I Made 50-75 Cold Calls a Day. Here’s the Sales Reading List I Wish I’d Had

There was a stretch of my life where I made 50 to 75 cold calls a day and earned less than $30,000 a year doing it. I don’t say that for sympathy. I say it because that job is where I learned that selling is a skill you build, and I picked up most of it the slow way, by getting hung up on. A handful of books could have shortened the curve.

Disclosure: this post has a couple of affiliate links (Amazon searches). If you buy through them I may earn a small commission at no extra cost to you. I only point to books I’ve read or would hand to a friend. Not financial or career advice, just what I’d do.

Later, cold calling is how I landed a vending location at an assisted living facility with around a hundred employees. I wrote about that day when it happened. Same skill, different stakes: nobody was paying me a commission anymore, but a yes on the phone still turned into a machine on a wall.

So here’s the list I’d give my younger self, in the order I’d read it. Not the “best” sales books in the abstract. The order that matches how the skill actually builds.

Why the order matters more than the list

Most reading lists are flat. Eight titles, pick any. The problem is that sales is a stack of skills, and reading the advanced ones first just gives you vocabulary for problems you don’t have yet. I’d group it in four stages:

1. Be someone people don’t mind talking to.
2. Survive the rejection long enough to get good.
3. Make enough calls that the math works.
4. Get better at the conversation and the offer.

Stage four is where most people want to start. It’s the fun part. But most people starting out aren’t short on clever lines. They’re short on volume, nerve, and genuine interest in the person on the other end.

Stage 1: How to Win Friends and Influence People (Dale Carnegie)

Published in 1936, and it’s still the first thing I’d read. The core idea is almost embarrassingly simple: people care about themselves, so be genuinely interested in them. Remember names. Talk about what they care about. Let them do most of the talking.

On a cold call that translates to one thing: the first thirty seconds are about the other person’s day, not your product. A property manager has a leaking roof, a tenant complaint, and a vendor who didn’t show up. If you sound like you understand that, you get another thirty seconds.

The honest weakness: read cynically, it becomes a manipulation manual, and people can smell that. The anecdotes are from another century. Take the principle, not the stories.

Stage 2: The Greatest Salesman in the World (Og Mandino)

This one has been on my recommended list for a while. It’s a short parable from 1968 about a camel boy who receives ten scrolls of wisdom, and the instruction is to read each scroll repeatedly for a month before moving on to the next. There’s no script in it and no tactic.

Why it’s second: the thing that kills most people in sales isn’t a bad pitch, it’s the fortieth no of the day. Mandino’s scrolls are basically a daily mental routine for persistence and self-respect. In any job built on dials, the people who last usually aren’t the most talented. They’re the ones with some way of resetting between calls.

The honest weakness: it’s a fable with a spiritual tone, and if that’s not your thing it will feel thin. It will not teach you what to say.

Stage 3: Fanatical Prospecting (Jeb Blount)

Now the volume. Blount’s big idea is that the deals you close in any 90-day window come from the prospecting you did in the 30 days before it. Skip a month of calling because things feel good, and you’ll feel it a quarter later. He pairs that with a “law of replacement”: every closed or lost deal leaves a hole in the pipeline you have to refill.

Anyone who has worked on commission knows the feast-and-famine version of this. If you’re building a vending or ATM route, the same rhythm applies: locations churn when managers leave or buildings sell, and the only protection is a calendar block for prospecting that doesn’t move.

The honest weakness: it’s long and repetitive, and it’s written for quota-carrying corporate reps. Skim the CRM chapters.

If you want it, Fanatical Prospecting is on Amazon here.

Stage 3, continued: $100M Leads (Alex Hormozi)

I’ve written about what I’ve learned from Hormozi before, and this book genuinely helped me understand how new customers actually show up. His framing is that there are only four ways to get attention: warm outreach to people who know you, content, cold outreach to strangers, and paid ads. He suggests getting good at them roughly in that order.

If I were starting a route over, I’d take that order literally: text the twenty people I know and ask who manages a building or runs an office before dialing a single stranger. Warm first is cheaper, faster, and less soul-crushing.

The honest weakness: it’s written for online businesses, heavy on frameworks, and the paid-ads section is way more than a local operator needs.

$100M Leads on Amazon, if you want the whole thing.

Stage 4: Never Split the Difference (Chris Voss)

Once you’re getting conversations, the next wall is objections. Voss is a former FBI hostage negotiator, and the two tools I’d steal are labeling and “how” questions. Labeling is naming what the other person seems to feel (“sounds like the last vendor left you hanging”). “How” questions (“how would you want restocking handled?”) pull them into solving the problem with you instead of against you.

The honest weakness: the hostage stories make every negotiation sound life-or-death. A break-room machine isn’t. Used too heavily, the techniques feel like techniques.

Stage 4: The Challenger Sale (Matthew Dixon and Brent Adamson)

This one argues, from research on a large number of B2B reps, that the best performers in complex sales don’t just build relationships. They teach the customer something about their own business, tailor it, and aren’t afraid to push the conversation forward.

For a small operator, the useful slice is “teach.” If you can tell a gym owner something true they didn’t know (say, what members buy after a 6 a.m. class), you stop being a vendor and start being useful.

The honest weakness: it’s written for enterprise sales teams, and some readers come away pushier instead of more useful. The “take control” part needs a light touch.

Stage 4: $100M Offers (Alex Hormozi)

Last, and it’s the one I was working through back in 2022. The idea: make an offer so good people feel dumb saying no. He breaks value into the dream outcome, how likely they believe it is, how long it takes, and how much effort it costs them.

Run a vending pitch through that and it gets sharper. The location gets an amenity (dream outcome), from someone with references (likelihood), installed this week (time), and they never touch it (effort). A lot of pitches only talk about the machine.

The honest weakness: it’s aimed at people selling services and info products, and some of the pricing advice doesn’t translate to a free placement.

What I’d practice after each one

Book	Practice for one week
How to Win Friends and Influence People	Ask one question about their day before saying what you do
The Greatest Salesman in the World	A two-minute reset ritual after every no
Fanatical Prospecting	A fixed daily call block, tallied on paper
$100M Leads	Text 20 people you already know
Never Split the Difference	Label every objection before answering it
The Challenger Sale	Bring one useful fact to every pitch
$100M Offers	Rewrite your pitch around their effort, not your machine

The part no book gives you

Every one of these assumes you know who to call. That was always the hardest part for me: finding the right locations meant driving around and calling managers who turned out not to be the decision-maker at all.

If you’re pitching vending or ATM locations, there’s a more operator-focused take on this topic: eight sales and cold-calling books for landing vending and ATM locations, with a different set of picks and the call math.

If I could send one note back to the version of me dialing 75 times a day, it wouldn’t be a script. It would be: read one book, practice one thing for a week, then read the next. And stop taking the no personally. It was never about you.