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How I booked my first client with a cold email

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Starting off as a freelancer is terrifying for all who choose this path.

No matter the skillset or area of expertise, there’s always that small voice in your head that debates if this was the right decision.

Just to give you a little background, I freelance in content creation, so I focus on original blogs, inbound content and building sales pipelines for small businesses.

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When I decided to go freelance, I was so pumped about going into the world as my own employer. However, I had absolutely no idea how I was going to go from $0 to enough to maintain my bills.

I took my experience from sales in corporate America and online savviness, and hit the net hard. As my contacts were limited and I wasn’t sure what to do, I tried to be as efficient as possible.

Finding prospects through email was obviously a priority as well as essential to my survival.

Here were the steps I took to book my first client with an email.

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1. I planned and researched a ton

I didn’t just make a list of potential clients; I narrowed it down to a niche where my skills were in demand. I planned on working with local businesses so I went online and got to digging.

I used sites like Timeout and other local curated sites because they act as a local directory and these businesses have already put some value on their web presence.

For this initial prospecting session, I wrote down 50 leads that were local and had their businesses listed in local directory sites.

I took note of their website, social network links, and any contact information that was listed.

2. I ‘creeped’ all their web properties.

I went to them ALL. If they had a Facebook, personal website, Twitter, Instagram, LinkedIn or etc; I made it a priority to review the site.

I reviewed the activity, content, pictures, bio and about pages. I tried to find as many areas of weakness or places that could be improved. In addition, if they didn’t have a certain social network account – for example, Pinterest. I made note of it.

This fueled the need for my services. Any area that needed some improvement was my way into at least a discussion.

3. I organized all my notes and brief evaluations.

I used an excel spreadsheet to keep things simple and straight forward. I made the top tabs with the following titles:

  • Type of Property
  • Facebook Company
  • Number of followers or likes
  • Average update, (Date of last engagement)
  • Area(s) of improvement (Not utilizing hashtags, Not using images with posts etc)
  • Recommendations

This spreadsheet kept me organized if anything with my leads. I already had an initial idea of how to pitch my top prospects before I even made contact.

More on Millo: “A 3 part email series that turns subscribers into clients”

4. I dug up contact information

Now that I was organized, I took the top 5 potential who I felt I could help the most and dug up contact information. I use LinkedIn and Facebook for this type of information.

If I couldn’t find a specific name or email address, I used the general email on the site. If I could find a contact on LinkedIn, I would add them as a Friend (Hack) since most of the time I had no connections to introduce myself.

I added a personal message to make sure I didn’t come off as a copy and paste type of person.

5. I prepared the email

Now that I had the email and contact information – this is where I made the money. Remember the top five prospects, I mentioned earlier.

I drafted a 14 to 30-day proposal on how I can improve their site’s content, blogging, or social media activity based on my evaluation. I formatted this proposal in a detailed PPT. I made sure to answer: who, what, how, and why in this email presentation.

I was sure to not include pricing, because I wanted to peak their interests and if they asked for a price, I knew they were interested to some degree. I did this for the first 4 prospects.

6. I expressed my intention to work on trial

I was always willing to do a trial basis before I even sent the first email. I’ve worked in sales for a long time and I understand that small and medium businesses are bombarded with calls and emails daily.

I wanted to set myself apart and knew that my work would be my selling point. I made it known that I was willing to do a small project or work for 2 weeks as a trial period.

I did this for 4 of the top 5 prospects that I thought I could improve the most. I got 2 email replies and schedule two meetings. The first meeting I had with a local language school and went over the email presentation. I answered a few questions and left.

The following week, I received an email asking for a second meeting with the owner, by the end of the second meeting, we had schedule a start date. I signed a 6 month contract at the end of the 2 week trial period and now going on my 2 contract with that company.

Wrapping up

So that’s how I booked my first client with a cold email. This is from my own experience and using the skills that I thrive in. Take these steps as an outline but you can add your own flare to them.

Each step is as important as the next. From researching sources to drafting initial presentation PPTs, you should have a game plan before making your first contact with potential leads.

Tell me if these steps help with your client prospecting or if you think I can add anything to make these steps better.

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About Deshawn Peterson

Deshawn Peterson is a digital nomad currently living in Shanghai. He specializes in content creation and inbound marketing. In his spare time, he’s studying Mandarin and loves talking about tech, entrepreneurship, global economics, and traveling. Follow his adventures on Twitter and Instagram.

Leave a Comment



  1. Didn’t you first need permission to email them?

    How did you generate your email list?

    • I researched on a lot of websites and dug through the contact/about us pages. These usually have generic email but sometimes you’ll strike gold with a personal email.

  2. This is great advice, Thanks Deshawn. Happy travels!

  3. Hi Deshawn,

    I appreciated your article and found some helpful take-aways but I did want to clarify something:

    You began with 50 potentials and researched all of them, then you narrowed in on 5 and ultimately got 1 contract, is that right?

    My observation is that conversion can still be pretty low.. I guess that’s just the nature of the game?


    • Yes it’s a pretty low conversation rate but I would consider how much revenue is being generated from each conversion. Since then that one conversion has grown to more just through referrals. I started with 50 and dug through linkedIn, Facebook, and other channels to identify areas of improvement immediately.

  4. I generally don’t recommend outreach, but man THIS is how it should be done.


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