Raffle Mastery
The Nonprofit Fundraising Guide Written By The People Who Built The Industry.
US-Based Support Team
Pioneered Online Raffles (2005)
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Changed How Nonprofits
Run Raffles.
We wrote Raffle Mastery because we’ve heard every disaster — the winner whose ticket got eaten by the office shredder, the group that forgot to secure the prize before selling 400 tickets, the team that called us at 4:59 PM the day before their drawing. Every horror story in this book is real. And every lesson is there so you can skip them entirely.
This isn’t a guide. It’s a 120-page book built from two decades of real calls, real fundraisers, and real wins — from small PTAs raising a few hundred dollars to organizations clearing $300,000 on a single Queen of Hearts progressive jackpot.
Planning, prizes, legal compliance, drawing day, software evaluation, and everything in between.
The chapter that’ll keep your organization out of trouble. “We didn’t know” is not a defense.
Run it against any vendor — including us. We’re comfortable with the comparison.
The calls we’ve taken. The disasters we’ve helped navigate. The lessons that stick.
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We Wrote the Book Because We’ve Heard Every Disaster.
We have a phone. And yes — we actually answer it. For two decades, our team has taken calls from nonprofit organizers in every stage of raffle chaos. The winner whose ticket got eaten by the office shredder. The group that forgot to secure the prize before selling 400 tickets.
Raffle Mastery exists because behind every one of these calls was a volunteer who cared deeply about their cause and just needed a better roadmap. The horror stories aren’t in the book to entertain you — they’re in there so you can skip them entirely.
Live Call from the Raffle Hotline
“Hey, we launched our raffle but nobody knows who has access to the money. We have Square… or Stripe… maybe? Mary had it and she quit. How do we get the money?”
💡 Lesson: Document everything. Every raffle, every year. Whoever set up the account, whoever has the login — put it in writing, in a shared folder, with actual people attached to it. This call happens more than you’d think.
Years pioneering online raffle technology
Single jackpot raised by one nonprofit on our platform
Raffle formats supported natively — not as workarounds
%
US-based support team. Real people. Real hours.
Nine chapters. No fluff. Just the stuff that actually helps.
The content structure matters because the page should reassure visitors that this is a complete playbook, not a bait-and-switch lead magnet. Each chapter should feel like a reason to download, share, and keep reading.
Setting the Stage for Success
Practical advice built from real raffles, real supporter behavior, and real operational headaches.
Choosing the Right Raffle Type
Practical advice built from real raffles, real supporter behavior, and real operational headaches.
Selecting Prizes That Sell Tickets
Practical advice built from real raffles, real supporter behavior, and real operational headaches.
Building Anticipation and Buzz
Practical advice built from real raffles, real supporter behavior, and real operational headaches.
Maximizing Ticket Sales
Practical advice built from real raffles, real supporter behavior, and real operational headaches.
Staying Legal and Fair
Practical advice built from real raffles, real supporter behavior, and real operational headaches.
Drawing and Announcing Winners
Practical advice built from real raffles, real supporter behavior, and real operational headaches.
Post-Raffle Follow-Up
Practical advice built from real raffles, real supporter behavior, and real operational headaches.
Choosing the Right Software Partner
Practical advice built from real raffles, real supporter behavior, and real operational headaches.
A Quick Word About “Free” Fundraising Platforms.
The book covers this in detail. But it’s worth saying plainly here too. Several platforms will tell you their software is free for nonprofits. What they won’t show you — until your supporter is already at checkout — is a very different story.
⚠️ The Hidden Cost
What “Free” Platforms Don’t Tell You
Several platforms present a 17%–29% “tip” prompt at checkout, designed to cover their costs. It’s labeled optional. It doesn’t feel optional. And every attempt to opt out is met with friction designed to keep the guilt alive.
According to well-documented e-commerce data, somewhere between 30%–40% of buyers will close the page rather than deal with an unexpected guilt charge at checkout. That’s not a rounding error. That’s a third of your supporters walking away.
✓ The Chance2Win Difference
Transparent Pricing. No Surprises.
Chance2Win uses a flat, transparent fee structure for nonprofits. Your supporters see the same price at checkout that they saw when they clicked Buy. No tip prompts. No guilt. No surprises.
