This one is packed with giveaways.

🥳 Connor MacDonald shows you how to run a sweepstakes

💰 Stuart Chaney with “wallet passes” + a burning question

🗞️ Five biggest headlines from this week in consumer news

 BONUS #1  🎁

Have you grabbed your spot at the very first Operators Assemble Event? It’s June 17th. It’s online. It’s free.

It’s ridiculously stacked …

Best of all? HexClad, Ridge, and Simple Modern are giving away loads of prizes! From cookware sets and Damascus Steel knives to wallet “survival” kits and luggage to giftcards on giftcards.

​But you can’t win unless you sign up!​

Connor MacDonald Ridge, CMO

Your Guide to Running DTC Sweepstakes: 5 Questions

I’ve talked to so many brands recently about sweepstakes. We might see 10–20 in the back half of this year alone.

Having run Ridge’s summer sweepstakes four times, I wanted to share what we’ve learned on our way to last year’s …

• Biggest Q3 in company history
• 8-figures per mo. from July–Sept
• Double-digit growth each month
• Returning customers up 90% YoY
• 100% YoY lift in retention revenue
• Almost $10M in SMS sales alone
• Highest AOV & LTV in one quarter

Sweepstakes aren’t as simple as throwing together a prize — even a big one. I’ve seen a few brands try that low-touch approach, and I’ve got the sense they weren’t as commercially powerful as you might think.

Since Connor Rolain and I worked through both of our sweepstakes on last week’s podcast, let’s bring everything together into a single guide …

1. Goal: Why Should You Run a Sweepstakes?

For us, it started with a calendar problem.

We have our anniversary sale in Q1, Father’s Day in Q2 (which for us can be as big as the previous November), and the holidays in Q4. But August and September? We had nothing. No seasonal reason to buy a wallet.

Back in 2021, we decided to create something exciting for that period. Here’s how that initial version looked.

What I like about sweepstakes is that they’re non-promotional. Theoretically, we could run another big discount in August. Call it back-to-school or whatever. But with a sweepstakes, people pretty much pay full price for our products. They’re just getting entries to win something amazing.

It’s also a really cool brand-building opportunity.

We run three major sales each year, excluding Prime Day and Mother’s Day. The sweepstakes lets us create a large moment where there’s a story involved. We have this off-roading outdoor theme — we’re an adventure-adjacent lifestyle brand. We push hard into that ethos and demo.

HexClad ran its sweepstakes right after Labor Day. Why? For the same reason, October is their slowest month.

These are direct-response campaigns, not lead generation.

We tried pure lead gen a couple years ago. Even at lower costs, the quality didn’t pencil out. Hex, on the other hand, does use it to build their list heading into the holiday season. So, it depends on your audience and timing.

They create what Taylor Holiday calls a new peak in his four-peaks theory. You’re essentially generating a tent pole moment during a time when you wouldn’t have as much growth, revenue, or engagement as you would otherwise.

2. Prizes: What Will You Offer the Winners?

Your prize should be congruent with your brand.

For the last four years, we’ve been giving away off-road trucks. First year was a souped-up Wrangler, since then we partnered with Hennessey — a legendary Texas automotive house.

These are ~$100k trucks with at least $25k worth of aftermarket parts and labor.

Last year was really cool.

One of our goals was to create more discourse, so we gave someone the option to choose between a Velociraptor or a Cybertruck — which owned the zeitgeist.

We got a Foundation Series Cybertruck super early. There was this cool juxtaposition — an off-road gas-powered truck versus an absurdly futuristic-looking electric one. From a brand perspective, we could lean into either.

What did the winner choose? The cash.

There’s always a cash alternative because of legal implications. We couldn’t force someone to win the truck and then have to pay taxes on it. That would kind of suck.

HexClad’s approach was brilliant.

The winner got the most bougie trip you could imagine. First-class flight, staying at the Savoy, Michelin star dinners, cash to spend, cooking academy at Bishopsgate.

For premium kitchenware, that’s a one-to-one connection.

Connor mentioned seeing a health and wellness brand offer a $70,000 car as their giveaway. That doesn’t connect with their products, brand ethos, or what their customers want.

Why not spin up a wellness retreat somewhere in the world that’s known for yoga or health and wellness?

Everything starts with the offer.

3. Design: How Will You Brand the Campaign?

You have a larger opportunity to create something visually distinctive with a sweepstakes.

There are so many components. You have to introduce the brand, introduce the premise and prizes, introduce your products, have a call to action.

Plus, it lives in so many different places between partnership ads and websites … from our own ads, emails, and SMS to multiple landing pages. We even had fixtures in some of our wholesale partners. Next time, I’d love to do out-of-home.

