What We Know

• WLKS retention at 25%

• ~13% monthly churn

• Time-to-value slow

• Acquisition breakeven on front end

• 1% conversion to Collective

This is not an acquisition problem.
It’s a time-to-value and retention problem.

Revenue Diversification

• While strengthening retention and time-to-value, I would run small, controlled experiments testing direct-to-Collective acquisition.

• Given Collective’s higher retention and LTV, a profitable CAC threshold is materially higher.

• The goal would be to validate demand and unit economics before scaling spend without increasing overall ad budget.

Let Me Explain (click for loom)

90-Day Plan

Weeks 1–2:

• Map real customer journey

• Interview members

• Audit onboarding + engagement

Month 2:

• Redesign onboarding architecture

• Clarify ownership of community

• Automate repetitive ops tasks

Month 3:

• Implement retention playbook

• Launch referral seed system

• Build Collective bridge process

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Ops Overwhelm

• Automate member approvals

• Centralize FAQ with AI/help desk

• Standardize event SOPs

• Assign clear owner for community health

• Remove manual processes from founders

Let Me Explain (click for loom)

Email 1 — Day 0 (Immediately After Joining)

Subject: You’re In. Here’s What Happens Next.

Goal: Reduce uncertainty. Establish clarity + safety.

Core Message:

• Welcome to WLTH WLKS.

• How matching works (timeline, expectations).

• What to expect in first 30 days.

• Introduce the 15-minute Welcome Call with a WLTH team member.

  • As an added retention lever, I would consider offering a brief 15-minute Welcome Call with a WLTH team member. This small human touchpoint could meaningfully increase match acceptance, engagement and trust in the first 30 days, and overall retention.

• Reinforce: this works best when you engage intentionally.

Action Step:

• Book your 15-minute Welcome Call (Calendly link).

• Complete your profile (link).

• Confirm availability for first match window.

This eliminates “I thought someone would just handle it.”

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Email 2 — Day 1

Subject: How to Get Real Value from WLTH (Most Members Miss This)

Goal: Accelerate time-to-value.

Core Message:

• WLTH is not passive networking.

• The founders who get the most value do three things:

  1. Show up prepared.

  2. Share honestly.

  3. Follow up intentionally.

• Introduce a short “Momentum Check” AI-powered quiz:

  • Where are you right now?

    • Launching

    • Scaling

    • Stuck

    • Exploring

• Based on answers:

  • Resource suggestion

  • Relevant event

  • Relevant member spotlight

This signals personalization early.

Action Step:

• Take the 2-minute Momentum Check.

• Set your 30-day intention inside WLTH.

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Email 3 — Day 3

Subject: Before Your First Walk, Read This.

Goal: Remove friction and guesswork around the first meeting.

Core Message:

• Normalize first-meeting nerves.

• Provide simple structure:

  • Share current revenue stage.

  • One win.

  • One challenge.

  • One ask.

• Provide 5 suggested questions to guide the conversation.

• Emphasize: clarity creates better connections.

This reduces awkwardness and increases perceived value.

Action Step:

• Write down your one goal for this walk.

• Add it to your calendar event notes.

• Confirm your match attendance.

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Email 4 — Day 5

Subject: Make Your First WLTH Win Happen This Week

Goal: Create micro-success before the first official match.

Core Message:

• Momentum builds belonging.

• Invite them to:

  • Introduce themselves in the app/community thread.

  • Comment on one other founder’s post.

  • RSVP to an upcoming event.

• Reinforce: you’re not invisible here.

Optional Personalization:
If Momentum Quiz indicated:

• Scaling → Invite to advanced roundtable.

• Launching → Invite to fundamentals workshop.

Action Step:

• Post your intro.

• RSVP to one event.

Low friction. Immediate engagement.

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Email 5 — Day 7

Subject: Who Should Be Walking With You?

Goal: Plant referral seed + reinforce belonging.

Core Message:

• WLTH works best when the room is strong.

• If someone came to mind this week, invite her.

• Quality > volume.

• You help shape the community.

Position referral as stewardship, not marketing.

Action Step:

• Share referral link.

• Or nominate someone confidentially.

Let Me Explain (click for loom)

15-Minute Action + Delegation

Broken Onboarding

• Pause new onboarding traffic if possible, pull a timestamped list of all affected applicants, and assign a team member to audit the automation + manually contact anyone impacted within 24 hours.

VIP Recovery

• Personally respond within 30 minutes to acknowledge and request a same-day call, while assigning a team member to review their match history and engagement notes before that conversation.

Podcast Landing Page

• Define the single conversion goal (email capture, WLKS join, or Collective interest) and assign a rapid-build landing page sprint with clear copy and deadline ownership.

Let Me Explain (click for loom)

Org chart at $5M:

1x COO
1x Head of Community

2x Membership Relationship Coordinators

1x Head of Growth

1x Ops Manager

1x Head of Tech and Support

My calendar:

40% team + goal setting/review

20% growth strategy

20% systems + ops

20% product + retention

Revenue Evolution

• WLKS price tiering or annual option
• Collective expansion
• Upsell pathway clarity

Let Me Explain (click for loom)

Community businesses are strongest during peak experiences — events, matches, retreats.

But churn rarely happens during the high points.
It happens in the silence between them.

In those in-between moments, members can:

• Lose momentum

• Feel unseen

• Question the value

• Drift quietly

If WLTH is to scale sustainably, the in-between must be architected with as much intention as the flagship experiences.

 

Added touch points may include:

• Birthday card
• Hand-written "welcome" note
• Founder success stories highlighted

Let Me Explain (click for loom)