SPEAK LIKE A CEO

Every platform eventually turns on the brands that built on it. The leaders winning now aren't begging algorithms for reach – they're owning their audience directly.

Tyler Denk is doing exactly that. As CEO of beehiiv, he's built a $500K newsletter in five hours a week while running a $30M business with 110 employees across 15 countries. Before that, he was employee number two at famed newsletter Morning Brew, which sold for $75 million. 

He joins Oliver to unpack why storytelling is now your most important business asset, why your social following may be worth less than you think, and how the best leaders today are the ones who know how to communicate, not just manage. 

Learn why owning your audience is the most important move leaders can make right now.

⏰Timestamps

(00:00) Introduction 

(00:58) Why platforms are unreliable now 

(02:23) Power of Newsletters

(07:31) Why Storytelling is Key

(10:16) Founding beehiiv

(13:48) Leading Remote 110 Team 

(19:39) Creator & CEO Hybrid

(21:59) Customer Acquisition in AI Age

(25:02) Own Distribution 

(29:14) Transparency as a Superpower

(32:10) LinkedIn strategy and building a brand as CEO

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🔗LinkedIn

Host: https://www.linkedin.com/in/oliver-aust/

Guest: https://www.linkedin.com/in/tyler-denk/

📩Newsletter

Host: https://eo-ipso-comms.kit.com/profile

Guest: http://mail.bigdeskenergy.com/ 

📚Resources

• 21 Storytelling Frameworks: https://eo-ipso-comms.kit.com/21-storytelling-frameworks-with-oliver

• Become a Presentation Genius (Free Course): https://www.youtube.com/watch?v=3wJloFeNwBg

• Speak Like a CEO Academy: https://www.speaklikeaceo.academy/

📧 Email: [email protected]

🙌 This episode was produced by Podcast Boutique https://www.podcastboutique.com

💡 This episode’s supervising editor was Chelsea B. Olsen https://chelseabolsen.com

Most leaders avoid AI entirely or let it do all their work. Both are destroying their credibility.

In this episode, Oliver sits down with Allison Shapira, Harvard lecturer and author of AI for the Authentic Leader, to discuss why AI is actually making so many leaders worse communicators and leaders. She shares her frameworks and insights on how to write with AI without losing your voice, let it help with your biggest problems, and handle tough conversations.

You’ll learn what it really means to be authentic in an AI word, how the AI Authenticity Loop can help you maintain trust, , and how to get started using AI the right way.

Topics discussed:

Introduction (00:00)

How to use AI strategically (00:40)

The AI authenticity loop (03:35)

The definition of true authenticity - and where AI fits in (06:24)

How to protect trust while using AI (08:52)

When and how to use AI for difficult conversations (10:14)

Will AI make middle management redundant? (16:31)

What leaders are getting wrong about AI (18:41)

Three steps to start using AI as a leader (25:37)

How to overcome resistance and get your team on board (27:19)

Get access to Allison’s custom AI:
https://allisonshapira.com/ai

Grab a copy of Allison’s book, AI for the Authentic Leader:
https://allisonshapira.com/books/

Get the Presentation Planner Oliver uses with elite communicators: https://eo-ipso-comms.kit.com/presentation-planner

Want to work with Oliver and become a top 1% communicator? Join the Speak Like a CEO Academy! https://www.speaklikeaceo.academy/

This episode was produced by Podcast Boutique https://www.podcastboutique.com

Meetings, emails, conversations – the reason they all break down is the same: we get the first minute wrong.

Chris Fenning, author of The First Minute, literally wrote the book on how to get that first minute right. His frameworks are simple, but they fix the problems most leaders deal with every single day.

In this episode, you'll learn how to lead better meetings, write emails that actually get answered, and communicate your point before people tune out.

