Step into the high-stakes world of freighttech sales strategy with Ryan Sullivan, a pro at creating sales teams. Ryan's sage advice on creating a go-to-market strategy that's as precise as a poker player's calculated bluff. As we shuffle through the deck of scaling intricacies, from constructing the perfect customer profile to navigating the chaotic tableau of business growth, Ryan deals a hand that is sure to set you on the path to success.
Thanks again to your our sponsor, GoPayhawk. Stop overpaying and start thriving with GoPayhawk's payment process solutions. Visit GoPayhawk.com today and use code TLS24 to learn more about receiving a $250 credit on your payment processing solutions.
Step into the high-stakes world of freighttech sales strategy with Ryan Sullivan, a pro at creating sales teams. Ryan's sage advice on creating a go-to-market strategy that's as precise as a poker player's calculated bluff. As we shuffle through the deck of scaling intricacies, from constructing the perfect customer profile to navigating the chaotic tableau of business growth, Ryan deals a hand that is sure to set you on the path to success.
Thanks again to your our sponsor, GoPayhawk. Stop overpaying and start thriving with GoPayhawk's payment process solutions. Visit GoPayhawk.com today and use code TLS24 to learn more about receiving a $250 credit on your payment processing solutions.
And welcome to episode six of the Last Sell. I'm Kevin Hill, your co-host up here, along with Richie Daigle, as always as we talk to industry leaders about sells, and today we have a very special guest for you. It is none other than Ryan Sullivan. And Richie, tell me a little bit about Ryan. You used to work with Ryan, right.
Speaker 2:I did. I did Ryan. He hired me when I was at Tide, so he was my boss and, yeah, so Ryan is a poker player. He's very strategic in nature, very thoughtful when it comes to sales and, yeah, this is a great episode. I think his specialty is startups and helping companies scale and get the snowball rolling, so to speak, and you see, all kinds of really interesting stories come out of the startup world. And boy did he have some interesting stories to share in this episode.
Speaker 1:He did this episode. It did you know? It's that startup sales process going from no processes or procedures, or sometimes not even a crm, to something that is is grounded and scalable, and uh, it's it's interesting journey as you go through that and we relate it as much as we can back to card playing, because it's all strategy and strategy is strategy is strategy, whether um it's business strategy, chord strategy, chess strategy, um baseball pitching strategy, it doesn't really matter, it's all a game of cabin pounds it is and it's strategy in the midst of a mess is a lot of times startup and poker for that matter.
Speaker 2:You can have a poker table where everyone's like 7-2 and I'm all in, what are you going to do about it? And it's just chaos. And there's a messiness and a chaotic nature to the startup world as well, where you have a great product and you don't understand why everybody isn't buying it immediately. Great product and you don't understand why everybody isn't buying it immediately. And you're trying to figure out how to qualify people and how to build pipelines and how to build a go-to-market strategy and all these things.
Speaker 1:And ICP is a big big thing for today too. Building your ICP, or ideal customer profile, and some of the dangers of not doing that.
Speaker 2:And how to gently tell somebody that let's be all things to all people and why that's a bad idea Ninety nine percent of the time. You know it's it's. There's a lot of interesting things that come out of the startup land as well as out of poker, and the stories Ryan had to share were were, uh fantastic, and I think some of the, the directions that he took I didn't see coming, you know so it was definitely.
Speaker 2:I think there's gonna be some curveballs that uh catch people off guard a little bit in this one yeah, so and and let's uh, you know shout out to our sponsor go pay hawk.
Speaker 1:So if you process credit card transactions, if you have a need for that a lot of times, getting money in the door today is fantastic. So if you need invoices to be paid, having a credit card payment processing service is key and essential. And if you go to gopayhawkcom, you can catch all the deals and benefits there. I think they're offering a $250 credit after 90 days for getting set up with them. So go out, check out gopayhawkcom. But with that said, without any further ado, let's go straight to the interview let's get into it for our listeners who are joining here.
Speaker 2:Uh, we have ryan sullivan on today. Uh, who has quite the the extensive career in sales, and ryan, um, yeah, maybe a quick introduction for people who don't know you like, who are you, what do you do, and um, and we can go from there yeah, so my name is ryan sullivan.
