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Landing your first client is great.

Landing your first client worth $20,000 is even better.

When you’re first starting out, freelancing is far from what you see in shows like House of Lies or Mad Men. The world of freelance is filled with highs and lows with a splash of thrills and mini-breakdowns.

Don’t get me wrong.

Consulting can be very fun and very profitable.

When I was 26, I built my first six figure business doing consulting and work with brands from all over the world. I’ve been placed I never would have imagined and have worked with clients who I’ve been a customer for my entire life.

How did I do it?

That’s a question I’m asked time and time again.

Lots of freelancers are stuck in a situation where they can’t break that six figure mark. Is it because of how you’re pricing your projects? Is it because of how you’re positioning yourself? Or is it because of something you don’t even know?

One of the biggest challenges in consulting is customer acquisition. As we all know, cash rules everything in the wonderful world of entrepreneurship. So when it comes to landing big contracts with consistent retainers with a nice budget, most freelance consultants will do whatever it takes to win.

But how do you land those deals? How do you rise above those freelance jobs for beginners that pay $2,000 or $8,000 project?

Understand The Two Types Of Big Money Deals


There are two different types of BIG money deals for consultants or freelancers.

You can either land a long term commitment project (LTC) or a high impact solution project (HIS). A long term commitment project is one that is spread out over a longer period of time (6 months to 3 years) or a high impact solution project which is an engagement that requires the service provider to come in and solve an immediate problem within a short period of time.

Both are great opportunities but the way you approach them can differ:

Long Term Commitment (LTC)

For these projects, it’s important that you know what you’re doing but it’s also important that you mesh well with the client and team. You’re likely going to be spending a lot of time with them in the coming months so they will want to know that they can trust you, enjoy being around you and be certain that you’ll deliver results. Building a sense of trust and commonality in the beginning will help you in landing these types of projects as they are sort of like hiring an employee but not (if that makes any sense).

Let’s say you’re a graphic designer.

A potential LTC project in this field would be a retainer project in which you’re paid $5,000 a month to deliver a set amount of deliverables every month. It could be a combination of 2 infographics, 10 social media posts and 5 hours of web design. On top of that, there’s a contract in place that highlights that this engagement is going to run over the course of a series of months.

Within 4 months at a monthly fee of $5,000, you would have $20,000 in revenue for your business. Not bad.

High Impact Solution (HIS)

These projects are typically when shit is hitting the fan or something big needs to happen to drive results from an opportunities or challenge. Have you ever watched House of Lies? The majority of the cases that Marty and his pod are tackling would be what I call High Impact Solution projects.

In these situations, clients are less likely to care about how well you work with them from a personal level and are more concerned about how likely you’ll be able to drive results. How likely you’ll be to make them look good in front of their board of directors or the CEO.

Results trump everything in these engagements.

Continuing with the designer example, a High Impact Solution project would be working with a startup whose board is putting pressure on the CEO to launch their product and the product design currently sucks.

The CEO needs someone to come in, wireframe designs, make things beautiful and help them launch their website in a short period of time. These contracts can be high stress but can be very profitable because of the urgency and importance for your client.

The approach to landing these contracts require shown and demonstrated expertise. In this article, you’re going to learn tactics that will help with acquire both High Impact Solution projects and Long Term Commitment projects.

The key is to recognize that relationship driven tactics are more likely to generate long term commitment projects and expertise driven tactics are more likely to generate high impact solution projects. To start, a combination of tactics is the best approach as there is benefit to figuring out what exactly you prefer. Some people like the flexibility that comes with High Impact Solutions while others like the stability of Long Term Commitments.

Let’s get to it…

Relationships Are The Key To Big Money Deals

The stronger a relationship is going into the sales process, the better your chances of closing the deal. This is especially true when you’re looking at a LTC deal. According to a 2014 report from Introhive, 98% of the top sales professionals say relationships are the most important part of generating new business.

So how do you go about establishing a relationship? 

First, stop thinking about building relationships as a daunting task.

The prospect, lead, former colleague or whatever you want to call them is just another person.

Start there.

Now relax. Take a chill pill and understand that the same things that motivate you are the same things that motivate them. We’re all human. Your only objective now is to establish a relationship. To establish trust. To build a connection with the person that could potentially write you a check for $20,000.

