The start of Possip was a dinner table conversation between Founder & CEO Shani Dowell and her husband.

They’d met in Nashville in 2005 while working at KIPP, a national network of nonprofit schools serving kids who’ve had unequal educational opportunities.  Shani’s job was to help school leaders launch their new schools, and her (now) husband was one of those leaders.

Fast forward over a decade. Since that time, she’s been a middle school math teacher, led the Nashville Teach For America region and talked with and known hundreds of teachers and school leaders.  That one KIPP school has grown into a region of six schools. 

Through this journey, Shani got to know intimately the experiences, joys, and challenges of teachers and school leaders. She also has two school-aged kids, which adds an additional dimension to our educational experience.

So when that dinner table conversation moved to a stressful relationship her husband was dealing with with a parent at his school, she found herself empathizing with both parties.

As the conversation progressed, a few themes arose:

1. This parent, like most parents, didn’t have a way to identify an issue when it was small or to share this issue with their child’s school.
2. This school, like most schools, didn’t have a way to identify trends or collect data systematically.
3. Teachers often only hear from parents when there is a problem and don’t get to hear the positive impact of their work.
4. Parents often talk to each other and share information or questions or concerns about schools but that information doesn’t cross into the walls of the schools.

The couple also reflected on the greater barriers that exist when there are lines of difference in educational experiences, socioeconomic status, race, and language.

“What if we made it super easy for parents to share?  What if we sent them a weekly text prompt that helped them think about the week and identify issues.  What if we made it super easy for them to share – and prompted them to share praise and feedback?“

Shani became obsessed with the idea that it has to be easier for all parents, regardless of their background, to share with their kids’ schools.  And a positive bridge between parents and schools that is steeped in trust, learning, and feedback has to, and can, be built.

And so she started Possip, a platform for schools and parents to gather important insights and feedback from families and staff.

We sat down with Shani to talk with her about starting her company, her initial bootstrapping experience, raising over $1M in venture funding, leadership, Nashville’s tech scene, and more.

You’ve got over 80,000 users in over 160 schools. How did you gain that traction?

Our path towards over 160 schools and 80,000 users are a combination of initial sales to high-fit customers and prospects, word of mouth growth based on existing customers and parents, and focusing on marketing and outreach so we can find our next set of customers.

While I was starting Possip, I was still working full-time at my day job.  Before I even started “selling” we’d done a semester-long pilot with a school.  Then, after we saw the positive impact for parents and administrators at that school, we set a goal to sell it to five schools over the summer to gauge if this was a valuable enough product for schools to pay for. 

From there we have seen constant growth – from five schools in August 2017 to 15 schools by March 2018 to 40 schools in July 2018 (which is when I went full time to Possip) and then doubling by August of 2019 and continuing to grow from there.

We also went from selling to individual schools to being able to sell into districts.

You really dug in on the bootstrapping mentality to grow Possip at the early stages. What were some of the key actions or processes you took to do so? What were some of the difficulties?

One of the key steps I took early on was to keep working in my day job.  I let my employer know after some initial success with Possip that I wanted to scale down to 80% of my full-time hours. 

I also knew there were things that needed to happen that would significantly push the work forward. One of the best things I did was use my “day job” salary to pay for staff members to take on some of the work I struggled with due to time, experience or interest.  These areas included finding people to help with accounting, legal, design, and business development.

Some of the difficulties in this were often knowing that by the time I finished my “day job” I didn’t have the mental energy to make the decisions I needed to make for Possip.  This made hiring talented people who could help me navigate these new waters so important.

My challenge was and remains to find the best ways to optimize the resources I have. 

You’ve raised over $1M in venture funding. How was your fundraising experience?

I’ve been really fortunate that my investors are people who have the best interest of the company in mind. The process of raising money can get demoralizing, especially if you are facing any discrimination.

I found it important to consider each investor meeting a learning experience as well as a fundraising opportunity and to grow from it. There are sharks out there, and as an entrepreneur, you shouldn’t doubt your instincts about what’s best for your company or sacrifice your timeline for the sake of their financial goals. You’re potentially advocating for a solution to a pain point that prospective investors haven’t experienced and they might have a hard time wrapping their minds around it the first time.  The right investors for your company will understand your sector, your product, and your leadership 

You serve as an Entrepreneur-in-Residence at the Nashville Entrepreneur’s Center. Can you tell us about your role?

Last year a few fellow entrepreneurs along with a team member from the Nashville EC identified that there was a gap in supporting Black and Latino founders in the earliest stages of their companies.  Kipkosgei Magut was the brainchild for this idea – and Twende, a summit for Black and Latino founders emerged.  We put on a day of learning and connections. Out of this the Nashville EC created the Twende program.

What’s the one top personal leadership trait that you’ve found invaluable in your process, and, conversely, did you identify one area that you felt you needed to improve upon to get the job done?

Definitely the most invaluable is a combination of persistence and problem-solving skills. There are lots of times you’ll be told no or occasions when the first path won’t work out.  To be able to keep generating solutions and forge new paths is super important.

The common denominator of these two skills is the ability to keep learning. As a young entrepreneur, I recognized that I need to work on how I articulate my confidence. The confidence isn’t the problem, it’s all in the delivery! I use a lot of modifiers and communicate with nuance – which doesn’t always translate well into confidence or certainty.

Nashville has really grown as an up-and-coming startup scene. What do you see as being Nashville’s strengths in this area, and what are some of the places that could be improved upon?

I think the top thing about the Nashville startup ecosystem is the community.  Whether through Launch TN, the Nashville Entrepreneur Center, Nashville Business Incubation Center, Pathway for Women, the SBA, The Lab, Blacks in Tech Nashville, Black Business Boom, etc.  There’s such a strong community of entrepreneurs and ecosystem leaders shaping the path.

Anything else?

These are tough times in our global history.  It helps remind us of the very real and important role entrepreneurs and small business owners have in our daily lives, in our economy, in solving big problems, and in leading.  Women are at the forefront of this, and if anything, the uncertainty we’re facing today speaks to the need to ensure that we have diversity among the decision making bodies and at all levels of leadership across our country.

Possip’s Founder & CEO, Shani Dowell is a former public school teacher.  As a parent and educator at heart, Shani loves supporting the work of schools. Shani attended public schools in Houston, Texas and went to Howard University in Washington, DC. She started her career at Bain & Co. and helped launch Posse Foundation’s Boston office.  She has an M.B.A. from Stanford University and has worked for Houston ISD, KIPP, Teach For America, Bridgespan Group, and Relay GSE.  Shani’s goal is to support schools through the ideas of parents, teachers and students.