6 Crazy Sales Moves I’ve Made As A B2B Founder

Some worked, some crashed hard!

Hello 👋

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

I write newsletters about entrepreneurship and building startups through the lense of my own experiences launching and growing companies.

Today, I’m sharing a handful of sales moves I’ve made that were pretty “out there” or brazen!

These were made during broader cold outreach experimentation initiatives at the earliest stages of two of my B2B startups. Here we go…

When you’re building a B2B business sometimes you have to go the extra mile to close your first customers, grab market share, or keep the fast-paced growth trajectory up and to the right.

Getting noticed and taken seriously early on is key. Standard channels with low barriers to transmission, like email, are super noisy.

Unless you write a killer cold email, have an existing network to tap into, or have other mechanisms in place to support sustainable growth, it can be hard to stand out.

Even then, it doesn’t always work. “Life”, misconceptions, and edge-case scenarios get in the way.

To overcome this I’ve tried and tested a plethora of different techniques over the years in order to initiate a serious dialogue with a prospective customer.

The techniques were driven by a mixture of naivety, curiosity, and tenacity — some led to sales, some “opened the door”, and some went nowhere.

A bunch of them were a bit “out there” or brazen. I’ll walk you through a few now.

B2B Coupon

OK, so let's start off with a technique that’s a little embarrassing to talk about in retrospect. The funny thing is, it actually worked!

At my first startup, soon after launching, I went on a mad experiment frenzy over a period of a few months. During this time I rapidly tested lots of different cold sales approaches that were quick to setup and execute.

Some tests were conservative, some were bold, and some were…. ‘different’!

One of the tests was a little more “out there” — a B2B Coupon.

It was basically the same promotional tool that B2C retailers like J.C. Penney use to attract customers but repurposed into a B2B proposition, instead of, say, 40% off a sweatshirt or a can of beans. Kind of absurd!

I made a quick template and produced 20 customized versions for target customers. It was very basic! To show you how much so, I dug around in Dropbox and found a copy. Here it is…

I attached the coupon to an email and fired them off to twenty target customers individually.

The intention was to arouse curiosity, so the email copy was light and didn’t give away much. Along the lines of “I’ve attached a special coupon for you to this email”.

A few hours later, one of the targets got back to me!

Within days, after some brief dialogue, they became a customer. Previously, they had ignored me for months.

Even though I thought to try the move, I was surprised it “worked”.

Sometimes it pays to test initiatives that seem counterintuitive or bizarre — particularly if it can be executed quickly and inexpensively.

The coupon basically said what I was previously conveying in emails. I guess the novelty of receiving it provided enough curiosity to open, read, and digest the proposition properly.

Or, maybe just another email alone would have sufficed. Sometimes it’s all about timing.

Champagne List

Another test I conducted during the experiment frenzy was to provide other forms of value outside of the service I was peddling — in an attempt to demonstrate to the customer I cared about their product and broader challenges.

As an example, one of the target customers I was keen to work with owned a website that ran a programme wherein freelance writers could submit guest articles. The content format of the website was specific in structure — curated lists of particular themes from history, science, geography, society etc.

After weeks of cold email outreach not producing any real results, I decided to write a list for the target customer’s website. Since New Year’s Eve was coming up, champagne seemed like a good subject.

I put effort into the research and writing style of the article so that it was in keeping with existing content. Then, I submitted it to the owner.

A reply came back quickly — dialogue established!

It was well-received, and, on New Year’s Day, it was published.

This didn’t lead to a sale, it turned out we weren’t a great fit for them. Fair enough! At least I got an answer and could move on.

A few years later at my second startup, we ended up working with the company.

“I’m downstairs”

This one is old school. Sometimes I’d just show up unannounced at a target customer’s place of business with one of my cofounders.

Not their house. That would be super weird instead of just brazen!

The results of this were always mixed. Sometimes we’d get meetings there and then, other times they would be “busy”, or “not in the office today”.

How this is approached makes all of the difference on the outcome.

For example, we started off by going to the front desk and asking the receptionist to call the target contact directly.

This rarely led to a meeting since the receptionist would usually recite our names and the company we were representing but with no further context.

Since our names and the company we were representing were unfamiliar, without the context as to the purpose of our visit, contacts seemed to be “busy” most of the time.

So, we tried a different tactic.

Instead, we turned up in the general vicinity of their office and fired off an email with the subject line “I’m downstairs”, “I’m outside”, or “Meeting today”.

The content of the email, including a link to our website, communicated who we were. Plus, we’d give some context on the fact we’re only in town for a short period of time and it’d be great to discuss how we can help solve their problems.

