The Ultimate Guide to Fundraising Quickly and Painlessly (and without giving away half your profit!)

How to not get fired by your AD in your post-season meeting...

When I first started coaching, I knew nothing.

I thought I knew a lot…But I didn’t.

It was even worse than that though.

I was 23 years old and I inherited a wrestling program with eight kids on the roster, no commitment, a wrestling mat from 1980 (it was 2002 at the time!), singlets from around that same time. It was a sad state of affairs.

My first year was rough.

We had no culture, kids quit (which hurts even more when you’re only starting with eight of them), you could hear crickets in the gym at our matches (if I listened carefully enough, I'm pretty sure I heard them laughing).

Me coaching back in the day.

I also had a rude awakening. I didn’t know nearly as much as I thought I did. It was embarrassing. It was frustrating.

More...

I was young, naive and optimistic, though.

After limping though the finish line that first season - without a single kid qualifying for our Sectionals, I might add - I was down but not out.

So, I did what we all do as coaches when our season ends…I looked towards the future and started planning for my post-season meeting with our AD.

If I’m being completely honest, I was more than a little nervous about how that meeting was gonna go. Here I was as a young coach, having just finished my first season, that in my mind was a total disappointment. I wasn’t exactly sure where I stood with having a job next year, but I did know there were a lot of things I wanted to change and a lot of things I wanted to improve in our program.

I walked into our meeting with a whole laundry list.

“So, how do you think your season went?” he asked me.

Loaded question, I thought.

I gave some quick reply about how I thought we had a lot to improve and I launched into my list:

“Next year we’ll get a new wrestling mat and singlets so help develop a little more pride in our kids and to help get more kids on the team.”

“Next year I’ll implement everything I learn from all the coaching clinics I’ll attend and videos and books I’ll buy this off-season.”

“Next year I’ll put more resources into promoting our matches to get some fans in the seats and some support from the community.”

I paused for a second, trying to read his reaction. He looked at me for a second and then started laughing. I didn’t know if this was a good thing or a bad thing so I just stayed quiet.

“Those are all excellent ideas, Pete, and I support all of them."

This is good, I thought.

“The problem is,” he continued, “that none of that is going to happen. We don’t have money for any of that.”

When the meeting ended, I walked out with a job still, but also another dose of reality. For most of us in high school athletics it’s hard or impossible to really get what we need for our program if we’re relying on always-tightening school budgets.

That meeting was a wake up call for me. That’s when I started looking around at the most successful teams in our area and realized there was another game being played all around me that I wasn’t even aware of.

The teams that seemed to have it all were able to do so because they'd figured out how to raise the money they needed to be successful.

I spent the next 15 years trying to figure it out. We tried everything out there. There were some successes, some failures, and a lot of trial and error, but the main conclusion I was able to come to was that fundraising sucks.

As the years went by, we got better at it though, we refined and incrementally improved the strategies we used. Our system eventually evolved to what it is today. And that system is easy replicable, painless and has yielded us tens of thousands of dollars over the years.

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Implementing these strategies has been one of the best things we have done to really move the needle and improve our program.

While fundraising alone isn’t the single cure-all to the challenges you and your program face, it absolutely is part of the solution to almost any issue you might face.

Need to get more of the “right” kids into your program? Fundraising will give you the resources you need to spread the word about the benefits your program offers kids.

Want more fans in the seats? Fundraising lets you market your program and create exciting events that get fans in the door.

Want to up your coaching game? Fundraising suddenly gives you access to all the books, videos, clinics and courses you need.

Need more equipment? New uniforms? More coaches? A way to travel to that tournament? Fundraising makes all of this possible.

So what’s the problem?

I think we all know the problems with fundraising! It takes too much time. It’s an administrative nightmare. Your staff, kids and parents don’t want to do it either. All the “easy” solutions out there are from companies that take such a big cut of your money, it seems like the profit is never worth the effort!

Here’s the answer.

Fortunately there’s a better way. It’s taken 15 years, a lot of trial and error and a lot of frustration along the way, but we’ve come up with a repeatable system and concrete strategies you can use to bring in the most money with the least amount of time and effort - and not give away half the profits to a fundraising company!

