Welcome to the latest edition of The Entrepreneur’s Tech Stack. I’m your host, Simon Owens. For those who don’t know me, I write a media industry newsletter you should definitely check out.

Today’s featured entrepreneur is Lindy Alexander. Lindy started The Freelancer’s Year in 2017 as a way of documenting her ‘journey’ of becoming a full time freelancer. She set herself a goal of hitting $100K in revenue in her first year of full time freelancing and blogged about it. Her monthly reports where she shared her income were especially popular.

Today, The Freelancer’s Year is a major business that offers self-paced courses for aspiring and established freelance writers. In the courses, she teaches how to get your articles published in magazines and newspapers; how to break into travel writing; and how to hit $100K from your writing by landing lucrative content clients. 

Lindy newsletter now has over 6,000 subscribers and she sells courses ranging in price from $9 to $2,000. “For me the marker of success is the success my students are having,” she told me. “Multiple students have hit their annual income goals (goals they never dreamed were possible) like hitting $100k from their freelance writing, or $80K in their first year of freelancing (part time!). I also have students who are regularly being published in fantastic publications (like The Guardian, Marie Claire, Nat Geo Traveler) and it’s always a thrill to know that I’ve played a tiny part in their success.”

Lindy walked us through the products that are absolutely essential to her business:

Hello Audio

My two main programs both have a private audio stream of all the content. This means that my students can listen to the lessons on their favourite podcast app if they don’t want to sit at their computer and ‘watch’ the content.

I adore Hello Audio ($468/year for the pro version) because you can have private and public feeds, you can drip out the content, and you can manage listeners with expiring feeds (so when their time is up in the program, they automatically lose access to the private feed). 

Not everyone who is enrolled in these courses taps into the private audio feed, but I can see from the stats that those who do really love it and listen again and again to the lessons. 


When I launched my first course in 2020 I hosted it on my WordPress site because I believed that it would be better to host it on a site that I owned. But, not being particularly tech savvy, this was a mistake, because when I changed one thing, it had a domino effect on lots of other moving parts. 

Later that year I found Kartra ($1788/year), an all-in-one course platform where I host my courses, build sales pages, create opt-in pages (that are displayed on my WordPress site), create surveys, host webinars, send emails, and more. 

It’s probably not as customisable as if I hosted on my site, used independent tools for each process like Lead Pages for my sales pages, Deadline Funnel for countdown timers, ConvertKit for emails, etc, but I want simplicity in my business and I’m not great at problem solving when tech things go wrong. So for now, Kartra is the best solution. 


I really love Skitch — a free tool for marking up, pixelating, or annotating images. I’m always taking screenshots of the wins my students are having or lovely emails I receive, so I drop these into Skitch, pixelate what I need to (if there are personal details the person doesn’t want shared), and it’s done. All my ‘social proof’ testimonials on my sales pages are done in Skitch. 


Voxer is another free app that I adore. It’s basically like a walkie-talkie where you can leave voice notes (up to 15 minutes) for other people. These can be 1:1 chats or group chats. I’ve received coaching via Voxer, given coaching via Voxer, and I have numerous chats each day with fellow business owners and entrepreneurs. 

I love that I can be out for a walk and chatting to an entrepreneur I know half-way across the world who is asleep but will wake up to a voice message from me. It’s super easy to use and I haven’t seen a need to upgrade to the paid version yet (which offers you a chance to recall messages). 

Unlike email, it means you immediately create a connection with someone through conversation and hearing their voice. And it doesn’t have any of the awkwardness that Zoom (or similar) does!


I’ve felt increasingly concerned about privacy in recent years so I made the switch from Yahoo and Gmail to Protonmail (7.19 €/month). It’s an encrypted email service based in Switzerland that uses audited end-to-end encryption and zero-access encryption for secure communication. This basically protects against data breaches, something which I think we all need to be mindful of.  

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Simon edits an industry newsletter that covers everything from the Creator Economy to traditional media. He also hosts The Business of Content, a podcast about how publishers create, distribute, and monetize digital content.

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