Grant: Glad to have you here for Episode 399 of The Speaker Lab Podcast! Today, we’re chatting with Tripp Crosby, and right before I hit “record” we were just catching up. We have a lot of mutual friends and have kind of followed each other online for many years, but haven’t actually connected until now. So I’ve been watching him from afar and he’s always kind of dabbling in speaking and different forms of entertainment. And it seems like just recently he’s wanted to start doubling down on this [entertainment], so I decided I needed to figure out what is going on here and understand that thought process. So we’re going to dig into that a little bit – so thanks, Tripp, for hanging out with us for a few minutes for today’s episode.
Tripp: Very happy to be here, Grant.
Where it All Began
Grant: So, let’s start by giving us a little background context. I know you’ve kind of dabbled with some speaking and emcee stuff, and entertaining or performance type stuff. And again as I look in, you’ve had a wide ranging career. So give us a 30,000 foot view of what the past several years of your world has looked like.
Tripp: Well, most people who know of me, know me because of YouTube, because my career started with making comedy YouTube sketches – which was wonderful, but if I had known that was an option I would’ve just skipped college, but I didn’t [skip college], and instead started a little video production company right of school and got really bored with client work.
So my friends and I started making comedy schedules on the weekends and it blew up and we got into YouTube at a really good time. We were able to build an audience really quickly, and being successful, pretty clean sketch comedians made us interesting and cool for brands to reach out and collaborate with us.
So we started pretty soon in our career working with some big brands which over time developed into us building more of a video agency type of business. We were making funny videos for brands, for whatever reason they needed them. And then with that came a lot of requests to come to events.
At first it was me and Tyler together and Tyler’s my YouTube comedy partner. Together we would work at events as comedic hosts and we’d bring all the jokes and we’d also make videos for the event. And so without really meaning to I got a lot of stage time, and in some pretty big spaces with like thousands of attendees and one thing just kind of led to another.
Before I knew it, I was getting regular invitations to come host events. And so I thought, well, this is fun – maybe I’ll be an event host. I sort of did it whenever I was asked to, and I built some relationships with bureaus, but it wasn’t really until this year of my life that I decided to actually double down on this part of my career, instead of just allowing it to be something ancillary I passively take as, as it comes.
Time for Change: Tripp’s Realization
Grant: So, what changed for you this year? Why did it take this long to have the epiphany of “I should be doing this.”
Tripp: There’s a few reasons. One of them is that I just got burned out of doing video work for clients and being the guy running a small business. I love my team and I love making video content – I’m pretty good at it – but there’s something that happens every time that company grows that I don’t like, and I think it’s the fact that I go from being a creator to a businessman, which is not really what I want to do. I realized at the end of last year that, frankly, financially it made more sense for me to double down on this part of my career.
I realized I like doing a few video projects a year, but I don’t like hustling to try and get a lot of video projects so that I can build a bigger team, so that I can get even more video projects so that I can grow some agency, and it’s actually more lucrative to be a speaker.
I realized that this is what I want to double down on, and the more I’ve delved in, the more I realized I was right. I’m starting to find all kinds of energy inside of myself that I didn’t know I had, because I didn’t know I was allowed to do this – because it wasn’t the thing I started out doing.
Grant: So just to be the devil’s advocate though, if you’re running a video production agency, you’ve got two sides of the equation. One is finding and booking clients and gigs. And the other side is creating the videos and doing the art. And the same thing is true for being a speaker – there is the finding and booking the gigs and then there’s the creating the art and most people tend to lean toward the ladder of “I just wanna be a speaker.” But, there’s so much of it as, you know – there’s the actual running the business, the sales and the marketing side. So little of the actual job of being a speaker is actually speaking.
So how do you feel like it’s going to be different, being a speaker and having to do some of the same sort of things in terms of sales and marketing that you didn’t enjoy from the agency?
Tripp: So for a video agency, when we’re working on marketing and advertising projects for giant brands, it takes us months to even negotiate a deal because there’s multiple layers. I have really expensive specialized insurance to run productions and because we’re working with hundreds of subcontractors I’m managing all of these people and their payments which makes my accounting more complicated.
