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.

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.

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 your 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. All mg, 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.

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.

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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