Hello 👋

Martin here. Welcome to another edition of Founders’ Hustle!

I write newsletters containing actionable insights and insider knowledge across the full spectrum of company building from inception to exit.

Today, I’m sharing the second instalment in a multi-part series of how I closed the initial 10 B2B customers for my first startup!

In case you missed it, here’s:

Part 1: Defining target customers 👥

Now for Part 2…

Approaching target customers 🗣

Practically, it has never been easier to (virtually) reach prospects. Email and social media have reduced outreach barriers to nearly zero.

But, that means prospects are flooded with inbound pitches all the time. You have to stand out in a meaningful way to get noticed.

How you approach your prospects is the tricky part, which is a process that requires ongoing fine-tuning.

At such an early stage, I focused on cold outreach email as the primary communication mechanism. Doing this enables you to contact your cherry-picked targets with laser precision on a completely personal level at every touchpoint.

Before reaching out via email, you first need to produce a list of qualified prospect targets using the framework I shared in Part 1.

Back then I did it manually using Google Sheets. Actually, it was probably Excel, but it makes no difference.

Fire up a new sheet and create different columns for the key details of each prospect — company name, contact name, position, email, phone, LinkedIn URL, notes, etc.

At first, this is going to be blank and look daunting:

So, let’s start populating it.

Your goal is to close 10 prospects. Assuming you convert 5% of prospects into launch customers, you’ll need to add 200 targets to the sheet.

If you’ve honed your ICP really well and your product genuinely solves a major pain point, you can expect to close at a rate considerably higher than 5%. We closed somewhere between 7–10%, I can’t remember exactly.

But, where do you acquire targets from?

Whilst I might use an attractively priced tool to hunt for prospects, I don’t generally buy lists of targets and contacts. Particularly at such an early stage.

Often, there are online databases or networks specific to your market that you can tap into. For example, if you’re targetting:

• Startups: Crunchbase.

• Restaurants/Hotels: Yelp, TripAdvisor

• Influencers: Instagram, YouTube, TikTok etc

You probably know those that are relevant to your market already.

There’s also a ton of business intelligence tools you can use to hunt for targets. The suitability of each will depend upon your market and their price points.

Some have a free trial or freemium model that may be accessible for you to use economically, whilst others are prohibitively expensive.

Import.io and LinkedIn are useful across most verticals.

You can also utilize member lists of industry conferences and regulatory organizations/databases.

Google is usually great for prospecting, too. Don’t just use regular search queries, experiment with these 50+ search commands.

It’s amazing what prospects you can surface for free.

With my first startup, we had a pretty easy time prospecting. Our competitors linked to all of their customers. It was just a case of clicking those links.

Just after launch, we built a web crawler to automate the process. It didn’t take long to make and saved a ton of time

Later on, to find targets not using a competitor offering, we used backlink analysis tools, since websites within the same genre tend to link to each other. Ahrefs is a good example.

Also, prospect yourself. Don’t outsource it.

I’ve found diving into your total addressable market manually, like this, helps develop a much deeper understanding as to the texture of the marketplace you’re entering — the size, shape, and nuances of your target customer base and how your competitors fit into that landscape.

As you prospect, pick out the companies that meet your qualified launch customer profile and put each name into the first column of your spreadsheet.

Keep doing this over and over. Once you’ve got a large enough target list that you’re confident you can close ten launch customers from, it’s time to start populating the rest of the columns with contact information.

The type of people you insert as contacts onto your sheet will depend upon the product you are offering. Generally, it’s pretty straightforward to figure this out. Technical people for technical solutions. Business development people for revenue solutions. Chief of staff for hiring solutions.

But, sometimes, it can be a little nuanced — particularly if your product ‘falls between the cracks’ of positions the company has hired for. My suggestion is to contact those most closely connected to your proposition first and see what response you get.

Also, in larger organizations, multiple roles will have influence over the decision and it may not be clear what seniority level has sign-off or has the clout to evangelize your product internally. Is it the CTO, VP of Engineering, VP of Platform, Head of Backend? etc.

You’ll have to probe several to get visibility. This is not necessarily a bad thing, since it can help you build consensus across multiple levels.

Some market research tools you’ve used may have already provided you with contact details, so go ahead and add the relevant individuals to your sheet. Senior executive names and titles can also usually be found on corporate websites.

If you’re coming up short on company contacts, don’t fret, LinkedIn makes finding them super easy.