With all the strategies and tactics offered in this guide, there will definitely be several you can use in your specific situation to start bringing in money now!

In fact, this guide was written to be the single best resource on the entire internet to help you reach your fundraising goals with your program.

It will grow and change over time, so if there’s something you feel is confusing, something that’s missing or something that’s working great for you (or not so great!)... PLEASE email me and let me know at pete@winsmarter.com.

I made this Ultimate Guide FREE because I want to impact as many coaches as possible, please help me pay it forward by sharing your thoughts!

Warning: This is not just a magic pill! If you’re the kind of coach who likes reading about strategy and then talking about how you’ll do it later, how the time’s not right for you right now, or how it won’t work for your unique “special snowflake” of a program, then this guide is not for you.

But… if you’re ready to learn the strategies that have worked over and over again for hundreds of programs and TAKE ACTION for your program, I can virtually guarantee you amazing results!

So let’s dig in!

To make things easy for you to follow and implement, this guide is divided up into a few parts:

Part 1: Getting ready to go so you guarantee success

First things first: Let’s look at the numbers

Before we start raising any money, we need to figure out exactly what we want to raise money for and how much it will cost us.

In order to attack our goals, we need to know what our goals are!

Let’s start with an example. Let’s say we need to purchase new uniforms. Let’s first wrap our head around what that will actually cost us.

For argument’s sake, let’s say we want to order 30 sets and we go out to get quotes from whatever vendors we want to work with.

In this example, let’s say our cost including shipping is $2,500.

Now, let’s change our point of view on this whole project before we even get started.

Oftentimes, we limit our ability to come up with solutions by thinking about a problem in only it’s most obvious terms.The question we need to be asking ourselves is not “How can I get new uniforms?”

The real question we need to start thinking about is “Where can I get $2,500?”

For a lot of people, and I know I’m one of those people, by thinking in terms of dollars instead of any other way, a lot more potential ideas start popping up in my head.

So let’s talk about that!

Work smarter, not harder

Hey, our site is called WinSmarter for a reason! As a coach you realize success always requires hard work, but being smart about the way we approach it is often the x-factor between those that succeed at the highest levels and those who don’t.

So let’s WinSmarter on this one!

There’re lots of ways a program can find $2,500 for new uniforms (or anything else they might need!), and I’m sure a bunch of them are popping into your head right now.

I’ll bet you $2,500 (see what I did there?!), that somewhere in your thoughts just now the word “fundraising” popped up. Now, if you’re like me, that was probably immediately followed with an “UUGGGHH…”

No one likes fundraising.

I can give myself nightmares thinking about selling greeting cards, cookies, candy, wrapping paper, towels or some other piece of junk that no one really wants. It takes forever, it’s an administrative pain in our butts, our kids (and their parents) don’t really want to do it, and it really doesn’t make us that much money!

Fear not! There are better, easier and smarter solutions to get you your new uniforms this summer!

When our program needs money to get things done the key thing I think about is a little three letter acronym very familiar to those in the finance world: ROI.

Real simply, ROI stands for Return on Investment. “Return” meaning the amount money coming into your program, and “investment” meaning the amount of time, energy and effort you need to invest to make it happen.

The goal is to figure out what activities have the highest ROI for you… the highest return for the lowest investment.

Starting to come up with any ideas yet?

Summer’s almost here, so I’ll save you some time and give you The TOP 8 easiest and most lucrative fundraising strategies we’ve ever implemented!

We’ve done all of these in our program and, collectively, they’ve brought in thousands and thousands of dollars over the years. The best part about it is they're all replicable and repeatable and none of them involve any fundraising companies where you’re giving away half your profits!

How to think about this list

Now, listen, I realize we’re all in different scenarios with our programs. We’re in different areas of the country, with different communities, different budgets, different demographics and different levels of school, parent and community involvement. The strategies that will work for some of you won’t work for others and vice-versa. That’s why we offer so many ideas, but I can tell you this: ALL of these have worked for multiple programs before and we’ve used every single one of them with success in our program!

