Tindley Gilbert Founds a Company While Living Overseas... with 3 Kids

WHO SHE IS: Tindley Whipple Gilbert, Founder & CEO, Diggity

Success Story: Concepted, designed and launched a new tool for searching across all of one’s social media just after having my third baby and while living as an expat overseas.

Work Schedule: Currently living in Dubai where the work week is Sunday – Thursday. I work school hours and all hours of the night to connect with my team in Seattle.

Kids: One daughter (5 – going on 25!) and two sons (1 and 3)

Sanity Vice: Dance parties with my kids, keeping them on a good nap and sleep schedule, lots of coffee, and a bit of “me-time” throughout the week that helps me recharge and think more clearly.

How she got here…

MB: Walk us through how you got to this point in your career.
TWG: For anyone who knew me growing up, I think living as an expat in the Middle East would be the LAST place they would picture me. I was the girl that grew up in Chicago, went to Northwestern University (close to home) as an undergrad, worked in Chicago afterwards and then went back to Kellogg Graduate School of Management (Northwestern) for my MBA. I absolutely loved Chicago and never saw myself leaving.

After Northwestern, I was blessed to work at McKinsey & Company, where I was thrown into solving business problems on an hourly basis. It was another life-changing experience and an important step along my path toward entrepreneurship, as I tried to gain skills that would help me run my own business one day. I was exposed to so many different businesses, business practices, leadership styles, and ways of thinking.

Post business school I took a marketing role at Pfizer, but left for a smaller firm after having my first child because I felt I could have more autonomy over my schedule. This role further solidified for me an important lesson: even if you have autonomy at work and are able to set some of the schedules, that doesn’t mean you have a lighter workload. Yes, some days I could work from home if my child was sick, but I was still putting in 16 hour days. Or, I could try to make the 5pm train to be home for dinner, but I was still online from 7:30pm-1am.

Tindley Gilbert with her three children in Dubai. (Oct. 2012)

Tindley Gilbert with her three children in Dubai (10/12).

After moving to Dubai for my husband’s job in 2009, I had multiple situations where I wanted to take information from Facebook (including the “rich content” of comments, likes, etc.) and be able to search, organize, save and share it. Trips to Egypt. The first time my son walked. The first words my daughter said. All of this was on Facebook and at the time, it was difficult to find. Also, as a busy mom, I wanted to make this information VERY easy to find. After doing a lot of research, my husband and I decided that this was the next problem I was meant to solve.

So, we found a development team and started working on Diggity in earnest in the summer of 2012. The road has been great but it is A LOT of hard work. Given the time difference, my husband’s intense travel schedule, and living overseas, it makes it difficult to juggle it all. But, I am learning each day and continuing to evolve as an entrepreneur, working mother, wife and person!

How she does it: Diggity, Flexibility at the Helm, and Advice for other Moms

MB: You live in Dubai. What’s the scene like for working mothers there?
TWG: This is challenging because given the many cultures and nationalities living in Dubai, it’s hard to truly know every working mother’s experience. Some mothers are working here but in order to do so, have had to leave their children in their home countries. I can’t imagine how difficult that is. On the other end of the spectrum are women who have moved to Dubai with their families. Some may have made a choice to leave their previous careers to move overseas as a result of their spouse’s career, and as a result may not be working here. However, I have many friends here who are working mothers, either working as entrepreneurs – like me – or for larger organizations in many industries, including consumer product goods, education, finance and hotel management, to name a few. There are many benefits of Dubai that make it very possible to be a working mother.

MB: Tell us about Diggity
TWG: Diggity is a free, personalized search bar for your digital life. It’s no stretch to say that these days, we live our lives online. We share, post, like and tweet our biggest and smallest moments with each other – momentous occasions like weddings, births, trips, even dinners and family get-togethers in Grandma’s backyard. But what happens when you want to rediscover these moments after a few months, or even a year or two? And even if you did find everything, what could you do with it? That’s exactly why I created Diggity, which enables you to search, organize, save and share your social media experiences and memories. You can save information to Shoeboxes to review at any time, create an electronic album to share with friends or family, and soon, turn everything into printed products. Most importantly, we’ve focused on creating an easy-to-use user interface that should make this information quickly and easily available to you.

