8 sales mistakes I made (part 1)

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In 2021, I hired a sales coach named Amy to help me grow my consulting business.

I hired Amy because our revenue was slumping. If I’m being honest, for over a decade, we failed to hit the numbers we hoped for and believed we could achieve.

Since I “hated sales,” I knew I needed someone objective to help me reframe my mindset and methods.

One of the first things Amy did was audit my past sales calls. She listened for when prospective clients asked about pricing.

I’d whiz through it as quickly as possible. And before the person had a chance to speak, I’d start explaining and justifying. I might even offer them a cheaper alternative.

She called me on it.

I’ll never forget, during one of our coaching calls, she asked: “When it comes time to sell your work, who are you being?”

I thought for a second, “A slimy, desperate used car salesman.”

“Huh!” she continued, “Well that’s something we’ll need to remedy, isn’t it?!”
(said in her lovely British accent)

Years later, I’m still getting comfortable with pricing, marketing, and selling my work. But I can confidently say, I’m light years from the entrepreneur Amy helped to transform.

If selling makes you itchy, today’s post is for you.

I’m sharing 8 sales mistakes I’ve made the past 14 years as an entrepreneur. Many of which you’ve probably struggled with.

I hope they spark a perspective shift, and offer you practical takeaways. Time to start charging what you’re worth, with confidence!

Today’s post covers mistakes 1-5.

In part 2 I cover mistakes 6, 7, and 8.

Here we go.

1. You don’t have to be salesy to sell

The poor used car salesman.

That middle-aged guy with beady eyes, gold chains, and slick backed hair. He preys on unsuspecting customers. He tricks them into buying one of the lemons from his dingy little lot.

He’s the persona that me, you, and every entrepreneur fear becoming.

You draw a line in the sand that you’ll NEVER BE LIKE THAT GUY!!

But then you take it way too far by proclaiming: “I hate selling.”

No you don’t.

You hate the idea of convincing people to buy your stuff. But that’s not selling. That’s being salesy.

You don’t have to be salesy to sell. You feel salesy because you’re not good at selling yet.

You might even feel like an imposter when comparing yourself to other entrepreneurs.

But selling is like any other skill. It takes practice. You’re gonna screw up in the beginning. A lot.

You can be the most outgoing, chatty person in the world. You can be a complete wallflower, or somewhere between. I’ve got news for you, either can become phenomenal at selling. You just need to be willing to learn and refine their craft.

Along the way, the biggest mine to avoid is attaching your self-worth to the many ‘nos’ you’ll get. It’s part of the process.

And if you’re thinking of outsourcing sales to someone else, you’re only delaying the inevitable. As a Founder-Creator, you need to sell your work.

You need to hear the ‘nos’ so you can improve. Not only your sales skills, but your product. Especially in the beginning, while it’s still rough around the edges…

2. You doubt your product’s value

When you first start selling your new product, you'll inevitably face a period of doubt.

You’ll question its value and the impact it has on your customer’s lives. This is not only natural, it’s the reality of creating new things. Every new product has kinks to work out.

The worst thing you can do is pretend otherwise and hope customers still buy. They’ll sniff out your insecurity from a mile away. Instead, own it.

Be honest. Let people know the product is new. While it is, offer it as a discount while you continue to iterate and improve it.

This is exactly the approach I’m taking with my squeaky new Product Bootcamp.

I’m currently talking with a handful of early adopters to co-create the program. They help me solve the right problems, produce the right outcomes, and charge a fair price.

I know the bootcamp is good and helpful. And as more founders go through it, I’ll improve the offer further. My confidence will also grow with the results and what I’m charging (which will probably me a lot more).

Of course, your late majority and laggard customers won’t buy your new thing. It will feel too experimental for their taste.

But your innovators, early adopters, and early majority will be more willing to get in at the ground floor. Especially those who already know, like, and trust your work

Then again… what if you actually don’t hate selling, your product isn’t new, and you still struggle to sell it?

You may be making one or more of the next three mistakes…

3. You only do things that scale

You joined Passive Profits to learn how to build a profitable business that doesn’t run you ragged.

You want to wake up and see that 10 complete strangers bought a product you launched a year ago. No pitching. No sales calls. They clicked and purchased.