Speaker 3:I live in boston, um, so I've been a founder twice. Now I'm currently running a consulting firm focused on early stage supply chain tech companies and trying to leverage the experience I not only have as a founder but as a three-time head of sales to basically distill down what's great about how founders sell, which often is not best practice oriented. It's through domain expertise and excitement and the fact that people know they have the juice to make things happen and distilling that down into processes for companies that are hoping to scale up. So I was responsible for SMB and mid-market sales at Cubix on a 10x four-year run, and then I was responsible for sales and go-to-market at Tive through a 6x 18 months. So just trying to sort of boil that down and leverage that framework to help companies scale up in a time where funding and true revenue is much more important to investors than it may have been previously, it really is important right now, especially in this environment.
Speaker 1:This VC funding is sales customers revenue. It's much more important than it was a couple of years ago. I mean, it's always important, but now everyone's talking about profitability, about growth as well. But getting customers in the door is not always about building the tech. It's about selling the tech now.
Speaker 3:Yeah, absolutely, and a lot of the people I'm talking to now.
Speaker 3:Having been a founder and, Kevin, I know you have as well when I thought about the venture landscape over the last decade, like after some sort of seed funding, pre-seed funding, it's like get to a million ARR for a software company and then you think you should be able to raise a Series A, and what I'm finding is that's not exactly true in today's market.
Speaker 3:Some of it is because they were overfunded in a seed round and some of it just is because, since there's been less funding, there's a lot more options for investors. That's really one half of what the business is focused on. The other half is just I worked at Tive for two years and when I got there they had a lot of infrastructure set up already, so I didn't have to spend the first six months like trying to build this baseline framework. It existed and allowed me to get to selling and revenue generation more quickly and revenue generation more quickly. So I think having some sort of fractional help for companies in the early stages make it so when you raise the big bag and you get the Series A, you don't hire a super expensive head of sales that takes six months before they're able to really start getting to value adding, Adding value. Excuse me.
Speaker 1:Yeah, you can't really afford it in this adding adding value, excuse me, yeah, you can't really afford it in this market though this market, you have to be up and running and and selling to to be able to, to raise, raise your next round. So I think investors are hyper-focused on on that part of the business right True sales growth, true business fundamentals, I suppose.
Speaker 3:Yeah, and I mean I think like the industry element is just another complexity.
Speaker 3:Like Dan Clark so the founder of Cubix, who really taught me what I know about transportation as I was learning it, I'd be like this does not make sense, that this is how it operates, and he would always say transportation is the oldest industry in the world, say transportation is the oldest industry in the world and the processes were built by C students, because in the 50s, 60s, 70s there's no supply chain degrees in college.
Speaker 3:People come back from the military or they didn't go to college and this is the path that they chose. So it's just, those are his words, not mine. But you know it does add a level of complexity where you see people come in from other industries and it's hard to even understand some of the fragmentation. It's hard to understand that a bill of the carrier versus broker versus forwarder versus asset based broker, value propositions and differences. So you know, I think that that understanding is something that is really important from a go to market standpoint and I've seen a lot of failed attempts of you know more generalists trying to come into the market and or into the supply chain tech market and be successful.
Speaker 2:It makes me think of you know. Tim Ferriss put something on LinkedIn I think, two days ago. I'm just going to read it. He said refine rules and processes before adding people. Using people to leverage a refined process multiplies production, but using people as a solution to a poor process multiplies problems.
Speaker 2:And it kind of speaks to the importance of really refining and building good processes, whether that's a tech stack, whether that's a market strategy, whether whatever it is like, if you can nail that early on, then when you're adding people you're adding leverage Versus if you're just trying to use people as a band-aid, things just get messier down the road, Switching gears a little bit. What is your favorite vacation spot? If Ryan Sullivan is going to go on one last vacation, where is he going?
Speaker 3:I think I would go. So I'm going to say France as a whole. Paris is my favorite city, but I like the culture. I was a history major. The French Revolution is my favorite war, so very interested in that. But both times I've been taking the high speed train to nice as well, um, which is right next to the monte carlo, so go over, get a little poker. Beautiful beaches, incredible food and, you know, really just appreciating the, the culture and?
Speaker 2:and what's your favorite beverage, alcoholic or non-alcoholic? If you have one drink that's your go-to. What are you sipping on?
Speaker 3:From an alcoholic perspective, bentwater Sluice Juice is a New England hazy IPA. Then non-alcoholic I would say Grafruit Perrier seltzer with your pinky up. I'm a volume drinker of seltzer, all right.
