Reuben Vandeventer, an IU Bloomington alumnus, is co-founder of S2 Data Risk. The company enables businesses to account for data risk and safeguard against unintended consequences that accompany the digital economy. Its product and built-in assistant help maintain the economic well-being of clients’ data.
Crimson Catalyst: If a person has an idea for a business, what are the first three actions they should take to make it a reality?
Reuben Vandeventer: I’ll provide two perspectives on this: the idealist and the pragmatist. The idealist view is an absolutely required mindset when pursuing anything significant. If you want to start something, figure out the first steps you can take in a direction notionally aligned to your goal. Get started, that is, take those steps immediately, and — the most important part — keep going. This mentality has always worked for me to ensure that I’m iterating toward the goal.
The pragmatist view is equally important and balanced, and it should be included in the first steps above. Every idea in entrepreneurship should undergo thorough reality checks, because ideas are easy to generate. Tools I’ve used to filter out good ideas from bad is the use of required metrics that illustrate the market viability of the idea. The two metrics I force myself to be able to answer with fairly rigorous detail are Total Addressable Market and Beachhead Market. Essentially, forcing these two numbers to exist ensures that I’m researching and finding the buyer, sponsor and user personas who would interact with and ultimately create the decision-making unit associated with the idea.
Holding the idealist and pragmatic views together is helpful to manage the right level of optimism required to want to pursue an idea while also challenging that idea to keep getting better, more detailed and ultimately more real.
CC: What has surprised you during the course of your day-to-day entrepreneurial journey?
RV: It’s really hard. I launched, grew and sold my first company a few years ago, and we were able to do that in a fairly short time period — approximately three years from launch to exit. Each of those three years had a distinct life of its own. The first year was euphoric, and the world was our oyster. Year two was a reality check that enterprise sales, or business-to-business, is difficult and requires almost more sophistication than the actual services and products that comprised our expertise and market differentiation. Finally, year three was a whole new experience of going through rigorous due diligence of the acquisition process.
The biggest surprise is that it is completely OK to be transparent about your individual goals and objectives with folks you are trying to structure and do deals with. Whether that be customers, buyers or acquirers, suppliers, partners, or investors, transparency around your goals enables those individuals or entities to evaluate how to be helpful or not, which optimizes everyone’s most valuable resources of time and attention.
CC: How do you define success?
RV: Success is doing what you want and how you want to do it. I also have learned by working at some really phenomenal places — Bridgewater being the most influential on me — that it’s really important to work with people you enjoy spending time with. We spend a significant amount of our lives working, so optimization of that time is an absolute measure of success.
CC: What is dangerous or scary about being an entrepreneur?
RV: Almost everything! Despite how whimsical and idealistic the thoughts of being a successful entrepreneur might be, the truth is that it is unbelievably hard. Having had success in both the corporate world and in entrepreneur land, I can say fairly objectively that I don’t believe one is harder than the other; however, the consequences of your daily actions are more extreme in entrepreneur land than in the corporate world, which brings with it more stress and anxiety.
You can have substantially more success and impact, and deliver more value, as an entrepreneur than you might in a structured corporate career track, but you can also just as easily have substantially more failure, deeper lows and higher stress as an entrepreneur.
CC: What is the best advice you’ve received?
RV: A mentor who has been keeping me on the rails for years constantly reminds me that “something isn’t common sense until it is common.” What he means is that you often have to get into the details of things to understand how they work, and then it becomes common sense to you. Too often we oversimplify and dumb things down for the purposes of marketing and sales, but that is absolutely the wrong approach when the problem or opportunity you’re pursuing requires innovation and creativity. Sometimes it’s vitally important to respect and appreciate the detail in order to gain understanding.
CC: What is the best advice you can offer?
RV: Don’t fall into the trap of romanticizing your dream to the point where it feels better to “leave it as a dream.” If you dream about being an entrepreneur, then get to it; start right now on the best first step you think you can complete by the end of the day. Then tomorrow, just do that again. Having this mindset keeps you from spending too much time dreaming and a lot more time testing a business hypothesis.