How I Closed $12,030 with Cold Email, and What Has Changed

In the first seven months of my freelance career, I closed $12,030 of business from a few batches of cold emails. I published those figures in July 2014, when I was building websites and had only a few clients. In my earlier creative ventures, some deals with Fortune 500 clients had also started with a cold email.

I wrote this playbook that July to show how it worked. Its core still holds: one relevant case study, a short list of prospects who look like that client, an email that proves you looked at their business, and one follow-up. The setting around the email has changed. Google, Yahoo and Microsoft publish sender requirements for their consumer email services, anti-spam law in the US and Canada sets requirements this playbook never mentioned, and the open tracking I relied on tells you much less.

This page keeps the 2014 method and my figures from that time, and updates the parts that changed. It is for a founder or a small agency deciding whether cold email can win its first clients, and how to run it without damaging the sending domain or the relationships.

Step 1: Choose quantity or quality

There are two ways to approach cold email.

The quantity approach treats it as a numbers game. In 2014 I recommended it for most new freelancers: email at least 100 prospects and expect to close one or two medium-sized jobs.

The quality approach focuses on your 25 ideal clients, the ones where one or two deals would pay for your entire year. I suggested it for experienced creative professionals and agencies with a large portfolio.

My own advice moved toward quality. By 2020 I was running Lead Cookie, an outbound prospecting business I built and later sold, and I wrote that "The market demands lower-quantity, higher-quality, outreach." In an April 2020 post on the outbound industry, I suggested breaking a list of 5,000 prospects into 10 batches of 500, each with its own more relevant message. Instead of every CMO at a company with 11 to 50 people, write to the CMOs of cybersecurity companies that size in Boston. The same post said this did not mean personalizing every single message; the relevance came from the segment.

If you are starting out, the steps below work at either scale. Keep each batch small enough that every email can say something specific about the person who receives it.

Step 2: Build a case study before you send anything

Before you send a single cold email, you need a relevant case study. Without one, most of the time and effort you put into the emails goes to waste. If you have not finished a client project yet, start with your existing network: in 2014 I suggested asking people you know for a meeting, finding out what problems they have and asking for paid work. Then turn a successful project into your first case study.

A case study is a short success story from one client. It covers five things:

• Who the client is
• The situation they were in when you met
• What you did for them
• The result
• A testimonial in the client's words

Keep it to one page, however large the project was. Prospects skim case studies, so a short one does the job and a long one wastes your time. I packaged mine as a one-page PDF that I could attach to an email or a proposal. A page on your portfolio site works too, and so does a video of no more than two minutes that covers the same five points. Presentation matters, because the prospect judges the quality of the case study along with the project it describes.

I suggested keeping two or three case studies on hand, so you can send each prospect the one closest to their situation.

How to get the testimonial

Ask for it. After a project goes well, email the client and ask whether they would write two or three sentences about working with you.

If they are busy, draft two or three sentences from their point of view and send them over to approve, change or scrap. The FTC's endorsement guidance says that "endorsements must reflect the honest opinions or experiences of the endorser" (opens in a new tab), so use only words the client agrees describe their experience. In 2014 I also recommended putting a photo of the client beside the testimonial, to make it more believable.

Step 3: Email prospects who look like your case study

Relevance is the most important part of a cold email campaign. You cannot email anyone you like and expect enough volume to produce sales. Target prospects whose situation resembles the client in your case study:

• If you are reaching out to trade associations, you need a trade association case study.
• If you are reaching out to chiropractors, you need a chiropractor case study.
• If you are reaching out to personal trainers, you need a fitness case study.

When the case study shows a happy client who was once where the prospect is now, the prospect can connect the dots. Without that connection, the offer comes across as a generic sales pitch.

I learned this the hard way. I once targeted a niche where I had no portfolio pieces or experience. After 125 emails, I did not get a single response.

The opposite happened when I was starting my web design business. I had just built a website for a local trade association, and I realized there were 49 similar associations in other states. I researched them and emailed roughly 30 that looked like they needed help. Two hired me for a website and put me on a retainer as well. I wrote about that campaign in The Secret Ingredient to Direct Outreach.

Step 4: Build a researched prospect list

You will rarely find a spreadsheet of potential clients with their details neatly organized. Trade organizations and industry directories are the usual starting point, and they often list at least a phone number and a website.

For each prospect, look at their website and answer three questions:

1. Does this look like a potential client?
2. Is there an email address anywhere on the site?
3. Does the site name the people who make the purchase?

If the answer to the first two is yes, add the prospect to your list. If the third is yes as well, note the buyer's name so you can write to them directly. Before you send, check the laws that apply to you and your prospects, the sending policies of the providers involved, and whether their site says they refuse unsolicited messages. A published email address alone does not establish consent.

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Jake’s historical account, summarized from this article. These results describe his experience and are not a performance forecast.

