You cannot discover new oceans unless you have the courage to lose sight of shore.

– Admiral Rickover

As I was gearing up to graduate from business school, one of my professors, Joel Peterson, challenged us to think differently by flashing the quote above in one of our last lectures.

Embracing this concept, I turned down an offer to go back to my previous employer and spent the next four months after school, unemployed, on an unfamiliar ocean. I spent the summer months analyzing my skills, my passions, and what I wanted out of my career. All winds pushed me towards joining a startup that I was passionate about – somewhere I could make an impact. So like a cougar chasing down fresh meat at the Rosewood on Thursday night, I was all over it.

I was able to lose sight of the shore and along the way, I’ve learned invaluable lessons at a startup. This is what I learned in my first 100 days:

1. Embrace Ambiguity
I love this quote from Facebook’s Sheryl Sandberg:

I always tell people if you try to connect the dots of your career, if you mess it up you’re going to wind up on a very limited path. If I decided what I was going to do in college — when there was no Internet, no Google, no Facebook . . . I don’t want to make that mistake. The reason I don’t have a plan is because if I have a plan I’m limited to today’s options.

Inevitably, the landscape, the players, and the movers, of startups change. Ten years ago, the entire market cap of the social media sector was less than $100m. Today, Facebook is valued at 100x that. Working at a startup, not only do you have to embrace ambiguity, you have to count on it. Building out the right team, the right skills to take advantage of these waves will be instrumental to not only your company but also your career.

Being at a startup means that you have to solve ambiguous problems – if someone had already figured this out, your startup wouldn’t exist. The nature of a startup means that you never have the perfect answer but you have the right framework to make the best decisions possible. Ambiguity is the name of the game, and you gotta be able to roll with it.

2. Build a Network – It’s Important
Startups are built on servers, engineering code, lofty ideas, VC money, etc., but the end of the day it’s a people business. Understanding the pain points of people and understanding how to work with people – that’s it. Whether you’re investing in startups or building a team at a startup, it’s all about people.

Building your own network is important. Startups move quickly and you’ll never know where you may need help. It may be the engineer that you randomly met at a dinner or the community manager you met partying at SXSW – having contacts and building your ecosystem can help you navigate through the valley.

How many times have you done the “LinkedIn lookup” — after meeting someone you immediately look them up on LinkedIn? My friends use this to prescreen meetings, source opportunities, and even diligence for dates.

Each community has its own closed networks and it takes time, hustle, and serendipity to break into these networks. The sooner you realize this and start building up your own, the better off you will be. Roles at firms may be short, but careers are long – make sure you build your network and maintain a great reputation.

3. Be a Direct Communicator
Your word is your bond, especially in tech. Oftentimes, things move so fast in deals you don’t have time to do paperwork and have to rely on “bro NDA”. Being upfront, direct, and open with partners, colleagues, and investors is always the best policy. Building this social currency will make your life a lot easier as time goes on. Time is money in startups, and no one likes to be BS’ed around.

Being a direct communicator is a skill learned over time. To be able to understand others’  intentions, take complex issues and articulate them in a simple manner, and being direct with confidence when needed is important in an ambiguous world. Even internally, trust is gained by being able to communicate and articulate issues to coworkers. Startups are so small that you know everyone’s business at work – beat this to the punch by being open with your thoughts.

4. Be Part of The Culture
Life it too short to do something you don’t like. When I was unemployed, I kept on referring back to Steve Jobs’ philosophy:

If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something.

If you weigh the likelihood of startup success against the average compensation (cash + equity for an employee), you’ll see that most employees won’t be partying on a boat with Diddy anytime soon. Founders, hired guns, and super early employees are the ones who are more likely to have the opportunity to make it big. The goal is to get yourself to be in one of those positions.

In the interim, and hopefully later on in your career, you gotta love what you do. The culture of the startup you work for will heavily dictate this. I remember studying about culture in business school and thought it was just a bunch of BS. But in real practice, this is what keeps the drum beating. People bust their asses because they love their job. The goal is to align this culture with the startup’s goals – if you do, you’ve really hit the jackpot.

The one other thing is that you have to be part of that culture. You have to live and breathe it (OK, drink the Kool-Aid), otherwise that extra hour you spend in the office, you’re going to be regretting it. If you don’t like something, try to change it. If you can’t change it, leave, because you’re wasting your youthful energy.

5. Look For Quick Wins
Coming into a startup, you have to prove yourself. You have to demonstrate to the team, the founders, and the investors why they gave up a percentage of the company for you to join. This is always not easy to do – especially if you come from a “non-tech” background.

You have to really assess your skills and use your past experience to look for quick wins for yourself and the company. I spent nearly eight years in finance (i-banking and PE), and coming to a startup, it wasn’t clear to me what my quick win was. As the company grew bigger, we started to analyze a lot of things that fell into my wheelhouse (business model changes, M&A, financial analysis, strategy, etc.). I used my previous skill sets to help where I could. I was able to help with analyzing, doing the due diligence, modeling out, and structuring the strategy around our first acquisition.

Finding wins that you can really help deliver puts wind behind your sails.

I’m sure there are hundred’s of other lessons to be learned, but these were the ones that have helped me thus far. Finding out your passion and following it religiously is the only way to be happy, as it serves as your compass out on an unfamiliar ocean.

[This story appeared on Don Hoang’s personal blog and is published here with permission.]

Don Hoang is Director of Business Development for Klout, which measures influence across the social web, analyzes social network user data, and identifies influential individuals based on the impact of their opinions, links, recommendations and other online content. He holds an MBA from the Stanford Graduate School of Business and is active in the Stanford and startup community. He currently blogs at and you can follow him on Twitter @dghoang.

[Top image credit:  LSaloni/Shutterstock]