3 Simple Questions to Ask Before You Join a Startup

The following piece is a guest post and does not necessarily reflect the opinions of this publication. Read more about MediaShift guest posts here.

I’m nearing twenty years working in Silicon Valley and my biography is a long list of two-to-four year stints at startups. I’ve had my fair share of wins. But, until recently — when I joined a streaming media startup without any funding after a few years heading growth and product marketing at Vevo — I’d never given significant thought to identifying the right conditions for joining a startup.

I believe there is a set of right conditions to join a startup, and for anyone ready to jump, there are three simple questions to ask yourself before joining a startup.

When to join?

Join a startup when you’re young.

Since 2007, I have consistently mentored young people to join startups. I’ve helped young entrepreneurs find funding, develop their product ideas and business models. Some have created significant impact and value. None have ever regretted their startup experiences. If you’re young, you will learn and get better at a startup, regardless of the startup’s outcome.

It’s about the experience when you’re young.

When I joined WebTV in 1996, startups weren’t cool, funding was scarce and the economy was not great. My fellow Stanford grads went to work at consulting firms and investment banks that don’t exist anymore. WebTV couldn’t hire fast enough, and my manager was so overwhelmed that I could try just about anything I wanted — I was a free-roaming, entry-level marketer. When new hires finally came aboard, the “more senior” people were more interested in managing than doing, allowing me to quench a thirst for experience. That startup condition is important: Senior managers get distracted by proximity to strategic discussions, which creates scarcity in doing. If you’re young, take full advantage of this condition. Join a startup, do anything your manager approves, work for peanuts, sleep under your desk, age rapidly and pray for premature gray hair. Your career will advance quickly.

When to start a company?

I recommend joining a startup when you’re young, but I don’t recommend you start a company without at least a few years experience. Entrepreneurs dropping out of college to start the next Microsoft or Snapchat are literally phenomenal. Before you start a company, get experience, observe and learn how to develop products, fundraise and manage people.

Critical Conditions: Idea, People and Timing

The idea has to be crazy.

The solution to the problem you’re solving has to be innovative from a technology and business standpoint. But, you need to have huge obstacles to success — obstacles like entrenched, well-funded incumbents and a global economic outlook rife with uncertainty. If you don’t have these hurdles, your idea probably isn’t crazy enough to attract investment and employees.

The timing should be “sub-optimal.”

Some of my favorite, most successful startup experiences happened in election years or following a major downswing in public markets. These conditions are sub-optimal for startup funding but ripe for disruption. During these times, venture investment becomes a very considered transaction, and only really good ideas receive backing. As portfolios shrink in number of investments, you’ll get the right level of strategic input and attention from your investors. KPMG’s Venture Pulse Report shows that we’re in a period following a pullback in total investments, but with more money going into previously-funded companies. Additionally, we have Brexit and Trump looming. The conditions are not optimal for receiving venture funding, but the startups born this year will be really strong.

The right people are available.

During sub-optimal venture investment times, talent tends to get “loose in the saddle.” There’s a common misperception about how top talent thinks about startup opportunities during difficult funding periods or public market pullbacks. The suggestion is that top performers react in a “flight to quality”, as if labor emulates capital investment decisions in an economic downturn. In my experience, during unpredictable times, talent views public companies as susceptible to layoffs and prone to internal confusion about priorities. Strong talent desires to take control of outcomes, and joining a startup or starting a company is one way of assuming more control over your future.

If you’re young, join where you believe there’s talented leadership. If you’re considering starting a company, open up LinkedIn and reach out to all of the talented grownups you’ve worked with in the past. Assemble your dream team.

Simple question No. 1: Is this really a startup?

Fifteen years after my WebTV experience, I was a seasoned marketing executive repeatedly playing two much-needed roles: a) turn around a startup’s economics and prepare it for acquisition, or b) grow a startup with good economics in preparation for acquisition. But, I wasn’t joining startups anymore. I’d become a specialist, remaking startups into desirable assets. This happens a lot. If not careful, a tech executive can become a mercenary focused entirely on success metrics that satisfy potential buyers instead of driving metrics signaling customer satisfaction. If you want to be in a startup, join during the seed funding stage.

