I’ve Been Phonin’ Night and Mornin’
WMMM #113- This week I share a perspective on a somewhat controversial topic.
Jeff Keplar Newsletter July 7, 2026 6 min read
Prospecting
“Hi Ms. Decision-maker, this is Jeff Keplar with Stealth Startup. This is a cold call. Feel free to hang up on me right now, or give me 30 seconds to tell you why I called.”
Is there still a place for prospecting?
The act of calling a complete stranger to book a 30-minute meeting is a “life skill.”
This ability is foundational to prospecting, which requires us to call someone we do not know, successfully get them to answer the phone, engage them in a conversation, and secure an appointment.
Developing this skill is difficult and requires a specific set of capabilities, including strong communication skills and an understanding of behavioral science.
It also demands extensive practice and perseverance to master.
Ultimately, learning to confidently cold-call a stranger and secure an agreement for a next step is a valuable life skill that will serve you throughout your career.
But let’s examine some of the most recent B2B outbound benchmark data.
Cold-Calling and Outbound Touches
Unknown Call Barrier: 87% of professionals will never answer a call from someone not in their contact list. This is driven by the widespread transition away from dedicated office desks to mobile/hybrid communication, as well as strict carrier-level spam labeling.
The Connect and Friction Rate: It takes an average of 8 to 12 manual dials just to connect with a single prospect over the phone. Across an unassisted list, the baseline connection rate sits around 15% to 16.6%, meaning 5 out of 6 dials result in immediate dead air, voicemail, or an instant hang-up.
The Conversion Funnel: Modern outbound data shows that the typical cold-calling conversion rate (dial-to-booked-meeting) for average campaigns sits at a staggering 2% to 3%.
The Math: For an average outbound representative using basic targeting, it requires between 80 to 120 manual touches (a mix of unassisted dials, basic LinkedIn touches, and generic emails) just to secure a single booked meeting.
Cold Emailing Success Rates
Reaching decision-makers and executives at enterprise or Fortune 500 companies via cold email has become extremely difficult. Tighter Gmail and Outlook spam enforcement, coupled with advanced AI-assisted inbox triage tools, heavily penalize unauthenticated domains and algorithmic outreach.
Because of this, the conversion to actual business outcomes from cold introductory emails is exceptionally low:
Average Quality / Mass Outbound: Blasted or automated campaigns without deep research yield a 0.2% to 1.0% positive reply rate, often dropping below 0.5% in saturated markets like software and tech. The ultimate conversion rate to a closed deal sits at a microscopic 0.04% to 0.2% (requiring up to 2,400 emails to yield a single result).
Superior Quality / Deep Personalization: Highly personalized emails (leveraging custom snippets that reference specific pain points, hiring trends, or company triggers) achieve an average reply rate of 3.4% to 5.8%, rising further when lists are restricted to fewer than 50 highly targeted accounts.
Key Takeaway: The structural barriers embedded in modern communications technology mean that cold outbound has effectively become a high-volume statistical grind. A warm, trust-backed introduction remains the only reliable friction-free entry point to high-value decision-makers.
So if one had any other way to reach their target in a Fortune 500 company, they would use it, right?
Yet here we are.
Phonin’ night and mornin’.
When we want to help a small tech company, we do whatever it takes to achieve the desired outcome.
“Advising” them against cold outbound outreach is solid advice, but it doesn’t get the job done.
Especially when no alternative is available.
There are many examples where a visionary and a small group of engineers “invent” a better technology.
Their “networks” don’t produce warm introductions into their Ideal Customer Profile targets.
The only business relationships they have are with their attorney, accountant, and insurance agent.
If they went the venture capital route, those VCs, partnered with a law firm, have established networks that can help.
But if they self-funded or chose Private Placement, they have limited options for warm introductions.
They have increased the difficulty of monetizing by an order of magnitude.
The time it takes to reach “escape velocity” is extended to “indefinitely.”
The Obstacle is the Way
The path to success is through the obstacle (getting appointments with the right individuals)
We don’t have the time for a high-volume statistical grind.
We don’t have high volume for one - we have fewer than 50 targets.
With success rates so low across all forms of cold outreach, it will take more time than we have to execute the required number of touches.
