Baby Boomer Income Ideas

Case Study — From CPA to $3,234/Month in 28 Days

Client Snapshot

  • Name: Robert “Bob” Chan, CPA

  • Age: 68

  • Background: 35+ years helping Main Street businesses with taxes and bookkeeping

  • Starting Point: No products, small LinkedIn network, zero email list

  • Goal: Build a low-stress, from-home income stream that isn’t tied to tax season

The Problem I Saw

Bob was answering the same cash-flow questions on repeat: pricing mistakes, late AR, “where did the money go?” – but only on 1:1 calls.

Tons of demand, no leverage, and inflation chewing on his retirement plan.

The Plan I Gave Him (15-Minute Strategy → Execution)

Positioning: “The Cash-Flow CPA for Non-Accountants—clarity in 60 minutes.”

Offer Stack (simple, fast, sellable):

  1. Core Product: Small Business Cash-Flow Kit — 13-week Google Sheets model, pricing margin calculator, AR follow-up scripts, and three 8-minute explainer videos. $49

  2. Premium: Cash-Flow Tune-Up (45-min Zoom) — screen-share, diagnose top 3 leaks, action plan. $199

  3. Recurring: Monthly Cash-Flow Huddle — group Q&A + template updates. $19/mo

Lead Magnet: “Cash-Flow in 60 Minutes: A 13-Week Template for Non-Accountants” (PDF + sample sheet).
Funnel: Opt-in → 7-email micro-course → Kit → Tune-Up upsell → Huddle invite at day 10.

Tools (no headache): Gumroad (sell), ConvertKit (email), Calendly (booking), Google Sheets (templates), Zoom (calls), Canva (PDF).

Distribution (buyers already there):

  • Two LinkedIn posts + a carousel breakdown

  • Local Chamber of Commerce 20-minute webinar (free)

  • Three Facebook groups for restaurant owners, trades, and salon owners

  • Two bookkeepers as affiliates (revenue-share links)

Build Timeline (Zero → Revenue)

  • Week 1: Nail niche, price stack, draft lead magnet + landing page.

  • Week 2: Record micro-videos in one afternoon; build Sheets models; set up Gumroad/Calendly/ConvertKit.

  • Week 3: Chamber webinar + LinkedIn launch; email course live.

  • Week 4: Add Huddle subscription; tighten headlines and call-to-action buttons.

Results (First 28 Days)

  • Revenue: $3,234

    • Cash-Flow Kit: 42 × $49 = $2,058

    • Tune-Ups: 4 × $199 = $796

    • Monthly Huddle: 20 × $19 = $380

  • Traffic: 587 visitors

  • Email Opt-ins: 163 (27.8%)

  • Kit Conversion (from list): 20% inside 10 days

  • Time to First Dollar: Day 7

  • ROI: Fee covered by Day 16; recurring revenue base established

Why It Worked

  1. Urgent, obvious pain: Cash-flow panic beats theoretical accounting every day.

  2. One slice, not the whole pie: A single 13-week model and a margin calculator solved 80% of problems.

  3. Stacked offers: Low-friction entry (Kit), trust-building mid-ticket (Tune-Up), steady base (Huddle).

  4. Native distribution: Chambers, FB owner groups, and LinkedIn = buyers with cards in hand.

Client Quote

“Jer made me productize in two weeks. The Kit sells while I’m off the clock, and the Tune-Ups are the easiest $199 I’ve ever earned.”
Robert Chan, CPA

What We’ll Tackle Next

  • Industry editions (restaurants, salons, trades) of the Cash-Flow Kit

  • Bank-recon clinic live workshop at $99/seat

  • Affiliate loop with three more bookkeepers and one POS vendor

Want Results Like This?

If you’re a professional Boomer (finance, ops, healthcare, law, trades), I’ll map your fastest path to $1K/month in 90 days—and yes, $3K+ is realistic.

I take only a few new clients each month to keep execution tight.

Book your free 15-minute Strategy Call — if you see the button, a slot’s open.

