Exploring Paid Prospecting: Revolutionizing B2B Sales with Pitchfire

About the Guest(s):

Ryan O'Hara: Ryan is the co-founder of Pitchfire, a forward-thinking company revolutionizing sales prospecting through their innovative "paid prospecting" model. With a strong background as the former VP of Marketing and Growth at Lead IQ, Ryan has significant experience in sales, marketing, and category creation. His expertise in building marketplaces and go-to-market strategies has made him a respected name in the B2B sphere. He is known for his engaging content on LinkedIn and is deeply passionate about enhancing both prospecting effectiveness and creativity within the sales process.

Episode Summary:

What up What up - join Taylor Wilson on this episode of the Talking Shizzle podcast as she chats with Ryan O'Hara, co-founder of Pitchfire, about the future of sales and marketing. The episode is packed with insights into Pitchfire's innovative approach to sales through their paid prospecting model, aiming to reshape interactions between buyers and sellers in the B2B space. Ryan's expertise in category creation, coupled with his creative strategies for engaging content, make this episode a must-listen for entrepreneurs and marketers seeking fresh ideas.

Delving deeper into the discussion, Ryan shares how companies can significantly improve their prospecting efficiency by adopting a paid response strategy rather than traditional methods. He explains how Pitchfire's platform allows companies to seamlessly integrate paid prospecting into their go-to-market strategies, essentially creating a new channel alongside outbound prospecting and paid marketing. The concept addresses issues with traditional prospecting methods, offering a solution that benefits both sellers seeking strategic insights and buyers receiving a token of appreciation for their time.

Additionally, Ryan discusses the broader challenges and changes on the horizon for marketing and sales, emphasizing the role of artificial intelligence as a creative and efficiency partner. He also touches on the concept of category creation, offering practical advice for companies looking to differentiate themselves in crowded markets. Listen in to discover how Pitchfire’s innovative solutions and Ryan's marketing wisdom can provide a blueprint for success in the evolving B2B landscape.

Key Takeaways:

• Paid Prospecting as a New Channel: Ryan discusses how Pitchfire introduces paid prospecting, allowing businesses to pay for responses instead of meetings, enhancing engagement with potential clients.
• Category Creation Insights: The episode highlights strategies about defining a new category within your industry to distinguish your product and drive market presence.
• Efficiency and Creativity in AI: Ryan views AI as a tool for creative enhancement and improving efficiency in content creation, bridging the gap between imagination and execution.
• The Evolution of Sales and Marketing: Dive into Ryan’s predictions on the sales and marketing landscape by 2025, focusing on the growing importance of innovative engagement strategies.
• Practical Advice for Startups: From updating domains to effective pitching, Ryan shares personal anecdotes and actionable advice to streamline startup operations.

Resources:

• Ryan O'Hara's LinkedIn

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Transcript

0:00:03 Taylor Wilson: Hey, hey, hey, all you lovely people out there. I know you’ve got a lot going on in your day and you have.

0:00:10 Taylor Wilson: Big dreams for your brand.

0:00:12 Taylor Wilson: Are you ready to talk some shizzle and learn some shizzle from entrepreneurs, leaders, change makers, and overall interesting people who like to shake things up? I’m your host, Taylor Wilson, founder of Creative Shizzle, and I’m stoked to bring you a fresh episode of Talking Shizzle today. This show is all about helping you think differently so that you could grow.

0:00:39 Taylor Wilson: Your business or your cause.

0:00:42 Taylor Wilson: Check us out on the web at creativeshizzle.com now let’s get into it and talk some shizzle.

0:00:51 Taylor Wilson: Hey, Ryan. I’m here with Ryan O’Hara today. Good to see you, man. How are you?

0:00:56 Ryan O’Hara: Thanks for having me on, Taylor. I appreciate it. Yeah. We first met out in Vermont, in Burlington, and I got to meet a little bit more about your company and what you guys are doing, and I’m really excited. I put on my nice sweater today. I could have wore a grubby shirt, but I. I’m wearing a nice sweater for you today.

0:01:10 Taylor Wilson: It’s good. I like it. I. I like the stripes. I feel like you don’t see stripes as much these days, you know, but, like, you can get old school.

0:01:18 Ryan O’Hara: Yeah, Me, definitely. Definitely. You know what stinks for me is when I do videos and stuff. Now a lot of the videos I do for Pitch Fire, I will use a green screen, and I can’t wear green because if I wear green, my shirt gets canceled out. So I have to be very careful about what color shirts I buy when I’m wearing them for work.

0:01:36 Taylor Wilson: Is green your favorite color?

0:01:39 Ryan O’Hara: It probably would be otherwise. So that’s kind of the tragic part about it. But I can’t do a blue screen because my eyes are blue and they look like a weird alien if I cancel out blue in my video editing. So green it is, and I just basically have to avoid wearing green stuff.

0:01:54 Taylor Wilson: Is that a green screen or is that a real background?

0:01:57 Ryan O’Hara: This is a real background. My green screen. Hopefully it doesn’t disconnect. My camera is literally on the other side. Oh, I can’t flip it. I can’t flip it. You’re not going to see it because my camera is on a tripod and I can’t fix it. Green screen’s right behind the camera. So I have two studios in this room, and I flip them. This is my analog studio. That’s real like that you can touch stuff and.

0:02:16 Ryan O’Hara: And then I have, like, a whole digital studio. Behind me in the room that I’m in.

0:02:20 Taylor Wilson: Okay. Yeah. Because I love your videos like that you put on LinkedIn. So you’re a lot of times using a green scre screen with those.

