How to Write for a Living

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Season 5, episode 5 is here!

Liam Austin has been on Substack for about five months, and you’ve probably already seen his face all over it.

Before that, he spent a decade running online businesses, grew the biggest small business group on LinkedIn, and hosted 18 virtual summits. Now he’s running the Substack Success Summit, and I’m one of the speakers.

We talked about getting in early, building authority fast, and why he’s changed his mind about one of the biggest growth questions out there.

What we covered:

- How a LinkedIn group Liam started in 2008 grew into the biggest one for small business owners, mostly thanks to a few well-chosen words.

- The first summit he ever ran, with 35 speakers and 15,000 registrations, and what happened the day the ticket sales stopped.

- Why Substack reminds him of Instagram back when there was no algorithm, and what that means for anyone arriving now.

- The content pyramid he uses to turn one live video into a year’s worth of posts, notes and clips.

- The podcast pitching problem he built Talks.co to solve, after hosts told him they bin most requests unread.

- Why he’s recently changed his mind on whether it’s better to be a host or a guest.

- His one action for the moment you finish listening, and the number of people he says to message.

Go and subscribe to Liam’s publication, and grab your free ticket to the Substack Success Summit.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

Season 5, episode 4 is here!

Ashley Evans spent years devouring every book on creative resistance she could find, and still couldn’t bring herself to share her writing. Then a title gave her permission.

Wannabe Wisdom, the diaries of a fake guru, is now three years and around 100 essays deep. She’s also a former actor, a hypnotherapist, a yoga teacher, and someone who has been murdered on screen in more creative ways than most.

This was a warm, thoughtful conversation with plenty for anyone who has ever thought, “who am I to say this?”.

What we covered:

- How a writing workshop of over 100 strangers dwindled to five, and why those five gave Ashley the name that freed her to write.

- The award she won in 2008 for the best death in a horror film, and why she won’t tell you where to find it.

- The tools she used to quiet her inner critic, including a book on parts work she’d recommend to anyone.

- The small punctuation choices that carry most of your personality, and why you’re probably funnier in person than on the page.

- How she decides whether something is too personal to publish, and the gut check she uses right before it goes out.

- The surprising story behind how Mary Shelley came up with Frankenstein, and what it says about creative blocks.

- The note she wrote at 100 subscribers that went viral, and the image that changed how she felt about a small audience.

Go and subscribe to Wannabe Wisdom, and if you’re a paid subscriber, keep an eye out for her new co-working sessions.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

Rob Riker has been on my radar for almost a year, popping up in comment sections all over Substack.

This live was the first time we’d ever properly spoken. He’s built coaching businesses on Twitter, watched that platform change under his feet, and rebuilt on Substack around the one skill he’s most passionate about, which is building relationships. The chat was buzzing from start to finish.

What we covered:

- How Rob went from a social skills blog that barely made money to a coaching business that let him quit his nine to five, and why he pulled the offer when Twitter changed.

- Why he thinks Substack has gone back to the way Twitter used to work, and what that means for who sees your notes first.

- The simple reason adults struggle to make friends, and how the same problem plays out in your comments section.

- His go-to move at a conference or party when you don’t know a soul, and why he skips the coolest people in the room.

- The three keys to building relationships on Substack, and the one creators drop just as things start going well.

- Why he deliberately seeks out writers with ten subscribers, and the maths that makes it worth it.

- Where he thinks the internet is heading as bots multiply, and the in-person bet one of the biggest names in online business is already making.

Go and subscribe to Rob’s publication on Substack and say hello in his comments. He’ll almost certainly say hello back.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

➡️ NEW FREE TRAINING: Are you failing, or are you just early? New free 38-minute training on the six signals that show you the difference. Comes with a downloadable scorecard so you finish with a concrete number, not just a feeling. Watch it here.

Season 5, episode 2 is here!

Drew English and I had never spoken before this live. We’d only traded messages, and it all began with a short video from him with nothing to sell attached. He’s a self-taught cinematographer, a former wannabe rock star, and the host of the No Set Path podcast. He talks about career chaos with total calm. What a great chat!

What we covered:

- How Drew went from wannabe rock star to Apple store employee to working cinematographer, with a used camera, YouTube University and a $5,000 summer job in the middle.