Topics discussed:

Introduction (00:00)

3 questions you must answer in the first minute - and why it matters (00:37)

The science behind the first minute (05:22)

The GPS framework for getting results (07:36)

How to recover when conversations go wrong (11:00)

The TPO framework for better meetings (12:38)

How to change communication culture in organizations (14:46)

When to replace a meeting with something else (18:34)

Who to include (and not include) in meetings (21:08)

Should you use AI to write your emails? (23:17)

How to set communication preferences within your organization (28:27)

How to structure emails that get replies (31:02)

The 10-second habit for clearer communication (34:59)
Where niceties belong in an email (36:15)

Connect with Chris Fenning:
https://chrisfenning.com/

Connect with Oliver:

 https://www.linkedin.com/in/oliver-aust/

Get the Presentation Planner Oliver uses with elite communicators: https://eo-ipso-comms.kit.com/presentation-planner

Want to work with Oliver and become a top 1% communicator? Join the Speak Like a CEO Academy:https://www.speaklikeaceo.academy/

This episode was produced by Podcast Boutique https://www.podcastboutique.com

Boards are now asking one question about every CEO candidate: are they coachable?

Scott Osman and Jacquelyn Lane, leaders of 100 Coaches, pull back the curtain on how elite coaching actually works: what makes someone coachable, what questions to ask, why coaching (almost) always justifies the price tag, and how long it takes to see results.

In this episode, they share why the best leaders are coachable and how you can build that skill yourself – plus, the one question every leader should ask themselves if they want to make a bigger impact.

Topics discussed:

Introduction (00:00)

Who actually needs a coach? (00:47)

Why coachability has become a CEO-level skill (01:51)

The origin story of 100 Coaches (04:54)

How to find the right coach for you (07:18)

The most common areas people need coaching (10:56)

How long does coaching take to work? (11:59)

How coaches use feedback to reveal your blind spots (13:30)

Should you suggest coaching to your boss? (18:39)

The leadership habits that silently undermine you (20:11)

Should a leader also be a coach? (22:18)

The openness framework: how to become more coachable (24:36)

Will AI replace executive coaches? (30:51)

Scott and Jacquelyn’s best communication advice (33:47)

Learn more about 100 Coaches:
http://100coaches.com/

Grab Scott Osman and Jacquelyn Lane’s book:
https://becomingcoachable.com/

Subscribe to Scott’s newsletter on LinkedIn:
https://www.linkedin.com/newsletters/best-insights-from-100-coaches-6613518216260050944/

Get the Presentation Planner Oliver uses with elite communicators: https://eo-ipso-comms.kit.com/presentation-planner

Want to work with Oliver and become a top 1% communicator? Join the Speak Like a CEO Academy and sign up for the FREE webinar! https://www.speaklikeaceo.academy/

This episode was produced by Podcast Boutique https://www.podcastboutique.com

Get the Presentation Planner: https://eo-ipso-comms.kit.com/presentation-planner

Most leaders spend hours preparing presentations that get mediocre results. They stare at PowerPoint, fill slides with bullet points, and still struggle to connect with their audience.

This comprehensive course reveals the exact system Oliver uses with CEOs and founders to cut preparation time in half while doubling impact. You'll learn the three-step framework elite communicators use to plan, practice, and present with confidence.

Whether you're pitching to investors, presenting to your board, or leading your team, this course will transform how you communicate. You'll discover how to structure any presentation in minutes, craft messages that stick, and deliver with the confidence of a top 1% presenter.

Topics discussed:

The objective: becoming a top 1% presenter (00:00)

Why presentations matter for leaders (02:15)

The three P framework: plan, practice, present (05:30)

Seven deadly sins of presenting and how to avoid them (08:45)

How to make the audience care: the 90% test (14:20)

Choosing the right structure for any presentation (19:35)

Crafting simple, effective messages that move people (25:10)

The killer opening line and ending with impact (31:45)

Why storytelling beats facts and logic (37:20)

Creating slides that support your message (43:15)

Handling questions, interruptions, and objections with grace (49:30)

Body language: posture, hands, and facial expressions (54:40)

Voice mastery: the five Ps of vocal variety (61:25)

Eliminating filler words and embracing the pause (67:10)

The BMW method: staying calm and confident under pressure (72:35)

Bringing energy and passion to every presentation (78:50)

Your action plan: joining the top 1% (83:15)

Want to work with Oliver and become a top 1% communicator? Join the Speak Like a CEO Academy: https://www.speaklikeaceo.academy/