So what can you do to be likable? What can you do to gain their trust? Here are a few ideas…

Understand The Art of Conversation


Are you one of those people who think about what they’re going to say next while someone is making a point? If so, that’s the first issue that we need to solve.

Studies have shown that people like to talk about themselves. In fact, the actual act of talking about yourself stirs up an intense level of pleasure for the brain. People LOVE talking about their hobbies, their lives, their relationships and anything that revolves around them. According to the Wall Street Journal:

Talking about ourselves—whether in a personal conversation or through social media sites like Facebook and Twitter—triggers the same sensation of pleasure in the brain as food or money, researchers reported Monday. About 40% of everyday speech is devoted to telling others about what we feel or think. Now, through five brain imaging and behavioral experiments, Harvard University neuroscientists have uncovered the reason: It feels so rewarding, at the level of brain cells and synapses, that we can’t help sharing our thoughts.

As a freelancer, it’s your job to learn as much as you can about your clients business and their objectives. It’s your job to understand their problem and help identify the right solution to fix it. It’s impossible to understand their problem without actually taking the time to ask questions and actually listen.

So that’s what you must do. Shut up. Listen. Take notes and be engaged.

In doing so, they’ll appreciate the fact that you care. For any of you folks who have a hard time actually caring, here are some ways to give your prospect that perception:

Pay attention to their expressions.

Notice when their face lights up with excitement and do the same. If they seem confused or puzzled, adjust your expression to inquisitive or one that demonstrates intense listening.

Demonstrate and bond over commonalities. 

Did this prospect goto the same school as you? Talk about it.
Did this prospect work for the same company as you in 2008? Talk about it.
Did this prospect attend the same concert as you this summer? Talk about it.

Finding things that you have in common helps with building trust and a relationship. Studies have found that the brain has a strong bias towards people who are similar to us. We like people who like the same things we do. We like people who do the same things we do. We like people who are like us.

Find these things and establish a level of connection that cannot be ignored.

Ask good questions.

Don’t go back to high school and ask simple questions like what is your favorite color? Dig deeper to gather insights and information that will help you in understanding them on a human level. Ask them to discuss their day to day or take steps to ask why things are done a certain way.

Question everything.

One of the most important times to ask good questions is in the early stages of a client relationship. It can feel annoying but the potential client appreciates your curiosity and eagerness to understand their situation.

Landing High Paying Gigs Is Like Chess, Not Checkers

Chess Son and Father

The biggest difference between chess and checkers is the complexity.

In chess, the players have to think five steps ahead throughout the entire game to stand a chance. In high stakes games of Chess, the Grand Masters have stated that how you begin the game is more important than how you finish.

In checkers, the game is more in the moment and most moves have a direct and immediate impact. Each piece represents the same value and the strategy is as basic it gets in the world of boardgames.

In consulting, it’s important that you have a chess mindset. It’s important that you understand that every relationship is different and that you’re constantly thinking five steps ahead instead of making decisions for short term gain.

For example, if a potential $20,000 client asks you to spend 2 hours in their office, you don’t have to invoice them for that time. The value you show them during these two hours should blow them away to a point where they’re left asking their team one question:

“Could you imagine how much value we would get if we actually paid?”

Too often do freelancers get stuck in a position where they feel it’s necessary to charge and invoice for every meeting. Instead, you should look at these smaller interactions as a part of the relationship building process and time to build trust. In doing so, you’ll build a relationship that is 10x more likely to last and show your clients that you’re not just after their money, you’re truly trying to help.

Here are a few of the best chess moves you can make to land higher paying gigs:

Send Quality Resources To Leads & Clients

I don’t think this can be overstated enough.

Studies have found that 89% of B2B marketers agree that third-party content is perceived as more credible than branded content & 76% agree that it produces more quality leads.

This means sharing content from other resources is perfectly fine. In fact, it’s often see as being more credible than the content you develop as a consultant on your own.


Because the client is already close to you. The sense of familiarity makes hearing it from someone else worth more. Sharing content from a third party can further establish your credibility or support an idea that was receiving some resistance.

Are you a designer? If so, you want to share content like this:

Are you a developer? If so, you want to share content like this:

And if you’re a digital strategist, you can share content like this:

Share resources to show your potential clients that they’re on your mind and that you’re on top of the latest trends. It’s a great way to stay top of mind and shows the prospect that you’re someone they can rely on.

Create Quality Resources In Relevant Mediums

Curation is great but creation is better.

