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

If you’ve always had multiple interests and are convinced that you lack the focus to specialize in a particular interest, you should probably (really) hit the play button right now! 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/

Most people who work independently confine themselves to titles like ‘freelancer’ or ‘consultant’. 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 <3 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.

If creativity is not bigness, what is it? What does it take to create someone's favorite work? How is the asterisk the tiniest storytelling tool? 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?