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6 Tips For Navigating Your Role As An Entrepreneur

6 Tips For Navigating Your Role As An Entrepreneur

On August 17 I went to the YC Alumni demo day in Mountain View. As the class of Summer 2015 proudly pitched their ideas in perfectly rehearsed two and half minute pitches, my multitasking mind thought about how much time has passed since Vasco Pedro, my fellow co-founder and CEO, presented Unbabel on that same stage in March 2014. It felt like eternity. I began to think further back to my first startup, a total disaster that left me penniless in 2012, then to when I quit my job to start a female beauty company that never made off the paper, and to my first job in tech in 2005. It’s been 10 years since I embarked on my journey in this crazy world of startups, technology, subscriptions, and hyper growth, and became an entrepreneur.

Being an entrepreneur is a difficult job that we’ve all chosen for different reasons, but the underlying motivation is our passion for ideas that we believe in so much that we’re willing to do what it takes to make them come to life. After having worked with startups around the world, I’ve gathered enough experience to last me a lifetime. Here are my top six tips for navigating your role as an entrepreneur.

Know your self worth

It’s easy to confuse your self worth with the growth rate of your company, how much money you raised, or how many times you heard the word “no” this week. After co-founding ActualSun, the team imploded and we failed to build a product, lost our pilot customer, and the trust of our investors. I thought I failed as a manager and as a person. Looking back I realize it was just a bruised ego and allowing myself to think that way only made it harder to get back on the horse and try again. Building a company is a 24/7 job and it’s natural to obsess about what’s going on with your startup. Thoughts are constantly swirling through your head about how to grow, who your customers are, how to sell, who to sell too, how your ideas stand out, and how to communicate them in a meaningful way. When you spend so much time thinking about something, you begin to identify personally with it. It stops being your company and starts being you.

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But it’s not. You’re a worthy, unique, valuable human being just because you are you. There is no point in identifying yourself too much with your failures or successes. If you get down when the business is down, it’s much harder to turn it around and you might fail to see the window that opens when that door is slammed in your face. Balancing your reactions to the ups and downs of your business is all about remaining confident in the face of failure and maintaining modesty in your success.

Keep calm and try again

If you ever met me in person you’ll see “Keep Calm and Try Again” is actually my phone’s screensaver. As entrepreneurs we naturally see ourselves as leaders and are always striving to succeed. Our desire to be the best often causes us to go into a bit of a panic when things don’t work out the way we had hoped. A large majority of the things we work on will fail and on multiple levels; weer that’s your campaigns, channels, customers you go after, or people you hire. You will make mistakes and lots of them, but that just means you’re making decisions and taking chances.

In a way, it’s like A/B testing everything. I first started getting used to trying things when I worked for TIMWE. We did a lot of online ads, and had tons of different landing pages. We would test if a particular piece of content would sell, a new affiliate network, or a new banner design. It sounds basic, but this was in 2006 before Unbounce and Optimizely made it easy, we were running these experiments manually. The marketing team discussed our experiments as a group on Monday mornings and if it worked we’d do more, if not, we’d try something else. You can apply that to literally everything! Remember, each attempt is a learning opportunity, a teachable moment. The silver lining of any failure, is what you learn as a result. A friend of mine summarized it perfectly by saying, “Learning is what you get when you don’t get what you want.” I love that sentence and always look for what I learned in each project. If you can take your failure and turn it into an opportunity for growth, you and your company will be able to turn failures into success.

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Become a well rounded person

Even though you might feel like you don’t have enough hours in the day, taking time away from work to hone different interests, hobbies, and passions is good for business. Aside from it being a good stress release, it makes you a richer and more well-rounded person and opens you up to meeting people with different opinions, skills, and experiences than you. All my YC batch mates (Go Winter 14!) have some kind of interest that helps take their mind off work and do things with different people. They participate in a range of activities from stand up comedy, paragliding, and team sports, to climbing mountains, camping, building cities in the desert, and cooking. And me? I did my first triathlon on August 23!

The beauty of adding more dimensions to your life is that it will actually make you a better founder. Here’s a secret, as an entrepreneur you’re always selling the vision, the technology, the company, to investors, customers, employees, family, and friends. Selling is all you do, and it’s much easier to sell if you can create rapport with people around other things you might have in common aside from your company.

