The Newsletter Nerd Show

Sophie Cross is one of the kindest and savviest people I’ve had the privilege of knowing. And if you aren’t connected with her already, I highly recommend you correct it right away and give her a follow!

An entrepreneur, writer, editor-in-chief, playlist connoisseur, advocate for freelancers, lover of vans, and all-around badass, Sophie shows up in numerous ways for the community and has several newsletters under her belt including:

• The now-retired Thoughtfully
• The Dunker by Freelancer Magazine
• And the newest star in the block, Make It Monday

At the time of recording this episode, we delved deep into the Thoughtfully newsletter.

Tune in to hear Sophie talk about her life in the van, crazy business ideas, navigating the freelancer life, having a song for everyone she meets, the importance of community and so much more!

This is episode #19 on the Newsletter Nerd Show. 

Meet Fio Dossetto.

A lover of em dashes and sticky notes, she writes the contentfolks newsletter to help marketers create content that truly serves the audience.

When she’s not writing the newsletter, she works on other interesting projects like this. And for a kid who always found joy in words, the opportunity to create a comic book about email delivery dogs and having ‘spread joy’ as a success metric is a wild dream coming true!

In this episode, we talk about opinionated editors—em dash is THE best punctuation mark of all time, don’t fight me—finding joy in words, giving yourself permission to be silly, unlearning things as a newsletter creator and a whole lot more!

Dig in by hitting the play button!

Find out more about the Newsletter Nerd Show here - https://www.thenewsletternerdshow.com/ 

Time Stamp:

00.40 - Why em dashes are the best punctuation marks of all time

02.14 - What Fio found joy in as a child

03.28 - A project where spreading joy was the goal

06.24 - Silly mockup pages to fuel creativity

09.10 - How contentfolks happened

11.30 - Going from a weekly newsletter to a fortnightly newsletter (+ Ann Handley)

16.02 - How the sticky note representation came to life

18.21 - One thing that Fio had to unlearn mindfully as a newsletter creator

20.36 - Not playing the numbers game

22.35 - What success means for contentfolks

24.14 - If Fio could only one newsletter for the rest of your life, which one would it be?

27.27 - Something Fio considers a newsletter sin

28.39 - The Reading Room

35.35 - Fio plays Have You Ever

Because Salman Ansari was once in your shoes too.

Today, helping people embrace the polymathic mindset is one of the key things he tries to achieve with his newsletter Quick Brown Fox, where he explores creativity, philosophy, fables, and more.

What truly makes Salman’s work soul food for every creator is that by sharing his story with you, he gives you the reassurance that you’re not navigating the creative world alone.

Not to mention the sense of calm that washes over you as you come across his work.

To learn more about the Newsletter Nerd Show, head to https://www.thenewsletternerdshow.com/

Time Stamp:

0.42 - Gripe with the phrase 'A jack of all trades is a master of none'

1.59 - Specializing Vs exploring multitudes

9.57 - How the pandemic has redefined careers

14.08 - What being a polymath really means to Salman 

17.57 - Being protective of playful experiments

22.08 - Energy management when you're pursuing multiple interests

27.52 - The importance of resting and recovery

29.25 - Where the Quick Brown Fox fits in on Salman's journey

38.43 - Not taking unsubscriptions personally

40.49 - What Salman thinks is a newsletter sin

42.02 - The Reading Room (where Salman reads an excerpt from his newsletter)

44.31 - Salman's upcoming book Wandering Spirit 

52.09 - Have You Ever? (where Salman answers Yes or No questions about his newsletter)

A long lost relative of one Mrs Pepperpot, Amy Nolan—who writes the Doodle Digest newsletter—has been doodling since she was a kid.

"My dad would make sure that I always had plain papers to doodle on," she smiled.

From pillowcases and shoes to her dog Barry, Amy has experimented with a wide range of canvasses for doodling.

Today, Amy also creates commissioned business illustrations that I highly encourage you to check out!

