Handwritten Hammer
Written by the Owner of Letter Friend
Ryan makes a bold statement – “this would be a passion project for us”.
Wait, what? What does that even mean?
I’m a philosophy major, so all the questions flood my brain:
- What is he thinking, and why?
- Does he say this to everyone?
- Is he this clever and therefore this might be a good match?
- Is he just willing to say whatever in order to get the business?
- Does he take his words seriously enough?
- How does he define the word “Passion”?
So I decide to keep the card to look into this further. I’m not calling him, I’m not emailing him; I decide to keep the card to look into this further at some later time. I just put the card down and it sits on my desk for 2 days. I’m still on the fence, but he did leave a lasting impression.
The note that sat on my desk for two days.
I need a nudge.
Then comes the nudge.
He does exactly what we recommend for our clients to do—a multi-touch effort when using handwritten notes. Don’t just send and forget; also reach out via email or phone to confirm the prospect received the note. He did exactly that. He sent an email with a subject line “Mailed you a letter.” This effort lifts email reply rates tremendously. “He knows what we know” – I’m thinking to myself.
I obviously open it and confirm to myself that now I know Ryan gets it. He knows my product, he used it, and it worked. I respond by being open to chat more.
The Research & The Red Flags
Now it’s time to do some research on who this guy is and why he is good, and will I find any red flags?
A quick Google search lands me on a 32-minute video interview where Ryan talks about his Fairway Finder—an easy way that helps golfers find tee times. I watched the whole video.
The interview is insightful. He articulates himself well, pays close attention to the questions of the host, and answers them competently. He doesn’t rush and thinks things through; he doesn’t embellish, knows his obstacles, and is willing to say “I’m not sure” or “I don’t know” if he really doesn’t know. Plus, they touched on Aristotle’s “first principle thinking” which further reassured my analytical mind.
The fact that he is a “non-technical founder” but is a founder of a technology-based startup resonated with me further. My background is in philosophy. My Master’s is in counseling, but I’m 16 years in running a direct mail company which automates the process of sending handwritten notes via API. Does he know how to find an ideal customer? I’m not sure. Is this a coincidence? I don’t believe in those.
Judging the book by its cover
Ok, enough of the rambling, let’s get to the red flags which I discovered while trying to judge the book by its cover.
The interview I watched from Wantrepreneur is from June 2025. His LinkedIn is flooded with what seems to be his main focus – Fairway Finder. Then I visited Abyssal-digital.com and it’s niched for Shopify Brands (we are neither of those). So, his focus is elsewhere. Then why Letter Friend?
That’s when one specific hammer phrase still stood out: “Passion Project.”
Well, now we have to talk. I scheduled for Thursday.