The idea here is to use this list for inspiration and get creative. The single best piece of advice I can give you is to read through these ideas and think "How can I make this work for me?" instead of “that won’t work for me because…"

That kind of solution-based thinking should honestly be the number 1 strategy on this list because that’s what will really allow you to get these working for you more than anything else.

And it’s important because creativity counts! For most of us, the winning solution, isn’t any one particular strategy on this list, it’s choosing the right combination of approaches that really yields results.

Hey, if you pick 3 strategies here and one nets you only $1,100, another $800 and a third $600, you still win!

Alright, I think we’re ready to go, so let’s jump in!

Part 2: The TOP 8 easiest and most lucrative fundraising strategies we’ve ever implemented

1. Your administration

Like I said, we’re looking for the highest possible ROI, and there’s no strategy that takes less time than sitting down with your Principal or AD, depending on how things work in your school, and asking for the funds. The answer might be a fast “No,” but if you don’t ask, you’ll never know!

Now here are some things to think about when talking to your administration that might help win him over to your cause:

  • Recruitment value - Make sure your Principal or AD understands that you’re not just looking to be the fashion trend-setters of the sports world. Let him know that this new uniform alternative was specifically introduced to help foster increased participation in the sport. Isn’t increased participation in all sports a goal of your athletic department?
  • Future savings - Your uniforms will have to be replaced eventually. Most school’s replace uniforms for different sports on a time table so they are not hit with too large of an expense on any given year. If your Principal or AD is able to replace your uniforms now, he’ll be saving himself money later by pushing the need for future replacements back a few years.
  • Adjust your budget - Is there room to re-adjust the budget? Is there room to get away with a little less mat tape or other types of supplies next year and free up some of that money for new uniforms?
  • Partial funding works too! Last, but not least, ask your Principal or AD if these solutions might allow him to come up with some of the funds towards the $2,500 you need. Let him know if he can provide some of the funds, you can come up with the rest!

Where should I start?
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2. Booster Club

Whether it’s at district level, school level or even the sport-specific level, many of us have some kind of athletic booster organizations in our school. In my district we have a school-wide, all-sport booster organization that raises money to make purchases for various athletic programs that go over and above what our school budget is able to provide for. The way it works for us is that coaches make funding requests and the group meets monthly to decide what they’re willing and able to support.

In most programs I’ve spoken with, teams very rarely reach out to these organizations to ask for monetary support - after all, we’re not a sport with a lot of equipment needs and we seem to have more of a figure-it-out-ourselves mentality! The fact is many of these organization are looking to support every program in the school, but always seem to get requests from the same few teams, so when a program they don’t usually hear from makes a request, they’re often happy to oblige if they’re able!

When making the request to a booster club, just like when speaking with your administration, it’s important to let them know you’re not just looking for new uniforms. Help them understand that this rule change can potentially have a huge shift on your ability to grow your program and grow its success. That makes this project a win for the kids, a win for their organization and a win for you!

And don’t forget that partial funding would work great here too! Maybe they can’t give $2,500, but how about $500 or $1,000?

3. Go Local

For many of us, an amazing source of untapped resources is reaching out to the local business community! Every business has a marketing budget, and most love to support local organizations, especially sports teams because of the positive values associated with them and the great good-will it creates in a community.

The other huge plus is the sheer numbers involved. Looking at our first two strategies: you only have one school administration you can talk to and there’s probably only one booster organization to approach, but within just a few miles of your school there are likely dozens, if not hundreds, of businesses that would love to be potential sponsors for your program.

As always, let’s think about this in terms of working smarter and not just harder. Don’t just get in your car and start driving door to door! A little strategy can go a long way.

Think about what businesses are best to approach and make a list. We’re looking for businesses that have both the means and the desire to support our program.

For starters, it will almost always be easier to speak to local businesses rather than national chains. Local businesses usually have a more entrenched connection to the local community, they have a stronger desire for their marketing efforts to specifically reach those who live locally and because they’re smaller, it’s much easier to reach the person who makes decisions and there’s much less red-tape to cut through.

Hopefully, you’ve got your gears spinning with some ideas. Write them down now.

