Lessons from a startup, two kids and a serial entrepreneur

João Nuno Nogueira
Ascent Publication
Published in
10 min readMar 23, 2016

For the first time in my life I was a speaker and coach @ineo Start, an acceleration program for early stage startups/projects in Coimbra, Portugal.

The interesting part of being a coach, that works closely with very intelligent people, (much more intelligent and talented than me) is that you advise teams as much as they advise and teach you. When I got through that door for the first time, I never thought I would learn so much during the 5 weeks of the program.

This is me speaking about customer development (using Calvin and Hobbes as an example) @ ineo Start 2015

Most people don’t understand this. They think that coaching and mentoring is a one way process, like a mentor-centric-approach where you speak, you teach and you go on with your life. That’s not coaching or mentoring, that’s a monologue - and a self-centered-selfish-approach if you want me to be honest. This approach is just wrong, but widely used nowadays even in ineo Start. But that’s another blog post :)

Acceleration programs are about sharing and evolving with teams! That’s what brings true value to startups!

During the 5 week program I was able to work with several companies, but one in particular was AWESOME. This company was Book in Loop (BiL). It is a seamless door-to-door platform that allows families to save up to 80% in their children’s textbooks.

Book in Loop Logo! Yey!

I don’t have any idea if they’re going to be famous, or if their business model is the right approach, what was really impressive about them was the work culture of the founders. We are talking about a serial entrepreneur and two law students, a 18 year old and a 21 year old… And these 3 guys taught me a lot of things during these 5 weeks! I will try to synthesize all that I’ve learned from working with them, focusing in what can be applied to every early stage startup. So here we go!

1- Everyday you need to have news to tell!

When you are building a startup you live in dog years. One month in your startup is like one year in the real world. Things move really, really fast, and you need to follow this pace! So everyday entrepreneurs must have objectives, and have something new to say about their business. The culture of “take it slow” is not for startups, if you want that you can go to public administration or a big corporate job.

BiL’s pace is quite impressive. Everyday these guys have news forme - a new partner to help them in the process they are implementing, a new feature in their website, a new client being addressed, a new opportunity that appears - basically new data and information everyday! When I say everyday I mean E-V-E-R-Y-D-A-Y! Every single day these guys have news for me about their project. It is amazing to see the fast pace they are moving (just the three of them!), it is exhausting and amazing to work with people like them! They are so fast reacting to everything around them and to every source of data, that it is possible to see their evolution daily! With this agility and fast pace they can establish daily/weekly objectives (some of them really hardcore) and move fast to achieve those goals or change the plan if necessary! And that introduces the second thing I’ve learned:

2- Always have a plan

Most startups work in chaos mode. If you ask them for a plan they just shout a few incoherent milestones that they have. Things get even nastier when you ask them why they are doing a specific action. Most of the times they just can’t answer. Having a plan is not about selling your first product and have a spreadshit (yes, is well written) with fancy numbers for your investors. Having a plan is to establish objectives for the next day/week, “what do I need to know tomorrow about my business, and how I will get that information”.

Everything you do, must be part of a plan otherwise it is just garbage and vanity information. In a startup time is precious and every resource is scarce, so we need to create a plan and execute it very very fast… But don’t be worried about having a perfect plan, you must have a plan for tomorrow! I love this quote from General Patton:

A good plan violently executed now is better than a perfect plan executed next week.

Book in Loop is flawless implementing this method (not their plans, because like any other plan, it fails sometimes). They establish plans based on goals (short and medium term). They don’t even realize it, but this focus allows them to quickly change their plan and adapt to the information acquired. Everything they do has a specific objective, ultimately to achieve product market fit and grow their user base and partnerships, but that’s the big picture. This approach is critical even for meetings. They go to every meeting with a very specific objective. This way they save time. A thing that I’ve learned is that people don’t like to waste time, nobody likes it, so if you have a specific objective you will quickly understand if the person in front of you can help you or not… If it is just mumbo jumbo talk, you can forget it… “Nice to meet you and goodbye!”, you’re not a PR firm…

3- Talking to people is everything

Communicating and talking to people is a core part for every startup. Being inside your office creating something or applying to some financed projects does not assure you two fundamental things:

1) That you are building something people want.

2) That you are solving someone’s problem.

Communication and getting out of the building are critical elements for every startup. If you talk with successful founders they will probably tell you they spent their early days building their product or talking with people.

Book in Loop works this way. They have news everyday simply because they talk with people. There are so many relevant people to talk with in the process of creating a startup that in the early stages they need to talk with the most people they can. However this is not a random process. They choose specific people, relevant people for their business (key stakeholders, clients, partners, legal advice, etc). This is a quite interesting part of their approach, they look for the key people, know how to reach them, what they need to know from them, how that person can help them and establish a plan B in case their assumption is wrong. You can only validate your business by communicating and talking to people, and these guys show me that this work must be like an obsession!

4- Always know when to stop

There is always a time when you need to say “STOP” and focus in what you have, the lessons you’ve learned and establish new objectives. If you move in a fast pace, this is everyday. It is impossible to make a sustainable business if you are constantly on search mode, sometimes you need to be on thinking mode or planning mode, simply to understand the next steps! Make sure that you move fast during each step, focusing on objectives and lessons learned.

