The Startup Worker as Venture Capitalist

This winter, after five years of helping build LevelUp into the strong mobile payments player they are today, I decided to embark on a new challenge with Swipely.

It wasn’t an easy decision. I had complete mastery over LevelUp’s enterprise offering, we were coming off our best enterprise sales quarter ever, I had built strong personal relationships with the team through failures, pivots, and successes, and this year would be one of seismic shifts and excitement in the mobile payments space.

And yet, I made the jump confidently and landed with two feet in a fast-growing payments and analytics startup that is instilling within me the methods of their success and is eager to tap my experience to grow their national division. This next phase will be incredibly exciting and challenging. Following the advice of Nietzsche, “build your cities on the slopes of Vesuvius. Send your ships into uncharted seas.”

The job change decision-making process is incredibly complex, and it’s difficult to create a model for yourself let alone an entire category of job-seekers. There are a number of open positions available in most job categories in major metros, so which startups should you pursue? My company search criteria soon became a hybrid of startup DNA and values I developed myself and others I adopted from investors I admire.

In many ways, startup workers are like venture capitalists. Investors are looking for the classic triple-threat of team, market size, and product. The end-game for investors is cashing out on the other side with a 10x win. Startup workers are looking for the next rocketship product to build or sell, so why not follow the venture investment model to make your decision? Check out my tech job search criteria below:

The company is building something people want

Paul Graham has become famous for this motto, which has become something of ultimate aspiration for the young guns at YCombinator. But PG has a point. A company can only go so far on enthusiasm and confidence. Great companies build something a large number of people want a small amount or something a small number of people want a large amount. The best products spread through word-of-mouth recommendations and referrals.

The CEO works harder/longer than everyone at the company + can magically see six months further into the future than the competition

A long time ago when I was right out of undergrad, I worked for a startup in which the CEO came to work late every day, played techno music for a few hours, blasted out some emails, and left with everyone else. Startups need a leader who instills a high level of confidence in their team, someone who will hold the company’s torch high during periods of extreme stress and setbacks and also great victory. Industries are changing quickly because of technological disruption, and leaders who have the foresight to see where their category is shifting will put their startup in the best position to win. A little weirdness doesn’t hurt either!

The startup has momentum

VCs aren’t looking to invest in companies with linear growth, and startup workers aren’t geared to want to work for them either. Borrowing a bit from Mark Suster, many of the best companies have seen encouraging levels of traction. Significant growth in the number of paying customers, top line revenue, users, and channel partners drive VC checkbooks out of pockets and hordes of prospective employees to a company’s door.

The startup boasts a top-flight roster

People. People. People. It’s easier to put your fist through a brick wall than get VC funding without a stellar team. The same should apply for startup workers in the job hunt. A product might seem to be growing like a weed, but 9 times out of 10 a well-executing team made it hum. There is no easier way to build self-motivation and enthusiasm for your job than being surrounded with intelligent, driven co-workers. Make sure your interview process includes conversations with prospective colleagues and members of other departments you’ll be interacting with on a weekly basis. Just as you are the average of your five best friends, you are the average of your five closest colleagues.

A huge potential market awaits

Pass the Kool-Aid. If you’re looking to be a part of a hyper-growth company, the executive team must have their sights set on a large market opportunity. Small markets turn startups into lifestyle businesses or services companies that produce singles and doubles, not home runs. But don’t be fooled into thinking a startup is going after a small market due to their current go-to-market strategy…they may have bigger ambitions and pivots planned. Do your diligence and ask questions about the company’s 2-year product and positioning trajectory.

You have subject matter proficiency

Investors love to put money to work in fields they know. Having intimate knowledge of an industry and its competitors makes a VC more valuable as a trusted advisor. A startup worker with industry experience and insight can more quickly assimilate into an organization’s culture and help chart the path forward.

How much risk are you willing to take on in your job search? The answer to that question will determine whether you’re an angel investor, apt to go for more risky opportunities with higher potential reward, or a Series A, B, C, or D venture capitalist, choosing to work for companies with more longevity and de-risking under their belt. There is no one size fits all criteria, and everyone will think about the challenge differently. Just promise me you’ll do your diligence.

The Startup Worker as Venture Capitalist

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