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by Leslie Bradshaw


How Sassy Magazine Inspired a Future Female TechStar

[Originally posted on Forbes.]

< So far at More Seats, we’ve talked about the process of changing the ratio with Emily Gannett and what changing the ratio from within the political class looks like with Mindy Finn. We’ve also talked about bridging the gap between paraprofessional and partner tracks with Karen Vander Linde and breaking through the thick layer of men at the top with Cindy Gallop. More recently, we learned from Nisha Chittal why “ambition is not a dirty word” for the next generation of women and what the impact of a strong Russian grandmother can have on one of today’s largest technology brands from Ekaterina Walter. Another key piece of advice to gaining more seats resides in taking risks and “not being afraid of beta” as Cory Haik implored us yesterday.

Today, we take the issue of female-founded start-ups head on with Nestio’s CEO and Co-Founder, Caren Maio. On the heels of the much tweeted about and commented on article by Mark Suster (“Why Aren’t There More Female Entrepreneurs?”), Caren’s background and approach provide a window on the solution to the imbalance.

She also grew up in the Sassy generation (something we share), which hopefully means there are more of her, more of us, rising in the ranks and leveraging our sass in the form of founding companies. Boom.

Background Information:

Name: Caren Maio

Hometown: Monmouth County, NJ

Current City: New York, NY

Employer & Job Title: CEO, Co-Founder of Nestio

Educational Background: BA from New York University – Brand Building, Publishing

Previous Work Experience: Sales/Business Development at The Wall Street Journal, Nike

LB: Women lead only 8% of tech startups. As someone defying these statistics with Nestio, what do you see as the main obstacles for women in this field? What strategies or efforts can you offer to women interested in pursuing this path?

CM: As a newcomer in this industry, I’ve been amazed at how inviting and welcoming the community has been. The support, comfort, and camaraderie that I’ve received from other women in the industry has been nothing short of incredible, and I have every intention of paying it forward. I encourage other women to do the same and continue providing the necessary support and mentorship to raise that number!

LB: Agreed. Next to female founders, female mentorship is arguably another one of the tougher things to find in the technology industry. How have you approached this?

CM: During my time at TechStars, I was lucky enough to meet three amazing women – Joanne Wilson, Beth Ferreira and Alexandra Wilson. They’re complete assets to our team, and their guidance has been invaluable – from product feedback to general business advice. They’re some of the smartest, most hard-working women I know, I trust their advice implicitly, and I couldn’t be luckier to have them in my corner.

LB: What three pieces of advice would you offer young women looking to start their own company?

1) Talk about your idea to as many people as you can. Solicit as much feedback as possible to determine if there really is a market/need for your solution. You may realize that there’s not much of a demand for what you want to do. Or you might find that others share the same need you do and that you’re onto something!

2) Take your time building the founding team. Ideally, your co-founders are people you know well and/or have worked with in the past. If that’s not the case, don’t rush into anything. Make sure you spend enough time looking for the right combination of skill sets, expertise, and personality. The last thing you want to do is attach yourself to people who aren’t on the same page as you.

3) Don’t be afraid to show users your product before it’s ready. The fact is, it will never be “ready.” You can spend months working on your product, revising and perfecting it, but you’ll learn the most once you put it out into the world and watch real people use it for the first time.

LB: As you mentioned, you’ve been fortunate to be one of the chosen ones to be a part TechStars. Share with us, if you don’t mind, the most valuable lesson / advice you received from the experience.

CM: Test your assumptions early and often. Our team came into TechStars with an overbuilt product that we thought people wanted. After the first couple of weeks of the program, we realized our initial assumptions were wrong. TechStars gave us the ability to kick the tires quickly and fail safely. They also supported us with the resources we needed to make new assumptions, test them, and pursue a solution that we knew users wanted.

LB: Did you have any female role models / mentors when growing up?

CM: Growing up, I was a shameless and avid reader of Sassy magazine. Sassy had a ton of heart. It spoke openly about topics that were once considered taboo, and had an uncanny ability to do it in a voice that was smart, thoughtful, and often, refreshingly frank. I think that was largely due to the influence of its editor-in-chief, Jane Pratt – she knew what her demographic wanted, she was her demographic. She spoke to her readers openly and honestly – almost like a knowledgeable best friend or an older sister you looked up to. I’ve always appreciated that kind of transparency, and try to keep it top-of-mind today as we build Nestio and create an open line of communication with our users.

LB: What drives you? What motivates you to get out of bed, stay late and / or work on the weekends?

