Ecomm Cowboy

This week, we’re breaking down the moments where commerce, culture, and attention collide — from space-bound brand stunts to livestreams redefining entertainment, and the marketing plays actually winning right now.

We kick things off with Netflix’s latest livestream push and what it signals about the future of content, community, and conversion. Then we head to space with Nutella’s viral moment and unpack why the best brands today are engineering attention—not just running ads.

We also dive into why H‑E‑B continues to dominate social with a hyper-local, culture-first strategy, plus the rise of NASA-inspired products and what it says about where branding is heading next.

Plus, we’re joined by top operators building in real time:

Rob Freund (Founder, Robert Freund Law)

We break down what every ecommerce brand needs to know about FTC compliance, influencer marketing, and legal risks, including:

- The biggest compliance mistakes brands are making right now

- How AI-generated recommendations change disclosure rules

- The legal landmines in subscriptions, UGC, and pricing strategies

Jai Dolwani (Founder & CEO, The Starters)

From scaling Winc to building a 600+ freelancer network, Jai shares:

- Why the old hiring playbook is broken

- What brands actually need from talent in the AI era

- How to structure a fractional team at $1–5M revenue

- The biggest hiring mistakes founders make

Ben Hindman (3x Founder | ex-Shopify PM)

We go deep on building modern consumer brands:- What he’s launching next with Le Lick

- Lessons from scaling and exiting Splash

- What most merchants don’t realize about Shopify

Internet & Culture Segment:

- Viral brand moments and campaigns that actually hit

- The best (and worst) merch drops of the week

- Creator economy shifts you need to be paying attention to

If you’re a founder, operator, or growth leader, this livestream will give you a real-time look at what’s working right now—and where ecommerce is heading next.

— — —

Welcome to DTC's daily — what's now and next in ecommerce so founders, marketers, and operators can survive and thrive.

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Today’s livestream breaks down the biggest shifts happening across ecommerce, marketing, and digital media plus live conversations with operators building in real time.

We start with a major platform update: Shopify just rolled out B2B features to every merchant, signaling a massive shift in how brands think about growth, retention, and wholesale. From there, we dive into the latest trends shaping the industry from affiliate-driven scale and retail expansion to the growing backlash against AI infrastructure and what it means for the future of tech.

We’re also joined by top founders, operators, and investors for deep-dive interviews you won’t hear anywhere else.

In this episode:

- Shopify rolls out B2B tools to all merchants (and why it matters now)

- The rise of affiliate-driven brands and breakout retail moments

- LinkedIn’s potential move into newsletters + media consolidation

- Why people are pushing back on AI data centers

- New Reddit strategies for organic growth and demand capture

- Cultural commerce moments (Masters merch, celebrity product spikes)

Live Interviews:

- Justin Silver (Symptoguard, eCommerce Fight for Charity)

From building and exiting a beauty brand to organizing one of the most unique ecommerce events ever—executives stepping into a boxing ring for charity.

- Jimmy Kim (Sendlane, Commerce Roundtable) & Taylor Holiday (Common Thread Collective)

Breaking down the future of ecommerce events, community, retention marketing, and what it actually takes to scale profitably in 2026.

Plus:

- SMS, email, and creator marketing strategies that are working right now

- How top brands are scaling content and creative production

The biggest stories from LinkedIn, X, and the operator ecosystem this week

— — —

Welcome to DTC's daily — what's now and next in ecommerce so founders, marketers, and operators can survive and thrive.

Weekly newsletter:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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We’re covering everything from the latest shifts in hiring and ecommerce strategy to Amazon’s rising costs, the growth of resale, and the creative campaigns that actually captured attention this week. Plus, we’re joined by two founders building and scaling in real time.

In this episode:

Hot Jobs of the Week

We break down the most interesting roles in ecommerce right now — from creator-led brand building at BK Beauty to senior ecommerce leadership at Huckberry and Amika, and what these roles signal about where the industry is heading.

News & Trends

- Amazon introduces a new 3.5% fulfillment surcharge

— what it means for your margins

- Resale continues to take share from traditional retail

- The best April Fools brand campaigns and why they worked

Marketing Deep Dives

We discuss SMS strategy with Postscript and how brands can turn it into a top revenue channel, plus how Insense is helping brands scale creator-driven content and UGC.