0:02:27 Ryan O’Hara: Yeah, the ones. Anything. Anything with a colored background is usually me using a green screen. Anything with this in the background is usually real. That’s kind of the typical rules of thumb. I used to have a monitor that would play a fireplace in the background while I was talking. And I did that since lead iq. There’s a whole story there. But my laptop that streams it just has notifications come up like crazy now because I’m getting calls and emails and bothered by people all day, and I can’t mute them. So, like, I stopped doing a green screen or I stopped doing the fireplace in the background because of that.

0:02:58 Taylor Wilson: I remember the fireplace. The fireplace you used. Like, what was the origin story of that?

0:03:04 Ryan O’Hara: So I went to a conference when I worked at. I used to be a VP of Marketing and Growth at LEED ikea. And we went to a conference. Yeah, yeah, yeah. And Salesloft was having a user conference. We sponsored and had a booth, and we put a lot of time into having, like, a booth reel that would show the product so that people walk by would just keep looping and showing the product. And for two days, like, our booth was okay, but the traffic wasn’t great.

0:03:29 Ryan O’Hara: The last day, our guy that had the laptop with the video flew home early because he had an emergency in his family. And so we didn’t have a video for the last day because no one thought of getting the copy of the file. So I just went and found a fireplace online and put it up on the screen and streamed it. And we had more booth traffic from the fireplace in that day than we did all the other days combined.

0:03:51 Ryan O’Hara: And I was like, I’m going to just start doing this and everything that I do for videos and stuff. And it’s kind of funny because I eventually started a company called Pitchfire, but, like, kind of has some symbolism with the fire a little bit.

0:04:01 Taylor Wilson: Is that why was, like, the fire like, you were bringing that back or like, that somehow or what?

0:04:07 Ryan O’Hara: It was accidental a little bit. So, like, what happened for me when I was. So when I first started pitchfire, we originally were called Requests for Meeting, and it was like a marketplace where you could go, like, buy meetings with people if you want to build pipeline, you could be like, hey, here’s 100 bucks. Come meet with me. And it kind of didn’t work. We had to pivot the company. And when we pivoted the company, I’m like, I really don’t want to use request for meeting. It’s too hard to remember.

0:04:29 Ryan O’Hara: My brother kept calling it Quest Meet. Like in my family dinners and stuff, when I’d go get dinner with my mom, I’m like, that’s bad branding if my own brother can’t remember my company. So I started trying to come up with a better name. I tried to think about, like, what’s something that brings people together because we’re trying to bring buyers and sellers together to at least exchange conversations back and forth.

0:04:49 Ryan O’Hara: And one of the things I kept thinking about is like, in New Hampshire growing up, like every weekend I’d be going to a different bonfire, but unfortunately bonfire is already a company name. And then I started to mesh words together. And pitchfire was the one that kind of was like, oh, this makes a ton of sense. And it kind of like just when I said it, like, if I felt like I had an out of body experience, like, holy crap, that’s the brand, let’s go. And I had to. I ended up actually, for people listening to this that want to update their domain name, I actually had to lease the domain name. So I didn’t own it for the first year. I rented it from somebody that owned it. I was like, hey, can I pay you a monthly fee to borrow the domain since you just have it parked and when I have money, I’ll buy it. And we bought it when we raised money a couple years ago.

0:05:33 Taylor Wilson: I was just doing domain searches the other day for a client that has a new startup and that’s, that’s a whole thing trying to get like the right domain. It’s rough. It’s rough out there.

0:05:45 Ryan O’Hara: It’s. If you want a dot com, you’re going to be spending a lot of time looking. It’s funny, I have a friend that rebranded his company and he just picked like, he just went to the marketplace and was like, yeah, that’s our company now. And now that they like completely pivoted, it’s like a made up word.

0:06:01 Taylor Wilson: Okay, so. And it was when you were at Lead iq, that was when I first came across you, I think on LinkedIn. And I just thought you were really fun, funny and smart.

0:06:09 Ryan O’Hara: Oh, thank you, thank you.

0:06:11 Taylor Wilson: And then when we were both at the Drive event last year in Vermont, that’s when we met and I was like, you, you. I’ve been following you.

0:06:20 Ryan O’Hara: It’s kind of funny because, like I left the Drive event actually kind of, I went As a student. So like someone gave me a pass to go for free because I miss signing up. And for people not knowing we’re talking about. Dave Gearhart’s Exit 5 community did an event called Drive. It was, it was really awesome. I totally want to go next year too. But I went as a student and I saw a bunch of people there that like, recognize me or like, where have you been? And I was like, crap, I’m doing a bad job marketing pitch fire if they don’t know where I’ve been. Which made me like super self conscious and start thinking about like, I need to up my marketing game more.

0:06:53 Taylor Wilson: It happens. We are, I’ve been there. In fact, like, I go through ebbs and flows, you know, and I’ve been through those ebbs too, where people are like, where are you? I haven’t seen you in a while. Are you okay? And I’m like, I just haven’t been.

0:07:08 Ryan O’Hara: You know. You know what the problem is for me is like I went from working at a series B startup. I climbed up on LinkedIn because I did video really early. When they first came out with video, I, I requested beta access and I was one. Like it helped me a lot putting LinkedIn videos up. But like, as weed IQ grew and I had 200 people working with me, like, it became a lot easier to like get stuff seen with all the customers that we’re in front of and all the. I’d go to conferences and get coverage and meet people.

0:07:37 Ryan O’Hara: Then they’d add me LinkedIn because I was a recent connection to be on feeds now that I’m like in a small four person startup. Like you’re kind of not. You don’t get that same amplification you might get if you’re at a larger or midsize company.

0:07:49 Taylor Wilson: Yeah, it’s harder. It’s definitely like you’ve got a, it’s a lot of elbow grease for sure. You know, I mean we’re, we’re learning that ourselves. So. Okay, so I want to talk about pitch fire because I explain it to me like I’m a five year old. So tell me what you’re doing. Whole premise of getting paid to be sold to.

