What are the 1%s that have made Diary of a CEO the 2nd biggest podcast in the entire world?

Today I’m talking to the Head of Failure and Experimentation at Diary of a CEO and Flight Story about exactly that.
When Grace Miller started at Diary of A CEO in the social media team they had 100,000 subscribers, now just over 4 years later they have over 16 Million just on Youtube and Billions of views.

*_The episode was so good that we had to split it into two parts so you can actually implement what we talk about. If you want to hear the AI tools the DOAC team are using, which tools (and platforms) to use to grow your audience and the one thing that completely changed ALL Flight Story conversations make sure you’re subscribed or following because you won’t want to miss this. _*

You’ll hear

• 00:00:00 Why we got Grace Miller on the show
• 00:02:19 What changed when they implemented a Head of Experimentation & Failure and what you can learn from it yourself
• 00:03:58 The 1% Diary of A CEO do to make their podcast an experience (for listeners and guests)
• 00:05:45 What you can learn from Taylor Swift about podcasting
• 00:08:22 Where to start if you want to build a culture of experimentation
• 00:10:07 How to use end screens to get more views on Youtube
• 00:11:52 The three things the foundation of every great show has
• 00:12:58 How to make your podcast memorable
• 00:14:35 If you want new listeners to stay you need to do this
• 00:20:15 Should you have NEW topics and guests all the same time?
• 00:23:35 Why Diary of A CEO removed microphones
• 00:26:25 What Grace would do first if her first objective is to grow a podcast
• 00:28:58 The best social strategies for podcasting
• 00:30:43 What Grace and the Diary of A CEO team did to build community early on
• 00:34:26 Where you should focus in 2026
• 00:35:08 How to build a community even if you have ZERO followers
• 00:36:30 Using AI to help you grow your social media and podcast
• 00:38:18 The number of thumbnails Diary of a CEO tests and how you can see every single variation
• 00:40:20 The #1 Rule for creating thumbnails
• 00:41:42 Why just copying someone elses thumbnail doesn’t work
• 00:45:32 The best strategy for Youtube that most people don’t know about
• 00:50:27 Do shorts hurt your main channel?
• 00:51:22 How to get people to watch your long form content
• 00:54:40 What’s coming up next week

Follow Grace over at Grace Experiments on Instagram @graceexperiments https://www.instagram.com/graceexperiments/ and Grace Miller on Linkedin https://www.linkedin.com/in/grace-miller
Have a guest you want to hear from? Question you want answered? Send me a DM over at www.instagram.com/alyciachapman_ or https://www.instagram.com/howdoipodcast

What are the 1%s that have made Diary of a CEO the 2nd biggest podcast in the entire world? 

Today I’m talking to the Head of Failure and Experimentation at Diary of a CEO and Flight Story about exactly that. 

When Grace Miller started at Diary of A CEO in the social media team they had 100,000 subscribers, now just over 4 years later they have over 16 Million just on Youtube and Billions of views. 

The episode was so good that we had to split it into two parts so you can actually implement what we talk about. If you want to hear the AI tools the DOAC team are using, which tools (and platforms) to use to grow your audience and the one thing that completely changed ALL Flight Story conversations make sure you’re subscribed or following because you won’t want to miss this. 

You’ll hear
0:00 - Why we got Grace Miller on the show
2:19 - What changed when they implemented a Head of Experimentation & Failure and what you can learn from it yourself
3:58 - The 1% Diary of A CEO do to make their podcast an experience (for listeners and guests)
5:45 - What you can learn from Taylor Swift about podcasting
8:22 - Where to start if you want to build a culture of experimentation
10:07 - How to use end screens to get more views on Youtube
11:52 - The three things the foundation of every great show has
12:58 - How to make your podcast memorable
14:35 - If you want new listeners to stay you need to do this
20:15 - Should you have NEW topics and guests all the same time?
23:35 - Why Diary of A CEO removed microphones
26:25 - What Grace would do first if her first objective is to grow a podcast
28:58 - The best social strategies for podcasting
30:43 - What Grace and the Diary of A CEO team did to build community early on
34:26 - Where you should focus in 2026
35:08 - How to build a community even if you have ZERO followers
36:30 - Using AI to help you grow your social media and podcast
38:18 - The number of thumbnails Diary of a CEO tests and how you can see every single variation
40:20 - The #1 Rule for creating thumbnails
41:42 - Why just copying someone elses thumbnail doesn’t work
45:32 - The best strategy for Youtube that most people don’t know about
50:27 - Do shorts hurt your main channel?
51:22 - How to get people to watch your long form content
54:40 - What’s coming up next week