MB: With three kids and an ex-pat life, why did you decide that this was the best time to launch a business?
TWG: In some ways this is the BEST time to do this. First, I know my target market because I AM my target market. Every day, something comes up in my own life (“Gosh, I wish I had saved that article to a Shoebox so I could go back and read it later”) and so I feel like I know what others may be looking for in a product like Diggity. Second, the time zone difference does allow me to try to balance time with kids and working, which was what I always wanted. It is true that you can’t have it all at the same time, though, so I do see that I am usually taking time away from myself. Third, being an expat has given me the opportunity to meet people from all over the world and better understand where they are coming from and issues they face, which also helps me build Diggity to meet our users’ needs.

MB: Do you think that being at the helm provides you the kind of flexibility you need?
TWG: Yes, without question. That is one of the greatest benefits. It was one of the main reasons I knew I wanted to be the leader of an organization. But, you also set the tone for the entire organization, so it comes with a great responsibility. As I always say, I wouldn’t ask any team member to do anything (or work at a time) that I wouldn’t also do. I also think that although you have more flexibility, you are likely working longer hours. I tell people that whether or not I’m “working,” I am always working. When I’m in the car, in the store, at a function—I’m always thinking about work. To help me, I carry post-it notes with me everywhere to capture all of my thoughts.

MB: One of the hardest parts about running a business is knowing when to shut it off. How do you manage this?
TWG: This is the hardest part for me. I have 3 kids under 5, so the fact that I have conference calls, strategic plans, and marketing meetings to contend with doesn’t resonate with them! As a result, I’ve made it a priority to learn “how” to shut it off. Otherwise, I’m not living up to my own desire to balance work and motherhood. Being able to “shut it off” is also complicated by the 12 hour time difference, because I could technically work all night, as that’s when my team is working. I think you should always strive to achieve work/life balance at all times but I recognize that it ebbs and flows. Here is how I try to achieve the best work/life balance:

Understand my business: Some weeks, my work/life balance will not be great. Maybe we’re working on a new feature or in the midst of financing, but then when I recognize an opportunity to take a break, I try to take the time to relax.
Listen and respect my body’s messages: Sometimes, I just have to fall asleep at 8pm after my kids go down and I know that any work I would have tried to do wouldn’t have been fruitful.
Pre-plan down time: I have finally figured out that certain nights of the week, I should take time off. I know it’s my team’s weekend (Saturday morning) and it’s my time to catch up, if I need to. If I don’t need to catch up, then I allow myself the opportunity to relax. I either go on a date with my husband, have a girls’ night out, watch TV or read. This is important refueling time. I find if I schedule it and have it planned, then it’s easier to follow through on taking a break and I’m more energized when I get back into the thick of work.

MB: What advice do you live by as a working mom
TWG: There are so many idioms, sayings and words of advice that have guided me in my career. Here are some of mine:

Know thyself. If you are meant to have a job, outside that of being a mom(!), that’s great! Don’t feel like you have to make excuses for yourself and don’t beat yourself up. There are so many lessons that your children can learn from your experience. You can involve them in your work as well—it’s wonderful for children to see their moms in different settings.
Make sure to have someone with whom you can communicate your successes and fears. We all need someone to talk with. Your partner. Your friend. Your parents. A stranger.
Balance in all things. It’s not healthy to either a) work 100% of the time or b) be with your kids 100% of the time. It’s okay to find a happy balance that works for you, your kids and your family and again, to not have to make excuses about it.
Find time for yourself. Whatever it may be.
Be kind to yourself. At the end of the day, tell yourself, “I tried my best today and tomorrow I’ll try harder.” This is especially helpful after a tough day with one of your kids. You may not have handled a situation as you would have liked, but It’s important to be “kind” to yourself and know you will try differently tomorrow.
It’s good for your kids to know that others (outside from their parents) love them. Someone told me this right after I had my first child and knew I needed to hire a nanny. It’s okay to seek out people to help you while you’re working (nanny, daycare, etc). And, it’s okay if they spend time with your kids. Your kids will learn that they are loved by many different people.
Find ways to outsource aspects of your life. Birthday parties are a great example. It doesn’t have to be expensive, but there are ways to again ask others for help.
Know what you’re good at. This is good for business, and important for healthy relationships. If you’re good at doing the dishes, then do the dishes and let your partner do something else around the house that they are good at. But (and here’s the important part!), don’t get angry when your partner doesn’t do the dishes. You are both working with your strengths.
Hug your kids at least 10 times a day. This is something they’ll always remember.