0:08:12 Ryan O’Hara: Okay. Wow. Here we go. All right, everyone, so I’ll tell you a little bit of Backstory flashback to 2016 when I was a VP of Growth and Marketing at Beat IQ. One of the things that happened was we used to do this annual state of prospecting. We’d ask our users what their average reply rate was on cold emails and what Their average connect rate was on cold calls. The first year we did the survey, the average reply rate on a cold email was 6%.

0:08:36 Ryan O’Hara: And the average connect rate on a cold call was 10% in 2021. The last year that we did it, we had thousands of people take this thing. The average reply rate on a cold email was 0.7% and the average connect rate on a cold call was 3%. So I just saw this and was like, holy crap. We can’t keep depending on inboxes and phones as a way of getting in front of someone and trying to build pipeline. And so I started to think about like, well, how do I get people to, you know, build pipeline with strangers if they don’t know them? And I started to like jam around these different ideas and one thing fell into another and we kind of discovered this concept that I call paid prospecting.

0:09:13 Ryan O’Hara: And the idea is that you have a more efficient, ethical and cost effective way for you to get in front of somebody by compensating them to engage with your sales team. It’s not paying for a meeting. We tried that. It doesn’t work. If you want to ask me that, I can tell you about that story. It’s paying for a response. Paying someone to give your response to your sales pitch is like the exact sweet spot that works. And that’s what we’re doing at Pitchfire.

0:09:37 Ryan O’Hara: We allow you to deploy paid prospecting across your go to market function. Anywhere you are. If you’re in marketing, you can do it. If you’re in sales, you can do it. If you’re in demand gen, you can do it. We have something that makes it really easy for you to go do paid prospecting.

0:09:50 Taylor Wilson: Okay. So like I could, okay, let’s break it down on both sides. Yeah, I’m the company wanting to sell, wanting to prospect. Yeah, there’s have an account with you. And everyone who takes a meeting with me, I’m paying them.

0:10:08 Ryan O’Hara: No, you’re only paying them to respond. So that’s the way we get around some stuff. The reason we actually started as a paid meeting platform where you could go buy meetings with people. And what we found out is it doesn’t work. If I paid $200 for someone to take a meeting with me five minutes in, they’re like, oh man, this isn’t a fit, but I gotta hang out for another 25 minutes. And then a lot of them will be afraid to tell you they’re not interested because you paid them.

0:10:33 Ryan O’Hara: And then the account executive, the same thing happens. They’ll know it’s a bad fit, but they hang out for another 20 minutes because they like, well, my marketing team paid for this lead. I should make sure I do the full pitch anyway, just in case. And what we ultimately found is that buying meetings doesn’t work. The sweet spot is paying someone less than what you pay for a meeting to get them to just respond.

0:10:55 Ryan O’Hara: And so if I pitch you, let’s say you’re someone I want to pitch. I send you a pitch in pitchfire. You can tell me whether you’re interested or not. If you’re interested, you book to start a conversation with the person and it links right to your calendar. If you’re not interested, you give me a reason why and I can move on to a different deal. And now I don’t have to go chase you for another three months trying to get a response.

0:11:14 Ryan O’Hara: The idea is that you pay less for a response, but, you know, one in three of those will actually turn into a meeting.

0:11:20 Taylor Wilson: Okay, okay, so the person. Okay, so the person on the other end, let’s talk about them. Like the people getting pitched or responding to pitches. How does that work exactly? Like, how do you.

0:11:33 Ryan O’Hara: Yeah, so there’s kind of four ways that you can do it on pitchfire. The first way is let’s say you do a marketing webinar or something. Like, do you guys ever do webinars or anything like that?

0:11:42 Taylor Wilson: I have done a lot of webinars. Not lately. We need to. Mostly we just do this podcast right now.

0:11:47 Ryan O’Hara: Me, me too. I need to do it, too. A lot of the time when companies do webinars, they default. We’ll just send a thank you email with a recording. And what we recommend you do instead is take the attendee list of people that go on the webinar. In the webinar, be like, hey, listen, we’re going to send you a paid pitch on pitchfire. After this webinar, go in and tell us whether you’re interested or not. If you are a book with our sales team. If you’re not, you tell us that you’re not interested. I can use that for lead scoring and know that you’re not interested and collect the information on why you’re not interested. Or.

0:12:18 Ryan O’Hara: And you can actually just go make a pitch and then send that link out to people in your marketing database that have registered for stuff. And we recommend running this because even if you get. I’ll give you an example. I did a webinar with someone that had 200 people go to it. I yielded 24 responses, and 12 of them booked meetings with me, and it cost me $25 a pop to get a meeting. Basically, I’m sorry, $50 a pop to get a meeting, because half of them said they weren’t interested.

0:12:43 Ryan O’Hara: But, like, you could go deploy this as part of your marketing arm. And these people don’t need to be in pitchfire to do it. Now, if they answer your pitch and receive payment for answering that pitch, they automatically get added into our marketplace. So we have about 2,600 people right now that work in B2B that you can literally go in and just directly pitch because they’ve answered a pitch before for money.

0:13:05 Taylor Wilson: And how much are they getting paid? Like, 25. Like, on average, like 25 bucks per request.

0:13:11 Ryan O’Hara: So when we. When you send a pitch to someone, I tried to set it up kind of like Google AdWords for people that aren’t familiar with PPC or digital ads and stuff. You set a budget, and then you can bid for how much you want to get to get in front of that person. And you go up against all these different companies. Pitchfire works the same way. When you send a pitch to someone, you could choose from $25 all the way to $2,000. How much you want to get, pay them to get a response.

