To Find Billion-Dollar Success, This Founder Learned to Think in 3s

“20 Questions” series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders. In the world of signatures, there are really two standouts: John Hancock, founding father of the United States of America, and Tom Gonser founder of DocuSign. In 2003, Gonser thought he had a pretty good idea with “e-signatures.” And as the numbers show, most of the world agreed. DocuSign is reportedly valued at $3 billion dollars, and has more than 200 million users in 188 countries. Its client roster includes Microsoft, Salesforce, LinkedIn and SAP, among many others. Gonser, now serves on the board of DocuSign and is an investment partner at Seven Peaks Ventures. We fired off our 20 questions to the relentless innovator and true to form, he responded digitally. Would you expect anything different?

Here is what he had to say:

1. How do you start your day?
At 6 a.m. I check communications for any emergencies and adjust the calendar for the day. Then a quick workout. As a matter of focus, I try to do 50 pushups every day. It sounds simple to say, “I will do 50 pushups every morning”  but it requires follow-through and reinforces the fact that being healthy underpins everything we do.

2. How do you end your day?
Because my day is so diverse —  travelling, meeting with companies, developing strategies, writing, (and making wine!) — I rarely have a regular day end. I do always manage to determine my next AM schedule as a last step, because my calendar is rarely the same at noon as it is by 5pm.

3. What’s a book that changed your mind?
Made to Stick is a current favorite.  It shows the importance of telling stories, and communicating in language people can hear, remember, and retell.

4. What’s a book you always recommend?
Made to Stick again, because it does a super job of explaining how communications can be memorable by including context and stories. Too many people try to cram in extra words making it hard to remember. Crisp communications and telling stories is so important.

Related: This Successful Entrepreneur Shares The Trick That Helps Her Tell The Difference Between Being Productive and Being Busy

5. What’s a strategy to keep focused?
Short lists with big strategies. Keep the important stuff top of mind. Long lists just waste time as you try to categorize things you are not going to get to.

6. When you were a kid, what did you want to be when you grew up?
A marine biologist. Still do. Maybe I will someday.

7. What did you learn from the worst boss you ever had?
I learned that I am the only one responsible for my career, no matter what bosses or HR departments offer up. A career needs to be internally driven and focused.

8. Who has influenced you most when it comes to how you approach your work?
My father told me when I was young that I could do anything if I applied myself. Basically, if you want something, you need to be prepared to work harder than anyone else to make it happen.  That eventually led to my favorite saying, “Nothing succeeds like persistence.”

9. What’s a trip that changed you?
I had a chance to spend a week in the Galapagos islands and was struck by how impressive the web of life is on this planet, and how important it is we protect what we have before it is too late.

10. What inspires you?
Tesla inspires me. Tesla took on an “impossible task” and proved that it was possible.  I think Elon Musk is one of the very, very rare actual inventor business leaders. It is impressive to see a CEO who can go so deep on product, technology and strategy when so many large company CEOs simply cannot.

11. What was your first business idea and what did you do with it?
My first business idea was to build sailboards when I was in college. I learned how to sail right as that industry was getting started, and I really liked it. I could not afford to buy the most leading-edge equipment, however, as a small business, we could get demo equipment, and actually build the boards ourselves. We had fun, made all sorts of mistakes, but did make some sailboards in the early days.

12. What was an early job that taught you something important that you still use today?
Swimming competitively taught me that even if you work hard, you may not get results you want. One year we trained for nationals and my times were actually worse than the year prior. I learned to just move ahead, focus on the next year, and go for it.  The following year I broke all my personal records and placed in the top eight in two strokes at nationals.

13. What’s the best advice you ever took?
Take money when you don’t need it.

14. What’s the worst piece of advice you ever got?
I changed the core ideas for a product based on input from someone who was an “expert” but who really did not understand the full vision. The result was failure of the company.

15. What’s a productivity tip you swear by?
Think and communicate in 3’s. I find that setting goals, strategic plans or metrics should be distilled into no more than three items. People can hear and recall three items easily, but even four creates a focus problem. Framing things with no more than three elements creates “actionable communications” — things people can accomplish without more instruction.

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
Not surprising, I am a big fan of Google Spreadsheets. So flexible!

17. What does work-life balance mean to you?
It is a long-term thing in the world of startups. At any point along the line, things may not be so well balanced. However, over the long term, there are things that you can do to provide some sense of balance. Think: work super, super hard for one year, and then completely disconnect and spend a week with your family. Do this for 10 years, and if you win, you can spend 100 percent of your time with your family afterwards, pay for college, etc. The reality is that starting a new company requires the founding team to make trade-offs — family time, location, career risk and pay — for a period of time that others may not be willing to do.

18. How do you prevent burnout?
Give yourself the permission to disconnect completely from your day job — doing something with a totally different thought pattern. This is usually some hobby, art, music or area of research.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
Do something that requires 100 percent focus away from the problem you are trying to solve.  Then on the way back to the real world, things can be seen from a different perspective.

20. What are you learning now?
I am a partner at Seven Peaks Ventures investing in early-stage technology companies. With my own companies, I’ve raised over $300 million as an entrepreneur, so it is natural to play a role on the “other side” of the table. Helping early-stage companies win is a huge passion of mine, so I’m now fully engaged with this. Our operational approach to investing helps our companies reduce risk and move faster, because we can help them avoid mistakes we’ve made in the past.

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