Follow Grace over at Grace Experiments on Instagram @graceexperiments and Grace Miller on Linkedin (https://www.linkedin.com/in/grace-miller-linked-in/?isSelfProfile=false) 

Have a guest you want to hear from? Question you want answered? Send me a DM over at  www.instagram.com/alyciachapman_ or https://www.instagram.com/howdoipodcast 

Watch the podcast on Youtube  - https://www.youtube.com/@HowDoIPodcast 

Natasha Willis has generated over $100 MILLION in revenue for her clients including Nike, Jenna Kutcher, Amy Porterfield, Russell Branson through her Instagram and DM strategies.

This is a masterclass on how to not only sell your product or service to your audience in a way that actually brings value to them - but also create an ecosystem for your podcast.

We chat about: 

🎙️The AI automations she’s using that’s brought in over $5million sales for one of her clients

🎙️Her exact strategy behind Amy Porterhouse’s Instagram funnel

🎙️Which channels have the highest conversion rates for podcasts

You’ll hear: 

0:00 - The number of followers you need to have before you can start making money off your content (it’s way smaller than you think)

2:50 - Natasha’s strategy for Amy Porterfield which would convert 50% of people onto their emailing list

6:23 - Is using AI for DMs going to impact the relationship you have with the audience?

8:23 - Don’t make this mistake with AI automations

11:47 - What else you could be using your DMs for

15:05 - Should you be integrating Chat GPT or other LLMS to help with your copy?

17:10 - Which channels have the highest rate of conversion for podcast + how to package your podcast like an offer

21:22 - Which is better: reels or carousels?

22:33 - Are your freebies beginning in the wrong leads? How to get in front of people who want to pay for your product or service

25:54 - How do you use freebies as someone with a high ticket offer 

28:27 - What Natasha and her clients are doing differently now versus 6/12 months ago

31:06 - How has people’s behaviour towards AI and automations changed?

33:03 - This business owner has generated over $5million sales from DMs

33:57 - How can people incorporate these strategies for other platforms like LinkedIn, YouTube, TikTok and X

37:10 - What podcast Natasha keeps coming back to and why

DM Natasha ‘ALYCIA’ to get the 8 Ways that You Can DM People on Instagram @natashatwillis (https://www.instagram.com/natashatwillis/).

Have a guest you want to hear from? Question you want answered? Send me a DM over at  www.instagram.com/alyciachapman_ or https://www.instagram.com/howdoipodcast 

Watch the podcast on Youtube  - https://www.youtube.com/@HowDoIPodcast 

You can have the best podcast in the world … but it’s a complete waste of time if no one can find you.

This week I’m auditing one of our listeners podcasts and the crazy part? I haven’t listened to a single episode.

Every change I talk about today is something that will change whether your podcast grows organically or not (and whether people love your show) and if you like this format and series let me know in the comments or over at @howdoIpodcast (https://www.instagram.com/howdoipodcast) and I’ll do another one and focus on the content instead. 

Have a guest you want to hear from? Question you want answered? Send me a DM over at  www.instagram.com/alyciachapman_ or https://www.instagram.com/howdoipodcast 

Watch the podcast on Youtube  - https://www.youtube.com/@HowDoIPodcast 

Most entrepreneurs wait until they have the perfect plan, the perfect branding, and the perfect "expert" status before they launch.

Katie Stevens didn't wait. She started her first marketing agency at 19, pitching to rooms full of middle-aged executives, and has since founded nine different businesses. From selling out live events for over 25,000 people to launching automated business models like Sprayed, Katie has built a massive personal brand by moving faster than her fears.

This episode is an absolute masterclass in the psychology of business, the importance of "pattern disruption" in your marketing, and why procrastination is the only thing truly standing between you and a global brand.

