 31 gym sessions during the 12 weeks, which is an average of about 2.5 sessions a week. I generally aim for 3-4 sessions a week, so this felt like a pretty good effort and outcome amongst all the challenges of being in a new place, finding a gym and having so many other things I also wanted to do and see.

In the last couple of years, I’ve generally focused solely on strength training, and enjoyed that a lot. In the last 3 months I also started doing some cardio again with a little running and more recently some high intensity interval training through tabata sprints. I added cardio and some bodyweight exercise to my strength training. I’ve been working towards achieving a muscle up for several months and went regularly to the outdoor gym at Bondi Beach in Sydney and continued my practice and finally achieved my first muscle up at Original Muscle Beach in Santa Monica.

5. Being in a new place and experiencing different cultures made me more open minded again

One of the things I didn’t anticipate, but in hindsight makes complete sense, is how much traveling would affect my interests and focuses. It’s something I’ve grown to love and crave traveling for.

For example, when I was in Japan, I naturally got very interested again in improving my Japanese, and I was able to practice it quite a lot (I lived in Japan for 3.5 years as a child, and tried my best to keep it up by studying it for 3 years alongside my Computer Science degree, but have let the language slip away quite a lot).

Another thing that happened in Japan was that I had the chance to meet a lot of Japanese Buffer users, and I realized how important localization might be for us to implement. I then proceeded to propose a task force within the team to work on localizing Buffer (as an update, that task force was put on hold to build Buffer for Pinterest, and may continue soon).

A final example is that when Brian and I were in Seoul, we visited the North/South Korea demilitarized zone and I was very motivated to learn about the history of Korea while I was there. I read Nothing to Envy: Ordinary Lives in North Korea, which I thoroughly enjoyed and found fascinating, and watched a couple of TED talks (here and here) by North Korean defectors.

I feel super lucky and find it very fun to learn about topics like this while also experiencing the actual place where the events happened.

6. I did a lot of speaking events while traveling, I was happy to be able to help many people this way

One of my favorite things to do is to be able to give back. I’ve written before that I’ve found helping others brings me a lot of happiness. In addition, as I’ve been lucky to be part of Buffer growing more successful, I’ve also experienced growing requests from people asking my advice on things. It’s got to the point where I don’t have the time to respond to every request, which is something I struggle with since I’d love to help everyone.

One great way I’ve found to scale my ability to help people is through speaking events, blogging and other ‘one to many’ methods. Additionally, I found that being in Asia and having only a week in each place, setting up some events was one of the best ways to be able to meet everyone who was interested in speaking to me.

The other key thing that came to my mind in the weeks up to leaving for the trip was that as a fully distributed team, one of the areas of the world where we have the least people is Asia. As a result, I think it can be a little more lonely for team members in that timezone, and also means as a company we’re less open minded to some of the cultural differences both on a team dynamics and a market level. I decided to take the opportunity to try to spread word of Buffer, and ended up with quite a solid schedule of speaking over the few months:

  • Ad-hoc Buffer meetup in Tokyo
  • Fireside chat in Singapore
  • Fireside chat at StartupLokal event in Jakarta
  • Speaking at SaaSBusinessAsia conference in Singapore
  • Buffer Sydney meetup fireside chat event with Leo
  • Speaking on Open Pay panel at SXSW in Austin

It was a lot of fun to speak at all these events and meet hundreds of people through them.

As an introvert, I have to be quite mindful of my own energy levels when I’m speaking a lot, and also aware of how much time it takes me to feel well prepared for speaking events. I generally try to do fireside chats if it’s a more ad-hoc event, since I find those a lot easier to do on the fly and still feel they’re providing a lot of value for people. I loved doing all these events, however I think in the future I might not pack as much into a short space of time, since I think it was somewhat overwhelming at times and I think it impacted how productive I could be with all the other tasks I had going on at Buffer during that time.

The biggest challenges of being in 11 cities in 3 months, and the digital nomad lifestyle

A key reason I wanted to write this post and document the experiences I had while they’re fresh in my mind, is that despite having the incredible privilege to travel across 3 continents in 3 months and have some massive highs, there were in fact some real challenges and low points. I feel it’s important to share that side of the story, and hopefully it can be interesting and useful for somebody.

1. At times my productivity suffered and I felt I wasn’t as present as I should have been for Buffer

I mentioned earlier that I traveled and relocated to new accommodation on the weekends, and I worked regular weeks for the full 3 month period. This went quite far in helping me to stay relatively productive during these travels.

At the same time, being in a new place means adjusting to many new things, even as simple as finding grocery shopping and food places. Everything takes a little longer than what you’ve become used to in a place you’ve had months or years to become familiar and comfortable with, and that can be a little frustrating if you don’t anticipate it. As a remote worker who enjoys the coffee shop environment to get things done, I also found that I could often get to a coffee shop which wasn’t an ideal setup or where the wifi was not quite fast enough, and so it could take a couple of attempts before I found a great one. That took away yet more time.

All in all, I do see the travels as somewhat of a failure with regards to my productivity and my contribution to Buffer. I’m not a student taking a year off to travel the world once before settling into work, this is instead something I’m working towards finding balance so it can be much more long-term. I don’t have a throwaway traveling job just to get by, I’m the CEO of a company with venture financing and I have a lot of personal ambition to take Buffer much further than where it is right now. Therefore, daily routine and overall focus is crucial to having fulfillment, and with so much travel in a short space of time, I couldn’t quite hit the flow that I feel I need.

