It’s been a little over four years since I made a go at turning this newsletter into a full-time gig, and from the very beginning I assumed that I’d be publishing regular dispatches about my progress. After all, the entire focus of this project is to make media entrepreneurs better at their jobs, and what better way to do that than to share the insights from my own journey?
That's the best story I've ever read about what happens to a journalist who spend four years working, working, working as a one-person company and using Substack as one of their delivery strategies. It's immediately useful and humbling for journalists like me who have similar paths, history, and large lists of people who have met us in person. And I wonder about all of the things you have thought through and put into pages and pages of writing--for yourself and on Google, in your search for some diamonds in that large pile of dirt we call a lifetime of professional experience.
Selfishly, I enjoyed your Office Hours simply for being in the 'same room' as others I find innovative and thought-provoking. Sometimes "access" on its own goes a long way.
😎
Looking forward to many more years of your success!
Thank you for the deep and honest inventory of your newsletter's story - especially your courageious admission that you write about media businesses but aren't running your own effectively.
As a committed reader of your great newsletter, I've also noticed that the paid offering hasn't been so focused and compelling. But your pitch today almost sold me! I'm seriously considering buying a paid subscription.
Fully agree with George Patrick. I would like to add two suggestions. 1. I didn’t realise until reading the newsletter that there is a difference between the paid and the non-paid podcasts, so maybe repeat that to us often. 2. I think at one stage you were offering a short, paid-for consultancy. I realise you probably don’t want to spend weeks on end doing long-term projects but super short ones can be good if they accumulate. For example, I have been able to charge big companies €600 for a one-hour consultation (that takes me a day to prepare). In my extreme niche area of Cyprus these requests don’t come round every often, but you are in a bigger space so am thinking it could be a good side-gig.
This story comes at a great time. I'm currently figuring out how to monetize my newsletter. Ads are very common for satire news because news locked behind a paywall hurts growth. Didn't realize the ad market slowed down.
How do you begin to court advertisers? I don't know if I'll do this process but it would be interesting to know.
This is a brilliant theory. I think many of us struggle with getting the mix of free and paid right and offering something that encourages people to subscribe. Thanks for sharing your story.
Nice article! I have learned that personal connection and fostering them with your audience whether it is a phone call, or a personalized conversation can have way bigger effects than people realize, but people don't want to build the ground work. You can't short cut building a loyal audience, great article simon!
Excellent analysis. Congrats on your sharing this and growing your base. I think it is a good problem to have. It is the growth v. revenue v. profitability puzzle. Any 'time' based offer is not scalable as you realized so the 30 minute intro phone calls would have hit a ceiling sooner than later. Did you consider charging additional for an interactive Zoom call which would limit the audience or offer it only to founding members? Or livestreaming on YouTube so the Q&A is mostly chat, and those who can will join the time that you host it v. coordinating it. Lots of ways to slice and dice this! Bottomline - pivoting is ok as a strategy. Good luck!
It is heartwarming how much you have learned and pivoted and experimented and tinkered through these years. You certainly do have a lot of benefits for paid subscribers or I can see how the churn reduction would be reduced.
It's not easy for newsletter operators to create a flywheel of diversified monetization. I think at the end of the day that still has to be our goal to become sustainable.
To be reliant on simply a b2c or B2B approached does not make much sense given how much they both tend to fluctuate. And God knows we know how much they fluctuate.
I think what you have found is also the relationships make the job more sustainable emotionally in spite of the financial insecurity. I have experienced a similar thing working with dozens of guests contributors.
I do like it when you strike a confessional tone however, and while I don't always agree with your media insights you have been exceptionally faithful to this platform and it's special perks and capabilities. I think your impact has gone far beyond the size of your list or your sponsorship income and that's an important factor to internalize.
At the end of the day we don't just do this for the money obviously because if we were we would not be here any longer.