Speaker 2:This seems to be a trend. We had Scott Leeson recently and he also talked about being addicted to bubble water. I also share this addiction. Maybe this runs across salespeople in general, but so we're in the future. You have hair again, but you also have a lot of wrinkles. And you're in France. You've just taken a high-speed train down to Nice and they have some kind of way on the train. They had this slush juice just pouring, like everybody was drinking it in the entire train. They're walking all over the place. It was at the casino, at the Monte Carlo as well. They had the grapefruit bubble water. Everybody's got their pinky out. You as well. Here you are and you're older and you realize. Well, and here you are and you're older and you realize I am completely done working. I am retired, I've made my money, I'm enjoying retirement. Now, if you look back on your career, what's the last thing that you sold?
Speaker 3:So I mean my hope would be that it's a company. You know, I think for me, having been a part of two exits, you know the idea, like the stage I usually come in is from a building standpoint, right. So that's like the optimization, many of the processes, the hiring profiles, the systems, they, they don't exist. So to me, the most rewarding part, parts of what it is that I do is, you know, helping to build a company that is so exciting that another company would see the value in purchasing it, and then seeing the trajectory and growth of those that I've worked with. I mean, I think for me, like my coaching tree is like what is most rewarding to me about you know what it is that I do and what I've done, so I would hope it's a company.
Speaker 1:And yeah, nice.
Speaker 2:What if?
Speaker 3:it wasn't a company.
Speaker 1:If it wasn't a company, then I would hope that Maybe the company was the second to last sell Company.
Speaker 3:Well, so then it would be a complicated multi-stakeholder enterprise software deal. I mean, I think from a sales standpoint, the most enjoying deals I've been a part of were at Tive, a part of were at Tive, and it really was just because you know selling transportation management systems so many different departments are involved. You know it's complicated, it's more on the expensive side, so there's more of a need to justify business value and you know when it works. It was the largest tangible ROI generator of any of the things I've been a part of selling.
Speaker 2:Nice.
Speaker 3:Good answer.
Speaker 2:Good, good answer. So if we go back in time, right, so this is your last sale, the fictitious, what could be your last sale? Right, and I love the idea of selling a company, but if we back up, what was the first sale that you've made?
Speaker 3:Yeah. So I mean, like many people in sales, I was a server and worked in restaurants as a hustler and I also sold cell phones and so I'm going to skip the server side of things, I'm not going to count that. So my first sale I worked at an authorized retailer at Verizon, and my first sale was an upgrade of a family of three's cell phones. And I just remember when I started looking at this leaderboard like how are people doing seven, eight, nine, ten upgrades and new lines per day? Like I just did my first one. I'm all excited about it.
Speaker 3:I upgraded, you know, three people's cell phone to the iPhone 4, if that tells you anything about how fast Apple innovates and how long ago this was. But like that's really when I started to feel like I understood sales because this job was at there was four locations in the Hudson Valley, new York. It was primarily in malls, it like kiosks in malls and I just that's where sort of the server experience came together with the cell phone experience to understand that you can't just be order taking, like if you are not asking questions and you're allowing someone to, you know, come to you as the expert and tell you exactly what they need, especially in this time where we didn't have the level of access to information that we may now that it was nearly impossible to be successful if you weren't willing to ask the questions and go deep enough to make a recommendation, versus to just follow what your prospect is outlining. So that was my first sale and that was definitely a lesson sort of that stuck with me over time.
Speaker 1:And it was a lesson of really doing discovery right, of really probing down and being more of a consultative cell than your mechanical cell of what typically you know.
Speaker 3:In a position like that you'd be expected to yeah, well, I mean, there was a lot of elements of it so like. So, yes, that's true, but for example, our compensation. We got paid like nothing on iphone. So we if you ever went into a verizon store and they're trying to talk you out of an ip to get the Samsung Galaxy or whatever it was Like, we got paid tremendously more on that.
Speaker 3:So I was excited about my first iPhone upgrade but it was like maybe a fifth of what I would have been paid should it have been an Android device. And you know, over time I started to realize that, like people didn't know what it was they wanted. They knew Apple was cool, their friends had iPhones, but there was no real reason outside of that that that's what they were coming in and saying they wanted to buy. So you know, if I was able to understand not only their technical footprint like what do you want to do with it, as well as what it is you like to do from a general enjoyment standpoint, then I couldn't make a recommendation to buy something that was not, you know, the flavor of the week or kind of the thing that they've done a great job marketing to make cool.
Speaker 2:It's not all that dissimilar from when you're working in a restaurant, though, right, because I mean I worked in restaurants too, and bars, and I'm sure the people that know what they want. They come in and all you do is you take their order and it's really easy to read that person hey, they're a regular or they're just straight and to the point. There's a lot of people that walk in what do you recommend? What's good here? I don't like they're looking to you for some sort of direction on the menu or through a wine list or through, you know, just building a whole dining experience, and I think you learn a lot in the restaurant world of like how to ask some basic discovery questions.