And then these creative projects – they linger on for months. So I’m dealing with start-up clients who just got a bunch of funding and they’re looking at you to make a video, to help their business even work at all. I love that pressure, but I like doing that a few times a year and pouring my whole heart into projects. Scaling and all of a sudden becoming the guy that’s approving all of the other little projects that they’re doing for clients – that’s not what I want to do.
So the scope of all that back end business and marketing is still there [as a speaker] but it’s scaled way back and I actually love that part of it. I think the amount of it that would be required for me to succeed as a speaker would still allow me way more time to write, to express my own ideas, to work on my talks, and to work on a book.
Grant: So let’s go back for a second, because again, you’ve been hosting the emcee stuff for several years and it sounds like a lot of that has been in conjunction with Tyler. You kind of alluded that he’s coming in to partner on some video content?
Tripp: Tyler and I get invited to host together, but more often than not I have been invited to be more of a solo emcee. And now I’m doing more and more keynote speaking.
Grant: So whenever you’ve been doing the hosting gigs, and kind of just doing it on the side, was there an event that you look back on as a potential turning point, like some type of light bulb switch?
Tripp: What if I did this more? What if I did this two or three or four times as much as what I’m doing now? What if I wasn’t doing this thing and I started doing that thing instead? I don’t know if there was a specific event, but there’s definitely been a few over the last year.
Where I left – that was easy. I wasn’t being lazy. I just realized that there’s something that I could do where even the hard work felt easier. Now I leave town, I go to some other city to host an event and I notice how much more singularly focused I am. Whereas at home and I’m in the middle of 10 video projects and it feels like I’m never focused.
I loved meeting new people. I love being in rooms and learning about different industries. The last few times I did it I really sensed how much more singularly focused it is and how easy the hard work felt. That’s when I started going, “Why do I not do this? Why do I not try it?”
This is the best career anyone could ever have. I just go around and share my ideas with people and they clap. And then I leave. I get on a plane. I go home and that’s it. And by the way, I have three young kids. I get to leave for two or three days. This is amazing. My wife’s perfectly happy because I bring money home.
A Personal Brand for Tripp
Grant: So to that end though, what happened when you decided to shift gears and double down on the speaking stuff. What was that conversation with your wife?
Tripp: It came out of being in a dark place where I couldn’t figure out why I had everything I ever wanted, but I didn’t feel like I was scratching the itch. I don’t know if you’ve ever felt like you’re succeeding at someone else’s career, but that’s what I felt like sometimes. It was like, I’m building this agency and I’m learning all these new marketing things and it just didn’t feel like it was me. I was in a dark place and I was stressed and my family felt that.
So when I told Hannah, here’s what I’m gonna do, she lit up. It was like, I’ve been waiting on you to figure this out. And then I met with this consultant, and she was actually a marketing consultant, and she came into town and she was helping us revise our product set and figure out new ways to offer content. When we mapped out the business on the board, she looked at it and she said, “Here’s what I don’t understand – you’ve got Tripp and Tyler over here and you’ve got your company.” She said, “Why are you in the middle of this?” She told me , “You have so much of a foundation built for your personal brand.”
And I was like…that’s it. You said personal brand and I want to throw up in my mouth. I’m tired of hearing about people’s personal brands – too many people have them. And she said, “No, no, you really have one. Why aren’t you doubling down on making content that Tripp Crosby wants to make and sharing ideas with people that Tripp Crosby wants to share?”
And I was like, I don’t know. Am I allowed to do that? Because I’ve been avoiding that for 10 years. I’ve been trying to hide behind some business venture or whatever. And there’s been two reasons. One is I think I was overreacting to the personal brand thing and some of it was confidence.
Most people who follow me online probably think I’m the most confident person out there, but the truth is, I’m like anyone else and the things I care about doing the most are also the things I’m most afraid of failing at. So I’ve had to accept that I’ve wanted to write a book for five years. Why haven’t I done that? Because if I write one, it could be bad. And also I’m sort of learning that I may have ADHD and it’s hard for me to write for more than 20 minutes, but that’s another thing. So, that’s what happened. That’s why my wife is really excited for me and that spills over into everything.
How to Be the Real Deal
Grant: How much of it do you feel like over the past few years was just wrestling with imposter syndrome?