Simple question No. 2: Do you like people?

Startups are for grownups.

Grownups come in all ages. Over the last decade, I’ve mentored Y Combinator grads and Thiel Foundation Fellowship winners who are more grownup at age twenty than people twice their age. Being a grownup means you like people and know how to communicate and make commitments. Here are four realizations that helped me become a grownup.

1. Grownups really like people. Chris Holmberg is a media-shy executive coach to many high-profile executives. He helped me realize how many smart and talented people are trying to be likable, trying to get good at empathy, trying to add and incorporate fundamental human qualities. But, the best leaders started life just liking people. If you want to start a company, you have to genuinely appreciate the frailty of the human condition. In a startup, you’ll see every aspect of your colleagues. You’ve got to love your teammates in all of their ugly — there’s no other option.
2. Grownups are willing to give the next five years of life to the pursuits of the startup — the people. Blindly. Think about that. Farb Nivi, founder of Grockit did that. And he exemplified it. Even after he was nearly killed in an auto accident and had to overcome so much pain in recovery, he was committed. And, after he came back to Grockit, stripped of his CEO position, he had to adapt to a new management team and renew his commitment. That’s a very hard thing to do. If you can’t do that, you’re probably not ready to start a company.
3. Grownups do the difficult thing when it’s the right thing to do, with composure. This means giving peers and employees critical feedback. It means saying the unpopular things about your startup’s product or service offering and assuming responsibility for failures. It means being really honest about the strengths and weaknesses in the management team. This strength comes from surviving and overcoming difficult circumstances. Grownups can do this over and over without losing credibility or support of the team.
4. Grownups have to be comfortable not being liked. There are a few humans on this earth that think I’m an a-hole. I even like some of those people (see no. 1 above). Those people might be right. Maybe my past successes were a fluke and the people who repeatedly work with me are deluded. I don’t really know. And I’m not immune to “The Struggle” as Ben Horowitz described. But I do know that if you can’t stand to be disliked or make the unpopular decision, you’re not grownup enough to start a company. If you work long enough, you’re going to run into a no-win situation where you can’t make everyone happy. In those moments, if you try to make everyone happy, the outcome is disastrous. Grownups get comfortable being disliked because they’re comfortable doing the difficult things.

Simple Question No. 3: Are you capable of sustained desire?

If the idea is crazy, you have the right people by your side, and the timing isn’t perfect, you need to ask yourself one more question. Do you have the sustainable desire to fight and win? And what is it that you desire? Wealth? Notoriety? Vindication?

Motivations are always personal. Make sure you understand your desire before you ask people to follow you. Whatever the source of your desire, it will be visible to the people who follow you, so be honest with everyone from the get-go.

I’ve qualified my startup conditions, and I’ve answered the three simple questions. I desire to change an industry I both love and loathe. I want to work with great talent that I’ve worked with in the past and impressive talent I’ve just recently met. The funding conditions are sub-optimal, but we’ve already received significant capital commitments and the team is coming together. The challenge is difficult, but I’m very excited about the next year.

Aaron Burcell is the Chief Marketing Officer at an early stage streaming media startup. Recently the VP of Growth & Product Marketing at Vevo, Aaron joined the company in early 2014 after a successful run aggregating and engaging millions of mobile millennials at Grockit (acquired by Kaplan/Washington Post), Outspark (acquired by Gamigo) and Gazillion Entertainment. Aaron has spent the majority of his career at the intersection of digital media, mobile apps and net-connected devices, having held previous positions at podcasting pioneer PodShow, consumer VOIP startup Jangl, search startup Stata Labs (acquired by Yahoo) and WebTV (acquired by Microsoft). An active mentor to young entrepreneurs, Aaron is frequently asked to speak at media and tech industry events on the topics of workplace diversity and product growth best practices.