Speaker 2:What do you like, like, what are the things that excite you? You can build an experience. That skill set is massively important in sales. It sounds like you just drugged. I would imagine you would have been a good server in the restaurant world with offering good recommendations, asking some discovery questions and building a good experience, and you just drug, drug that skill set along with you yeah, yeah, I mean, but I think, like I think that's true, but I think in the moment, at 22 years old, I agree with you, it's very obvious that sort of translation.
Speaker 3:But at 22, like I don't know that, like it, it took me time, I think, to synthesize and sort of digest that and I really don't think it's very different from the world that I'm in now. But you know, I love both and I'm biased because I did both of them. I love hiring people with those backgrounds because I think in either scenario you really need to be able to hustle, you need to understand uh personas and build rapport, and you know you need to give uh an experience that you know you need to give an experience that is painless, relatively painless, and enjoyable for for the prospect and operate with urgency.
Speaker 1:So I think that skill set translates to anything in business development. And go to market. I agree with that too. I went to tables for two, three years and you learn a lot of skills, a lot of people skills, as you outlined. It really is. So. We were talking about your first sell at Verizon. What was the sell you're most proud of?
Speaker 3:So the sale that I'm most proud of it is also at Verizon. Now, this was an authorized retailer. This wasn't Verizon proper, it was 100% commission rule and they had these like four stores in malls that were in my territory and so I'd been there for about six months. I had just started doing. Well, somebody told me you could sell B2B deals. I was like why doesn't anyone do it? They're like well, it's 100% commission. People come into the stores, you get inbound traffic. I was like all right, well, I'm not afraid to go knock on doors. So I sort of leveraged my contacts and went and knocked on doors and what?
Speaker 3:This month it was February, in the teens, 20 teens somewhere they ran their first contest they'd ever run and and it was, if you, the highest revenue in the company nationally got a cruise with a plus one for a week with all expenses paid. So I basically kind of accidentally, went and sold the largest deal in New York state history to limousine company, which was about 500 new lines of service. It wasn't the biggest in terms of revenue that I've done, but it was the biggest in terms of impact on me and the relative price point to what the average deal deal size was so it was like four hundred thousand dollar deal. So I won the cruise. I brought my buddy and I met my wife on a bar crawl on the second day of that cruise and he met her best friend and I now have two children. We both have two children, uh, with our, with the wives that we met on that cruise.
Speaker 3:That was the biggest one for me. If I count my bar bill from that cruise, maybe it was the biggest deal ever. Have you seen Titanic? I was the bald jack but, I made it.
Speaker 1:When you got in front of the ship was all over the ship arms out all over it.
Speaker 2:Yep what I'm hearing from this. My takeaway is knock on doors, because you never know what's going to be on the other side well, as far as I know, people still weren't doing it, like after I had done that.
Speaker 3:Uh, they did end the contest because myself and the buddy that I brought that also worked there.
Speaker 3:Uh, I saw the owner at a wedding a few months ago and he said hey, thanks for teaching us the lesson that we need to give different prizes for a contest because we had two of our top performers leave basically directly, uh, directly after that. But I think it's more testament to the way things are done, doesn't mean they are the way things should be done, like why didn't other people do that? Was it because they couldn't? No, it's because they likely wanted to get something different out of the job. They, you know, probably like that they didn't have to prospect. You know that they could make money on inbound traffic. But I think you know working at startups in general and I know you're good at this from experience, richie is we should be questioning the current state and how things are done, and there's a time and a place to sort of get on board and execute. But there's also organizations should be happy to have people questioning the current state and trying to find ways to be more successful within those parameters.
Speaker 2:For sure. And that kind of gets back to our last episode with Amber Diver talking about imposter syndrome and people who get comfortable in their routine. And when they get out of the routine there is a level of discomfort, whether it's learning new skills, questioning whether they're properly equipped for whatever new position they're in. But that discomfort of breaking out of a routine is a sign of growth and in your instance I mean this is growth. I mean it was very evident growth. You got out of the normal routine of everyone just sits in a store and waits for inbound, decided, hey, can I knock on a door? We can go B2B, that's allowed, that's cool. Why aren't we doing this? And then you just attack that head on. So I think that's where growth happens. I think if you're just in a routine, then your expectation should be that things are going to stay the same.
