EP 91: 19 Years of Derby Day -- Elevating a Fundraiser from Backyard to Main Stage

This conversation is for informational and educational purposes only and is not professional advice.

Positioning review: Content reviewed for positioning compliance. References to Handbid are experiential -- describing the founding story at Jeff's own Derby event and general event technology observations rather than product promotion. Event planning advice framed as personal experience and observations from 19 years of running a specific fundraiser. No financial, legal, or professional advice present. Minor cleanup of filler words and transcription artifacts.

Jeff: Welcome to Elevate Your Event, your favorite podcast for transforming fundraising events. Join us weekly for expert tips and creative ideas to make your next event a standout success. This episode is all about one event, 19 years in the making. From backyard parties to full-on outdoor productions with fire pits, live music, and sold-out tables, Jeff shares how they've continually elevated their Derby Day fundraiser. If you're looking for real-world insights, bold ideas, and a few laughs, you're in the right place. Let's dive in.

Cohost: We should do an Elevate Your Event dad jokes episode.

Jeff: Totally. I think that would get some good traction, because who doesn't love a good dad joke? We used to do it as a contest when we were on that podcast. The whole goal was you would have to tell the joke, and the person across from you was not allowed to laugh at your joke.

Cohost: So it'd be like, if you can have him spout these jokes at you and not laugh, you win?

Jeff: Yes. Do you see, what's the name of the Instagram channel that has the two dudes sitting on the dock telling dad jokes all the time?

Cohost: Oh, yeah. Whenever that pops up in my feed, I'm like, oh, this is good. Because they're just real serious, looking out into the distance with their coffee.

Jeff: Well, hey, we're here. Spring has sprung in Colorado. And you are in the thick of planning an event.

Cohost: I know.

Jeff: I thought it'd be interesting if we just chatted a little bit about that event, talk about how things are going, stuff that you maybe learned from last year and that you're going to try to implement this year. I know this is Elevate Your Event podcast. So let's talk about how this year we've continued to elevate our event.

Cohost: Believe it or not, this is year 19.

Jeff: 19 years, almost 20 years. Can you believe that?

Cohost: You were 18 when you started the event.

Jeff: It would have been 20, but we took a year off. And ironically, it wasn't the year of COVID that we took off. Back in 2020, we actually did run the event and it was one of those home-based party events. The Derby for the first time -- maybe ever -- moved from the first Saturday in May to Labor Day weekend that year during COVID. So we did run an event and we used some really cool technology and incorporated Handbid into it. We had a series of small gatherings, house parties. We did it, but that wasn't the year we took off. We took off the following year thinking we were going to move this event to the fall and turn it into a country music concert because we just felt like that's what our guests wanted. But we were wrong.

Cohost: Because you love country music.

Jeff: I do love country music, but at the same time, I love the Kentucky Derby. This was a party that we had at our house before it was even a fundraiser. Once we did that, we actually attended a different derby party that year and got a little taste of what was going on in Denver and decided, yeah, we need to bring the derby back and make it the type of event that's going to cater to a different crowd than maybe the one that goes downtown. We'll talk more about that because that was one of the big changes we made this year. But just a little short history on the Derby. It was a party Carrie and I ran at our house for a number of years from my East Coast heritage. We came out here to Colorado. I tried to get people that lived in Colorado to actually dress up like you do for horse races on the East Coast. That didn't work. Like 20 years ago, that wasn't the vibe.

Cohost: It still really isn't. I mean, some people do attend the Derby now and the ladies will wear their hats and get into it.

Jeff: But back then, we were like, "Hey, you know what you do at a horse race in Virginia or Kentucky? Men wear suits and ties." No, not in Colorado.

Cohost: Last year was my first time coming to the event. And that was kind of part of the fun. My wife went and found this lady who made hats, and she got a hat made. And I got to wear a fedora and put on a ridiculous pink jacket. And it was cool.

