Five Lessons I Learned Building a Startup


It goes without saying that every startup faces two major constraints: time and money.

Once a startup is funded, it’s a race to build a profitable business by hitting milestones, launching a product, and developing a customer base before that money runs out.

After the last year and half at NewCo, a media and events startup, I’ve learned and re-learned several important lessons that I believe are applicable to all startup leaders.

NewCo loves cake.

1. Build a Team of True Believers

There is nothing more important than hiring people who are passionate about what they do.

This is absolutely critical in a startup environment because you need people who can, and will, weather many storms. They can’t be the kind of person who gets the jitters when challenges arise. Salary cuts? They can make it work. Change of plans? They can adjust.

You need an unflappable soldier, dedicated to their craft, and not scared easily. These people will stay the course, until, well, the course has been run.

Great startup employees should have the ability to dream, because a startup is a dream. They are optimists by nature, and buy into the vision set forth by the leadership, each supporting it in their own way. The dream can’t belong to the CEO alone — it must be a shared vision, one that genuinely excites and motivates the startup’s employees to stay focused and execute.

Look for people who can handle ambiguity, who do not need specific direction, who can roll with change, and who take the ball and run with it when the company is trying to tackle something big with limited time and budget.

2. The Fearless Leader

The founder/CEO is the caretaker of the dream, typically the biggest dreamer, and puts forth the boldest vision for success.

It’s crucial this person be a fearless leader — someone people can rally around and get behind, who can see around corners to the future. The ability to be one step ahead, already adjusting to a new reality is crucial — because the company may need to pivot and change its business model, change product lines, change the very shape and structure of the team — and the CEO has to bring everyone along, and quickly.

A founder who is not fearless may not be able to get a team to move fast enough, and speed is of the essence as the company burns cash.

Aside from brains and emotional intelligence (essential), being a fantastic communicator is probably the next most important trait of the CEO. Whether the CEO chooses to inspire people with a weekly note (like my boss, John Battelle, with his Sunday note), or prefers to rally the troops in person at an All Hands meeting, his or her most important job is to keep people focused, motivated, and bought-into the vision.

3. No Sacred Cows

This goes back to the “drunken walk of the entrepreneur”. An entrepreneur looks to make a business work. To do so, various approaches must be tested, products launched, iterations made again and again.

As a startup looks for the elusive “market fit,” it often stumbles and must constantly pivot, reinventing what it’s creating and who it’s creating it for.

A startup that’s weighed down by sacred cows cannot make the pivots required of a successful company because they are too emotionally attached. An early stage startup has to be flexible, malleable, and ready to move on from a failed concept. Harboring a high degree of sentimentality toward any approach, product, or target market is dangerous.

As an advisor at Matter, a media incubator, I saw one startup team completely scrap their concept three times over the course of 5 months. The last concept they landed on was a keeper, and although they came up with it at the very end of the program, they are still in business today. If they hadn’t been flexible enough to pivot fast and quickly, they never would have arrived at the right concept.

4. Articulate the Mission

The difference between a company that is driven by a well-defined purpose and one that isn’t is monumental.

When a startup’s purpose is made crystal clear, and employees understand their role within that purpose, the staff will buy in, drink the kool aid, and work hard to achieve the company’s goals.

When the mission is undefined or when the goals aren’t clearly laid out, employees will not feel a strong sense of purpose, or maximize its return on investment in talent.

I’d wager to say the product would suffer as well and the company would not build anything of lasting value.

You can read more about this topic in John Battelle’s piece on knowing your purpose.

5. Cultivate Team Spirit

It’s hokey, but no less true, that it’s important to foster a strong team spirit.

Whether this entails taking time to joke around on Slack, getting together for lunchtime potlucks, having a team book club, or doing semi-annual offsite retreats, work should be fun.

At NewCo, we road tripped to Santa Cruz, rented a house with a garage conference room, and cooked dinner together in a tiny kitchen. It brought our team of 20 closer together, walking on the beach at night, giggling under the stars, and seeing our head of sales bust out with the worm on the living room floor.

Yes, work is about the company you are building, but equally important are the people with whom you are building it. Your colleagues are your buddies, your trench-mates, and the people who will inspire you to “keep on keepin’ on.”

Fostering a solid team dynamic is a great investment in building a lasting company culture. And besides, work is much more fun when colleagues take the time to get to know each other and build personal bonds.

That’s all I’ve got for now. Go forth and build great companies, startup people.

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