Why of AI
Why of AI is a Chicago-based AI consulting firm that provides strategy, implementation, and training services to mid-market company leaders on a month-to-month retainer, leveraging third-party AI models and proprietary frameworks such as the AIPB Framework and Four-Pillar Responsible AI Method.
- Company typePrivate
- Founded2017
- HeadquartersChicago, United States
- Headcount1–10
- GTM typeB2B
- OfferingServices
What Why of AI does
Why of AI is a private, boutique AI consulting firm incorporated as Why of AI LLC (also doing business as Expericom) and headquartered in Chicago, Illinois, with a secondary office in Austin, Texas. The firm serves mid-market company leaders who need AI strategy, implementation, and training without recruiting an internal AI team, and it operates across verticals including logistics, private equity, distribution, and staffing. Why of AI was founded in 2017 by Alex Castrounis, a former INDYCAR race strategist and data scientist who previously served as head of data science at Andretti Autosport and is currently a Northwestern Kellogg adjunct faculty member and TEDx speaker.
The company's core offering is a month-to-month advisory retainer that bundles strategy, implementation, and training around one focused priority at a time, with a 30-day cancellation term and a stated minimum commitment of three consecutive months. Services are delivered using established third-party AI platforms rather than proprietary models: large language models from OpenAI and Anthropic, workflow automation tools (Zapier, Make, Pipedream, n8n), no-code environments (Airtable), and Zoom AI for meeting transcription. Why of AI's differentiated IP is methodological: the AIPB Framework, the TCPR (Time, Cost, Performance, Requirements) project estimation model, and a Four-Pillar Responsible AI Method aligned with NIST AI RMF, ISO/IEC 42001, SOC 2, and ISO/IEC 27001.
Revenue is generated primarily through monthly recurring retainers, with credits-based add-ons for parallel work and hourly billing for out-of-scope services, professional-services engagements for workshops, training, due diligence, and AI solution development. The go-to-market is consultative and sales-led: prospective clients book a free strategy call through the website, then convert to retainer engagements. Acquisition relies on the founder's content engine — the published O'Reilly book 'AI for People and Business,' TEDx talk, SXSW and other speaking engagements, blog, and newsletter — rather than paid advertising or channel partners. The firm is founder-financed with no disclosed external funding and operates with a headcount in the 1-10 range.
Why of AI firmographics
Firmographics- Name
- Why of AI
- Legal name
- Why of AI LLC
- Website
- https://whyofai.com
- Company type
- Private
- Founded year
- 2017
- Operating status
- Operating
- Headcount range
- 1–10 employees
- Short description
- Why of AI is a Chicago-based AI consulting firm that provides strategy, implementation, and training services to mid-market company leaders on a month-to-month retainer, leveraging third-party AI models and proprietary frameworks such as the AIPB Framework and Four-Pillar Responsible AI Method.
- Ownership category
- akta.pro rank
Where Why of AI is headquartered
LocationHeadquarters
- HQ city
- Chicago
- HQ country
- United States
- HQ region
- North America
Offices2 records
Markets served
Why of AI business model
Business model- GTM type
- B2B
- Offering type
- Services
- Cost components
- Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure, Others
Revenue model
- Monthly Retainer (AI Consulting): Recurring monthly retainer providing AI strategy, implementation, and training services. Clients pay one monthly rate for a focused priority, with the option to add a second priority for parallel capacity. No long-term contracts — month-to-month with 30-day notice. Minimum commitment of three consecutive months. Additional monthly hours billed at the same hourly rate as the retainer. This is the primary revenue stream.
- Credits-Based Retainer: Monthly retainer fee for a fixed number of monthly credits providing access to delivery capacity. Add-on credits available for additional work beyond included credits. Credits expire at the end of each monthly billing cycle and do not rollover.
- Hourly Work / Out-of-Scope Services: Services outside the agreed retainer scope are billed at Why of AI's then-current hourly rates, payable in advance. Also available for non-retainer clients seeking AI consulting on an hourly basis.