This research takes time, and in 2014 I suggested hiring a virtual assistant on oDesk or eLance to do it. Both sites became Upwork, and their addresses redirect there.

Researching the list also keeps you away from bought lists. Google's guidelines for sending to Gmail accounts put it plainly: "Don't purchase email addresses from other companies." (opens in a new tab) The next line goes further and tells senders not to email people who did not sign up, because they may mark the messages as spam. Relevance does not turn an unsolicited email into a requested one. Google's guidance applies to personal Gmail addresses.

Step 5: Write an email that shows you did the research

One ground rule first: never copy and paste a blanket statement. Every email needs details that are specific to the prospect and their current situation.

This is the email that won me a $4,250 website client, as I published it in July 2014. The brackets mark what I filled in for each prospect.

[Prospect names],

Recently I came across [Company name] in the [Directory where I found their information] and I wanted to reach out. My name is Jake Jorgovan and recently I finished up a website design project for [case study client] and wanted to reach out to similar companies.

When I came across the [Client's website], I noticed [review of 2-3 things that I found wrong with the clients website]. With the [case study client], we were able to build a professional site and get it up and running in under three weeks. Their site is mobile friendly and extremely easy for anyone at the company to update.

If you are interested in rebuilding your website, please let me know and we would be more than happy to help you out. Also, I have attached a case study for [Case study client] with a raving testimonial from the owner of the company.

Thank you [Prospect name] and I look forward to hearing from you.

The most important part is the second paragraph: two or three specific things you noticed about the prospect. As a web designer, I could review problems with their website. A copywriter, an illustrator or a marketer will look at something different. Whatever your field, that paragraph has to show that you did your research and that the email was written for this one company.

The 2014 email has no postal address and no opt-out line. US law asks for both in a commercial email, along with a clear signal that the message is an advertisement (the rules are in the last section of this page). A version for today keeps the structure and adds them:

For US commercial email, keep the opt-out working for at least 30 days after you send. Canada's law requires the unsubscribe address or page to stay valid for at least 60 days. Carry the same contact details and opt-out line into the follow-up. If Gmail has classed your domain as a bulk sender, a reply-based opt-out is not enough for marketing email to personal Gmail accounts. Gmail requires one-click unsubscribe headers and a visible unsubscribe link, and it lists requests not honored within 48 hours among the reasons messages fail its requirements.

Step 6: Follow up once

I sent one follow-up 7 to 10 days after the first email, with a short note like this one:

[Prospect name], I wanted to send a quick follow up to see if you received my e-mail from last week in regards to your new website design. Please let me know if you are interested and I look forward to hearing from you.

I was consistently surprised by how many replies that second email brought. People often ignore the first email. A second one tells them you are a real person who wants to help.

If a prospect did not respond after the second email, I found they usually were not interested or not ready to buy, so I stopped there. When someone asks you to stop, stop: the law sets a deadline for that too.

Step 7: Decide how many emails you can sustain

In 2014 I was honest about the numbers: I expected roughly 100 emails to close one or two jobs, and a relevant offer with a complete case study improved those odds. Treat that as the scale of my early test, not as a forecast for your campaign.

Once the research was done, I could send about 25 emails in two to three hours. My goal was 25 emails a week for about a month. Then I took a break, because otherwise I burned out.

Those volumes are tiny next to the thresholds in the mailbox providers' rules. Gmail's bulk classification starts near 5,000 messages to personal Gmail accounts within 24 hours, and Microsoft's Outlook.com rules target domains sending over 5,000 emails a day.

Step 8: Keep track of every conversation

In 2014 I ran everything from Gmail with two plug-ins. Yesware tracked whether prospects opened my emails and reminded me when someone had not replied. Streak was a simple, free CRM inside Gmail, essentially a spreadsheet of prospects with a few extra features.

Both still exist, in a different form. Yesware's pricing page (opens in a new tab) lists a free plan with basic open tracking and paid plans above it, and the company describes its product as sales engagement software for Gmail and Outlook. Streak (opens in a new tab) now sells its Gmail CRM on paid plans and offers free email tools, including tracking and a mail merge limited to 50 emails a day (both pages read in October 2026).

Open tracking tells you less than it did. Apple's Mail Privacy Protection, when a user turns it on, "prevents senders from seeing if you've opened the email message they sent you." (opens in a new tab) Count replies and booked conversations instead. At 25 emails a week, a spreadsheet with the date sent, the follow-up date and the reply is enough.

What to expect

Long sales cycles

If you need cash tomorrow, cold email is the wrong tool. It is an investment, and it can take a long time for a prospect to become a client. My cold email sales generally took two to four months to close. One prospect ignored both of my emails, then wrote five months later to say they loved the email and needed help with a new website.

Sometimes the prospect is a good fit and the timing is wrong. In my experience, the buyers who respond to these offers tend to be extremely busy or slow-moving.