Remember you’re not alone

I hear these phrases time and again, “most startups are shit-shows”, “there is always something broken”, “the problems are just different when you grow”, “as a CEO I focus on the part of the company that is under performing the most and fix it.” Every step of the way, from idea to IPO, hell is always about to break loose and something that might kill your company is always about to happen. Not only do we all have some type of problem to solve, we all think we’re the only ones. We’re not, everyone goes through the struggles of building their business.

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I have a group of startup friends I have dinner with once a month just to talk about the companies we are building in a friendly supportive environment (with good food and wine). Find your peers, start a group, get together regularly, and talk it out. Just sharing dilemmas out loud is often half the solution, and as an added bonus, you say them to a room full of other entrepreneurs who can draw on their experiences and offer advice.

Practice your people skills

Dealing with other people is hard, and it’s crucial that you learn to be great at it. Find ways to make people do what you want even when you don’t have hierarchical power over them. No, I don’t mean be manipulative. What I mean is, make people want to work for you. Learn what interests the people you work with, how they want to expand their skill sets, and how you can help them. Knowing these are critical for a successful business.

There’s a new contract between companies and people. In the old days people were resources who gave themselves to companies in exchange for predictability, security, and a job for life. Today, that type of employment is a distant memory. There’s no predictability anymore, so instead of searching for jobs that can provide security, people want jobs that offer them the opportunity to learn, better themselves, and work in a variety of capacities. It’s your job to create those opportunities for them and to make sure your team is naturally aligned with where you’re going and want to be with you for the ride.

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Respect your co-founders

The way you communicate with your co-founders sets the tone for your whole company. You and your team of founders are the backbone of your startup and set the company-wide example of how to be team players. When business gets stressful, your co-founders are your support system and are just as invested in the success of the company as you are. Always assume they are doing the best they can and working as hard as they can. You didn’t choose each other randomly, it was a conscious choice to go into business with one another and when times get tough, it’s important to remember that they are invested and deserve your respect.

It’s equally important to never let doubts or unspoken pain fester. Everyone is human and falls prey to outbursts that come across as disrespectful. At Unbabel we call that emotional debt, and unlike technical or sales debt, this isn’t the kind of debt that you can afford to pay back later. A startup is like a relationship and when doubts and resentment begin to build up, they are bound to surface in the throes of another issue. So don’t let it build up and have the tough conversations about your stress, fears, and needs, and listen to those of your founders and your team. Make sure to find ways to make everyone feel valued and part of the team. As a way to avoid a build-up of emotional debt, take company trips and do something fun to build a strong connection between each member of the team.

These tips are helpful for every entrepreneur who wants to navigate successfully through the minefield of living the startup life. Implementing these key strategies will help you develop yourself personally by having a grounded sense of yourself and becoming more well-rounded and empathetic. You’ll grow your business by remaining calm in the face of failure and looking for the next opportunities. Finally, you’ll be better equipped to nurture your team by removing emotional debt and promoting an environment of mutual respect. If all else fails, listen to your gut and remember that you catch more flies with honey than you do with vinegar.

Featured photo credit: Navigator/ Thomas Abbs via flickr.com

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Last Updated on March 29, 2021

5 Types of Horrible Bosses and How to Beat Them All

5 Types of Horrible Bosses and How to Beat Them All

When I left university I took a job immediately, I had been lucky as I had spent a year earning almost nothing as an intern so I was offered a role. On my first day I found that I had not been allocated a desk, there was no one to greet me so I was left for some hours ignored. I happened to snipe about this to another employee at the coffee machine two things happened. The first was that the person I had complained to was my new manager’s wife, and the second was, in his own words, ‘that he would come down on me like a ton of bricks if I crossed him…’

What a great start to a job! I had moved to a new city, and had been at work for less than a morning when I had my first run in with the first style of bad manager. I didn’t stay long enough to find out what Mr Agressive would do next. Bad managers are a major issue. Research from Approved Index shows that more than four in ten employees (42%) state that they have previously quit a job because of a bad manager.