- Additional Services (Workshops, Training, Due Diligence): Additional services beyond standard retainer scope, including workshops, training, research, due diligence, and design/development/testing/delivery of AI-related solutions such as automations, workflows, agents, models, or tools. Billed monthly in arrears based on usage.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Subscription | Monthly | Standard Monthly Retainer |
| Subscription | Monthly | Credits-Based Retainer |
| Other | Pay-as-you-go | Hourly / Out-of-Scope Work |
Go-to-market motion2 records
Distribution channels2 records
Marketing channels7 records
Why of AI product offering
Product offeringCore offering
Why of AI is an AI consulting firm that delivers strategy, implementation, and training for mid-market companies on a month-to-month retainer. Engagements cover AI readiness and risk assessments, roadmapping, tool selection, and the build-out of AI assistants, prompt workflows, integrated agents, knowledge systems including RAG, and workflow automations inside the client's environment, paired with team training and responsible AI governance. Clients pay one predictable monthly rate for one focused priority at a time with no long-term contracts, and retain ownership of all deliverables.
Product overview
Why of AI is an AI consulting firm offering a unified monthly retainer service for mid-market companies. The core offering combines strategy, implementation, and training delivered by practitioners. Strategy services include readiness assessments, roadmapping, and vendor evaluation. Implementation encompasses AI assistants, prompt workflows, AI integrations, connected agents, knowledge systems (including RAG), and automation built in client environments. Training covers AI fluency, tool-specific enablement, and capability building. Additional offerings include responsible AI guidance aligned with NIST AI RMF and ISO/IEC 42001, the AIPB Framework (a downloadable strategic framework), the book 'AI for People and Business' by founder Alex Castrounis, and educational content via newsletter and blog. The company operates on a month-to-month model with no long-term contracts; clients retain ownership of all deliverables.
Differentiator
Problem solved
Functional benefit
Products and services
- AI Consulting Retainer A monthly retainer that bundles AI strategy, implementation, and training for a single mid-market client, focused on one priority at a time. Includes access to a fractional AI team for assessment, roadmapping, build-vs-buy analysis, tool selection, AI assistants, prompt workflows, integrations, connected agents, knowledge systems with RAG, light serverless functions, and team training. Sold month-to-month with 30-day notice and a three-month minimum, with add-on credits for parallel work.
- AI for People and Business (Book) A standalone book authored by Why of AI founder Alex Castrounis and published by O'Reilly Media, providing a framework guide for business leaders on developing and executing AI strategy. Listed as a former Amazon #1 New Release and recognized by BookAuthority as one of the best artificial intelligence books of all time.
Quantifiable outcome
- Most teams have a usable deliverable within the first month
- +2 more outcomes
Companies that use Why of AI
Customer profileNamed customers4 records
Segments3 records
Ideal customer profiles2 records
Why of AI technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
AI capability5 records
Feature4 records
Why of AI partnerships and signals
Strategic signalPartnerships
One partnership is on record.
- GoogleminorUsed for ads, analytics, and optimization. Google serves ads based on user visits to the website and other sites. Users can opt out of personalized advertising via Ads Settings.
Scale indicators2 records
Recent moves6 records
Expansion highlights7 records
Why of AI competitors and assessment
Company assessmentBroad incumbents
- Credera: Credera is a global technology and AI consulting firm that emphasizes strategy, implementation, and capability building across data, AI, and cloud. Its mid-market and enterprise client mix and integrated strategy-plus-execution model make it a relevant comparator for Why of AI's retainer offerings.
- McKinsey & Company (QuantumBlack): McKinsey's QuantumBlack is the firm's AI and analytics arm, delivering AI strategy and implementation to large enterprises and PE portfolios. It is a relevant comparator for Why of AI's responsible-AI and strategy advisory work, particularly when PE clients seek scaled alternatives.
