Can 100 cold calls change your life?
That was the question I started this week with.
Cold calling is something I feared for years. Reaching out to complete strangers, on the phone, with nothing but your voice and a half-baked pitch.
It felt impossible and cringe….
But here's the thing I realized: if you can call 100 people you've never met and be genuinely useful to them, you can reach ANYONE on the planet.
Mentors, clients, partners. The whole world opens up when you stop being afraid of the phone.
So I did it. And I recorded the whole thing.
What happened:
The first 10 calls were brutal.
I fumbled. I paused too long. One guy hung up on me mid-sentence. My voice was shaky. I sounded like someone reading off a teleprompter.
I was cringe, I’m not gonna hide it.
So I did something different. I pulled out ChatGPT and practiced the call 20 times with AI before dialing real people. Just roleplay, back and forth, until I could say my opener without thinking.
The next 50 calls were where the pitch got refined.
People were giving me 30 seconds, but I was wasting them with vague offers. "Can I help with your listings?" doesn't mean anything.
So I got specific: "Is your lead follow-up system automated or completely manual?" That one question changed things. People started actually talking to me.
The last 20 calls were fun! I was smiling.
One lady told me about her trip to Florence. Another said, "You seem nice, I'm not going to hang up on you."
Remember that these are complete strangers. Cold calls. And we were having real conversations.
3 Things I learned that can help you:
The first 10 calls are supposed to suck.
You're not going to be good. That's the whole point. It took me 3 days just to work up the courage to dial the first number. Once I accepted that the first 10 would be garbage, I could actually start.
Stop waiting to feel ready. You won't.
Don’t sell, just ask.
Every time I pitched something, people hung up.
Every time I asked a genuine question about their business, they opened up.
"Do you have 30 seconds for two questions?" works because you're not asking them to buy anything.
You're asking them to talk about themselves. People love that.
You don't need fancy tools.
I wasted days trying to set up Apollo, PhoneBurner, power dialers, email warmup tools.
All of it was overcomplicating the simple thing.
What actually worked: a prepaid US phone number, leads from realtor.com (their numbers are public), and a Google Sheet. That's it.
The whole stack cost me about $25.
Why this matters for you
You probably have a business idea, a product, a service, or just a burning question that the right person could answer. And somewhere out there, that person's phone number exists.
The only thing between you and that conversation is the willingness to be awkward for 30 seconds.
That's the entire skill.
And it gets easier absurdly fast. By call 50, the anxiety was gone.
By call 80, I was genuinely enjoying myself.
The math that matters: 100 calls. 20 pickups. 3 real leads. ~2 hours of calling. Claude predicted a 4% conversion rate and it was right. You don't need social media. You don't need 10,000 cold emails. You need a phone and 2 hours.
If you want to see the calls, the fumbles, the script I used, the simple Google Sheet CRM, and how I used AI to practice before calling real people, the full video breaks it all down.
53 skills compounding:
cold approach (week 5) made me more comfortable talking to strangers.
comedy (week 12) taught me to handle rejection better.
public speaking (week 11) taught me to project more confidence.
all of that helped this week.
what skill do you wish you'd learned 10 years ago? reply and tell me.
And join me and try things out!!
What's next?
Week 16 starts tomorrow. New skill. New challenge. If you have something you want me to attempt, reply to this email. Seriously.
The crazier the better.
Until then, go cold call someone :)
If you missed the previous weeks and unusual lessons, check them out HERE:
Learn all the other unusual life lessons at 53skills.com
Reply to this email with all your questions, comments, or tips, I will answer.
Or share with friends who want to improve their life.
- Alex