Jeff: It is cool. And I think part of it also, when we started this event 20-plus years ago, we were way younger and maybe that just wasn't as cool as it is when you're our age now. Anyway, we turned it into a fundraiser in 2006. What ended up happening was interesting. You start sending out invites and telling your friends, "Hey, we're still doing the derby event, it's coming up, but it's a fundraiser now." There was a major shift in the people that came.

Cohost: Really? Do you think it was because people were afraid? Like all of a sudden there's an expectation you might ask for some money?

Jeff: There was absolutely an expectation we were going to ask for money. And sell tickets to it. I'm not even sure we sold tickets year one. I think we just asked people to donate. We had an auction and some other things going on. But prior to that, it was an event where Jeff and Carrie were footing the bill for everything. The mint juleps, all the food -- just catered and paid for by us.

Cohost: I found a video on our channels of you making a mint julep in your kitchen or something.

Jeff: We did that in Tim's kitchen for the 2020 video. I'll link that in the video. You guys are making mint juleps -- it's a great video. It feels like a food show. I got pretty good at it. We would do all that kind of stuff. And then when we launched it that first year as a fundraiser, I was like, "Oh my God, these people are no longer coming." A whole new set of people started coming. And you really start to -- people will shock you with their generosity and in ways that you probably don't expect. Because everybody feels like, "I'm going to invite all these super wealthy people and they're going to donate all this money." But one of the things we learned very quickly is that rich people aren't generous. Generous people are generous. It doesn't really matter. People give out of their hearts.

Jeff: That first year, I'd call it a success. I think we raised $7,000 or something like that. We were so shocked and excited.

Cohost: Especially when you're not expecting anything. Low expectations.

Jeff: It was one of those things where it was a lot of fun. Clint Hurdle was the manager of the Rockies, and the Rockies were about to go to the World Series, so they were still reasonably good at that point in 2006. He was extremely generous and had connections. The Rockies were very generous to us. So that was a good start. And then obviously Handbid came out of all of that. Five years later, we launched Handbid when we were at a much bigger venue than our house -- the DU Cable Center. I just decided we wanted a better guest experience. So we launched Handbid. Who knows what that was going to do. It was one of those things where it's either going to be awesome and amazing or another fail. But like Theodore Roosevelt says, "For those who fail, at least they fail while daring greatly." So we dared greatly. And it was a success. Obviously, we're still here.

Jeff: We started to think about how do we continue to make the event better. From 2006 to 2011, it obviously outgrew our house. Our neighbors were really happy when there were no more tents and 200 people were not at our house. We moved to the Cable Center at DU. And then from there to Infinity Park. And what did we do there? Infinity Park in Denver is a venue that's got wraparound video walls in it. Really slick. You meet with the video team and they tell you all the capabilities. And then we're like, "Sweet, we're going to go make it happen." We had the feeling of horses racing around the top -- it's an oval venue. And they had cameras pointing to all these different walls. Roses. It was so much fun just taking it to the limit because a lot of charities roll in there with their PowerPoint slides and I'm like, "Julie, no. Tell me what this place could actually do." And we figured out how to stitch together graphics to make it really cool.

Jeff: We were there for a while and that kind of elevated the experience. Unfortunately, the City of Glendale, Colorado's liquor laws are really hard. Not favorable to mint juleps. They're like regulating mint juleps. Obviously, we want a safe and fun event, but I can't have my guests waiting in line because it's one drink per person and all this other bizarre stuff. So we had to leave there.

Jeff: We ended up bouncing around to the Broncos facility for a year.

Cohost: That's cool. How do you plan these things? Is it through networking relationships? I'm assuming as a nonprofit, your budgets are extremely low and you don't have the money to pay 10, 15, 20 grand to rent a space.