Thankfully, I’ve been able to take these learnings and bounce to a new situation fairly quickly. Since choosing to adjust to ‘slow travel’ (more on that below) and stay in Hawaii for 4-5 months, I’ve hit possibly my best flow in years, both in terms of my work on Buffer and my fitness goals. I will always be someone who likes to challenge myself and push towards limits in order to learn. In some ways I see this compressed travel as similar to my experiment of working 7 days a week, which also resulted in some great learnings.

2. One or two weeks in a place is not long enough to build lasting friendships or understand the culture beyond the surface

I’ve learned as a result of experimenting with 1-2 week visits compared to 3-6 month slow travel, that whenever I have the choice from now on, I will always take the option to stay in a single place for a few months.

Beyond the productivity struggles that come with being somewhere only for 1-2 weeks, it is also not long enough to create true new friendships or relationships. It’s almost impossible to sustain this for a long period of time and also have any sense of community. It was a lot of fun, however as the travels went on I found myself craving that sense of community, being able to hang out with people that know me well. As an introvert, I find that I naturally get drained when I spend a lot of time with other people, and even more so when I’m constantly meeting new people.

In addition to the challenge of having friends and that sense of community, I believe that part of the joy of travel is to experience, understand, and be changed by different cultures. For myself, I’ve found that I really can’t start to understand the culture of a new place unless I “live” there, and I think it takes at least 3 months, maybe 6, for things to start clicking. I like to feel like I’ve truly lived somewhere, been a part of it, and hopefully even had some tiny impact on it for the better.

3. I was hit with loneliness and had several times I felt down

It seems almost crazy that I could be literally traversing 3 continents and visiting many places in the world that people dream of experiencing, and feel down. I felt almost guilty for feeling it at times, that it was a lack of gratitude.

For most of the 3 months I felt absolutely incredible, and had an awesome time. During my time traveling Asia during January, I didn’t feel lonely at all, because I was traveling with Brian. For the first half of February while I was in Sydney, I was with the rest of the Buffer team on our 5th team retreat and several people stayed in Sydney afterwards, so I felt great then too. It was the last few weeks in Sydney when I was there by myself, and then during my two weeks in Santa Monica that the loneliness hit me a few times.

It was a little scary to feel myself affected by this. Some days I lost several hours where I was just feeling down and procrastinating. I’ve had a couple of other experiences of feeling down for one reason or another in the past, but it had been over 5 years since I had any feelings like this, so it came as quite a shock.

I’ve realized that a key challenge as a digital nomad is loneliness, and in many ways my traveling lifestyle of the last few years has left me without many strong friendships or relationships. This being my first time solo traveling also brought this out even more for me, I think.

I’m generally quite a pragmatic person. I reflect a lot, which can sometimes make me dwell on something and feel even worse about it. However, this reflection often helps me pinpoint the cause and act on it. In this case, I instantly started making a big effort to meet new people, and I also chose to stay in Hawaii for several months in order to build some longer term friendships. The result is that I’ve been able to completely turn this feeling around within a month and a half, and haven’t felt down for weeks now. I also found that keeping up my exercise routine helped me immeasurably during the ‘downs’, by gaving me something to regularly get a win with (and the endorphins released). I never felt down when I was exercising, and it often triggered a high that lasted several hours afterwards.

3 key learnings I’m taking forward for future travel and being a digital nomad

To finish up, I want to share a few observations and learnings I want to take forward for myself:

1. Travel is incredible

“Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one’s lifetime.” - Mark Twain

I truly believe that the travel in the last few years has changed me for the better. If you have a chance to travel, I strongly urge you to take it. All the better if you can do it long-term in a sustainable way while working. Even short term travel is great, but if you can make it a lifestyle for even just a year or two, I think that’s when it becomes most powerful and fulfilling.

One of the best things about travel, and especially solo travel, which I’ve discovered in the last few months is how much you learn about yourself. I especially learned how to recharge and maintain energy and happiness, which came through experiencing both extremes of spending too much time with people as well as a few moments of real loneliness. I now feel much better equipped to strike that balance.

2. It’s important to know your purpose for travel, and your other chosen commitments

Whenever you choose to go traveling, you’re in a very unique position that applies only to you. We’re all different, and I think any sweeping advice is not wise.

I think it makes sense to think about what your own situation is. Are you young and focused purely on the travel, happy to do whatever job to just get by? Or do you already have your dream job and are striking the balance between the work you love and the destinations you want to see?

For me, I love working on Buffer, I couldn’t imagine a better job in the world. I also feel a big calling to see where we can take Buffer in the coming years. As a result, I plan to be very disciplined in the future about choosing my travel schedule. It’s important for me that I can spend the time I desire on Buffer, alongside seeing a new place.

3. For me, ‘slow travel’ is my preferred way to travel and be a digital nomad

Probably the most clear learning and conclusion for me of the 3 months of travel is that ‘slow travel’ is the perfect setup for me. By ‘slow travel’, I mean staying somewhere for at least 3 months, and generally 5-6 months or more. I’ve learned this for myself before in some casual ways, I even wrote about it a year ago. I feel like I’ve now truly pushed limits and experienced all options.

Most of these 3 months were short-term travel. Since then, I’ve been living in Hawaii for the last month and a half. I’ve found my flow and had some of my most productive weeks both on Buffer and with my exercise routine. I’ve met people who I’ve hung out with several times and hope some may become lifelong friends. This, for me, is what traveling is all about. This is my new plan.

What are your experiences of travel? Have you tried long-term travel, or do you want to? I’d love to hear from you in the comments!

Top photo credit: Andym5855. Rest are my own.