The Longer Game — retail reimagined
The DTC Playbook Everyone Copied Doesn't Work AnymorePhoto by Patrick McGregor on Unsplash

Cheap ads built a whole generation of online brands. Using that same plan today could sink a founder.

The DTC Playbook Everyone Copied Doesn't Work Anymore

Cheap ads built a whole generation of online brands. Using that same plan today could sink a founder.

Warby Parker, Casper and Away had the big exits every founder wanted to copy. Then, according to Jess Chan, many brands from that era fell apart.

Are you riding a trend, or building something that lasts? It helps to ask people who have seen both happen. That's what Cartology does every day.


Those big wins ran on cheap ads

Facebook was new and ads were cheap.

A brand could grow just because a subscription box felt exciting, no matter what was inside.

Back then, good timing mattered more than a good product.

Three captioned stills of Jess Chan and Rachyl Neidecker on The Longer Game talking about the early DTC era

The big numbers hid a money problem

The headlines showed huge company values.

Jess says that underneath, these brands were losing money on every new customer.

When ads got more expensive, that plan stopped working for everyone.


Their real skill was timing, and you can't copy timing

The founders who won back then showed up at exactly the right moment.

If you copy their moves now, you get the moves without the timing that made them work.

Copying a 2015 win in 2026 is like paddling out for a wave that already hit the shore.

"A lot of those brands would completely fail right now." — Jess Chan, Founder & Executive Chair, Longplay

What works in any market

The moves that last aren't tricks that fit one moment in time. They work no matter what the market looks like:

  1. A product that still makes money when ads get expensive.
  2. Customers who come back, so each one is worth more than it cost to win them.
  3. A real reason for your brand to exist, beyond being early to a new platform.

The Longer Game newsletter breaks down which old moves still work and which ones quietly drain a brand's money.


That wave is over

The wave that carried the last generation of brands is gone, and it isn't coming back the same way.

Captioned still from The Longer Game episode with Longplay

The founders who last will be the ones building for what comes next, not copying what worked before.

Listen to the full conversation with Jess Chan and Rachyl Neidecker on The Longer Game: https://youtu.be/XF-RErB_gYo

Listen to the episode

Know When To Get Off The Wave

Hear the full conversation on Apple Podcasts, Spotify, or YouTube.

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