Cashflow Diary

Name

Cashflow Diary

Legal name

West Egg Enterprises, Inc.

Website

https://cashflowdiary.com

Company type

Private

Founded year

2011

Operating status

Operating

Headcount range

11–50 employees

Short description

Cashflow Diary (West Egg Enterprises, Inc.) is an online education and consulting platform that trains short-term rental entrepreneurs through tiered memberships, paid SOAR consulting engagements, AI toolkits, and workflow products. Founded by J. Massey, it serves aspiring and active STR operators with proprietary frameworks and a 10,000+ member community.

Ownership category

akta.pro rank

Product category

Short-Term Rental Education and Consulting

NAICS

Other Management Consulting Services (541618), Software Publishers (5132)

SIC

Services-Management Consulting Services (8742)

akta.pro primary industry

Financial Education & Coaching (Digital Programs, Tools) (FSAGADAH)

Keywords

• Short-term rental education
• STR consulting services
• Rental arbitrage training
• Real estate coaching
• STR membership community

Headquarters

HQ city

Foothill Ranch

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Marketing or Sales, Technology or R&D, Operations, Others

Revenue model

1. Membership Subscriptions: Three-tier membership model: Free (Journey) tier with podcast/newsletter access; Operator tier at $197/month with full community, AI Tool Library, monthly Q&As, and Resource Vault; Elite tier at $997/month adding 1:1 STR consulting sessions, Private Deal Network access, and VIP Mastermind Retreats. The membership drives recurring monthly revenue with high-margin digital delivery.
2. SOAR Consulting Services: Three consulting tiers built on the SOAR framework (Situation diagnostic, Opportunity analysis, Action plan, Results tracking): Essentials at $1,497 (90-day action plan), Professional at $2,997 (+ strategy calls and implementation support), and Enterprise at $5,997 (+ portfolio analysis, AI automation audit, quarterly sessions, direct J. Massey access). One-time or per-engagement revenue.
3. Affiliate Revenue: CashFlowDiary participates in affiliate programs for STR software tools (Hospitable, PriceLabs, Lodgify), real estate education platforms, business software, and Amazon Associates. Commissions are earned when users purchase through affiliate links at no additional cost to the buyer. Revenue is entirely referral-based and variable.

Pricing tiers

Go-to-market motion3 records

Distribution channels5 records

Marketing channels9 records

Core offering

CashFlowDiary is an online education, membership, and consulting platform that teaches individual entrepreneurs how to build profitable short-term rental (STR) businesses — including rental arbitrage — using AI-powered automation and documented operating systems. The core offering combines recurring membership subscriptions (Free Journey, $197/mo Operator, $997/mo Elite) with one-time consulting engagements delivered through the SOAR framework ($1,497-$5,997), supported by a library of pre-built STR workflow kits, free financial calculators, and a 237+ episode podcast.

Product overview

CashFlowDiary is an STR education platform offering a multi-tier product ecosystem: free entry through the Journey membership (podcast, newsletter, community), paid Operator ($197/mo) and Elite ($997/mo) tiers for deeper access to AI tools and private deal networks, and consulting engagements via the SOAR framework ($1,497-$5,997). The platform provides free financial calculators (Airbnb Income Calculator, Arbitrage Calculator, STR Investment Calculator, Arbitrage vs. Buy tool, Cleaning Fee Calculator) as lead-generation tools, complemented by premium STR Kits ($97-$297 each) as workflow bundles. The company also offers free diagnostic calls and Elite-tier consulting paths focused on AI-powered STR automation.

Differentiator

Problem solved

Functional benefit

Brands

• SOAR Consulting: Custom consulting service using the SOAR framework (Situation, Opportunity, Action, Results) for personalized 90-day action plans for STR businesses.