Jeff: They range. And every time we moved, it cost more. But that's the concept of ROI. For a lot of nonprofits and boards, they try to look at it as a fixed budget. "I sold $70,000 in tickets last year, so that's what I'm going to make. Or my event did $100,000 and that's what I'm going to make. So why would I go spend money on these other things?" And what you have to say to yourself is, "I'm going to go spend money because I expect to make more than $100,000." Why would I go invest in something new? Why would I improve the venue? Why would I change the catering unless the entire purpose is to save money? But that's not always the entire purpose. We moved from the Cable Center to Infinity Park because we wanted to upgrade the experience and felt like that would drive more ticket sales. It's a bigger venue. And then with the Broncos facility, it was even bigger. But we learned our lesson there with the logistics. The AV company we hired gave a really meh experience. This is the Kentucky Derby. It only lasts for like two minutes.

Cohost: That was a surprise to me. I was like, "Is this the warmup lap or something?"

Jeff: Don't go to the bathroom. You're going to miss the whole race. That two-minute race -- when you can't see it or the sound isn't good or the auctioneer can't be understood -- that takes away from the experience. So we decided we need to upgrade further. Go even deeper.

Jeff: How did we end up where we are now? During COVID, we became really good friends with the owners of Fiddler's Green, which is a large outdoor amphitheater here in Denver. When I say large, you can pack 15 to 20,000 people in it. They were taking this drainage open-space piece of land connecting Fiddler's to the rest of the streets around it and turning it into a park. One night during COVID we went over there. He took us over to Fiddler's, opened the gate, showed us what he's building. I said, "This is awesome. I want to run my fundraiser here." This is like the fall of 2020. He was like, "Okay, when's your fundraiser?" "First Saturday in May." "We'll be ready." They were still putting sod in the week before our event. But that's what this is all about. We were the first event ever done at that park.

Jeff: Now, I don't think most nonprofits would do this, but we went out and I bought 120 plastic Adirondack chairs from Walmart. And we bought 20 fire pits. And we put together 20 fire pit tables at Fiddler's.

Cohost: Wow.

Jeff: We had a stage. We brought the stage in. We hired a band that actually does pyro for the Broncos and the Rockies. That guy had a firework show. I love the caterer we used for years and years, but it just didn't feel like the vibe we wanted outdoors. So we went to food trucks. And we've evolved from food trucks too. But the point is, we made a lot of changes. What would it cost to put together 20 fire pit tables? I don't know. I sold the tables for $2,500 each and we sold out. So it worked out for us. And it's an investment -- we still use the same fire pit tables.

Cohost: You made the investment back then with the hopes you'd make that money back, and you clearly did at $2,500 a table.

Jeff: We have a massive LED screen. Not the junky rear-projection things we had at the Broncos facility where no one could see the screen. These are full-on outdoor LED screens -- the same you see at a concert venue that hang on the walls. We rented one of those. That's like eight grand right there. We were not spending that before. But this is the experience we wanted. And I had a bunch of board members going, "What is this going to cost?" And I'm like, "I know it's okay. We're going to make money. Don't worry." Even if we fail, we will fail daring greatly. We're not going to lose money on this event. We're going to try things and some things are going to pan out and some things aren't. But we felt like these would create the experience we wanted. And then that experience would drive ticket sales, donations, paddle raises -- all of that. New LED screen, food trucks, and we are not putting out six-foot rounds with chairs in the grass. We're just not doing it.

Jeff: Denver -- people who are not familiar -- late April through late May is either 80 degrees or it's snowing. Nothing in between those two extremes. Windy, snowing. It does settle down by the end of April, but it could be really cold in the beginning of May. So you're going to do an event like this and it's like, I want a fire pit table. I want to create that connection between the outdoor event, the Rockies, everything. Because we moved outside. It's like running a golf tournament -- everybody freaks out about rain. "Don't run a golf tournament if you're going to get freaked out about weather." But for us, this is the Derby event. It feels like it should be outside. And this is unfortunately not Miami. So we had fire pit tables. We had a sponsor that provided several hundred little flannel blankets that we put on every chair. We created the experience we were looking for. Where did I get that idea? From another event we had done at Handbid. They had fire pits, blankets with plastic outdoor Adirondack chairs and they're comfy. People liked the vibe. You just sit back, the band's playing, you're hanging out, drinking your mint julep. It's a good event.

