A guide to friends and family of a startup founder

Over the course of the last two years (since I started BinaryEdge) I’ve both discussed with other founders a set of topics, and a regular one that is brought up is “the opinions and sentences said by our friends and family”.

My objective with this post is to once and for all have a reference I can point my own friends and family to when they have some questions about how it is “being a founder of a startup” and “my own boss”.

The “reality” part won’t be the same for all of us founders, some have had it better than me, some have had it worse. My answers here are based on my own experiences and discussions with other founders.

I will breakdown each subtopic in 3 parts, the “Assumption/Sentence” (what people think), the “reality” (what actually goes on) and the “real benefit” (of being a founder in this situation).

Assumption/Sentence: “It’s so great that you’re your own boss, you have all the free time you need and no one telling you what to do!”

Reality: Let’s start by breaking down this one into two parts:

• Free time — Yes, it is true that I have more “freedom” with my time. This does not mean necessarily that I have more free time. When I used to work my “regular” jobs, I used to go in at 9 then I would take 1 hour for lunch where it would be relaxing and I’d probably go somewhere to eat with my colleagues and then work until 6. Then I would arrive home, play some games and watch series until 12 and off to bed.

These days, I wake up at 10AM (yes later than I did for my normal job), I jump into the shower, sometimes with my phone (yes it is water resistant) and immediately start checking which emails I have and if I got some replies from the day before. Then I have my breakfast (while on the phone), then I sit at my desk and will only get up at 2PM, to go to the kitchen eat up lunch and sit back down, continuously either replying to emails, checking in with the team, or looking at the features and testing new things that have been deployed. This usually goes all the way up until 9/10PM. Also, in a startup and as a founder, you work weekends and you don’t get paid extra or at a special rate.

Sometimes my schedule isn’t really mine anymore as I have to make my schedule available around the prospective clients that we might have for calls/meetings.

Also, while on the free time topic, in the last 2 years of being a founder, I count that I’ve had 2 proper weeks of holidays (and from what I hear from other founders I’m lucky in this department).

• No one telling you what to do — This is a fun one, as it depends on a lot of circumstances, ranging from what phase your startup is in, from who your investors are, to deals you make.

If you’re just starting and it is just you and maybe a co-founder, this is true, you make the decisions and no one will tell you what to do. However, the moment you take an investment in, then its no longer “just you” and you do need to answer to someone. This someone is called a board of directors.

Depending on the type of deal you make, you might need to report to them every X times per week/month, or for example you can’t,on your own, make a decision over some amount of money. At this phase you’re no longer “the only boss where you can do whatever you want” and you do need to justify and sometimes even ask for approval for your decisions.

This doesn’t need to be a bad thing however, the board is often there to help you progress the company and to help it grow.

Real Benefit: In this specific situation, the real benefit of being a startup founder is if you have something you like to do that is conditioned by something. What does this mean?

In my case, I like to photograph (for some people it’s going snowboarding, surfing or just reading a book under the sun). Some very specific photos I can only catch at a certain time of day or under specific weather conditions. In case those happen and I don’t have a call or meeting, I can just grab my camera and go. I don’t have to ask anybody, or if I was at a corporate job stay at my desk while looking outside at everyone in the sun.

We had really grey weather for a really long time, at the first ray of sunshine I knew I needed to go and take a photo of Spring starting here in Zürich.

Assumption/Sentence: “You guys always have fun as I see photos on facebook and twitter, also OMG you guys are famous, I keep seeing websites talk about you and saw you on the news yesterday” (I like to call this assumption the “only seeing the bright side”)

Reality: Part of it is true. I have a lot of fun when I am with my team.

before our presentation at Bsides Lisbon in 2016

They are like a second family to me.

They work super super super hard to work on what was initially my dream and that I now hope is also theirs, which is build a great product, and see internet becoming a more secure place (we are a cybersecurity company).

And of course, when I am with them, I try to make sure they have fun and enjoy their time.

And yes, sometimes we do show up on the news. But it’s not out of magic or because we paid for it or out of cheer luck. It’s because we worked our asses off, putting in the extra time and extra effort to try and do something that makes us stand out from the rest.

To give you two examples:

A couple of months ago, we got invited to participate in a study done by O’reilly on Development workflows for data scientists. Comparing the other companies that were there (Github, AirBnB, ScotiaBank), we are probably smaller as a company than any individual team inside these companies. But it took a lot of extra hours, looking at the questions, understand how to answer them and, even before we got to this point, writing the blogpost that lead to us getting found to participate in this study was a lot of hard work as well.

(It’s important to take into account when you are a small company, resources are scarce and you really need to manage your time well.)

The second example was our Internet Security Exposure report.

Getting this out took for 3 months a lot of 18+ hours of work per day.

From getting the data, analysing it, creating the data visualizations, draft reviews etc… and all of this gets done while still building a great product and maintaining our customers happy.