That's the best story I've ever read about what happens to a journalist who spend four years working, working, working as a one-person company and using Substack as one of their delivery strategies. It's immediately useful and humbling for journalists like me who have similar paths, history, and large lists of people who have met us in person. And I wonder about all of the things you have thought through and put into pages and pages of writing--for yourself and on Google, in your search for some diamonds in that large pile of dirt we call a lifetime of professional experience.
Superb piece of writing and insight, with disarming openness - and uplift at the close. Thank you
Terrific review and discussion of next steps!
Selfishly, I enjoyed your Office Hours simply for being in the 'same room' as others I find innovative and thought-provoking. Sometimes "access" on its own goes a long way.
😎
Looking forward to many more years of your success!
Thank you for the deep and honest inventory of your newsletter's story - especially your courageious admission that you write about media businesses but aren't running your own effectively.
As a committed reader of your great newsletter, I've also noticed that the paid offering hasn't been so focused and compelling. But your pitch today almost sold me! I'm seriously considering buying a paid subscription.
Great insights, Simon. These personal in-depth looks into how your business runs, good and bad, are very useful.
Thanks for sharing
Ray
When you are going through hell….keep going!!!
Fully agree with George Patrick. I would like to add two suggestions. 1. I didn’t realise until reading the newsletter that there is a difference between the paid and the non-paid podcasts, so maybe repeat that to us often. 2. I think at one stage you were offering a short, paid-for consultancy. I realise you probably don’t want to spend weeks on end doing long-term projects but super short ones can be good if they accumulate. For example, I have been able to charge big companies €600 for a one-hour consultation (that takes me a day to prepare). In my extreme niche area of Cyprus these requests don’t come round every often, but you are in a bigger space so am thinking it could be a good side-gig.
This story comes at a great time. I'm currently figuring out how to monetize my newsletter. Ads are very common for satire news because news locked behind a paywall hurts growth. Didn't realize the ad market slowed down.
How do you begin to court advertisers? I don't know if I'll do this process but it would be interesting to know.
Trial and error and finding unique value propositions while getting to know your audience better.
It sounds like you've made tremendous progress in this Simon. Did you get many bites on the Gumroad?
This is a brilliant theory. I think many of us struggle with getting the mix of free and paid right and offering something that encourages people to subscribe. Thanks for sharing your story.
Nice article! I have learned that personal connection and fostering them with your audience whether it is a phone call, or a personalized conversation can have way bigger effects than people realize, but people don't want to build the ground work. You can't short cut building a loyal audience, great article simon!
Great insights. I didn’t realize that I could also be much clearer about what paid offers a reader. Thank you
Keep up the good work! Thank you for your transparency about how your approach your business.
Nice write-up! Congrats 👏
Excellent analysis. Congrats on your sharing this and growing your base. I think it is a good problem to have. It is the growth v. revenue v. profitability puzzle. Any 'time' based offer is not scalable as you realized so the 30 minute intro phone calls would have hit a ceiling sooner than later. Did you consider charging additional for an interactive Zoom call which would limit the audience or offer it only to founding members? Or livestreaming on YouTube so the Q&A is mostly chat, and those who can will join the time that you host it v. coordinating it. Lots of ways to slice and dice this! Bottomline - pivoting is ok as a strategy. Good luck!
It is heartwarming how much you have learned and pivoted and experimented and tinkered through these years. You certainly do have a lot of benefits for paid subscribers or I can see how the churn reduction would be reduced.
It's not easy for newsletter operators to create a flywheel of diversified monetization. I think at the end of the day that still has to be our goal to become sustainable.
To be reliant on simply a b2c or B2B approached does not make much sense given how much they both tend to fluctuate. And God knows we know how much they fluctuate.
I think what you have found is also the relationships make the job more sustainable emotionally in spite of the financial insecurity. I have experienced a similar thing working with dozens of guests contributors.
I do like it when you strike a confessional tone however, and while I don't always agree with your media insights you have been exceptionally faithful to this platform and it's special perks and capabilities. I think your impact has gone far beyond the size of your list or your sponsorship income and that's an important factor to internalize.
At the end of the day we don't just do this for the money obviously because if we were we would not be here any longer.