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Last year I watched a colleague enter Q4 at 53% of quota. While we were grinding 10-hour days trying to create something from nothing, he gets assigned a perfect inbound lead.

Recently failed an audit. Need a solution before their next board meeting. HOT prospect.

Three weeks later: deal closed, quota hit, later earned a promotion.

“Good breaks happen to get people” as he said.

The whole team was pissed, "Of course, Chad would get the gimme deal." — “while we’re grinding out activity, he gets an inbound gift from god”

Months later during a deal review, we discovered the truth. That "random" inbound? It came from a referral Chad earned from a previous customer.

We see this pattern everywhere:

• The AE whose enterprise deals close themselves

• The startup featured in TechCrunch "out of nowhere"

• The rep who gets routed the best leads

• The founder whose content goes viral "by accident"

Let’s dive into how to create your own sales luck.

Engineering Your Own Luck:

Most of what we call "luck" is actually the compound effect of deliberate actions.

Sahil Bloom calls this expanding your luck surface area: "Much of what we call 'luck' is the macro result of 1,000s of micro actions."

Think of it this way: When Donnie from Wolf of Wallstreet approaches Jordan inside that restaurant, it's not random luck. He noticed the Jaguar, positioned himself in the right neighborhood, and asked for the job one he saw that $72k check. When the opportunity presented itself, he had maximum surface area to catch it.

What looks like being in the right place at the right time is usually being in the right place (or doing the right things) consistently.

The Four Types of Sales Luck

Most reps experience only one. Top performers engineer all four.

1. Random Luck: Position yourself where good things are likely to happen

2. Hustle Luck: Do more of what works to create more opportunities

3. Expert Luck: Act like the expert and people will eventually treat you like one

4. Magnetic Luck: Your reputation draws opportunities to you

“Lucky” Case Studies

Here's how three different people expanded their luck surface area:

The Founder Who Bet Everything on Content: Neil Patel made a massive bet on thought leadership when content marketing wasn't even a thing. While competitors focused on traditional advertising, he consistently created educational content about digital marketing. The payoff? His blog now generates over 4 million visitors monthly and landed him clients like Amazon, Microsoft, and Google.

The Rep Who Became the Analytics Expert: Matt Phillips created a simple "Sales Metrics Cheat Sheet" and shared it on LinkedIn. Now he's positioned as the sales analytics expert - prospects reach out to him instead of the other way around. One piece of helpful content turned him from hunter to hunted.

The Side-Hustler Who Built a Business: I started writing random thoughts and learnings on Twitter and created this newsletter (thanks for reading). Now people reach out for consulting advice on building go-to-market channels and driving pipeline. I've been invited on podcasts, approached for content partnerships, and it's scaled into a $3-5K monthly side hustle. Random tweets about sales problems turned into a reputation as someone who understands revenue growth.

Pick My Brain:

I’m excited to start an occasional “mailbag” section. This is your chance to ask me anything and I’ll pick some to feature in future posts:

• Outbound strategy questions

• Building a partner channel

• Career positioning advice

• Side hustle moves to consider

• Anything else you’re curious about

I’ll pick a handful and answer them here in the coming weeks.

Until next Thursday,

TSG

P.S. I reply to all emails.