Consultant Spotlight: Elisabeth Rosario

Elisabeth Rosario is an independent communications consultant and advisor to startups, consumer brands and venture capital firms.

The Upside: What did you do in your past life before going out on your own?

Elisabeth: Before going out on my own, I was Director of Communications at Spark Capital, a venture capital firm that has backed companies like Twitter, Oculus, Slack, Warby Parker and Cruise Automation. As the firm’s first in-house communications hire, I helped startup founders and the firm's investment team develop and share their points of view. I also led community initiatives with the firm's community of entrepreneurs - building infrastructure, resources and programming to empower and connect over 100 portfolio companies. It was a busy role!

Before that, I was Managing Director at ASTRSK PR, where I played an integral role in the growth of the agency and led media relations campaigns for over 100 disruptive entrepreneurs and startups, including ClassPass, HowAboutWe, HelloFresh, Squarespace, Zola and Academy Award-winning sci-fi film Ex Machina. Prior to ASTRSK, I worked on B2B and B2C campaigns at agencies like Hotwire PR, The Morris + King Company and R. Couri Hay Public Relations. In 2015, I was on Adweek's 30 Under 30 in the PR Industry list.

What's your current elevator pitch?

As an independent strategist, I plug into your team to sharpen your message and create productive conversations that get you noticed. I've worked with startups at all stages to build their brand stories and drive media attention around launches, funding news, product rollouts and profiles. Established brands look to me to develop custom PR campaigns and storylines, to drive awareness, and engage new audiences with a startup mentality. I'll work as an interim head of communications or side-by-side with their head of marketing/communications as a thought partner to help generate an announcement plan and execute on the strategy.

You've been out on your own for a little over a year now. What originally made you pull the trigger?

My employer was suddenly shifting its focus to another city and I decided against making a cross-country move. Once I figured out I had to go, I still wasn't ready to look for another in-house role so I decided to experiment with working as an independent contractor. I told myself I would check in with myself every few months and see if I was ready to go search for a "job" yet and (fortunately) 14 months later I still love being my own boss.

What's been your biggest *win* as an independent contractor?

The biggest win was when I realized I was making a great living and enjoying the lifestyle I wanted, without being at the whim of an employer or manager.

What's been your biggest challenge as an independent contractor?

Running the administrative side of a business is really challenging -- accounting, bookkeeping, invoicing, lawyers and contracts. It does get easier over time (and less scary) but not any less time-consuming. In my experience you either outsource it completely and save yourself the headache, or become an expert in free and paid tools to make it all easier.

What was your biggest stumble and what did you learn from it?

I've made lots of small mistakes which were just as big of a learning moment for me. But two specific examples are:

1) I jumped in so suddenly (like most people do) without a clear plan of where I wanted to be in 6 months to a year. Once things are going well, you have to figure out how, when or if you scale. Almost everyone I know with a solo consultancy reaches a point where they either wonder if they should grow an agency or bring in a business partner. Ultimately you have to think through pros and cons for scaling, what motivates YOU and how making the decision will affect why you're self-employed in the first place.

2) My instincts are pretty good, but there have been times where I've ignored them. I now trust my gut, especially when it comes to deciding which projects to work on. To me, it's important that a client respects me, is fun to work with (fits with my #NoJerks policy) and let's me be the authority or expert on the project.

What do you love most about being an independent contractor?

Getting to spend ALL of my time doing the work I love and NONE of my time on office politics. ;-)

How did you land your first clients?

I reached out to my network and let them know I was starting to freelance. I was fortunate that I landed my first projects quickly.

Who helped you along the way and how did they help?

Former clients, colleagues and friends really helped me in different ways which I'm grateful for, but know I earned over time. I asked for advice on my website, for referrals or Linkedin recommendations (if I felt I deserved it) and for clarity on what services people actually needed.

What do you think is the biggest misconception about independent contractors and freelancers?

For starters, I don't like the term "freelance" for a term used for anyone who is a full-time independent contractor. Having worked for myself for over a year now, I'm an entrepreneur, I'm not "freelancing." I don't think that's great terminology anymore, so I would love to see how things change over the next few years. Some studies show that over 40% of the workforce will be independent contractors by 2020! Culture is shifting and we're all getting used to the indie contractor as a norm.

Second, "freelance or independent contractor" is not synonymous for "cheap labor." Naturally, independent contractors are less expensive than agencies with huge staff and overhead, but don't forget that *you get what you pay for*! ;-) I often advise brands and startups to look for an independent contractor if they have 1) a quick turnaround or deadline for a project 2) a limited budget for a short-term project 3) clearly defined goals and scope of work. A more traditional agency is not typically built to take on these quick, short-term projects since they have to plan long-term and cover lots of overhead costs.

What steps do you think one should take when first starting a consulting career of their own?

(Step 1): Make sure you've built a strong network that sees you as an expert, an enjoyable person to work with and helpful. Nurture your relationships in a genuine way, which usually takes years. Most importantly, don't be a jerk. ;-)

(Step 2): Build a personal website. Make sure it also has some personality that shows you as a human and not just a "professional." Be clear about your services and how you work. Try Squarespace, it's so easy and affordable.

(Step 3): Start taking side projects while at your full-time job. It will give you case studies for solo work and is a great way to get your feet wet and see if working independently is for you. Plus, since you already have a full-time job with benefits, you can be more flexible with the price and scope of projects.

What advice would you give someone who's interested in going out on their own?

Develop a strong network that sees you as an expert. Build a reputation for yourself as a smart, fun and helpful person.

Where do you see yourself in 10 years? What's next for you?

I have no idea what's next for me. Things might be totally different even by 2019! I am really enjoying experimenting right now and I'm comfortable with that.

Anything else you'd like to add for our readers?

Please feel free to reach out if you need advice. I host Office Hours every week, ask me about it!

Follow Elisabeth Rosario's journey:


Instagram: @emrosario

LinkedIn: @elisabethmrosario

Twitter: @emrosario

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