0:13:35 Ryan O’Hara: And if you pay more, you end up at the top of the inbox. The average person on Pitchfire makes about $63 a pitch right now. So people. Some people will go over a good example, like, I’ll get a client that if they close someone, they get $25,000 as a baseline annually. So they literally will pay $300 to get a response because it’s worth it to them. But if you’re a smaller company that doesn’t have that kind of retainer or a big contract value, you can offer less, and you can still get a pitch in. But most pitches start at $25.

0:14:03 Taylor Wilson: Do you see people, like, doing this as a side hustle? I just have to ask, like, is it something where, like, marketers will be like, oh, I can just, like, get pitched and, like, money side?

0:14:14 Ryan O’Hara: Yeah, I mean, absolutely. But the thing is, you’re still getting the achievement that you want as a salesperson or a marketer. I mean, I. I pay. The average company will pay $3,500 to get book a conversation with the person that’s the decision maker. If they’re in B2B, you start doing the math. Out on our platform, if you send three pitches, one will turn into a meeting. One in three will turn into A meeting, one in three will not respond, and one in three will say they’re not interested and tell you why.

0:14:38 Ryan O’Hara: If you start doing the math out there and you take the $63 average pitch about, you’re literally paying $180 to produce a meeting on PitchFire. That’s a steal compared to some of these other things you use. If your company wants to run paid prospecting campaigns, we can also. You can go give us a target account list of contacts and people that you’ve been trying to break into, and we’ll go run campaigns with them offering the money to answer a sales pitch for you. And if they don’t, we do this for free.

0:15:03 Ryan O’Hara: The only time you’ll pay money is if the person gets back to you.

0:15:06 Taylor Wilson: So you help companies, you help brands get in front of the right people.

0:15:11 Ryan O’Hara: Yeah, we can. We’ll. We’ll coach people on what to say in their pitch, what target audience to go after. I’d like to eventually get to a point where I have enough data where I can be like, hey, these are some target accounts we think you should go after, but we don’t have that yet. We’re still, you know, we’re still in year two of doing this, so. But the concepts here are like, it. Think of it like another channel. You go and put budget toward paid paid marketing and Facebook ads and LinkedIn and Google Ads and all that stuff. And then you have your SDR team doing prospecting. We’re not telling you to stop doing those things. What we’re saying is this is a third channel that we can run for you to go get extra prospecting leads in. And even if the response rate is low, let’s say we go run these for people that aren’t in pitchfire, and we only get a 1% response rate.

0:15:54 Ryan O’Hara: If you have a list of two or three thousand people that we’re reaching out to you every week for you, we’re literally talking an extra one or two meetings a week. And it doesn’t cost you anything if they don’t. For the other ones that see your pitch.

0:16:04 Taylor Wilson: Yeah, I mean, that costs less than a lot of LinkedIn ads. Like, when you look at the.

0:16:09 Ryan O’Hara: You know, because we’re running it on email, the targeting audit is literally better than anything else that’s out there. Because you run a LinkedIn ad and you might be like, oh, I want to go after CMOs of Fortune 500 companies at this target account list. LinkedIn’s still going to deliver ads to people that don’t work at Those companies, if someone’s a product advisor for a company or something like that, this is true.

0:16:31 Ryan O’Hara: The person seeing your pitch is literally the person you’re trying to get to see your pitch.

0:16:36 Taylor Wilson: Okay, so I remember the question, so what’s in a pitch? Is it just like a short, like 90 second video, sent an email or what?

0:16:43 Ryan O’Hara: Right now it’s a thousand character text based pitch. But we have some new features coming out, we have video. You’re going to be able to put attachments in this stuff. The hard part for us is we want to try and make sure that we don’t make a pitch too hard for a prospect to look at or they won’t respond. We’re trying to figure out the right balance there and we’re doing some tests and talking to users right now about it.

0:17:07 Ryan O’Hara: One feature that is really neat that we’re working on right now that’s been coming up a lot is a new view called Conversation View. And the idea will be like, if I go pitch you and you respond and say, yeah, I’m interested, let’s talk. One of the things that we’ve kind of discovered recently is about 45% of decision makers and companies are introverts and don’t actually feel comfortable going on a zoom with a complete stranger they’ve never met before.

0:17:29 Ryan O’Hara: So in the past a sales rep would be forcing these people to go on calls and they really don’t want to, especially if you sell to IT or data center operations people. These are people that literally his light and hide in like caves and work on servers and stuff. The last thing they want to do is talk to a salesperson. Conversation View, what we’re going to do is you pay to get the answer from the person and that person can opt to start a conversation with you every 30 days, will recharge you to keep that conversation open so you don’t have deals go close cold and just ignore you.

0:17:58 Ryan O’Hara: And that person the buyer has to keep in response to you every seven days. And if something auto not respond, it automatically archives the pitch and will kill it and you don’t get charged the next 30 days. So we’re trying to build a little bit of this model where like you don’t just prospect on pitchfire, you can redo all your communication with the person you’re trying to pitch on there.

0:18:18 Taylor Wilson: And is there like CRM integration with that or anything like that, or is that on the horizon?

0:18:23 Ryan O’Hara: Not yet. Yeah, not yet. We are working on a HubSpot integration and we’re playing around with A Salesforce integration. I think part of the reason that we haven’t done this part yet is because those systems rely on email addresses and we don’t use email. So, like, anything that you do on pitchfire is done on pitchfire. Your pitchfire link is almost like an access point, like an email address or a phone number.

0:18:45 Taylor Wilson: It’s almost more like, in a way, it’s not like a community, but like, in a way it’s sort of.

0:18:49 Ryan O’Hara: It’s got some vibes. It’s got a little bit of like, I’m going to play hacky sack before class for five minutes with my friends. There’s a little bit of that.

0:18:56 Taylor Wilson: All right, so you were telling me about category creation, that being a bit of an offering you have or something that you’re working with your clients on. Tell me more about that.