It’s also more challenging to create high quality resources. The key to creating these resources is first taking a step back and understanding the needs of your customers and leads. It’s about figuring out what they want to learn more about and then taking the time to create a resource that delivers on their need or want.

The resource can take the shape of a variety of different types of content. A few types of content resources that you can create include:

Blog Posts – It’s a tried and tested approach. It might sound boring at first glance but it’s an easy way to create value for your customers and potential leads. It’s also something that exists for years to come and has the flexibility of being shared on social media channels and via email without much challenge.

Presentations – Over the last year or so, I’ve built more than $20,000 worth of Slideshare presentations. I’ve created presentations about Instagram, Sales, Content Marketing and even Entrepreneurship as a whole. I’ve used these presentations to generate leads but also nurture existing relationships by showcasing my knowledge

Ebooks & Whitepapers – These take WORK. If you’re going to be taking the time to write a book, you better be ready to spend some late nights and early mornings behind a keyboard. It’s a Friday evening as I’m writing these words and I could have been out enjoying the sun but instead, I’m writing this. Content of this magnitude require a significant time investment.

Record Your Presentations – Instead of reinventing the wheel, record yourself in action when you’re hosting a workshop or delivering a presentation. Are you talking to a community of designers about the power of typography? Ok, record it. Are you talking about the impact autonomous cars will have on marketing? Ok, record it. Record your presentations, host them on YouTube and share them with your leads & clients.

Research Studies – It’s actually much easier than it looks to become an authority using research. Sure, it’s not exactly Harvard or Stanford quality studies but you can conduct research with your own resources to elevate your reputation as an expert. Whether it’s investing a couple hundred dollars to use Google Surveys or putting in good old fashioned Hustle and using a TypeForm; it’s never been easier to gather information from thousands of people than it is today.

Do Pro-Bono & Charity Work In The Community

It might feel strange hearing that this is a marketing technique but it’s a great way to strengthen relationships. Offering your time to help charities, non-profits and community groups is a great way to build relationships with people who you might not meet under common circumstances.

Show support of the organizations that some of your leads care about. Go to the events where you know they’ll be spending time. Offer your service to school boards or the local Boys & Girls Club. And if you know of an organization that specific leads hold near and dear to their heart, get involved in those through sponsorship or volunteering.

Apply For Industry Awards & Recognition

I don’t really care for awards from an ego perspective. Most people look at awards as a way to give themselves a pat on the back and look good amongst their peers. I’ve been to tons of award shows where people simply want to be congratulated for their work and feel like a king for the 4 hours of glory they receive in the moment.

For me, awards are business opportunities. I could care less about the “feeling” I’m supposed to get when I walk across the stage. I’m more interested in leveraging that award and walk across the stage to open new doors and new opportunities. Don’t allow your awards to go to your head. Allow them to help increase the amount of cash going into your wallet.

Some awards come with money alongside of them. In most cases, the six-figure awards often require the applicants to put in hours and hours of work to win them. The goal from the company or association giving out the award is usually around generating press and driving traffic to their site.

A common approach popping up online these days is the whole concept of “Vote To Win” campaigns. Rather than the award going to the business that has the best product, most traction or most compelling story – the winner is the person who can get enough of their customers and followers on Twitter to vote for them.

The best awards are those that have history and past winners that are respected in the industry. I only apply for awards that have these two stipulations. If the award isn’t respected in the industry or have past winners that are also respected by their peers – I usually pass. Especially if the award requires me to invest (1) capital or (2) time to be considered.

Once I had an award company reach out with great intentions. The committee behind them thought I would be a great nominee for an award and at first glance, I was honoured.

That is, until they told me I needed to “fundraise” more than $5,000 and spend a weekend with them. On top of that, the award wasn’t just for me. It was for 50 other people from a variety of industries that they thought were just as deserving. When I looked at the resumes of those I would be standing with and realized some had little to no qualifications, I quickly had to decline the offer.

It’s just a part of the game!

Public Speaking At Industry Events & Conferences

Public speaking is an opportunity to demonstrate your expertise and knowledge while also making some cash. Foundr too are sure that public speaking is one of the most crucial skills for freelancers and consultants

I’ve said it before. I’ll say it again.

For Freelancers, Public Speaking Is A SUPER POWER!