In this episode, Amy and I unpack a lot about baking disasters, creativity, flipping the narrative of your newsletter, taking your art seriously, not second-guessing yourself or your audience, handling unsubscriptions, and a whole lot more.

And consider yourself warned: there's a LOT of giggling as well.

This is episode number 16 on the Newsletter Nerd Show. Find out more at www.thenewsletternerdshow.com

The year is 2011 and Rohit Srivastav has been reaping karma points on Quora, Reddit, and Facebook. On the former two by leaving helpful answers and on the latter by, well, running a meme page.

Little did he know that his love for writing and satire would lead to encounters with pioneers in Indian SaaS (Software as a Service) and would eventually lead him to marketing.

Today, Rohit runs a newsletter—Figuring it out—where he shares lessons that he wished he knew as a young marketer.

He also moonlights as a poet, screenwriter, and an A+ human being.

That, apart from making Twitter and LinkedIn a much better place with his humor.

This episode on the Newsletter Nerd Show is about mental frameworks, not taking yourself too seriously, navigating roles, and everything you wish you knew as a young marketer!

To learn more about the Newsletter Nerd Show and never miss out on an episode, head to https://www.thenewsletternerdshow.com/

Dave Harland— who writes The Word—has always been a messabouter™ (his words, not mine). From doing impressions of teachers in school to always leaving his nan’s house through the window, his messabouting has shaped who he is today.

But I don’t blame him.

If my family’s way of expressing love meant taking a humorous dig at each other in a friendly way, I would’ve turned out the same.

When Dave joined me on the Newsletter Nerd Show, he upheld the honour of the Harland clan by leaving me in stitches!

We talk about made-up words, exploding faces, catching people in awkward situations, copywriting, humour being a connector instead of a disruptor, and a whole lot more in this one.

This is episode #14 on The Newsletter Nerd Show.

To never miss out on The Newsletter Nerd Show, consider subscribing on your favourite podcast player and on https://thenewsletternerdshow.substack.com/

But Dan Nelken is not most people.

When Dan realized job promotion announcements were rampant on LinkedIn, he decided to have some fun too!

And that’s when he gave himself the title of Chief Creative Ding-Dong! No kidding. You can go ahead and check out his LinkedIn profile right now.

While this title is a clear indicator of Dan’s creativity, he didn’t embrace creativity from the start.

“I came late to it myself,” he said when he was on the show.

Today, he runs a newsletter called A Self-Help Guide for Creatives and inspires creative people across the world.

Tune in to see how a non-existent course led Dan to create his newsletter, what he thinks of creative habits vs goals, how the word ‘gigglemug’ was casually slipped in, and a lot more!

This is episode #13 on The Newsletter Nerd Show.

To never miss out on The Newsletter Nerd Show, consider subscribing on your favourite podcast player and on https://thenewsletternerdshow.substack.com/

Time Stamp:

0.41 - On being the Chief Creative Ding-Dong

2.44 - Life while growing up and what influenced his creativity

5.04 - Creative habits over creative goals

7.09 - Early morning sessions and other creative habits

11.09 - What he values more as a creative - control or certainty

13.00 - How a non-existent course led to launching his newsletter

16.06 - Delivering value in as few words as possible

17.28 - A recent experiment he ran with his newsletter

20.25 - Role of a social community in your journey

21.34 - Responses from readers

23.54 - Handling unsubscriptions

27.13 - A newsletter sin

28.49 - Reading Room

33.34 - Have You Ever?

Gemma Higgins is the kind of person who’ll send people otters in the post to express her love. She’s also the kind of person who’ll make you laugh your guts out because of her quick wit.

And her newsletter—Rosé Hand Files—offers the best of both worlds. Since Gemma loved to write satire, this was her excuse to answer ridiculous questions over a glass of wine. At the same time, she also wanted her readers to feel connected and hold on to the words she brewed over a different rosé each week.

But what began as a silly and satirical newsletter soon saw readers come in with questions so deep that Gemma needed to sit with these questions for days—and sometimes weeks—together before she attempted to answer them. And it was no easy task.

