1. Who is your hero? My life and business hero is Jim Henson. He built a creative company that brought joy to millions, jobs to thousands and changed his industry while staying financially responsible. I’m mindful that The Henson Company spent many years paying the bills with commercials, industry films and contract jobs that brought their design skills to other organizations. But amid all that they created the Muppets, helped bring “Sesame Street” to life, shot several movies and have made me laugh since I was a child. That knowledge has always helped me understand that diverse projects can further your company’s goals if they tap the right skills and pay well enough, even if they aren’t part of your core mission. My vision of a great company is about bringing together different talents and perspectives in order to make something great, even though it seems like everything is constantly threatening to collapse around you. That’s a lesson I think I learned from “The Muppet Show,” and pretty much sums up the experience of entrepreneurship. 2. What’s the single best piece of business advice that helped shape who you are as an entrepreneur today, and why? The best advice I’ve ever gotten on entrepreneurship was to be wary of definitive advice about entrepreneurship. It was to remember that every market in every time period has different dynamics. It’s those market dynamics that determine the right way to build your company, not any canned advice. For Testive, we are in an established market — high-stakes test preparation – where customers pay for our services. We raised a $500,000 angel round, but have been able to do much of our product validation using customer revenue because our market allows for it. 3. What’s the biggest mistake you ever made in your business, and what did you learn from it that others can learn from too? The biggest business mistake I ever made was in a prior business. I refused to trust that others could solve problems as quickly or as effectively as I could. Before Testive, my co-founder and I produced a weekly web series called “The MBA Show” as students at the MIT Sloan School of Management. As we approached graduation, we looked to transition the show to a new generation of hosts and producers. We made the mistake of only allowing our potential replacements to work on the more mundane aspects of the show. Without giving them substantial responsibility and letting them experience the rewards, we never got anyone invested enough in the show to carry it on after we left. If I had to do it over again, I would have been more willing to let others take on more responsibility faster, and I would have shifted my job towards doing what it took to make others successful. It was my first — and hopefully last — botched transition from a founder-led project to a real team. 4. What do you do during the first hour of your business day and why? Like many entrepreneurs, I consider every hour of my day to be part of my business day. Recently I’ve started waking up earlier and shifting my morning hours toward exercise and self care. Mornings are my period of highest energy, but my period of lowest ability to focus. I start the day with a workout followed by at least 10-15 minutes of silent meditation. Since I made exercise and meditation a regular practice, I’ve noticed a marked improvement in the quality of my days. I’m able to begin every day in an upbeat mood, which is better for me and better for the team. No one has a good day when the CEO of a small team shows up in a bad mood. 5. What’s your best financial or cash-flow related tip for entrepreneurs just getting started? If you are going to bootstrap with a revenue source outside of your core product, make sure to pick a source of income that helps you gather more information about your core market, customer or problem. Do not just pick the opportunity that generates the most money. To bootstrap our company, my co-founder and I worked as test prep tutors. The money was just okay, but in the end, working as tutors allowed us to conduct valuable market research and understand our customers better; Testive provides effective test preparation by combining an adaptive online platform with a human coach to monitor students and keep them on track. It let us think about our business, even when we weren’t thinking about our business, and it was easier to context shift between the software we were building and tutoring than it would have been to work on an unrelated contract development project. The bottom line is that everything you do takes mental energy. I don’t think we could have put the same mental energy into our business if our source of cash had been unrelated to our idea. 6. Quick: What’s ONE thing you recommend ALL aspiring or current entrepreneurs do right now to take their biz to the next level? Put in place whatever systems or boundaries you need in order to stay emotionally balanced. Older entrepreneurs often say this, but it’s clear from their stories that they only made big changes after they had achieved what looks like substantial success. If you do hear one of these stories from an entrepreneur, ask them what motivated the change. I’ve found it’s usually a massive problem in their physical or emotional health, and that after those changes, all of them saw more, rather than less, success. One adviser told me that it’s because success requires good judgement, not just hard work. And good judgement requires reasonable levels of physical and emotional health. When it comes to judgement, you are either functioning well or not functioning at all. 7. What’s your definition of success? How will you know when you’ve finally “succeeded” in your business? I have three goals for Testive: - Help students improve their academic options and learn new things as painlessly as possible. - Build a business that demonstrates that for-profit companies can create real innovations in education. - Create a great return for investors. I believe that achieving the first goal will drive the second, and that achieving the second will drive the third. Achieving these three goals together will indicate our success.