With these guys this is a daily routine. Their work culture allowed them to make this exercise everyday. They stop, they think about the results and they plan and act according those lessons. It seams simple, but in a startup it requires a lot of commitment and discipline.

5- Be passionate about your company

Each one of the founders of BiL is absolutely passionate about their business. When they talk about their product they are always smiling and talking like they are passionate or obsessed with their mission… And this feeling is contagious! This feeling make me work hard like one of them, working even on weekends with pleasure!

If you are passionate enough you can inspire others to work with you, and help you, most of the times for free! That’s a power every entrepreneur wants and should hold to have a successful startup. These guys taught me an important lesson about this. The first person you sell your idea and your vision is not a clients or a partner, but the people you are trying to convince to work with you. If you are not passionate about your idea or project you will never be able to inspire others and it will be very difficult to get help to develop your project.

6- Become a market expert

The first thing I say to entrepreneurs nowadays is that they need to become experts in the market they are addressing. They need to know all the asymmetries, all the inconsistencies and how the market behaves… By market I mean competitors, distribution channels, users, everything! I always give the example of Homejoy (the YC startup that failed last year). When they were creating Homejoy they understood their market by working as cleaning staff in other local cleaning businesses, this way they were able to understand all the inefficiencies of the process. So if you don’t know your market you are just increasing the chances of unsuccessful results.

An impressive thing about these guys in Book in Loop, is that they know every little detail about their market, and how the market works. Every single detail, every little bottleneck, everything. I mean, it is impressive! I think this is probably the most important practical lesson, if you want your startup to be successful you must become an expert, to avoid being eaten by others, or their legal departments... Know every detail to avoid problems in the future. In the first meeting with Book in Loop I’ve ask them a thousand questions about their market. Usually when we talk about how the company will make money or how the company will get clients, entrepreneurs start becoming more insecure or saying stupid stuff. I was talking to an 18 year old student, I was just waiting for this moment to happen but it never happened! It was impressive, these three guys know every thing from retention rates to logistics bottlenecks! They taught me a lot! In the first meeting I thought:

I’m not gonna guide them, I’m going to work and learn with them!”

7- Don’t be afraid of cold call someone.

Entrepreneurs I work with have a kind of Social Anxiety Syndrome. When we say that they need to talk with people they just freak out! Seriously this is pathological! So when you talk about cold calls they just run away and never come back… The truth is most entrepreneurs don’t like to talk with people about their ideas and they get the most amazing excuses to not do this, specially when cold calls are the only available option.

Book in Loop has a different approach… Just the other day they called all the major news networks and newspapers in Portugal and got exposure for free, reaching thousands of people. They do this for partners, potential clients and PR. They get things done, and that’s impressive. They called a general manager from one of the biggest newspapers in Portugal and started the conversation this way: “I my name is João, I’m just gonna steal you 40 seconds, but if you want to hang up I understand”. The guy just listened to him and wrote an article about Book in Loop! That’s awesome! They are pragmatic and result oriented, and they get their hands dirty to get the job done.

8- Acceleration programs should be based on cooperation, not one way advice.

The most interesting thing about my coaching activity with this company was the relation we created. I made friends and learned a lot of stuff. I tried to teach them a thing or two, but observing the way they are working is just enough to learn! Cooperation is the most important thing about acceleration programs, because it is the thing that lasts, much more than any project or acceleration program and can bring much more results in the future than simple advice!

9- Lying will only drag you down

Most startups have the temptation of concealing their weaknesses, hoping that no one notice… Well most of the time people notice not only one but hundreds of potential weaknesses… So if we assume all these weaknesses we are showing people that we know everything about our business, all the risks, and we can start discussing a contingency plan and stop wasting time!

BiL always assumed their weaknesses, since day 1. This knowledge that they have about every detail of their business, including the risks and weaknesses, is a distinctive detail that most people don’t even notice. The knowledge about weaknesses is a strength that we should not underestimate! Don’t get me wrong this process takes a lot of time and iterations, a lot of work and speak with lots of people. But this approach is clearly better than concealing and lying … This only shows lack of trust in our work and approach, and we don’t want this to drive our business.

Always listen

An early stage startup is about shutting the fuck up and learn to listen and observe… I get crazy when I’m with entrepreneurs and they monopolize the conversations with partners and potential clients!

AAAAAARRRRRGGGGGHHHHHHH

This is just wrong and so frustrating! In early stage we are trying to solve a problem, so we need to listen! Learning to shut the fuck up is a characteristic that every entrepreneur should learn and implement in their first days as a founder. Solving problems is about observing and listening not shout about features and product.

These are the basic lessons I’ve learned with these guys in Book in Loop… Most of it is just common sense that most entrepreneurs choose to ignore or think that are counter intuitive… I hope that this could somehow help you…

A special thanks to Pedro, Manuel and Bernardo for these weeks of work!

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João Nuno Nogueira
Ascent Publication

Love technology and its potential to bring better living conditions to people around the world. Passionate and creative problem solver.