Because of all that, the look is particularly important.

How do you create a design language that is distinctive, recognizable, and cohesive across multiple channels?

It’s more than cool fonts, colors, and treatments. But it is not less than cool fonts, colors, and treatments.

It’s also a way to build equity in something recognizable over time. We call it the Ridge Summer Sweepstakes. We don’t have a killer name like HexClad does — Gordon’s Golden Ticket.

The key is that if you’re creating a moment, you want it to feel distinctive visually. And if you’re doing that at the back half of every Q3 forever, you’re gonna build up recognizability.

4. Platform: Where Will You Gamify Demand?

Let me describe the simplest form of a sweepstakes. You enter for free in some capacity and then get a certain number of entries for each dollar spent.

Gamification comes as a way to shape where you drive demand.

HexClad wanted to drive non-cookware, so they had two entries for every dollar spent on accessories, three entries for aprons and apparel, but only one entry for cookware.

We do something similar by launching new products during the sweepstakes with bonus entries. We also have bonus periods where, for 24–72 hours, you’ll get 2x entries on everything. That’s the equivalent of running a sale during the sweepstakes.

Not only did we run mystery wallets with bonus entries + a discount, last year we tried bonus crates. If you checked out with a certain order value, you’d get between 25 and 1,000 entries revealed post-purchase.

It’s like a loot box. We created a bunch of different Shopify products for different entry values, assigned different weights, and used a mystery product app.

An important piece is having your sweepstakes be easily understood. Brands can sometimes overdo it with all the different entries + frequencies across categories.

For the first couple of years, we struggled with clarity. People would buy stuff without knowing exactly how many entries they’d earned. Maybe they knew they had a lot, but there was zero clarity or assurance.

What I realized was that loyalty platforms are not all that different. They track points for purchases and behaviors.

That’s when we started talking to Rivo and built out the functionality by reconfiguring something they already did.

You can log into your account and see how many entries you have. Super clear at checkout, too.

On top of the stats I shared in the intro, our 30-day repeat purchase rate during sweeps was 75% higher than our annual average. And we saw it increase 45% YoY.

5. Funnel: Who Should You Activate and How?

We’ve got the general sweepstakes experience, which is product agnostic. Then we build out funnels for each category.

If you click on a wallet ad, you’re getting pushed to a wallet-specific funnel. Same with rings or luggage.

We try to make each experience as seamless as possible to land on the page, opt into email + SMS, and shop.

We had a ton of success with our mystery wallet. Frankly, we were almost too successful. We need to find better ways to crack wallets generally.

We shipped the two trucks all over the place to film influencers because they perform 2–3x better. On YouTube, we served like 50M+ views with the trucks inside videos.

We also acquired rights to all that content, so some of our best-performing ads were mashups of the creators’ content.

Where I think we can improve …

It either needs to be really interesting and impactful content, or it needs to be a large integration. We spent too much time and energy getting the trucks into low-impact content with not a lot of views. That’s not worth the coordination.

This is a cross-channel activation.

Hex had touchpoints on literally every part of its website from homepage to collections to products. It had a dedicated landing page + mentions in the cart and at checkout as well as post-purchase emails saying how many points you’d earned.

Finally, lock in cheap and free distribution. We send emails and SMS at a 2–3x higher rate. We’re planning on doing wallet passes this year, where we can send push notifications.

Legal Compliance?

Whenever anybody asks, I refer them to Marden Kane — that’s who we’ve used four years in a row.

First thing they’ll tell you is it’s not a giveaway. Giveaway is just a marketing term. Sweepstakes is a legal term with a framework. Winners have to be selected at random by an entity outside your brand, no purchase necessary to enter.

Marden Kane handles the rules, legally required mail-in entries, bonding in states like New York and Florida. Everything.

I don’t know the exact cost, but it’s under $10k. Great value to run a buttoned-up, multimillion-dollar campaign.

What’s Next: Your Sweepstakes & Beyond

I can’t help but think ecommerce brands will get more gamified over time. Whether it’s loyalty points, an interesting way of doing referrals, or gaining access to limited-edition products, I won’t be at all surprised when shopping online feels more like playing Overwatch or something.

I saw True Classic doing this thing where you can play Pac-Man once a day, and the top 10 scores get $50 in store credit. Those sorts of experiences are sticky and lead to habitual actions.

For us, the sweeps could be a high-eight-figure campaign. I tell my team every year that my vision is for it to hit the status of McDonald’s Monopoly. But that will require enhanced word of mouth, better virality, and referral mechanics.

