Work/Life balance

I believe the overall idea of having a balance between work and life is sane and makes sense. In the general sense of what it means, I advocate for it and pursue it for my own life actively, but I also think people want to take it a bit too far quite too often.

In the context of creating your own startup, if you think working hard is optional and that you can keep your normal office hours strictly between 9 to 5, then you’ll set yourself for a big surprise. This is definitely possible to achieve in the long run but pretending it is possible when you are just starting up is just fooling yourself.

Let me try to make you view it from my perspective and let’s agree on the following:

  1. Time is precious. You only have a finite amount of it and you want to use it wisely.
  2. You are building a tech startup that is more likely to fail than not.

If you agree to the statements above then you may agree with my points below.

I would work the hardest I can for the longest I can because I want to know if my startup will succeed or not. I would like to know it sooner rather than later to minimize not only the negative financial impact on my life but most importantly, the negative time impact of potentially be working on the wrong things.

I don’t know how you can get there if you only work 9 to 5, no weekends, and taking your usual vacations in the middle. Maybe there is a way and I just have not found it.

I know sustaining this intense rhythm for too long will have negative consequences and that’s why it is important to know yourself fully before doing anything. You have to know your limits, when to push harder, when to rest, and sometimes when to quit.

I’m not a competitor in the contest of “who works the hardest” either and to be honest, I wish I could work less and still get to achieve the goals I set for myself in life.

I tried working fewer hours and it didn’t work out just like the time when I tried to sleep less so that I could have more hours to work. In the end, I had 19 hours a day of a cloudy mind that couldn’t think straight and that was significantly less creative than my well-rested mind.

There are public figures on the Internet that are very vocal about working hard and smart, like Sam Altman, and those who say that working long hours is wrong at any stage, like DHH and Jason Fried. I think all of them make very good points.

Given my circumstances in life, where I live, where I come from, my socioeconomic background, and where I want to be in the future, for me at least, working the hardest I can while I can has not been optional.

I know this opinion won’t sit well with everybody, and after all, people’s ultimate goal is happiness and there are several paths that lead to it. At the end of the day, you have to follow the one that you feel is right for you and a random guy like me on the Internet should not have a saying in there ;).

Doing the hard things

It feels counterintuitive and probably against nature to choose to do the harder things when you have the option to go for the easier ones when the perceived reward feels similar. We as humans have this natural inclination towards the path of least resistance and it makes evolutionary sense that we are programmed to behave this way but I doubt that in business is the right thing to do.

Let’s say we have a business idea and we want to create a product. The next steps to analyze the feasibility of the said product usually are the designing of a business plan, monetization strategies, marketing, etc. but what oftentimes is never analyzed is the entry barrier or how easy would it be for the competition to come to steal your customers if they decide your market is sexy enough.

If you find yourself seeing that a guy is having huge success selling piña-coladas on a beach and everyone is buying from him, you can almost effortlessly go do the same thing and compete for his customers. The market for piña-coladas is big but the product is so easy to replicate you may be able to attain success fast but it is equally likely that the success will be short-living. Easy come easy go.

The software industry is no different.

Maybe you noticed that every business needs to be able to send bulk emails to their customers and decided to enter the market for emailing services since it looks easy to write a few scripts and an HTML templating system to go on and compete with Mailchimp, no?

It’s possible that you will find an audience willing to pay you for your service since the market is so big but it’s going to be hard to differentiate yourself from others and customer-churn will be an issue from day one. That low hanging fruit you saw and wanted to grab was also seen by a thousand other people.

With Toky, we went through a similar situation. Almost all businesses need to offer a voice communication channel to their customers and we exist because of that. A thousand other people saw the same thing and probably wanted to grab that low hanging fruit too until they realized that doing telephony right is very very hard.

There are quite a lot of other things that may be important to discuss regarding this topic, as the potential for your business to attract talent, something that can only happen if people find what you do meaningful enough to come to work with you. Sam Altman wrote a very compelling essay on this topic that explains this point better than I can.

All in all, choosing to go for the easiest-to-create product may not always be the right choice. You are not more likely to fail if you go through with that other project that is harder, in fact, it will probably increase your chances of making it all things considered.

Definition of success

Throughout the years I learned that people will only listen to what you have to say if your reputation—or the perception they have of said reputation—matches what they consider to be within the scope of their definition of success.

