"I fear not the man who has practiced 10,000 kicks. once, but I fear the man who has practiced one kick. 10,000 times." -Bruce Lee.

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11 years ago we were sitting at $0 in ARR.

We couldn’t even spell ARR at the time, but we knew we wanted to grow.

We were looking to find some “enterprise” companies to buy our product but we were getting nowhere after the first two months. Then our CEO gave me a book to read that changed how we thought about prospecting to enterprise-sized companies and it changed our business.

Within 18 months we hit $1MM in ARR.

The book: The Ultimate Sales Machine by Chet Holmes.

Chet Holmes was the Head of Sales for Charlie Munger many years ago and chronicled his experience in what I believe is the greatest sales book of all time.

The strategy is simple: Go after your most valuable sales prospects (Chet calls them the “Dream 100”) with a methodical discipline. Set the prospects. Set the prospecting sequence. Execute every week, without exception.

Chet explains: “Building a sales machine is not going to be about doing 4,000 things; it’s going to be about doing 12 things 4,000 times each.”

That’s the key to prospecting into big accounts, you must be disciplined through the entire process. This includes which companies you target, the message you use when targeting these customers, the methods you use to connect with them, and the consistency with which your repeat these actions.

If it’s so simple, why don’t more sales organizations follow this method?

It may be simple, but it’s not easy. Most give up after a week or two. You have to commit to this for AT LEAST 6 months. The longer you run this prospecting motion, the more enterprise opportunities you will have for your business.

You’ve heard before that sales is a numbers game. Get exposure to the prospect and you will have your foot in the door.

“The goal of the Dream 100 is to take your ideal buyers from ‘I’ve never heard of this company’ to ‘What is this company I keep hearing about?’ to ‘I think I’ve heard of that company’ to ‘Yes, I’ve heard of that company’ to ‘Yes, I do business with that company.’” - Chet Holmes

So how do you apply this to your own business? Let’s walk through the process step-by-step:‍

1.Target the right companies‍

“The fastest way to grow any company is to focus a special and dedicated effort on your dream clients.” - Chet Holmes

Whether you are selling into a big market or small market, there are likely a handful of companies that control a significant portion of the spend. This Dream 100 campaign is designed to capture the attention of your largest prospective clients.

I’ve written before about TAM, SAM, SOM, which you can read here. Your campaign should be focused on the Serviceable Obtainable Market, or the companies that you can sell to today and who will get value out of your product or services.

Putting your target list together is tedious and specific. You should scrutinize every company on the list, each should be deserving of the attention that you are about to give them.

Work through your list until you have at least 50 target accounts. Get as close to 100 as you can.

This is not a list of companies that you think might be interested in your product, it’s a list of companies to which you know for certain you can deliver value.

With each company, you should identify two individuals that fit your buyer persona. It’s best to go as high up in the organization as reasonable. The CEO of a $1B+ company is unlikely to give you their attention, but the SVP of Marketing needs to deliver outcomes and is a much more suitable target for this effort.

For each contact, you must gather the name, title, phone number, email address, and mailing address. Do not forget the mailing address, this is critical to the success of the campaign.

Targeting the right contacts at the right companies is the most important element of this campaign. Do not cut corners here.‍

2. Get the message right

“The one who gives the market the most and best information will always slaughter the one who just wants to sell products or services.” - Chet Holmes

Every interaction with a prospect should deliver value. Remember that your prospect is drowning in emails, voicemails, slack messages, zoom calls, in-person meetings, and so much more. You have to separate yourself from this noise and get the prospects attention. But how?

Remember that your customer doesn’t care about you, your company, your product, or any of the accolades that you have received. The prospect only cares about what you can do for their business.

Most salespeople think that the value is delivered when the customer starts using the product or service. This couldn’t be more wrong.

You can deliver value in every piece of communication with the customer.

Every buyer goes through the stages of awareness. Assume that your prospect is “unaware” that they even have a problem and it’s your job to educate them.

Start by educating the customer on the problem in the industry. Help them understand that they are not alone in experiencing that problem. Illustrate the “city on the hill” or the desired outcome that they will experience when they address the problems in their business.

Write a letter to your prospect that positions your company as an expert on solving the problems. Use research and anecdotes to show the customer how the problem is affecting their business.

This letter will become the foundation of your sales outreach. You will use this letter to write cold emails, call scripts, and other outreach designed to engage the prospect.

The purpose of the Dream 100 campaign is to get you into a meeting with the prospect. Do not expect the letters, emails, and phone calls to fully educate the customer on your product. You are only looking to educate the customer enough to get them interested in learning about solutions to their problems.‍

3. Build your prospecting calendar (don’t forget direct mail)

Now that you have your sales letter, your cold email template, and your call script, it’s time to add the most important part of the cadence: sending a bubble-mailer envelope by USPS directly to your prospect. Include a hand-written card and something physical like a fingernail clipper, a pen, a toothbrush, or a carabiner. Adding this touchpoint will separate you from every other company that’s vying for the attention of your candidate.

I recommend keeping the cadence simple, something that you can stick to every week for the next 6-12 months (and possibly longer).

The goal is to touch each prospect once per week, every week, indefinitely.

Here’s a great sample cadence:
Week 1: cold email

Week 2: phone call

Week 3: bubble mailer

Week 4: cold email

Week 5 phone call

Repeat that 5-week cadence over and over for 6+ months and you will convert cold prospects to warm sales meetings.

4. Put the show on the road

We have our Dream 100 list, we have our sales letter(s), we have our prospecting cadence. It’s showtime.

The key is that you have to stick to it. Every contact on your list gets a touch every single week, no matter what. You can use automation to make this process easy to manage. You can outsource some of the work (like packing the envelopes and sending the mail) but you must be the person reaching out on behalf of the company.

Every touchpoint is meant to set up a phone call so you can do proper discovery by leaning into the problem that you solve.

When you get your first meeting, start by leaning into why the customer took the call. They may say something like “you sure are persistent”, and they would be right because you ARE persistent. Tease out what is most important to the prospect, what they are trying to fix, accomplish, or avoid in their business. Once the prospect has recognized their need, get to work connecting their needs with the solutions that your company provides.

Commit to this campaign for at least 6 months

So now you have it. You know exactly what we did to go from $0 ARR to $1MM in about 18 months. There’s no trick or shortcut. It’s just sales. Consistent, persistent, disciplined.

This will work for your business if you do it. You can’t really fail if you commit to the outreach and you stick with it for a long time. You could run this same campaign for 10 years, updating the language in your sales messaging to fit your business as it evolves and updating your prospecting list as you close more and more customers.

At scale, you will have reference-able customers to make warm intros and case studies to further educate prospective customers on the challenges they may be facing. Until you have scale, roll up your sleeves and start prospecting like clockwork until you get your first 5 dream customers.