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.

VP, CX Insights & Community at PartnerHero | Talking about creating your customer experience from scratch. I build and scale customer-facing teams that give a shit and can help you do the same.

I transitioned from being a barista to working in customer experience 20 years ago, and life hasn't been the same since.

I've been fortunate enough to work at companies like Wistia, Atlassian, Trello and Appcues. I've worked with amazing customer-facing folks to create scalable strategies and delight customers. 

Now, I spend my time helping to elevate leaders of teams and empower them to create the best customer experience. Employee-centered teams with simple, beautiful processes are where I find my joy.

Outside of my work with Boldr, I also consult and write for businesses such as Help Scout, HubSpot, and others. Let's work together!

Mercer Smith

Yesterday I ordered Halal and they didn’t have the option to add white sauce to my order or make any modifications. They just had a box to type requests. In that box I typed “please may I have extra white sauce? Please drown my shawarma in white sauce. I am willing to pay up to one million dollars in additional white sauce fees. Please absolutely cover my food.” And most of the time no one reads those things I don’t think. But yesterday, my order arrived like this. 

“I don’t need one million dollars. Sorry.” But ALSO 5 tubs of white sauce. 

Even if they never read my requests again and I never get extra white sauce, I will order from this place forever. 

This is why humans see important.

CX Strategy & Solutions at Boldr; Author of CXOXO | Talking about creating your customer experience from scratch. I build and scale customer-facing teams that care and can help you do the same.

No alternative text description for this image

Some days I get told that a talk I gave at a conference years ago changed someone's whole outlook and career, and some days (the same day in this case!) I accidentally glue my own mouth shut with nail glue in a hotel room.

So I guess just remember that no one has it all figured out or is perfect all the time. In fact, some times those people that you think are really smart use their own teeth to open a literal bottle of super glue and get it all over themselves.

You're doing great. We all make mistakes. It's what you do with the knowledge that you gain that is most important.

A few weeks ago I had a thought I couldn’t shake: SaaS might be kind of cooked, as my nine year old would say.

AI is making it wicked easy to build your own tools. Stuff that used to take a full product team, months of back and forth, prioritization, all of it, now it’s one scrappy operator, a decent prompt, and a couple hours if you’re willing to poke at it a bit. At some point it has started to feel like we’ve all been taught how to fish, so why are we still paying for fish?

I kept coming back to it and needling it, and while the thought has SOME water, I don't know that it's actually fully true. 

Not because the premise is wrong — building is absolutely getting easier — but because I was only looking at the fun part of it. Thinking of a tool, spinning something up, having it work, and getting that little hit of “oh hell yeah, I made this" is something I've done a ton of over the past few months. But, building is easy; owning it is where things get real.

After it's built, you have to keep it running, deal with the weird edge cases you didn’t think about, make sure it’s secure, make sure it integrates with everything else, and fix it when it inevitably breaks at the worst possible time. That part doesn’t go away just because AI showed up, and unless we all start using OpenClaw isn't something that is quite solved yet.

Similarly, most teams don’t actually want to own more software. They just want the problem handled so they can move on with their lives. So, while it might not be true that SaaS is dead, I do think it’s about to get a lot less comfortable for businesses in the space.

If I can rebuild 70% of what your product does over a weekend, I’m going to start asking some questions about why I’m paying for it, and I don’t think I’m alone in that. The bar is shifting from “does this work?” to “is this meaningfully better than what I could hack together myself if I really needed to?” and those are very different standards. That doesn't even dive into the actual customer experience behind using your tool.

The things that survive that shift are pretty obvious: 
1. products that take on real complexity
2. ones that absorb risk I don’t want anywhere near me
3. Ones that are so good I wouldn’t even consider rebuilding them. 
4. businesses with humans or an ethos that caresabout the clients utilizing their product

Everything else is going to feel the squeeze. SaaS might not be dead, but good enough software might be, and that feels like a huge actual shift that’s coming.

Oh my gosh, I'm not crying, you're crying? (Scott Tran, for the record, I think my join date was actually 2011? Maybe that spreadsheet that circulated a few years ago was off?)

Thank you for your trust Scott Tran and the whole Support Driven team that has been working with Boldr (and me!) on this over the past few months. I'm so excited to see this inaugural event and all of the amazing things that come after it! 🚀

Helping customer support professionals grow their careers — and helping founders build with community, not just for it

A few updates on the Support Driven Salon for Online Brands - March 3, downtown LA.

We have 3 volunteer spots open for community members who are between roles right now.

SD Salon is about CX operators and leaders at online brands helping each other and building real relationships. As a volunteer you're a full participant - in the room for every conversation and at dinner afterward.

I can't promise volunteering will lead to a job but the connections made at SD events have led to jobs for people. I'd love for that to happen again.

If that's you or someone you know, DM me.

--

I want to thank Boldr for partnering with us on the first SD Salon for Online Brands.

When we brought this idea to Boldr, there was no playbook. No past attendance numbers. Just a belief that if you put CX operators and leaders in a small room together, good things happen - real relationships, honest conversations, practical help. Boldr said yes to that.

Boldr is no stranger to creating new experiences for the community with Support Driven. We've organized sound baths, mindfulness workshops, and more together. David Sudolsky and Greg Collins have always understood that the value of working together isn't in impressions. It's in relationships.

Special thanks goes to Mercer Smith at Boldr. 