0:19:07 Ryan O’Hara: So a lot of people that try and get companies to go and get traction and get awareness, it’s really hard if you have a bunch of features and it’s really complicated. And what we’ve been doing at pitchfire is I used to have to peddle people on this B2B marketplace with buyers and sellers. And then, by the way, we also have Inbox plugin and Chrome plugin you can use where, like, if someone prospects you and you want to send them the pitchfire, you can reply back in one click with our Chrome plugin and direct them there.

0:19:36 Ryan O’Hara: The problem with all this stuff is it’s so complicated. And so when I went to the Exit 5 event, it kind of inspired me to think about doing this, deploying a category creation playbook. And if you’re new to marketing and you don’t know what this is, the idea is that you sell people on this new world that’s happening and your company is a new category. In our case, pitchfire is a paid prospecting platform.

0:19:57 Ryan O’Hara: The category I’m trying to sell you is this new channel called paid prospecting. And you could be a prospect that gets paid from paid prospecting, or you could be a buyer or, sorry, a seller that’s paying people on paid prospecting. I’m selling you on the importance of this category. Instead of leading and selling people on pitchfire and all these bells and whistles and features, I’m selling you on this world that paid prospecting’s in. And the reason it exists is really important because today it takes 220 actions for someone to get a positive response from a prospect on pitchfire. It takes three.

0:20:30 Ryan O’Hara: That’s because of paid prospecting. You’re creating more Incentive for someone to get back. If you want to do this stuff, the framework is pretty simple. You need to not sell your product. You’d sell people in the category you’re making.

0:20:40 Taylor Wilson: How did you define your category and, like, what recommendation do you have for people when they’re maybe going down the lane of category creation?

0:20:50 Ryan O’Hara: Yeah.

0:20:50 Taylor Wilson: So creation, by the way, like, this is one of my favorite topics.

0:20:54 Ryan O’Hara: Me too. Me too. I think a lot of companies do it when they shouldn’t. Like, we actually, like. I remember there was a point at Lead IQ where, like, the exact team, we were all doing, like, huddles and be like, can we make a category? Could it be a category? And I’m like, I feel like we’re forcing it. Couple situations that make you do it is, like, if you have a product with a bunch of different features that are, like, hard to describe, it might be a fit.

0:21:16 Ryan O’Hara: The way we came up with the idea of paid prospecting is around November, I started to notice that people were posting on LinkedIn and tagging me on post anytime that someone did a post about, like, adding a charge. Like, you can add charging to your calendly. So, like, you could make a calendly and be like, hey, you need to put a credit card in to meet with me. If another. There’s another company, like, there’s a company called Intro that, like, you can pay someone money to go take a meeting with them for advice.

0:21:43 Ryan O’Hara: And what kept happening is I kept seeing people tag me on these things because the thing they’re connecting with pitchfire and recalling was this concept of, like, paying someone for their time, whether it’s time to write a response or something. And so I started to see that. And the area that we’re kind of trying to control is everything before someone becomes a customer. So that’s prospecting. We took the words out of people’s mouth, and now we’re doing paid prospecting. It’s just channel. And honestly, it’s been working so well.

0:22:10 Ryan O’Hara: It’s so much easier to talk about pitchfire on these calls with people. And when I get on sales calls, my sales team’s using the exact same language that I am. And it’s because of that category creation. Everybody’s bought into this category. It’s just a question of teaching people in the world the gospel of this new category.

0:22:27 Taylor Wilson: I like it. I like the name of yours. I’ve been trying to. I’ve been coming up with ours, and I think I’m at a point where I’m about ready to start talking About a lot more.

0:22:37 Ryan O’Hara: Oh man. I want to grill you and ask questions but I don’t want to make you spill beads if you’re not ready.

0:22:41 Taylor Wilson: To can grill me.

0:22:43 Ryan O’Hara: So what are you doing? What do you think about what are you playing around with for a category?

0:22:47 Taylor Wilson: So at first I started talking with Creative Shizzle when we launched our design on subscription service. Really thought about it as design on demand. But we are about to launch a content marketing like writing platform into the design services that we provide. And so I’ve really been thinking about it as creative on demand or content on demand. But I really think it’s creative because it’s basically like if you are a small team and you don’t have the bandwidth or the in house support, you don’t want to like deal with managing freelancers and posting jobs on prep work and stuff like that.

0:23:28 Taylor Wilson: You could just come to us, have a subscription and you have creative on demand at all times.

0:23:33 Ryan O’Hara: Yeah. So. Well, it’s good. Well I’m not, it’s not the actual idea I want to poke holes on for the people listening. I want to like help them with like how to think about it with positioning. Right? Yeah. So there’s a bunch of companies that are out there that have done this before. The most popular one that we both are probably familiar with that like because we were at exit 5 was gear arts company Drift.

0:23:53 Ryan O’Hara: I’m sorry, I’m going to rip the band aid off and be blunt. Drift is literally identical to Intercom qualified live person. There’s like 90 companies that were all doing chatbots on websites. But what Drift did is they went to marketing were like oh it’s not a chatbot. We, we are a conversation marketing platform and we have a bunch of tools that make it easy for you to deploy a conversation marketing channel in your company.

0:24:17 Ryan O’Hara: That’s a no brainer. It’s so much easier to sell. And the other thing it is is it’s contagious because you can go to a, into a sales meeting with someone and instead of getting in a bake off with someone like Intercom and being like we have this feature, they have this feature. What you can do instead is you can go into the meeting and they can be like, hey listen, all these people that are coming to your website are millennials.