Here are some more ideas to add to your list that have worked really well for programs:

  • Car Dealerships - big advertising budgets and looking for local reach!
  • Military Recruiters - they love to be associated with athletics and high school sports in particular! Local recruiters each have their own marketing budgets too!
  • Insurance Agents - see comments on Car Dealerships
  • Law Firms
  • Commercial or Service Organizations - like your local Chamber of Commerce, Elk's Club, Kiwanis, Lion’s Club, Rotary International, VFW, etc.
  • Restaurants/Delis
  • Doctor’s offices/healthcare providers - think pediatricians, orthopedists, physical therapists, etc.
  • Local gyms or martial arts businesses
  • Local labor unions

Once you’ve made your list, start with the most likely candidates and reach out to them. I’ve found face-to-face is the best way to make it happen!

When you do speak to them, make sure you talk about why it would benefit their business with increased exposure and good-will, not just why it benefits your program! What else can you do to help support their business? Give them a shout out at all your home competitions? Hang up a signs asking fans to please support their business? Mention them in your team program or journal? Email all your parents asking them to support these businesses?

You get it.

Not sure where to start?
Download the FREE printable step-by-step action checklist to make it happen. 

4. Parents of current athletes

Depending on your school and on your community’s economics, this might be a solution for you as well. Deciding whether the kids will get to keep the uniforms after the season or hand them back in for use next year will obviously impact the viability of this solution too.

In many areas, your athletes’ families may not have the ability to spend $85 on new uniforms for their kids, regardless.

That’s ok too! One way I’ve seen this solution used with great effectiveness in many communities is asking each family to pitch in a smaller amount to help you get to your $2,500.

Look at it this way: if you have 30 kids (the team size our $2,500 price tag is based on), and each family contributes just $10, you’re knocking $300 off that total very quickly - that bring’s the amount you need down by 12%!

5. Party time!

This is definitely one of my favorites! Every year our program throws a good old-fashioned cook-out and gets awesome results!

On a nice warm Sunday afternoon each June, as the school year comes to a close we host a BBQ and invite:

  • All of our athletes at the youth, middle school and high school level
  • Any friends they want to invite
  • All of their parents, siblings and families
  • Other teams and coaches in our school
  • Our athletic and school administrators
  • All of our alumni recent and older and their parents, significant others, children, families, etc.
  • The entire community

We let everyone know it’s a fundraiser, charge a set price per person, and all the profits go towards our program!

There are two main ways you can accomplish this:

If you’re feeling up to it and you have some help, you can run it yourself with the help of your athletes and parents. This obviously takes more work, but you can make a lot more money towards your goal by keeping the expenses down. A local park or even your school grounds, if they’ll allow it, are great possible venues!

What we do, that’s even easier, is have a local restaurant handle all the food for us. We found a place with an outdoor party area. They handle all the food and charge us a set price per head, we add a bit on top of that to the price and boom! - Very little work, very little preparation and usually about $1,000 in profit coming into our program!

Aside from the obvious fundraising aspect, I’d recommend every program look into this option for all the other benefits:

  • It’s a great way to get your team and families altogether before the summer - these out-of-season fun events can really improve the culture of your program and the commitment level of your kids (and their parents!)
  • It’s a great opportunity for the parents of your youth athletes to meet and mingle with the parents of your older athletes - this usually helps get them pretty excited about the program and what’s in store for their children as they get older
  • It’s a great way to get your alumni back, get them engaged and get them involved in your program - there're probably some huge future donors out there!
  • It’s a great chance for you to showcase the positive values and culture of your program to your AD and school administration
  • It’s a  great way to engage your community and let them “behind the curtain” to see what your program is really all about! I guarantee this will help you with recruiting more athletes in the future!
  • It’s a lot of fun for you too!

Some other “pro-tips” to get the most out of your event:

Get the word out!

Obviously, the way the numbers work with an event like this is that the more people attend, the more money you raise! Make sure you take the time to get the work out in advance! Emails, social media, in-school announcements and flyers around the community all help get you a better turn-out.

Give ‘em another reason to be there!