Internet & Culture Segment

We react to the latest viral moments, brand activations, and “unhinged” marketing plays that are winning attention right now.

Guest Interview: PrettyBoy Skincare (Ben Feys & Kevin Niehoff)

The founders of PrettyBoy share how they built a million-dollar men’s skincare brand from scratch:

- Betting $70K of their own money on their first production run

- Scaling from $187K to $1.1M in one year

- Building a subscription engine that drives 60% of revenue

- Why they’ve stayed anti-discount in a promo-heavy market

- The power of founder-led content

Optional Deep Dives (time permitting):

- TikTok Shop + review syndication and what it means for conversion

- Amazon testing Prime shipping on external websites

— — —

Welcome to DTC's daily — what's now and next in ecommerce so founders, marketers, and operators can survive and thrive.

Weekly newsletter:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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Today’s episode breaks down one of the biggest shifts happening in ecommerce right now: what happens when AI, creative, and distribution collide.

We start with the story of Medvi, a $1B “one-man” AI-powered telehealth brand that’s forcing operators to rethink what a company even looks like. Is this the future of lean ecommerce, or is there more beneath the surface?

From there, we unpack what’s really happening inside Commerce Roundtable Austin — who’s in the room, why the $5M–$50M brand segment dominates, and what it says about where the industry is heading next.

We’re joined by three operators with deep experience across DTC, paid media, and creative:

Hal Smith (Founder, H Street Digital) brings lessons from political advertising into ecommerce, breaking down why most brands misunderstand their own data, how attribution is misleading teams, and what it actually takes to acquire net-new customers profitably.

Brett Curry (CEO & Co-Founder, OMG Commerce) draws on 16 years of agency experience and tens of millions in ad spend to explain why YouTube remains one of the most underutilized growth channels, what makes it work today, and how AI will reshape agencies going forward.

We also cover:

- The rise of AI as an “employee” inside ecommerce teams

- Why bold product positioning is outperforming safe branding

- The gap between platform-reported performance and real CAC

- What it takes to scale creative in a post-targeting world

Plus, rapid breakdowns of emerging products, trends, and viral moments shaping the next wave of ecommerce.

If you’re a founder, operator, or growth leader, this episode is designed to give you a clearer view of what’s actually working right now — and what’s coming next.

— — —

Welcome to DTC's daily — what's now and next in ecommerce so founders, marketers, and operators can survive and thrive.

Weekly newsletter:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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Today’s episode is packed. We’re breaking down one of the most shocking DTC outcomes in recent memory how Allbirds went from a $4B darling to a $39M exit and what every operator should learn from it.

Then we sit down with Caleb Sloop to unpack the truth about coffee in America, why “mold-free” is becoming a real category, and what it takes to build a premium CPG brand in a crowded market.

We also dive into the macro pressures hitting ecommerce right now from rising fuel prices to shifting consumer confidence and what that means for your conversion rates, pricing strategy, and demand.

On the tech side, we’re covering Amazon’s leaked Rufus AI deck and what it signals about the future of shopping, plus Google’s AI-powered inbox rollout and how it could reshape email marketing as we know it.

We’ll also break down standout marketing plays from Liquid Death giving away a house to Ghost Energy’s expansion into cocktail-inspired flavors and what they reveal about where brand building is headed.

To close it out, Andrew Haykal joins the show to talk cold outreach, lead generation in 2026, and why the people saying it’s dead are missing the bigger picture.

If you’re building, scaling, or investing in brands this one is for you.

— — —

Welcome to DTC's daily — what's now and next in ecommerce so founders, marketers, and operators can survive and thrive.

Weekly newsletter:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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Today’s Friday Feel livestream covers the biggest stories shaping ecommerce, marketing, and digital media right now—plus deep-dive conversations with operators actually building in the space.

We start with one of the most talked-about brand stories of the week: Comfrt being sued by Realtree, and what it reveals about intellectual property, “copy vs inspiration,” and the real challenge of building a defensible brand in 2026.

From there, we’re joined by Chris Geiss to break down the hidden infrastructure behind high-performing Shopify brands. We get into Bulk Discount Bot, why personalized discount codes outperform, what “risky” discounting actually means, and what 117 million codes reveal about how brands are leaking revenue without realizing it.

