How I Escaped The 9 to 5 And Built A $270K Freelance Business By 27

Ross Simmonds
Marketing And Growth Hacking
11 min readJul 3, 2015

I’ve taken a lot of insight from this community and have used many of the lessons gathered here to build my career and launch my most recent endeavour.

I wanted to give back to the community with a post that I hope can inspire anyone who has wanted to try consulting but never made the jump.

Consulting is a job that everyone needs to experience… Even if it’s a short one.

First, let’s rewind back to where it all began.

At 25 years old, I was employed at a small advertising agency for two years and while I thoroughly enjoyed my work, I always wanted to (1) work for myself and (2) have flexibility to travel when I want. I was getting bored with the 9 to 5 and while it’s not something entrepreneurs say very often, I really wanted to (3) make more money. While at this agency, I started my first blog — Here’s what it looked like:

Look, I’m not a designer…

In 2013, I sent in my two weeks notice and was out on the streets as an independent. It was my first year out on my own doing consulting and I earned a little over $160,000 in revenue. For me, this was awesome. I more than tripled what I was making as an employee and couldn’t be happier with the results. At the time, I was terrified that I would be struggling for the entire year but after expenses (my salary excluded), I sat with about $120,000 profit.

At the end of last year, I was able to generate more than $275k in my second year of business as a marketing consultant with a focus on startups and B2B companies. No employees. No office space. And expenses less than $70K.

I’m stating these figures to show you that while I’m not Zuckerberg or Ev Williams, consulting can lead to solid financial freedom even if you’re 27 years old, not living in the Valley and don’t look like most people in tech. The idea of being transparent with figures is inspired by the work of Nathan Barry, Amy Hoy the folks behind Buffer and Pat Flynn.

I’m hopeful my story can inspire and ultimately that the insights below can help you make a successful go at consulting. Here are a couple of the key insights I gathered from my first two years as a digital marketing consultant:

Work With The Right Clients & The Right Partners

At the moment, I’m working on Hustle & Grind, an app called Crate, writing my second book and preparing for a handful of presentations. I would likely go insane if I didn’t have such a great group of people surrounding me and in my corner. I don’t know how to give much advice on this because I really feel as if I’m just starting to figure it out but this diagram sums it up well.

I’ve made mistakes in the past of working with poor clients but I feel I’ve figured it out. I’m now picky with who I work with and solely work with clients who believe in accountability and are not interested in me telling them what they already know.

I’ve stopped responding to RFPs (Request for Proposals) and have a focus on working with B2B, startups and enterprise brands. I make some exceptions when the client has a culture fit but if it’s not something I believe in or an amazing opportunity — I pass it along to others.

Finding the right clients can be challenging. The first thing that most freelancers think they should do is set up a Facebook page and possibly a website to promote their business. If you build it, they will not come. It’s not enough to put up a website and Facebook page and call it a day for your marketing efforts.

As a freelancer, the majority of your work will come from referrals and through word of mouth on the back of clients, friends, colleagues and acquaintances. It’s more going to be important to make an effort to develop and nurture relationships with people in industries and organizations that would be interested in your services.

Here are a few of my most profitable tactics for generating new business:

Say Yes To Great Opportunities Early On

In the service industry, you’re only as good as your last project. If you’re not a freelancer or haven’t worked in service before — your challenge is going to be achieving credibility. If I was to rewind back to my early days of consulting, I said yes to every and any project that came across my desk.

I was young, hungry and had no portfolio. Saying yes to these projects allowed me to build a quality portfolio along with a handful of case studies and references that I could leverage for future business development.

As a freelancer, the majority of your work will come from referrals and through word of mouth on the back of clients, friends, colleagues and acquaintances It’s more going to be important to make an effort to develop and nurture relationships with people in industries and organizations that would be interested in your services.

Look for potential clients who are struggling in an area you can help out in. If it’s something that you can sweep in and provide a quick win — do it! Helping potential clients achieve success early can lead to longer and bigger contracts down the road. And if you’re not already crazy busy servicing your clients; building a reputation and generating case studies at this stage will be very valuable down the road.

Speaking at Events Is Biz-Dev on Steriods

The majority of the events that I’ve spoken at has been local or within a 10hr drive. Public speaking is one of those skills that I truly believe allowed me to separate myself from the competition. I always aim to leave an event as being the speaker that dropped jaws and left people wanting more.

Why you should consider getting in on the speaking game:

New People = New Opportunities

This one is pretty straightforward. The more people you meet, the better chances you will find new opportunities. If you hang out with the same people at conferences, you’re doing it wrong. Do research by looking at conference hashtags before the event and try to follow some people who will be attending. If you see someone using the hashtag that you HAVE to meet — Send them a tweet before the event and lock in some time for lunch or coffee in between sessions.

Personal Branding On Steroids

If you’re speaking at an event, you immediately are considered an expert in a field. As you deliver your presentation, you can either gain more credibility or lose it bit by bit. If you give a captivating presentation that turns heads and delivers value; people will take notice. People will follow you on Twitter, subscribe to your newsletter, ask for your card and associate you with your expertise or industry.

How can you find these events and conferences?

Here are two of my favourite places: and — You can also use the Inbound events tool to find marketing specific conferences.

