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- I promised 3,900 pitches... I sent 6
I promised 3,900 pitches... I sent 6
How the fear of rejection almost ruined my business & what changed.

“Nothing ever changes until It’s real” - Fritz Perls
I don’t know about you, but mornings are my favorite part of the day.
Crawling into bed at night is a close second, but mornings are what I most look forward to.
This has been my truth for a few years now.
The first hour of the day is crucial for me because it sets the tone for the rest of my work: Client calls, writing, the ever-growing ‘honey-do’ list.
Which reminds me I still need to replace the broken door knob in the living room… ok, I digress.
I love everything about my routine, but if I’m going to be honest with you, there’s one thing that I left out.
A crucial detail.
Every morning for almost 3 years, I promised myself I’d send five partnership pitches each day, Monday through Friday.
Because collaborations have been the most dependable strategy I’ve ever had in my business.
Not ads. Not organic IG content or even that one viral TikTok I had. People really liked the one where I shared that I used to be an escort… Crazy but true.
Every day, I’d look at “Send 5 Pitches” written on my whiteboard, and I even blocked 9–10 a.m. on my calendar, convinced that scheduling it would guarantee I’d do it.
But for 3 years, I didn’t send 3,900 pitches ( 5 per day, 5 days a week for 3 years)
I sent exactly 6.
Partnerships have always been my favorite growth strategy—zero money required, just time to research potential partners, write a simple three-paragraph pitch, and press send. Then repeat.
This takes less than an hour to send all five, yet it took me over 3 years to get out of my own way and start sending them daily.
Why was it so hard? Because I feared being rejected more than I feared being broke.
A great strategy for staying small.
A terrible strategy for wanting to get married.
I’d grown up believing that if I had more opportunities, more money, more luck than others, it made me a bad person somehow.
I believed that success was for the chosen few: the smart, the special, the lucky.
So I procrastinated — out of fear.
Then reality hit.
I found myself in a financial bind, and just “looking successful” was no longer going to work.
I had to step up if I was going to become the kind of husband Allison deserves.
I was still terrified of rejection, especially from people I admired—but I had no choice.
I sent the first pitch to a close friend who I knew would probably say yes so that I could boost my confidence a little.
Then I started to pitch people I genuinely wanted to collaborate with, who I didn’t know personally but had connections to.
I got rejected by some.
Ghosted by others.
And Yesses from a few.
Since then, those few Yeses have:
• Launched collaborations in Mexico, Guatemala, and Costa Rica
• Generated tens of thousands of dollars in new revenue
• Connected me with inspiring people with who I’m now in talks about collaborating with
Here’s what these collaborations have done for me that posting never did—and what they will do for you as well:
Instant Leverage: Borrow someone else’s trust instead of begging for attention
Time Freedom: 1 hour of pitching delivers more impact than a week or even a year of posting
Less Stress: No more dopamine crashes, scroll-addiction, or “what do I say?” days
Accelerated Growth: 10× ROI on your effort vs. daily content hell
Courage—not permission—is all you need.
That same courage that fuels your very first strategic pitch will be the courage that unlocks partnerships that scale your business faster than any social media “hack”.
So think about this: What do you believe has a better chance of changing your business over the next 30 days - Your next post or your next pitch?
If you want to learn how to generate real partnerships and grow without social media, join The Successful Solopreneur and learn how to pitch your way to the business and life you deserve.
Your teammate,
Matthew
If you’re ready to take the next step, here are two ways I can support you:
1. 🎧 Listen to The Successful Solopreneur Podcast
Candid conversations on unlocking your potential and building a business that aligns with who you’re becoming.
2. 🗓️ Book a Free Discovery Call
Prefer a more personal solution? Let’s talk about where you’re stuck and how I can help.
Real Wins from Real Readers
My client Tommy sent me this after using the Unfair Advantage Framework to pitch a new collaboration for his company