These are two examples of our work that got re-tweeted, shared and showed up on the news. But the point here is that, it wasn’t easy, and when you see just the blogpost or news article where you showed your need to understand the road that got us there, not just the spotlight.

While on this topic when we published the ISE, we also did our Bsides Lisbon and Pixel Camps talk. Again here we tried our best to stand out, we could have just gone on stage and do our presentation but we decided we wanted to go the extra mile and built a “mini comic book” that showed how we created our data science team.

Do we do this because we just feel like we have too much free time? No, we do this because the startup world is cutthroat, as a startup you are not an established brand and have a job where you can just say “I work for X big brand and I can just show up do my job everyday that my payday is guaranteed”, you have to innovate, you have to stand out.

People see the posts on facebook and twitter, they see the bright side. If you sit down with a founder and ask them about the bad nights you will hear the real side of it:

• From the nights you spend awake worrying how you’re going to pay salaries
• The nights you cry your eyes out because a deal fell through and you lost a possible huge customer, or because the pressure just becomes too much and in the next day, you need to clean up your act and go at it again with a smile on your face. (One thing Tim Ferris says on his Tools of Titans book fits well here. “Manic-Depressive symptoms are just part of entrepreneurship” you just need to learn how to deal with them.)
• The stress where you find yourself waking up in the middle of the night because of an email you’re waiting for.
• The pressure you feel when everyone looks at you for a critical decision that can make or break the company (this is actually an important point and if you’re thinking of starting a company you need to understand from the beginning — the wins are shared as a team, the fails will always at the end be put on top of you as a founder. This is something you need to learn to deal with.)
• Dealing with drama and egos — as a founder this is one of your biggest challenges.
• Always having to keep a smile to not put stress on friends and family around you because the moments you have with them are so little that you need to make sure you enjoy them as much as possible.

Real Benefit: As a founder there are multiple benefits here.

• Ability to see your dream come true.
• Working with people you handpicked and choose because you saw “something” on them.
• Learning how to deal with your emotions and putting your own ego on check ( I personally see this as a benefit).
• Watching your team grow, in skill, watch their CVs grow with publications like the O’reilly
• Watching your company grow

Assumption/Sentence: “ Oh you’re a startup you must be swimming in VC money and throwing lots of parties.”

Reality: Again it depends. Don’t assume every startup already went through rounds of investment or even that those rounds allowed for “party money”.

For me, personally, I could easily be earning 3x what I currently do if I had stayed at my corporate job or took some of the offers I receive sometimes.

In our case, we took a seed round to take our product from MVP to a usable product and to give us a buffer until we acquired our first customer, and after that what we got paid would have to pay our salaries.

We decided to keep pushing without raising another round.

(This is a personal choice, but I’m still a big believer in validating your product with paying customers. I see a lot of startups raising money without having customers or an actual product and they keep raising and raising without actually ever having a plan on how to make money.)

Real benefit: The less people you bring in as investors the less people telling you what to do. And yes if / when you get acquired or go into an IPO you can make a lot more money. (Same for the team that built the company with you, a good example of this was the whatsapp team).

I think these three are a good start. At this point you might be thinking “why did you ever bother starting your own company then?”

• Creativity freedom — I saw a problem and I knew I could fix it. I noticed there were some people doing it but they were either doing it wrong or just not as right as it could be.
• Reward — Both monetary and psychological — Anyone that follows the startup world knows that if you’ve got a good, validated idea you can get good monetary reward at the end, and honestly I have a hard time believing people when they say “they don’t do it for the money”. In terms of the psychological part, I get a huge boost to my morale and get really hyper when I see the cool stuff my team does, and watching them all grow its absolutely fantastic ( I love taking a step back and comparing some of the decisions they make now, when compared to one year ago and watching their evolution). Also seeing say “my favourite talk was the one from BinaryEdge on data science and internet scanning.” really makes me happy, warm and fuzzy on the inside.
• Challenge- One big problem I had at previous jobs is that the first few months I would have some really interesting problems, but then it was “more of the same”. Being a founder, you have such as different set of challenges and problems to deal with that, if like me you thrive under pressure and like big challenges you will absolutely love being a founder. From understanding who are the right partners for you, to discussing with them the next deal, finding how your solution fits a client, discussing different technology with your team and coming to the solution at the end, understanding how NDAs and contracts work, discussing with the accountant the different types of bills and what you need to pay and when.

Its a huge ecosystem of questions and challenges that makes it really fun being a founder, of course on top of all this don’t forget you need to:

• keep up with your team and help them
• keep up with your industry in a deep level to understand how it is growing and if your product is walking along with it
• keep up with industries around yours to see if they can help your product grow (in my case it’s cybersecurity, machine learning, data science and insurtech), and still have a life.

One sentence that I read that I feel is interesting here is by Adam Gazzaley:

I would say to have no fear, I mean you’ve got one chance here to do amazing things, and being afraid of being wrong or making a mistake or fumbling is just not how you do something of impact

I hope this post showed you some of the non glamorous life of a being a founder.