In the seventh post of this series, I cast my mind back 20 years to when I co-founded a tech startup …

So there we were. We’d launched our new tech onto an unsuspecting world.

A few early (aka brave) customers were trialling it. Likewise some brave staff members and investors were on board. Here we go!

Did we think the world would suddenly stop what it’s doing and turn to our exciting, new service? The world does not work like that. It’s too busy doing its thing, using the same services it’s been using. Why change?

Startups do not take off on their own accord. They simply don’t. Not even the ones that scale later. They all spend many years in the wilderness, stumbling around the foothills, before climbing the mountain peak.

Perhaps that’s as it should be. For many reasons.

Overnight successes tend not to stick. Slow, organic growth is the one that multiplies, multiples upon multiples, hockey stick style. But before this, come years of travail and learning.

Once you become mind-blowingly successful – if that happens at all – you will look back on these early months and years as perhaps the greatest of times. They may have felt like the worst of times at the time, but later you may look back at their simplicity, their honest hopefulness as the most purest of times.

Scale up

So how do you get those first few customers on board, and grow this thing towards cash flow positivity and profitability?

If you are in the B2B (business to business) world – selling a service to businesses – then cold calling may be part of it. At least initially.

Cold calling. Even the name of it can send shivers down the spine of the most ardent entrepreneur or salesperson. It can make the strongest feel weak, bring on a nervous twitch, and keep many awake at night.

But it has to be done.

I did it. Perhaps you did it. It’s a badge of honour.

Some people seem to love it (“go on, hit me again!” they say as they reach for the next phone number). Most ordinary people would rather endure a severe root canal than have to cold call prospective clients.

Why? It’s probably something to do with the fear of rejection. It’s too personal. Too brutal. Too final. It’s your baby, after all.

It shouldn’t be cold

The first thing to note about cold calling is that it doesn’t have to be cold at all.

Pure cold calling is phoning up a potential customer, out of the blue, hoping to gain their attention, explaining what you have on offer and then trying to convince them to take a meeting with you.

Note – they need to be available to take your call at the precise moment you ring them. Ring them at the office? How and why will you be put through? (“What’s it regarding please?…. Would he/she know what it’s regarding…?” the gatekeeper will ask).

So, call on the mobile (if you can get it)?

No, no, no!

Really – does anyone think this is going to work? That’s akin to walking up to some random stranger in a supermarket and shouting ‘BUY MY PRODUCT NOW!’

Do you really believe that person will be ready to take your sales call, at that specific moment, and then be ready to buy your offering, or at least set up a meeting? What universe are you living in?

So don’t cold call. Not cold anyway.

Do your research, prep the call, make it a warm lead.


Prior preparation prevents p*&% poor performance, as they say.

You would (should) have a list of potential targets. Maybe they are obvious prospective clients. The right type of business, in the right market, location, bracket… fine. At least give them the common courtesy of contacting them first, with a brief (2 paragraph) email or letter (yes, letters can still work) explaining the problems your solution is solving for the potential customer.

Start that first communication with a question that resonates with them. (“Do you need to increase your consulting business leads…?”). Make it plain, short and simple. Not salesy. Honest. Mention that you will be calling in the next few days.

That first communication gives you a hook to start your follow up (warm) call with. (“I sent you an email/letter a few days ago briefly outlining the problem we solve for you, and wanted to see if how we can help you…”).

Don’t give them an easy out. Don’t ask questions with Yes/No answers. Ask open, leading questions. Be calm, authoritative. State facts.

One salesperson I employed used to send a lovely 2 paragraph letter, addressed to the key decision-maker (do the research to find our their name, title, address), and enclosed a tea bag and chocolate frog in the envelope. The letter invited the person to take a break, make a cup of tea, enjoy the chocolate and consider the contents of the letter for a moment.

When the salesperson rang up a day or so later, they would say – to the gatekeeper – “it’s about the letter he/she received this week, just following up on this…”, and when the prospect came on the phone the letter would be mentioned, and if the prospect feigned ignorance (“What letter?”) the chocolate frog and tea bag would be brought up.

“Agh, THAT letter! Yes, I remember…”

A disarming technique, and now the prospect would have a moment to listen to the pitch. The real point of the call would be to make a connection, briefly reiterate the solution and find a time in the diary for a meeting. The eventual ‘pitch’ and ‘sale’ would then take place face to face.

Time consuming? Sure, but great relationships could be forged.

A cold call disaster

I remember cold calling within the first fortnight of the business.