Case Study — From HR Director to $3,311/Month in 35 Days

Client Snapshot

  • Name: Sheila Morton, SPHR

  • Age: 65

  • Background: 30+ years as an HR Director for multi-location service companies

  • Starting Point: No site, no products, 1,200 LinkedIn contacts

  • Goal: Create a simple, low-stress income stream from home

The Problem I Saw

Sheila was answering the same hiring and turnover questions on repeat. How to write a scorecard, run a 30-minute interview, and keep new hires from quitting in week two.

Big demand, zero leverage, and inflation chewing through savings.

The Plan I Gave Her (15-Minute Strategy → Execution)

Positioning: “The Practical Hiring Coach for Small Businesses – great people, less drama.”

Offer Stack (simple, fast, sellable):

  1. Core Product: Fast Hire Toolkit — role scorecard templates, 5-question interview guide, 30/60/90 onboarding plan + 6 short explainer videos. $59

  2. Premium: Hiring Sprint (60-min Zoom) — write a scorecard live, build the interview, map first 30 days. $249

  3. Upsell: Day-1 Onboarding Packet — welcome script, checklist, manager “first week” prompts. $29

Lead Magnet: “The 7 Interview Questions That Predict a Great Hire” (7-page PDF).
Funnel: Opt-in → 10-email mini course → Toolkit → Sprint upsell → Day-1 Packet at checkout.

Tools (no tech circus): Gumroad (sell), ConvertKit (email), Calendly (booking), Zoom (sessions), Canva (PDFs), Google Docs (templates).

Distribution (buyers already there):

  • Two LinkedIn posts + one carousel “before/after” scorecard

  • Local chamber newsletter blurb (free)

  • Three Facebook groups for restaurant owners, trades, and home services

  • One fractional COO as an affiliate (rev-share link)

Build Timeline (Zero → Revenue)

  • Week 1: Nail niche and pricing, write lead magnet + landing page.

  • Week 2: Record 6 explainer videos in one afternoon; assemble templates; set up Gumroad/Calendly/ConvertKit.

  • Week 3: Launch via LinkedIn + chamber; start 10-email sequence.

  • Week 4–5: Add Day-1 upsell; tighten headlines; book Hiring Sprints.

Results (First 35 Days)

  • Revenue: $3,311

    • Fast Hire Toolkit: 41 × $59 = $2,419

    • Hiring Sprints: 3 × $249 = $747

    • Day-1 Onboarding Packet (checkout upsell): 5 × $29 = $145

  • Traffic: 676 visitors

  • Email Opt-ins: 194 (28.7%)

  • Toolkit Conversion (from list): 19% within 12 days

  • Time to First Dollar: Day 9

  • ROI: Fee recouped in 19 days; pipeline booked into next month

Why It Worked

  1. Urgent pain with a price tag: Bad hires and churn are expensive—owners buy prevention.

  2. One slice, not the whole HR pie: Hiring + first 30 days solved 80% of their headache.

  3. Proof over polish: Real scorecards and scripts beat theory.

  4. Offer ladder: Low-friction entry (Toolkit), mid-ticket trust (Sprint), targeted upsell (Day-1 pack).

  5. Native distribution: Chambers, Facebook owner groups, LinkedIn—where SMB buyers live.

Client Quote

“Jer forced me to stop tinkering and ship. The Toolkit sells while I sleep, and the Sprints are the easiest $249 I’ve ever made.”
Sheila Morton, HR Director (Ret.)

What We’ll Tackle Next

  • Industry editions (restaurants, trades, cleaning) of the Toolkit

  • Bulk licenses for franchise groups and agency coaches

  • Quarterly live workshop: “Hire in 7 Days Without Regret” at $119/seat

Want Results Like This?

If you’re a professional Boomer with real-world wins, I’ll map your fastest path to $1K/month in 90 days and yes, $3K+ is realistic.

I only take a few new clients each month to keep execution tight.

Book your free 15-minute Strategy Call. If you see the button, a slot’s still open.