- Deloitte (AI Institute / Strategy & Analytics): Deloitte's AI practice delivers responsible AI, governance, and implementation services aligned with NIST and ISO standards to enterprises and regulated industries. It is a relevant incumbent competitor for governance-heavy AI mandates that Why of AI targets, with a global delivery footprint.
- Bain & Company: Bain is a top-tier global management consultancy with a strong AI and advanced analytics practice serving Fortune 500 and PE clients. It competes for the same enterprise and PE-backed AI strategy mandates as Why of AI, with substantially greater resources and a higher price point.
- Slalom: Slalom is a large, mid-market-focused technology and AI consulting firm with a strong national presence and established AI/ML practices. It is comparable as a competitor for mid-market AI strategy and implementation mandates, though it operates at significantly greater scale and offers a broader portfolio of services than Why of AI's boutique model.
- Boston Consulting Group (BCG GAMMA): BCG GAMMA is BCG's data science and AI consulting practice, combining AI strategy, use-case prioritization, and implementation for global clients. It is comparable on AI strategy framing and PE portfolio work, though serving materially larger and higher-budget clients than Why of AI.
- West Monroe Partners: West Monroe is a mid-market-focused management and technology consulting firm with deep AI, data, and analytics practices serving industries including logistics, PE, and distribution. It is directly comparable on target buyer and service mix, though at materially larger scale than Why of AI.
- Accenture (Accenture AI): Accenture AI delivers end-to-end AI strategy, implementation, and managed services at global scale, including mid-market and PE engagements. It represents the largest-scale comparator for Why of AI's strategy-plus-implementation retainer and competes for the same Fortune 1000 / mid-market AI mandates.
Direct peers
- Tesseract: Tesseract is a boutique AI advisory and implementation firm helping organizations identify and execute high-impact AI use cases, with a fractional/expert-team model similar to Why of AI. It is a close direct competitor for mid-market AI strategy and deployment retainers.
- Pandata: Pandata is a boutique AI consulting firm that designs and implements AI solutions for mid-market and enterprise clients, with emphasis on responsible AI and human-centered design. It is highly comparable in size, mid-market focus, and AI-strategy-plus-implementation offering to Why of AI.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat3 records
Key risks7 records
Key highlights7 records
Customer concentration
Why of AI social profiles
Digital presenceWhy of AI compliance and trust
Trust signalCompliance2 records
Why of AI financial estimates
Financial estimateRevenue estimate
Valuation estimate
Why of AI leadership team
Management profileNumber of profiles
Profiles2 records
Why of AI funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Why of AI M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Why of AI
What does Why of AI do?
Why of AI is an AI consulting firm that delivers strategy, implementation, and training for mid-market companies on a month-to-month retainer. Engagements cover AI readiness and risk assessments, roadmapping, tool selection, and the build-out of AI assistants, prompt workflows, integrated agents, knowledge systems including RAG, and workflow automations inside the client's environment, paired with team training and responsible AI governance. Clients pay one predictable monthly rate for one focused priority at a time with no long-term contracts, and retain ownership of all deliverables.
Is Why of AI a public or private company?
Why of AI is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was Why of AI founded?
Why of AI was founded in 2017. It employs 1 to 10 people.
Where is Why of AI based?
Why of AI is headquartered in Chicago, United States, in the North America region.
How does Why of AI make money?
Four revenue lines are on record. Monthly Retainer (AI Consulting) is the primary driver. The others are credits-Based Retainer, hourly Work / Out-of-Scope Services and additional Services (Workshops, Training, Due Diligence).
Who are Why of AI's main competitors?
Broad incumbents on record are Credera, McKinsey & Company (QuantumBlack), Deloitte (AI Institute / Strategy & Analytics), Bain & Company, Slalom, Boston Consulting Group (BCG GAMMA), West Monroe Partners and Accenture (Accenture AI). Direct peers are Tesseract and Pandata.
Does Why of AI have an API?
No public API is recorded for Why of AI.