0:24:41 Ryan O’Hara: They’re the ones that are going to be making decisions and signing contracts with your company. Now guess how millennials communicate. Text message chat. They grew up with AOL and Messenger. They grew up with imessage, they grew up with talking to People over chat, they use slack at work every day in Microsoft Teams. They’re not hanging out and going through and like filling out forms and going and hanging out in their inbox all day. In fact, the average person that’s a millennial spends less than three hours a day in their inbox versus 10 years ago, it might have been 20 hours a week that they’d be in their inbox.

0:25:12 Ryan O’Hara: See that story? I’m able to tell that. And I don’t even work at drift. And that’s because they’re selling you on this world. Like for me, I’m going to people and saying, hey, the average company spends $3,500 to produce a meeting and the average company at 80% of them are missing their pipeline goal. What’s causing that? Well, people don’t want to respond to cold calls and cold emails anymore. They’re sick of it. There needs to be more incentive.

0:25:34 Ryan O’Hara: How can I prove that? Look at all the side hustle and gig economy. How many people have more than one job or other posts on LinkedIn. Like, 40% of the US economy is on is 1099. Now I can tell all these stories about this, these trends in this world happening and saying this is where it’s going. You need to be in this world or you need, you’re going to be left back. And so you could, you want to do the same thing.

0:25:56 Ryan O’Hara: One of the classic sales techniques that they talk about with, like, there’s a really famous framework called Challenger that like people talk about. Like, you need to give people insight on a problem behind the problem. So like, if you can do that in your pitch, like, I don’t go to people and say, like how to go to people and say 80% of companies are missing their B2B pipeline number. That’s a problem.

0:26:18 Ryan O’Hara: But I’m going to tell you the real problem behind it. It’s that 40% of that is supposed to come from outbound prospecting. And the roads that we use to prospect people are broken and don’t work anymore. Now I’m going behind that problem and peeling back all air. So for you, when you talk about this and you’re doing the category creation, let’s say it’s on demand content, you might talk about, like, I’ll give you a really good example actually, you could steal this. Feel free to steal this.

0:26:41 Taylor Wilson: Probably will.

0:26:42 Ryan O’Hara: Marketing today is about quantity, not quality. And if you go back 10 years ago and you worked in a marketing department, you might put one blog post out a month and you might do A video clip. You might make a bunch of clips and throw them on YouTube, but usually we put the full episode. Today it’s the late night show. I actually, someone at the Exit 5 conference called it Broadway. I was kind of upset because I always tell people it’s like a late night show.

0:27:10 Ryan O’Hara: Johnny Carson, Conan O’Brien, Dave Letterman. I won’t say Jay Leno because I don’t like Jay Leno. Those guys had to do a show four days a week, no matter what. If they were sick, they didn’t feel well, something had to come out every day. That’s what marketing’s like today. And if you’re not doing that, people will forget you. It takes 14 to 26 touches to get someone to look and remember your brand.

0:27:34 Ryan O’Hara: So if you’re not creating excuses to make those touches because it takes too long to execute, you’re going to be screwed. That’s where you come in on demand. Content creation. I’m making that up. Maybe it’s wrong. I don’t know. I’m just.

0:27:45 Taylor Wilson: This was good. I should have talked to you sooner, Ryan.

0:27:50 Ryan O’Hara: Oh, it’s okay. No, it’s okay. It’s okay. But I’m just saying, like, I might.

0:27:53 Taylor Wilson: That you’re going to see this. Our marketing now. It was great. Thank you.

0:27:57 Ryan O’Hara: Yeah. So it’s.

0:27:58 Taylor Wilson: But you find anyone listening some things to think about? Absolutely, yeah.

0:28:03 Ryan O’Hara: Anyone listening to this. If you want to do that, you have to pour on problems you’re not thinking about and it might not relate directly to your product. It’s something a little bit further back.

0:28:13 Taylor Wilson: So it’s not even so much like, are you. I really like what you. All the examples you’ve given around, like insights and trends and numbers and statistics. Because I think a lot of times I’m even thinking about directly connecting to the person I’m talking to. Like, do you feel like you don’t have enough time in your day to do all of this? Like, are you feeling, you know, strapped for time? Blah, blah, blah. But it’s really like you’re saying it sounds to me like create this bigger macro problem.

0:28:41 Ryan O’Hara: Yeah. The one that I always love people talking about as sucks because everyone’s going to hear this and roll their eyes because they’ve probably seen it. But like, there’s a guy named Andy Raskins who, like in 2012, wrote a blog post called the Greatest Sales Deck I’ve Ever Seen. And he talks about Zora, the billing subscription company, going to market and disrupting the billing subscription market.

0:29:02 Ryan O’Hara: But they became like the big company that does all the billing and stuff for all these B2B SaaS companies. And the reason they did it is they went to companies and sold people on the idea of why you need to turn into a subscription business. And they this is how you have an impact. I used to buy Adobe Premiere to do video editing and I’d pay $700 and I’d have it for four years. And then every four years Adobe would have to get me to come back and rebuy the software and not switch the final cut. Microsoft did the same thing with Microsoft Office. You’d go buy Office for three or four hundred dollars and keep it for a long time and then they’d have to re chase you to upgrade and make sure that the product was better. Zora went to those companies and said, hey, people are moving to a subscription economy. They did it with cable, they’re doing it with Netflix, they’re doing it with Amazon.

0:29:49 Ryan O’Hara: If you don’t have a subscription business, you’re going to be left back. And instead of fighting to get these people back every three or four years, you can have them stay with you for 20 years instead and make more money. Give them gradual releases and it changes the whole philosophy of a company. Zora did category creation. That’s they, they sold people on the subscription economy. It’s the same thing. You got to peel back that problem.

0:30:12 Ryan O’Hara: But the biggest reason you want to do this, Taylor, and anyone listening is because if you do this, it’s contagious. If you tell me a compelling pitch, I’m not the buying committee today is 12 people in a company. It’s not one person. They need to go talk to other people. And we’re not in desk anymore. Like where I could go pull someone in, be like, hey, come sit on this call. A lot of us are remote.

