Donna O'Toole: How to Win Business Awards (Without Getting Scammed)

Donna O’Toole is an award-winning entrepreneur, bestselling author of “Win,” and founder of August Recognition, a global awards agency. In this episode, Donna joins Joe Gregory to break down how she turned her expertise into a book — and how that book became the foundation for a training program, an accelerator, and now an AI-powered platform called AwardsApp.

Donna shares the real strategy behind winning business awards: how to plan a 12-month award roadmap, spot scam and “link farming” award schemes, avoid disqualification from AI-generated entries, and use award wins as a tool for brand authority, recruitment, and growth. She also opens up about writing her book “Win,” why she gave away thousands of copies instead of selling them, and how consolidating her knowledge into a book unlocked opportunities she never expected — including speaking gigs, partnerships, and building her own SaaS product.

If you’re an entrepreneur, marketer, or business leader curious about using awards, books, and personal brand as pillars of authority — this conversation is packed with practical insight.

What You’ll Learn

• Why Donna wrote her book “Win” and how it became her “best business card”
• The real strategic planning that goes into winning credible business awards
• How to spot award scams, phishing schemes, and “link farming”
• Why AI-written award entries get disqualified — and what judges actually look for
• The “Plan, Win, Promote” framework for leveraging awards
• How a book can turn into a training program, an accelerator, and eventually a tech product
• The four pillars of authority: awards, books, publicity, and speaking
• How AwardsApp aims to make finding and entering awards safer and smarter

Timestamps

00:00 – Introduction to Donna O’Toole & August Recognition
00:57 – What drove Donna to write her book “Win”
02:11 – The core problem her book and agency solve
03:51 – Why proper awards take serious preparation
04:37 – Building a strategic plan before entering awards
06:09 – Imposter syndrome around entering awards
07:00 – Where awards fit in a business’s marketing mix
08:44 – Designing the book “Win” and choosing the title
10:00 – Why Donna gives the book away instead of selling it
11:29 – How the book acts as an “undercover ambassador”
13:12 – Pinch-me moments since publishing
14:00 – How the book led to a training program and AwardsApp
14:44 – How writing the book felt (cathartic, not guilty)
17:00 – How writing consolidated her expertise and case studies
18:21 – Recording the audiobook
18:54 – How the book shaped internal team training
21:07 – The four pillars of authority: awards, books, publicity, speaking
24:42 – Warning signs of scam and fake awards
26:21 – Explaining “link farming” and backlink scams
27:34 – Cloned award websites and phishing entries
29:00 – How far in advance to plan for awards (ideally 12 months)
30:24 – The seasonal cycle of business awards
31:39 – Gaps most businesses have in collecting evidence/case studies
33:06 – Introducing AwardsApp and the “Find, Enter, Win” concept
34:20 – Why AI-generated award entries get disqualified
36:17 – How AwardsApp helps you enter the “right race”
36:32 – August Recognition vs. AwardsApp — how the two connect
38:17 – Where to get the book and join the AwardsApp waitlist