Case Study — From Restaurant Owner to $3,322/Month in 33 Days

Client Snapshot

  • Name: Denise Kim

  • Age: 62

  • Background: 28 years as an independent restaurant owner/GM (casual dining)

  • Starting Point: No products, small LinkedIn, active in a few operator Facebook groups

  • Goal: Build a from-home revenue stream that isn’t tied to dinner rushes.

The Problem I Saw

Denise knew exactly why restaurants bleed cash, broken food costs, bloated menus, and weak vendor deals, but she was giving away fixes in comment threads.

High demand, zero leverage, inflation nipping her savings.

The Plan I Gave Her (15-Minute Strategy → Execution)

Positioning: “The Menu Margin Coach; engineer your menu to print profit.”

Offer Stack (simple, fast, sellable):

  1. Core Product: Menu Profit Kit — recipe costing sheet, food-cost calculator, menu engineering matrix, and five short “how-to” videos. $59

  2. Premium: Menu Tune-Up (60-min Zoom) — live screen-share; reprice 8–12 items; action plan for 30 days. $249

  3. Upsell: Vendor Negotiation Script Pack — email templates, call outline, reorder schedule guide. $39

Lead Magnet: “7 Menu Items That Quietly Kill Profit” (5-page PDF).
Funnel: Opt-in → 8-email micro-course → Menu Profit Kit → Tune-Up upsell → Script Pack at checkout.

No-drama tools: Gumroad (sell), ConvertKit (email), Calendly (booking), Google Sheets (templates), Zoom (sessions), Canva (PDFs).

Distribution (buyers already there):

  • Two Facebook groups for restaurant operators (case-study post + before/after menu price examples)

  • A local independent restaurant association newsletter blurb (free)

  • Two supplier reps shared her lead magnet to their accounts (rev-share links)

Build Timeline (Zero → Revenue)

  • Week 1: Nail niche, name offers, set prices; write lead magnet + landing page.

  • Week 2: Record five short videos in one afternoon; assemble Sheets + PDFs; set up Gumroad/Calendly/ConvertKit.

  • Week 3: Launch via FB groups + association; start the email sequence.

  • Week 4–5: Add Script Pack upsell; tighten headlines; book Tune-Ups.

Results (First 33 Days)

  • Revenue: $3,322

    • Menu Profit Kit: 41 × $59 = $2,419

    • Menu Tune-Ups: 3 × $249 = $747

    • Vendor Script Pack (checkout upsell): 4 × $39 = $156

  • Traffic: 610 visitors

  • Email Opt-ins: 176 (28.9%)

  • Kit Conversion (from list): 19% within 12 days

  • Time to First Dollar: Day 10

  • ROI: Fee covered by Day 20; pipeline booked two weeks ahead

Why It Worked

  1. Specific pain with dollars attached: Food-cost errors and dead-weight menu items are expensive—owners buy fixes.

  2. One slice, not the whole restaurant: Menu margins first; ops later.

  3. Proof over polish: Spreadsheet + screen-share beats studio lighting.

  4. Stacked offers: Low-friction Kit → trust-building Tune-Up → targeted vendor scripts.

  5. Native distribution: Operator groups + supplier reps = purchase-ready traffic.

Client Quote

“Jer forced me to stop giving away fixes and package them. The Kit sells while I sleep and the Tune-Ups are the easiest $249 I’ve made since happy hour.”
Denise Kim, Former Restaurant Owner/GM

What We’ll Tackle Next

  • Cuisine editions (pizza, brunch, BBQ) of the Menu Profit Kit

  • Quarterly live workshop: “Re-price Your Menu in 60 Minutes” at $99/seat

  • Bulk licenses for POS consultants and coaching groups

Want Results Like This?

If you’re a professional Boomer with real-world wins, I’ll map your fastest path to $1K/month in 90 days, and yes, $3K+ is realistic.

I only take a few new clients each month to maintain high quality.

Book your free 15-minute Strategy Call. If you see the button, a slot’s still open.

