The hardest part about making a podcast
Asking is free, so why is it so hard? Also: quitting your job for YouTube, AI doom, and a criminal duck.
I nearly quit my podcast. Not because I didn’t like making it, I’ve loved the conversations I’ve had and the people I’ve met. But there was one part I hated so much it almost stopped me entirely: asking people to come on.
Logically, I knew the worst that could happen was they’d say “no” or just not reply. And meanwhile the upside was amazing, I’d potentially get to meet and talk to someone I really admire!
Yet still the fear and awkwardness of asking almost shut me down completely.
To borrow a line from a friend: salespeople get paid a lot because they’re willing to face rejection hundreds of times a day.
What finally nudged me back into action was rereading Million Dollar Weekend by Noah Kagan. In the book, he gives the reader the “Coffee Challenge”: the next time you order a coffee (or anything), ask for 10% off. If you’ve never done sales or outreach before, that probably made you cringe.
For the record, I still haven’t done it. But I started my own version: asking 2-3 people every week to come on the podcast. I now have over 10 guests lined up!
Whether it’s asking for feedback on your project, for a spot on someones calendar, or a discount on your oat milk latte, it turns out it’s not about getting a ‘yes’ 100% of the time, it’s about feeling the awkwardness and doing it anyway.
🎤 On the pod: From corporate to creator, life as a full-time YouTuber with @tapiocapress
I just published an episode with Evelyn, aka tapiocapress, a former tech worker who left the 9–5 to pursue YouTube full-time. She now has over 70,000 subscribers and makes beautiful, reflective videos about creativity and life.
Publishing this was the perfect reminder for me to just go ask. When I first reached out to Evelyn, I didn’t even have a name for the podcast yet. But I asked, and she said yes. That one message led to a great conversation and a new connection.
In the episode, we dive into quitting the 9–5, building an audience from scratch, and figuring things out in public, with all the doubts and learning curves that come with it.
💎 Recent gems
The Arc browser is dead. A sad one for me. I switched to Arc 6 months ago and loved it, but the team just announced they’re shifting focus to their next project, an “AI browser” called Dia. Arc will still get security updates, but development has stopped. If you like clean interfaces and clever shortcuts, it’s still worth a look.
AI 2027. Part retro video game, part “choose your own adventure,” this is a bleak but brilliant research-backed look into possible AI futures. Click around, explore branching timelines, and see how it might all go right... or very wrong.
This Is What a Digital Coup Looks Like. “Privacy is power”. Carole Cadwalladr returns to the TED stage after being sued into oblivion and warns about the rise of the broligarchy and techno-authoritarianism. I also just found out she has a great Substack newsletter.
On a lighter note, “Case quacked: Flying duck caught by Swiss speed camera is repeat offender” might be my favourite headline ever.
VoicePal (iOS, Android): An “AI ghostwriting” app from Ali Abdaal. It’s essentially a voice memos app that cleans up your thoughts into usable text. I’ve been trying it again lately, and honestly sometimes it’s just easier to think out loud than to write.
Brandon Sanderson’s Writing Lectures 2025: Not new, but if you’re a wannabe writer (like me) and a huge Sanderson fan (also me), this lecture series is gold. I’m about halfway through and loving it.
See you in a few weeks,
— Mike.