By Joanne Wilson (Blogger & Angel Investor, Gotham Gal)
Heather and I did not start out on the best foot.

We were introduced by someone that I have the utmost respect for and would meet with anyone he introduced me to. Heather was coming to NYC and we had a date to meet. At the last minute, she wanted me to come meet her up at the Startl conference, which didn’t work for me.

Her company was chosen as one of the top 10 companies at the event and I told her she would be a lot better off staying there and making contacts then she would meeting with me. Heather happened to see my husband speak at the event and asked me if I could help her get 15 minutes of his time. Perhaps a total knee jerk reaction on my part for a variety of reasons, but that never sits well with me.

We never did meet when she was in NYC but I give Heather an A+ for effort because she continued to persevere until we had a conversation. I finally said yes because of the original introduction. Ends up, I am so blown away by Heather and her path that I can’t get her story out of my head. So there you have, it isn’t always about the first impression.

Heather Hiles

Heather was raised by a single mother and grew up in the Crenshaw area of Los Angeles. Her mother worked for the state of California and had herself transferred to Santa Barbara for Heather to go to High School. Didn’t thrill Heather but it was an incredible move on her Mom’s part. Heather had nothing to do but focus on her school work and in 10th grade starting playing basketball and by the end of her high school years she was All-American and recruited to play ball for USC.

She looked at USC and decided that she had no interest in basketball and opted to go to Berkeley instead. Heather was given a Pell Grant allowing her to leave her undergraduate education with no debt. While at Berkeley she worked with Ronnie Stevenson, a former Black Panther, who had a non-profit organization called Break the Cycle. The organization now works on breaking the cycle of teenage dating violence but back then they would help kids who were already at risk focusing on kids falling behind in school from kindergarten to third grade. Those parents literally had no idea how to help their kids. It sparked something in Heather as she now sits on a variety of Charter school boards and works in education. Her work in Break the Cycle gave the the her tools to write her thesis which was about what the curriculum for the program should look like.

If Heather had chosen basketball she would have never done the work that ended up to be so empowering for her. Many of her friends went on to play basketball but because the odds are so rare to play professional ball especially for women who don’t make that much money in the WNBA as it is. She sees many of them who went that road now lost in their lives. Basketball was seductive but she is so happy she make the choices she did. After graduating, she became a Coro fellow and worked in San Francisco for a year in the the Chevron corporate affairs department, the transportation department and for the first lesbian running for City Council. It was an incredible experience because she learned how Government works.

After the year ended she worked for the Clinton/Gore campaign and then decided to get a MBA. She gt into Yale and spent the next two years in the Northeast. In the summers, she worked for Goldman Sachs and eventually ended up in at the Spectrum Group building out their high net-worth practice and data consulting. hey were acquired and she was thrilled when she was recruited back to San Francisco to run San Francisco Asset Building, an employer based solution to welfare reform. Here is where she got into adult education.

Heather’s leadership took 4000 women off welfare by creating a curriculum teaching these women specific hard skills towards success. This success of this concept has been picked up by several large companies. Using philanthropy to set up consulting and hybrid education models to help people get into the work force was the key to the success.

It was now around 2009 and it was time for a change. She handed off her practice to a friend and started something new in the private sector. Heather decided to create a multi-media sharing network after having a terrible experience with other products. It was there that Heather launched rrriple. She wondered if she could create something meaningful with this technology for the education world. In the 90’s she had learned about eportfolios and is using that platform for rrriple.

Rrriple allows anyone, particularly students, to create muti-media portfolios. When kids apply to college these days the admissions department is looking to create a diverse group of kids and these portfolios give them the ability to look at each application through the same set of eyes. Colleges and universities are accepting more and more media based portfolios and the schools want to be able to have some control over how they receive this information, rrriple does that.

They are even working with MIT sophomores in an independent study class where kids are trying to figure out what they want to do post graduation and they are using this software to build out their resumes. They hope that through this software kids will help graduates end up in jobs that are right for them.

Believe me, there are even more details to this story and it was hard to just filter through it all. Heather is one smart cookie and she has taken every single opportunity as a learning moment to build on her skills for the next move just like playing basketball. Impressive doesn’t even define Heather who is extremely charming and chatty too. She’s got the package.

I will be watching rrriple to see how she figures out how to disrupt a part of education system that needs many Heathers to change our education system in a different direction.

This post was originally posted at Gotham Gal.

About the guest blogger: Joanne Wilson is an advisor and investor in startups, including Curbed (Eater/Racked), Food52, Red Stamp, Catchafire, DailyWorth, Editd, Ricks Picks, Cacao Pietro, Editions 01, Hot Bread Kitchen,, Gotham Gym, The Moon Group and MOUSE. Her most successful venture is being married to her best friend Fred and raising her three kids, Jessica, Emily and Josh. Joanne blogs under the name Gotham Gal. Follow her on Twitter at @thegothamgal.