Every year, we also use our BBQ as an opportunity to induct a new member into our program's Hall of Fame. By publicizing this event ahead of time, we get more alumni showing up to support their old teammates and we often even get local press to cover the event! It’s a win-win for everyone!​

​Rally the troops!

With a (hopefully!) large and “captive” audience, definitely take advantage of the opportunity to give a short talk as the head coach. The script practically writes itself: you can talk about the year’s accomplishments, the Hall of Fame inductee, the state of the program, the potential for the future… leave your kids, their parents, your administration (and potential donors!) fired up and excited about your program and its future!

​Spread your web!

As this becomes an annual tradition in your program, you’ll start to see more and more alumni come out of the woodwork and show up. This is a great thing! Make sure your using this opportunity to meet them, talk to them about the program and get their contact info. You never know when any of them could help you out with donations, coaching or even just connecting with other alumni for networking, job searches, etc.

​Schedule for success!

When planning your event, definitely pick a date that would maximize attendance. For example, we used to have our BBQ on Saturdays and realized a few years ago, in our community, that our attendance would be much better by having the event on a Sunday.

I’d also recommend trying to schedule it during a time when younger alumni are back from college. These younger alumni always seem to heavily attend and it’s a great way to make sure they stay involved in your program without ever losing touch with them!

​Get creative!

The annual BBQ is something that has become an awesome tradition in our program, but if that doesn’t work for you for whatever reason, there are many other types of similar events you could look into to accomplish the same thing. I know of many other programs who throw events like pancake breakfasts or spaghetti dinners in their communities that work really well for them. You’re only limited by your creativity!

Feeling overwhelmed?
Download the FREE printable step-by-step action checklist to walk you through this.

6. Camps and Clinics

If you guys couldn’t tell I’m a huge fan of finding fundraising options that benefit our program in other ways as well. This is another great example!

How about throwing together a camp or clinic this summer to make some extra cash for your program? Now you can help grow your program, improve your kids and raise some money as well!

There’s a lot of ways you can do this, so figure out what works best. Start by asking yourself these questions:

  • Will this be for youth athletes, middle school athletes, high school athletes or some combination?
  • Who will do the instructing and who will be assisting them?
  • What dates and times work best?
  • Can you use your school facilities?
  • How much can you charge?
  • Who can you invite to participate?

If our goal is to execute this strategy as simply as possible, I’d suggest running a clinic for youth players in your area. You can instruct the clinic yourself with the help of any assistant coaches and recruit your high school athletes to be “assistant coaches” as well!

The format that's worked best for us is to have a late afternoon or early evening clinic for three weekdays in a row, with each daily session lasting about 90 minutes to two hours. Keep it simple, incorporate games and other fun activities and use it as a recruiting vehicle for your youth program!

Get the word out ahead of time to surrounding communities using email, social media, flyers and word-of-mouth!

In addition to the value you get out of this for recruiting, it’s also fairly easy to plan, low cost and straight forward to run! If insurance is an issue, look into either AAU or your sport's National Governing Body, depending on your state. They both have affordable options to make this plan work for you!

If you’re looking to get fancy, you can expand the length of the clinic, add multiple sessions, open it up to older kids or even talk to nearby college coaches to see if they’d be interested in being “guest clinicians” to raise awareness about their programs!

7. Make a Journal

Creating an annual journal for your program is a great way to develop a sustainable revenue stream year after year! The first time you do it it requires a bit more effort, but it gets much easier from there!

Essentially, this is going to be like a mini-yearbook for your program. You can include things like headshots and bios for each athlete, team pictures, action photos, statistics, records, awards and program history. Not only does this create a great momento of each season for your athletes and your parents, but it also gives you a platform that you can use to sell advertising space.

Individuals, parents or families can buy an ad to place “well-wishes” to the team or their favorite athlete, but what works even better is the chance to sell ad space to local businesses! You can use the same list that you made in step 3 earlier as a starting point for businesses to approach.