Products and services

• Journey Membership Free membership tier serving as CashFlowDiary's entry-level offering. Provides weekly podcast access, a community newsletter, and access to public forums for aspiring short-term rental operators. Designed to convert users into paid Operator or Elite memberships or into SOAR Consulting engagements.
• Operator Membership $197/month paid membership for active or launching STR operators. Includes full community access, the AI Tool Library, monthly live Q&As with J. Massey, and the Resource Vault (checklists, scripts, contracts, financial models).
• Elite Membership $997/month top-tier subscription membership (application required) for scaling STR operators. Includes everything in Operator plus 1:1 STR consulting sessions, access to the Private Deal Network (deal flow, high-yield partnerships, co-hosting opportunities), and VIP Mastermind Retreats.
• SOAR Consulting One-time consulting service for STR operators built on the proprietary SOAR 57-question diagnostic, producing a personalized 90-day KNOW-DO-TRACK action plan with 90+ ranked opportunities. Available in three tiers: Essentials ($1,497), Professional ($2,997, adds strategy calls and 90-day implementation support), and Enterprise ($5,997, adds full portfolio analysis, AI automation audit, quarterly strategy sessions, and direct J. Massey private advisory access).
• STR Kits 60+ pre-built digital workflow bundles covering 10 distinct STR business phases (Foundation & Setup, Market Research, Property Preparation, Listing Optimization, Pricing & Revenue, Guest Experience, Operations & Automation, Marketing & Growth, Financial Management, Scaling & Portfolio). Each kit contains workflow maps, SOPs, triggers, checklists, and quick-start guides, priced $97-$297 per kit.
• Airbnb Income Calculator Free interactive calculator that projects monthly and annual STR revenue, net profit, and RevPAR based on user-inputted nightly rates, occupancy, and operating costs. Used as a top-of-funnel lead magnet to capture email signups for the newsletter and community.
• Airbnb Arbitrage Calculator Free interactive calculator that determines monthly cash flow, cash-on-cash return, and breakeven occupancy on leased STR units. Used by rental arbitrage operators to validate deals before signing leases with landlords.
• STR Investment Calculator Free interactive calculator for analyzing STR property purchases, showing cap rate, cash-on-cash return, and breakeven occupancy for prospective buyers.
• Arbitrage vs. Buy Decision Tool Free interactive decision tool that recommends whether to lease (arbitrage) or buy a property based on the user's capital, goals, financing availability, speed-to-launch, and ownership preferences.
• Cleaning & Co-Host Fee Calculator Free interactive calculator for determining optimal cleaning fees to cover turnover costs and calculating the impact of co-host fee structures on net STR revenue.
• STR Systems Diagnostic Call Free 30-minute consultation call designed to identify the single biggest operational systems leak in an STR business and provide one concrete next step. No sales pressure; functions as a bottom-of-funnel conversion mechanism for SOAR Consulting and paid memberships.
• AI STR Strategy Diagnostic Call Free 25-minute diagnostic call that maps where AI can create the fastest leverage in an STR portfolio, identifies hidden bottlenecks, and provides an AI reality check. Functions as a specialized funnel for the AI-Powered STR Ops consulting path and SOAR Enterprise tier.
• CashFlowDiary Podcast Long-running podcast with 237+ episodes featuring real conversations about short-term rental strategies, real deals, and operator success stories. Available free on major podcast platforms; serves as both a brand-building marketing channel and a standalone content product that drives listeners to cashflowdiary.com.
• Cashflow Diary Direct Newsletter Substack-delivered newsletter 'Cashflow Diary Direct' with 18,000+ subscribers, delivering actionable short-term rental strategies, AI automation tools, and proven templates twice weekly. Converts subscribers into paid memberships and consulting clients through embedded calls to action.
• STR Launch Checklist Free 47-step checklist guiding aspiring STR operators from property acquisition through to their first profitable STR booking. Available via newsletter subscription as an entry-level lead magnet for the CashFlowDiary community.

Quantifiable outcome

• Operators can grow from $0 to $8,000/month in 90 days using CashFlowDiary's framework
• +6 more outcomes

Named customers7 records

Segments4 records

Ideal customer profiles4 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature5 records

Scale indicators8 records

Recent moves6 records

Expansion highlights5 records

Others

• AirDNA: Short-term rental market data and analytics provider whose data is cited in CashFlowDiary's blog content. Comparable as an ecosystem participant providing underlying market intelligence that STR educators and operators rely on.
• Mashvisor: Real estate investment analytics and market data platform for traditional and short-term rental investors. Comparable as an adjacent analytics provider serving overlapping investor and STR operator buyer personas.
• PriceLabs: Dynamic pricing tool for short-term rentals, cited as an affiliate partner of CashFlowDiary. Comparable as an ecosystem pricing tool embedded in CashFlowDiary's recommended STR operator tech stack.
• Hospitable: Short-term rental automation and guest communication platform that is an affiliate partner of CashFlowDiary. Comparable as an ecosystem tool referenced and recommended to CashFlowDiary's automation-obsessed operator segment.
• Wheelhouse: Short-term rental dynamic pricing and revenue management platform. Comparable as an ecosystem participant providing automation tools that CashFlowDiary's Elite and consulting customers implement.

Broad incumbents

• Roofstock: Single-family rental investment marketplace and education provider. Comparable to CashFlowDiary as a broader real estate investment platform serving aspiring passive investors, but operates as an incumbent marketplace rather than a coaching community.
• Vacasa: Largest US full-service short-term rental management company. Comparable as an incumbent player in the broader STR services space where CashFlowDiary's automation-obsessed operator segment also operates.

Direct peers

• BNB University: Airbnb and short-term rental-focused education brand offering courses and coaching. Comparable to CashFlowDiary as a niche STR education platform that competes for the same aspiring host and scale-seeker personas.
• Fortune Builders: Real estate education and coaching platform offering courses, mentoring programs, and live events. Comparable to CashFlowDiary as a multi-tier coaching business targeting aspiring and scaling real estate entrepreneurs with premium mentoring engagements.
• BiggerPockets: The largest real estate investing education community in the US, offering a podcast, forums, pro membership, and books. Direct comparable to CashFlowDiary because it sells similar self-paced education, a subscription community, and paid tools to the same aspiring and active real estate investor audience.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights6 records

Customer concentration

• LinkedInlinkedin.com/company/cashflow-diary-with-j.-massey

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Cashflow Diary