Leaping into the startup world

Leaping into the startup worldAdvice from the Trenches

I joined Imgur’s Product Management team last September after three years at Flickr (Yahoo), but leaving a big company for a startup was not an easy decision.

For me, the allure of a startup, specifically Imgur, is the ample opportunity for leadership within the company, the ability to affect change within the product without the red tape, and the intimacy of working in smaller teams. What makes Imgur unique is the massive user base of 150 million monthly active users. Other similar sized startups simply do not have the user scale that Imgur already holds. At Imgur, I could work in a small, scrappy team to build a product that delights millions instantly — a product manager’s playground! And of course, it doesn’t hurt that Imgur is backed by the best, Andreessen Horowitz.

Despite the appeal, I had some reservations about making the move to a startup. Those include:

  • The risk of the company failing
  • Balancing long hours with family responsibilities
  • Working within a nebulous organization structure

Now that I’m more than 8 months into the role, I’m able to assess and dismiss my initial reservations.

Risky Startups Vs. Safe Large Companies

Startups can definitely be risky, but the amount of risk compared to a large corporation is a little overblown. Large corporations provide the illusion of stability, but you are likely part of a small team within that company and at the business unit, department, and team levels there are reorgs, managerial changes and potential layoffs. These changes create instability and tend to hurt morale and progress. And you never know when the company will decide to shut down your product or close your office.

With a startup, yes, you could run out of cash, but you have greater visibility into the burn rate and runway. Also, because you can impact change quickly, you can play a big role in avoiding this situation.

Work-Life Balance

As a father of two kids under the age five, it’s challenging to spend long hours in the office. Even beyond long hours, you need flexibility to manage needs at home like sick kids, appointments at school, etc. Additionally, I have one hour commute each way, which makes it really difficult to head home on a moment’s notice. Thus far I’ve been able to direct my schedule as needed, perhaps even better than previously. Startup culture is surprisingly flexible with hours in the office as long as the work gets done. Additionally, we have the flexibility to use third party software tools that make our lives easier, as opposed to being stuck with IT-approved tools. And even better, I have fewer meetings so there are fewer reasons that tie me down in the office.

Lack of Structure

Startups and organizational structure are two words that usually don’t go together. Startups must be nimble and too much structure can impede decision making or tactical execution. Also, a growing startup is hiring talent with all levels of experience, which means teams and leaders are always changing. This may feel awkward for someone coming from a large company with many layers of management. At a startup it may not be clear what a promotion may look like because managers tend to lead large heterogeneous teams. One benefit to limited structure is an open door policy so anyone is accessible and approachable. Another benefit is there are no siloed areas of ownership, so if you see an opportunity for improvement, you run with it. Finally, titles don’t matter — it’s all one team with one goal — no politics to navigate.


Leaving your current job for a new role is daunting and exciting experience whether the new company is big or small. You are leaving familiarity and comfort for a place where you have to prove yourself, learn how things work, and build credibility. The right role and company is based on a lot of factors, e.g. scope of the role, company values, compensation, etc., but don’t let stereotypes get in the way of considering what could be the more exciting and educational experience — joining a startup. I would love to hear about your experiences, whether similar or wildly different, and happy to answer any questions about Imgur.

This article originally appeared on Medium. It has been republished here with the author’s permission

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Rajiv is a product manager focused on social media. He is currently at Imgur building delightful experiences for users on mobile and desktop.You can follow him on Twitter and Medium

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