Response rates to this were surprisingly high and fast. Sometimes we’d get a meeting right away or within a couple of hours. Other times we didn’t, but, were able to continue the email conversation afterwards — often leading to a scheduled call or meeting later.

We signed some big companies doing this.


Early on at my second startup there was an executive at a target company who we had some initial conversations with and were keen to close. But, he subsequently dropped off the radar and ghosted us.

In the beginning, the gentleman made some comments about where we were based (London) and shared some happy memories of his travels there, including a fondness for a particular brand of British soap that he and his wife liked. It was not available to purchase where he lived.

As the weeks went by and our emails went unreturned we decided to ‘alter’ the communication medium.

Remembering our earlier conversation, we purchased a few bars of the British brand of soap he mentioned, attached a note, and sent it via airmail to his office. Hopefully, it would trigger a response.

Did it work? No.I don’t think we ever heard from him again!

Ah, well. It was worth a shot and inexpensive to try.

Paying customers

At my first startup we paid customers to try our product, as opposed to the other way around! Huh?

Let me explain. After a few months building our MVP the launch was coming up fast. In order for the service to work we needed at least five clients actively using it from day one (minimum critical mass).

So, to get noticed quickly and gain a relatively high degree of comfort our solution would be integrated within a workable timeframe, we offered a one-off ‘install bonus’ to launch customers who integrated our solution fast.

In this instance, it totally worked. We closed above our minimum critical mass target. These customers also continued to use our solution long afterwards, meaning we recouped the install bonus and then some.

The actual ‘install bonus’ cash amounts were also pretty small, relatively speaking. Enough to cover developer costs and demonstrate that we were serious. A moderate risk that’s worth taking when you’re small and doing things that don’t scale.

But, I would not recommend this approach in most instances. For example, if it was a paid service, I wouldn’t have made this move. Switching from paying a customer to use a product to them paying you is a tough shift.

Our product was not a solution that clients paid for with cash. We made money from other means (selling traffic) so it was conducive to the model.

Free (unsolicited) sample

At my first startup, for some time I had been trying to sell traffic (website visitors) to a prospective client. They were difficult to get hold of.

All I wanted to do was set up a test so they could sample our traffic and decide if it was valuable for them or not. I was really keen to find out, since if it worked, the deal would be an exceptionally great match for my business.

If we couldn’t get on their radar through conventional outreach means, I decided I’d try and get on it through their analytics suite — where they measure the audience and monetization of their property.

How? By sending them a big sample of our traffic for free. Enough to make up a material portion of their overall traffic for 2–3 days.

By doing this, my company website would appear as a significant source of traffic in their analytics suite.

I figured if our traffic worked out they’d want more of it and reach out to me. If not, I can move on.

What happened? Nothing! I heard nothing. But, we did hit our target of becoming a major referrer of traffic for 2–3 days (according to third-party business intelligence reports).

It’s likely the traffic didn’t live up to the KPIs they were targeting. Or, maybe, they didn’t even notice or think favorably of our service (for whatever reason). Who really knows — that’s the gamble you take when you make this kind of move!

Investor Intro

At my second startup there was a high-profile target customer we were super keen on working with. They were young, growing fast, and had recently closed a big funding round from a Tier 1 Silicon Valley VC.

We had been chasing them for months. Mostly via email, phone, and via people in our network. Perhaps the odd — brief — encounter at an industry conference.

Our proposition was on the periphery of their radar (at best). The goal was to upgrade this to a considered internal assessment — where they had all the facts and could make an informed decision.

After trying numerous angles, we eventually got a meeting at their head office with three senior decision-making executives.

How? A mixture of sustained outreach and an intro to the CEO through a partner at the Tier 1 VC who invested in them. This was a catalyst for getting taken seriously.

What happened? We took the meeting and discussed our proposition. It led to a considered internal review and a test of our product — but, not a sale. Ultimately, it wasn’t for them.

Although that particular lead didn’t work out, we found the ‘Investor Intro’ approach to be quite effective and repeated it again with other prospects and found success.

Although VCs can be hard to get a response from if you’re trying to raise cash (their inboxes are flooded with pitches), it seems they don’t get as many cold emails regarding existing portfolio companies — which they care about a lot. They stand out.

Approaching with a thoughtful email can lead to a warm intro to a portfolio company you’d like to close. This can carry a lot of weight.

Bottom line: get creative!

Until next time,


Not subscribed to this newsletter? Let’s fix that right now 😉👇