Here’s where delegation comes in handy as well. We have our entire team meet up at the school one morning, divide them up into 4 or 5 groups and assign them an area of town to go door-to-door asking business if they’ll consider placing an ad. We give them a letter from the coach explaining what it’s all about, copies of old journals for them to get a visual example and a rate sheet.

It only takes a few hours and to really get our guys going, we create a competition out of it! The team that gets the most ads gets a free pizza lunch from the coaching staff when they get back!

We’ve always been able to find a parent, athlete, sibling or alumni that is willing to handle putting it all together into a format that’s ready to print and once you have it done once, it really easy to just plug next year’s info into the same template year-after-year!

If that doesn’t work, it’s very easy to find freelance graphic designers online who can do this for you very inexpensively. Similarly, through the “magic” of the internet it’s very easy to find low cost printers that can print the journals up for you and ship them your way!

If you’d like to see an example of our journal, or hear a bit more about finding graphic designers or printers, just shoot me an email at pete@winsmarter.com.

8. The power of outreach

So if you’ve made it this far, you deserve a treat. And quite, frankly, I’ve saved the best strategy for last.

In fact, this strategy is so powerful that it’s allowed us to raise more funds over the years than all of these other methods combined!

And that strategy is an email list.

Say what?

Yep. That’s right. A plain, old, simple email list.

Now it doesn’t happen at the snap of your fingers, but assembling an email list and using it to engage your program’s stakeholders with periodic emails is HANDS DOWN the most effective and highest ROI method of raising funds we’ve ever implemented.

The craziest thing about it: not only does our email list grow EVERY YEAR, but the amount of money that we’ve been able to raise directly from this list has grown EVERY SINGLE YEAR since we began!

All from periodic emails written throughout the season.

Don’t believe me? Here’s a screenshot of a few of our donations from our email list earlier this year.

Why does this work?

Well, there’s some very powerful psychology behind it.

At its core, an athletic program is something very easy for people to get behind. Almost universally, people recognize the values athletics teaches and the character it develops help create great men and women. By sending people periodic emails, you're giving yourself and your program an amazing opportunity to pull back the curtain on your team for people that WANT to be your fans. You’re letting them in on the positive values and philosophies you support. You're introducing them to your athletes and coaches and their stories. You’re suddenly letting them be a “virtual” part of the journey, the struggle and the growth.

This is about as compelling and engaging as it gets for people.

By simply sending out these periodic emails, you’re creating an army of fans ready to jump at the opportunity to help your program, financially or otherwise, when you ask.

And that's the other tremendous benefit of having an email list: your email list isn't *just* good for fundraising. Your email list can help you solve almost any problem your program might have in some way, shape or form:

  • Engaging your alumni if your program's ever in trouble and you need to rally the troops
  • Reaching out to people in your community to help you recruit more kids
  • Increasing recognition for athletes which, in turn, increases their motivation and commitment

The list goes on and on!

It’s really easy for this to sound overwhelming, but the truth is with a sound step-by-step blueprint you can implement this strategy as well.

By investing just a few hours this summer, you can get an email list up and running now and have it start paying dividends to your program for years to come.

The FREE step-by-step blueprint is right here!


This article features many of the most practical, actionable strategies we have for you. In fact it's over 5,000 words long, which can make it a little overwhelming!

So, to make your life easier:

  • Get your own printable PDF copy of this entire post to save forever on your computer or print out for later!
  • Get the printable Initial Action Step Checklists for all 8 of the strategies in this post!
  • Get our step-by-step blueprint to get your email list started with a few hundred names in just a few hours - even if you have no idea where to start!
  • Learn exactly what to include in your emails, how often to send them and how long they should be - so there's no guesswork left for you!
  • Learn how to turn your list into a fundraising machine that works better and better for you every single year!

So that’s it for now.

Hopefully these 8 strategies have given you all the inspiration you need to go out and get yourself some new uniforms this summer (or anything else your program might need!)

Questions about any of this?

Shoot me an email and ask! I’m happy to help!

About the Author

Pete Jacobson created WinSmarter to help coaches with the biggest frustrations we all sometimes struggle with: things like building a strong culture of buy-in, commitment and mental toughness, dealing with difficult parents, recruiting more kids into your program and much more.

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