Going Against the Flow: Craig Newmark and Allyson Kapin

Craig Newmark is the founder of Craigslist and Craigconnects. Allyson Kapin has founded Women Who Tech and Rad Campaign. They are committed to leveraging technology for philanthropy and social good. Together, they held the first-ever Women Startup Challenge Pitch Competition, and their first crowdfunding campaign raised $315,000 for 88 women-led startups.

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Craig Newmark

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Allyson Kapin

Q: What does entrepreneurship mean to you, and what underlying characteristics do you find common in successful entrepreneurs?

Craig: To me, it's about running a business in a way that takes higher risks than most, serious customer service, and following through with customer concerns. The listening and follow-through parts are a common trait. A downside of this approach is that bad actors might try to game you by faking feedback that would waste a lot of resources. Fortunately, in the first several years, I had no resources to waste.

Allyson: Entrepreneurship means launching and running a business. To run a business you need to be driven, have a strong vision but also be flexible enough to adapt and iterate on your product. You also need to have a strong and supportive team who are empowered to lead in different areas you don't have the capacity or skill to lead.

Q: What are you most proud of in your professional career? If you could do something over in life, what would that be?

Craig: I guess it was sticking with Sunday School values like knowing when enough is enough. Not noble or altruistic, but that meant I turned down huge money when offered, three times.

I'd only do one thing differently. When sticking my neck out far to help people, I should've already prepared to broadly explain what happened. I have to be vague here because the situation is still sensitive.

Allyson: I'm really proud of building our web agency Rad Campaign, which was born out of our desire to empower people across the world to use the Internet to create social change. I'm also very proud of Women Who Tech and the Women Startup Challenge that I launched and have partnered with Craig on to showcase women-led startups and shake up an economy that has made it exceedingly difficult for women entrepreneurs to access capital.

3. Tell us about an instance when you went against the flow to realize your goal.

Craig: Monetizing Craigslist very little and turning down huge money is very contrary to the usual Silicon Valley approach.

Allyson: This is the story of my life. I never would have cofounded a web agency or launched nonprofits like Women Who Tech by going with the flow. You've got to take chances!

Q: Why do we need more female entrepreneurs?

Craig: I feel that we should treat people like we want to be treated. Sometimes, fairness means helping out people in the direction of a new normal, in this case, gender equity in business. Follow through means helping out in real ways, like with the Womens' Startup Challenge, Women Who Tech, Girls Who Code, Black Girls Code, and more.

Allyson: Diversity (whether it be gender, ethnicity, age, etc.) is incredibly important to the startup world because it leads to better products and innovation. Currently, only seven percent of investor money goes to women. If we truly want to innovate and create the best products for people in this world, we need to radically change how we invest. And that is what we are hoping to ignite through the Women Startup Challenge.

Q: What advice would you give your 22 year old self?

Craig: You're responsible for your own career. You have to create your own narrative. Your boss can help, but that's secondary to what you should be doing.

Allyson: Just do it. You spend the majority of your adult life working, so you may as well do something you are passionate about.

Follow Craig Newmark and Allyson Kapin on twitter at @CraigNewmark and @WomenWhoTech, and check out the other interviews in Going Against the Flow series at http://www.huffingtonpost.com/charu-sharma/ and join our movement to empower 1 million female entrepreneurs at goagainsttheflow.com.