Ilya Lyashevsky – Co-founder of WeShelter

Think of those aspects of the product that aren’t where they should be, and figure out how to get them there.

Ilya is getting his doctorate in Cognitive Studies at Columbia Teachers College. He also writes fiction. Prior to co-founding WeShelter he was Director of Mobile Development at Broadcastr and SPUN. He also co-founded Good To Know, Inc. which created Storied, an educational suite of software aimed at helping students learn vocabulary by reading original stories. He headed mobile development at Electric Literature, and created mobile apps for such organizations as Human Rights Watch and the Kenyon Review. Ilya received a BS and MS in computer science, as well as a minor in creative writing, from Stanford University.

Where did the idea for WeShelter come from?

The initial inspiration was, unfortunately, the large number of homeless people we would see on the streets of New York. Each time we saw someone we’d feel the impulse to help, but it was unclear how best to do it, and too often we ended up doing nothing as a result. We realized that thousands of other people must be having the same experience: feeling the impulse to help but not acting on it because of a sense that there is nothing they can do. At least nothing sufficiently simple, cost-effective, and meaningful. It seemed like a problem that mobile technology was ideally suited to help solve, and since we were all working in the space, we set out to solve it.

What does your typical day look like and how do you make it productive?

All of us work on WeShelter on a volunteer basis, and have other full-time occupations. In my case, the full-time gig is a PhD in cognitive psychology at Columbia Teachers College. One of the benefits of being in grad school is a relatively flexible schedule, and the opportunity to work from home several days a week. I tend to break up my day by projects, and like to start with a couple of hours spent writing. I may then move on to academic work, and finish the day with WeShelter tasks. However, the reality is that often I will end up doing WeShelter work throughout the day, particularly communicating with partners, sponsors, volunteers, and cofounders. With regard to productivity, I personally feel like I’m always behind, so I may not be the best model. But I do find that planning ahead, giving yourself enough runway for bigger tasks, splitting them up and pacing yourself, are important for getting things done well and on time.

How do you bring ideas to life?

It often begins with a sense of dissatisfaction: something isn’t quite right. Then there’s a period of gestation where you think about what it is that’s unsatisfactory, and how you might go about setting it right. Then an idea might present itself, which may have the kernel of a solution, at which point discussion, further reflection, and iteration, with or without prototyping, may take place. I will often bring an idea to my cofounders, and we’ll discuss it, and may determine that it’s premature or that a slightly different approach might work better. I find it helpful to be regularly reminded that something which seems brilliant and essential to you may be seen very differently by someone else on the team.

What’s one trend that really excites you?

There are a lot of really exciting trends right now: VR and AR, AI and brain research, neural feedback technology, renewable energy, and of course an explosion of social entrepreneurship initiatives, accelerators, and even social good venture funding. The trend that I personally am perhaps most excited by is a general movement toward greater self-awareness, on an individual, organizational, and societal level, which promises a more equitable, just and peaceful future. Technology has been a great driver of this trend, as it has facilitated communication, self-expression, the distribution of narrative art forms, as well as the exposure of injustices and abuses. And we see WeShelter as contributing to this movement, by allowing people to act on a compassionate impulse that previously often had to be denied and suppressed.

What is one habit of yours that makes you more productive as an entrepreneur?

In the past I had been more prone to procrastination, which creates the risk of being rushed when you finally get to the thing you had been putting off. Over the years, I have gotten better at starting tasks earlier — it is usually starting that’s most difficult and daunting, and once you start you find that it’s not nearly as bad as you had feared — so that I usually have enough time to get them done.

What was the worst job you ever had and what did you learn from it?

I’d say it was selling Cutco knives the summer before college. The knives, incidentally, are excellent, but I was no good as a salesman. For a long time I took that to be the main lesson of the experience, but eventually I learned that I had no great trouble with sales if certain conditions were met: I had to believe in the quality of what I was selling, but I also had to care about the purpose of the enterprise, as otherwise I could not bring myself to undertake the often discouraging task of pitching and making cold calls.

If you were to start again, what would you do differently?

With regard to WeShelter, I would have started the process of getting our 501c3 status earlier, as it takes a while, and is helpful to have. I would also pay more attention to organizational processes, as these become incredibly important once the organization begins to expand even slightly, and effective management and delegation become crucial.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Think of those aspects of the product that aren’t where they should be, and figure out how to get them there.

What is one strategy that has helped you grow your business? Please explain how.

We’re a non-profit, and our business model hinges on acquiring sponsorships. One key thing we had to do was precisely identify the types of organizations that would be interested in coming on board as sponsors, which meant considering a number of factors including company size, whether their business aligned with our mission, and was consumer-oriented. It also helped if the company was tech-driven, was focused on and based in NYC, and already had shown some commitment to social responsibility. We’ve been a lot more successful in our sponsor search with organizations that matched this “ideal” criteria.

What is one failure you had as an entrepreneur, and how did you overcome it?

A few years back I had started a business with a friend, but it turned out we had very different ideas for the company and weren’t compatible as business partners. We eventually went our separate ways, but the process was needlessly acrimonious, and the result was the end of the business and the friendship. Nevertheless, the experience taught me a good deal, and one of the main takeaways was to be very careful whom you go into business with.

What is one business idea that you’re willing to give away to our readers?

This idea will likely be made obsolete by the advent of self-driving cars, but I’d love for someone to develop a sensor that bikers and even pedestrians might wear, while a companion sensor could be installed in cars to help avoid accidents, with insurance companies offering incentives for drivers to undertake the installation.

What is the best $100 you recently spent? What and why?

A HEX convertible backpack. My old laptop bag was falling apart, and I was looking for something stylish but also sturdy and that I could both strap on my back and carry in one hand. The HEX Infinity convertible backpack did the trick. Aside from digging the look, I find that I also appreciate the way it smells: like an old canvas sofa. It’s oddly comforting.

What software and web services do you use? What do you love about them?

Everyone uses it now, and we too have switched to Slack for communication. It’s a great way for the team to stay connected. Trello for project management: it’s got a simple interface and keeps you up to date on task progress. Bitbucket for source control, it’s free, powerful, and reliable. AWS for site hosting.

What is the one book that you recommend our community should read and why?

This is not a business or technology book, but I would recommend Saul Bellow’s Henderson the Rain King. It is of course Bellow himself who is the king–of explaining humanity to itself. Humor, adventure, insight, truth. Henderson has it all, and more of it per page than just about anything else.

What people have influenced your thinking and might be of interest to others?

BJ Fogg: he was a professor of mine at Stanford and does really cool work that looks at what makes technology successful. Rose Broome, the founder of Handup, who is an inspiring tech leader and innovator, and all around lovely person. Andy Hunter, for whom I worked at a couple of startups, and who now heads Catapult Publishing. Andy has the rare combination of deep intelligence, refined artistic taste, business acumen and abiding decency. All three have offered valuable input on the WeShelter project.


WeShelter on Twitter: @WeShelter
Ilya Iyashevsky on Twitter: @ilyashev
Ilya Iyashevsky on LinkedIn: