Critical Points: The Places Where I Needed Support As A First Time Founder

I’m presenting tonight at an alumni event for Washington University in St. Louis, the university from which I graduated with a degree in political science and education. I was invited to share insights and experience as an entrepreneur to help inform how Wash U could better support entrepreneurs. As writing is a process of thinking for me, I thought I’d throw them down here, quickly. Apologies in advance: This essay. requires a good proofread and editing.

When I received the invitation, a text message from the executive director of alumni relations for the Bay Area, the first thing I thought was this: How did they know I was an entrepreneur? I’ve yet to find out. I’ll let you know.

I’m a three-year old entrepreneur. Doing this is a second career for me. And a very different one.

Before that I was an educator, a researcher and social scientist supporting the reform of public education and redesign of high schools. My tool was research and my product was knowledge, through the form of publications and training. It was intellectually rewarding and efficacious, but was insufficient for scaling the innovative practices that could move the needle. After nearly ten year at Stanford University, I was done. Having been inspired by a partnership I launched with the d.School, I left in search of a problem I wanted to solve. It came to me after taking time to travel and repeatedly not having cash to tip. It seemed crazy to me that I could rebalance my portfolio and pay multiple bills at once, but not send a simple tip.

In 2015, I founded a company called TipGenie. TipGenie is a mobile payments and social impact startup in the hotel, travel, and service space. We’ve built, Gratus, the first integrated platfrom that enables cashless tipping, real-time feedback, and emotionally intelligent business analytics. What makes us different from any other business intelligence platform? Our motivation: We’re determined to solve a small, but significant painpoint. In an increasingly cashless society, people not having cash will have a disproportionately negative impact on tipped service workers. With women comprising 80% of the service industry and 99% of hotel housekeepers, that is a problem.

Solving a social problem through technology is a risky venture. I’m one of those entrepreneurs very likely to fail a slow and painful death. The kind of entrepreneur who is so obssesed with solving the problem I’ve set out to solve. I’m also female, first-time, and non-technical. Seriously. Who would do this? Not many.

But here I am, supported by a bootstrapped team of six, who are all burning their candles at both ends to see this through. We do believe that what we’re doing matters, that the solution is clear, that the path is mapped, that there is clearly a product-market fit. So why is this so damn hard? And why are we now entering Year 3?

It’s hard because it’s hard. Read any article about entrepreneurhip and they will all say the same thing: Building a company is hard. Leading a team is hard. Surving the market is hard. It’s hard and will continue to get harder.

At this point, being asked to reflect, I think there are five places where I could have used support.

  1. At the start. Starting a company is like starting a company. Those with children will relate to the experience of having their first child. It’s exciting. You tell people. You’re anticipating the birth of a child, the start of a new chapter. You prepare, you imagine, you plan. And then it happens. And your world is turned inside out. Your sense of time is transformed. You feel a level of responsibility unlike anything else. Having support those first few weeks of a new child is critical. Just having someone say, I know. I’ve been there. It’s ok.
  2. When I needed answers. We all have questions. What do you do when the answers are expensive or you don’t know people who can help? There were many times when I had basic but important questions. I remember being on the phone and watching the clock. After 15 minutes I sill didn’t understand but that was all I could afford. Finding a solution when you’re a startup is like going to the doctor. Asking: Do I take this or take that? You’re handed a Kleenex. And a bill for $800. Getting legal help is kind of like that.
  3. During dry spells. During the “Valley of Death — the purgatory point in between MVP, Pilot, and going to market is tought. You feel proud to have gotten to this point, to have traveled and then you climb over the hill. And there you see: a desert. And you have a bottle of smart water and 30% left in your battery. Any misstep is costly and can send you sinking into sand. You keep going toward the mirage.
  4. When I needed to know someone who could X. Introductions to decision-makers. Going on blind date is 10x more effective than going online and searching for a date. The latter is how I had made inroads.
  5. When we need $. Enough said.

I’ll keep adding. For as long as I can.

Founder & CEO, TipBrightly.io | PhD education | qualitative social scientist | lifelong learner | social entrepreneur | first time startup founder | big tipper