Financial clarity. Operational freedom. Powered by expertise and AI.
Your expertise deserves a system that works as hard as you do.
The Waymaker System gives contractors, property investors, and independent professionals the financial tools, strategic guidance, and AI-powered automation to take full control of their business — and keep more of what they earn.
Qualified Accountant
ERP Implementation Specialist
Finance Business Analyst
AI Automation Consultant
Outside IR35 Contractor — 10+Years
Where do you want to start?
Find the tools and guidance built for your specific situation.
I'm a Contractor
PAIN: Working outside IR35 through a limited company but not certain your contract and working practices are watertight? Losing more than you need to on tax?
SOLUTION: From IR35 audits and expense tracking to limited company tax optimisation and AI-powered admin — we've built the toolkit.
I Invest in Property
PAIN: Building a portfolio but unclear on limited company structure, Section 24, or how to manage your properties without drowning in admin?
SOLUTION: Tax guides, portfolio tools, and AI automations that make managing your properties as efficient as your best investment decision.
I'm Self-Employed
PAIN: Running a consulting or service business but your finances feel chaotic, your admin takes too long, and you're not sure you're paying the right amount of tax?
SOLUTION: Financial guides, business tools, and AI-powered automations that free you up to do the work only you can do.
I Want to Automate
PAIN: Spending hours on invoicing, chasing payments, updating spreadsheets, onboarding clients, or managing repetitive tasks that don't need a human?
SOLUTION: Custom AI automations built for your specific workflow. We design, build, and implement — you reclaim the time.
The tools every contractor should have.
Built by a qualified accountant. Written for the way you actually work.
IR35 Checklist & Expense Tracker
A 20-point contract review, 15-point working practices audit, IR35 scorecard, and fully-built limited company expense tracker — everything you need to assess, document, and manage your outside IR35 position.
Price: £37
★ Most Popular
The UK Contractor's Financial Playbook
The definitive 120-page guide to tax efficiency, IR35 protection, cash flow management, rate strategy, and long-term financial planning — written by a qualified accountant with 10+ years of outside IR35 contracting experience.
Price: £127
How to Run Your Limited Company
From incorporation to dividend strategy — a step-by-step guide covering payroll, VAT, Corporation Tax, IR35, and allowable expenses. Written for IT and finance contractors who want to run their company properly.
Price: £77
Stop doing manually what AI can do automatically.
We design and implement custom AI automations for contractors, property investors, and independent professionals. From invoice generation and expense categorisation to tenant communication workflows and client onboarding sequences — we build the system, connect the tools, and hand you back the hours.
For contractors:
→ Automated IR35 documentation and contract tracking
→ Expense categorisation and tax reserve calculations
→ Invoice generation and payment chasing
For property investors:
→ Automated rent reminders and arrears escalation
→ Maintenance request tracking and contractor coordination
→ Portfolio performance reporting
For independent professionals:
→ Client onboarding sequences and proposal generation
→ Meeting notes to action items pipelines
→ CRM updates and follow-up automations
Dapo Olatunji
Founder, The Waymaker System
CREDENTIALS:
✦ ACCA Qualified Accountant
✦ Finance Business Analyst and Functional Consultant - ERP and ETRM Implementations
✦ SAP | Openlink Endur | Microsoft Dynamics 365
✦ Outside IR35 Contractor — 10+ years
✦ AI Automation Consultant
Built by someone who has been exactly where you are.
I created The Waymaker System because I couldn't find a single resource that spoke directly to contractors and small business owners like me — people with serious financial expertise who still found contracting and running a small business unnecessarily complex, risky, and expensive.
Everything I build is written from the inside. Not by a blogger who has read about IR35, but by a qualified accountant who has sat across from HMRC guidance, reviewed hundreds of contract clauses, structured my own finances and business processes efficiently for over a decade — and more recently, built AI automations that have transformed how I manage the admin side of my business.
The Waymaker System is the toolkit I wish had existed when I started. Now it exists for you.
What contractors are saying.
A 20-point contract review, 15-point working practices audit, IR35 scorecard, and fully-built limited company expense tracker — everything you need to assess, document, and manage your outside IR35 position.
Liam — SAP S/4HANA Contractor, London
The dividend and pension sections of the Financial Playbook alone saved me more than the guide cost. I've been contracting for six years and I still learned things I didn't know.
Amy — D365 Contractor, London
The AI automation they built for my invoice and expense workflow has saved me four hours a week. For a tradesman not having to spend every evening raising invoices, that's money back in my pocket.
Adam — Small Business Owner, London
Trusted by professionals associated with:
CIMA
ICAEW
ACCA
ContractorUK
IPSE
FREE DOWNLOAD
Download the free 5-point IR35 Quick Check — takes 15 minutes and covers the five most common contract red flags HMRC looks for first.
Is your IR35 position actually watertight?
✅ The 5 contract clauses HMRC examines first
✅ 3 working practice red flags that override a perfect contract
✅ A simple pass/fail scoring guide
✅ What to do if you score poorly
From the Waymaker blog.
Plain-English guides on contractor finance, IR35, AI automation, and the ERP market — written by a qualified accountant.
IR35
Inside vs Outside IR35: What's the Real Financial Difference?
If you're on £600/day, the gap between inside and outside IR35 can exceed £20,000 per year. Here's the full breakdown with worked examples.
8 min read
Limited Company
The Optimal Director Salary for 2026/27 — And Why Most Contractors Get This Wrong
Most contractors set the wrong salary level. A qualified accountant explains the correct £9,100 threshold and why going higher costs you money.
7 min read
AI Automation
Tasks Every Contractor Should Automate in 2026
From invoice generation to expense categorisation — these are the admin tasks eating your time that AI can handle in seconds.
6 min read