CM: I love that we’re solving a real pain point for our users. Looking for a new place to live is an incredibly stressful and time-consuming process, and my co-founders and I were individually frustrated by it for years. We know the pain points that go along with finding an apartment, and set out to make that process easier and more manageable. I remember someone once told me, “Be a vicodin, not a vitamin.”  I’d like to think that nothing about our product is just “nice-to-have.” Every feature was borne out of an actual problem that someone on our team has experienced. We’re using that as motivation and inspiration to improve the experience for all apartment renters, and there’s no better feeling than receiving that sort of validation from our users, that we’re in fact making the process easier.

LB: How would you describe your approach to the world?

CM: I’m a big proponent of self-awareness and self-improvement. I think it’s really important to push yourself as much and as often as possible. When I was growing up, I played a lot of tennis and always tried to play with people I thought were way better than I was. If I needed to work on my serve, I played the person with the best serve I knew. I remember I got my ass kicked a lot, and there’s nothing fun about that, but I’ll tell what – after a few months my game improved substantially.  I try to take a very similar approach today as well. I know my strengths, but more importantly, I know my weaknesses. I try to surround myself with people – co-founders, new hires, advisers, etc. who exhibit strength where I know I’m weak. I’m not afraid to admit that I know what I don’t know, and hopefully in doing so, will be able to build the strongest team possible and bring complementary skill sets together.

LB: What, if any, distinct traits have you seen fellow female coworkers bring to the workplace? Do you yourself exhibit them? (Why or why not?)

CM: I found that women are amazing multi-taskers. Speaking for myself, I’ve actually found it to be a bit of an addiction. One of my biggest pet peeves is inefficiency. If I’m not doing at least a few different things at once, I feel like I’m wasting time and not being as productive as I could be. It’s how my brain works anyway, and I often have to bounce around between several different tasks in any given day. It’s an added bonus that I happen to actually enjoy it!

LB: Did you make assumptions when you first started your career that subsequently proved to be wrong? What sort of insights did you gain?

CM: For a long time, I was my own worst critic. I placed a ton of emphasis on perfection, and I was hard on myself when I felt like I didn’t meet my own expectations. I quickly learned that making mistakes was not only an okay thing to do, it was a total necessity. There’s no better way to learn and grow from your experiences, and I started giving myself the leeway to be wrong.

LB: What do you like most about what you do?

CM: We have an incredibly agile team, and I’m really proud of that. Every day, we set out to improve upon an experience where we have all been burned before. We know the problem we’re solving, and we’re really passionate about our solution. We communicate constantly, test things quickly, and continue to validate and/or challenge our own assumptions based on the features, feedback, and comments our users provide. I really enjoy working that way, and I’m joined by a team that I couldn’t admire more…what’s not to love?

LB: What’s the worst business advice you’ve ever received?

CM: “You can just as easily work on a start up part-time.” No, you can’t. The best thing my co-founders and I did was take a chance on ourselves and leave our jobs for the TechStars program. It gave us the ability to quickly test our assumptions, shift course, and embark on an entirely new journey with Nestio. I couldn’t be happier with our decision.

LB: According to an article with NYULocal (http://nyulocal.com/city/2011/04/11/nyu-grad-makes-apartment-hunting-easy-with-nestio/) you mentor NYU students through the apartment hunting process. What have you learned from this experience? And, what do you see as the main challenges prospective hunters face (both women and men)?

CM: New York is a really unique market (when it comes to real estate), and the learning curve can be steep. I went to NYU, and I remember how stressful and frustrating it was to look for an apartment amidst all of the other responsibilities I had as a student. I wanted to lighten the learning curve, and help other people avoid the same mistakes I made when searching for my first couple apartments. Whenever I’m helping someone with their apartment hunt, my first question is always the same: What’s most important to you? Everyone has a checklist of criteria for their perfect home – such as location, amenities, and pricing, and I encourage apartment hunters to prioritize that list. It’s usually impossible to satisfy every single item on your list, but if you can land a place with your top two or three priorities, it’s a win.

LB: What’s up next for Nestio? What are your upcoming expectations and goals for the company?

CM: Right now, it’s all about product development and user testing. Over the past several months, we’ve built a foundation of features that we’re really happy with, and we’re looking forward to building on top of that to make the process even easier. For us, it all starts and ends with our users, and our primary goal is to make sure that whatever we do adds value and improves their experience. We’re thrilled with the progress we’ve made, and we’re really excited about what lies ahead in our roadmap.

To keep in touch with Caren, follow her @carenmaio

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