Lauren Holliday – Founder of Freelanship

Read, and read a lot.

Lauren Holliday the founder of Freelanship, a freelance marketplace with pre-packaged marketing gigs, and Full-Stack Marketer, the first course ever on how to become a full-stack marketer.

Holliday is also journalist with a marketing mindset – a T-Shaped person, who specializes in crafting and marketing content but knows and has experience with the entire marketing stack.

Currently, she’s a freelance editor at Entrepreneur Magazine. Previously, she worked part-time for HubSpot’s and SitePoint.

At, her KPI, which she always exceeded, was 15 percent MoM growth for the number of job posts and job applications. In her best month, she increased the number of job posts by 76 percent and the number of job applications by 37 percent.

Simultaneously, Holliday was the Entrepreneurship Editor for SitePoint, where she was contracted to grow its struggling blog from nothing to 100,000 unique weekly visitors in less than three months.

In her spare time, she enjoys answering questions on Quora, where she’s a most viewed writer for the following topics: Startups, College Advice, Lean Startups.

Holliday also enjoys writing for an array of publications, including but not limited to: Business Insider, Entrepreneur Magazine, Fortune, The Economist, The Daily Muse and TIME Magazine.

She loves radical candor, the beach and companies that pay their interns.

Where did the idea for Freelanship come from?

I got the idea for Freelanship in 2012, when my father told me “No more internships, get a job,” and he cut me off. I was devastated, but I quickly realized I wasn’t the only devastated Millennial whose parent said this.

I met Kyle. And then I met and interviewed hundreds of other interns, when I began heavily researching internships for a cover story I was writing forOrlando Weekly.

I read an eye-opening book by Ross Perlin, called Intern Nation. Then I spoke with The Intern Queen, Lauren Berger, and I interviewed Millennial Expert and Best-Selling Author Dan Schawbel among many other internship experts.

I found disgusting, eye-opening data from The Economic Policy Institute and NACE.
And to be frank, I was beginning to get pissed off… and not at my father for cutting me off, but at these employers who were requiring these grueling and demanding unpaid internships yet were never hiring any of their interns.

Then I began getting aggravated with the privileged students, like this woman, who had the luxury of interning for free with Conde Nast in New York because her parents paid for it.

This is what she told me in an interview:

“It’s funny, it is a little Devil Wears Prada. I do a lot of coffee runs. I do a lot of personal things sometimes. [She’ll] be like, ‘Go pick up my dog, go get my dry cleaning.’ I mean, I do some of that, but it’s only because they have so much work to do that they don’t have time to do it themselves.”
When I asked her what the most exciting thing she did during her time working for free at this conglomerate, she elaborated about the time she was able to be the door hostess for an America’s Next Top Model shoot.

Seriously? I was disgusted and enraged because her internship among all the other shitty, unpaid internships contribute to increased inequality and widen an already massive Skills’ Gap.

Internships are a luxury that people in power consider a requirement. To be exact, 91% of companies expect grads to have 1–2 internships on their resumes, even though the majority of them rarely hire their interns.

And, honestly, why would they hire (i.e. pay) interns when they can replace them with a new wildly motivated freshman, who is just dying to gain experience and totally willing to work for free — just like the woman mentioned above did. This is how we intern ourselves out of jobs.

Stats prove that the minority of students, who do intern, are able to because their families have the resources to support them so they don’t have to pay their own bills.

According to Intern Bridge, 64% of students report they’d have to work a SECOND job if they accepted an unpaid internship (in addition to their college workload). And only 35% of students report their parents would help them financially if they chose to undertake an unpaid internship.

So it’s exceptionally fair to claim that unpaid internships contribute to making wealthy students wealthier and poor students poorer. Why? Because employers are always going to hire the graduate with professional experience for their full-time job, and wealthier students are the ones able to participate in these unpaid internships.

But why should this matter to you as an employer?

It should matter to you because Millennials (those born between 1982 – 2000) are now the largest consumer group. There’s 83M of them or rather 26% of the entire population.
The problem for ALL OF US is they can’t get a job, and if they can’t get a job then they can’t spend any money, which kills our economy.