Speaker 3:Yeah, and everyone has imposter syndrome, like. I think one of the things that's like helped me to build confidence is my last three roles have been working with first time founders and it's easy to look at a founder or CEO and be like, well, they should know this, you know, look how high they are on the org chart, they should know all this stuff. But for many people, every day is the biggest team, the first time they're dealing with a challenge, the first time they're raising. So once you understand that nobody has all the answers and everybody's sort of just trying to do their best within what they know, I think it does a lot for confidence to say because you don't feel like the only person that feels like that.
Speaker 2:Yeah, in my mind there's the old, the old story about the emperor that has no clothes. I think sometimes you feel a little embarrassed and exposed, like I got no clothes on, you know. And then when the realization occurs to you that nobody has any clothes on and we're all a little embarrassed, then it takes a little bit of the sting away. So it kind of goes back to what you're saying there.
Speaker 1:So if we go on, we're all making it up as we go.
Speaker 2:Yeah, all right.
Speaker 1:Yeah.
Speaker 2:What is the sale that you are least proud of or possibly embarrassed about? Was there ever a sale that you closed and then you thought back oh man, what have I done? Has that ever occurred in your career before?
Speaker 3:I have a really good one that I didn't close. That's very embarrassing. I have a really good one that I didn't close. That's very embarrassing. So, selling transportation management systems, we had an onsite in like Iowa or somewhere that, like you, couldn't really get to, so we had to fly into a major city and drive hours to get there. So we go to this meeting. It was supposed to be like 3 to 6 and it goes like 3 to 7.30 and we had their leadership team in there. It went so well. So at the end we're like, hey, we're going to go grab a bite. Do you want to come to the CEO? And he's like, no, no, I can't. This is the place you have to go to. It's 20 minutes away. So we go. So what do salespeople do when they leave a customer meeting?
Speaker 2:They're going to blow out some steam, yeah.
Speaker 1:I mean you have to drink.
Speaker 3:You talk about how the meeting went. You know, and so I was an early on manager. I was there with a sales engineer and implementation person. So we're sitting at this bar and we're talking making fun of like picking fun at transportation that you needed a TMS because you know this guy was ancient or you know somebody's funny hair. And so I get up from the bar, I walk to the bathroom and as I walk to the bathroom I see the back of hair that looks like the hair of the person that was in the meeting that gave us this recommendation to go to this place and then declined us. So I walked to the bathroom and he's facing away from me and I walk back and it's him and like I try and make eye contact with him, no luck. So I never heard from that prospect ever again.
Speaker 3:And if you've, uh, richie, I don't know that we've been on any onsites together, but those that have been on my teams know that I now have a very, very, very strict rule as to. Usually you get out of the elevator and the sales guy's like hey, how do you think that went? I'm like, nope, we're not, let's get in the Uber and talk about it. So it was a strong reminder that, like you know one, you're not done. You're not done selling until you get an order, and also that like just a testament to why you know the gossip, especially in a public scenario, you know is frowned upon. So it was very, very embarrassing. I wrote handwritten letters. I probably called them like 25 times after that because it was like we're going forward, like let's well, this is great, let's schedule the kickoff for next week. It would have been in the top 10% in deals the company had. It was a horrible mistake, but all you can do is learn from scenarios like that.
Speaker 1:Do you think he overheard you?
Speaker 3:Yeah, in my opinion, there's no way based on don't? In my opinion, there's no way. Based on how the meeting went, there's no way that he didn't. And the way the restaurant was constructed, like I mean, this wall behind me is probably 10 feet. It the. It was a long, skinny restaurant, so we were at a bar like this and he basically had to walk within 15 feet of us in order to get to his table. So yeah, based on how the meeting went, I don't think he had to have hurt us.
Speaker 2:Do you think it was on purpose? Do you think that he recommended this restaurant, then declined your invitation, but decided to go anyways? Just to purposefully lend an ear to what you all would be saying, I mean.
Speaker 3:I don't know. I've spent a lot of time in my life thinking about why and how this happened, because the whole thing is very strange, like who recommends a restaurant to somebody, doesn't tell them they're going there and then declines an invite and still goes there. So I don't know. Maybe that's a smart way to do due diligence that buyers should start actively doing. Like, the next time that I'm part of buying software for a company and we have an on-site, maybe I'll try the same tactic to see if they talk about my shiny bald head or my wrinkly forehead Was it a mullet? It was like a mullet with a bald top. It was hysterically funny hair. It was genuine. It was like just the back mullet, but you still had the shine on top, so it was like the best of both worlds.
Speaker 2:That is the elusive skirted eggshell and the various types of mullets that are out there. There's a whole website, I think, that classifies different ones.
Speaker 3:What did?
Speaker 2:you call it Skirted the skirted eggshell. Oh, I like that.