The Dream Type Of Manager

My best manager was a total opposite. A man who had been the head of the UK tax system and was working his retirement running a company I was a very junior and green employee for. I made a stupid mistake, one which cost a lot of time and money and I felt I was going to be sacked without doubt.

I was nervous, beating myself up about what I had done, what would happen. At the end of the day I was called to his office, he had made me wait and I had spent that day talking to other employees, trying to understand where I had gone wrong. It had been a simple mistyped line of code which sent a massive print job out totally wrong. I learn how I should have done it and I fretted.

My boss asked me to step into his office, he asked me to sit down. “Do you know what you did?” I babbled, yes, I had been stupid, I had not double-checked or asked for advice when I was doing something I had not really understood. It was totally my fault. He paused. “Will you do that again?” Of course I told him I would not, I would always double check, ask for help and not try to be so clever when I was not!

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“Okay…”

That was it. I paused and asked, should I clear my desk. He smiled. “You have learnt a valuable lesson, I can be sure that you will never make a mistake like that again. Why would I want to get rid of an employee who knows that?”

I stayed with that company for many years, the way I was treated was a real object lesson in good management. Sadly, far too many poor managers exist out there.

The Complete Catalogue of Bad Managers

The Bully

My first boss fitted into the classic bully class. This is so often the ‘old school’ management by power style. I encountered this style again in the retail sector where one manager felt the only way to get the best from staff was to bawl and yell.

However, like so many bullies you will often find that this can be someone who either knows no better or is under stress and they are themselves running scared of the situation they have found themselves in.

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The Invisible Boss

This can either present itself as management from afar (usually the golf course or ‘important meetings) or just a boss who is too busy being important to deal with their staff.

It can feel refreshing as you will often have almost total freedom with your manager taking little or no interest in your activities, however you will soon find that you also lack the support that a good manager will provide. Without direction you may feel you are doing well just to find that you are not delivering against expectations you were not told about and suddenly it is all your fault.

The Micro Manager

The frustration of having a manager who feels the need to be involved in everything you do. The polar opposite to the Invisible Boss you will feel that there is no trust in your work as they will want to meddle in everything you do.

Dealing with the micro-manager can be difficult. Often their management style comes from their own insecurity. You can try confronting them, tell them that you can do your job however in many cases this will not succeed and can in fact make things worse.

The Over Promoted Boss

The Over promoted boss categorises someone who has no idea. They have found themselves in a management position through service, family or some corporate mystery. They are people who are not only highly unqualified to be managers they will generally be unable to do even your job.

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You can find yourself persistently frustrated by the situation you are in, however it can seem impossible to get out without handing over your resignation.

The Credit Stealer

The credit stealer is the boss who will never publically acknowledge the work you do. You will put in the extra hours working on a project and you know that, in the ‘big meeting’ it will be your credit stealing boss who will take all of the credit!

Again it is demoralising, you see all of the credit for your labour being stolen and this can often lead to good employees looking for new careers.

3 Essential Ways to Work (Cope) with Bad Managers

Whatever type of bad boss you have there are certain things that you can do to ensure that you get the recognition and protection you require to not only remain sane but to also build your career.

1. Keep evidence

Whether it is incidents with the bully or examples of projects you have completed with the credit stealer you will always be well served to keep notes and supporting evidence for projects you are working on.

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Buy your own notebook and ensure that you are always making notes, it becomes a habit and a very useful one as you have a constant reminder as well as somewhere to explore ideas.

Importantly, if you do have to go to HR or stand-up for yourself you will have clear records! Also, don’t always trust that corporate servers or emails will always be available or not tampered with. Keep your own content.

2. Hold regular meetings

Ensure that you make time for regular meetings with your boss. This is especially useful for the over-promoted or the invisible boss to allow you to ‘manage upwards’. Take charge where you can to set your objectives and use these meetings to set clear objectives and document the status of your work.

3. Stand your ground, but be ready to jump…

Remember that you don’t have to put up with poor management. If you have issues you should face them with your boss, maybe they do not know that they are coming across in a bad way.

However, be ready to recognise if the situation is not going to change. If that is the case, keep your head down and get working on polishing your CV! If it isn’t working, there will be something better out there for you!

Good luck!

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