Hopefully, this gives you a sense of how comprehensive the execution needs to be. It’s more complex than throwing up a prize and tossing out ads and emails.

The value is there … if you line it up.

Stuart Chaney Founder & CEO, Rivo

Ridge’s Wallet Passes + WTF Is Rivo?

A few weeks ago, Connor told me they were looking to add some new components to Ridge’s 2025 sweepstakes.

He mentioned the idea of wallet passes.

Logged-in customers can one-click add a wallet pass and instantly receive push notifications to their devices.

I loved this idea so much … we built it.

Here’s how Ridge will use push notifications:

• When a sweepstakes bonus period of 2x entries drops
• Sale periods for existing customers to get extra 10% off
• Alongside email + SMS to support their other campaigns

This takes 10 minutes to set up and costs $0 to send a notification.

I know I’m shilling my product here, but this is one of the most low-lift and high-impact tactics in ecommerce today.
​
But you might be wondering …

For the last 10 years, I’ve been building and bootstrapping in the Shopify app ecosystem. We’re a retention platform — helping brands like Ridge, HexClad, True Classic, Dr. Squatch, and thousands more drive repeat purchases.

Sign more customers into your store. Create personalized retention programs. Accounts, loyalty, memberships, referrals, and more.

In addition to being Rivo’s Founder and CEO, I’m also the head of engineering. Over the last six months, we’ve completely transformed our approach to code using AI.

We’re now shipping high-quality updates (e.g., wallet passes) 10x faster. I’m sharing all of this on X, so hmu there. Or reach out to chat with our team if you’d like a full demo.

THE FEED

​Running a Sweepstake for Your DTC Brand? Here’s Your Checklist to Get It Right​

​AI Is Rewriting Our Playbook​

 BONUS #2  🎁 Marketing Operators x Meta Summit​

 BONUS #3  🎁 Operators x Meta Summit​

The Trends

Curated by the editor of CPG Wire, this week’s biggest consumer-news headlines.

1. Huda Kattan Regains Full Ownership of Huda Beauty: Grazia​

Huda Kattan, the founder & co-CEO of Huda Beauty, bought back a minority stake from TSG Consumer Partners and regained full control of the beauty brand.

TSG purchased a minority stake in Huda Beauty at a reported valuation of $1.2 billion in 2017. Huda Beauty is now one of the few founder-fully-owned brands in the beauty space. For context, Huda Beauty did north of $300 million in sales during the first eight months of 2024.

2. Humantra Grabs Funding From JamJar Investments: Endurance​

Humantra, a Dubai-based hydration brand with global aspirations, raised an undisclosed amount of funding from JamJar Investments. Humantra will use the capital to fuel its retail expansion in the UK and other international markets.

HB Investments, the family office of Huda, Mona, and Alya Kattan, incubated the brand. JamJar was established by the co-founders of Innocent Drinks (acquired by Coca-Cola).

3. Firehook Adds Becca Millstein to Board: Business Wire​

Firehook Bakery — the artisan cracker maker acquired by Forward Consumer Partners last year — has added Becca Millstein to its Board of Directors.

Millstein is best known as the co-founder and CEO of Fishwife, the viral tinned fish brand. Based on their recent collaborations, Firehook is eager to connect with younger consumers, and working with Millstein ought to help make that happen.

4. Amplifye Officially Launches: PR Newswire​

Amplifye, a biotech startup that claims to double protein absorption via a proprietary enzyme, has officially launched its flagship product: amplifyeP24.

By doubling protein bioavailability, amplifyeP24 supports benefits such as deeper sleep, enhanced muscle recovery, and sustained energy. The company also raised $18.5 million from Magdalena, Astanor Ventures, and UC Investments.

5. Alli Webb to Launch New Haircare Brand: Instagram​

Drybar co-founder Alli Webb is returning to the haircare space with Messy, a new prestige haircare brand. Messy will make its retail debut at Sephora on June 27th.

To finance the launch, Webb raised $5 million in funding from Unilever Ventures and several other investors. Webb’s previous company, Drybar, was founded in 2010. Helen of Troy acquired the business in 2020 for $255 million.

 Did you make it this far? 

Wow. Incredible.

In that case, maybe you’re the kind of deep reader and thinker who can appreciate a shameless flex.

Last week, Shopify’s President Harley Finkelstein dropped an epic comment on my post about the Operators Event.

I don’t know if one of the other “Operators” put him up to it or if it was genuinely organic. Either way, any support you can throw on Harley’s comment … would be wildly appreciated.

With thanks and anticipation,
Aaron Orendorff 🤓 Executive Editor

PS (Disclaimer): Special thanks to Rivo for sponsoring this week’s newsletter.

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