An Interview with Lauren Holliday

Manging Editor & Founder of Freelanship

Lauren Holliday interview

Lauren Holliday is the creator of the first course on full-stack marketing. She’s a part-time editor at Entrepreneur and the managing editor of Vandelay Design. Lauren loves radical candor, the beach and companies that pay their interns.

In this entrepreneur interview, Lauren shares how she likes to do things differently. She’s the definition of an entrepreneur who marches to the beat of her own drum.

In order to become successful, her biggest piece of advise is to surround yourself with brilliant friends and mentors who are smarter than you are. That way, you could quickly learn and evolve as an entrepreneur. Keep reading for more killer advice and be sure to follow her on Twitter!


What do you typically tell people when they ask you what you do?

It really depends on who I’m chatting with. I do a lot of different things so it’s much easier (and much more attention-holding) to simply say one of the things I do based what that person would care about hearing.


Have you encountered troubles or mishaps when starting Freelanship? How did you fix them?

Ha! Where do I begin? I think the toughest part of Freelanship has been finding a good and reliable co-founder. It can be wildly difficult to find someone who is as passionate as you are about your baby.

I have zero interest in learning to code. I’ve tried and hated it numerous times. I just can’t get into it. That’s definitely a problem too since getting a custom platform built requires mad money – like around $100,000 – and that’s on the low-end of quotes I’ve received.

To solve my co-founder problem, I utilize my rich network of brilliant friends and mentors, who are 1,000 times smarter than me. They help through any and every technology issue.

As for the platform problem, I have a solution in the works. Stay tuned. (Remember, be resourceful when you don’t have the resources.)


What do you enjoy most about being an entrepreneur? Is there something you are most proud of?

While the entrepreneur lifestyle is very demanding, it’s also very flexible, which has come to be a requirement for a happy life for me. I love building things. And I love helping people, who are struggling to help themselves. I also LOVE solving people’s problems. I’m not sure why I enjoy this so much. It just feels really good, I guess.

Hmm. I would say I’m most proud of my former intern and friend, Lexi Merritt. She found me in a Facebook Group we were both members of, when I posted a paid internship to the group.

The minute I read her writing, I knew she was special – with that sort-of raw talent. It’s so effing exhilarating to see someone you’ve sort-of helped (I don’t want to steal credit for Lexi because she’s just amazingly talented on her own) along the way really fall into loving content marketing and doing phenomenally well at it.


What is the most exciting moment of your entrepreneurial journey?

There’s been many. But I’m also easily excited. =) It’s exciting to get an email from someone who you would’ve thought would never even know you existed.

But the most exciting thing, I’d have to say, by far, is selling out my full-stack marketer course in 1.5 days. It was shocking to me how much people wanted it. That made me happy because I worked hard on it.


What is the toughest decision you’ve ever made when starting a business? How did it make you better at the end of the day?

There’s been a lot. I think deciding to give up recruiting a co-founder. It’s made me stronger and more resourceful and creative. Constraints are good.


What does your day-in, day-out look like? Is there any specific habit that has helped you become a better person?

It’s different everyday. Lately, it consists of a lot of writing, editing and communicating/supporting/fixing.

Waking up early and forcing myself to get more sleep. I hate sleep because I feel like every time I’m not working, someone else is and I’m falling behind. I realized though that by staying up all night, I was actually slowing myself down because I was totally groggy and cranky the next day.

Get some sleep!!


Who has been your greatest influencer along your entrepreneurial journey? How did they shape Freelanship?

There’s so many people I can’t even list them all. We’d be here for a long time. People I haven’t even met have touched me and influenced me along the way.

But if I had to pick one person, it’s Dan Schawbel.

Dan Schawbel’s research spurred the idea for Freelanship. I remember interviewing him years ago, in 2011, for a cover story I was doing on internships for a local newspaper, and he is just so smart. He was talking about stuff no one else was. That is how you win me over – no questions asked.

Dan’s also a super quick thinker, and he’s so strict with his time. It’s wildly impressive. I hope one day I’ll be able to be as quick and streamlined as Dan.


How do you balance life and work to remain connected and available for your loved ones? Any advice for me?

I’m not the best person to answer this question. I believe in something called the four burners theory.


Do you think being an entrepreneur has turned you into a better person? If so, how?

I don’t “being an entrepreneur” has turned me into a better person. I think the hunger and constraints I faced forced me to become a resourceful entrepreneur and become a much better person than I was when I just a college student.


What advice would you give to our readers who want to start a business in Florida today? Where should they start?

My advice would be to surround yourself with people smarter than you and more motivated than you. Surround yourself with a diverse group of people. This is the fastest way to gain more dots (insights) to connect together and solve whatever problem you’re trying to solve.

Surrounding myself with different groups of individuals changed my life, and I highly recommend you do the same. The first step is make smart, motivated and nice friends.


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About Ryan James

Half hardworking hermit, half avid adventurer, Ryan founded Startup Savant to simplify entrepreneurship and pay it forward by donating a portion of all revenue to support children's education via