Tripp: There are two things in my life that are both blessings and curses. One is, some of my friends are very successful speakers, like top billing, keynote speakers.
So you know how it feels when you look at someone you’re like, you know what? I should just accept that’s their thing, not my thing, because I’m never going to be a $50,000 speaker, right? Yep. Clearly that was just the wrong perspective, so that’s a blessing and a curse because I could just see that as an opportunity to learn from my friends and ask them questions. The other thing is because I have done a lot of hosting, I have been at a lot of events and I’ve seen a lot of speakers and half of them are terrible. And so the blessing is I’ve gotten to see a lot and learn a lot from watching people do this. The curse is I’m scared I’m going to be one of those people that just kind of gets away with being a speaker instead of actually helping people.
There are some people who have a gift of being convincing and charismatic. And when that gift is used well, it is very powerful and you can help a lot of people. But you can also use it in a sleazy way and not really be an expert on something and not really have good ideas that are tested and you can use it to just weasel your way on stage, get everyone excited, and then walk off and leave people with nothing that great. I’m not saying those people shouldn’t be speakers, I’m just saying they’ve only done half the work and I was afraid I’d be one of those people.
Grant: Do you still worry you could fall into that trap because you’re a guy who’s charismatic? You’re funny. You’re likable. You check a lot of boxes where again, the content could be “meh,” but he was entertaining and so it’s easy to get away with it.
Tripp: Oh yeah. I’m so afraid of that, but something switched this year and I really don’t care as much because, I’ve put myself out there a few times and it has only affirmed that I’m not the smartest guy in the room, and there’s certainly a lot of people with some amazing knowledge, but I do think that because I’ve waited this long and I’m 20 years into my career, I have learned some stuff.
I’ve had to learn it the hard way and I can speak out of an authentic place. So will my content be life changing? No, but it will be very authentic and it will be entertaining.
Building the Business Side
Grant: I want to shift gears for a second. When you think about speaking, there’s a lot of different options of what speaking could look like. We’ve talked about emceeing, hosting, keynotes, workshops, breakouts, seminars, large groups, small groups, and everything in between. So for you, you seem to be gravitating towards emceeing/hosting. It sounds like you’re starting to think about keynotes more as well. How are you kind of thinking about all the different options on the menu, which one makes the most sense for you?
And specifically as it relates to emceeing and hosting – that’s something not a ton of speakers – it’s a lot of work. If you’re just doing a keynote, you show up, do your speech and your responsibilities are largely done. Whereas hosting and emceeing, you’re pretty much on call the entire event start to finish. So how are you kind of thinking about what makes the most sense for you personally – fulfillment wise – but then also from a business perspective?
Tripp: Well, you nailed it Grant. I mean, hosting is a lot more work. I don’t want to undermine the work that goes into preparing an effective keynote. I mean, you’re helping people do that because it’s a lot of work and it’s an intimidating amount of work, but at least sometimes you get to do the same thing twice.
A lot of the time when I emcee I’m actually trying not to do that, because what I notice is that some events don’t really want to spend money there, so they’re used to either bringing in someone internally and that feels like a good idea because it’s free.
But here’s the problem. Without fail you ask your CMO to emcee your yearly sales event. Well guess what? When the event rolls around your CMO is there to network, enjoy the resort, he’s got a million other responsibilities and he’s in meetings, and he’s not going to give the role the attention. So then the other option is, well, let’s get a local radio personality, or like let’s spend a lot of money and bring in a big name person. Right. Let’s bring in Jimmy Fallon or something. Well, that’s great. That’s gonna sell tickets and there will be some funny moments, but guess how many pre-event calls you’re gonna get with that person? Zero.
So my selling point is that I’ve worked with many events as a consultant on programming teams. I know events, I understand events. I do know how to engage your audience. I do know how to make it fun for people, but where I’m really gonna invest my time is being an expert on your event and your theme and your audience, because I realize you’re trusting me to, in some sense, be the face of your event.
Grant: We don’t talk a ton on the show about emceeing, but it is absolutely a viable option for speakers. So we talked about the downsides, it’s just a lot of work, fewer events actually have budgets allocated towards something like that. What are the upsides of it?