Time kills all tech startups.
If we aren’t growing, we’re dying.
Innovation waits for no one, and the next guy will pass us by with tech that better fits where the market is now.
So we find a way.
If we don’t have a warm introduction, who does?
How do we get a warm introduction to them?
If we don’t have a connection with the connection, who might?
How do we get a warm introduction to them?
And so on.
Have you heard of the Six Degrees of Separation Principle?
Six Degrees of Separation
The Six Degrees of Separation principle holds that all people in the world are six or fewer social connections away from each other. As a result, a chain of "a friend of a friend" statements can connect any two people in at most 6 steps.
It is a core concept in network theory and social psychology, highlighting how surprisingly interconnected the human population is.
How the Chain Works
To understand the concept, imagine you want to connect yourself to a random person on the other side of the planet—for example, a coffee farmer in Colombia:
You know your local College Professor (1st degree).
Your professor knows a Research Scientist at an international conference (2nd degree).
The scientist knows a Government Official in Colombia (3rd degree).
The official knows a Local Mayor in a rural province (4th degree).
The mayor knows a Co-op Director (5th degree).
The director works directly with the Coffee Farmer (6th degree).
Key Milestones and Proofs
While the idea was first proposed in a 1929 short story by Hungarian author Frigyes Karinthy, it has been tested and proven mathematically and socially over the decades:
The Milgram Experiment (1967): Social psychologist Stanley Milgram tested this by asking hundreds of people in Nebraska and Kansas to send a letter to a specific stockbroker in Boston. They couldn't mail it directly; they had to send it to an acquaintance they thought might know him. Among the letters that reached the destination, the average number of intermediate steps was roughly 5.5 to 6.
The Digital Age (Facebook Study): In the era of social media, the world has shrunk even further. A massive study conducted by Facebook’s data team found that the actual degree of separation between any two active users on their platform was not six, but roughly 3.57.
Why It Matters: "Small-World Networks"
In mathematics and physics, this principle is analyzed using Small-World Network Models. It shows that even in massive populations, you don't need everyone to know millions of people. As long as there are a few "hubs" or "super-connectors" (people who bridge different social circles, countries, or industries), the entire global network becomes tightly bound together.
I’d Rather Leave than Never Believe
So now that we know there is a way, why don’t more people use it?
It’s hard work.
It requires imagination and focus.
It requires skills that not everyone possesses.
It still requires time.
Think about it.
Even when we use our network, it can take a couple of “touches” to move through each warm introduction - each degree of separation.
That is 2 touches times 6 warm introductions, which amounts to 12 touches.
How much elapsed time would we plan for each touch?
One week seems reasonable, but 10 days on average is more likely.
Ten days for each touch will take us 120 days (4 months) to connect with our target.
If we are fortunate and it only takes 4 degrees of separation (we are well-connected and our connections like doing favors for us), we can reduce our elapsed time to 80 days (2 ½ months.)
Compare that with a 100-touch cold statistical grind.
The main reason that most people don’t execute this strategy?
Because they don’t believe.
They may initiate the process, but give up after a couple of weeks.
It is simply a matter of execution and timing, and we will succeed.
So now do you see why we’re phonin’ night and mornin’?
We are calling and emailing our network to get warm introductions to someone who is one degree closer to our target than we are.
We’ll keep after it until we make it through those 6 degrees.
This is our version of cold-calling (prospecting).
But remember, the result - the desired outcome of this effort - is merely an introductory call with a complete stranger.
While the response rate between each degree of separation is drastically improved (70% to 80%), we still have to convert that introductory call.
Be sure to factor in a conversion rate (10% is superior).
Let Me Go or Make Me Wanna Stay
One piece of advice when prospecting.
Be ruthless with your intent.
Get a “Yes” or a “No”.
Getting a “No” is the next best outcome to a “Yes.”
It brings clarity and moves you along, one step closer to that “Yes.”
“Maybe” is far and away the worst response to want.
Eliminate the “Maybes.”
Lessons Learned
1) Six Degrees of Separation is our warm approach to prospecting.
2) The Obstacle is Always The Way
3) Let Me Go or Make Me Want to Stay (no Maybes)
4) It takes repetition to get good.
Thank you for reading,
Jeff
