Sales Side Hustle
How to leverage your experience to earn extra income
Read Time = 2 minutes
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Your W2 job is teaching you skills people will pay for.
You just don't know where to find them yet.
Five years ago I didn't either. Then I made $1,000 writing 5 emails in my spare time.
Here’s exactly how I did it:
How I Found My First Client:
One day I was scrolling X and saw a post "how to make $1,000 on Upwork."
The content actually delivered.
I ran a search for "outbound sales" opportunities and came across a founder looking for help with email copywriting.
Here's the message I sent (save this):
Hi Neal,
It sounds like you're looking for help generating pipeline with cold email.
I'd imagine your current campaign isn't producing results because you're either targeting the wrong people, or the right people with the wrong message.
I can help with both.
In my current role I lead an outbound team of 10+ reps where I'm responsible for all email copy and phone scripts which has led to $1m+ in pipeline this year.
Please let me know what a successful project looks like from your perspective and I'm happy to get started this week.
It worked.
A week later I had my first $1,000 project - write a 5 email sequence.
What You Might Be Thinking
"I'm not qualified to consult - I'm still figuring this out myself."
You don't need to be the best. You just need to be ahead of the person hiring you.
Entry-level rep? You're making 50+ calls a day - that's more reps than most founders make in a year.
Manager? You've hired and trained a team - founders are terrible at this.
You don’t have to copy my pitch word-for-word.
You just have to show proof you do this thing every day that they're struggling with.
Here are some opportunities depending on your role and situation:
For Entry Level Workers
If you’re in between jobs or looking for extra cash.
I’ve seen reps hustle 2-3 opportunities like this at the same time $$$.
Many of these jobs are commission only - aligned to qualified meetings.
For Managers
Project-based work like this is great for experiementing with a broader offering.
Explore everything from copywriting, to outbound audits, to hiring and training.
For Directors
This can be a launchpad for referrals from my experience.
Founders run in similar circles and are quick to offer recommendations.
You can start looking for you own opportunities here.
Other keywords to search: outbound sales, cold email, cold calling, business development, BDR, SDR, AE, Account Executive, sales playbooks
Your hourly rate = [salary] / (40×52)
Before you go...
I have a special ONE-TIME offer:
The future of outbound isn’t more hustle.
It’s smarter systems.
The AI Outbound Playbook builds on The 2026 Outbound Playbook to take the manual work out of outbound research, writing, and follow-ups — saving you hours each week
Until next Thursday,
TSG
P.S. I reply to all emails