I believe there are some things that are universally accepted as being part of achieving success but many things that people think define a successful person are highly dependent on external factors like beliefs, geography, age, and access to opportunities.

In my own experience, my definition of success matched that of the “American Dream” as crazy as that may sound. I’m not even from the United States, I didn’t really speak English until the 2010s, and the first time I visited the country was in 2014.

It was hard for me to realize I needed to find my own definition of success if I ever wanted to get out of that constant feeling of being an underachiever.

I noticed that I was often comparing myself to people in the startup scene that were clearly more achieving than I was (or I will ever be) and feeling terrible in consequence because I knew I couldn’t possibly get to their level even if I worked 20-hours workdays.

I don’t remember the day it happened when I turned that sensation of feeling less into inspiration for wanting to achieve more. I stopped comparing myself to others and I started competing against myself only.

That didn’t mean I didn’t have role models anymore or that I didn’t check out on other founders from time to time. What it means is that I have a direction of where I want to be in my life and sometimes that direction coincides with where other people are, so I follow them to try to learn from them, but I no longer feel disappointed that I’m so far behind and I am fine with the thought of me potentially never getting there in my lifetime.

I learned that success means different things for many people. Mine keeps morphing but I noticed that a few things are always around: family, health, happiness, and money.

Financial freedom, a.k.a. having money, is one of those things that everyone pursues and it’s often used as a synonym of being successful.

I want financial freedom and I always wanted it—I don’t think there’s anything inherently wrong with it—but it quickly becomes worthless if you have to sacrifice your health, family or happiness in order to get it. See the point?

I believe being well–off financially is a byproduct of doing other things well in life, maybe by starting a business you are passionate about, maybe by doing a job really well because you love it. Maybe our focus should be on finding that passion instead of blindly following money while we wreck other things in our life that are obviously more important.

There’s a saying that really touched me that was brought to me thanks to @naval:

A healthy man wants 10,000 things, a sick man only wants one thing.

Confucius?

This saying is 2,500 years old. I don’t think there’s a better reminder than this to sit down and reconsider your priorities regularly.

My rule of thumb for hiring

At the time of this writing, we are a team of 24 people working at Toky. We are a small team and we try to keep it that way. We optimize for happiness and impact and you don’t need a huge team for that.

The playbook we created is simple and obvious, and it basically consists of evaluating three aspects of the candidate: good person, good communication skills, and intelligence.

Good person

No one likes working with douchebags, no matter how brilliant they are.

Being a good person means for me that they are not selfish, that they can be empathetic towards others, that they won’t selfishly prioritize themselves above everyone else to get where they want to be.

What has worked for me is asking questions that can lead you to see things that may not be compatible with your culture. Open-ended questions like “what makes you happy” are good for this purpose as they can lead the way into more profound questions that will let you understand better about their personality and values.

This one is probably the hardest thing to evaluate because it can be easily faked in an interview.

Good communication skills

Along the way you are always going to encounter problems of all kinds, and it is fundamental that you can communicate yourselves out of them when it happens.

A good sign a person is good at communicating is when they ask hard questions during the interview, or when they can openly talk about failures they have experienced in the past and how they got themselves out of them.

Seeing traits of introversion is not necessarily a bad sign either—people can be reserved and still be able to communicate well with their peers—but being too reserved can be an issue if everyone else in your team is an extrovert.

A person that can articulate in simple words what’s on their mind, that can tell me I’m wrong when I’m wrong, that can openly accept feedback and give feedback back in a constructive way, is what I look for every time.

Intelligence

This one is not about raw IQ measurements or how well they did on their last exam, in fact, I don’t even believe good grades are a sign of intelligence, but that’s a conversation for another time.

Building a product like Toky is not only very hard on the technical side, but the environment is also constantly changing that we need to adapt ourselves and the product regularly if we want to continue on business.

Dealing with change, with shifting priorities, with needing to acquire new technical skills when it is required, is something not a lot of people are comfortable with.

The kind of intelligence I’m talking about here doesn’t have a specific name. It’s probably an intersection between the resourcefulness mathematical intelligence gives you and the ability to successfully adapt to change that emotional intelligence can bring.

