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What This Founder Learned at a Farmstand Helped Her Bra Startup Heidi Zak, the founder and CEO of lingerie company ThirdLove, shares lessons learned.

By Nina Zipkin

entrepreneur daily
ThirdLove

Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

For many women, shopping for the right bra is something of an ordeal. You have to get measured by a total stranger, the bra may only last about a year and the offerings that are available can be pretty expensive, with an average garment retailing for about $100 or more.

Fed up with an exhausting and inefficient process and certain that others felt the same, in 2013, Heidi Zak launched ThirdLove, a San Francisco-based lingerie company that aims to provide customers with bras that truly fit at an affordable price.

Related: A Bra Company That Uses Smartphones to Find the Right Fit Just Raised $8 Million

Zak, who worked as a senior marketing manager at Google before founding the company, differentiated ThirdLove from other lingerie startups by integrating technology and patenting an app to allow users to size themselves at home with just a few photos. Once a person is sized, they can shop for the bra they need. ThirdLove allows customers to try the garments before they purchase for 30 days. If it doesn't fit, then they can send it back for $2.99. The company also provides a glossary of fit concerns on the site for reference and live chats with ThirdLove stylists.

She also realized that standard sizes simply wouldn't work for every customer, so with head designer Ra'el Cohen, the company designed bras in half sizes. With that custom fit in mind, ThirdLove also has a 30-day trial period before purchase.

Since its launch over four years ago, the company has raised more than $13 million, expanded into underwear, as well as lounge and sleepwear and has more than 250,000 paying customers.

We caught up with Zak for our 20 Questions series to find out what motivates her and makes her tick.

1. How do you start your day?
I wake up usually around 6:00 am and try to get a quick workout in. I have two little kids. Before my second baby, I would go to a bootcamp or a cycling class but now I just tend to do cycling using Zwift. It's a cool new startup that allows you to use your own bike and work out with the TV. I also use Daily Burn, a platform for online fitness videos That way I can just work out from my basement. Working out is something that really energizes me and makes me feel much more focused and efficient. The days I don't work out, I feel it.

2. How do you end your day?
By putting my kids to bed. I have a 3 year old and a 7 month old. I'm away from them during the day, so for me, it's crucial to spend time with them.

What I love about that is that when you're with your kids you don't have to think about anything else. As the founder a company your mind is always racing, but I don't think about anything for a few hours while I spend time with them.

Related: The Top 10 American Cities for Working Parents

3. What's a book that changed your mind and why?
Siblings Without Rivalry by Adele Faber and Elaine Mazlish. It's all about how children relate to each other -- but some of it also can be brought into any relationship, even those at work. The book talks about not needing to be fair, meaning, each child does not need to get the exact same thing.

This lesson applies really well in the corporate environment, too. Every employee is unique and needs their own personal objectives and goals. If you're having any interpersonal issues, getting to the root of the issue at hand is important, so is being able think about things from different [points of view].

4.What's a book you always recommend and why?
One of the things that is super important in business is how to negotiate well. For me, it's something that I've had to learn along the way. One of the books I read at MIT is Getting to Yes by Bruce Patton, Roger Fisher and William Ury. I recommend it to everyone at our company to read.

Negotiating is a hard skill, but one that is necessary for almost every job function - and this book is a quick read about the basics. The key learning for me is that you must figure out what you can offer to the other side, and to do that, you must get to know them to understand their most important needs. It's not just transactional, it's personal.

5. What's a strategy to keep focused?
I check email once an hour or less. If I check it more, I lose focus. So, I set aside five or 10 minutes to check email and then spend the rest of the time thinking about what I need to be doing.

Related: 4 Great Non-Business Role Models for Entrepreneurs

6. When you were a kid what did you want to be when you grew up?
I wanted to be a broadcast journalist. I looked up to Katie Couric when she was at the Today Show. I think she was just really knowledgeable and came across as very friendly -- something about her that was really real, and I think I liked that about her.

7. What did you learn from the worst boss you ever had?
I haven't had a lot of really bad bosses. The one thing that I've noticed from having different types of bosses is that the best ones have a clearly articulated vision of what the team is working toward. You have to communicate it effectively and do it often. That's what I try to do; you can't say it too often.

8. Who has influenced you most when it comes to how you approach your work?
I think my dad is my biggest influence. He grew up on a small farm outside of Pittsburgh. Through a lot of hard work and by focusing on education, he has been really successful in business. I think it's true in life that when you work hard, things will work themselves out for you. That work ethic is also something that I look for when I'm hiring.

Related: 7 Elements of a Strong Work Ethic

9. What's a trip that changed you?
Five years ago, my husband and I climbed to Mt. Everest basecamp in Nepal. You get to 18,000 plus feet at base camp. It's important in two ways: I like to challenge myself generally and that trip pushed me to my limits. I had a little altitude sickness, but I made it thanks to the support of my husband and the other couple we were with. That's the other thing, surround yourself with people who are supportive that you trust.

10. What inspires you?
I think what inspires me the most are our customers. I specifically set aside time to read customer chats, reading the positive comments of course is awesome, but I also get a lot of value from the things that we can improve on. I read those conversations and get inspired to do things better, change things and develop products based on that feedback. That inspires me every day.

11. What was your first business idea and what did you do with it?
I had a more traditional career path before ThirdLove. But after moving out to Silicon Valley five years ago, I caught the entrepreneurial bug. I was impressed by the people I was meeting and ThirdLove was the first real business I started.

Related: Starting A Business? You Need These 3 Basics.

12. What was an early job that taught you something important or useful?
My first job was when I was 14, I grew up in western New York, and I worked at a farm stand. There are two things that I still use today from the job. One is how to make things look really beautiful. It was very much learning how to merchandise -- how do you make them look compelling for a customer that it going to walk in. The other thing was I learned how to think about the customer, what their needs were and how to sell to them effectively.

13. What's the best advice you ever took?
Get comfortable with being uncomfortable. When you start your own company you have to get used to learning how to do things that you don't know how to do. You also need to learn how to take risks and be okay with not knowing what the next stage is going to bring.

14. What's the worst piece of advice you ever got?
The worst advice that I've gotten is to not do something. There is never been a time that I have regretted going somewhere new. Most regrets come from not seizing an opportunity or not doing something. A lot more comes out of saying yes than saying no.

Related: Richard Branson: How to Spot an Opportunity

15. What's a productivity tip you swear by?
We use Hipchat at work. It's a great way to collaborate across teams and share files instead of email.

16. Is there an app or tool you use in to get things done or stay on track?
I live and die by my Google Calendar. I would be nothing without it.

17. What does work-life balance mean to you?
I don't think there is such a thing. Every day you choose something to prioritize, especially as a working mom. Sometimes I stay late to work or leave early to go to my daughter's preschool. Every once in awhile I squeeze in something for myself. You're always picking and choosing, and hopefully, it's balancing out over the week or month.

Related: In Defense of Work-Life Balance

18. How do you prevent burnout?

It goes back to exercise and being outdoors. In the winter that might be snowboarding or going on a trail run, or maybe surfing, being outside and getting away from technology. Those activities really energize me.

19. When you're faced with a creativity block, what's your strategy to get innovating?
Go outside. I think taking a walk and going out to look at some new scenery is the best way to reset.

20. What are you learning now?
Right now our business is growing very quickly, so I spend a good amount of time interviewing more senior people. The interview process is much longer for these hires, because it's important to find the people with the right skill set, cultural fit and leadership skills. For me, it's learning how to effectively handle those interviews. That's something I've been focused on recently.

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at Entrepreneur.com. She frequently covers leadership, media, tech, startups, culture and workplace trends.

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