- The podcast he started out of boredom in a basement during COVID, and the studio it grew into that he never has to market.

- The simple message that got him into my DMs, and the one part he found hard about sending it.

- Why he thinks plenty of people building a personal brand are actually building something else in disguise.

- What happened to a six-figure cinematography career, and the hybrid way he’s rebuilding around the life he actually wants.

- How he weighs paid work against showing up online, and the one thing that always comes first.

- The sci-fi worlds, the surprising Paris film and the vintage hobby he uses to switch off, plus the reassuring thought he left us with.

You can find Drew at No Set Path on Substack, where he also hosts the podcast of the same name.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

➡️ NEW FREE TRAINING: Are you failing, or are you just early? New free 38-minute training on the six signals that show you the difference. Comes with a downloadable scorecard so you finish with a concrete number, not just a feeling. Watch it here.

Season 5, episode 1 is here!

Virgil Brewster blows up launches for a living. He built a course business to seven figures with two partners, sold it, drifted into semi-retirement, and then got pulled back in when people kept asking him for help. He is easily the most energetic guest I’ve had on, and this one flew by.

What we covered:

- The story of Virgil’s very first online payment, back when he ran a boutique personal training business in Ibiza, and why he was convinced it had to be a scam.

- What that first dollar does to your brain chemistry, and the two-second window of pure magic before your head starts chasing the next one.

- How he balances raw ambition with being content where he is, including the millionaire at an event who taught him more than he expected.

- His honest answer on avoiding burnout, from doing one task a day to the slightly terrifying activity he uses to quiet his mind.

- Why he puts 5 to 10 percent of his income into learning, and the decade of trying to DIY it all before that penny dropped.

- The two mistakes he sees people make with every launch, and why charging money for something half-built is the smartest thing you can do.

- His glass-half-full take on where the creator economy is heading, and the one-liner he left us with that’s worth writing on your wall.

Go and subscribe to Virgil’s publication, The Launch Room, and follow along with what he’s building.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

➡️ NEW FREE TRAINING: Are you failing, or are you just early? New free 38-minute training on the six signals that show you the difference. Comes with a downloadable scorecard so you finish with a concrete number, not just a feeling. Watch it here.

The Season 4 finale is here!

No guest this time. Just me and a shorter solo episode to close out season four. I answered some listener questions about podcasting and going live, gave a behind-the-scenes look at where the podcast is at, and walked through the changes coming next season. I even discovered a feature live on air that I had no idea existed…

What I covered:

- Where my podcast actually stands after two years, including the download count Substack quietly lopped over 20,000 off overnight.

- Why my episode numbers look like I’ve recorded 421 of these when the real figure is nowhere near that.

- The biggest change for season five, and why the recordings are opening up to everyone instead of just paid members.

- The new perk paid members get, which means your question gets asked even if you can’t make the live.

- My honest answers to listener questions on echo, cheap mics, and recording outdoors without it sounding like a wind tunnel.

- Why I still find solo lives hard even now, and the simple fix that takes the pressure right off.

- The evergreen traffic source I keep banging on about, and the feature I only realised existed halfway through this very episode.

Season five kicks off next week with a cracking guest lined up. If you’re a paid member, keep an eye out for the prompt to send questions in advance, and if you fancy pitching yourself or someone else as a guest, my inbox is open.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

➡️ NEW FREE TRAINING: Are you failing, or are you just early? New free 38-minute training on the six signals that show you the difference. Comes with a downloadable scorecard so you finish with a concrete number, not just a feeling. Watch it here.

Season 4, episode 21 is here!

Yuvika Iyer joined Substack four months ago with no niche, no plan, and a background in recruitment she wanted to leave behind. She’s now closing in on 700 subscribers, has sold a product she built almost by accident, and did her very first live for this conversation (and she was brilliant!).

What we covered:

- The simple 30-minute daily routine Yuvika credits for most of her growth, and why she supported other writers long before anyone was reading her.

- What happened when a writer with more subscribers sent her a cruel DM, and how the note she wrote in response turned everything around.

- The small analytics frustration she grumbled about that became a product, with 16 sales in the first 24 hours despite never having sold anything online before.