What’s clear is that our customers and industry will continue mutating and the only option we have is to adapt or perish. Everyone at Toky knows this and we welcome change every time it comes knocking at our door.

This set of rules brought to our team the most amazing people that I feel very fortunate to be working with.

It’s definitely not a comprehensive list but hopefully good enough to give you an idea of the kind of values we cherish that made us the kind of company we are today.

Late 2018, a smaller team but just as happy as we are today doing what we love.

When you are not in Silicon Valley

Situational awareness is a concept I learned from the aviation industry that pretty much describes everything I want to say here.

I’m a tech-startup founder, an admirer of what Silicon Valley (SV) embodies, and a long time follower of the personalities that came out of that place. I don’t live there, I don’t have any contacts there, I’ve been there only two times before (both paid by YCombinator) and I don’t have any way of moving there even if I wanted to.

For the few months leading to the founding of Toky, and until late 2016 more or less, I was obsessed with the SV way of doing things. I was consuming startup advice originating there, reading VC Twitter like crazy, checking TechCrunch daily, and following founders with huge investment rounds running their companies from San Francisco.

All of that knowledge shared for free is fantastic but if you don’t realize you have to adjust it to your reality it will end up killing your startup sooner rather than later.

In Silicon Valley, but not really there

For example, access to funding in Latin America—where Toky was born—is significantly harder than it is in SV or in some countries in Europe. I remember that getting funding for our seed stage in Mexico was so hard because we are a SaaS company and most of the investors back then didn’t have experience with it or with our industry in general. They were funding B2C or marketplace deals only.

Things that people take for granted in SV were an ordeal for us. Basic things like getting a credit-card processor to work took weeks, Stripe didn’t even exist here when we started in 2014, and the one we used instead ended up not working reliably for payments outside of Mexico so we had to take care of that too.

Purchasing a bunch of subscription software to “streamline processes”, like project management tools, monitoring tools, hosted services for open-source free software, all come from the idea that you should optimize your time for running your business in the most efficient way but what you need to account for is that paying $100/month for a project management tool that could have been just a Google Sheet, or paying $50/month for a hosted WordPress blog when you can do it for $5/month installing it yourself, quickly add up to what is lunch money in SV but could be a weekly salary for people in Mexico or other countries.

When you have millions of dollars in funding you are expected to optimize for maximum growth at the expense of profitability, but when your funding is slim, you have to focus on what is most important for keeping your startup alive, maybe profitability or maybe something else. As Paul Graham puts it, you need to be default-alive [1].

Once you have reached a state where you no longer worry—too much—about running out of money, then making optimizations make more sense. At this stage, paying for project management tools becomes an investment and not an expense, and having to worry about updating your WordPress site can be delegated to a hosted service provider.

Read everything you can about how to do what you want to do but have your own playbook that is in accordance with your reality, otherwise, you will just end up frustrated and most likely, with a dying business.

[1] If you want to start with general knowledge about how to create a tech-startup, check out Startup School by YCombinator. It’s offered free of charge and with the best intentions.

Deciding when it’s time to make the jump

When I tell my story of entrepreneurship to friends they always have the impression that I’m braver than they are for having the guts to quit a perfectly fine job to embark myself in the journey of starting a business. The reality however, is quite different and much less romantic than what people usually think.

I was not brave or smart in any way. I didn’t really know what I was doing. I had a lot of energy and I was very lucky. You can safely say I was a complete ignorant of the risks involved in starting a business.

I think a huge amount of young founders don’t really know what they are doing at all when they start. What we have in common is usually that we have very little to lose and substantial amounts of energy focused into making a single goal become a reality.

Taking my ignorance aside for a moment, I did realize that I was probably never going to be in a more comfortable position to take the risk of creating Toky so here’s a list of the things that worked out for me to decide it was the right time:

I had money saved up

Not a lot, but around 4 months worth of living expenses. No debts.

Good health

I felt very strong physically and mentally. I was eating good and exercising a lot. My mind was also in a good place.

I changed my environment

I had just moved to Mexico. I didn’t have friends, family around and I didn’t feel like being home. Everything felt like new and I wasn’t attached to anything.

The change inspired me

Moving from Asunción to Mexico City was a shock in every way. From living all my life in small towns and cities to suddenly being in a gigantic city surrounded by millions of people made me see the world differently. It made me feel that I was maybe capable of doing things I thought I couldn’t.

