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Most outreach fails for one simple reason: it creates work for the person you are trying to reach.
Busy founders are not ignoring you because your idea is bad. They are ignoring you because your message is an ask, not a contribution.
On a recent episode of The Unordinary Podcast, Taylor Prokes shared how she got on Jesse Itzler’s radar. It was not with a deck. It was not with a job request. It was not with "can I pick your brain?"
It was with value first. And she did it longer than most people are willing to.
Her approach got her onto Jesse Itzler’s radar, and now she’s the co-founder and CEO of The Big A## Calendar, a product she and Jesse developed designed to keep your attention focused on your goals, events, trips, and any other incredible things that you decide to plan.
The idea behind the calendar is to take "regret" out of your vocabulary and take control of your year with a fun and functional calendar that works, because a memorable year won’t happen unless you plan it.
Here is the playbook that took Taylor from fan to CEO.
Most cold outreach sounds like this:
Every one of those creates work for the recipient.
They have to decide whether you are worth the time.
They have to review something.
They have to imagine where you fit.
They have to manage the obligation of replying.
Taylor sees this constantly. People show up in her inbox trying to get to Jesse with asks. People show up at events handing her decks. Her reaction is simple: this is not the time and it is not helpful.
The hidden filter busy operators use is straightforward:
If the answer is no, no, and yes, you will get ignored.
Taylor did not start by asking for access. She started by entertaining.
She and a friend wanted to get invited to Jesse’s endurance event, Hell on the Hill. Instead of asking repeatedly, they made 100 creative videos running up hills around San Diego. The first video stated their intention clearly. After that, they simply shipped entertaining content for nearly a year.
No constant follow ups. No pressure. No pitch.
Just value in a format that Jesse already loved: storytelling and humor.
That is to give first outreach.
Here is how to apply it.
You do not need to do everything. You need to do one thing well.
Your lane might be:
If you are reaching out to a founder who lives online, create three social posts tailored to their voice. If you are reaching out to an operator, send a tight teardown of something they are building. If you are reaching out to someone vocal about a mission, send them a relevant article plus your distilled takeaway.
Taylor put it simply on the podcast: if you want to run someone’s social media, send three assets that would crush. Do not send "I will do anything." That puts work on them.
Taylor understood that Jesse responds to story and energy. So she gave him story and energy.
If the person you are targeting is an investor, give them leverage. If they are a storyteller, give them moments. If they are building a brand, give them brand ready assets.
Most outreach fails because it is generic. It could have been sent to anyone.
Specificity signals respect.
Most people over index on volume. They send ten follow ups. They write long paragraphs explaining their background.
Taylor did the opposite. She showed taste. The videos were aligned with the event. They were funny. They were self aware. They fit.
You can work hard in private. Publicly, show that you understand the room.
After a year of shipping entertaining content, Taylor asked directly: are you going to invite us?
The answer was yes.
The ask works when it feels earned.
Online outreach is one thing. In person behavior is where most people lose the plot.
At high-energy events like Running Man, Taylor sees people make the same mistake. They walk up and immediately start pitching. They hand over decks. They explain why their company would benefit from access.
That is a fast way to become transactional.
Her advice is simple: be memorable, not salesy.
At Hell on the Hill, she did not try to force deep business conversations. She brought energy. She participated fully. She made the weekend better for the people around her.
That created rapport.
If you want a relationship, act like someone worth having a relationship with.
There is a time to pitch. It is usually later.
If you meet someone in person, your follow-up should be short and useful.
Three parts:
Not a life story.
Not a deck.
Not a vague "let me know if I can help."
Make it easy to reply.
Give first outreach works because it reduces friction.
You are not asking someone to imagine your value. You are demonstrating it.
Taylor did not say she could help grow a brand. She grew one. She showed she understood the audience. She made things people wanted to watch.
By the time she officially stepped into the role, the proof was already there.
If your outreach makes their life easier, you will get replies.
If it adds work, you will get ignored.
That is the difference.
Subscribe to The Unordinary Podcast and listen to the full episode with Taylor here.
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