Exited my eCommerce brand | Co-Founder at Workspace6.io & MediaSpace | Helping B2B startups understand brand psychology to boost sales

I started a B2C brand with $188 at 17. Grew it to 8-figures in sales and sold for 7-figures.     Then I co-founded a 1,000 member private community for 7-9 figure operators. Combined member revenue is over $13bn.     Now I run Redux Payments, where we use AI to recover failed payments and fix involuntary churn for B2C subscription businesses.     This is the problem I’m obsessed with solving. I write about what I find, what works, and what doesn’t. I’m always down to nerd out if you want to jam!     ————————————————————————      Now building:    Redux Payments (reduxpayments.com) - Stop losing revenue to failed payments. We slash involuntary churn and grow ARR by 8%+ for subscription businesses by using AI to recover failed payments.————————————————————————      You can reach me via email: philip (at) reduxpayments.com

Philip Pages - workspace6

100+ Stripe audits and I missed this. 

Last week I spoke with a former J.P. Morgan payments consultant.

A B2C subscription company hired him after Capital One stopped approving all their transactions.

In Stripe, their chargeback rate was under 1%. Nothing looked wrong.

But something was very wrong...

He showed me a hidden number in Stripe that was 8x higher than the chargeback rate.

"This is what issuers are actually looking at."
__

He called it the claim rate.

Chargebacks + Early Fraud Warnings.

Here's what I didn't know:

When a customer tells their bank "I don't recognize this charge," the bank files an Early Fraud Warning with Visa.

No chargeback, no notification. The merchant sees nothing.

But Visa counts it. The issuer counts it. And they use it to approve future transactions.

This company had 5–7% of transactions flagged as EFWs. 

They had no clue.
__

Capital One saw the real number (8% including EFWs, not the 1% in Stripe) and shut off all approvals.

The merchant crossed a threshold they didn't know existed, based on a metric they never checked.
__

HOW TO CHECK YOURS

Go to Stripe Dashboard → Payments Analytics → Disputes.

EFWs show up there and in payment logs.

It's visible but buried deep enough that in 100+ audits, I never looked until last week.

If I missed this, most B2C subscription companies are too.

Go check yours.

Philip Pages

CEO @ Redux Payments | Stop losing money to credit card failures | Exited Founder

We're signing $50M/year companies. We're competing with teams 10x our size. And we're winning.   

Redux Payments has a core team of 9. Engineers, machine learning, go-to-market. 

Everyone owns something end-to-end. No one is riding coattails.

I'd rather have 9 people who are absolute killers than 90 who are just filling seats. 

Here's what I've learned building this way:

1/ Small teams move faster. 
There's nowhere to hide. Every person either contributes or the whole thing breaks. That pressure is a feature, not a bug.

2/ Ownership isn’t for everyone. 
Some people thrive when they’re accountable for the result. Others don’t. We've had to let people go who couldn't keep up with the pace. It sucks, but carrying dead weight on a team this small will sink you.

3/ Care shows up in the details 
Last week, a customer hit a bug. Our engineers shipped a fix the same day. That’s what happens when everyone actually cares about the customer. You don't get that at a 200-person company where the ticket sits in a queue for 3 sprints.

I’ve watched incumbents with massive teams get slow, bureaucratic, and complacent. In this new era, a small, hungry team that moves fast will run circles around them every time.

9 killers > 90 coasters

Last month, an iOS app doing $2.1M/MRR on Stripe came to us struggling with trials not converting. What I found was almost too obvious.

Trial starts looked great. Meta was performing. But nothing was converting to paid.

Their team was blaming the product, the onboarding, the pricing.

Then I pulled the card-level data.
__

Stripe doesn't surface this by default. You have to pull it from the API and I only know to look because I've audited over 100 Stripe accounts.

Credit cards? Normal failure rates.
Debit cards? Fine.
Prepaid cards? 95% failure rate.

Prepaid cards were 10% of their card mix but 25% of all payment failures. One in four failed payments was a card that was never going to convert.

Their Head of Growth told me: "We had no idea prepaid was even a category we could filter by"
__

A user sees the ad. Downloads the app. Signs up for a free trial with Apple Cash or a prepaid card with $2 on it. The $0 auth goes through. Trial count goes up.

7 days later, the real charge hits. There's no money on the card. It fails. It will keep failing.

No retry strategy in the world is going to put money on an empty prepaid card.
__

HOW TO CHECK YOURS

Pull your charges from the Stripe API or Sigma. 

Filter by card.funding = prepaid. Compare trial-to-paid conversion against credit and debit.

If prepaid is a growing % of your trial mix, you have a problem you're not measuring.

The fix isn't complicated. 

Detect prepaid cards at trial signup. Block them, require a micro-charge to validate funds, or route them into a separate cohort so your metrics stay clean.

You might find that 25% of your "growth" isn't real.