I was focused on a single objective

My wife received a big promotion and with that came a salary increase for her. I felt that I could fail with Toky without being afraid of becoming homeless as consequence. This mental state was fundamental at that time because it subconsciously gave me permission to risk everything I had and freed my mind to solely focus on Toky.

I felt supported

I built an MVP of Toky and with that I went to pitch it to Wayra and to my surprise, they decided to invest. This is probably the single biggest signal I received it was time to make the jump. That’s exactly what I did in September 2014.

As you can see, I was not brave at all and I was really lucky to be in the position I was when I decided to start Toky. I can only take one merit out of this entire situation and that is that I recognized the opportunity and I didn’t let it escape.

Every person and situation is different but maybe after reading my experience you can relate to it in some ways. Maybe you are hesitant because you are afraid or feel unprepared and for what it’s worth, I don’t think you will ever feel prepared and that’s okay.

Focus or fail

It’s so easy to fall into the illusion of work where you can spend hours doing something that feels like work but that in reality is not contributing anything to the health of your startup.

I fell into this trap many times during the initial 18 months of Toky by attending to conferences, doing interviews for media outlets in Paraguay and in Mexico, actively seeking attention for my “successes” with Toky and generally enjoying the praise I was receiving from the public for being “brave and smart” for having created a tech startup.

I was enjoying myself feeling important. It’s an addictive feeling that’s so hard to let go of and that’s so toxic at the same time.

I felt like a winner back then and ironically, I was absolutely certain that I was great and that Toky was going to turn out to be a huge success. It’s ironic because today, after almost 6 years and having survived all sorts of shit-shows, I still need to remind myself every day that I’m more experienced now so that I can gain the confidence I need to execute.

I wasted many months working on the wrong things and focusing on unimportant stuff. My fellow batch founders in Wayra were doing exactly the same thing and no one was telling us we should be focusing on our businesses instead. Many startups on my batch died, and I don’t know enough to make a fair judgment here, but I’m sure the lack of focus was one of the main reasons for this outcome.

In 2015, and after realizing we had an expiration date because we were quickly running out of money, the shock of learning this fact opened our eyes and we were forced to work on the right things or admit we were going to fail.

In a memory that I can recall vividly, I remember Oscar and I walking around Parque México in Mexico City discussing that we needed to change focus and start charging money for our product or that otherwise our days were numbered. After a few walk-arounds that park, we turned Toky from a B2C business into B2B.

A similar view of the one we had that day during that walk in Parque México

After that, our attention-seeking addiction slowly started to vanish and we slowly also started disappearing from the visible world. We locked ourselves down and started building the product that we have today.

In an unsurprising turn of events, we saw that the world didn’t actually care at all about us. When we chose to not show ourselves any more people hardly noticed. It was a new reality that was hard swallow but that we learned to move on from eventually.

Focus doesn’t receive enough attention and is a piece of advice that is easy to accept but very hard to follow. I’ve been there myself and I get it, but this time you need to not just listen, you need to act.

Determine what’s important for the success of your startup, determine the order of importance of each thing, and focus on one (or a small few) thing(s) at a time.

Have everything written down in paper

At the beginning of a new project everyone is super energized, hopeful and ready to bleed for the end goal. Hopefully those days will never end but if they do, you have to be prepared and protected.

You have to do an explicitly targeted work to keep the relationship with your business partners healthy. You have to truly care about their wellbeing and you have to mean this. It has to come from the inside and you have to make time to talk about it regularly.

The above advice will keep you from ever having to recur to the legal papers I’m talking about here. The order is important. Invest in your relationships first so that you don’t have to fall back to the legal documents ever.

Having said that, every aspect of your business deal must have a paper counterpart. How much everyone owns, vesting periods, what happens if someone decides to leave, how to decide if someone is no longer a fit and what to do about it, how is decision power divided, how to fire a cofounder, how to handle dividends, how to decide if you want to sell the company, etc.

This post is not about creating a comprehensive list of the things you need to consider for the contract between you and your partner. It’s more about bringing to your attention that you need to protect yourself and everyone involved by having all rules of the game very clear from the very start.

