Rising StarRising Star: Josh Bryant of Droplr is Revolutionizing the Way We Share Files

Josh Bryant, Co-Founder and CEO of Droplr. Photo via jshbrynt.com.

Droplr was one of 14 companies to present at OEN’s Angel Oregon Spring 2014 Showcase. Here, guest blogger M!ke Russell, principal of Pivotal Writing, LLC, touches base to learn more about how Droplr got to where it is today, and what’s on the horizon: 

In the beginning, there were floppy disks, and they were good. Then, email attachments opened up a whole new universe of file sharing. Today, you likely use the Cloud to share files.

But a fundamental challenge persists: when you share a file, you have to put it somewhere.

“In the world of product design, we would share mockups, screenshots, and other assets all day,” explains Josh Bryant, Co-Founder and CEO of Droplr. “That stuff has really short-term value. You just want it for that moment when you need it. You don’t want it crowding your folders thereafter.”

In one step, Droplr converts any file into a URL that can be sent via any communication platform. It removes these roadblocks for creative teams: compatibility issues across devices; a lack of context in collaboration and feedback; and a slow and clumsy file transfer process for visual assets.


“Portland likes to support Portland. Customers, partners, and investors want to see you win.” (Tweet this.)


“We’re doing to Dropbox what Chat did to Email”

Bryant, a refugee from Silicon Valley, holds the Bay Area’s startup culture as an example of what to avoid. “I didn’t want to make another startup that implodes after getting venture capital. I wanted to blend the startup mentality with old-school business concerns: revenue, adding value to the market, and building a customer base.”

Bryant started Droplr as a side project that occupied his nights and weekends. Slow and steady growth brought him to an inflection point. Customer support took too much time. New ideas for product development started to pile up. Bugs went unaddressed for too long.

To meet demand, Droplr needed more attention and more capital.

For a time, investors were pitched what Droplr’s leadership thought they wanted to hear. Yes, they could be enterprise software. Yes, they could be consumer Internet. Those unending turns left them drained. In December 2013, they walked away from a deal that would have finished their financing, but required them to assume yet another identity.

“It was almost a self-esteem issue. We were afraid to tell people who we were,” Bryant reflects. “When we rebuilt our pipeline, confident in who we were, that was more powerful in connecting with investors. It became easier when we actually claimed how we benefit our customers.”

If they could do it all over.

Bryant answers without hesitation: “We would do it again in Oregon. Up here, the investment community seems more attuned toward companies that are focused on revenue, adding value, and serving paying customers. They’ll support platform companies that will never be a household name, but have tangible value on the books. That’s the type of company that I want Droplr to be.”

“Portland likes to support Portland. Customers, partners, and investors want to see you win. They’re extra motivated to advocate for you. That’s a little unique to Portland.”


This guest post is brought to you by M!ke Russell, principal of Pivotal Writing, LLC in Portland, and content marketer to SaaS businesses everywhere. Follow M!ke on Twitter at @PivotalWriting.

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