I personally tested Headspace’s payment recovery flow and, honestly, expected way more.

I signed up for a 7-day trial ($12.99) using a card with only $1 to see how they'd handle failed payment retries.

June 26th: First charge failed.

They sent a "your last payment didn't go through" email and began retries:

June 27th, 8:03am
June 28th, 8:19am
June 29th, 9:03am

After three attempts in three days, they cancelled the subscription.

PROBLEMS:

Retries all around the same timeframe tell me they're fixed "dumb" retries.

If these were spread out with seemingly randomized date/time patterns, that would tell me that they're using an intelligent model that's adapting the retries. 

But there’s no intelligent modeling here, no adaptation for paydays, month-end cycles, or specific bank error codes. 

Compare to Hulu. When their transaction fails, they retried me 13X over a 50-day window. 

That's 7 weeks of recovery opportunities Headspace abandons after 72 hours.

*Backend Recovery Logic Rating* = D 

Looking at their recovery emails, I really liked their copy: “Is this really goodbye?”, but their strategy behind it is flawed. 

They trigger an email with every single retry. 

Every email slightly increases chances of voluntary churn, so their goal should be the opposite: Recover as many transactions as possible behind the scenes so the customer never even knows there was a problem. 

*Recovery Email Strategy Rating* = C+ 

Overall, for their web based failed payment recovery I'd give Headspace a C. 

It’s wild to see a company of this scale leaving so much money on the table. It proves that even for the giants backend recovery is rarely on the radar. 

There is a massive amount of "found" revenue waiting for any brand willing to move past basic retry logic and actually upgrade their stack to solve it.

Head of Growth: "failed payments were $419K. Stripe's recovering 28%."

CFO: "WTF. that’s not what my numbers say. what does that 28% include?"

Head of Growth: "subscriptions that failed and got retried. it's right there in the recovery dashboard."

CFO: "does it include trial-to-paid failures?"

Head of Growth: "...what do you mean?"

CFO: "go to your Stripe revenue recovery page. hover over the info icon next to 'failed payments.'"

Head of Growth: "it says... 'excludes failures on the first payment after a trial.'"

CFO: "meaning every free trial that tried to convert to paid and failed? not in that number."

Head of Growth: "how many trials failed last month?"

CFO: "I pulled it. $550K. just from trials."

Head of Growth: "that's more than our entire subscription failure volume."

CFO: "and zero of it shows in your recovery dashboard. zero of it hits your 28% rate."

Head of Growth: "so the real number isn't $412K..."

CFO: "it's close to a million. and your recovery rate on trials? under 8%."
Head of Growth: "8%?? how is that possible?"

CFO: "prepaid cards. users with $2 in their wallet signing up for a free week. 10% of your card mix. 25% of all failures. 95% never convert."

Head of Growth: "and Stripe retries them the same way as everything else?"
CFO: "four attempts. same generic logic. gives up. no one notices because it's not even on the dashboard."

Head of Growth: "so our churn graph looks stable..."

CFO: "while the trial funnel bleeds out before we ever collect a dollar."

Head of Growth: "how long has this been happening?"

CFO: "$1.4 million in invisible trial failures. last 3 months alone."

Head of Growth: "this is priority one."

CFO: "now we're talking."

Work from home is a scam and anyone who says they're more productive at home is lying. 

These are the 2 worst things 2 years of it cost me:

1) Mentally lost track of the competition. 

Seeing people show up day in and day out and grind toward a goal is a visual reminder of the effort it takes to actually build something real. 

If other people are doing it, you’ve gotta do even more. 
That pressure’s non-existent sitting alone at home. 


2) It killed serendipity. 

I never would’ve met my Redux Payments co-founder if we hadn’t been at the same Austin WeWork.

Years back, we were both working on opposite sides of the floor, doing our own thing. 
And every day like clockwork people would start heading home at 5pm.  
But he stuck around past 7, 8, 9:00, until the overhead motion detection lights went out and the cleaning crews started making their rounds. 
We didn't talk for weeks, maybe months. Until one day we started talking about AI or something. And just kept talking. 

We recognized the same thing in each other: the willingness to grind, work long hours, and get shit done.

That kind of thing doesn’t happen when you’re burning the midnight oil alone at home. 


It’s an anecdote of one, terrible I know. But I’ve never heard of a notable figure making it into the history books by doing anything in complete isolation. 

So yeah. I’m back at my old WeWork, working around people again. And a month in, it’s already a game changer.

Matthew Holman

Subscriptions Leader: Consultant, Newsletter, Podcast | Events | Communities | Commerce Catalyst | Partnerships @QPilot | Formerly Incarcerated

Most people don't see subscriptions the way I do.

For many of the brands I come into contact with, subscriptions are about retention. Figuring out how to keep people longer to drive up lifetime value (LTV).