Use it alongside steadier sources

Cold email brought in solid revenue for me, but it was never my most stable source of work, and some months it felt like luck. Treat it as one source of clients, never the only one.

In 2014 my steadier source was oDesk, now Upwork, where within a few weeks I was earning $1,000 to $1,300 a week from small projects. Upwork's freelancer service fee (opens in a new tab) ranged from 0% to 15% per contract in October 2026, and proposals cost Connects (opens in a new tab), tokens whose number varies by job.

Other work then came from my existing network, referrals from past clients and partners such as Squarespace, which sent me a large number of leads for web design projects. I spent about 30 minutes a day on marketing and prospecting, and over time that added up to a steady flow. Some of my cold email clients also referred me to other prospects after the job, which led to sales beyond the first project.

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Jake’s historical account, summarized from this article. These results describe his experience and are not a performance forecast.

Burnout

Nobody dreams about cold email. If you focus on it for too long, the number of emails and prospects to keep up with becomes overwhelming. I suggested trying 100 emails first and then taking a month off.

What still holds, and what has changed

What still holds

Relevance. In November 2014 I called it the secret ingredient of direct outreach, and in April 2020 I wrote that "personalization and relevance will always prevail." A case study from a similar client, a few specific observations about the prospect and one follow-up still do most of the work.

Mailbox providers have written down their rules

In the same April 2020 post, I wrote that cold email deliverability had dropped sharply during 2019. A new email account needed at least a month of warming up before it could send campaigns, and Gmail and Outlook were not going to "lighten up" on their spam restrictions. Since then Google, Yahoo and Microsoft have published their requirements.

Google advises (opens in a new tab) keeping the spam rate below 0.1%, and said that from November 2025 messages failing its requirements would see temporary and permanent rejections.

The providers also advise against unwanted mail. Google tells senders not to email people who did not sign up, Yahoo asks senders to verify they are mailing only users who "specifically requested it", and Microsoft asks senders to ensure recipients have consented. Authentication helps a receiving server verify who sent a message; it does not give you permission to contact anyone or guarantee the inbox.

These rules govern mail to consumer addresses, and their strictest parts apply to bulk volumes. A campaign of 25 emails a week adds little volume, but the domain you send from may already qualify as a bulk sender. Gmail counts messages to personal Gmail accounts across the same primary domain and its subdomains within 24 hours, and once assigned, its bulk-sender status is permanent. The rules are still a sensible floor for any domain you send from. Google recommends that every sender set up SPF, DKIM and DMARC, and Microsoft says all senders benefit from them. Set them up before the first email, keep complaints rare and make it easy to opt out.

The law covers one-to-one business email

The 2014 version of this playbook did not mention the law. In the US, the CAN-SPAM Act (opens in a new tab) covers every commercial email, not only bulk mail, and the FTC states that it "makes no exception for business-to-business email." Its compliance guide lists what each message needs:

• Accurate "From", "To" and "Reply-To" details that identify you
• A subject line that reflects the content
• A clear disclosure that the message is an advertisement, for which the law allows "a lot of leeway"
• A valid physical postal address
• A clear way to opt out, which must keep working for at least 30 days after you send
• Opt-out requests honored within 10 business days

The FTC puts the penalty at up to $53,088 for each email that breaks the law (its guide, read in October 2026). CAN-SPAM does not require consent before the first email.

Canada's anti-spam law (CASL) (opens in a new tab) does. A commercial email needs the recipient's express or implied consent, and it must identify you, give contact details and include a way to unsubscribe that you act on within 10 business days. The contact details and the unsubscribe address or page must stay valid for at least 60 days after you send, and if you rely on consent, the law puts the burden of proving it on you. Implied consent (opens in a new tab) covers an email address the person has conspicuously published or caused to be conspicuously published, without a statement that they do not want unsolicited messages, provided your email is relevant to their business role. On that route, relevance is a legal condition as well as good practice.

In the UK, the Information Commissioner's Office says (opens in a new tab) you can email companies, limited liability partnerships and government bodies. Sole traders and some partnerships count as individuals, so a new contact among them needs to have specifically consented. Every message must identify you and give a valid address for opting out, and the ICO says data protection law may also apply when you email a named employee's address. The ICO notes that this guidance is under review.

This is a summary of what the regulators publish, not legal advice. Check the rules where your prospects are before you send.

Easy tools filled the inbox

Andrew Chen described the pattern in the law of shitty clickthroughs (opens in a new tab): "Over time, all marketing strategies result in shitty clickthrough rates." Cold email followed it. Sending tools and courses of "proven" scripts made volume easy, and by 2020 I was describing inboxes flooded with spam. As I put it then, "every marketing tactic is great when it starts, but then everyone starts doing it and people become immune to the tactic." A message that could only have been written to one person still stands out.

If you have one happy client today, which 25 companies look most like them?