In order to make the economy better: students need to gain experience before graduating so employers will hire them and close the Skills’ Gap.
Clearly, they need something that’s: flexible, affordable and valuable for their portfolio.
We’ve reached the tipping point. Everyone is pissed off and fed up.

Employers are saying job seekers don’t have the skills they need to fill their company’s Skills’ Gap. They’re fed up with shoddy freelancer marketplaces like UpWork. And they’re trying to market to these young people, spending millions and millions on researching Millennials, who don’t even have any money to spend with their company because they’re unemployed or underemployed.

The only way to understand Millennials is to work with them. They’re much more likely to spend money with a company they like than one that just tosses their resume in the trash and doesn’t give them a chance.

Students are fed up with being stamped as “unpaid interns” for years after graduating college.

Colleges know they need to increase their ROE (Return on Education) fast, and parents are sick of having their kids live on their coach and be dependent on them until the late age of 30 or older.

This is why I created Freelanship.

Freelanship will be responsible for getting hundreds of thousands of millions of young people access to paid, quality and flexible experience opportunities, which will translate to lines on their resumes, but more importantly, remarkable portfolio pieces and valuable, professional connections, not to mention, paid freelance work while in college.

Eventually, these experiences will end. They will have made enough connections and gained enough experience for a full-time gig or to increase their freelance rates or maybe even to create and run their own business someday. The idea is career progression.

We don’t want to hold someone to Freelanship, like UpWork does. And we don’t want to block talent from connecting with employers, like WayUp does, because that defeats the purpose of helping young people gain valuable connections and employers from meeting talent who may be interested in full-time positions with their company.

I want companies to be able to economically and efficiently test talented and motivated individuals, who may be looking for full-time employment, by giving them projects to work on that they need completed. My hope is that they’ll love the freelancer’s work, and offer them a full time position with the company or even an ongoing contract agreement.
Freelanship is just the beginning. It’s certainly far from the end for these young professionals.

I’ve essentially “made it” for a young person so I’m not doing this for me anymore. I’m doing this because I work with both sides of the hiring fence, and it’s really bleak for both sides.

Everyone has something to contribute to the world. For me, it’s helping solve the economic crisis America is in; helping young people gain valuable experience; and helping employers find and mold talent who fits best with their culture.

That’s it. That’s why I created Freelanship. I hope it helps you, whichever problem yours may be.

What does your typical day look like, and how do you make it productive?

I don’t think I have a typical day besides the fact that I’m typically always working from home, and I’m always editing a few articles per day.

I try to schedule all my meetings on one day of the week or one time span during the day. I try to schedule meetings for later in the day so I can do my deep work in the morning, when I have the most energy.

Days can consist of writing, editing, strategizing, talking, customer support – anything and everything.

How do you bring ideas to life?

Well, let’s start with how I get my ideas. I get my ideas by reading – and reading a lot. Once I discover a problem, I begin obsessively researching it.

Once I have a good understanding of the problem, I begin talking to people about it – conducting interviews, emailing questions, talking things out with friends and mentors.

Next, I begin writing about my ideas and seeing how people react to them. Once I feel there is a need for something I can offer, I build out a minimum viable product (MVP).

In the words of Eric Ries, an MVP is “[the] version of a new product which allows a team to collect the maximum amount of validated learning about customers with the least effort.”

For example, when I first launched Freelanship, it was just a Slack group and Typeform tied together by Zapier. Now, it’s much more automated and less manual, thankfully.

What’s one trend that really excites you?

I’m not sure if this counts as a trend, but I’m really excited about the education bubble because college has been overvalued for way too long and hasn’t been delivering any return on education (ROE) for its students (customers).

I wrote about this in-depth here. Here’s an excerpt I loved from Peter Thiel:

“Higher education holds itself out as a kind of universal church, outside of which there is no salvation. Critics are cast as heretics or schismatics endangering the flock. But our greatest danger comes from the herd instinct that drives us to competition and crowds out difference.” — Peter Thiel

Soon colleges will have to reimburse students for predatory lending. Some already must.

