Flywheel Strategy

08/13/2026

We’re excited to announce that Flywheel Strategy Founder Kate MacCabe will be speaking at DTC LIve Connect in NYC on September 15.

Kate will join David Baker, Co-Founder and CEO of Second Story, for a panel titled “We Haven’t Spoken About AI Yet?! With Second Story & Flywheel Strategy.”

While nearly every brand has experimented with AI tools, far fewer have redesigned how their businesses operate around them. This conversation will explore what AI is actually changing across DTC organizations, from team structure and operating speed to quality and revenue, as well as where the technology still falls short.

Kate will share what Flywheel is seeing among brands generating meaningful results, what an AI-ready team looks like and how smaller teams can begin adopting AI without a significant budget.

The brands positioned to win won’t necessarily be the ones with the most tools. They’ll be the ones that rethink how the work gets done.

Register your interest: https://2aahovc9gzu.typeform.com/to/X5l5DJZZ?utm_source=facebook_flywheelstrategy

07/03/2026

🌊 Feeling overwhelmed by the AI wave?

With new AI tools launching every week, the real challenge isn't trying them all—it's knowing which ones actually move your business forward.

AI is an incredible tool, but it shouldn't be steering your strategy.

Read Caroline Reekie's latest thoughts on making AI work for your marketing without handing over the wheel. 👇

https://flywheelstrategy.co/overwhelmed-by-the-ai-wave/

06/04/2026

We went to NY Tech Week with a question: what do founders and investors actually think about the AI market — not what they say at panels, but what they really think?

We ran an anonymous survey. We facilitated a room where people could say the honest version. And the data was telling.

A few highlights:
📊 Q1 2026 venture records collapse by 73% when you strip out the 5 biggest deals. The boom is concentrated at the very top.
📊 75% of AI founders say it's harder to raise right now, despite being in the hottest sector in venture.
📊 90% of AI founders identified a gap between their product's actual capabilities and what the market assumes about them.
📊 ~25% of respondents say they communicate more AI optimism in public than they actually feel.

We wrote it all up with the full data and the implications for AI startup market fit, messaging strategy, and fundraising.

Read the full recap here -> https://flywheelstrategy.co/ai-hype-fundraising-nyc-tech-week-2026/

Key insights from TRUE CONFESSIONS: AI Hype + Fundraising, hosted by Flywheel Strategy and Tech/ish during NYC Tech Week.

05/15/2026

Most marketing teams aren’t underperforming.

They’re just operating without enough clarity.

When everything feels urgent, workflows get heavy and creative energy gets drained. The fix usually isn’t more tools or headcount — it’s operational focus.

Clarity creates momentum.
Clarity protects creative work.
Clarity is a strategy.

Read more to learn how clarity can be your strategic lever ->

https://flywheelstrategy.co/strategic-clarity-marketing-creative-operations/

05/02/2026

Join us next Thursday, May 7th at 2 pm ET, for "Ask Flywheel Anything: From Ecommerce Playbooks to Reality", a small-group strategy session for ecommerce founders and leaders.

This session is led by Gaïana Joseph, Digital & Ecommerce Strategist at Flywheel Strategy and founder of Papa Luc’s Provisions.

We’ll talk through what actually works when applying ecommerce best practices, where founders often get stuck, and how to make smarter decisions across site, retention, and growth.

Limited to 10 people.

RSVP:

Ask Flywheel Anything is a high-touch, open mic + strategy session for ecommerce leaders where you can get direct guidance on everything from business…

04/27/2026

Most marketing doesn’t fail because of budget.
It fails because the idea isn’t clear enough.

The best campaigns of 2026 so far prove it:
– Solve a real problem
– Lead with a human moment
– Say one thing, well

That’s what actually gets people to stop, pay attention, and share.

A few standout examples (and what to take from them) -> https://flywheelstrategy.co/2026-brand-campaigns-stop-stare-share/

Stella Artois JACQUEMUS Squarespace Heinz

03/02/2026

is transforming e-commerce, but the leaders who win will be the ones who make smarter bets.

✨ Smarter Bets
The AI Tradeoffs E-Commerce Leaders Can’t Afford to Ignore
🗓 March 9 | 6:00 PM
📍 Mejuri Flatiron, New York

As personalization becomes more sophisticated, so do the tradeoffs. Relevance versus privacy. Automation versus human touch. Growth versus long-term brand trust.

Join us for an evening discussion with e-commerce leaders, AI practitioners, and founders who are navigating these decisions in real time.

We will cover consumer expectations around data, the role of transparency in AI-driven experiences, and practical strategies for building personalization that strengthens rather than erodes trust.

Networking to follow, plus 15% off at Mejuri for attendees.

RSVP now → https://luma.com/f4ab92bs

01/30/2026

📣 Calling all founders, innovators, and e-commerce builders!

We’re thrilled to share that our founder, Kate MacCabe is serving as a judge for the Arcangel $100,000 E-Commerce Pitch Competition in just a few weeks in .

Side by side with SHOPLINE, Jonathan Hung, 🚀 Andy Karuza, Christopher Gravagna, and Aiden Rubinstein, the competition on January 31st will be a high-impact event spotlighting early-stage physical product brands and startups.

Kate will be joining the panel to evaluate pitches, offer strategic insight, and champion bold founders driving growth in consumer, wellness, apparel, food & beverage, and lifestyle categories.

👉 Whether you’re looking to pitch or just soak up the energy, this is a can’t-miss opportunity to connect with peers, investors, and brand builders shaping the future of commerce.

🔗 Register to participate -> https://luma.com/hd1zo32y?tk=6gxLU7

11/28/2025

It’s that time of year — is on, and Flywheel Strategy is taking you backstage.

Head over to our Instagram page through Monday to catch our realtime stories: we’re sharing best-in-class Black Friday & Cyber Monday campaign highlights, holiday marketing tips, and real-time inspo.

Whether you’re a brand, an agency, or just here for marketing inspo — this is a roundup you don’t want to miss. 👉 https://www.instagram.com/flywheelstrategy/

11/26/2025

Black Friday + Cyber Monday week is here — sending all the good luck, strong coffee, and smooth launches to every DTC team. ☕🔥

If you’re leading marketing or creative operations right now, we put together a guide to help you manage the madness: https://flywheelstrategy.co/holiday-rush-creative-and-marketing-teams/

From shared calendars to tightened approvals to organizing your BFCM asset hub, this guide walks through exactly how to keep teams calm, coordinated, and ready to execute.

You’ve got this — let’s make this the best year yet. 💛🛍️