Your Emails Aren’t Being Ignored - You Just Don’t Have a Follow-Up System
A proven, practical way entrepreneurs can get replies without being annoying, inspired by sailing through shipping lanes to Catalina
Out on the water, communication is not optional. It is expected.
Every vessel is supposed to monitor VHF Channel 16. That is the international hailing and distress channel. It exists for one reason: so ships that are near each other can quickly communicate when it matters.
When I sail to Catalina, I cross active shipping lanes. These are not casual waters. Three-hundred-foot tankers are moving steadily across the ocean, often faster than you expect. If I do not see them, they can still see me. They can hail me on Channel 16, and any boat within range is expected to be listening.
And if someone is not responding and attention is urgently needed, there is a universal escalation. A loud blast of a horn. No confusion. No guessing. You hear it. You look up. You respond.
Unfortunately, email does not work that way.
People are not always monitoring their inbox. Messages get buried. Notifications are missed. And email, unfortunately, does not come with a horn.
That is why your EntrepreneurSHIP needs a proven and practical email strategy. Hope is not a strategy. One follow-up is rarely enough. And I have learned this the hard way.
Why People Ignore Your Emails (It’s Usually Not Personal)
I hear entrepreneurs complain about this constantly. “No one ever emails me back.” The frustration is real, but silence almost always has a reason.
Most inboxes are overloaded. Decision-makers receive dozens, sometimes hundreds, of emails a day. Your message may be seen briefly and then pushed down within minutes.
Timing matters more than people realize. Your email might arrive during a busy season, a holiday week, summer travel, end-of-quarter chaos, or a conference-heavy stretch. Even good emails get ignored when timing is off.
Many emails are skimmed on phones. If your message is long, dense, or unclear, it gets mentally bookmarked for later and then forgotten.
Sometimes there is no obvious next step. If the reader is unsure what you want them to do, replying feels like work, so it gets delayed.
Emails also get forwarded internally and stall. Or they are read quickly and simply forgotten.
And yes, sometimes people just forget.
Silence rarely means no. It usually means later, and later never comes without a reminder.
Why I Built The Channel 16 Follow-Up System
I know this problem well. I have spent more than a decade sending emails professionally. Thousands of them. Across startups, universities, partnerships, events, consulting work, and media.
I also have four podcasts, which means I regularly reach out to potential guests. Some are early-stage founders. Some are mid-level leaders. Some are some of the biggest names in their industries.
For years, I handled follow-up the same way most people do. I sent one email and hoped. Maybe I sent one follow-up. Then I stopped.
What I realized is that very few entrepreneurs actually have a follow-up strategy that works consistently over time.
This system came from years of trial and error. I tested different timing, tones, and formats. Once I started seeing replies show up after the third and fourth touch, I knew I was on to something.
The Channel 16 Follow-Up System Actually Works
This is not about being pushy. It is about being organized, visible, and professional.
Think of it as building your own version of Channel 16 for email.
Step 1: Sending the First Email
Before you write anything, be clear about the person.
Not just the company. Not just the department. One specific person with a reason you are reaching out.
Clarity here improves everything that follows, from subject line to call to action.
Confirm the Email Address
This step feels minor. It is not.
If the email address is wrong, no follow-up strategy will work. Double-check the company website, LinkedIn, or known email patterns. If possible, confirm it through multiple sources.
Take the extra minute now instead of weeks of frustration later.
Send a Short, Clear First Email
Your first email sets the tone.
It should be professional, concise, and easy to read. The entire message should be readable on a smartphone screen without scrolling.
Use a clear subject line. Get to the point quickly. Include one specific call to action.
Not two. Not three. One.
Then send it and move on.
Decide Your Follow-Up Timing in Advance
Before you even send the email, decide how long you will wait before following up.
Three days. Five days. A week. Two weeks. There is no universal rule.
Be mindful of context. Is it a busy holiday season? Summer? End of quarter? Choose a timeline that makes sense.
Then set a calendar reminder. Do not rely on memory.
Step 2: The Friendly Follow-Up
When your reminder goes off and you have not heard back, do not write a brand-new email.
Find the original email you sent and forward it.
Your email client will add “FWD” to the subject line. Remove it and replace it with:
Friendly Follow-Up: [original subject]
Keep the message extremely short. Something like:
“Ahoy, just a friendly follow-up on the note below.”
Then send it.
Decide how long you want to wait until the next follow-up and immediately set another reminder.
Step 3: The Second Request
When the next reminder arrives, repeat the process.