Next, Brandon Maskell (Reef) joins the show to talk CRO at scale—how to approach testing, where most brands go wrong, and how to balance quick wins with high-impact experimentation across a growing business.

On the platform side, we cover Spotify’s move into carousel shopping ads, Amazon’s leaked Rufus AI pitch and what it means for the future of search and discovery, and how conversational commerce could reshape how products are found and purchased.

We also sit down with Adil Mania, the creator behind Silicon Mania, to talk about the future of media, AI-generated storytelling, and why tech content needs to become entertainment-first to survive.

Rounding out the show, we hit a series of fast-moving stories and trends:

- The voluntary dismissal of the David Protein lawsuit

- Whoop raising $575M at a $10B valuation

- The rise of AI-generated music and custom jingles

- And a look at some of the most unexpected product launches and brand collaborations making waves right now

If you’re a founder, operator, or marketer, this episode is a real-time look at what’s working, what’s changing, and where things are headed next.

— — —

Welcome to DTC's daily — what's now and next in ecommerce so founders, marketers, and operators can survive and thrive.

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The future of marketing, ecommerce, and content is shifting fast—and this episode is a full breakdown of what’s actually happening right now.

We’re covering everything from the rise of AI-generated content and automated creator marketing to new ad platforms, platform risk, and why brands can’t rely on the same playbook anymore. If you’re an operator, founder, or marketer trying to stay ahead, this is your pulse check.

We also sit down with some of the sharpest minds in the space—people actively building, scaling, and navigating these changes in real time.

WHAT WE’RE COVERING

- The rise of “petty lawsuits” and what it says about attention, culture, and modern business

- Why “Millennial marketing” is dying—and what’s replacing it

- The risks of automating authenticity with AI-generated content

- Why brands must diversify beyond Meta (and where to look next)

- AppLovin’s breakout moment and what makes it different from traditional platforms

- Reddit launching shopping + DPA ads—opportunity or risk?

- Platform risk in ecommerce (and how it can kill businesses overnight)

- The reality of paid media then vs now (from 800% ROI to today’s landscape)

- Why distribution and audience ownership matter more than ever

- Amazon, TikTok, and the evolution of content + commerce

- Emerging trends like AI-native products, micro-drama content, and new hardware concepts

FEATURED GUESTS

Trevor Crump (Bestie Media, Bestie AI)

- Why safe, “on-brand” marketing no longer works- The shift toward personality-driven, high-risk content- Why MER and customer data matter more than ROAS

Miranda Pettinger (Glamnetic)

- Scaling across Meta, Google, AppLovin, and more- Going from $0 to $80K/day on AppLovin in 7 days- What winning creative looks like across platforms

— — —

Welcome to DTC's daily — what's now and next in ecommerce so founders, marketers, and operators can survive and thrive.

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Today’s episode breaks down the biggest shifts happening across ecommerce, AI, and consumer brands right now—and what they actually mean for operators.

We start with a look at the latest “Hot Jobs” across DTC, unpacking what top brands are hiring for and why roles in growth, retention, and digital experience are evolving into full-funnel ownership.

From there, we dive into Meta’s latest AI developments and what TRIBE V2 signals about the future of advertising. As automation accelerates, we discuss whether media buying is being replaced—and why creative strategy may become the last true edge.

Next, we analyze Pop Mart’s explosive growth and why its 91% member-driven revenue and 51% repeat purchase rate may represent the most important case study in modern commerce. This isn’t just retail—it’s a loyalty engine.

We also break down a viral “reindustrialization” moment and ask whether these narratives are authentic shifts or engineered for attention, followed by a real-time look at the realities of building in public and how founders navigate pressure when things aren’t going to plan.

On the distribution side, we cover Brez entering Target and what it actually means for DTC brands moving into retail—where the tradeoffs are, and what changes operationally.

We then get into personalization, sparked by a Klaviyo misfire, and explore why most brands still get it wrong despite having more data than ever.

We also discuss the rise of brand collaborations as a growth lever and whether partnerships are becoming a more effective channel than paid media.

The episode features two in-depth interviews:

Dr. Anthony Gustin, founder of Lineage and Equip Foods, joins to discuss the future of health, building multiple brands in the same category, and what separates lasting companies in the wellness space.