Jeff: We made another change because our Derby event used to end at 6 o'clock. The Kentucky Derby race is typically about 4:50 Mountain time. Two minutes later, it's over. We'd do a quick live auction, a little presentation, close the silent auction. 6, 6:30, people are out the door. No -- we put on a full-on concert that night. So now these fire pits really matter because the temperature -- here's the other thing in the spring in Denver. It's nice out, 75, 80, short sleeves. You're at 6,000 feet so the sun is beating on you. And as soon as that sun goes behind the mountains, it drops like 30 degrees in three minutes. So we wanted that experience -- fire pits rolling. And it looks unbelievable when it's dusk and you've got a band coming on stage and 20 to 30 fire pits all going. That's exactly the vibe we were looking for.

Jeff: And then we had our little hiatus where we decided, "Let's just turn this into a country music concert in the fall." Which came with its own set of challenges. And that was a lot of people missing the derby. The following year, 2022, we decided to do Country for a Cure in the fall. And on Derby Day 2022, I must have gotten 20 or 30 text messages from friends saying, "We missed the derby event. It's Derby Day -- what are we supposed to do?" There's a big Denver Derby party downtown. So we went to that. And I was like, "This is not for me." Driving downtown Denver is a hassle. Parking. All these drunk party people. It was a giant frat party. Two or three thousand people. The food is -- okay. The catering was all right. My mint julep got served out of a soda gun at the bar. So you've seen my video on how to make a mint julep. Did you see me using a soda gun? No, it takes a lot of intentionality. And I got the last one. The guy's like, "We're out of mint juleps." It's 2:30 in the afternoon. The race isn't for another hour and a half. And nobody really knew what the charity was about. It's not my music, not my vibe. I'm not here to pick on them. They do an amazing job. But it's not my vibe.

Jeff: So we came back and said, "We're doing the derby. Bringing it back." Brought it back last year. Bigger and better than ever. We're going to continue to elevate it even higher. We brought in higher-end fire pits. So we have our six-person fire pit table at $2,500. We brought in a $5,000 fire pit table with seats for eight to ten people in a premier spot. And we sold all four of them in a week.

Cohost: That's awesome.

Jeff: Okay, this is an unmet need. So yes, I had to go out and buy more lawn furniture. Four outdoor sectionals that came with a fire pit. And Costco had the fire pits. I'm sitting there with Carrie, we're walking through, and I'm like, "These things are $500 on sale for $200. We're buying four right now." She's like, "That's a pretty good deal." "Yes, we're buying four of them right now." They're not fitting in my Tesla, so "Honey, you run home and get the pickup truck. These are going home with us." We're always thinking Derby year-round. "We need that for the Derby -- grab it now."

Jeff: That was a great success. We walk out of that last year and we're like, "What do we want to do next?" We always do a survey when we're done. You get a range of feedback. All of their opinions matter. Some may matter more than others, and some are probably not worth dealing with.

Cohost: It's like that one star on Amazon where they're like, "The shipping was late." Nothing about the product.

Jeff: "They misspelled my name on my name tag." Okay, sorry about that. But there are nuggets in there. And you have to make sure when you're dealing with your board and event committee that you put everything in perspective.

Jeff: Last year, I'm sitting there -- we had hired an event planner for the first time. Can you believe that? 19 years ago.

Cohost: That's wild.

Jeff: Because we know how to plan an event. It was always like, "Why would we hire an event planner?" But I was done running around the venue dealing with problems, especially when I bought a table like everybody else. So we hired an event planner and got noise from our board. "What is this going to cost? How is this going to drive revenue?" "It's not going to drive revenue. It's going to keep me sane." So we hired the event planner and I'm sitting at my table for the first time in 18 years. Like, "Oh my God, I get to sit at my own table that I bought."

Cohost: You had a cool guy emceeing so you didn't have to worry about getting on stage.

