26 Podcast Guest Outreach

Skill: Podcast Guest Outreach (Depth-First Method)

What This Skill Does

Runs a two-phase LinkedIn outreach sequence to book podcast guests for Simon Severino's Sales Show. Phase 1 builds genuine trust through deep research and a zero-pitch message. Phase 2 delivers the invite only after the prospect engages. Proven with high-signal prospects who ignore generic outreach.

When to Use

• You need to invite a founder, operator, or thought leader onto Simon's podcast
• The prospect is active on LinkedIn and has published content, a book, or a methodology
• Generic "would love to have you on our show" outreach has failed or feels wrong for this person
• The prospect has a strong personality and values depth over pleasantries

The Core Principle

Earn the ask before making it. Most podcast invites fail because they lead with the ask. This skill leads with genuine curiosity about the prospect's work — and only pivots to the invite after they've replied. The result: the prospect already trusts you before the pitch lands.

Inputs Required

Before running this skill, gather:

1. Prospect name, title, company
2. Their published work — book, podcast, framework, methodology, current project
3. One correction or insight they've shared — something they said that challenged your thinking
4. Their current project or initiative — what are they building right now?
5. Their personality type — do they value depth? hate fluff? respond to data? creative?

Step-by-Step Instructions

Phase 0 — Deep Research (before writing anything)

Read their actual work. Don't skim. Find:

• Their core framework or methodology (by name)
• The real tension their audience faces that they solve
• Their current project (not just their company — what are they building right now?)
• One thing they've said that could be seen as a correction or challenge to conventional thinking

If you can't find these four things, do more research. The message quality depends entirely on this.

Phase 1 — Trust-Building Message

(Send first. Zero pitch. Zero ask. Pure curiosity.)

Formula:

[Acknowledge something they said/corrected — shows self-awareness]

[Reference their specific framework by name + name the real tension it addresses]
[Name the emotional resistance their audience feels around this tension]

[Ask a sharp question about their CURRENT project — not their past work]

Template:

[Name], your [reply/post/comment] actually made me rethink [topic] —
you're right, [reframe their correction in your own words].

I went back to [their book/framework] after that. The [specific framework]
hit differently on re-read — specifically the part about [specific insight].
I've seen so many [their audience] resist that step because [emotional resistance].

Is that the core tension you're solving with [current project]?
[Sharp question about what they're building now.]

Rules:

• Reference their framework BY NAME (not just "great book")
• Name the emotional resistance their audience has (not just the intellectual problem)
• End with ONE question about their current project — not their past
• No pitch. No mention of Simon. No ask. Nothing about you.

Phase 2 — Podcast Invite

(Send ONLY after they reply to Phase 1. Never skip Phase 1.)

Formula:

[1-2 sentences genuinely engaging with their reply — bridge from their answer]

[Simon credentials: named guests + numbers]

[Frame the invite around THEIR angle/expertise — not Simon's needs]
[Name the specific insight their audience is hungry for]

[Close: "Real conversation, not a pitch" + low-friction CTA]

Template:

That reframe — [echo their answer in one sharp line] — is where most
[programs/coaches/advisors] get it backwards. [One sentence on why].

I work with Simon Severino, who hosts The Sales Show — founders and
operators doing exactly this kind of work at depth. His guests have
included Marshall Goldsmith, Rory Sutherland, and Verne Harnish.
900+ episodes, 40+ countries.

Your angle — [their framework] + [their current project angle] — is
exactly what his audience is hungry for. [One sentence on who Simon's
audience is and the gap they have that this prospect fills].

It would be a real conversation, not a pitch. Interested? I'll connect
you with Simon directly.

Rules:

• First 1-2 sentences must engage with their actual reply — not a cold pivot
• Name their framework AND their current project in the invite
• "Real conversation, not a pitch" — always include this line for depth-first prospects
• CTA: "I'll connect you with Simon directly" — no calendar link, no form, no Calendly
• Never say "I'd love to have you on" or "our listeners would benefit" — both are about you

Phase 3 — After They Say Yes

Reply to the guest (send within 24 hours — include Simon's Calendly directly):

Great, [Name] — here's Simon's direct booking link, grab whatever works for you:
https://calendly.com/simonseverino/recording

Looking forward to the conversation happening.

Do NOT ask the guest for a booking confirmation screenshot — Simon sees it in his Calendly dashboard. Asking signals distrust and breaks the warm dynamic.

Message to Simon (send alongside a screenshot of the conversation thread):

Hi Simon, I've been running outreach for the podcast and just confirmed a guest for you.

[Full Name] — [Title], [Company]. [2-3 sentences: who they are, what they've built, current project].

Their angle: [their core methodology/framework in one sentence]. [Why this fits Simon's audience in one sentence].

They're booking via your Calendly: https://calendly.com/simonseverino/recording

Let me know if you need any background before the recording.

Attach: Screenshot of the full LinkedIn conversation thread so Simon has context.

Proven Example: Amos Schwartzfarb

Prospect: CEO Coach, Author of Levers and Sell More Faster, Founder of Retrocause fellowship

Phase 1 sent (Mar 26):

Amos, your reply actually made me rethink my question — you're right, "how do you prioritize everything" is the wrong framing if everything already fits into a small number of projects.

I went back to Levers after that. The W3 framework hit differently on re-read — specifically the part about narrowing your ICP feeling like you're limiting your market, when it's actually the opposite. I've seen so many founders resist that step because it feels like leaving money on the table.

Is that the core tension you're solving with the Retrocause fellowship? Getting founders to stop chasing breadth before they've proven depth?

Amos replied: "I would say the core item we are helping founders with is getting the deepest possible understanding of what makes their business work so that they can learn how to focus and stay more in control"

Phase 2 sent (Mar 27):

That reframe — understanding before optimization — is where most programs get it backwards. They hand founders a sales playbook before the founder knows what they're actually selling and why buyers choose them.

I work with Simon Severino, who hosts The Sales Show — founders and operators doing exactly this kind of work at depth. His guests have included Marshall Goldsmith, Rory Sutherland, and Verne Harnish. 900+ episodes, 40+ countries.

Your angle — W3 framework, repeatability before scale, and now Retrocause for the $500K–$5M window — is exactly what his audience is hungry for. Founders who are selling, but haven't done the deep diagnostic yet.

It would be a real conversation, not a pitch. Interested? I'll connect you with Simon directly.

Result: Amos replied "Sure" ✅

What Makes This Different From Standard Podcast Outreach

Pro Tips

• If they don't reply to Phase 1 in 7 days: comment substantively on their next post, then follow up
• The sharper your Phase 1 question, the more likely they reply — vague questions get ignored
• "Real conversation, not a pitch" is not filler — it directly addresses what depth-first prospects fear most
• Never run Phase 2 before Phase 1 gets a reply. The trust is the foundation.
• The best Phase 1 messages make the prospect feel understood, not just researched