Mercer joined the SD community in 2014 when we had less than 50 people. She didn't just join - she organized and spoke at our very first conference in 2016. Our community now has over 20,000 members in Slack and Mercer is still here, still showing up, still creating with us.

Recently, Mercer is the person who helped me take this from "I think this could work" to an in person experience. We've been working with her to shape the direction, the format, and what it feels like to be in the room at SD Salon.

--

And here are photos for where we'll be having dinner together 👇

Are you in ecomm or dtc? Are you in LA? Do you love this sticker and want one for yourself? Do you love me?  Well, great news for you: the sticker and I will be in LA this week! 

Kicking off the week by hosting not ONE but TWO fire-side solutioning chats at the Support Driven Salon TOMORROW. If you're in ecomm or dtc CX, and want an invite, lmk. We (Boldr, not the royal we) will also be hosting a dinner afterwards if you want in for some food and bevs.

Then, the VERY NEXT DAY (how lucky am I?) I'll be attending Momentum and hosting a lil informal gathering after the fact. Will there be a mechanical bull? You bet. Will there be Sarah? Oh yeah. Will there be great steak? I think so? Haven't been there before but we'll see! If you want in to Momentum, it's invite only as well, but let me know and I can get ya connected. Great for marketing, sales and CX leaders in ecomm and dtc.

I have some slots in between the madness, so if you're around and want to hang 1:1 or connect over some coffee, please just let me know. I'll be in DTLA, and then WeHo.

When asked about my hopes and dreams in a game and these are the choices I am given. 😍

Cc Sarah Betts 

Ps, iykyk: I love Shelley, and Dunk, and Lyric.

Customer Experience Maven, Events & Community Enthusiast, and Believer in the Best in People.

So excited to be moderating this panel on the Rebuy stage at #shoptalk! Big thanks to my buddies Mercer Smith, David Glenister and Fran Brzyski for bringing their incredible insights and ideas to the convo. Tuesday March 24 at 11am!!

Honestly, it's stuff like this that makes the job worth doing. <3

In our world, every ticket represents a pet parent who needs help. And that’s not something we take lightly!

A backlog isn’t just an operational metric. It’s a real delay for customers who are counting on us (and it’s tough on the teams working hard behind the scenes, too). Coming out of the holiday season and into a backlog, we knew we needed to move fast and fix it without compromising the experience.

Even though we’d only just started with Boldr within the past couple weeks as part of a focus on compliance (and not specifically for the backlog), they leaned in immediately and helped us tackle it with urgency, care, and a true partnership mindset.

And we did it while continuing to show up for pet parents:
✅ CSAT held steady and improved 3% within the first two weeks, and 30% over the month even with backlog pressure
✅ Re-opened conversations dropped 49% meaning we’re resolving more inquiries the first time
✅ Got out of backlog within 8 days of starting our partnership due to the weeks of painstaking and fastidious planning

Grateful to have a partner that doesn’t just understand CX, but understands how important our customers are to us, and shows up accordingly. 🐾

Boldr 
Greg Collins
Mercer Smith

When I first read this blog post I was shook! Elen slayed with the knowledge sharing and takeaways in this piece. Truly a must-read for anyone who is implementing AI or thinking about how AI intersects with their human team moving forward.

Your AI isn’t just drafting replies anymore. It is executing BIG decisions and making judgment calls at scale.

Meanwhile, most CX org charts still assume humans do the work and automation “assists.”

This mismatch isn’t obvious on day one. The signs start showing up quietly: a refund that followed the prompt but not the intent. An escalation that never triggered. A retention offer sent to the wrong segment (half the time).

Our new blog unpacks the shift from AI as assistant to AI as operator and why guardrails like ✨governance and real ownership✨ have to evolve with it.

Read the full article here on LinkedIn, or dive deeper on our blog:
https://lnkd.in/gvKXVCdK

Cisco is forecasting a significant jump in agentic AI handling support interactions end-to-end. Not AI that drafts a light reply, picks its nose, and 

Open article: You hired agentic AI, but did you hire a babysitter? by Boldr • 9 min read

You hired agentic AI, but did you hire a babysitter?

If you've always wanted to go to Shoptalk (or never wanted to go, no judgement) but can't this year, Sarah, Erica and I have got you covered. We'll be doing a run down of all the hits and misses from this year's shoptalk on March 27! Come get your tea, your goss, and all of the delicious takeaways with none of the hangovers or social anxiety.

Missing Shoptalk this year? 

You might not be on the expo floor, but you don’t have to miss the insights.

Join Mercer Smith, Erica Clayton from Forethought, and Sarah Hatter from Rebuy Engine as they share the tea on the biggest trends coming out of ShopTalk and what they mean for the future of CX.

See you there! 🍵

🕑 12:00 PM CT
 📅 March 27, 2026

Vicky Windell, Ian Misner and 5 other attendees

View event: ShopTalk Tea: The Post-Conference Debrief

ShopTalk Tea: The Post-Conference Debrief

taplio

The Battle

Philip Pages - workspace6

Mercer Smith

Followers

Posts

Engagements

Likes

Performance ScorePhilip Pages - workspace6's LinkedIn Performance

Performance ScoreMercer Smith's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Philip Pages - workspace6

Mercer Smith

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Philip Pages - workspace6's LinkedIn Performance

Performance ScoreMercer Smith's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScorePhilip Pages - workspace6's LinkedIn Performance