Speaker 3:I think I could grow one, you should.
Speaker 2:You should.
Speaker 1:You'll never forget your mistake if you grow that yeah.
Speaker 3:Well, it's like I feel like with a, as a bald guy, you pay more attention to people's hair than anybody else. Like I'll be walking with my wife and we'll be walking in boston and I'm like when we walk past someone and she's like, who are, are you, are you checking that girl out? I'm like no, did you see the hair on that guy? So I do think that we're just, you know, as the Baldies, I think we're more sensitive to people's hair. But if we don't have nice things to say, we should probably just keep them to ourself.
Speaker 2:What was the funniest sale? So was there a sale that the circumstances were just hilarious. Couldn't believe what was happening. Things happen in sales. You never know what's going to happen in sales. It's always interesting, but is there anything that sticks out to you as particularly funny experience in sales?
Speaker 3:Yeah, so early in my career I was selling email marketing software and it was super high volume. It was primarily inbound leads but they were in moderate quality in the expectation we were making. Like 80 to 150 calls per day. Somebody on my team gets A lot of these are one person businesses If I have a catering company or from a real estate agent or whatever. It wasn't uncommon for there to be personal email addresses, stuff like that.
Speaker 3:So this person on my team calls an inbound lead and basically says like hey, my name is blank. I'm calling with this company reaching out because you filled out a form and you know I wanted to follow up with you and see how I could help. And the person must have been well, they were putting like advertisements on Craigslist seeking intimate relationships and they didn't listen to the person. All they heard is like you filled something out on the internet, how can I help?
Speaker 3:And then this man went into excruciating detail as to what he's looking for from an intimate partner and the salesperson who, like, was hysterical because he didn't laugh. He just kept asking questions, like, but not, they were like business-y questions. And the guy it was like four minutes of this guy just giving such horrific details and then ultimately like you can hear it in his voice when he figures out that he's not talking to who he thought he was talking to and hung up. So that was, that was the funniest thing. That I've been around and probably listened to that call hundreds of times and it used to actually be something that I would even show, like at team meetings. For you know other people at other companies I would say, like you know, here's the, here's the importance of qualification. You know you never understand who is who is on the other end of the phone and you don't. You can guess what they're interested in, but until you ask, you know you don't really know.
Speaker 2:And you don't know if you want to know, Did that rep ever call him back and take another shot at trying to get business, or was it like I'm done? I'm off the ride?
Speaker 3:I'm pretty sure it was done. I don't remember, but I don't know that there was a big business opportunity there. I don't know what the rep was into, so I have no idea.
Speaker 1:I'm surprised that the guy didn't realize that he wasn't talking to who he was talking to and he's like oh my bad, I thought you were somebody else and went on with my bad. I thought you were somebody else and went, went on with the, the sales call.
Speaker 3:Yeah, I mean, it was just like At some point I think he wasn't getting any of the comments or responses that he had been hoping to get or would have been getting if the person was actually calling in regards to his Craigslist ad. And yeah, I mean that would be. Yeah, I don't know, I didn't figure it out, but I don't know anybody else that's posting advertisements on Craigslist to find a partner.
Speaker 1:Not anymore. No no, not in these days.
Speaker 3:That's what? The glory days of the internet. I'm just kidding, not anymore, no no, not in these days.
Speaker 1:The glory day, that's what? The glory days of the internet?
Speaker 2:I'm just kidding, yeah 15 glory days, yes, 15 years ago. Can you just assume that anybody that's calling you saying I saw what you submitted on the internet Like yeah, if that's your first go-to of a response to a number that you don't recognize on your phone, yeah, that's a different time than today.
Speaker 3:Yeah, I mean Craigslist should have started Tinder or Matchcom or something. It's clear that they had a big business around that based on that guy.
Speaker 1:Best opportunities that based on, based on that guy, yeah, this opportunities. So so, ryan, um, here we go. Two part question, actually. So what cell or dill did you learn the most from? Would be one part of it. And what poker hand did you learn the most of from?
Speaker 3:So the sale that I learned the most from was a deal to a visibility deal to a exercise bike manufacturer and distributor, and at that point it would have been a deal that like doubles the company's revenue, and I hadn't.
Speaker 1:I think I might already know the manufacturer of these bikes.
Speaker 3:You, you'd be somebody that you'd heard of Um and we were working with a contact in innovation and we ran all these tests. They were totally qualified from a product fit and use case standpoint. But I didn't know what an innovation role was. Truly I didn't know. I just saw that it was like a VP or C level title and I was like they must have juice. And so I went. I mean, I talked about it in the board meeting, I went through like on paper, functionally there was no reason why this deal wouldn't happen.