Remember that creating a startup is already stressful. You don’t need yet another worry to your anxiety bucket if for any reason something unexpected, like a cofounder wanting to leave, happens.

Who to take startup advice from

Everyone has an opinion on everything and a reason to think they are right and that you are wrong. Ironically enough, this post can very well be one of them, but I’ll let you make that decision yourself ;-).

When I was going through Wayra, the startup accelerator Toky was part of in 2014, the advisors hired to help us were coming mostly from the corporate world. They all had relevant roles and academic titles proving on paper that they made the time to learn what they came to advise, but the disconnection between how they did things at their jobs and how things can be done in a tiny startup that is more dead than alive, didn’t seem to be evident to most of them.

I remember being forced to make a huge spreadsheet with user acquisition projections, how much we were going to make in sales, and how things would look like in 5 years. It made complete sense to them that we should be spending time on multi-year projections instead of on building a product and actually selling it.

On another occasion, I remember we were having meetings and attending law firms to meet Intellectual-Property lawyers who were helping us patent everything we built. The only problem was that we didn’t really have anything worthy of a patent at that time but they were following a timeline that I’m sure made sense on paper but in reality, was completely useless and a waste of time.

Why weren’t we meeting product people and working all the time on user acquisition? Why no one was noticing that we didn’t have an infinite runway and that we should be focusing on improving our metrics to look more appealing to potential investors so that we can survive another year? Why was all advice assuming we had a huge budget of millions to pay people to come to visit us and buy our product?

I’m sure everyone there had good intentions and really wanted to help. I met great people there and I know one of the reasons we still exist as a business is because they gave us the seed money we needed to take off. The last thing I want is to sound ungrateful.

My point is that you should listen to every piece of advice and opinion you can, but giving your maximum attention to the ones coming from people who had been in your shoes before or that are in a place where you would like to be in the future.

Like making charity with other people’s money, throwing startup tips from the comfort of a safe corporate salary, is just too easy to not do it. Always take them with a grain of salt.

Picking your startup idea

There’s plenty of advice out there about how to do it, but based on my own experience, it all comes down to two fundamental things: how much you love it and how are you going to make money with it.

The idea—the product you are going to build—is going to stay with you for years to come so you better feel passionate about it and be ready to think about it every day for years.

In my case, it felt natural to start a telecommunications startup because that’s what I have been doing for the past 6 years at that point. I liked it, I felt passionate about it and learning new things on the subject became like a hobby of mine.

Obsession is a strong adjective but it pretty much describes my feelings towards this industry and how much I like it.

Toky’s first office in 2014 was the kitchen in my apartment. We were enjoying ourselves just as much as we do it today—it never felt like work.

My point is that your likelihood of succeeding with your startup increases significantly if you are building on top of something you truly love, being in an industry you find interesting and when working on your product doesn’t feel like a burden. You have to love doing it.

Then, there’s the ability of your idea to generate money. You must think about this early on even if you are living with your parents today or have no responsibilities with other people like significant others for example.

Doing it for the money as motivator is debatable and I’m not saying that. What I am saying is that the discussion about how you are going to turn your time and expertise invested in your idea into tangible wealth must be addressed since the very beginning with yourself and with everyone else involved in the risks you are going to take.

The thrill of starting something new and those days of working tirelessly with an excitement expression on your face are going to, undoubtedly, dry out some day and when that day comes you will want to have the assurance you can pay your rent, health and food while you rest and recharge energies.

In the perfect world, your skills, your idea and the industry where your product is going to exist all intersect at a point where making a sustainable stream of income is possible.

When we started Toky we were completely ignorant of how to run a business and we barely talked about how the product was going to make money. It seems like I didn’t follow my own advice and you are absolutely right to think that.

What saved us was that we picked the right idea where our combined skills made it possible to actually build something useful inside an industry that was growing at an accelerating pace. We basically jumped on top of a wave that carried us with it and that ended up compensating for the many things we disregarded during our early days as a company.

It wasn’t luck how we chose the idea, product and the industry—that we did well because it was an informed decision—but it was definitely luck how the industry was growing so fast that admitted so many products to coexist without saturating the customers and allowing us to make money in the process.

So don’t be us and don’t rely on luck so much. Have the idea, product, industry and money conversation early and as often as necessary.