0:30:34 Ryan O’Hara: You want to get someone to tell, talk about an idea you’ll get out of a call. What are you going to do? You’re going to go hop on Microsoft Teams and be like, I was just talking to Taylor. Holy crap. We’re not putting content out often enough. It’s or we are, but it’s taking way too long and it’s too challenging. Maybe we should shift and think about using creative shizzle on demand content creation platform to really level up our marketing game and make it more about quality as opposed, I’m sorry, quantity as opposed to quality.

0:30:59 Ryan O’Hara: Now I’m grabbing my popcorn and I’m listening.

0:31:01 Taylor Wilson: Yeah, and you’re gonna just like email, you’re gonna slack that around Teams it around. Hey, go check out this link. It’s not necessarily gonna be that like, big buying committee all at the meeting at the same time. That’s a really good point.

0:31:13 Ryan O’Hara: Yeah, so that’s. That’s kind of like, for us, we’re doing that with paid prospecting now. And I looked at other companies. I went and looked at what drifted on there. We just redid our website, we redid our pitch deck, but the messaging is consistent across the board. And I’m. That’s the idea is like, if I’m all over the place in my messaging on each piece of content, the customer is going to be too. This makes it so that there’s kind of a bible that we can all stick to.

0:31:36 Taylor Wilson: Okay, Ryan, so you are just really passionate about sales and marketing.

0:31:42 Ryan O’Hara: Oh, I love it.

0:31:44 Taylor Wilson: Very forward thinking. And I’m curious what’s on the horizon for sales and marketing in 2025 that we haven’t even seen yet?

0:31:55 Ryan O’Hara: Everyone’s probably expected me to say something about artificial intelligence. I will tell you this. The AI stuff needs to be viewed as a way for you to be more creative. It’s a creative partner. That’s how to think about it with this stuff. And I think that there’s like. I’ll give you an example. I did a video called what is paid prospecting? That I threw up on my website. I wanted to show. I told the story about how 2000 years ago in Rome, people used to have rocks that they would sell to travelers coming through the city.

0:32:24 Ryan O’Hara: And I wanted to make a video of that. And for me to go do that, it. Five years ago at Lead iq, I would have gone and bought a toga. I would have worked out for a couple weeks so that you guys wouldn’t see a flabby man in a toga. But I would have. I’m dropping truth bombs for the people here anyway. But I would, I would have literally filled that B roll and reenacted it then instead, I was able to go into sorrow and put in a prompt to be like, make me a Roman.

0:32:51 Ryan O’Hara: A Roman merchant selling granite and marble at a market. And I threw that in my video. And like, I didn’t have to go and be bogged down with that. We’re gonna need to start thinking about, like, I. I can use this thing for cool, fun ideas. It’s not to replace stock footage. It’s to make your own footage. It makes sense. That’s cool and interesting. We need to think of it like that.

0:33:16 Taylor Wilson: Yeah, I agree with you completely. I think that it’s also, I think it’s a creative partner and it’s like a. An efficiency partner.

0:33:27 Ryan O’Hara: You know, it’s funny, whenever I have a good, like, what I think is a good idea for something, I’ll write it down in my notepad on my phone, and what ends up happening is like, I’ll have an idea and I won’t use it for something, and then I’ll figure out how to use it eventually. And, like, I’ll give you a good example of this. I know when I was at Leadinq, we wanted to break into a bunch of accounts, and I had this idea 12 years before Leadinq of like, what if I grabbed a camera and I serenaded people with a string quartet and, like, filmed videos for them and then emailed it to them and said, hey, we got this string quartet for you. Go watch this video and then customize these pitch videos. It stayed in my notepad for years.

0:34:06 Ryan O’Hara: And then eventually, when I was at Lead iq, we’re like, hey, we want to go get some logo accounts so people trust us and believe in us. I hired a string quartet and we filmed this and we did a bunch of these and we ended up getting like a 60% book rate on meetings doing it. That idea sat on my notepad for 12 years, and the execution of it was kind of hard today. If I wanted to do that, why couldn’t I go grab a string quartet video using a generative AI thing and make a video and then voiceover, my voiceover, and just edit it really quickly in Adobe. Like, these are things that you’re going to be able to do to execute so you can test stuff and it doesn’t have to be as heavy lifting.

0:34:43 Taylor Wilson: Yeah. It’s funny, my son even was telling me this weekend about how he’s like. He’s like, I started a. I started doing video editing last night because I. He stayed up till like 5am on Saturday night, and I was like, what were you even doing? He was like, I started editing video. I’m like, tell me that. He’s like, yeah, I was using cap cut. There’s like this. This meme thing on the Internet with something something and something something. And I was doing this AI voice over, like, Minecraft scenes. And I’m like, hey, good for you. Like, you were. You were practicing a new skill. Like, yeah, and I think there’s going to be so much more of that where you can create something out of, like, very little in terms of, like, the cost or, you know, like the resources that you need.

0:35:27 Ryan O’Hara: It’s funny when I. I go back and I think about, like, I learned how to video edit because I skateboarded. And I wasn’t that kid. I was the kid that didn’t get better. And everyone else around me got better at skateboarding. So I was like, well, I need a way to hang out with my friends, so I’ll buy a camera and I’ll film them. And then I started buying editing gear and I’d film my friends skating. And then I’d cut videos and put them together online and throw them up. And then YouTube came out. That changed everything, too.