What is one habit of yours that makes you more productive as an entrepreneur?

The Pomodoro Technique, which breaks your work down into intervals. I love the $5 Mac app, Zonebox – a pretty timer that counts down in my menu bar. I also use its sister app, Zone, which tracks my time so I can tally it up and export it into a spreadsheet each week.

I also listen to It helps me maintain focus, when I’m in a noisy place.

Last and certainly not least, I make a habit of reviewing my weekly timing report. Timing is a Mac app that automagically records every single second of your day on your computer so you know exactly where and what you’re spending your time on.

What was the worst job you ever had and what did you learn from it?

I wouldn’t say it was my worst job, but I will say it was my hardest job – waitressing at Houston’s. It took me a month to land the job, and it taught me so many soft skills I still have today, such as how to work well under pressure, how to provide excellent customer service and how to work as a team.

One of Hillstone’s / Houston’s great secrets is that the franchise operates under “team-based” service, i.e. customers are always happy. I’m surprised more restaurants don’t operate this way. It just makes logical sense. I’m also surprised more businesses don’t operate like this in general.

I’ve seen companies offer giant bonuses to individual employees only to make the employees get mad at each other that they were doing “their” job. Beware of doing things that hurt team collaboration and morale.

If you were to start again, what would you do differently?

I would’ve started sooner.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Read, and read a lot.

Bill Gates, the world’s richest man, says he reads 50 books a year.

When asked the role reading plays in his life, Gates said:

“It is one of the chief ways that I learn, and has been since I was a kid. These days, I also get to visit interesting places, meet with scientists and watch a lot of lectures online. But reading is still the main way that I both learn new things and test my understanding.”

What is one strategy that has helped you grow your business? Please explain how.


I guest blog a lot. I used to a lot more, when I was first starting out because that was the fastest way to get traction – blog for places with built-in audiences.

Did you know that guest blogging is how Buffer grew from nothing to more than 100,000 customers in nine months? Well, now you do. Blogging – especially guest blogging — is important.

Blogging is important – especially guest blogging — because it familiarizes people with your name and business; and therefore, associates you as a thought leader in your industry. Just teach people what you know. That’s how you become an authority in your field.

What is one failure you had as an entrepreneur, and how did you overcome it?

I’ve had many failures as an entrepreneur. I think I do the same thing every single time, I mope for about an hour, then I get back to work, and find an alternative solution. No is never the last answer.

What is one business idea that you’re willing to give away to our readers?

I think a dog dropshipping business would do phenomenal because it’s a huge market, and all of the websites are crappy, when you Google for anything related to dogs.

Plus, if even just a sliver of people spend as much money on their dogs as my mother does on her’s online, you’ll have a huge business.

What is the best $100 you recently spent? What and why?

I bought myself a new pair of Adidas because I’m getting into working out again. I love them.

What software and web services do you use? What do you love about them?

A lot of different software and services makes my world go round. But I’d have to say Mailchimp, Revue, HubSpot’s Sales CRM, Email Hunter, Pocket, Highly, Medium and Crystal Knows are top of mind.

Mailchimp: Automated emails
Revue: Curated email newsletter (Super simple)
HubSpot’s Sales CRM: Track email opens and clicks
Email Hunter: Find people’s email addresses
Pocket: Read-it-later app
Highly: Online highlighter
Medium: Blogging platform
Crystal Knows: Learn how to write emails to people you’ve never met before

What is the one book that you recommend our community should read and why?

Agile Talent: How to Source and Manage Outside Experts.

More of the world is heading in the freelancer’s direction; and so I think it’s vital that all leaders learn all the reasons businesses outsource, which isn’t always to find the cheapest overseas labor pool but rather to gain a competitive advantage. Not only the reasons though, they should also have an idea about how to recruit and engage this type of talent, which is different than leading full-time employees.