Case Study — From Project Manager (PMP) to $3,235/Month in 31 Days

Client Snapshot

  • Name: Mark Peterson, PMP

  • Age: 63

  • Background: 35 years leading construction and software rollouts (PMP, Lean)

  • Starting Point: No list, LinkedIn only presence, zero products

  • Goal: Earn from home without a billable-hours grind

The Problem I Saw

Mark was the “project firefighter” everywhere he worked, spotting schedule slippage, stakeholder drama, and scope creep in minutes.

He was still giving that away in LinkedIn & Facebook comments: high demand, zero leverage.

The Plan I Gave Him (15-Minute Strategy → Execution)

Positioning: “The Project Rescue Coach—stop the slip before it sinks the ship.”

Offer Stack (simple, fast, sellable):

  1. Core Product: Project Rescue Kit — RAID log, risk register, weekly status template, stakeholder map, and 7 short “how-to” videos. $59

  2. Premium: Project Triage (60-min Zoom) — diagnose top 5 risks, 30-day stabilization plan, owner assignments. $249

  3. Upsell: Stakeholder Script Pack — escalation emails, “slip reset” agenda, executive briefing template. $29

Lead Magnet: “7 Early Warning Signs Your Project Will Miss the Date” (6-page PDF).
Funnel: Opt-in → 10-email micro-course → Rescue Kit → Triage upsell → Script Pack at checkout.

Tools (no headaches): Gumroad (sell), ConvertKit (email), Calendly (booking), Google Sheets/Docs (templates), Zoom (sessions), Canva (PDFs), Notion (asset hub).

Distribution (buyers already there):

  • Two LinkedIn posts + a “before/after” status report carousel

  • Two PM/Agile Slack communities (with mod-approved promo thread)

  • One fractional CTO newsletter blurb (rev-share link)

  • Local PMI chapter lightning talk (free)

Build Timeline (Zero → Revenue)

  • Week 1: Niche, naming, pricing; write the lead magnet + landing page.

  • Week 2: Record 7 micro-videos; assemble templates; set up Gumroad/Calendly/ConvertKit.

  • Week 3: Launch via LinkedIn/Slack/PMI; start 10-email sequence.

  • Week 4: Add Script Pack upsell; tighten headlines; book Triage slots.

Results (First 31 Days)

  • Revenue: $3,235

    • Project Rescue Kit: 35 × $59 = $2,065

    • Project Triage: 4 × $249 = $996

    • Stakeholder Script Pack (checkout upsell): 6 × $29 = $174

  • Traffic: 628 visitors

  • Email Opt-ins: 177 (28.2%)

  • Rescue Kit Conversion (from list): 19% within 12 days

  • Time to First Dollar: Day 9

  • ROI: Fee recouped on Day 18; two Triage referrals booked for Month 2

Why It Worked

  1. Pain with a price tag: Missed deadlines and scope creep burn cash—buyers act fast.

  2. One slice, not the whole PMBOK: Risk + status + stakeholders fix 80% of project chaos.

  3. Proof beats polish: Real templates + live triage trumped fancy production.

  4. Native distribution: LinkedIn, PM Slack, PMI—exact rooms where budget holders hang out.

  5. Stacked offers: Low-friction Kit → mid-ticket Triage → targeted communication scripts.

Client Quote

“Jer turned my war stories into products. The Kit sells on autopilot, and the Triage calls are the easiest $249 I’ve made in years.”
Mark Peterson, PMP

What We’ll Tackle Next

  • Jira/Asana template pack (tool-specific editions)

  • Team license for agencies and internal PMOs

  • Quarterly live workshop: “De-Risk Any Project in 60 Minutes” at $119/seat

Want Results Like This?

If you’ve got decades of real-world wins, I’ll map your fastest path to $1K/month in 90 days—and yes, $3K+ is realistic.

I only take a few new clients each month to keep execution tight.

Book your free 15-minute Strategy Call. If you see the button, a slot’s open.