Forward the friendly follow-up. Change the subject line to:
2nd Request: [original subject]
Write a brief, positive note. One or two lines is enough.
Again, decide your timing and set the next calendar reminder.
The Magic Step 4: The Third Request
Now do it one more time.
Forward the last email. Change the subject line to:
3rd Request: [original subject]
Keep the tone calm and professional.
Then pause and notice what you have created.
Why This Works (The Psychology Behind It)
By the time you reach the 3rd Request, you have created something most people never do.
You now have four emails in one clean, organized thread. The original message and three reasonable follow-ups, all documented in a single place.
This is no longer about you being impatient. It is about clarity.
The thread shows consistency, professionalism, and follow-through. It makes it easy for someone to respond without having to search their inbox or remember context.
There is also a subtle psychological shift. This email chain could be forwarded. To a colleague. To a manager. To customer service.
That possibility matters.
Just like repeated radio calls followed by a horn blast at sea, escalation without emotion gets attention. Not because it is loud, but because it is unmistakable.
For most people, this is where the reply comes.
And if it doesn’t, that silence is also information.
At this point, you have done your job.
A Side Effect Most People Don’t Expect
Something interesting happens when you use this system consistently with people you already work with.
They learn your pattern.
I use this follow-up sequence all the time. And many people reply at the Friendly Follow-Up stage, not because they suddenly remembered, but because they recognize what comes next.
I’ve had people tell me, “When I see your friendly follow-up, I reply, because I know if I don’t, the next email is going to say ‘2nd Request.’”
That’s not fear. That’s clarity.
You are not being annoying. You are being predictable in a good way.
Over time, this builds a quiet form of accountability. People know your emails do not disappear. They know you follow through. And they know replying sooner is easier than replying later.
The system starts working faster because the expectation is already set.
Just like at sea, when everyone knows Channel 16 is being monitored, fewer signals are needed. The structure does the work for you.
If They Don’t Reply
If someone doesn’t respond after the 3rd Request, that is usually where I stop.
By that point, the message was clear. The follow-up was professional. The thread documents reasonable effort.
I am not interested in spamming people.
EntrepreneurSHIP is about signaling clearly, not chasing every ship on the horizon.
That said, if you do want to explore options beyond the core system, think of the following as extensions, not requirements. These are situational tools you can use when it makes sense.
Option 1: Try a Different Channel
Before sending another email, pause and ask yourself a simple question.
Is there a better way to reach this person?
A phone call can still be the cleanest signal. If you have a number, try it. If not, see if you can find one.
If you are connected with them on LinkedIn, a short message referencing the email thread can work well.
And if we are connected on LinkedIn, I am often happy to make an introduction if it helps move things forward.
Sometimes the issue is not interest. It is timing, visibility, or trust.
Option 2: The Soft Redirect
If email still feels like the right channel, there is a low-pressure move that often works.
Forward the 3rd Request and change the subject line to:
Quick Question
In the body, simply ask whether there is someone else you should be following up with.
This removes pressure and invites help rather than a decision. Subtle, respectful, and surprisingly effective.
Option 3: The Internal Nudge
If you are dealing with a company rather than an individual, you can try an internal nudge.
Forward the same email thread to a general or customer service inbox.
Politely explain that you have been trying to reach the person and ask whether the contact information is correct or if someone else can help. Include the thread below.
This often triggers internal movement without putting anyone on the defensive.
Option 4: Persistence for High-Level Contacts
Could you continue past the 3rd Request?
You could.
It is bold. It might feel uncomfortable. And yes, it could annoy the person you are trying to reach.
But it can also work.
For executives, public figures, or big influencers, continued persistence sometimes signals seriousness rather than desperation.
Fourth request. Fifth request. Sixth request.
Spaced out. Calm. Professional.
Persistence, when done respectfully, can get attention. In a good way or a bad way.
If you were a big name and saw a forty-seventh request sitting in your inbox, do you think you would finally hit reply?
What Are You Waiting For?
This system works across sales, partnerships, mentoring, podcast outreach, sponsorships, customer service, and collaborations.
They might not be monitoring Channel 16, and email does not come with a horn. But this strategy creates the digital equivalent of a loud, unmistakable signal when it matters.
So now what?
Think about the people you want to reach or have already emailed without a response. Pick one. Try this system. Then decide if you need any of the extensions.
Let me know how it works.
Building your EntrepreneurSHIP relies on your ability to get the attention of other ships out there on the high seas.