But subscriptions are much more than LTV and recurring revenue. They are a way to engage with your best customers, provide more value, and capture more value in return. When looked at through an acquisition lens, subscriptions become less about retention and more about customer experience.

That's what we do at Subscription Prescription - craft acquisition and retention experiences to unlock greater profitability and sustainability for your business.

Message me to learn more about how we can improve acquisition of subscribers, retention of subscriber, and the profitability of subscribers with our approach. Unlock new growth for your business with the right prescription for your subscriptions.

Partner, Cofounder

Patterns in the Cloud builds fun software for commerce

Looking for a great deal on tickets for Ecom Elevated next month?

Yes, Commerce Catalyst has another big ecom conference. :)

We've run a few promotions, but with a new ticketing platform it's easier to offer some special discounts.

So, if you're interested in hearing from people like Dan Griffiths the CEO of Lume, or Akwasi Frimpong OLY an Olympian and Senior Manager of Partnerships at Momentous... or any number of our incredible sessions, then here is the deal:

Brand Tickets are $99 until March 15th. Then they're $150, then $199.
Saas/Service Tickets are $170 until March 15th. Then they're $249, then $349.

Grab them before prices go up! https://lnkd.in/gnsM__y8

D2C Subscription Agency | Weekly Subscription Tips --> Newsletter + Podcast | Commerce Catalyst Community | Partnerships @QPilot

Open article: Ecom Elevated Spring by live.eventtia.com

While everyone is thinking about AI completely replacing software, you get great product releases like this one that use AI incredibly well:

- You install
- AI analyzes repeat purchase history
- AI determines the timing to send messages
- AI writes the messages with offers based on parameters you set

Customers buy on rePete.

AI right now is making implementation and configuration a no-brainer, enabling powerful customer experiences like this one.

🎙️Shopify1Percent Pod • BOLD Co-Founder • EY Entrepreneur of the Year ‘18 • @Shopify Partner ‘12 • Merchant ‘98

It is my extreme honor to introduce to you the newest member of your Shopify family: Meet rePete 👋

Like your favorite barista, rePete remembers your pace and nudges you when it's time. He's your smart, friendly AI reorder agent  that builds a dynamic reorder prediction for each individual customer. When they are running low, he sends a polite nudge, helping them easily restock with just ONE click! 🎉

Because, let's face it. Your life doesn't revolve around a fixed 30-day cycle.
Your customers want to reorder on their own terms, and at their own pace. They want replenishment that feels natural, not a fixed cycle disguised as convenience.

While subscription fatigue is at an all-time high and more customers are canceling subscriptions than ever before, there is good news! Most customers still want their products replenished, they just don't want a subscription.

And that's exactly why they love rePete so much ❤️

Instead of forcing customers onto a fixed schedule, rePete learns each customer's individual buying behavior and purchase patterns. He analyzes thousands of data points everywhere they shop, so he can send a friendly nudge at the perfect predicted time they're likely ready for a refill.

Predicted. Not scheduled. On-demand, not forced.

rePete is free to install, and his pricing is very simple: if he doesn't make you money, you don't pay a penny. He works entirely on commission. No per-SMS fees. No per-email costs. No app fees...

The future of repeat commerce isn't a subscription. It's a prediction.

#shopify #reorders #ecommerce #shopifyplus #repete

The top 5 things I'd do to improve a subscription program with little time.

I'll list them by potential impact for your business:

1. Default to subscribe and save with some simple design changes to make the subscription option more prominent.

Impact: 30-40% opt-in rate (minimum) - more subscribers coming in

2. Upsell to subscriptions in the cart. Simple, straightforward, but effective.

Impact: additional 10% improvement to opt-in rate

3. Make the billing reminder feel like a value reminder than a transaction. Show them why they subscribed in the first place.

Impact: lower monthly churn 10-15%

4. Update the cancel flow with better copy, stronger offers to stay, and a founder video on the splash screen when someone first cancels.

Impact: minimum 10% improvement on your cancel save rate

5. Make the onboarding flow feel educational and welcoming. There are so many questions people have; show them how you're different and how they can be successful with you.

Impact: lower MoM churn by 5-10%

Where do you think some of the best retention expertise comes from?

You might think an email agency, or growth background.

Sure, those people have a ton of skill. But there's something special about someone with a background in customer success when it comes to retention.

They already know the people. Know how to communicate with them.

They understand timing - not just for comms but in upsells and product usage.

That's why this week's dose is so special! We were lucky to sit down with Jade Moffatt from DIRTEA to talk all things retention.

Three great takeaways: strong education onboarding, timing your cross-sells, and how to better segment winbacks.

Let's dive in!

View newsletter: Subscription Prescription

Matt here with your weekly Subscription Prescription 💊 A big part of retention is timing. Not just how often you communicate, but what and when. In t

Open article: Dose #193: Education, Cross-sells, and Winbacks by Matthew Holman • 5 min read

Dose #193: Education, Cross-sells, and Winbacks

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