Why do failed payments slip through Stripe's automatic retry?

Stripe's smart retries recover ~50-60% of failed payments. The other 40-50% need human intervention — outdated card, billing address change, fraud lock, etc. Tycoon Agent catches the slipped ones and drafts personalized recovery emails (which convert ~30% on top of Stripe's automatic recovery).

Can she actually retry payments or send emails automatically?

Default is one-click approval for batch actions. You can flip on auto-execute for low-risk categories (retry failed payments, send card update emails). Customer-facing comms always default to draft-only because tone matters more than speed.

What if expansion outreach feels pushy?

She drafts the outreach as a value-first message, not a sales pitch ('we noticed you're hitting limits — here's how to remove them, plus 20% off the upgrade if you do it this month'). Customers usually thank you for catching it. Pushy framing kills the relationship; helpful framing strengthens it.

How much revenue can I realistically recover?

Most teams recover 60-80% of identified leaks in 30 days = typically 3-7% of monthly MRR. For a $50K MRR company that's $1,500-3,500/mo recovered. Compounds annually to $18-42K. Setting up the loop pays for itself in week 1.

Ask Tycoon Agent: Where am I leaking revenue?

You'd think you'd notice — you don't. Tycoon Agent audits 6 leak sources weekly and recovers ~3-7% of monthly MRR you didn't know you'd lost.

The short answer

Tycoon Agent audits 6 revenue leak sources every Monday and reports recoverable $$. (1) Failed payments — Stripe failed charges in the last 30 days that didn't auto-retry to success. She drafts personalized recovery emails per customer. (2) Expiring cards — cards expiring in next 60 days, automated card-update flow via Stripe + email reminder. (3) Downgrades not yet processed — customers who requested downgrade but billing didn't catch up. (4) Expansion misses — customers using >80% of plan limits not yet upgraded (Mixpanel + Stripe usage). (5) Unjustified refunds — refunds issued in last 30 days where the cause was avoidable (clear in Intercom thread). (6) Unbilled usage — usage-based features where billing didn't fire. Weekly Lark report shows total leak $$, top recovery actions ranked by ROI, one-click execution for safe items (failed payment retries, card update emails). Most teams recover 60-80% of identified leak within 30 days.

How Tycoon Agent actually does it

Audit failed payments
Stripe charges failed in last 30 days. Group by customer. Filter for those that didn't recover. Draft personalized recovery email per account.
Stripe
Catch expiring cards
Stripe cards expiring next 60 days. Trigger automated card-update flow + email reminder 14 days before expiration. Re-ping at 7 + 1 day if no update.
Stripe
Find expansion misses
Customers using >80% of plan limits per Mixpanel usage data, but still on lower tier. Draft upgrade conversation for sales/CS.
MixpanelStripe
Audit refunds for avoidable causes
Refunds last 30 days. Pull related Intercom thread. Classify cause (bug, confusion, billing error, true churn). Avoidable ones go to fix queue.
StripeIntercom
Deliver weekly report + auto-execute safe actions
Monday Lark: total leak $$, top recovery actions, one-click execution for safe items (retry failed payments, send card-update emails). Risky actions need approval.
Lark

What it looks like in chat

YouWhere am I leaking revenue?

Tycoon AgentJust ran the 6-source audit. **$8,420 recoverable in next 30 days.** **1. Failed payments: $2,840** (12 customers). Top: Acme Corp $480, Beta Industries $340. **Action: I drafted 12 personalized recovery emails. Reply 'send' to ship all.** **2. Expiring cards next 60d: $4,100/mo at risk** (47 customers). **Action: enable auto-card-update flow** (one-click), or I send reminder emails. Recovery rate ~85%. **3. Downgrades pending: $720/mo** (3 customers requested 14+ days ago, billing not updated). **Action: ship the downgrades** — customer service goodwill matters more than $720. **4. Expansion misses: $1,950/mo opportunity** (8 customers using >80% of Pro limits). Top: Gamma Co at 142% of API quota for 3 weeks straight. **Action: I drafted upgrade outreach for your CS team.** **5. Refunds last 30d: $1,200** (4 issued). 2 were avoidable bugs (now in Linear). 2 were true churn (no action). **6. Unbilled usage: $610** (2 customers — usage tracking event missed in API metering). **Action: backfill bills with apology + 50% discount on the catch-up.** **Reply 'auto-execute safe ones' (1, 2, 6) to recover $7,550 today, or pick individually. The expansion deals (#4) need your CS team to make calls.**

What you get back

Weekly Monday Lark report: total leak $$, top recovery actions per source, one-click auto-execute for safe items, drafts ready for risky ones.

Cadence: Weekly Monday 9am; mid-week emergency report if leak exceeds $5K.

Where am I leaking revenue?