We support Stripe, Square, and Authorize.net — because nonprofits shouldn’t have to change their payment processor to use our software. Every other raffle platform in the market runs on Stripe. Full stop.
Written for the People Who Actually Run Fundraisers
Not the board. Not the executive director who shows up for the drawing. The volunteers. The organizers. The person managing the spreadsheet, updating the page, chasing prize donors — and holding down a regular job at the same time.
First-time online raffle organizers
Not sure where to start? Chapter 1 covers goal-setting, team structure, timelines, and budget. That’s exactly where to begin.
Organizations exploring specialty formats
Thinking about a basket raffle, Queen of Hearts, or ball drop? Chapter 2 maps out every format and when to use it.
Teams building a long-term supporter base
Not just selling tickets once and disappearing. If your goal is real community fundraising, this book speaks your language.
Annual raffles that need a better system
If you’ve been doing it for years, you’ll still find things in here worth stealing. Guaranteed.
Nonprofits evaluating their current platform
Chapter 9 includes a checklist you can run against any vendor — including us. We’re comfortable with that comparison.
Anyone who wants to raise more with less chaos
PTAs, churches, sports leagues, veterans groups, animal shelters, school foundations. If your cause matters, your fundraiser should work.
Why Nonprofits Trust the Team Behind This Book.
Most fundraising advice is written by consultants who studied fundraising. This book was written by the people who answered the phone when your fundraiser was on fire. Here’s what makes us different.
We Were First
Chance2Win has been building online raffle solutions for nearly 20 years. We were here before the first iPhone. Before “the cloud” was a thing people said in meetings. Before any of the names you’ve seen in Google ads were even incorporated. That’s not a brag — it’s context.
We Do Things Others Simply Don't
Every other raffle platform runs on Stripe. We support Stripe, Square, and Authorize.net. We’re also the only platform that handles every major raffle type natively — basket raffles, Queen of Hearts, duck races, ball drops, 50/50, tricky trays. All built in. With proper ticket number logic. Including refund handling.
We Answer the Phone
Our US-based support team is available during business hours. Not a chatbot. Not a ticket system with a 72-hour SLA. A real person who knows what a Queen of Hearts progressive jackpot is and can walk you through it before your event goes live. Those conversations are also how we build the platform.
When we built the first online raffle website, the goal wasn’t to build a platform. It was to solve a problem that apparently nobody else wanted to solve: how do you give someone a digital raffle ticket that actually feels like a raffle ticket? That question led to two decades of conversations with nonprofit teams across the country. The lessons in Raffle Mastery didn’t come from research. They came from those conversations — and from answering the phone every time things went sideways.
— The Chance2Win Team | chance2win.org
“We’ll answer.”
Before You Download
Is the book really free?
Yes. The ebook is completely free. Now, if you really want to hand over $19.95 for a physical copy you can hold in your hands, we certainly won't stop you. But since we genuinely like helping nonprofits raise more money, we made the digital version free. You'll enter your email so we know where to send it — which also adds you to the Chance2Win newsletter. A few emails a year, fundraising ideas and platform updates, and you can unsubscribe any time with zero hard feelings. We don't spam. We don't sell your info. That's it.
Do I need to already use Chance2Win to benefit from the book?
Nope. The book is useful for any nonprofit running any raffle on any platform. Chapter 9 is the one that gets into platform evaluation — and it includes a checklist you can use on us too. We're comfortable with that comparison. You can also see how we compare directly to other platforms on our website.
We've never run an online raffle before. Is this too advanced?
It starts from the beginning and works forward. Chapter 1 covers goal-setting, team structure, timelines, and budget. If you've never run a raffle before, that's exactly where to start. If you've been doing it for years, you'll probably still find things in here worth stealing. The book was built from real calls — some of which came from organizations that had been running raffles for a decade and were still making fixable mistakes.
What raffle types does Chance2Win actually support?
Traditional raffles, 50/50, basket raffles and tricky trays (with per-basket ticket assignment), Queen of Hearts progressive jackpots, duck races, ball drops — all with correct ticket numbering, refund handling, and drawing tools built in. Not workarounds. Not "you can kind of set it up this way." Native, purpose-built support for each format.
How will I receive the book after signing up?
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