Every new level of entrepreneurship creates a new trench. The Trenches documents what struggle produces, not what it looks like from a stage.

First Episode: Parker Cox (releasing soon)

In mid-2022, he was running one of the 10 fastest organically growing property management companies in the country.

From the outside it was a success story. From the inside he was redlining to stay there, and paying for it in ways he doesn't dress up on the record.

Three years later, he runs 3 companies and won't take a required trip again.

In Episode 001 with Parker, the 3 questions that ended the old business, the offshore hire that cut CAC 40% in 90 days, exactly who to hire at $1M, $3M, and $8M, and the 2 rules he won't break now. Subscribe below to be the first to know when Parker’s episode, and future episodes, go live.

There's a question worth asking about every channel you're using: does this get better the longer I do it?

For most marketing, the answer is no. Paid ads don't get cheaper with experience. Cold outreach doesn't get warmer over time. The channel performs about the same in year three as it did in month one.

A personal brand is the exception.

The work you published last year is still producing this year. A newsletter or blog article from 18 months ago can still be read, still be found, still sending people to your profile. A newsletter subscriber from last spring can still open every week. A client who found you through your content and referred two more did it without costing you anything.

Four things change over time that don't change in a paid channel:

Paid channels produce a flat line. This produces a curve.

Look at your business and answer 3 questions honestly:

Most founders find that everything on their list is flat. It works, but it doesn't compound over time.

The point isn't to stop running paid channels. They fund the business today, and that matters.

The point is to make sure something underneath them is compounding.

Pick one channel that gets better the longer you run it and protect time for it every week. A newsletter. A weekly long-form post. A video series in one specific lane.

2 hours a week is 100 hours a year. That's a body of work, an audience, and a reputation that will still be producing in 2029.

5 spots up heading into September, reply “interested”

Not all engagement is weighted equally, and the signal that carries the most weight is often the one founders pay the least attention to: the save (or bookmark).

A save is the strongest vote a reader can cast. A like takes a reflex, but a save takes a decision that your content is worth coming back to.

Platforms read that as a sign your post has lasting value, and reward it accordingly.

This week, publish one post built specifically to be saved.

A checklist someone would run through later.

A framework they will want to reference.

A short, reusable process they cannot hold in their head after one read.

Make it genuinely useful to return to, then invite people to save it for when they need it.

Track saves on that post against your recent posts over the same window, alongside reach and replies.

The hypothesis is that reference value earns saves, and saves earn distribution. A post people want to keep will outperform a post people merely agreed with.

One post.

One thing worth saving.

A direct read on whether you are making content people consume or content people keep.

The AI answer engine Perplexity confirmed it has stepped back from advertising, concluding that ads sit in tension with the trust its product depends on. Even clearly labeled sponsorships give users a reason to wonder whether an answer is shaped by who paid rather than what is true, and for a product whose entire value is a trustworthy answer, that doubt is too expensive.

The decision is a useful signal for founders about where credibility is heading in an AI-mediated world. As more discovery runs through answer engines, the pressure lands on the trustworthiness of the source being cited rather than on who bought placement.

Earned authority becomes the thing that carries you into the answer.

The takeaway is that showing up in AI search will keep rewarding the same thing Perplexity is protecting: content credible enough to be cited on its merits, from a source a system will trust without being paid to.

Read more here

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