Write About What You Do — Position Yourself As An Expert

Between 2013 and 2014 I wrote more than 500k words on marketing, startups and technology. It was a combination of guest blog posts, infographics, slideshare presentations and ebooks that resulted in this number.

Writing has been one of my biggest generators of new business, has helped me develop my skills and has accelerated my ability to build a quality network.

Creating content and sharing my ideas on marketing has allowed me to connect with people all over the world and help organizations across the globe achieve meaningful results for their business. Whether it’s through the writings of my recent book or through content published on various industry blogs or seeded in various networks — writing has been a driving force behind the growth of my business and existing network.

Have Strategic Coffee Meetings

Lots of people will ask you for your time; it’s important to take the meetings that matter. When you’re starting out, the coffee meetings you take will make a huge difference down the road. It might be just an hour today but it could be the beginning of a relationship that fuels a portion of your business.

How can you find the right people to meet with?

One of the best approaches I’ve found is surrounding yourself with likeminded people. Attend events and always follow up with them after you meet. Follow up is key. From there, don’t hesitate to reach out when you’re looking for advice or have the ability to deliver them with something of value. When you meet with someone, find out how you can help him or her and then follow up trying to do exactly that.

For example, one of my early contacts said that they were looking for someone who could help with their website redesign. So I sent them a detailed email highlighting how easy it was to use a site like for the design elements along with the emails of 4 contacts I found locally by using dribble and Behance.

Fast forward two months later and they hired me to develop an entire content strategy and work with their designers to build a handful of Slideshare decks and Infographics.

Join Associations, Online Communities or Create A Group

A great way to generate leads and find new business opportunities is to become a member of a professional association or group. Whether you’re a member of a local chamber of commerce, industry association or volunteer on the board for a charity — all of these actions can act as a direct lane to new customers.

If you’re not able to find an association or group that seems relevant to you; create one. Look at what Joel Klettke is doing with The Pitright here on He’s created a place for landing page critique and as a result is associating that space with his brand. It’s brilliant.

I’m a member of 3 or 4 groups on Facebook where the members discuss business and share leads with one another. I’m also a member of 4 different slack channels where entrepreneurs chat shop, the creators host AMAs and collabs happen all the time. I’ve seen people collaborate on projects and even go from contracting each other on the side to joining forces full time.

Check out Chit Chat to find a slack channel relevant to you.

Get The Right Processes & Technologies Behind You

One of the first steps to starting a consulting business is ensuring you have the right processes and technologies behind you. Processes and technologies both play different roles but are the backbone of being able to run a consulting business effectively.

For me, the processes and technologies I leverage daily have played a key role in allowing for sanity, growth and productivity.

Here are some of them:


  • New Business Onboarding: Develop a standard process for the approach you take when onboarding new customers. It could be as simple as sending them a timeline that requires approval followed by the estimate. Either way, having this structure locked down ensures trust in the early days of your business.
  • Standard Project Steps: The best thing you can do for your business is productize it by breaking out each step into chunks. For me, every project starts with “Discovery” which is when I get to know the client followed by “Planning” which is when I develop a plan (obviously) and then “Execution” which is when the creation, delivery or distribution of deliverables takes place.
  • Standard Pricing For Services: No one likes it when you stumble over your prices. Know what you’re worth and communicate it with confidence.


  • Freshbooks for Invoicing: This is a service I’ve been using since I started. It’s a great service that makes it easy for sending invoices to your client and generating reports for bookkeepers and accountants.
  • Slack For Communications: Once you start working with other freelancers, it’s important to communicate. Slack is one of my favorite tools for communication although I’ve also used Basecamp in the past. A combination of these two tools are great for managing your projects and knowing what’s going on.
  • Wordpress For Blogging: This is how you build your reputation as an expert or a homebase that you can drive people to for conversion. No matter whether you’re selling dog walking services or plumbing services; Wordpress has the plugins and themes that will help you create a compelling and engaging site.
  • Gmail (And Plugins) For Email: Sounds simple but Gmail and the various plugins are the key to my sanity. First and foremost, the set up is easy and managing it is a walk in the park. The plugins are the gold mine in my books. While Rapporative isn’t as good as it once was, tools like Boomerang, Canned Responses, Sidekick and my recent favourite: MixMax are amazing.

For me, if just one person can take a few of these lessons and apply them to their life to get closer to financial freedom — I’ve done my job.

While I’m still consulting, my focus is now shifting towards product development — one project called Hustle & Grind another called Crate (Beta testing — Let me know if you want to try it). I’m also writing a book called The Hustle Manifesto: How to Escape the 9 to 5 in 6 Months or less.

All of this is going to be a challenge but one I’m tackling head on to make 2015 and beyond amazing. I’m excited and terrified all at the same time.

There are a lot of more details that I can talk about, but I’ve already written a mini-novel. So it’s probably best that you ask questions and I’ll answer them as soon as I can!

If you have questions, feel free to ask in the comments below or give me a shout on Twitter @TheCoolestCool. Also, if you enjoyed this post, sign up for my newsletter where I share more insights on entrepreneurship, the hustle and insights I learn in this crazy thing called life.

ORDER NOW: I’ve compiled 100 of the tactics I’ve tried and tested to make my first $100k as a freelancer. Let me help you take your business to the next level with these insights. Get it now.

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