How to Fail Well and Still Become a Successful Entrepreneur


Is There such a thing as ‘Fail Well’?

Absolutely! most experts including millionaire and TV celebrity Dragon/Shark Robert Herjavec agree that entrepreneurs will fail many times before they find a product/service that hits the mark and is successful.  But Lauren Long knows how to fail well.

lauren-longLauren Long knows this all too well.   She even wrote an essay on how her first entrepreneurial venture, called “Taskers” failed.  Entrepreneurs like Lauren know we can learn more from our failures than from our successes.  She learned to ‘fail well’.

Lauren lives in San Francisco but her startup, called Boxit, is in Toronto.  Lauren and her team took a mundane task of storing your excess “stuff” and married it with technology.  Boxit seamlessly delivers a much needed service for downtown Toronto residents with lots of gear and very little storage space.

How did you come up with the idea of Boxit?

box-it   store-itget-it

Box It                    Store It                   Get It

Boxit was conceived by my co-founders Gordie Best, Michael Fok, and I after we were working on another startup idea for a few months which didn’t quite take off. We all moved to Toronto to start a company together, and all experienced the pains of figuring out how to manage our stuff, and where to store them during temporary housing. We had a eureka moment where we realized that we can be solving that problem for others.

How long did it take you and your team to go from concept to market launch?

It literally only took a day. We were sitting around a room brainstorming ideas, and all fell in love with Boxit as soon as we came up with it. I then bought a domain and launched a bare-bones website the next day. We got our first customer, and rented a Zipcar to deliver boxes to her that very evening.

What problem does BoxIt solve?

The first time I visited a storage unit, I felt uncomfortable and unsafe in the warehouse-looking building. I didn’t know how to operate the freight elevator, and I couldn’t believe that I was paying hundreds of dollars a month just to store a few boxes. My co-founders and I thought that the self-storage experience could be much simpler, cheaper, and delightful. Boxit brings sturdy plastic bins right to our customers’ doors, pick them up when they are packed, store them in a secure facility for only $7 per month for each box, and deliver them back on-demand. The whole experience is facilitated by our webapp, which allows our customers to book pick-ups and drop offs, and catalogue their boxes.

Do you have any plans to franchise BoxIt or expand to other major cities in Canada or overseas?

We don’t have immediate plans to expand Boxit outside of Toronto. We do believe that Boxit offers a much-needed service, and would certainly like to see it in other cities.

How do you juggle your roles at Boxit with your other gig as a software engineer at Google?

We worked hard to systematize as much of our company as possible in the last 3 years. We work with a great partner company for our deliveries and storage logistics, and we have a highly capable City Manager, Danielle Dinunzio, who takes care of our day-to-day marketing and operations and ensure that our customers are well taken care of. My current involvement in Boxit includes offering strategic oversight, and owning the technical components – which I find time to do during evenings and weekends.

What have your learned from launching a startup company?

I learned the importance of failing, and how to fail well. (Yes, there is such a thing as failing well!) I wrote about this in my essay How My Startup Failed, and Why I’m Glad It Did.

What is your favourite part about living in California?  How does this life differ from life in Toronto?

Everyone in San Francisco is a transplant, I rarely meet someone who is native to the area. That means that everyone is living outside of their comfort zone, therefore they are very willing to connect with each other and help each other out. While Torontonians are very friendly and helpful as well, the volume and quality of relationships I’ve been able to build here in a short amount of time is something I haven’t experienced before.

Do you see yourself as a serial entrepreneur?

Absolutely. Although I’m in no rush to start another company. I do not want to start something for the sake of it, I would only want to pursue an idea I’m truly passionate about, with people that I truly enjoy working with.

What do you see as the next evolution of monetizing the internet?  Is it the continuing evolution of mobile apps or something else?

I think we’ll start to see less standalone software products, and more and more technology-enabled products in sectors that have traditionally been non-technical. Mobile and web technology has the potential to radically increase efficiencies and improve user experiences. For example, Uber isn’t an app, it is a transportation company enabled by technology. We buy into this philosophy at Boxit as well, and that’s why we offer a seamless online ordering, billing, and box management process for our customers. We’re providing a great technology experience in self-storage, which traditionally has very little tech.

What would your advice be for startup women entrepreneurs?

The hardest part of doing a startup is managing your own psychology. You will doubt yourself again and again. Take time to surround yourself with other entrepreneurs – men and women. Get plugged into communities for female entrepreneurs such as SheEO, Fabulous Fempreneurship, Women In Biz, Secret Birds, Female Entrepreneur Association, or Company of Women.

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