Dan Hockenmaier

A 'smiling' retention curve, where engagement increases over time, is the strongest indicator of product-market fit and a signal to scale.

"Even if you have a very few customers, if your cohorts look really good, they're retaining or even kind of like the classic smiling curve where you see more in engagement later in the life cycle than..."

Growth loops, such as virality or reinvesting margin into paid acquisition, are more accurately measured by payback period than LTV/CAC because speed of reinvestment drives compounding growth.

"The most basic example of this would be virality. Your existing customers are referring new customers and those go on to refer new customers. Based on that coefficient, it has a lot to do with how fas..."

Marketplace pricing is a balancing act where higher commissions fund demand-side benefits but risk discouraging supply.

"If you take a marketplace, typically you're charging commission on the supply side and their sensitivity to that commission is much harder to understand... The more you charge, the more you can fund b..."

Marketplaces can justify higher commissions by moving deeper into the value chain and taking on more operational responsibility (e.g., logistics, trust, or risk).

"Broadly the evolution looks like kind of Marketplace 1.0, which is all they're doing is aggregating demand... Then you have a managed marketplace like Airbnb or Etsy, which did something really fundam..."

The guest identifies liquidity as the 'number one metric' for marketplaces and provides specific tactical advice on defining and reaching it.

"The definition I would give is how reliable is the marketplace? If the consumer is looking for something or supplier is looking to sell something, how often can they do that thing that they're trying..."

The guest emphasizes that the biggest lever for retention is 'inflecting the early user experience,' which is a specific product discipline distinct from general retention or HR onboarding.

"Very often I think the biggest wins in retention come from inflecting the early user experience."

Certain teams must build models to manage inherent tensions (e.g., quality vs. quantity) rather than simple linear funnels.

"But then you have all these teams that are really managing some tension in the business, which is totally different than a funnel. So say if you have a marketplace quality team... if I let on a bunch..."

A growth model provides a 'common currency' to compare the impact of disparate projects across different teams during planning.

"The most difficult thing about making that kind of effort is developing a common currency by which you can trade off their efforts. So this team is saying they can move this metric by X and this team..."

When expanding, prioritize market adjacency and the ability to execute over the theoretical size of the Total Addressable Market (TAM).

"TAM or the size of the market actually matters very little because these are all big enough that they would dramatically inflect the curve of the business if you make them work. It's much more relevan..."

Horizontal marketplaces often beat vertical competitors because their higher customer LTV (from cross-selling) allows them to outspend on acquisition.

"At Thumbtack example, we had a spreadsheet which tracked hundreds of verticalized competitors where somebody would try to pick off the electricians category, the wedding category, the lessons category..."