000023 - Evaluating Media Models

It’s been several weeks since sending anything out. Hope everyone is doing well. I won’t talk about the virus or markets here, so hopefully it’ll get your mind off it for a hot minute.

I’ve been chatting with a lot of people in the content space lately. Entrepreneurs and investors and writers - people you would know if you share my Twitterverse. I have a lot of momentum with writing and I think I can start a business. A few questions I’m considering:

  • Is the future of media personality-driven or brand-driven?

  • Is it more powerful to be niche, or to have a paid membership business model?

  • At what point can free content convert to paid? If you start with paid from the beginning, which content is free and which is paid?

  • Why are there so many more content-driven VC firms vs content-driven consulting firms?

  • Bottoms-up distribution is hot trend in B2B SaaS (Notion, Airtable, Slack, etc.). Does this exist in media too? Is there such thing as an “enterprise media” publication?

  • Should I cover a hot subject that has a lot of competition but is growing (DTC, crypto, consumer tech) or something I know about but isn’t as sexy (commercial services, vertical SaaS, institutional finance)? If it’s the latter, what is the correct voice? What’s the correct business model?

  • Do I personally want to work on a company that breaks news, or does research? What about consulting? Content marketing?

  • Can I get to ramen-profitability in time so that I don’t have to take another job?

I’m particularly interested in this space because I can start it with minimal capital, I have the requisite skillset, and it’s not subject to aggregation. Everything consumer-facing will be increasingly niche (this isn’t a novel opinion) and I’d love to spend the next several years building something great for a niche.

The more people I talk to in VC and VC-backed startups the more I think I don’t want to do that. As a founder, it dramatically reduces the amount of successful outcomes. As an employee, getting equity that’s third place in the capital stack without any debt is terrifying.

I’ve learned that compounding value really excites me. When I feel like what I’m doing today will be more valuable to me tomorrow, I’m highly motivated.

One entrepreneur I spoke with said his goal for his employees was to “make sure they go home feeling like they had a productive day”.

Another business writer I talked to pointed me to this provocative Tweet:

He put it this way: there’s two things that come from writing.

  1. The piece of content that’s published

  2. The accruing value from repeatedly publishing

Combining these two conversations is why I think I’m struggling with my current job and want to start my own thing.

I’ve never had so many days where I feel shitty about my work at 10pm and sulk to bed to avoid feeling guilty about my procrastination. And I think it’s because very little of #2 is going to me (I remember feeling excited most times I would post something when I was writing for myself).

Anyway. If you have some thoughts on media / content / marketing / B2B publications / free vs paid, hit me up. If my nerves about the free falling market don’t get the best of me, I’ll be starting something in May.

This is my public journal and these are rough ideas. Feel free to unsubscribe at any time.

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