Gregory Raiz

MD at Techstars Boston Accelerator

Gregory Raiz is the Managing Director of the Techstars Boston Accelerator. In 2003 he founded Raizlabs, a leading mobile agency which, after being included on the Inc. 5000 fastest-growing companies list four straight years, was acquired in 2017. Since then he has shifted his focus to investing in and working with startups, both directly and through angel groups like TBD Angels. In the last year, he has invested in 18 companies including a number of Techstars graduates. Greg has dedicated countless hours to mentoring entrepreneurs, including serving as a mentor-in-residence with Techstars Boston. He actively speaks on the topics of technology, innovation, and design at leading companies and universities including Harvard, MIT, Tufts, Northeastern, and Boston University, among others.
1. Who is your hero? (In business, life, or both.) I’ve always admired Leonardo Da Vinci. He was able to combine the principles of design, art and technology to improve the lives of those around him. He had many talents, and while he’s considered by most to be an artist, I think of him as a technology entrepreneur. That being said, Ferris Bueller’s my hero. Charming, artistic and clever? Somewhere between him and Leo, you have a masterpiece. 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 can give is to run your business with integrity. You’ll meet a lot of people and have thousands of conversations. Each relationship, client or contact can either be your ally or your foe. To succeed in the long term, you need to collect fans, advocates, allies and people who will help take your business further. Spend time helping others and you’ll find that when it counts, your network is there to help you. Integrity, values and principles are rare but if you build a company on that type of foundation, the organization will be stronger. 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 mistake is not having plans for the unexpected variables that inevitably do go wrong. This includes processes, people, contracts, clients and pretty much everything else. In 2014, we had over 25 percent of our business tied up in one account. We naively assumed that everything was fine, but in the span of a few weeks, we had to scramble to figure out how to adjust a non-trivial part of the company when that account shifted directions. It taught us a lesson on reliance, independence and the importance of having contingency plans. You have them not because you want to use them, but because when things do go sideways, you want to be ready to roll with whatever comes your way. As a business owner, you need to trust your team — that’s the only way your business will grow. As a leader, you also need to protect the business in case things don’t go according to plan. 4. What do you do during the first hour of your business day and why? I try to find a quiet moment to close my computer, shut off all of life’s notifications, alerts and distractions, and make my own list of things that are important. When you first open your email that day, there will always be 100 people who want to impose their lists onto you, but I’ve found it helpful to try to come up with that list myself before the morning rush begins. 5. What’s your best financial/cash-flow related tip for entrepreneurs just getting started? When I started, I wasn’t familiar with accrual-based accounting and I managed the business exclusively by understanding what was actually in the bank account. As a small business, this was fine, but this strategy can ultimately prove to be limiting and stressful. I would get anxious because there was little cash in the bank even though business was strong, and I was using that cash to invest in hiring and growth. Getting my head wrapped around the basics of accrual-based accounting helped me better predict our cash flow and how aggressively we could actually grow the business. 6. Quick: What’s ONE thing you recommend ALL aspiring or current entrepreneurs do right now to take their biz to the next level? If you’re thinking of taking your business to the next level, make sure you can answer: “Why does your company need to exist?” Having an organizational purpose and a reason for being can help you focus on what’s most important to your business, as opposed to what your competition may be doing. As a CEO, your job is to provide clarity on purpose and vision. You need to answer the “why” question. The answer will help you, your employees and your customers understand and differentiate your business from everyone else. 7. What’s your definition of success? How will you know when you’ve finally “succeeded” in your business? “Success” as a noun is not a useful word because it assumes a static metric on your progress, but it doesn’t actually work that way. I started my business out of a Starbucks and I remember when I moved into my first office I felt like I “made it.” I had that same feeling when I hired my fifth employee, and again when I hired my 25th and 50th. As the business has grown, I’ve moved the goal posts myself. After all, success means overcoming obstacles — not finishing a race. Succeeding in business is something that happens all the time: closing a deal, hiring a key employee, beating last month’s numbers. As the old saying goes, “Success is a journey, not a destination.” That being said, life moves pretty fast, so make sure you enjoy the ride.