The obvious option is to use LinkedIn search. Just enter the company name into the search bar. Here’s an example for Well Plaid, my company:

If you’re not a LinkedIn Premium member or you have no 1st-3rd party connections to the targets you’re searching for, this can be a little inhibitive depending upon the circumstances.

You might get results that look like this, which have no name, just a title:

You can work around this using a handy Google search command.

Enter the name of the company you are targetting and the position title into the search bar, surrounded by exclamation marks. After this put a colon, followed by linkedin.com.

So, if you wanted to find out who the CEO of Well Plaid was, you’d enter this:

Bingo. You have a name and title without having to use LinkedIn.

Now, you should have a few columns populated with data:

It’s time to add the most important contact medium, email address.

Unless your contact’s email address is publicly listed on LinkedIn, Twitter, or a company website etc, you’ll need to do use a combination of digital tools and your own investigative work to get it.

Based on my own heuristics, I generally find the vast majority of email addresses folks use fall under one of the following:

• [email protected]* ([email protected])

• [email protected] ([email protected])

• [email protected] ([email protected])

• [email protected] ([email protected])

• [email protected]* ([email protected])

• [email protected] ([email protected])

• [email protected] ([email protected])

• [email protected] ([email protected])

*Sometimes, an underscore is used instead of a dot.

If your target contact has a name that has common variations, they might be using one of them in their email:

• Daniel

• Dan

• Danny

Generally, though, I find email address names match those used on LinkedIn.

Occasionally, folks use a nickname for an email address.

If their LinkedIn profile says John “Banksy” Smith, they might use “banksy” for their email address.

Another giveaway is their LinkedIn profile URL. If it ends with a nickname, sometimes it's used in their email address.

For example, if the LinkedIn URL is: www.linkedin.com/in/banksy

The email address used could be [email protected].

There are some tools you can use to verify whether or not the email format is correct before sending it. Their accuracy is not 100%, but I found it helps:

MailTester.com (free trial, then paid)

Hunter.io (free trial, then paid)

VerifyEmailAddres.org (always free)

Once you have your email addresses plugged into your spreadsheet, it’s time start your outreach campaign.

For many first-time founders, the idea of selling is uncomfortable.

I had never done real sales work prior to my first startup, and it’s not something that came naturally. But, as CEO, I became head of sales for my new startup overnight. So, I had to dive in and develop that skillset fast.

After all, I had a product I wanted my target customers to use, so I had pitch it to them. Therefore, I had to do sales. There’s no way around it.

At first, I had this false idea that great salespeople were like the characters portrayed by Alec Baldwin in Glengarry Glen Ross, Charlie Sheen in Wall Street, and (retrospectively), Leonardo DiCaprio in Wolf of Wall Street — slick, uber confident, articulate, persuasive, arrogant, charismatic, and fast-talking.

But, I soon realized this wasn’t the case. You don’t need most of these characteristics. Sure, being articulate and persuasive certainly helps, but other qualities make the real difference between closing or not.

Qualities that most founders possess, because they’re a natural filter for becoming a founder in the first place.

As a founder you're authentic. You know your product inside out. You can provide unique market insights. Your passion is contagious. You genuinely care about customer problems. Prospects will feed off your enthusiasm and momentum. You’re pro-active and not encumbered by corporate process. You’ll be relentless 24/7.

Also, prospects don’t expect you to act like a salesperson. So don’t try to, it comes off as awkward. Just be yourself.

They know you’re a founder. Their expectations are different. It’s probably part of the reason they’re speaking to you in the first place.

You’re a resourceful person working on something new and interesting, and they want to be part of that journey. They also know having a founder as a point of contact means stuff gets done quickly.

As mentioned previously, most of our target customer outreach was initiated by email. This is pretty commonplace for early-stage B2B startups.

This was another dynamic that threw me off at first. I had this preconception that outreach meant cold dialling and fast-talking.

Nope. It’s mostly email. So, you better get good at writing engaging, persuasive, and convincing copy.

Let’s dive into that next.

So, go ahead, open a draft email and populate an email address from your target list in there.

Looking at this blank, empty, space can sometimes induce writer's block.

Or, you get an overwhelming flood of the infinite possible combination of letters you could impart onto the screen. Both tend to end in copywriting paralysis.

To avoid this, you need a foundation to work off of. Start by asking yourself one simple question.

What is my objective from sending this one email?

A common mistake founders (and salespeople) make is defining ‘a sale’ as the objective of sending an email.

This puts enormous pressure on a single email and leads to lengthy, one-sided, impersonal, and overly ‘sales-ly’ language because there’s so much ground to cover — team, product, support, compatibility, social proof, case studies, implementation, terms, timeframes, etc.