You’ll hear:

🎙️ The transition from solopreneur to "9-times founder" and the lessons learned along the way

🎙️ The "Three Cs" (Connect, Collaborate, Create) and how to bake community into every touchpoint of your business

🎙️ Why you need to treat your podcast (and your content) like a professional media outlet to cut through the noise in 2026 

You’ll hear:

0:00 - How Katie went from a 19-year-old founder to launching nine successful businesses

3:15 - The Three Cs framework: Connect, Collaborate, and Create

7:45 - How to interview high-level guests without the help of AI

12:20 - Why "yesterday's news" is your best friend when overcoming imposter syndrome

21:30 - The 3-second rule for hooks and why your "Hey guys" intro is killing your retention

29:55 - Understanding "pattern disruption" and the strategic placement of ads

37:20 - Why moving before you're ready is the only way to beat the "AI creators" to the punch

45:10 - Why live meetups and private forums are the biggest builders of business in 2026 

Have a guest you want to hear from? Question you want answered? Send me a DM over at  www.instagram.com/alyciachapman_ or https://www.instagram.com/howdoipodcast 

Watch the podcast on Youtube  - https://www.youtube.com/@HowDoIPodcast 

What if you could land your podcast in front of some of the biggest publications? Get a TV Spot? Or Even Land a Book Deal? 

Today we’re talking to former radio host, turned podcaster, author (and star on Big Brother) Heidi Anderson to talk about how she teaches her clients to become their own Kris Jenner.
Her clients have landed on hundreds of publications including the Today Show, news.com, The Daily Mail, Good Morning Britain and Mamamia and she’s got 5 very easy steps so you can too. 

You’ll learn:

• How to find the angle that makes journalists say yes 

• The one-sentence pitch that landed a client on national TV 

• What to say in your pitch (and your follow up) 

• Which publications YOU should pitch to in 2026

You’ll hear

Find Heidi over at IG @_heidianderson (https://www.instagram.com/_heidianderson/), Facebook (https://www.facebook.com/therealheidianderson/) and her website https://www.heidileeanderson.com/ 

Have a guest you want to hear from? Question you want answered? Send me a DM over at  www.instagram.com/alyciachapman_ or https://www.instagram.com/howdoipodcast 

Watch the podcast on Youtube  - https://www.youtube.com/@HowDoIPodcast 

We’ve landed podcasts on the charts with 300 downloads. 

Not 300,000 … just 300.

And if you’ve been posting consistently, adding CTAs, doing all the ‘growth hacks’ that the experts have been recommending but you’re still stuck. It’s not you. It’s the algorithm. 

Spotify, Youtube and Apple are all fighting for attention right now and they will reward and promote your content IF you optimise for these specific metrics. 

Have a guest you want to hear from? Question you want answered? Send me a DM over at  www.instagram.com/alyciachapman_ or https://www.instagram.com/howdoipodcast 

Watch the podcast on Youtube  - https://www.youtube.com/@HowDoIPodcast 

Most podcasters wait for "the right time" to launch, fearing they aren’t expert enough or that their voice doesn't matter.

Melissa Ambrosini didn't wait. She started with a simple desire to share her journey and has since built a global empire, reaching millions through The Melissa Ambrosini Show and her bestselling books. But behind the massive downloads and sold-out stages is a constant practice of mastering the inner critic that tells you you're not ready.

Still not convinced you can manage a massive show while staying grounded? Melissa shares how she manages the demands of a global brand while prioritising her family and her health, proving that "hustle" isn't the only way to the top.

This episode is an absolute masterclass in moving past the "imposter" phase, treating your podcast like a professional media outlet from day one, and the essential mindset shifts required to sustain a show for over 600 episodes.

We chat about: 

🎙️The transition from "the stage" to "the mic" and how to own your unique voice

🎙️The non-negotiable role of consistency in building a top-ranking global show

🎙️Building a sustainable production rhythm that prevents creator burnout 

You’ll hear: 

0:00 - The career pivot: How Melissa moved from professional dancing and acting into the wellness and podcasting space

6:42 - Why Melissa decided to start The Melissa Ambrosini Show and how it has evolved over the years

14:15 - How to keep showing up when the growth feels slow

21:30 - How to use AI without losing your magic

29:55 - What it actually looks like behind the scenes to produce a world-class podcast

37:20 - Melissa’s advice for podcasters who are afraid of what people will think

44:08 - How Melissa balances motherhood, writing, and hosting without losing her peace

53:12 - Future-proofing your brand: Where Melissa sees the future of podcasting and creative content 

Follow Melissa over at: https://www.instagram.com/melissaambrosini/ and https://melissaambrosini.com/

Listen to The Melissa Ambrosini Show on Apple (https://podcasts.apple.com/ae/podcast/the-melissa-ambrosini-show/id1196106699) or Spotify (https://open.spotify.com/show/4cBKCrx06MkdcinQNTbXI7).