Jeff: I had an amazing emcee. Maybe he'll come back this year. And this lady comes up to me and says, "It's just too loud." My table is 20 feet from a wall of speakers. I'm thinking, "I agree with you. It is loud right here. But this isn't your table. It's mine." We had a good conversation. She had not bought a table. But I could just blow this off as "this lady doesn't like loud venues." People complain to the Fiddler's owners that their concerts are too loud. It's an outdoor concert.

Cohost: I can hear Fiddler's from my house. Probably three, four miles away.

Jeff: But I said, there's something to be said about this. What elevates the experience for our table purchasers? So we decided this year, based on that one person's feedback and a very good conversation, we're going to swap some stuff around. We're going to move all the fire pit tables back. Very similar to what you see with suites and boxes at arenas. If you have a suite at a Nuggets game or an Avs game or a box at Fiddler's, you're not in the front row. You want that elevated experience. You want to be back a little, in a bigger, wider, more exclusive space.

Jeff: So now we've got all this open space in front of our stage. I think it's going to be good. It's going to feel less intense for the folks there. Because it was always funny -- "Who's going to be in the front row?" There's no advantage to being in the front row at an event like this. Every seat's a good seat. The way this park works, there are these tiers. When you come in through the main entrance, there's a tiered set of grassy areas that go down to the base where there's a circular grassy area and the stage. So it does feel elevated and better when those fire pit tables are back.

Cohost: And when you're bringing guests, there's an element of it being a great place to network and connect and talk. If you're right up in there, it's harder to have that communication experience.

Jeff: One of the folks at our table last year was the CEO of Make-A-Wish Colorado. I'm trying to have a conversation with the guy. "So what do you think? You love it? Isn't this a great event?" And you can't really yell like that. So when you pull that back, you'll be able to do that. Not really a cost change. But an experience and environment change. Not everything you have to do is going to cost you money.

Jeff: And we tweaked the food. We met with the caterer this year -- same guy, he creates the perfect vibe for our event. We're going to make some changes to the menu based on feedback from last year. Elevate a couple of the items. Not going to cost much more -- a dollar or two a person. We do that in all areas of our event. What worked well? What do we want to change to make the experience better?

Cohost: It's almost like this mindset shift -- an abundance mindset instead of scarcity. Instead of, "We're trying to keep as much money as possible," you're saying, "What can we do to make a great experience for people?" Obviously you want to be cognizant of costs. But really pushing into what is it going to take to make a great event, a great experience. And that will beget the funds and the generosity.

Jeff: For sure. And then the next thing we decided to do -- and I was shocked our board agreed to this, but they were all on board -- the charity element is obviously very important. But the Derby has taken on a brand of its own. It makes sense to brand this as just Derby Day at Fiddler's Green. Yes, it benefits the Prader-Willi Syndrome Association of Colorado, and those things are important and prominent in what we do. But we have rebranded this event as Derby Day at Fiddler's. And it is, no doubt, Denver's classiest derby event.

Cohost: That's cool.

Jeff: You don't have to go downtown. You don't have to park. You don't have to use a porta potty. You don't have to deal with chaos. It's a different vibe. We have awesome food. We have Rocker Spirits that comes with this early 20th-century California trash truck that the guys converted into a portable bar. And he's serving mint juleps. Ironically, they're pre-mixed and pre-made, which I was absolutely skeptical of. But they're fantastic. Really good. The way he makes them -- because we've tried all the pre-mixed stuff and I've always slapped the caterer's hands for doing that because it never works. This guy's got it down. We have vodka drinks, mint juleps, old fashioneds. The truck has a flamethrower on it too.

Cohost: That's sick.