It loses authenticity and looks exhausting to digest. All of this subject matter should flow over numerous touchpoints. Take it one step at a time.

A major hurdle you have to overcome, is, as a founder, you are encumbered by ‘too much’ knowledge of your team, market, product, etc.

Distilling down all of this domain expertise into a clear, concise, and attractive narrative that your prospects can begin to connect with in the first one or two emails is key.

Practice and hone your elevator pitch. Test it on people not connected to your industry (a family member or a friend). Use simple language that a child could understand. No jargon.

If they can compute the value proposition of your product — and by that, I mean, they are able to explain and articulate it back to you — that’s a decent sign.

The best salespeople are able to distil complex situations into accessible and digestible narratives.

Another common mistake founders (and salespeople) make is defining ‘jumping on a call’ as the objective of sending an email.

Again, I’ve found this is not a great success metric to use. The email copy becomes optimized towards pushing a call for the sake of having a call.

To what end?

When this happens, the call request is awkwardly thrown on at the end of a one-sided cold outreach email.

There’s no real context as to what the purpose of the call is, or, any intent on screening to see if it’s even worth having a call in the first place. This is discourteous to the recipient’s time.

Jumping straight to a request for a call in the first outreach email is usually a sign the email copy is poor. It’s attempting to compensate for that. A call is needed to explain what the email failed too. Again, this is discourteous to the recipient’s time.

It comes across as “can I have 30 minutes of your time to talk about myself?”

I think there’s a misconception that ‘calls mean closes’.

Particularly in the earliest phases of cold outreach.

From my own experience founding and launching two B2B companies, pushing a prospect to jump on a call on initial contact does not increase conversion rates.

Psychologically, it can feel productive to jump on calls in that having real time dialogue provides a sensation of progress. But, it can be unsubstantiated.

If you’re not engaging prospects with your email copy very well, you won’t get many replies. Those that do jump on a call will be less informed about your proposition, so the mismatch rate of incompatibility will be higher. This will yield low conversion rates and a lot of wasted time.

The key to a successful outreach campaign is to put most of your energy into crafting engaging, value-driving, and informing email copy.

Do not underestimate the utility of email.

It’s amazing what can be achieved purely by emailing alone. For the business I’m talking about in this post, I didn’t speak to any of our launch customers on a call. Not once.

That may seem odd, but, they were just happy with the asynchronous low time-burden experience that email facilitates.

Of course, this is not possible for all products. The level of complexity in what steps are required for your customer to understand and adopt your product internally will dictate the degree of interaction required.

The point is, if a prospect is engaged, they will reply quickly and meaningfully by email if that’s their preference. I’ve found that ‘forcing’ a prospect onto a call early on because their email interaction interest is weak doesn’t change their engagement level materially (most of the time).

At my second startup, I had a launch customer who accrued (and paid) over $200,000 in fees over the course of a year and we’d only spoken via email over that entire time period.

Communicate with your launch customers primarily via the medium that is most convenient for them. Not just how you think you should be communicating with them, or, what makes your sales process feel ‘more real’.

If your prospect wants to jump on a call, they’ll suggest it. For larger companies, this is the norm. For smaller independents, many are happy to converse primarily by email and chat applications in the beginning.

So, what objective did I optimize my first cold outreach emails for?

Simple: a reply. That’s it..

My goal was to cold email a prospect and get a response. You don’t even need to pitch anything.

This subtle adjustment reduces the expectations of the email and will make your writing a lot more authentic, engaging, and digestible.

If you get a response, a conversation has started. You can share information in follow up touchpoints based upon the prospect’s lead. Trying to guess all of this upfront in the first email is unrealistic.

Achieving a realistic objective leads to pursuing another realistic objective with the same prospect, then another.

Think of it as setting up a ‘Ladder of Attainable Events’ with each and every prospect. Your cold email is the first step in that ladder. You don’t jump straight to the top (a sale), but work your way up manageably:

This can be broken down further so each phase has its own ladder of attainable events within itself. More discussion on this to follow in Part 3.

But what do you say in your first email?

Don’t send the same email to every prospect. This is way to generic and will look spammy. You need to pass the ‘bot’ and ‘generic salesperson’ tests that aren’t qualifying their prospects before reaching out.

Give every email a personal touch. Write it specifically for the recipient and address them using their name. They need to feel like the email is worth their time reading. That it will generate value.

At this point you don’t need to worry about scaleable customer acquisition, just closing 10 customers, so doing this is manageable and cost-effective.