- Why she brought a coffee shop mindset to the platform, and what showing up at the same time every day actually does for you.

- Her take on positioning, and the one thing most creators skip that keeps them stuck writing to nobody.

- Where she goes to find out what readers really struggle with, and why she does it by hand instead of handing it to AI.

- Her golden nugget on why done beats perfect every time, and the modest revenue goal she’s quietly chasing by December.

Go and subscribe to Yuvika’s publication, The Quiet Creator, send her a DM, and check out her Gumroad tool while you’re at it.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

➡️ Are you failing, or are you just early? New free 38-minute training on the six signals that show you the difference. Comes with a downloadable scorecard so you finish with a concrete number, not just a feeling. Join here.

Season 4, episode 20 is here!

Ryan Maxwell and I have been having deep conversations for the best part of a year now, so it was about time we did one on the record. Ryan writes Chasing Maximus, and his whole journey is about working out how you became who you are and what comes next.

He built everything he thought he was supposed to want, watched it start to crumble, and has spent years since then digging into why. This was an honest, thoughtful conversation (as it always is with Ryan).

What we covered:

- The realisation midway through his corporate career that changed the whole direction of his life.

- What Ryan calls his two-by-four moments, and how to spot the warning signs long before life knocks you flat.

- Why the pressure he felt for years was never actually coming from where he thought it was.

- The difference between fitting in and belonging, and why sanding down your edges attracts the wrong people.

- What it really takes to tell someone a hard truth without crushing them, and why nice is not the same as kind.

- The line Ryan draws on how much of himself to share, summed up in one phrase about scars and open wounds.

- His golden nugget on why we mistake our adaptations for our personality, and the software update most of us never install.

Go and subscribe to Ryan’s publication, Chasing Maximus, and if you ever get the chance to have a proper conversation with him, take it.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

Season 4, episode 19 is here!

Dr. Taylor Francois trained as a lawyer, passed the California Bar, and then spent years building companies and teaching people how to actually use social media. She landed on Substack less than four months ago and has already crossed 32,000 subscribers. Behind the numbers is a story about burnout, a wake-up call she never saw coming, and a completely different way of working. This was a brilliant one.

What we covered:

- How Dr. Taylor grew to 32,000 subscribers in under four months, and the one thing she brought from every other platform that made it happen so fast.

- Why honing in on your zone of genius beats stacking up offers, and the reason spreading yourself thin is what keeps you stuck at the same revenue ceiling.

- The simple exercise she gives anyone trying to work out who they should actually be selling to.

- Her take on going all in on one platform versus being everywhere, and the 30-day test she swears by.

- The four-day weekend she guards fiercely, and the daily routine that starts at 5am for one very specific reason.

- Why she cut her output right down and started growing faster than ever, plus the signal that tells her burnout is creeping back in.

- The lunch that never happened, and the last thing a mentor said to her that made her burn down her whole business model and start again.

Go and subscribe to Dr. Taylor’s publication, Solo Millions, where she writes about building a big business on your own terms without the burnout.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

Season 4, episode 18 is here!

Suzanne Taylor-King Suzanne Taylor-King has started six companies, had two exits, and racked up many years of hard-won lessons along the way. These days, she’s less interested in growth for its own sake and more interested in building a business that hands you your life back. This was a cracking conversation, full of advice that runs against the grain of almost everything else out there.

What we covered:

- The paper round scheme Suzanne ran at 12 that got her in trouble with her parents, and the lesson about leverage she has never forgotten since.

- Why she quit a safe career at 23, drove across the country with no phone and a paper map, and accidentally found her way into business.

- The two mistakes she sees new entrepreneurs make again and again, and the question about money she asks that tends to stop people in their tracks.

- What happened when she hit her big income goal in three years, and why it nearly cost her everything that mattered.

- Why she now deletes things off her calendar without mercy, including a community bringing in real monthly money, and the counterintuitive idea behind it.

- How she thinks about the people around her in circles of ten, a hundred, and beyond, and where she would start if she had to build it all again today.

- The coaching scandal she’s watched unfold that tells you exactly where the industry is heading, and what people actually want to pay for now.

You can find Suzanne at The Idea Lab.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe