February 14, 2017

Sales #FAILS: How salespeople often snatch defeat from the jaws of victory.

You have to admire salespeople, they have the most thankless job on earth. You can get away with nearly any kind of slur, insult or stereotype if you simply make the butt of it a salesperson. They have to handle endless rejection and if they do their job right, they take home the largest paychecks, likely earning them the envy and derision of everybody else at the firm (who would be unemployed without them however….)

For the longest time my main business had no sales or marketing. Over a decade, closer to 15 years, the product “just sold itself”. I was nauseatingly smug because of it. “Marketing is for losers” or “Salesmen? We no need no stinkin’ salesmen

Turns out, I was the loser. I was the idiot. What I didn’t realize was that we were marketing and we were selling, every day. We just didn’t have a team solely tasked with that and I thought anybody who did was admitting weakness.

Then one day I woke up and I realized a company that started out the same time as me, used to be roughly the same size as mine, was suddenly doing over 100 million / year in sales and mine was still flopping around the single-digit millions and stuck there. WTF?

Then I understood what had happened. They had a salesforce over 350+ strong. Granted, they were losing money. As one mentor of mine remarked, “Antiguru (not my real name), anybody can take in 100 million / year provided you’re willing to lose enough money”. Fair point. You can take anything too far. But overall, they had kicked ass. For awhile they were obscenely profitable but then they just overshot (subject of another post someday).

Around the same time I had invested in another company, outside my circle of competence and they were circling the drain. Another friend of mine suggested I run a 4-day email sequence on everybody who had ever purchased from them. I recoiled in terror. Sales pitches? Marketing sequences? Won’t those customers flip out?

They didn’t. We sold more product in those 4 days than we had all year so far (8 months in). But it was too little too late for that venture and, other factors being unchanged, I ended up losing my entire investment. But by then I had gotten the message:

Sales and marketing works.

What needed to happen was that I had to understand what my main business was doing subconsciously and become aware of it, create systems around it, start measuring everything and then refine it.

Since then the main business has put up three consecutive years of all-time high revenues, while profits swung from losses to a decent margin tracking the top line, just like the old days.

I don’t have a huge salesforce yet. I want a small team of highly compensated firecrackers, not a warehouse full of paycheck-collecting dullards.

Like most of us, I am relentlessly hounded by salespeople. So I make the best of it and keep my eye out for any good ones so that I can offer them a position at my main business where they stand to make a lot more money.

What I find is nearly all salespeople give up right at the moment of breakthrough. I’m serious. Specifically I mean salepeople who are prospecting and selling over the internet and phone (not in person).

Why? Because the normal form of rejection is silence. If a prospect isn’t interested, they won’t reply, period. Delete that voicemail, trash that email message, next, not interested.

I’m by no means an expert at sales (other than being a very lacklustre telemarketer back in my early days), but I strongly suspect that the first goal toward creating a dialog that can result in a lead which could be converted into a sale  would be to:


Any response. An email telling the salesperson to “go fuck yourself” is actually an improvement over being ignored. (I’m not kidding. Because that’s actually a mean thing to say. I once told yet another VC who wanted to invest in my company exactly that and I emailed him back the next day and told him I was sorry for that dick move. We traded a few emails and now I’m in his goddamn rolodex.)

Any response counts. There is some motive behind any response. Your next job is to find out what it is and address it.

What I do now is ignore the salesperson for a few probes (emails, calls, etc) and then I send back some kind of rejection communication. This is a vetting process. In my case I’m not looking to buy the product, I’m looking to hire the salesperson.

They almost always waffle and fold right at the moment they’ve cracked me. I was ignoring them, and now I’m not! What do they do? They move on! It’s exactly backwards.

Last year a guy was persistent as hell and I was just flat out ignoring him. He wouldn’t give up, would not quit and I had high hopes for him. Finally after about 5 or 6 salvos he emails me while I’m on vacation, asking me to give him 15 minutes for a phone call. I type back:

“Let me get this straight, you want me to take 15 minutes out from my vacation so that you can get on the phone with me and try to sell me something?”


The correct response at this point would have been something along the lines of: Yes.

“Yes Mr. Antiguru. I know you’re on vacation but this is so important I know you’ll be glad you did” or “What I’m proposing will pay for your next vacation so why not?” Something. Anything, I’m ready to offer the job interview, because it would take so much chutzpuh to own up to interrupting somebody’s vacation and still insist on getting to pitch!

Never heard from him again.

I thought of this today because one guy was pretty good, I had hopes for him as well – he successfully started a conversation with me before I even realized he was a sales guy. Then he shifted into his pitching. I ignored it. But he kept at it, he stuck with the conversational tone he had already established with me.

This morning he asked me “Did you get a chance to read that deck I sent over?”

I replied “Not interested”.

He had me! I had stopped ignoring and replied. He should have come back with:

“Did you even read it?” (I hadn’t).


“Thanks for the reply, Antiguru!

Have a nice day.


and that’s the end of that.

Again, I’m no sales expert. But I would say as long as you have the dialog going, you are in the running, and if you, the salesperson, terminates the dialog then you’ve just killed your own lead.

A good book which I wish I read back at the beginning of launching my business is Michael Masterson’s Ready Fire Aim: From 0 To $100 Million In No Time Flatwhich does a fantastic job of helping you understand where in the priority list marketing and sales should be within your business and how to implement the systems to get there.