Ritwik Pavan, Chief Business Officer at Fragile and creator of Hardware Nation, shares why hardware may be the next major frontier, how AI is enabling a shift toward physical products, and what it takes to build recurring revenue in traditionally one-time purchase categories.

If you’re building, scaling, or investing in consumer brands, this episode is a deep dive into where the market is going next—and how to position for it.

— — —

Welcome to DTC's daily — what's now and next in ecommerce so founders, marketers, and operators can survive and thrive.

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Today’s episode covers one of the biggest shifts happening in ecommerce right now: the move toward AI-powered, agent-driven shopping experiences—and why Shopify may be positioning itself at the center of it all.

We break down what “agentic commerce” actually means for brands, how it could change customer acquisition forever, and whether storefronts as we know them are becoming obsolete.

We also dive into a major legal development that could reshape the future of social media. A recent verdict against Meta and YouTube may signal a new era of accountability for platform design, addiction mechanics, and user harm—with thousands of similar cases waiting in the wings.

On the commerce side, TikTok Shop continues to evolve rapidly, now testing new ways to share return costs with sellers. We discuss what this means for margins, platform trust, and whether TikTok is becoming a true competitor to Amazon.

From there, we explore one of the most overlooked macro trends in retail: the rise of GLP-1 weight loss drugs and how they’re already reshaping apparel demand, sizing trends, and consumer identity. This isn’t just a health trend—it’s a structural shift with real implications for brands.

We also highlight standout marketing moments and product drops, including a Made-in-USA golf brand and KFC’s unexpected move into wearable merch, and what they reveal about modern brand building.

The episode features two in-depth conversations:

Connor Gross on why hiring is broken, how AI is changing what companies look for, and why most brands should rethink when and how they hire.

John Mark Pero of Levers Health on building a telehealth company in a highly regulated space, competing in the GLP-1 boom, and why combining clinical infrastructure with ecommerce may be the ultimate moat.

We close with rapid-fire insights on lifecycle marketing strategy, the rise of AI-generated creators, and why top brands are aggressively investing in creative strategy as the new growth lever.

If you’re building, operating, or investing in ecommerce, this episode will give you a clear view of where the market is heading—and what actually matters right now.

— — —

Welcome to DTC's daily — what's now and next in ecommerce so founders, marketers, and operators can survive and thrive.

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Today’s show is packed with major shifts across payments, AI, logistics, and growth strategy — plus deep-dive interviews with some of the sharpest operators in the game.

From Stripe enabling native checkout inside Facebook… to FedEx launching 2-hour delivery… to Meta quietly changing how ads actually work — this is the new playbook for 2026.

WHAT WE’RE COVERING

Stripe x Facebook Checkout

Stripe just partnered with Meta to enable native checkout directly inside Facebook ads. No landing pages. No friction. What this means for conversion rates, attribution, and the future of ecommerce.

Carter Kuo (Concho) Interview

From college startup to major licensing deals with brands like Miller Lite — how Carter built a culturally relevant hat brand and scaled it through distribution, creators, and identity.

Fil Pejic (Bedford) Interview

500M+ emails sent. 5M+ subscribers. Fil breaks down what brands STILL get wrong about retention — and how to actually maximize LTV in a rising CAC world.

Torii Rowe (Dream Labs) Interview

From cop to elite media buyer. Torii shares what Meta is really optimizing for now (hint: not ROAS), what’s coming in Q2, and how brands should adapt.

AI Shakeups: Sora + Disney x OpenAI

AI video is heating up — but major deals are falling apart. What’s actually happening behind the scenes?

FedEx Same-Day Delivery

FedEx just launched 2-hour delivery. Is this the first real alternative to Amazon logistics for DTC brands?

RAPID FIRE

- TikTok Shop continues to explode (BK Beauty hits #1 in LIVE GMV)

- Superpower x IM8 partnership

- Chewy hits record spend per customer

- Postscript making noise at Shoptalk

WHAT YOU’LL LEARN

- Why checkout is moving inside platforms

- The shift from ROAS → new customer acquisition

- How top brands are winning with retention, not just ads

- What faster delivery means for your margins

- Where AI actually fits (and where it doesn’t)

— — —

Welcome to DTC's daily — what's now and next in ecommerce so founders, marketers, and operators can survive and thrive.

Weekly newsletter:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://newsletter.ecommcowboy.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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