Are we actually running in the right direction?

A conversation with Holden Page evaluating the viability of solopreneurship for the long haul.

You’re reading the Media Hackers tool teardown. Each post breaks down tech tools that newsrooms and media organizations. I’m Erin Mikail Staples, and I work at the intersection of community and product, with a work history in media organizations, tech startups, and SaaS platforms, and I’m passionate about empowering creators.


How the heck did we get here?

For many folks its second nature. Build your audience, know your audience, create a community of your audience that moves with you from platform to platform. The tech-bro world has done a very good job of this and determining what they need to do. However, for many journalists, this can be perceived as a time-consuming task that takes away from a core function of your role — reporting.

I recently chatted with Holden Page for this week’s issue, and while much of this newsletter has so far been the perks of being a solopreneur, this time around, we’re going to explore if this is even a viable business model or, a byproduct of hustle culturethat has us monetizing every last hobby.

Holden has had a career much like my own, jumping back and forth, in and out of more media-related roles. Before his current role as Research Operations Manager at Golden, he was at Crunchbase working as its managing editor, helping drive their editorial content. During this time, he spent a good chunk of time convincing journalists that their email lists were worth building.

“Building up an audience, and sustaining an email can be awful, but it also provides you so much value as a journalist”

And these skills aren’t solely just for journalists, you’ll find that many of these skills, of building an audience are used by many careers that are fairly new.

The difficulty of going solo

The dream of being an independent content creator comes with certain freedoms, from editorial decisions to even hours of your day.

It’s felt like, in the last 18 months, we’ve seen more newsletters than ever. It’s a story that’s been told, of hope and optimism in the New York Times, Marie Claire, and a particular favorite article of mine that questioned the trend in the Atlantic. It’s been a topic that’s been so romanticized that we don’t talk about how freaking hard it is to do right.

Talking with Holden, we expressed this sort of rose-tinted glasses that happens with newsletters and newsletter discoveries, and developed a list of some of the problems problems that independent content creators will face:

  1. Multiple Skillsets: By being a solopreneur, you have to be your own business operations, marketer, product manager, writer, editor, and designer — it’s a large hill to overcome, you’re not just writing every day anymore.

  2. Balance: How will you balance the business operations with writing? Where’s the break and fine lines? Also when you are your job and livelihood, when do you log off.

  3. Financing: Journalism is expensive, and many people don’t realize that. Often, to do a story well, you’re spending months and months and months on the same topic — something that can be hard to finance.

  4. Lonesome: No newsroom peer editing, watercooler conversation, or folks to bounce ideas off of on the regular. I’ve seen a few different groups that have decided to bounce ideas off of one another, but its more of the exception than the norm.

  5. Salaries: For, what I personally believe, has been one of the largest issues with journalism and journalism schooling, the business side of news has been divorced from the job of reporting, which, leaves many journalists in a world of their own when they make the transition to be independent.

That doesn’t mean its all for nothing. There’s a few ‘hacks’ that have been used to kickstart your soloprenurship journey. Aside from a clear set advantage of those who are starting with a large existing audience, there’s a sort of validity that comes from writers that once worked at the New York Times that went on to build their own thing.

“Obviously, when you’re at the New York Times, it’s much easier to build your audience — the mass media sort of subsidized the cost of audience growth. And this is a two-fold game, a journalist with a large audience is also more valuable to a newsroom”

A shift in thinking

The one thing that we can all agree on is crystal clear after the rise of the solopreneur, is that we’ve begin to fully recognize the power of owning your audience. The business side of things aren’t just some fluffy shit that happens behind the scenes, it’s something that will keep us up and running for the long haul!

Holden’s takeaways

Some parting thoughts and tips for anyone looking to create their own thing

  • Be prepared for the resilience to do this day in and day out. “I want to build a business and make this sustainable,” and “I want to do what I love doing” can be at odds with one another, and that will be a hurdle to overcome.

  • Find your own mission away from everyone else's mission, you're here to build your own business and legacy, and think about it that way and what drives you.

  • Be willing and very very prepared to become a really great writer really fast because you don't have a lot of time to spend on the art of writing. You need to spend a lot of your time on the art of running a business and running the technical aspects of it yourself.

  • Pick your tech stack in relation to what you need today — Substack is a great place to get started and easy to get started and set up, you're going to want to grow eventually and Substack doesn't provide you that. you want more customized tiers and new payment providers, what does this look like as a website, and what is a Mailchimp/membership site, and some people over-index that. figure out your MVP is and what you want to own next. Any startup will use its platform at the end of the day to incentivize growth, how does this impact you?

  • Solo content creation is a lonely task and it is hard to do it successfully when business demands must be acknowledged in tandem. Find yourself a mentor, and find someone that you can speak honestly with — which means you should talk to someone who understands what you're trying to accomplish through your business goals. You’ll also have to balance how to keep your journalistic independence with growing your business.



In this weeks toolkit:

Each week, outside of the deep dive, I’ll be sending out a toolkit with some of Holden’s tips to building an audience, as well as leveraging your current strengths to start towards the path of being a solopreneur. As an added bonus, we’ll chat about what newsletters he’s digging right now.

Is there a topic that you’d like to see me breakdown? Shoot me an email!


Media Hackers is a project built by Erin Mikail Staples focused on how we can use tech tools to create better media businesses.

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