Speaker 3:But not knowing what I didn't know I we didn't spend enough time, sort of on the business case and it still haunts me as like the deal that never was that like we basically got to the end and you know it's going to the ceo for approval and he was basically like that's ridiculously expensive and we didn't have alignment with stakeholders.
Speaker 3:So you know, for me it it taught me a lot about. I need to be honest with myself because and, rich, you may have heard me say this I say alcoholics don't get better until they admit they're an alcoholic. Capital is and truly what their paperwork process and business process is to procure services. I need to at least be honest with myself, because you know, if I'm honest with myself then I do a bunch of research or on. You know this role, I know the questions to go back to the customer with. So it was the most just glaring qualification issue that I've had and I didn't do myself any favors by promoting it internally that it was definitely coming and it didn't. And uh, you know it always haunts you when you're like there's no reason this shouldn't have worked, other than I didn't do the best job.
Speaker 1:I think the deal that never was I like that. I mean, I don't like it but I think it's something that a lot of salespeople are working on and are hoping for. In a lot of cases, that the deal that never was. I mean, you work in a deal, you think you're making progress, but it is going nowhere fast because you haven't done your due diligence. You don't know what's really going on behind the scenes and oftentimes it's nothing is going on behind the scenes.
Speaker 3:Right, I mean functionally. Could every single company use a CRM? Sure, could. Could every company use, you know, data on their target accounts? You know like you provide, kevin, sure. But if you don't, if we don't know the implication, you know why. That is how it ranks from a priority standpoint, like, truly, who can block it and who can get involved? We're just setting ourselves up to spend a bunch of time and cycles and ultimately not get the result anybody's looking for.
Speaker 2:Well, the thing is those situations when you're blindsided, right. I think back to deals where I know this deal is shaky, I can see the holes in it, and maybe there's not much I can do about the holes other than just see them. Right, I'm going to try my best to plug them as best I can. But I know that the premise is shaky to start, or I may see something that I don't think this is going to work out at all, but I got to follow it through because it might. You know, it's a, it's a Hail Mary, it's a seven, two offsuit and I've stumbled into the turn and I got two pair and there's razors all around with flushes and straights and everything in front of me and it's like I kind of want to see the river, to see if I boat up. You know, but it's, you know, but it's. You know that you're the odds are against you.
Speaker 2:But I think it's those moments when you're completely blindsided because you thought that all the holes were plugged, you thought that your business case was rocked, you thought that, um, you're on the path to, you're in the final stages, you're at the five yard line, and then when the ball's ripped out and it all falls apart.
Speaker 2:You're like what just happened and you don't even know like it's. It's almost traumatic when that, when that kind of dark mystery hits you like that, but it's only after that. I mean, I think there's a quote that says life can only be understood looking backwards, but it has to be lived going forwards can only be understood looking backwards, but it has to be lived going forwards. But it's usually weeks or a little bit afterwards when you start looking back through it and like, oh my gosh, I missed this, I didn't see this coming, there was this hole and you start seeing all the gaps and putting the pieces together and that learning the information that can come from that sort of experience can be really rich and meaningful. Yeah, I was just trying to summarize. Yeah, it makes a lot of sense that that's a something you learned a lot from. Hopefully, this poker, this poker story, isn't similar where it. It was better.
Speaker 3:I mean that.
Speaker 3:I don't have, I don't really, I don't really. Oh, I do. So, as I know, kevin and Richie know. So I used to play poker for a living for a period of time and I had a hand once, and this is when I really didn't have much money. I was probably playing for $200 or something and that $200 meant a lot to me and I had pocket eights. I raised preflop.
Speaker 3:Somebody called flop was like eight, six, two. We get it all in on the flop. The other guy has pocket twos, he hits a two on the river and it was crushing, soul-crushing loss. It's like less than 2% chance that that should ever happen. And I mean again, this actually goes back to exactly what you were just saying, richie.
Speaker 3:Like obviously I was not happy that that happened, but I think after I did, I spent a lot of time looking at like how could I have avoided this?
Speaker 3:And the end result was there's no way cards come out differently, like it's out of my, and all I did was put my money in in a scenario that I had 98% likelihood to win and, um, you know it, it really was just a reminder of sort of process over results, which you know.