Not every public speaking will be a paid gig but for those that are, it’s just icing on the cake. Taking on speaking gigs at industry events, conventions and conferences can open many streams of new business. I’ve spoken at everything from Tourism conventions and Real Estate conferences to Consumer Goods events and Restaurant conventions.

There are two key elements to driving business from public speaking events. You have to demonstrate clear knowledge and deliver applicable insights to your audience.

You demonstrate clear knowledge by knowing your craft and showing that in every sentence you speak. You show this by having answers to the questions that attendees ask when the floor is open for Q&A. You demonstrate this by being able to go off script and talk about things that you know your audience will benefit from hearing.

The element of applicable insights should come from the examples, stories and case studies that you include in your talk.

Seek Out Traditional Media Interviews

In successfully landing High Impact Solution projects, you will want to position yourself as an expert in your field. The tactics above like ebook writing, blog post creation and public speaking are great tactics for getting started but distribution is king. What I mean is, your reputation can only go as far as your audience and those you reach. And while “social media gurus” still like to think the medium is dead, Television & Radio are still great ways to establish brand leadership and position yourself as an authority.

What I mean is, your reputation can only go as far as your audience and those you reach. And while “social media gurus” still like to think the medium is dead, Television & Radio are still great ways to establish brand leadership and position yourself as an authority.

I know a handful of PR Consultants who would charge you anywhere from $1,000 – $10,000 to represent you with the goal of landing you a media appearance. In most of these cases, the consultant is actually working as a media broker for a radio show or small news show that charges a fee for a “Sponsored Segment” where the audience can call in to ask questions.

In these situations, your business sponsors the segment and for an hour, listeners call in and ask you questions about your industry or services. As an example, if you run a consultancy with a focus on nonprofits, listeners might call in asking for advice for fundraising activities. You demonstrate your expertise by answering these questions and it allows you to truly be seen as an expert in the space.

Now this is one approach.

It can work well but it’s not my favourite strategy because it usually requires paying a fee.

I’m a believer in appearances that are built on your ability to provide insight on a topic that the media and their audience would find interesting. For example, in the visual you see above, I just finished giving an interview for a local segment on the top apps that everyone needed to download this summer. It wasn’t about marketing but it armed me with the ability to communicate and showcase my knowledge in the digital space. On top of that, I was sure to mention what I did for a living and directed people to where they could find me online.

There is a true art in the subtle pitch. It’s not over the top. It’s not blatant.

It’s phrased like this:

Earlier this month I was working with a client who was about to launch an app that helped pregnant mothers track their meals. I was doing some preliminary research of competition and my jaw dropped when I found [App Name], an app that every parent needs this summer!

See what I did there?

First, I demonstrate that I’m a service provider who helps companies launch apps. This catches the attention of anyone who might be interested in promoting a product launch in the coming months. Second, I talk about my process by sharing the fact that I was “researching the competition,” this gives them a peek into what I can offer. Third, I deliver value to the audience by bringing it all back to the topic at hand, Apps of The Summer.


You’ll find plenty of great resources online about landing your first client.

Some sites will tell you to spend time on job boards or investing heavily into sites like Fiverr or Upwork. While both of these options can put more money in your pocket, big money clients are going to be more lucrative and often times require the same amount of work to lock down and win.

It’s not just about better budgets, it’s about better clients. A client who is already nickeling and diming you for minor tasks is likely a client you don’t want in your roster to begin with. A client that understands your value and doesn’t try to haggle your prices is a client who understands the value you bring to the table and is going to be less of a headache.

Have you locked in clients worth more than $20k? Have you locked in clients worth more than $50 or $100k? I’d love to hear the strategies you’ve learned in your business approach – Comment below and share what you’ve learned!

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Ross Simmonds

Ross Simmonds is a digital marketing strategist who has worked with everything from Fortune 500 companies to startups to drive results using digital marketing and technology.

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7 years ago


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8 years ago

Pretty nice, and from my perspective actionable insight. There is another issue, you probably forgot to mention. Most people have a certain barrier in their mind when asking for a price. If this barrier is not breached, they will never haul the “big” jobs, but will rather be content with the “enough” paying jobs.

Ross Simmonds
8 years ago
Reply to  Elvis M.

Max, great point! You’re spot on with this. Too often do people short sell themselves on what they can truly earn. I think it comes down to being confident in the value you deliver clients. Maybe that’s for another post!

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