I rang the prospect and launched into my spiel. As I got into my third sentence, hardly stopping for breath, the person interrupted me and said:

“Please stop talking now. If you carry on speaking, I will put the phone down. Email me no more than two paragraphs on what you are selling, and IF I am interested, then I will call you. DO NOT CALL ME AGAIN!


A few learnings here. Firstly, I had not warmed up the prospect. I had called them completely cold. Interrupted their day. They were not best pleased. (Remember, prospects are people too. They might be having a very bad day.)

Second, I had closed off any other approaches to them in the future. I was forbidden from contacting them any more. Not a great outcome.

Third, I had been told off. I felt bad. Memories of reprimands from dark, sarcastic school teachers flashed through my brain. A sharp pang hit my heart. Not a nice feeling.

This hit and miss approach to selling is not only nerve-wracking, it’s inefficient.

Make cold calling a game

As time went on, we hired a sales manager. Three of us – the 2 co-founders and head of sales – took the Yellow Pages (remember?) and divided up our category (real estate agents, in our case) into 3, and would devote an hour a day to cold calling our own lists.

We found that if we did it in the morning, we would be up for it, more energetic, and could pump ourselves up before the hour of calls. Usually between 10am and 11am.

Afterwards, we could get on with our day, and reward each other after the hour was over. We would celebrate if anyone had managed to bag an appointment, and compare notes on how we’d gone. We even developed cheat cards, and would listen in as each of us called a prospect, holding up a flash card if we needed some help.

We made it a game. We had fun. We were calling real estate agents remember, some of the most hard nosed sales people out there. (Strangely, they admired our tenacity, and were rarely rude.)

There’s only positives from cold calling

Another way to overcome any reticence and nerves when making the call is to remember that you can be no worse off after the call than before, no matter what the outcome.

At worst, one more prospective client knew about you and your service. At best, you secured a meeting with a prospective client in the diary.

Even a ‘no’ is never a ‘no’, it’s just a ‘not now’. If we were met with an ardent negative reaction, we would say ‘OK; not a problem; but can we ring you again in three months, and give you an update on how we are going and see if we can help you in some way?’

Who could say no to that? They did not really expect us to ring them in 3 months time. But we would. We’d add that into our database or calendar (what we would call a CRM these days) and it would remind us to ring them again in 3 months’ time. On the dot.

We’d have some fun with it. ‘You said we could ring again in 3 months! Do you have some time in your diary to discuss what we are doing, and whether this could work for you and your business? Since we last spoke, x number of < customers > have joined us….’

From cold to hot

Six months or so after the abrupt (“Don’t call me, I’ll call you”) phone call alluded to above, the person in question walked into our office in Nedlands.

I greeted him with a smile – I knew instantly who he was – and asked if I could help.

“How do I get these properties onto your website?” he said, pointing to the brochures he was holding.

Most of his competitors were already listing on our site, he said. He realised he had to be on there too. His own clients were now demanding it. (Cue: happy dance.)

He had no recollection of the previous conversation (I only brought it up with him many years later at one of our Christmas parties, to which he laughed loudly, apologising if he’d been rude.) He became a client for life. A fierce defender of our site, even when larger, well backed competitors came to town.

Cold (or warm) calling is a badge of honour. Startups probably have to do it. in order to raise money, to win new clients. After a while, it won’t be required anymore. But you’ll look back and smile at a time when it was necessary. You’ll have some scars from it – sure – but you’ll also win some of your most ardent clients and admirers as well.


1. Don’t do it cold – prepare a warm list
2. Contact them first by letter/email
3. Pick a time of day to do it, and do it every day
4. Make it fun, encourage each other
5. Don’t let them off the hook, ask open questions
6. Talk about value, not price
7. Don’t try and sell, just get the meeting
8. Reward yourself after you’ve done your calls
9. Follow up – the no’s only mean ‘not now’
10. Learn and improve your script and calling techniques

Go for it.


Photo by Markus Spiske from Pexels

About the author

20+ years in Perth’s business, tech, media and startup sectors, from founder through to exit, as CEO, mentor, advisor / investor, and in federal and state government. Originally an economics teacher from the UK, working in Singapore before arriving in Perth in 1997 to do an MBA at UWA. Graduating as top student in 1999, Charlie co-founded, running it for 10+ years before selling to REIWA, to run In 2013, moved to Business News, became CEO, then worked on the Australian government’s Accelerating Commercialisation program. In 2021, helped set up and launch The Property Tribune, and was awarded the Pearcey WA Entrepreneur of the Year (at the 30th Incite Awards). In 2022, he became Director Innovation, running the 'New Industries Fund' at the Department of Jobs, Tourism, Science and Innovation (JTSI).

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