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Women in Business: Q&A with Kate Endress, Co-Founder of DITTO

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Kate Endress is an athlete turned investor turned e-commerce entrepreneur. After graduating from Stanford Business School in 2011, Kate cofounded DITTO.com, an ecommerce site selling designer sunglasses and eyewear which features cutting edge new video "try-on" technology.

How has your life experience made you the leader you are today?
I was a highly recruited high school women's basketball player until I suffered a serious stress fracture on my vertebrae during my junior year. I could see my dream of becoming an All-American slipping away as major universities lost interest in me due to the injury. I endured countless hours of strenuous physical therapy, but the injury forced me to sit out during the most important recruiting season, and I lost the interest of hundreds of top schools. Luckily, I had garnered enough attention prior to the injury to attract the interest of a few regional schools, and I signed a letter of intent with Ball State University. Instead of focusing on an opportunity lost, I decided to be the driving force in building a stronger women's basketball program at Ball State. I was the first three-year captain in the program's history and, despite playing at a mid-major university, I was still able to garner All-American status, was named the Academic All-American Player of the Year, and was drafted by the WNBA.

My experience as a leader on the court gave me the confidence to be one in the business world. I decided to start a company because I love working closely with a group of talented, hard-working people to achieve something against the odds like having an undefeated season or building a virtual try-on technology that others said couldn't be done.

I openly aspire to be a great leader. I have always been naturally influential. Part of the reason is because I'm 6' tall, and the other reason is because my parents taught my two sisters and me to be strong, independent, confident women who can articulate thoughts with conviction and "thrive in a man's world" as my Dad would say. But simply having leadership traits does not make a great leader. To me, greatness is about being competent and hard working enough to be respected, passionate enough to inspire our team, our vendors, and our customers, and smart enough to build a team of people that is even smarter. The last three years that I've been working on DITTO have been an incredible learning opportunity for me and the road to greatness is still ahead. But I'm motivated to keep striving. I love reading books about great leaders and seek out advice and feedback of how I can be better. I hope I look back in a few years and smile knowing I've led DITTO with purpose and passion.

How did your previous employment experience aided your position at DITTO?
After my basketball career ended, I spent four years working on Wall Street and in private equity. I remember one day watching a coworker excitedly zip through a financial model for a potential investment and remember thinking "Wow, I just don't feel like that about this work". I became jaded that we did more financial engineering than true value creation, and I was craving soul-satisfying work that involved getting my hands dirty and building something valuable. I decided I needed to be a hands-on operator and build a product I believed in. Even though I could be making a whole heck of a lot more money with less risk in finance, I have never looked back once.

How do you maintain a work/life balance?
I am not a fan of the term "work/life balance" and the discussion of "having it all". I am a fan of talking honestly and openly about trade-offs that make sense for your specific family and situation. Life (like startups) is all about prioritizing. I spent time each day reflecting about what is really important and I prioritize those items relentlessly. Some days it's working on a new product feature. Other days it's spending quality time with my husband.

What have the highlights and challenges been during your tenure at DITTO?
The best moments for me are talking to customers who say "Wow, your virtual try-on technology was like nothing I've ever seen before and it solved a real problem for me." That knowledge that you and your team have built something with true value to someone is absolute bliss. The worst moments have been learning the patience associated with building real technology and being sued by two patent trolls. It's definitely been a wild ride but I've learned to love the fact that I'm never bored.

What advice can you offer women seeking to start their own business, particularly in ecommerce?
I have dozens of friends who talk to me about their passions but don't seem willing to take the necessary steps to make it happen. My advice is to stop talking and starting acting. Start small if you have to by taking a night class, selling things on Etsy, doing weekend work, etc. But success only comes to those to are action-oriented. My key advice: take active steps to improve your situation. You'll only regret what you didn't have the courage to attempt.

What do you think is the biggest issue for women in the workplace?
Confidence! In my opinion, women tend to be more self-conscious partially because physical looks are more important and partially because there is a deeper need to be liked.
I noticed that many of the incredibly impressive women in my Stanford business school class even speak with an upward inflection at the end of their sentences giving their statements less uumph and giving off the impression they were unsure or asking a question. I always smile when I see a woman speak articulately and with conviction, confidently ask for raises and promotions, and raise her hand to run a project or lead a team because she knows she's the best person for the job.

What are your thoughts on Sheryl Sandberg's Lean In book and movement?
I'm a fan of Sheryl Sandberg and love the discussion her book has reignited. She's inspiring women to be strong and courageous and many of her stories resonate with me directly. That said, I do believe that it's unrealistic for every female to have an extremely helpful spouse and the financial flexibility to have around the clock daycare when needed. I'd love for companies to take steps to fundamentally change the structure of the workplace to give better options to working mothers. I hope as DITTO scales, we can be a model for a company that can recruit elite female talent and offer flexible structures like 3 and 4 day working options for mothers. You can watch an interview I did with USAToday on Lean In here.

How has mentorship made a difference in your professional and personal life?
I don't love the idea of 'seeking a mentor.' I like getting support from authentic, naturally formed relationships with friends, family and investors. I have a few female friends in particular who are also starting their own businesses so I have a network of people around me when I need to vent, swap stories or ask for an opinion.

Which other female leaders do you admire and why?
I admire my sole female investor, Sonja Hoel Perkins, who worked her way up to the top of her venture capital firm without a female peer group and then turned around to start Broadway Angels, to back women in information technology. I admire Anne Bonaparte, CEO of Xora, and Jessica Herrin, CEO of Stella & Dot, for being two great examples of women who prioritize their life very well. I admire Marissa Meyer, CEO of Yahoo!, for being strong enough to make tough, unpopular calls like reducing the broken remote working program which she believed was not in the best interest of the company.

What are your hopes for the future of DITTO?
We hope we can revolution the way people shop online by visually showing them how products fit before they buy them. We started with eyewear because we had each had
bad experiences buying glasses in stores driven by limited style choices, an awkward try-on experience (when you take off your glasses you can't see yourself in the mirror), expensive products, and a 2 week wait to get our glasses. We knew we could build a better experience by giving people a wider selection of top designer styles at all price points and building technology that shows you how the products actually fit on your unique face in 3D. Long term, I hope we can move into apparel, but for now we are very happy helping customers people find glasses that fit them perfectly.