This conversation is raw, personal, and all sorts of beautiful

I did not ask her about experiments she runs with her newsletter or even the beloved ‘what do you consider a newsletter sin?’ Because when she began answering how the newsletter changed her life, I knew that’d give me everything I needed to know.

This is episode #12 on The Newsletter Nerd Show.

Jay Acunzo writes Playing Favorites—a weekly newsletter to help people create stuff that matters—and answers these questions on this episode. 

We also unpacked a lot from creativity equations and crap pedestals to cliffhangers and storytelling techniques. 

On Jay's content spectrum of transactional to transformational, this is 100% transformational. Dig in :)

To never miss out on The Newsletter Nerd Show, consider subscribing on your favorite podcast player and on https://thenewsletternerdshow.substack.com/

Time Stamp

0.43 - Creativity is not bigness

1.31 - If creativity had an equation

3.41 - Crap pedestals and the legend of the creative genius

9.15 - Creativity is a mess

11.20 - Mr.Schread, constraints, and creativity

16.50 - What it takes to become someone's favorite

18.05 - Building blocks to creating work that matters

21.07 - Transactional vs Transformational work

25.15 - Matching delivery with promised value

26.20 - Shoutout to the incredible Ann Handley

27.25 - Vetting ideas for the newsletter

28.30 - Why "think outside the box" is incomplete

29.30 - What to do when you're frustrated with something

30.48 - Where Playing Favorites fits in Jay's journey

31.59 - First edition of the newsletter

34.28 - An ode to the asterisk

36.18 - Using tension in storytelling

37.09 - Open loops in stories

38.34 - Cliffhangers vs clickbaits

42.15 - What not to chase in the newsletter world

43.51 - The world needs compasses not maps

45.48 - Reading Room

53.54 - Have You Ever?

Alex Wieckowski, the face behind Alex & Books—a newsletter for book recommendations, summaries, and reading tips—is convinced that if you’re really lucky, books will occasionally call out to you. And when they do, you’ve gotta listen to the voice.

Alex is a voracious reader, writer, podcaster, and book wizard! And if there’s one thing you take away from his story, I hope it’ll be the power of serendipity and trusting your intuition (that’s actually two things, but nvm).

This is episode #10 on The Newsletter Nerd Show.

Hit that play button below to dig into the good stuff!

Show Notes:

0.33 - Alex in the Hotseat

2.20 - How a bike crash led to launching Alex & Books

3.22 - Identifying there's a need for book recommendations

3.47 - A fun exercise involving a 2017 photograph

4.45 - How life as a person & creator has evolved since then

5.18 - The 2 C's framework to choosing books

6.11 - Why you should judge a book by its cover

6.42 - When to quit reading a book

7.57 - Why a newsletter?

8.40 - The most and least favourite part of running a newsletter

9.30 - Repurposing newsletter content

10.19 - What to know before launching a newsletter

11.17 - A newsletter sin

12.00 - The Reading Room

14.02 - Have You Ever?

So it was no surprise when Hua Shu—creator of the FontDiscovery newsletter—said that Papyrus or anything resembling Papyrus is the font she’ll never use even when all hell breaks loose.

A rebellious spirit from the start, design—fonts in specific—gave Hua a space to break rules and channel her rebelliousness. Today, she is a designer, coder, design professor, Google Font contributor, and a full-time font nerd!

Hit that play button below to enjoy a 27-ish minute glimpse at the world of typography - through the eyes of a clay-loving-kid who had no idea she’d fall in love with fonts when she grew up.

This is episode #9 on The Newsletter Nerd Show.

Drop me a line here if you want to see yourself or someone you know on the show!

(THE Cole Schafer, who runs Honey Copy and along with it, three newsletters - Sticky Notes, Stranger than Fiction, and Chasing Hemingway)

At 2.30 am, there's a thin line between dreams, illusion, and reality. And this sure seemed more like the former two than the latter.

