Jeff has spent the past four years helping 675,000 freelancers and entrepreneurs launch and grow their own personal business and build their own version of the American Dream.

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

Back in 2008 when the market crashed, I made a commitment to myself that I would build a company and a mobile platform that would help people like myself find work as fast as possible. My wife was pregnant with our 5th child and I was scared I would lose my job. I never wanted to feel like that again so I started Moonlighting.

Can you share the most interesting story that happened to you since you started your company?

Lots of interesting stories along our 4-year journey. My most memorable was almost being on Shark Tank. I was in the studio about to walk on stage when the entrepreneur pitching in front of me had a meltdown. Mark Cuban had beat him up a bit and the founder got overly emotional. As I was lining up to go into the tank, the crew came up and said that the sharks were distraught from the previous pitch and were done for the day. That was the last day of the season and I didn’t get to pitch.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Any tech startup founder can attest that mistakes happen often and you are not really growing if you aren’t failing fast and iterating. That said, in our early days I made a horrible assumption. We were going to be a mobile-only company, which meant we would only support a mobile app. We started to receive complaints, primarily from freelancers over the age of 50. They wanted us to build a web version because they didn’t like using the app all the time. We quickly built the website so I could avoid the ridicule I was getting when I spoke publicly or pitched prospective investors.

What do you think makes your company stand out? Can you share a story?

I think Moonlighting stands out because we built something that allows people to be themselves and empowers people to work and earn a living on their own terms. Moonlighting is more of a cause, a revolution of like-minded people who want to work for themselves and create their own version of the American Dream. We, as founders, started the company by moonlighting after our 9-to-5 jobs which is how most great companies are born. Anyone with heart and determination can start a company and we embody that spirit every day through our mobile app. In 30 seconds or less you can be up and running and participating in the gig economy.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Being an entrepreneur is not for the faint of heart. It’s an emotional rollercoaster with extreme highs and incredible lows. The ebbs and flows require a steady mental state and surrounding yourself with colleagues who compliment your personality. I am very fortunate to have two great co-founders, Roy Slater, and Ritesh Johar, who not only bring amazing tech and operations talent to the company but also allow me to drive the business forward while maintaining a work-life balance and avoiding burnout.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

We have been fortunate to be surrounded by great advisors and investors. Chris Hendricks, President of the Local Media Consortium and former McClatchy executive was instrumental in helping us grow the company and raise over $6M in investment. He is the type of board member who gives unselfishly and has played an integral role in building Moonlighting

How have you used your success to bring goodness to the world?

Moonlighting’s mission to simple, we want to help people make money. By helping people build their own independent income stream, we are empowering people to do more with their lives. We help women who want a better work-life balance, build their own business. We help baby boomers, being squeezed out of corporate America, build a successful second career. We help graduating millennials start their first business and frustrated corporate execs branch out and create a business that gives them more purpose and meaning. Helping these groups succeed is what we are all about, and it’s very rewarding.

Do you have a favorite “Life Lesson Quote”? Can you share a story of how that was relevant to you in your life?

I am a big fan of the poem “Desiderata” by Max Ehrmann. I often read it at times of stress and doubt. It helps me remember why we started Moonlighting. The line “Speak your truth quietly and clearly; and listen to others, even to the dull and the ignorant; they too have their story” has great meaning to me. We represent 675K voices now on the platform and each has their own unique story. As stewards of our platform, we need to be mindful and care about each one and that’s what that line means to me. We even built a crowdfunding feature called “Moon$hot Stories” which gives freelancers and entrepreneurs an avenue to share their story and raise money to fund it, similar to GofundMe.

What are your “5 things I wish someone told me before I started my company” and why. Please share a story or example for each.

I have received some very wise advice from many friends and fellow entrepreneurs along the way. Here are just a few:

  1. Raising money is hard, and it will test your resilience and mettle. You need to kiss a thousand frogs before you find the right investor.
  2. Starting the company is easy, sustaining its success will only come with a level of fortitude and determination that you may not have experienced before. Never say die.
  3. Don’t ever lose momentum in the business or your business will die.
  4. Pick a BHAG (Big Hairy Audacious Goal) and pursue with a tenacity like no other. That is how great companies are born.
  5. Stay true to your vision, and avoid the negative noise, as there will be more detractors than supporters early in your journey.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Moonlighting is a movement and is bringing social good to all the users on the platform. Moonlighting is all about community as 30% of our users hire one another for jobs — taking care of one another to make our platform special. Working for yourself is very scary, but it becomes less scary when you are part of a group of like-minded entrepreneurs and freelancers who want to help you become successful. Moonlighting represents all that is good with society and we are proud to provide the tools and solutions to help the community flourish

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This was very inspiring. Thank you so much for joining us!


  • Dillon

    Founder & Editor-In-Chief of Kivo Daily Magazine

    Kivo Daily

    Dillon is the Founder and CEO of MentionWorth. He is an award-winning internet entrepreneur, writer and keynote speaker.