How to Think Different, Challenge Assumptions and See New Ideas

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At our recent HowTo Conference, speakers shared their experiences with going against the grain to build their businesses.

By Vanessa Mason (Contributing Writer, Women 2.0)

When Apple and Steve Jobs told the world “Think Different,” they must have had Ruzwana Bashir and Tracy Sun in mind. Bashir and Sun kicked off the first panel for the Women 2.0 HowTo Conference, which was moderated by our CEO Shaherose Charania.

Ruzwana Bashir is CEO of Peek, which helps travelers find and book unique experiences. She came up with the idea after she spent countless hours researching and planning activities for a trip to Istanbul, only to have to call to confirm all of her plans in broken Turkish no less. Tracy Sun is co-founder of Poshmark, a mobile marketplace to sell things from your closet. She came up with the idea when making her cross-country move from New York to San Francisco and had to deal with the dreaded leftover boxes of clothing that she didn’t need.

Check out their tips below to spark new ideas and creativity and shake up multibillion dollar industries.

How to Know if You Have a Disruptive Company

Describe what the world would look like without it. For Sun, a world without Poshmark would be a world with a lot less social connection, delight and engagement without the ability of her passionate users to connect in deep and meaningful ways. Sun was a creative troublemaker since childhood, always challenging the rules and hearing that the questions she asked were not the right ones in school. Startups were a way for her to focus this energy in a way that matters.

Bashir sees how lives and revenues of the small business owners she serves with her scheduling and administrative software are transformed, leaving them more time focus on offering the services they love while increasing their revenue. Having been excited and intrigued about mobile apps and startups for years, she ignored advice to seek more industry-specific experience and jumped into startups during business school. After all, Bashir noted that Nobel Prize winners often make their award-winning discoveries in areas adjacent to their primary field, so why shouldn’t she do the same?

How to Challenge Assumptions

Ignore the naysayers and fake it until you make it. Bashir strongly believes in the power of a good team to get through the rollercoaster of starting a new business. Women especially need to overcome any lack of confidence and insecurity about missing skills by developing plans and strategies to compensate. She noted that investors only really care about your plan and your ability to attract talent that will complement your skills.

While every founder needs to find people who believe in what you are doing and your ability to do it, Sun noted that sometimes your worst enemy is yourself. Founders need to commit to themselves and not allow their internal insecurities get the best of them when hearing all the negativity that comes with pursuing new ideas. To overcome these boundaries, she called upon the imagery of ducks on the water to respond in situations where confidence is shaken: Calm on the surface, and furiously swimming underneath.

How to See New Ideas

Change your reality and try it. Sun played the Nike card and told everyone “Just do it,” adding that it’s best to fail fast and fail often. When looking back at her own pathway to her startup, she wished she could have enjoyed the whole journey, both the highs and the lows. Living through insecurity and doubt has made it easier to cope over time as she has learned from past experience that the fear will pass.

Bashir wished that she had started earlier rather than seeking more experience and following the assumption that certain boxes needed to be checked. Startups teach you how to build culture and hire the right people, experience that can not be acquired through other more traditional roles.

More From These Speakers

How will you start to think different?

Photo by Elvina Beck.


Vanessa Mason (@vanessamason) is the eHealth senior manager at ZeroDivide where she advises on the design, development and adoption of digital health for the underserved. Vanessa also consults on global health and technology development and adoption. She earned her BA from Yale University and her MPH from Columbia University.