Josh May: a brief history.

Part I: iWait

When I was 18, a business fell into my lap.

It was 2007 and the original iPhone was just about to launch. Inspired by a story of a woman paying $500 for a place in line for the PlayStation 2 a week before, I rallied a group of friends to be first in line with no intentions of buying the phone, but rather auctioning off our spots in line to the highest bidder.

A local station, covering the iPhone release, decided to incorporate the high school students selling their spots in line. After trying to take bids via phone, we were quickly overwhelmed and were in desperate need of a online solution. I twisted an old friends arm to quickly put up a site. iWait was born. The site had 15,000 visits within the first 15 minutes, bids rose to $1500 per spot, and we were all over the news and major blogs within hours. (Incidentally we were literally among the first people that waiting in line for iPhones. You know the lines you still see for iPhones? We contributed to the beginning of that culture.)

iWait was the perfect bridge between people who had time but no money and someone that has money but no time. Targets were endless; the DMV, theme parks, concerts, Air Jordan sneakers. If there was a line, we had a waiter.

We knew time was money so we expanded our services for any odd job. In a time before the explosion of professional profiles, before mass adoption of LinkedIn, before TaskRabbit, the potential was obvious. We needed to create dynamic online resumes with videos, ratings, comment systems and more.

I didn't know how to code and I didn't have the money to hire a local engineer so I used all my line waiting money to hire programmers in India. Outsourcing was an incredibly frustrating experience. I was up for calls at 4am. Communication was always an issue. I’d say something like “make the corners round” and they’d come back with a circle, and I’d have to explain what I mean by rounded corners. Every little thing was like this.

By the time we were done with this, it was months and we had a barely working MVP, but it was enough for me to get a few thousand college students to sign up quickly. I was running it out of my dorm room with my twin brother and not making a dime. I need to get through college, I need to get more experience, and needed to be better equipped to take on something like this.

Part II: College

During college I toyed with starting another business. I had a sea of ideas, and I would win good money by pitching them at business plan competitions at school.

But at the end of the day, I wasn’t equipped to execute any of them, just like with iWait. I would go to the computer science building to try and get one of the students to help me with my latest idea. I was envious of those guys. They had the power. They can take their own vision and bring it into reality. I couldn’t.

I got fed up and learned to code.

The moment I made a red box rendered on the screen, my eyes widened. It was the closest thing I can describe as a superpower. The feeling was liberating, much like how I would imagine it would feel if I was to crack a lock to a huge safe.

And so I got through college, went through developer bootcamp at General Assembly, and came out like a coiled snake ready to strike. I had a million ideas, and I could now build them MYSELF.

So everything I thought of, I built it, throw it out into the world, and see if it would stick. In practice, this ended up with me obsessing on the development of a startup idea for a few months, learning a ton, and then for some reason or another moving on to another idea.

Incidentally, that’s when I met my current co-founder Ben, an engineer who had just gotten his PhD at Berkeley and was similarly obsessed with starting companies. I started driving 2 hours into Berkeley to buy him a beer and talk about code or work together on a project.

Part III: Era of the Micro-Startup


A March Madness pool. Because the one’s that existed online sucked but were still making big bucks. Never got to launch but learned a ton of Rails.

Pirate Weasel

Use basic HTML5 to create a fake label for a water bottle. Say, write some answers to your upcoming exam in the ingredients list. Print it out. Put said label on a water bottle. Resulted in some A’s that might not have been deserved. And coverage on Fox news online and whole bunch of other news outlets. Got hundreds of thousands of views. A group of concerned educators wrote me a note showing their concern. I felt bad.


I made StudyPup to redeem my name in the eyes of my mother (who is also an educator) after Pirate Weasel. StudyPup is a set of educational web-based games for elementary school kids. It’s designed according to the teaching philosophy of differentiated learning, meaning the difficulty level changes dynamically based on the student’s ability, and the teacher can observe the progress of each student. It’s been used in 6 classrooms and dozens of students, and many of the kids come back regularly. I moved on to other projects.

Maxwell Powers

Why do music videos look the same that they did in the 1980s? HTML5 just came out, can we use that do make a music video different one that has ever been made? Ben and I set out to combine a physics engine with a music video we filmed and mapped into 9 segments. We were featured on Google Chrome experiments and the video has been viewed hundreds of thousands of times.


Buffer but with a cool UI and some different features, before Buffer got big. Started me thinking about how to take complicated data and processes and make them digestible and simple. How can you parse of the buzz of social media to give useful information for a business? Got distracted with Boatsavi.


Like a Twitter for discussion on stock prices. If you make a comment you have to identify as either bullish or bearish. So the idea was to easily “cut out the noise” and have a clear index of public perception on stocks and some valuable data. Learned how to scrape data and connect with APIs for the first time. I ended up giving it to my little brother, “the baby bull”, and focused on Boastabi.


The industry of boat trading online looks like it’s stuck in 1995, what if we update it. Here is an untapped industry with loads of value to be created if it can be made more modern. By this time, my design chops were getting pretty good and I built a backend in Rails. The product looked great. We didn’t have a ton of users, but the business owners that we did have kept coming back and posting boats regularly. I learned a ton about how to design online tools for largely nontechnical users. But ultimately I realized, I want to tackle a large problem than the online boat industry.


Combine 3 images to make a clever meme. Never really got much traction. Learned a lot of javascript.


A web operating system mixed with consolidation of your cloud storage accounts. So your Google Drive and Dropbox and Box etc accounts can all be linked and aggregated all in one place. Like a “meta-box.” And with a really sweet web operating system interface that feels like a native OS experience. Was only going to get this product live if I could convince Ben to help me build it, but we decided to start POWr instead.


My first real foray into web plugins. Ben and I developed a video slider and resume app to see if we could make some money on the side. The data that came back gave us valuable insight when starting POWr. Technically, it gave us a year of developing font-end heavy web plugins so we were veterans by the time we launched POWr. Most importantly, it gave us firsthand access to a sea of people that, like I have often experienced, were having trouble getting their business online.


The biggest thing I learned from my era of micro-startups is this: There are so many challenges between having an idea and executing it.

There are millions of people experiencing these challenges every day. Everyone has ideas about how we can change the world.

What if you could make a tool that brought down that barrier of execution? What innovation and progress could the entire world experience if there were better tools to build businesses? That is the problem I want to solve. That is power. I mean, that is POWr.

Part IV: POWr to the world

Now with a few battle scars, a dozen broken laptops, gallons of coffee digested, a few dollars earned, a few dollars lost, and a million lessons learned, I became determined to eliminate the friction between an entrepreneur and their ambitions so THEY DON”T EVER HAVE TO GO THROUGH EVERYTHING I HAD TO...EVER!

Which is why Ben and I then started POWr, a radically new approach to solve the difficulties small businesses face in building and managing their web presence.

POWr is a toolkit of core website components that give nontechnical business owners the power of a silicon valley dev shop. POWr users can add forms, galleries, social media integrations, ecommerce, and more to any webpage in a few minutes. Users can then edit and manage these applications right on their live webpage, from a desktop, tablet, or mobile phone, with zero code.

Because the Picasso's of the world shouldn't have to go into the woods and cut down a tree in order to make a paintbrush.