Case Study — From VP of Sales to $3,426/Month in 29 Days

Client Snapshot

  • Name: David R., VP of Sales (Ret.)

  • Age: 66

  • Background: 35+ years building B2B sales teams (SaaS + industrial)

  • Starting Point: No list, LinkedIn-only presence, zero products

  • Goal: Create a from-home income stream without managing reps or quotas

The Problem I Saw

David had a million-dollar skill set locked in war stories, discovery, objection handling, and pipeline math, but he was giving it away in comment threads.

Tons of demand, zero leverage, and inflation biting his retirement.

The Plan I Gave Him (15-Minute Strategy → Execution)

Positioning: “The Practical Sales Coach—fix your discovery, kill objections, grow pipeline.”

Offer Stack (simple, fast, sellable):

  1. Core Product: Discovery Call Blueprint — 9-question discovery map, deal-qual scorecard, call notes template + 6 short videos. $59

  2. Premium: Pipeline Triage (60-min Zoom) — live audit of 10 deals, next-step scripts, 30-day plan. $249

  3. Upsell: Objection Vault — 25 “land-the-plane” scripts for price, timing, and “send me a proposal.” $39

Lead Magnet: “7 Discovery Questions That Close Deals Faster” (5-page PDF).
Funnel: Opt-in → 10-email micro-course → Blueprint → Triage upsell → Objection Vault at checkout.

No-drama tools: Gumroad (sell), ConvertKit (email), Calendly (booking), Zoom (sessions), Google Docs/Sheets (templates), Canva (PDF), Notion (asset hub).

Distribution (buyers already there):

  • Two LinkedIn posts + 1 carousel (“before/after” discovery notes)

  • RevOps/SDR Slack communities (promo thread approved by mods)

  • A fractional CRO newsletter blurb (rev-share link)

  • Alumni sales group on Facebook

Build Timeline (Zero → Revenue)

  • Week 1: Nail niche, price stack, write lead magnet + landing page.

  • Week 2: Record 6 micro-videos; assemble templates; set up Gumroad/Calendly/ConvertKit.

  • Week 3: Launch via LinkedIn/Slack/alumni group; email course goes live.

  • Week 4: Add Objection Vault upsell; tune headlines and CTAs; book Triage sessions.

Results (First 29 Days)

  • Revenue: $3,426

    • Discovery Call Blueprint: 33 × $59 = $1,947

    • Pipeline Triage: 5 × $249 = $1,245

    • Objection Vault (checkout upsell): 6 × $39 = $234

  • Traffic: 654 visitors

  • Email Opt-ins: 184 (28.1%)

  • Blueprint Conversion (from list): 19% within 10 days

  • Time to First Dollar: Day 8

  • ROI: Fee recouped on Day 17; two Triage referrals booked into Month 2

Why It Worked

  1. Concrete pain with $$$ attached: Bad discovery and stalled deals are expensive; buyers move fast to fix them.

  2. One slice, not “all of sales”: Discovery → objections → pipeline. Tight scope, clear wins.

  3. Proof > polish: Real notes templates + live triage beat any glossy theory.

  4. Native distribution: LinkedIn, sales Slack, and fractional CROs already sit next to budgets.

  5. Stacked offers: Low-friction Blueprint → mid-ticket Triage → targeted Objection Vault.

Client Quote

“Jer got me selling in two weeks. The Blueprint sells on autopilot, and the Triage calls are the easiest $249 I’ve made since my last quota crush.”
David R., Former VP of Sales

What We’ll Tackle Next

  • Team license for agencies and founder cohorts

  • Tool-specific editions (Salesforce, HubSpot) of the templates

  • Monthly live clinic: “Fix 3 Deals in 60 Minutes” at $119/seat

Want Results Like This?

If you’re a Boomer with real-world wins, I’ll map your fastest path to $1K/month in 90 days—and yes, $3K+ is realistic.

I only take a few new clients each month to keep execution tight.

Book your free 15-minute Strategy Call. If the button’s visible, a slot’s open.

Baby Boomer Income Ideas