This is the dream of building a business that acts like an automated revenue engine. A business that runs and grow, without you needing to sell over and over again. You’ll get there!

For now, to set yourself up for scale, you need to:Do things that don’t scale.

You need to invest in relationships. You need to do a million small tasks, over and over again. You need to put yourself out there without expecting anything in return.

This is the part of the journey that every 7-figure solopreneur before you traveled. You tend not to hear about it, though.

Why? Because it’s completely unsexy work.

Work like:

• Interviewing one person at a time to understand their unique challenges

• Reaching out to learn why prospects said ‘no’ or customers canceled

• Sending personalized connection requests to each new customer

• Writing thank yous to every one of your early adopters

• Crafting individualized pitches to affiliate partners

• Revising dozens of headlines for your ads

• Testing 100 landing page variations

This is the way.

Invest now in the minutiae that doesn’t scale. Then watch your flywheel spin and gain momentum until it’s humming on near autopilot.

4. You have ‘sales calls’

A while back, I had been trying to win business from a VP of a major media company. I tried everything. I connected with her on LinkedIn. I liked and added valuable comments to her posts. I DM’d her. I emailed her, many times. I sent her discounts to our events.

For 16 months, nothing. Nada.

Then one day, I was beginning to tinker on my first toolkit. I reached back out and asked if she’d be willing to join in some research I was conducting.

It was a genuine ask. I suspected she might have experience with the problem I was trying to solve. I hoped to hear her ideas and opinions, before I spent time building a solution.

I was simply doing discovery. The same approach I’d learned and adopted from all my years in tech and product.

She replied within minutes, “Sure, Jay. Send me some times and I’ll see what works.”

Not only did the research refine my solution, but she asked to join our product launch waiting list.

WTF?!

I had been trying to sell this VP a legit service we offered for over a year to no avail. And now, after 30 minutes of research, I had pre-sold her a product that didn’t exist yet?!

This was a MAJOR aha moment for me.

I eliminated the term ‘sales calls’ from my vernacular. I stripped away any and all mentions from our websites, assets, and process playbooks.

From that day on, I never had another sales call; only discovery calls.

Some of my discovery calls remained genuine research interviews to vet new ideas. The rest were calls where we hoped to win business. But not by pitching our services and solutions. Rather, uncovering unmet needs we were capable and excited to solve.

With our reframed discovery calls, our win percentage shot up.

My conversations felt more generative and wholesome. As a result, I stopped loathing the sales process. I was diagnosing problems instead of acting like that beady-eyed car salesman.

The best part? With mounting success, I stopped needing to sell…

5. You NEED to sell

The last mistake I want to share with you today is the one that’s hardest to shake. Because you only start to make it when you near the end of your rope…

As an entrepreneur, I’ve faced many bleak months. Where it looked like we’d have to shudder staff or shut down. Where we were days from running out of cash.

Every company, no matter how successful they seem on the outside, has been in this position… EVERY. Company. (reply and prove me wrong)

During these periods of famine, your creativity shrivels up. Your energy turns an opaque yellow, as your thoughts swell with worst-case scenarios.

You start taking shortcuts. You skip all the activities that don’t scale. You mass email all your contacts. You turn from nurturing and relational to selfish and transactional.

Picture that version of you. Would you buy anything from them? Would you even want to hang out with them?

It gets worse.

When you operate in this low state, you say ‘yes’ to all the wrong things, just to keep the lights on:

• The wrong calls

• The wrong tasks

• The wrong projects

• The wrong partners

• The wrong customers

You do what you need to do. But it’s critical that you shift out the moment you have a blip of breathing room.

I’m not gonna lie, it won’t be easy.

You won't want to hear this, but the best way to get out this hole is to never slip into it.

How? By learning from the mistakes I’ve shared with you today. We ALL make them. Because selling is fucking hard.

But once you start to rock it, I promise, selling will become MUCH more enjoyable. You might even start to love it.

P.S. The lessons you’ll get from part 2 next week are going to build on what we covered today. They’ll also weave in our favorite topic — passive, automated income.

🧑‍💻 Read the online version to leave a comment about today’s selling lessons

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