I’m Leaving My Company

6 Lessons About It and What’s Coming Next!

Filipe Castro Matos
L I F E
9 min readJun 15, 2016

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What a journey, I must say! If four years ago someone had told me that I would found my own company, I wouldn’t believe it. After all, before then I’d never thought about being an entrepreneur. In fact, I didn’t even know what that word meant, and I definitely wasn’t meant to be one. I’m not one of those cases of premature entrepreneurs — kids that sell all kinds of stuff to family and friends, or children that like to build things like Lego or games on computers. I’m from a family of doctors, teachers and officers, with no entrepreneurial background. You know — completely risk averse and meant to follow a normal life journey and a “traditional” career…

But one thing I’ve always explored since I was a kid is my creativity. Painting or writing were always among some of my favourite activities, to which you can now add photography, all kind of marketing stunts, and even home decoration. :) All of this made me conclude why I turned out to be an entrepreneur: I’m an entrepreneur because it is the only way I can explore my creativity to the fullest and be the real “me.”

The funny thing is that, not being completely aware of this, I chose a path that would finally lead to the foundation of my first startup. I’ve left my first job before finishing the contract, I’ve dropped out from the master’s, and I’ve worked with several startups and other projects and events. And only now, seeing the dots connecting, do I realize I was always pursuing the place where I could be the most creative. Because only in this way would I feel accomplished with my life. Only this would allow me to be my true “me.”

About WIME

Before founding WIME I was working on Startup Lisboa, the biggest startup incubator in Lisbon. And it was natural that after some time working there I decided to launch my own startup. You meet so many people doing the same there that such a decision is almost inevitable.

And so it was: at the end of 2014 I launched my startup, WIME (formerly O MEU COPO), with Rafa, Rodolfo and André (who later left the team). At first, it started as a simple online subscription service for wine, and nowadays it is positioning as one of the main wine retailers in Portugal and will soon do the same in other European countries. WIME allows you to discover the wine you actually like, and then buy more of it through one special pack, delivered to one of its stores or at home.

I don’t want to go into too much detail about this experience. If I wanted to, I could easily write a book with all our stories, dramas and successes. In hindsight, though, there were some main lessons that made founding a company the most unbelievable and striking episode in my life and, at the same time, the lessons that made me take one of my hardest decisions ever. Here they are:

1. Learn quickly whether you work well with the rest of the team and define from Day 1 your positions and tasks. And, for God’s sake, don’t try to build a company alone! For six months I was the only full-time person in the company and it’s really hard to manage all the tasks, but mainly all your emotions, alone. After all, as I’ve read countless times from other founders, the team is a great part of the recipe for success.

2. Product vs. go-to-market strategy. Don’t lose too much time developing your product without having even made some tests in the market, but also don’t try to reach every target and invest in every channel without validating the product often enough and not making the needed changes regularly. Usually what happens is either developing a product that doesn’t sell later, or developing so many sales channels that you always manage to find someone to sell your product to but don’t sell enough to scale your business because your product is not serving a big market. Today I see that we were good in the first point, launching a product quickly, but too many times we lost the focus on the go-to-market strategy and didn’t dedicate enough time to improve the product along the way.

3. Online vs. offline. I’m definitely a digital guy. I’ve had a computer at home forever. I’m always digitally connected and I spend all my life surrounded by it — working tools, social networks, online shopping, leisure, etc. But I’m also a true believer that there are amazing business opportunities in the “physical world.” After all, our world is made of amazing products that we’ll never stop to eat, drink, feel, taste… But where there are big opportunities, there are also some of the biggest challenges, as it’s really hard to connect these two worlds and create something simple and valuable for all stakeholders. If you want to work in something like this, you must be aware of the difficulties that will come. In our case, we started raising awareness and acquiring customers only online (our first mistake), and we changed somewhere in the middle to do this essentially offline (also a mistake). A multi-channel strategy is crucial, but you need to guarantee that you have both backgrounds in your team and that the same investment and effort is made in both — at least until you’re sure what works better.

4. Your personal life is severely affected. Building a company from scratch is incredibly hard and it seriously affects all the other aspects of your life. You lose money every day, you stop exercising, you eat unhealthy food, you have no routine, you have no time for your girlfriend or boyfriend, and you don’t talk for months with some of your friends… It hurts so much, and there is no previous preparation for that. Have this in mind: Doing a startup is a long and painful journey, with some rewards but also many sacrifices.

5. Running your own business is tough and you have surprises everyday. I thought I knew what a founder needs to know to be successful, but now I realize it’s way harder than I could have ever imagined. But I also realize that you’re not supposed to know everything, especially if it’s your first startup. I would say that no experience gives you enough experience to know that until the day you really risk your career, time and money. Only on the day you’re in the middle of the ocean, full of sharks and with nothing, will you find out how to make a knife from water like MacGyver and kill all the beasts along the way.

6. Everybody is different and there are several paths to reach the same point. But this point — call it the vision of the company — must be the same between all the team members, mainly between the founders and investors. If the opinions about the vision are different, somewhere along the way you’ll start disagreeing on many things and eventually work without any passion, which is exactly what happened to me in the last months. And believe it, you’ll need that passion — as Steve Jobs says in one of my favourite interviews with him:

Leaving WIME was not an easy decision. Too many emotions are involved, but sometimes you need to take some serious and courageous decisions, for the company’s wellbeing and your own. I’m proud: I’ve contributed to building a company from scratch to a company with a team of around ten people, two open stores, two rounds of investment and hundreds of customers from the north to the south of Portugal. I’ve put all my energy, skills and creativity into this company during the past year and half. I’ve learned so many things that it felt like an MBA on the ground. This company was my baby during this whole time and I’m fortunate to have worked with some of the most extraordinary people I’ve ever worked with, people that were most of the time like my family. But now it’s time to follow a different direction and let the baby grow. WIME is not over and I’m sure its team will do a great job of growing it.

And now?

The last couple of months were very introspective for me. I’ve dedicated more time to thinking instead of executing. Because sometimes you need to stop to know if you’re going the right way.

I’ve realized that I need to focus on other areas in my life and further explore my natural skills, without losing my entrepreneurial side, in order to be completely fulfilled and happy.

I didn’t want to immediately start something new like a company because I believe an experience like what I had needs to be dissected enough so I can take all the learnings and lessons for my next venture, one day.

And so, my decision to join someone’s company, a company still in the startup phase but already with some good results, fundraising to grow and all the conditions to explore all my creativity, was easy to take. Today I officially announce that I’m joining Prodsmart’s team to help them grow the marketing of the company! Thank you, Gonçalo and Samuel, for your strong desire to work with me. It made a difference in my decision. :)

But I also want to dedicate some of my time to other stuff that I’m really missing: I definitely want to write more often, read a huge list of books already bookmarked, travel to new places and meet new people, spend more time with my family and old friends, exercise and cook more to pursue a healthier way of life, spend more time with my lady dog, and a few other things.

Today I’m well, calm and, above all, happy. And that is all that matters. Great and exciting times are coming!

Cheers!

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Filipe Castro Matos
L I F E

Writing about entrepreneurship, startups, marketing and one or two things about life.