Before we move on to a new season, new guests, and some exciting new tips and tricks, let’s take a look back at everything we learned in season 1. Kristen runs through some of the standout moments from Playing for Keeps so far and how they set the stage for 2020’s year of retention.

It’s bite-sized, it’s sharp, and it’s loaded with some of the best advice you’ll get all year.

Throughout season 1 of Playing for Keeps, we've talked a lot about the importance of upholding brand standards across different channel of communication. This can be really tricky for growing DTC businesses already- imagine doing it across two different markets simultaneously. This has been a huge focus for the Ugly Drinks team as they expand from the UK into the US. In this episode, Hugh Thomas, Co-Founder of Ugly, explains how his team is divided between markets, and how they bridge the two to create a brand that can speak globally AND locally. Glocally, if you will.

Kristen goes deep with writer and DTC expert Kaleigh Moore, a veteran of the Churn Buster blog, not to mention Forbes, AdWeek, and more.

This week on PFK is a little different. With the recent explosion of brands entering the DTC space, Kris and Kaleigh look at some of the most exciting players and workshop ways that they could grow with a subscription model. From Outdoor Voices to Casper and Allbirds, this conversation digs into product discovery, working with an engaged community, and the future of the DTC space in 2020.

What does it mean to really understand your customers and craft your business around their wants and needs? That’s what retention is all about, right?

This week Kristen goes deep with Asher Hunt, co-founder and COO of Bite Toothpaste Bits, to talk about starting a business from passion, what authenticity really looks like in business, and how to grow and scale in the wake of a viral video. Plus, they get into the cadence of a delivery schedule and how a customer-focus can drive brand loyalty.

Brand loyalty is a coveted metric in the game of retention. But, what does brand loyalty actually mean? And how do modern DTC brands begin to build deeper connections with customers to encourage repeat purchases and extended LTVs? Kristen and Aaron Orendorff, founder of iConicontent and previously editor in chief at Shopify Plus, go on a super deep dive into this uber important, yet elusive metric. Tune in to hear Aaron's top tactics for actively driving customer loyalty through storytelling, brand aesthetics, loyalty programs, and content with examples from companies like Tracksmith and Pura Vida. Plus, learn who is the Most Handsome Man in Portland (hint: It's not a human).

Why is retention so hard for DTC brands to focus on, despite knowing how powerful it is? I've been pounding my head against the desk asking this question again and again. Data proves it's one of the biggest growth levers, CAC is too high to keep chasing, and yet, ecommerce brands still aren't shifting enough focus and effort to this side of the equation.

I couldn't figure it out, so I tapped the experts for this one. Hear from Web Smith, Reza Khadjavi, Jarid Lukin (KIND Snacks), Kaitlin Holliday (Four Sigmatic), Val Geisler, Jordan Gal, Aaron Orendorff, Taylor Holiday, Brandon Doyle, Matt Goldman, Ken Johnson (previously Manpacks) and more. Learn what's holding YOU back, and what you can do about it, b/c the brands brave enough to shift perspective will be the ones thriving in 3-5 years.

The world of wine is a $70 billion industry, with ship-to-home programs taking a bigger piece of the pie every day. While other brands are zeroing in on millennials, DRINKS is marketing to all wine enthusiasts, ages 21 - 91. Kristen sits down with Louis Amoroso, president of DTC for DRINKS to discuss how Wine Insiders uses deep personalization, feedback loops, and customer relations to be the powerhouse it is today. Plus, Kristen questions the impact Louis' childhood had on his business endeavor and explores the importance of retail experience in today's landscape.

Retention is the name of the game for subscribe and save programs, but measuring the impacts of your promotions on LTV isn't always an easy task. This week, Kristen chats with Jeff Schnepple, the Director of Marketing Technology at Ancient Nutrition, to learn how they conduct deep data analysis to uncover the offers that lead to the longest (and most profitable) LTVs (like free frothers).

Without looking, could you remember the brand and flavor of the toothpaste sitting on your counter? When's the last time you actually looked forward to brushing your teeth? These are the questions that brothers Cody and Julian Levine, alongside Lenny Kravitz set out to answer with Twice toothpaste. From beautiful packaging, to a completely new concept, and a deep charitable mission, Twice is making waves in the oral care industry. On this episode, Kristen sits down with Co-Founder and CEO, Julian Levine, to hear how the brand idea was born, what they've learned in their first year of business, what it's like working with Lenny Kravitz is, and what the future looks like for this inspiring brand.

Increasing MRR should be every eCommerce brand's focus. But, it’s a complicated machine of moving parts. As Wilson puts it, “anything that’s complicated can be simplified and broken down into its individual inputs”. Tune in as Wilson breaks down his model for increasing MRR at Kettle & Fire in a simple, strategic manner.