What Amazing If does

Amazing If Limited is a UK-based private career development company, founded in 2013 and operating under the consumer-facing 'Squiggly Careers' brand. The company is registered in England and Wales (Company No. 08719578) with a registered office at 7 Bell Yard, London. It serves working professionals, corporate organizations, and disadvantaged university students through a portfolio centered on the Squiggly Careers philosophy of non-linear career development.

The core product surface comprises the Squiggly Careers Podcast (500+ episodes, 5M+ listeners, 700+ five-star reviews), a weekly newsletter reaching 1M+ subscribers, the published book 'Learn Like a Lobster', and supporting resources such as PodSheets and free career tools. Technology components include two AI features: the Learn Like a Lobster Profiler (a personalized assessment that generates customized reports from user responses) and Say The Hard Thing GPT (a conversational tool for difficult workplace conversations, routed through OpenRouter with Zero Data Retention endpoints). Squiggly Skills Sprints further integrate AI-driven self-assessment prompts into structured learning programs.

The business model combines freemium content and tools (podcast, newsletter, free downloads) with paid monetization through one-time book sales and recurring/quote-based corporate offerings (Squiggly Careers Company Toolkit, workshops). Corporate clients include Sky, Microsoft, BBC, Levi's, Capgemini, easyJet, British Airways, Cancer Research UK, World Food Programme, and Virgin. A three-year partnership with social mobility charity upReach delivers the Squiggly Career Students program to 32 university students from low-income backgrounds. The company operates with 1–10 employees and generates revenue primarily through direct consumer book sales and direct enterprise engagement, with no publicly disclosed pricing or revenue figures.

Name

Amazing If

Legal name

Amazing If Limited

Website

https://amazingif.com

Company type

Private

Founded year

2013

Operating status

Operating

Headcount range

1–10 employees

Short description

Amazing If is a UK-based career development company operating the 'Squiggly Careers' brand, serving working professionals, corporate organizations, and disadvantaged university students through a podcast (5M+ listeners), newsletter (1M+ subscribers), books, AI-powered tools, and corporate training workshops.

Ownership category

akta.pro rank

Product category

Professional Development & Career Coaching

NAICS

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

SIC

Miscellaneous Publishing (2741), Services-Management Consulting Services (8742)

akta.pro primary industry

Career Exploration, Interest/Skills Assessment & Pathway Planning (EDAFAMAK)

akta.pro secondary industries

Job Search Strategy & Application Skills (EDAAAKAC), Career Exploration & Industry Exposure (Guest Speakers, Company Visits) (EDAMAHAJ), Leadership, Management & Teamwork for Business (EDAMAHAI)

Keywords

• Career development
• Professional training
• Workplace coaching
• Learning resources
• Career guidance

Headquarters

HQ city

London

HQ country

United Kingdom

HQ region

Europe

Offices1 record

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

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

Revenue model

1. Books and Publications: Sale of books including Learn Like a Lobster and related personalized items like library cards
2. Corporate Training and Toolkits: Squiggly Careers Company Toolkit and workshops sold to organizations for workplace development programs
3. Free Content and Tools: Free tools, podcast content, and newsletter building audience for potential monetization through books and corporate partnerships

Pricing tiers

Go-to-market motion3 records

Distribution channels4 records

Marketing channels6 records

Core offering

Amazing If is a career development consultancy operating the "Squiggly Careers" brand. It sells podcasts, books, AI-powered self-coaching tools, free digital career tools, Skills Sprints, and a Squiggly Careers Company Toolkit to help individuals navigate modern careers and to help employers train their people.

Product overview

Amazing If is a career development company offering a portfolio of products centered around the 'Squiggly Careers' philosophy. The core offering is the Squiggly Careers Podcast (500+ episodes, 5+ million listeners), supplemented by the published book 'Learn Like a Lobster' with an accompanying AI-powered Profiler. The product suite includes free tools (career tools, Skills Sprints, newsletter), organizational offerings (Company Toolkit, Squiggle & Stay), and community programs (Squiggly Career Students with upReach). AI capabilities include the Say The Hard Thing GPT for difficult conversations and AI-enhanced learning experiences in Skills Sprints.

Differentiator

Problem solved

Functional benefit

Brands

• Squiggly Career Students: A three-year programme supporting 32 university students from low-income backgrounds to start and succeed at work, run in partnership with social mobility charity upReach.

Products and services

• Squiggly Careers Podcast

Quantifiable outcome

• 500+ episodes and 5M+ listeners demonstrate strong content reach
• +1 more outcomes

Named customers10 records

Segments3 records

Ideal customer profiles3 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

AI capability7 records

Feature2 records

Partnerships

One partnership is on record.

• upReachcoreStrategic or Co-development PartnerThree-year partnership with upReach, an award-winning social mobility charity, to support 32 university students from low-income backgrounds through the Squiggly Career Students program. The program combines Squiggly Careers' practical tools with upReach's tailored support to help students build skills, confidence, and networks. Students receive workshops, one-to-one coaching, mentoring, career support, and paid work experience opportunities.

Scale indicators5 records

Recent moves6 records

Expansion highlights6 records

Others

• Class Central: Aggregator and review platform for online professional courses and MOOCs. Comparable ecosystem participant as a discovery/curation layer for working professionals evaluating career development learning options.

Emerging players

• CoachAccountable: Software platform for individual and team coaches to manage coaching engagements, sessions and content. Comparable in serving the practitioner-led career coaching/development market with AI and content-rich workflows rather than enterprise LMS-scale.

Broad incumbents

• Coursera: Global online learning marketplace offering professional development courses, certificates and degree programs. Comparable in monetizing career progression content for individuals and corporate learners, though Coursera leans academic/certified while Amazing If is practitioner-led and content-first.
• MasterClass: Premium streaming platform for expert-led professional and creative courses. Comparable business model of monetizing expert-led video content at scale, though MasterClass emphasizes celebrity instructors across many verticals where Amazing If is a focused niche brand.
• Skillsoft: Enterprise L&D platform offering leadership, business and technology training content plus an AI-powered coach. Directly comparable on the corporate toolkit/workshops side targeting enterprise L&D buyers, though Skillsoft is platform/SaaS-led and far larger.
• LinkedIn Learning: LinkedIn's professional learning platform with a vast library of business, tech and creative courses. Directly comparable as a distribution-heavy career/professional development content business serving both individuals and enterprise L&D buyers, though much larger and broader in scope than Amazing If's niche 'squiggly careers' focus.

Direct peers

• Mind Tools: Established career and management skills platform offering toolkits, articles and resources for professionals. Closest direct analogue to Amazing If's combined toolkit + podcast + newsletter offering for individual learners and corporate L&D, with similar founder-driven thought leadership roots.
• The School of Life: Career and emotional-skills education brand offering books, video, podcast and workshops. Highly comparable in combining philosophy-driven content, published books and B2C/B2B programs around navigating work and life.
• Blinkist: Subscription service distilling non-fiction and business books into short summaries for professional learners. Comparable in converting published ideas into bite-sized, mobile-first professional development content with both consumer and B2B offerings.

Regional players

• HBR / Harvard Business Publishing Corporate Learning: Harvard Business Publishing's corporate learning arm delivers leadership and career development content and is a direct adjacent channel for Amazing If, whose co-founders contribute HBR articles. Comparable as a premium thought-leadership and corporate L&D content brand.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights7 records

Customer concentration

• YouTubeyoutube.com/c/SquigglyCareers
• Instagraminstagram.com/amazingif
• Xx.com/amazing_if

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 Amazing If