Tripp: The most rewarding part of being an emcee is seeing an audience feel things. When it works and you can tell that an audience is more connected to the whole thing, it’s very rewarding. It’s not even about me, you know, when you give a keynote and people clap and come up. That’s great. And you feel good about your thing. But when people like you as a host, it’s because you helped an event win their thing.
Grant: How are you thinking about balancing the entrance, the interest, and the experience with emceeing/hosting?
Tripp: I mean, the truth is I’m going to try and book as many of either as I can. And whoever asks for one first will get that time slot. I truly love both.
Grant: So we’re about two years into the pandemic. Hopefully we are past the majority of it. But there’s also still a lot of events that are existing in a virtual environment. Are hosting and emceeing opportunities available in a virtual environment?
Tripp: I prefer virtually to speak because I mean, what can a host do on a Zoom? Right? I can’t really feed off the energy of the audience.
The times it has worked really well is when a company has hired me to pre-record my hosting segments. I will record eight or nine transitional segments that they can play in between their other content – that works really well.
I’ve done some interviews via Zoom and that’s fine, but the thing I like about hosting is the thing that I mostly get out of being in a live room. It’s hard to replicate. It’s hard to duplicate. And I feel like if I’m speaking and really my job is just to talk for 30 straight minutes, I can do that.
Grant: I want to go back to something we alluded to and where this whole conversation kind of came on my radar – an Instagram post that you made. It said, “Hey if you’re looking for someone I’m doing this more and again, kind of planting your flag on it.” I was curious, what kind response did you get to that?
Tripp: It was really encouraging. You know I’m not going to get gigs right away because these events are planned months in advance, if not a year. Even though I did get some and I’ve had some great phone calls with new agents that I didn’t know were out there for different bureaus. But the real encouraging thing was how my followers responded and people like you saying, “Hey, like, this is cool. Like we need to talk about this.” I’ve got a couple of podcast invitations and just a lot of encouragement from people that I now realize don’t really know what I’m all about.
Grant: It’s something we tell speakers all the time, that when you first start speaking one of the things you have to do is let people know that you’re a speaker. Otherwise people would never think of you as that. Until you plant the flag and say this is what I do. People won’t make that connection unless you give them the opportunity to make it.
Tripp: One of the things I learned while I was deep diving into my educational marketing is just how many times you have to remind people of who you are and how you can help them before they actually engage. Ido think it’s important to remind people that you’re a speaker. Or whatever it is you do well.
Grant: I want to ask you this to kind of wrap up. You’ve dabbled in speaking for a while. You decide to go all in. There’s a lot of people listening in that same spot. And so what would you say to the Tripp of six months? A year? A couple of years ago, who may be listening, going like, “I think I can do this. I would like to do this. And for whatever reason, there’s something that’s holding me back.”
Tripp: The first thing I would say is probably not the thing that they would want to hear. The first thing I would say is speaking is one of those career paths. That way more people will want to do it than should. A lot of people want to grow up and be pro-athletes. A lot of people wanna grow up and be movie actors. A lot of people want to be touring recording artists, right? There’s a lot, and speaking is somewhere on that scale. Not as far up as an NFL quarterback, but it’s just one of those things that way more people will want to do than they can, because it’s something that gives you notoriety and attention and who wouldn’t want to do that?
So the first question that I think someone should ask themselves is why do you want to do this? Are you sure this is what you want to do? I’m realizing I am set-up to do this and I may not be the best in the world at it. And I may fail trying, but it is something that I should at least fail at. Because all of my experiences add up to this and I know I’m in a place in my life now where my ego is smaller than it’s ever been. It’s still there, but I just don’t need to do this for validation. I’m very comfortable with who I am. I’m very comfortable with what I’ve already accomplished and I don’t need validation. So I can honestly say that’s not what this is.
And, and a lot of people are looking to be speakers for that [validation]. And there are much better ways to find meaning and significance in what you choose to do than to try and be someone you’re not. So that’s probably not the answer you were looking for, but that’s what I would say.
Grant: Thanks for the time, man. We appreciate it. If people wanna find out more about you, where can we go?
Tripp: I’m pretty easy to find. My website is trippcrosby.com and all of my social handles are @trippcrosby.