Survive To Year Five – A Q&A with a Fifth Year Entrepreneur

Becoming an entrepreneur can feel like running an unknown distance race. You step up to the starting line, your heart is pumping, you don’t know what lies ahead, but you are determined to reach the finish line (wherever that may be). As the starting gun sounds, you find yourself thinking:

• Am I going out too fast? Should I conserve energy?

• What am I in for? How long is this race going to be?

• What’s around the next corner? Are their peaks and valleys?

• Why is that other guy doing so well? What does he know that I don’t?

1. How many cups of coffee do you drink in a day? 

   What would I do without coffee?! After 5 years in business, we’re on our 3rd coffee maker. That’ll tell you how much coffee I drink a day.

2. One word to describe you as an entrepreneur?

   (Still) Learning

3. Last time you went on a vacation longer than 5 days?

   I can’t remember the last time I did that. I got married last year and only took 2 days off. My wife wasn’t happy about that. I owe her a long-overdue honeymoon!

4. As an entrepreneur, a penny saved is what?

   A penny saved…often goes towards capital investments. After 5 years, I am still trying to upgrade workstations, equipment, and other assets. As our team grows and we increase our capabilities, my team needs the best equipment to do their best work. It’s expensive to compete with the best-of-the-best in our arena.

5. If you had to choose one, would you say you are a pessimist or an optimist?

   I’m definitely an optimist. The glass is always half full, there is always a silver lining, and lessons are learned from failures. In leadership, a positive, can-do spirit is critical. Even during COVID, I tried to keep my team on track. We focused on what we could do and not what we couldn’t do.

6. What helped you make it to year 5 as an entrepreneur?

   I’ve had some great mentorship and guidance along the way and one of the most important things I’ve learned is to stay flexible and adapting when needed. 18Ninety started as a video production company and now looks more like a marketing agency (although we still produce a lot of videos!). Adapting to the needs of our clients and insuring them we can assist with all of their marketing and advertising needs has really helped us solidify and grow our business.

7. Best way to build a good client relationship?

   The ability to build a good client relationship is based on many things. I focus on three key values that I learned in the US Air Force…integrity first, service before self, and excellence in all that I do. Apply these values to any relationship and you will build trust.

8. How do you set boundaries with your clients?

   It’s less about boundaries and more about expectations. If you set the expectation that you will answer the phone or email at any hour of the day, the client will hold you to that expectation. I always try to be clear and set realistic expectations, and then fulfill those expectations (and exceed them when possible).

9. What’s the longest meeting you’ve been in?

   I’ve had marketing strategy meetings last all day but that is rare. I would say a “long” meeting is greater than 2 hours.

10. How do you build a quality team?

    I think you build a quality team by being deliberate in your selection process. This requires time and effort to accomplish. First, I try to identify the personnel that my team needs in order to excel at accomplishing their tasks. Second, I always keep the culture of my team in mind and seek to find the most talented person that fits my culture. Third, I try to be patient because it’s often a long and deliberate hiring process to find someone. At 18Ninety, we tend to interview people at least three times, in different situations, before we consider hiring them.

11. How do you encourage positive team morale?

    It starts with me. If I’m positive, oftentimes the team feeds off of that energy. I also try to make sure our team laughs a little bit every day.

12. Instead of “leaders are readers” change the quote, “leaders are ______”

    “Leaders are warriors”. It doesn’t rhyme, but it’s true. Leaders have a mission in mind and they go seek battle to accomplish that mission.

13. Does cold calling, or the equivalent, make you nervous? If no, did it ever, and how long until you got comfortable with it?

    I did “cold-call” potential clients for about a week when I first started 18Ninety. It’s never felt comfortable to me so I don’t do it. A lot of our business comes through referral or someone sees a project we completed and wants something similar. I am very proud of that fact!

14. On a scale of 1, being bare, and 10, being can’t see your desk, how cluttered is your workspace?

    A solid 4. But my stacks of papers are tidy!

15. What tool or program have you relied on most to stay organized?

    Sticky notes and Google calendar for the win!

16. What quote have you found most inspirational?

    “Make it simple by significant.” – Don Draper

17. What’s the best part about being an entrepreneur?

    So many things I could list here, but I really enjoy building a team and setting the strategy of my company.

18. What’s the worst part about being an entrepreneur?

    I work a lot and it takes time away from my family.

19. Best business advice you have ever received?

    A big-time CEO once said to me, “All of your company goals should align to these four things: product, brand, distribution channels, and operational excellence.” I think about these EVERY DAY.

20. What would 5-year entrepreneur Jade tell first-year entrepreneur Jade?

You’ve made the right decision and things will get harder before they get easier. Stay the course. Oh, and buy Bitcoin!