Jason Shah is the founder of Do.com, formerly of Yammer and INeedAPencil.com.
Who is your hero?
Bertrand Russell. He’s a modern philosopher who has distilled a lot of the complexity of life for me through his writing (especially through A History of Western Philosophy).
What’s the single best piece of business advice that helped shape who you are as an entrepreneur today, and why?
Be honest. It seems like general life advice, but in a cutthroat business environment, honesty has made me a better person and given me a leg up in business. It helps you connect with people more genuinely, get to the heart of issues faster and it feels better than any form of being disingenuous or anything other than yourself. Being honest also enables you to keep reality and fantasy in check — so that your delusional optimism as an entrepreneur doesn’t get the best of you. Honesty keeps your true north clear and reduces burdensome cognitive dissonance.
What’s the biggest mistake you ever made in your business, and what did you learn from it that others can learn from too?
I worked by myself for too long. As someone who needs to keep his micromanager in check and is a bit OCD, I wanted control too much at the cost of impact. There’s a balance, to be fair. You don’t want to jump into a cofounder relationship too quickly, or raise capital before you’re ready. But with Do.com, I found wonderful partners with SherpaVentures, SherpaFoundry and Salesforce — not to mention a high-caliber founding team — that makes all the difference to date. As they say: “If you want to go fast, go alone. If you want to go far, go together.”
What do you do during the first hour of your business day and why?
I think. The day gets filled with email, meetings, etc. too fast. Your best thinking likely is when your mind is fresh, and it helps ensure I focus on the important, not just the urgent.
What’s your best financial/cash-flow related tip for entrepreneurs just getting started?
Be frugal. But don’t be penny-wise, pound-foolish either.
Quick: What’s ONE thing you recommend ALL aspiring or current entrepreneurs do right now to take their biz to the next level?
Ask yourself what’s the biggest issue with your company you haven’t addressed yet because you’re too busy or just haven’t taken a step back. That clarity will help elevate you.
What’s your definition of success? How will you know when you’ve finally “succeeded” in your business?
Success is about personal fulfillment. Some people define this in terms of impact, money, or any number of other factors. But at the end of the day, we are humans and we need to be fulfilled. We need meaning, as hard as that is to define. This is key though: Whether you’re 20 or 50 or 100, a person without a sense of fulfillment can never truly feel successful unless they limit the definition of success to a bank account or external validation. So define fulfillment and work to find it.