Speaker 3:I'm still going to make that decision every single time. I'm still going to be disciplined and I'm going to be okay losing, so long as I'm following a methodology that I know in the long term, yields a better result, and that you're going to get unlucky sometimes, like there's variance in everything we do, whether it's poker or our relationships or our jobs. I could make a thousand cold calls today and have nobody pick up, and tomorrow I could make a thousand cold calls and have um, you know whatever 20 of people pick up and book meetings. So I think, like the point I'm trying to make is there's variance within percentages that is solved by how many times you put yourself in that opportunity. Like, if you have a 33% conversion rate and you run three deals, you might get none, but if you run 300 deals, it should be a hundredish at the end. So I think that was really the big learning experience for me in that end.
Speaker 1:And I think that's a very important learning experience or lesson learned is that you're talking about the 98% chance to win. You got beat. It's a bad beat.
Speaker 2:You got beat.
Speaker 1:It's a bad beat you kick yourself a little bit and then you move on. Right, because basically, 98 out of 100 times you should win that hand. So play 98 more meetings and don't worry about those those sure things. Right, because we, you know, I think we all experience this we got this sure thing, it's coming in. We're getting in front of our bosses, our managers, say, hey, this is a sure thing, and it just fucking falls apart. Right, I mean it. Just it just disintegrates, yep. And then if you're prospecting, if you're working that process, you're going to draw a river card In an inside straight. If we're going to go poker analogies right, something that comes out of the blue falls in your lap. You don't expect it, it's good luck. But as long as you're doing the activity and following a good process that you're building over time, it all hits out of the end.
Speaker 3:Yep, yeah it's, I mean it's.
Speaker 1:So you shouldn't get too down, you shouldn't get too up, just work the process and enjoy it.
Speaker 3:Yeah, what can I control within this process? And you know what would I do the same or what would I do differently.
Speaker 1:You know, you make those tweaks and you just get better over time.
Speaker 3:Yeah Well, and the other guy shouldn't have done anything different either. So, even though he was 2%, like the odds that I have top set and he has bottom set are so minuscule that, like so many times, I'm going to be paying him off with pocket aces or pocket kings, or you know eight, six some crazy two pair or something so like.
Speaker 3:Again, just because he was getting it in at two percent chance to win doesn't mean that he should do anything different, because the odds that I'm actually beating him are so low that if we both had the hand to replay a thousand times, we both do the same thing every time and it's actually so. That's like kind of the interesting thing about it is even the guy that got lucky on the river. If you know, I have the hand, I have you don't call. But most of the time I'm not even going to have that and you're just going to scoop the pot and you don't need to hit quads on the river.
Speaker 1:Yep, yeah, you know, I mean three, twos. I mean that's still a great hand, sure yeah, I'm calling you.
Speaker 2:If I have three twos, if I have pocket twos, and I spike a two and Sullivan's pushing, I'm going to say, ryan, why are you letting me take your money like this? And you're saying, richie, I'm taking your money. That's how it would go down just about every single time. It's a reminder of how oftentimes we think we're in control of things that we're not completely in control of, and that's a good reminder to look back at what is 100% in your control. You know, and yeah, it's a good audit practice to run from time to time to remind yourself what is in your control and what isn't.
Speaker 1:Yep, I tell you what what's in my control is. I'm going to sit down and I'm going to watch Rounders again tonight. I haven't seen it in three or four years. I'm in the mood now.
Speaker 3:Pay him, pays out the man his money.
Speaker 1:He beats me fair and square.
Speaker 2:You know what?
Speaker 1:I am going to go buy a box of Oreos and sit there and watch Rounders.
Speaker 2:Is there any other way to watch rounders? I don't think so Without a box of Oreos.
Speaker 3:I'll invite you to an online poker game too. So you can be. You know you're multitasking and uh, when, while you're in the spirit, you can uh, you can fire a little bit and try and hit quad twos on somebody. You can fire a little bit and try and hit quad twos on somebody, I will.
Speaker 1:I'll just play the river all night.
Speaker 2:There you go, ryan. It's been a pleasure, enjoyed this conversation.
Speaker 3:And how can people find you? So you can find me on LinkedIn or on my website, ratchetventurescom. And no, I really enjoyed this as well. And lastly, I just want to promote. This is a pack of baseball cards from the 2007 Lake Einhorn Storm, and there may be a Richie Daigle rookie in here. I have a few and waiting on the autographs. If you want a Richie Daigle autograph, you also can get one on eBay. It's not mine, it's $14. And waiting on the autographs. If you want a Richie Daigle autograph, you also can get one on eBay. It's not mine, it's $14. But thanks for having me on, guys. This was really fun Always a pleasure.
Speaker 2:Thanks, Ryan.