If at First You Don’t Succeed, Maybe You Just Suck – and Why Leverage Beats Skill in Sales

Intro

Welcome to my weekly newsletter, Iterations, where I discuss random thoughts, ideas, and stuff from my trials and errors that might hopefully be useful to one or two others.

Quote of the Week

“If at first, you don’t succeed, maybe you just suck.”

Kenny Powers – Fictional Baseball Player from Eastbound & Down

I didn′t have a quote in mind this week, then I watched the hilarious outtakes of the US comedy show Eastbound and Down again.

So that's your quote this week, you′re welcome!?

It′s February and we are being aggressive in attacking our goals this month, so if you are going to do something, get it right the first time and try not to suck at it!

I jest, of course, I mean this newsletter is called Iterations after all! So of course, I believe in trial and error, but hey If you can get it right the first time around then why the hell not?

Behind the Scenes (Projects and Thoughts)

(In Sales) Leverage > Skill

This week I have been thinking about the effect of leverage over skill in sales.

What do I mean by leverage, you can have all the sales skills in the world but if you are selling a product or service that few people want then you are participating in an uphill battle.

Does that mean you shouldn′t work on your sales skills? Of course, it doesn't and you should always aim to fine-tune your abilities.

However, as an employee in sales, it’s unlikely you have that much control over product-market fit, so in my mind, the following three pillars are something that you should be acutely aware of:

1. The demand for the product/service of the company you work for.

2. The timing of joining.

3. The territory you sell in.

You want to shoot for three out of three to have a hope of gaining the most leverage: a) high demand for the product and service, which always helps to have some brand power behind you, b) joining the company early enough to avoid lead saturation and to gain a shot at the best opportunities, and c) operating in a territory that is straightforward to do business in. Do you want to be the Account Executive for Software Sales in Antarctica, for example?

If one of the three is wide of the mark, it’s not entirely the end of the world, but if you can find a company where all of these are flowing nicely, well, then you can ride that wave. I have met amazing salespeople working at companies where none of these three aspects line up, and therefore their chances of making money suffered as a result, conversely, I have met mediocre and even terrible salespeople making good money because they were able to apply leverage in this way.

Food for thought if you are a job seeker in sales right now.

If you run your own company, well, you still have to think like a salesperson at times as well as an investor and operator:

? Do people want what you are selling?

? Are we too late to market and therefore will struggle to compete with the A players?

? Are we focusing on the right markets?

What I’m Experimenting With

I guess you could say that my main experiment this year is with writing, manifesting itself currently in the following guise:

A weekly newsletter that's this one - Iterations Newsletter

A monthly blog that's this one - Latest Article on Fear of Flying

I’ve learned a ton so far, and I expect to learn much more with every quarter that goes by. Not only does writing these regular works push me forward in my transition from consumer to creator of content, but it also helps me tidy up my thoughts into concise sentences. Through newsletter and blog writing, I am slowly learning about organic marketing too, which might come in handy one day as an entrepreneur.

With the weekly newsletter, the first couple took me close to two hours to write and edit. Now, in a matter of weeks, I have got the process down to just over one hour.

Behind the scenes currently looks like this:

? Write a first draft.

? Take a break, come back, and edit it.

? Publish.

I’m sure as I go on, I will get this process to run much tighter. To me, a newsletter is not meant to be a literary marvel, and the self-imposed confines of an hour in which to write it are a helpful limitation.

As for my blog, well, my aim there is to share deeper thoughts or interests, most recently, opening up about my fear of flying, which you can read here. All I can say is that I am enjoying the process, which counts for a lot.

Some of my stats so far:

Writing on Medium

The below image shows my blog articles in order of Most Read. Very cool to see people reading some of these pieces that I put a lot of work into. A lot of people are interested in learning Spanish it seems.

Linkedin Stats

Last week's newsletter received the following impact and it′s interesting that LinkedIn uses the wording vies and not reads.

Podcast/Video Recommendation

2025 GO HARD MINDSET - David Goggins Motivational Speech

I know, some might consider this kind of stuff to be very cheesy, and I get why you would say that, but man, does it help me push myself in the gym. Listening to those almost superhuman people like Goggins talk about running ultramarathons or going through Navy SEAL training makes me think, well, I can at least bang out another rep on the bench press, or I can do a couple more ab crunches.

Most of the time, I train without music or anything, just whatever the gym is playing, which tends to be terrible, frankly. But now and again, I will play something like this, mainly in rest times between sets, because when I am performing the exercise, I want every bit of my focus dialled into performing the task at hand, and I want to block everything else out.

Listening to these kinds of motivational speeches has helped me change the tune of that inner voice in my head, which will often take the easy path if I pay it too much attention.

Try it next time you are in the gym or out for a run, and I bet I’m not the only one it works for.

Book of the Week / What I’m Reading

First You Write a Sentence by Joe Moran

If you have noticed my grammatical mistakes so far, you’ll be thankful to know that I am working on improving my writing. This week, I am reading First You Write a Sentence, and so far, it has been a wake-up call on taking grammar much more seriously, which, as you will have spotted, is very much a weakness of mine.

So far, the early chapters focus on how the proper use of verbs and nouns improves writing

Last year, I read Bird by Bird, which is another book aimed at budding writers. I got so much from that particular book (I will probably re-read it again soon) that I thought it was very important to stay on the topic of improving my writing, especially as I am publicly publishing my newsletter and blogs.

A side note: I’m currently averaging a book a week, and what is also interesting is that having set myself a commitment to write a weekly newsletter is pushing me to do my reading. I doubt I will be able to keep this reading pace for the whole year, but for now, it is a nice flow, being able to tell you all about what I am reading and a different book every week.

As always send me a direct message or comment if you want to add your say on any of these topics.

Have an incredible week ahead. Keep iterating, keep trying, and keep learning!

Yours faithfully,

Matthew Barton