Have a guest you want to hear from? Question you want answered? Send me a DM over at  www.instagram.com/alyciachapman_ or https://www.instagram.com/howdoipodcast 

Watch the podcast on Youtube  - https://www.youtube.com/@HowDoIPodcast 

He sent Gary Vee a message … and 30 minutes later got a job interview.

Zachary Owings was playing professional baseball for the Miami Marlins, watching hours of Gary’s content and one day took a chance.
He now works alongside Gary Vee, hosts the Real OShow with his brother Joshua and has hundreds of thousands of followers and millions of views across the podcast and youtube … but his advice for podcasters? It’s COMPLETELY different to what you’d expect.
Especially when it comes to guests. 

We chat about: 

🎙️How to build a podcast community that buys from you (not just listens) 

🎙️Whether YOU should have guests on your show 

🎙️What you need to include in your cold outreach if you want people like Gary Vaynerchuk to respond 

Listen to The Real O Show on Apple (https://podcasts.apple.com/us/podcast/the-real-oshow-podcast/id1634513051) & Spotify (https://open.spotify.com/show/51DacIVT9XnmaKnrvG4zCB) 

Or watch on Youtube here - https://www.youtube.com/watch?v=zyiN4V2yTfQ 

Follow Zachary & Joshua on Instagram here - https://www.instagram.com/therealoshow_/ 

Have a guest you want to hear from? Question you want answered? Send me a DM over at  www.instagram.com/alyciachapman_ or https://www.instagram.com/howdoipodcast 

Watch the podcast on Youtube  - https://www.youtube.com/@HowDoIPodcast

Most podcasters think they need thousands of downloads before a brand will take them seriously.

Madelyn from The Healthy Hustlers monetised within her first six months. And now she’s reached 4 million downloads across the podcast, and brand deals are her number 1 source of income 7 years later … but they’re not the brand deals you’ve heard about before!

Still not convinced? One of her clients landed a $1,000 brand deal with just 30 downloads per episode.

There is a way to approach brands when you’re a smaller podcast but hardly anyone ever talks about it!

This episode is a masterclass in how to show brands what you’re worth, how to price your deals and how to land partnerships before your download numbers look “impressive.”

We chat about: 

🎙️How to land brand deals before you have big download numbers

🎙️What most podcasters get wrong when pitching sponsors

🎙️How to make brands see the value in your show

You’ll hear: 

0:00 - How Madelyn built Healthy Hustlers to over 4 million downloads and why monetisation started way earlier than most people think

3:44 - How to start recording solo episodes when you feel awkward, nervous and like you’ve got nothing valuable to say

12:28 - What she’s learnt about podcasting after interviewing some of the biggest  names

14:44 - How to land bigger names on your show (even if your podcast isn’t “big” yet)

18:46 - The scripting strategy she used to get Kayla Itsines saying “I’ve never spoken about this before” on her show

21:33 - One of the first things Madelyn did that saw HUGE growth in her podcast

25:50 - Doing series with other people on your podcast: how to leverage guest’s audiences

30:58 - What it’s like signing to a podcast network and things you need to be aware of

35:08 - The kind of brand deals most podcasters overlook (and why small shows are more powerful than they realise)

38:44 - How to pitch your dream brands

40:44 - The most important thing you need to get big brand deals + how to find what brands you’re aligned with

44:48 - The kinds of ads you can actually place in your podcast

49:50 - How to price your podcast to brands even if you have a small audience

54:27 -  After 7 years of podcasting - how Madelyn keeps herself motivated to keep recording

58:18 - The podcast she loves right now and why she avoids consuming too much content in her own niche

Follow Madelyn over at https://www.instagram.com/madelyncarafa/ and https://www.instagram.com/thehealthyhustlers/ 

Listen to The Healthy Hustlers on Apple - https://podcasts.apple.com/au/podcast/the-healthy-hustlers-podcast/id1400257108 or Spotify - https://open.spotify.com/show/0JbdhahNuAtoJlp4TPSGDt 

Find your human design here (https://www.myhumandesign.com/).

Have a guest you want to hear from? Question you want answered? Send me a DM over at  www.instagram.com/alyciachapman_ or https://www.instagram.com/howdoipodcast 

Watch the podcast on Youtube  - https://www.youtube.com/@HowDoIPodcast