0:35:50 Ryan O’Hara: But, like, I didn’t think that I was getting a PhD in content creation skateboarding with my friends when I was 12 years old or 13 years old, but I was. And, like, my friend John and I did a podcast about Goodfellas, like, a movie that we both loved. Like, in 2002, before there was even podcasting, not knowing what it was, we were like, let’s just record ourselves talking about Good Fellows. We didn’t host it. We never put it online.

0:36:15 Ryan O’Hara: Thank God no one saw it. But, like, create. Like, if you can create stuff, you get really good at it the more that you do it. Don’t overthink stuff. Just try and get stuff out every day, even if it’s bad. Like, get stuff out every day and you’ll get better at it organically.

0:36:29 Taylor Wilson: All right, I’ve got one more question. How are the dogs you’ve got? Don’t you have three corgis?

0:36:35 Ryan O’Hara: I do. I. I’m carefully upstairs so they wouldn’t be barking because I wanted to do this for my desk downstairs, but I was worried it would be too loud. They’re meant to be herding dogs. So, like, if you stand up for any reason, one of mine, Arwen, is so smart that if I were to say goodbye to you on a zoom call, she’ll get up and come to my feet because she knows I’m going to get up to, like, either go to the bathroom or get coffee or get a drink. She’s ready to come herd me to the. To the kitchen while I’m grabbing a drink or something.

0:37:02 Ryan O’Hara: They’re doing pretty well. The only problem is my wife and I were cutting one of ours, Ruby’s nails, the other day, and we cut the nail too short. And if you. This is useful for dog owners out there. If you ever cut the nail too short, the dogs have a thing called a quick. And what it is, basically, is a dog nail is actually connected to the bone of, like, like, it’s a bone. It’s connected to the bone. It’s not like a fingernail on a human.

0:37:24 Ryan O’Hara: We cut it too short and she just started bleeding everywhere. Like, oh, my God, what do we do? And, like, we put pressure on it and stuff. If you ever do that, you can use flour to stop the bleeding. That’s the life hack. Like, they bleed a lot. It’s usually okay. It’s not an emergency. Yeah, you use flour, you can stop the bleeding. Another one is cornstarch. They make stuff just to stop the quick. But anyway, we’re probably never going to cut our nails again.

0:37:47 Ryan O’Hara: Too scary. Too traumatic. I’m done. I’m done. I can’t do it.

0:37:51 Taylor Wilson: Dramatic. After that, I started only having the dog groomer, like, do the nail trimmings.

0:37:57 Ryan O’Hara: Because our problem is too. Yeah, our problems are dog groomers, like, booked out nine weeks, and they don’t cut them that short because they don’t want to cut the quick. So, like, the cycle of it, we’re like, it’s. We got a crazy snowstorm here, and I’m like, oh, I got to figure out how to, like, let her walk on the snow without her nails getting hitting her pads and hurting her. So.

0:38:14 Taylor Wilson: Yeah. Well, Ryan, this has been great. Thanks for coming on. Thanks for workshopping some stuff with me.

0:38:19 Ryan O’Hara: And we talked too long, didn’t we? We blew it. We blew your podcast format.

0:38:24 Taylor Wilson: Stop echoing.

0:38:25 Ryan O’Hara: At least I think so. I think so.

0:38:28 Taylor Wilson: Okay, But.

0:38:28 Ryan O’Hara: But anyone listening to this, Taylor’s voice will be echoing in your mind for years. Think about it. Creative shizzle, shizzle, shizzle.

0:38:36 Taylor Wilson: You’re welcome. You’re welcome. Well, Ryan, if people want to get in touch with you, follow along. Find out about pitchfire. Use pitchfire. I think I want to use pitchfire. So I’m going to talk to you about that to find you.

0:38:49 Ryan O’Hara: If you go to pitchfire.com we have two buttons on there. One’s for buyers to sign up and use our plugins to send salespeople pitching you to pitchf. The other button will take you to a meeting directly with me. I will tell you how to deploy a paid prospecting strategy across your marketing arm. Follow me on LinkedIn if you want to see content that we do like we were talking about earlier, I probably put three or four videos out a week now.

0:39:08 Taylor Wilson: Yeah, I like. Your videos have come back. You’re. You’re on fire.

0:39:11 Ryan O’Hara: I’m getting back. I’m getting back to it. You know, it’s hard to do a video when you don’t have a good website to send people to, and that was something we had to really work on. I want to give a shout out to Sahil Patel from Spiralize who, like, inspired me to redo our website because he does this great show. You should, Taylor, you should probably go on it. You’d be great on it. He does this show called Sahil Patel. He does, like this thing called CRO Crimes and they do a game show where they go through a bunch of landing pages and talk about what’s better and which one’s better against someone.

0:39:42 Ryan O’Hara: And I did it as a contestant and I saw these landing pages and all his critiques and I’m in the episode. I just posted about it. I posted the episode yesterday. But I’m in my head, I’m like, oh man, our website sucks. I need to fix our stuff. It inspired me to level up a little bit. If you’re looking for some great content, I’d recommend that. Yeah. Well, thanks for having me on. I really appreciate it.

0:40:03 Taylor Wilson: Thank you. Okay. And I hope this was helpful to everyone listening today. And until next time, go get all your good shizzle done.

0:40:16 Taylor Wilson: Well, hey there. That was fun. I love how much mind blowing and mind openening shizzle our guests bring to us with every single episode. We hope you enjoyed the conversation as much as we did. Make sure to hit that subscribe button on your favorite podcast player so that you don’t miss a beat of the Talking Shizzle podcast. And if you’re listening on Apple, be sure to let us know what you thought and leave us a review we’d love to hear from our listeners so that we can bring you all the good, juicy business growth shizzle that you’d like to hear about.

0:40:53 Taylor Wilson: Be sure to get in touch with us and follow along creativeshizzle.com or shoot us an email at hello @ reativeshizzle.com now, until next time, we hope you go get your big shizzle done.