Jeff: And then we have beer and wine and non-alcoholic drinks. We just continue to elevate those. All aspects of the event, we look at every year -- what do we want to tweak? This event, as we continue to elevate it, is going to bring more people spending more money. It will absolutely be one of the more prominent events hosted in the South Denver area every year. That is our goal. And all of those things will impact revenue for the charity. The problem is, Prader-Willi syndrome is a rare disease. If you're just relying on the community of people impacted by it or familiar with it, it's a very small percentage. But how many people in Denver want to go to a derby party? A lot. Do we feel like we're compromising our cause? We don't. What we said is, we're going to make this such a prominent event that when people get there, we get to introduce so many new people to what this charity and organization does because we got them there in the first place. That was a mind-shift change, but everybody embraced it.

Jeff: Derby has its own website now. DerbyDenver.com. Check it out. We have it. The other guys have the other domain, but we have this one. We're bringing in Mitch Rossell from Nashville. He was on America's Got Talent. He opened for Garth Brooks. So he'll be our headliner band. We have continued to elevate the entertainment vibe.

Cohost: That's awesome. And I know we'll do a recap of the event after it happens on the show. It'll be cool to see how things pan out.

Jeff: And then the last bet we've made -- this hasn't fully panned out yet because the event hasn't happened -- we have hired a group to go out and cold-call to get sponsorships. Part of our thought is, we just don't have the time. These guys are making 1,500 calls a week in Denver and booking sponsorship appointments with our team to close table sales or bigger sponsorships. If you're the type of charity that has zero issues selling out your tables, you don't need this. But if you do -- it's an experiment for us. We're not going to lose money on it. Based on the appointments we have, we're going to at minimum make a little bit on it. But it's going to teach us a lot. We're learning what types of organizations are interested in sponsoring an event like this and bringing their customers to it. Law firms, real estate groups -- this is stuff we need to know. We have our connections. But as we continue to grow -- this is a fixed-size venue. I could probably fit a thousand people. We average about 400, so I could double the size. But I want to be careful not to compromise the experience. I don't want this to be standing room only. It's a classy derby event. We might continue raising the price and bringing in more exclusive acts to create that elevated experience. Handbid has powered a number of these. We've seen it work. I've seen a room with 500 people raise two and a half to three million dollars. So you don't need 4,000 people in a venue to raise $2 million. You just have to create the right mix.

Jeff: We'll see how this plays out. When we do our recap, you can ask me how the cold-calling for sponsorships worked. I'll let you know.

Cohost: I'm excited. It's going to be a great event this year. It'll be cool to see how implementing these different things affects the experience. And I love the idea of making an amazing event to draw people there and then having the ask, the auction, whatever that might be. Because then you have people having a good time. One of the best events I went to -- I talked about this earlier this year -- was that Young Life event in an airplane hangar with super cars.

Jeff: It was just so cool.

Cohost: It loosened my pocketbook to want to give some money. It wasn't the old-fashioned -- it was the supercars and the helicopter ride. Everything about it was so leveled up that I was like, "Except for the software." That was the one thing that was terrible.

Jeff: They did not use Handbid, by the way.

Cohost: That would have been the cherry on top. But yeah, just make a great experience for people and the money will come.

Jeff: And it's the same approach we take with our software application. You don't want software to get in the way of having a great event. You want the software to complement that. Everything we do inside our platform has that same approach. Is this going to make the guest experience better? We care about the manager experience and the event host experience too. But the guest experience is what's going to drive the revenue. That's the same thing here when we're talking about these changes. I'm excited to do the event. It's not far off. Creeps up on you fast -- it's like four weeks away. By the time you listen to this, it'll be a week away or whatever.

Jeff: All right, well, hey. Great. Thanks for all the stories and feedback. Good conversation. This event's near and dear to our hearts. And obviously special to Handbid as well. This is where Handbid was born, believe it or not, at this fundraiser. Because if you're going to launch new software and test it somewhere, you should just test it on your friends.

Cohost: The ones that won't hate you if it doesn't work.

Jeff: Exactly. All right. Until next time, happy fundraising. If you enjoyed our show, please take a moment to leave us a review. You can find us on Apple, Google, and Spotify. Don't forget to subscribe for more great content. And if you're a fan of video, check us out on YouTube. Until next time, happy fundraising.