“She’s cute,” Cole spoke in a baritone that still hasn’t escaped my ears, when Pebbles unexpectedly jumped in to claim her spotlight, bright-eyed and bushy-tailed (quite literally).

A sheepish grin and multiple failed attempts at shoving a canine tail away from my face later, the conversation you’re about to witness began.

This is episode #8 on The Newsletter Nerd Show.

And that’s precisely the message Kushaan Shah’s newsletter—The Marketing Mind Meld—tries to drive home. The about section of the newsletter reads Musings on marketing and human behaviour that will blow your mind 🤯. 

Read one edition and you’ll know this is not yet another snake oil marketer making tall claims but is someone who knows the depth of what he’s saying.

This is episode #7 on The Newsletter Nerd Show :)

Time Stamp

1:54 - The Story Unfolds

24:44 - Reading Room

29:13 - Newsletter Have You Ever

For Anirudha Basak, time slows down in his ancestral city of Kolkata (previously Calcutta). A place where people take their own sweet time for banter and tea, it is the city’s āddā that he fondly reminisces.

Āddā is a salon-like gathering at which thoughts and persuasions of the day could be discussed in a good-natured, if sometimes vociferous, manner.

After he signed and sealed his love letter to the cultural capital of India, Anirudha went on to tell me about his banking newsletter - Bank on Basak. What began as a news repository for his personal reference soon became a trusted source that simplifies the Indian banking landscape for the rest of us.

From the mistakes that young people make when investing to the discipline of consistency, this conversation branches out and runs a wide course, not unlike the Hooghly river.

Hit that play button to dig into the conversation!

Time Stamp

0:41 - The Story Unfolds

24:08 - Reading Room

29:16 - Newsletter Have You Ever

When I’m 80 years old and sitting in my rocking chair, my grandkids will ask me how I once managed to remain sane amidst all the noise on Twitter and found its warm, happy corner. And I’ll tell them all about the incredible List Lady™ aka Chantelle Marcelle.

Loved for her marketing chops, Twitter list-making skills, and ability to hype up fellow marketers and creators, Chantelle writes a fortnightly marketing newsletter that caters to novices and veterans alike.

Here’s her elevator pitch:

Tune in to episode #5 of The Newsletter Nerd Show to hear all about Chantelle’s newsletter, her take on the Oxford comma, the role of communities, being inclusive, and the quality of curation, among others.

Luciano Vizza’s newsletter on food and cooking—Salt Sear Savor—is served hot every week and is a complete treat!

But it comes bearing a warning - If you’re looking for a traditional step-by-step, hand-me-the-recipe-in-a-book kinda newsletter, this isn’t for you.

However, if you’re looking for one that dices the “why” behind every recipe, sautés anecdotes (there’s a really good one about pasta🍝), and garnishes with puns (*internal screaming*), Salt Sear Savor is just the one for you!

This is episode #4 on The Newsletter Nerd Show. 

Sairam Krishnan is one of those people and says his idea about travel, reading, and writing involves a lot of thinking about place.

A reader, writer, and marketer, Sairam runs two newsletters—The CMO Journal, one for the trying, thinking marketers and East Coast Road, a space for creative, personal pieces. He’ll always be someone I look up to because of his sheer dedication towards his craft and even simply as a human being.

So, when he agreed to join me on The Newsletter Nerd Show, I knew I was in for a memorable conversation :)

This is episode #3 on The Newsletter Nerd Show!

Today's smart 🍪award goes to the newest guest on the Newsletter Nerd Show - Ankita Tripathi, who runs The Sunday Grammarphones newsletter!

"I was appalled by my brother's entire lifestyle because he was a successful writer," she began after we had settled into our virtual squares.

But thanks to him, what followed was a newly found passion for poetry and grammar. Several years and one *cough* viral LinkedIn post later, she began offering valuable grammar sessions.

This is episode #2 on The Newsletter Nerd Show. Sit back and enjoy :)