Conduct research into the company your recipient works for and their background professionally. Check LinkedIn. Run Google searches for interviews, articles, press announcements, fireside chats, podcast appearances, and newsletters, etc. Digest corporate media: websites, social media content, and blog posts.

The fact they are a prospect in the first place likely means you have something in common. Doing this research will naturally create talking points that you would talk about in a real world setting.

Reference what you uncover in your outreach email and try to provide commentary, backed up by proof of why your opinion matters or is relevant.

This creates authenticity in your writing.

Use it as a mechanism to break the ice. Try to provide value: insight, data, feedback—this can be super engaging for the recipient.

This is the give-before-you-get approach. I can’t overstate how effective this can be.

Most cold outreach emails are terrible partly because the sender only talks about themselves and their own company.

By flipping this around you will get noticed. For example, if you are a Search Engine Optimization agency, instead of talking about what services you offer, provide a high-level assessment of your target’s website and a few actionable tips.

Of course, there is one caveat with the opening hook. Your email copy subject matter needs to have an intuitive or logical connection with what you’re pitching.

Switching from talking about 1960s Kaiju films (because you saw a prospect’s tweet on that subject) in one email to AI-driven hiring software in the next can come off as a thinly veiled social engineering attempt.

The skillset and ‘art’ of writing cold outreach emails that get replies is a deep and lengthy subject on it’s own. It takes time to figure it out and is subjective to the market you’re entering.

If you want to fast track your results I suggest checking out this cold email outreach framework I previously shared. It’s designed for use with highly successful, senior ranking individuals.

I’ve used it successfully for years. Now, others are too:

Your email copy should have micro objectives for each section, which should be no more than two sentences each. Preferably one.

In order, they are:

1. Context. (pass the ‘why’ is this person contacting me test).

2. Rapport. (get them to find you interesting, likeable, or valuable)

3. Proof. (why your opinion matters)

4. Call to action. (mechanism to advance to next step)

Below is an example of what I used to write for my first startup. I would do things slightly differently now, but it worked at the time:

Don’t get disheartened if you don’t get a response. Most of us are programmed to interpret silence as rejection. The truth is more complex, reality effects replies.

Your recipient could be in the middle of one of a thousand things when your email hits their inbox. They get distracted, forget, or are just plain busy.

Even critical internal emails sometimes go unresponded too within companies, so don’t take it personally.

If you don’t hear back after sending a first cold email to a recipient, follow up, follow up! Think of it as a friendly reminder to help them acheive their goals.

The response rate for follow up emails is surprisingly high if you do it well. I’ve closed most of my B2B deals by ‘creatively nagging’.

Craft the content of your follow up email so that it’s positive, friendly, and helpful. Your goal is to be engaging. Capture their attention. And, keep it short.

Also, try to avoid boring common phrases that are commonly used. They’re not engaging and the optics do not position you as an innovator.

Avoid using phrases like:

Some folks worry that following up will annoy their prospects and put them off entirely. There’s truth in that — if it’s done discourteously.

It can certainly be a turn off if you overload your emails with common phrases, do zero research on your prospect, email with high frequency, are generally overly pushy in your tone, and provide zero value.

If you’re engaging, courteous, and drive value for the recipient you will look proactive and helpful. Try to talk more about them and not you. Treat it less like a ‘nag’ or reminder and more like a continuation of your first email.

Here’s an example follow up:

Keep following up like this. Again, and again. Be relentless. Each time, gradually drip-feed more detail and convey momentum.

Still no luck? Try contacting more people in the organization. It may be the case you’re speaking to the wrong person.

It’s possible to use tools like Yesware to track email open rates, and by proxy, the level of interest in the email subject you used. I don’t personally— having only ever used replies as the success metric.

Register and use your own domain to email from (not [email protected]). It doesn’t have to be expensive. Prospects will check the domain, so have a basic but attractive and informative website.

You may not have customers yet, but there are other ways to demonstrate credibility on your website: publish screenshots/videos, market research, social proof, and the relevant work experience and educational background of the founders, etc.

The goal is to make the opportunity feel real, imminent, and actionable now. But, of course, don’t mislead on timescales. Use no-code tools like Wix to get a website up quickly.

Link to your LinkedIn profile in your email signature and make sure it’s up to date. Show off personal credentials and experience relevant to your startup.

Also, make sure you have SPF and DKIM records setup for your email account, otherwise, a ton of outbound email could be going to spam.

Check out Part 3: Converting targets into customers 🤝

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