Ryan Staley, CEO of Whale Boss ($150MM Rev Closed) | How To Close The Biggest Deal Of Your Life

➡️ About The Guest
A career revenue and sales executive. Ryan Staley had his first success in business as an inside sales representative selling cutting edge technology and training to CIO’s, CTO’s and VP’s of the largest Investment Banks and Brokerages in the world. He finished #1 nationally, was promoted to Manager and then Sr. Manager.
This experience later launched Ryan into a leadership position (at a new organization) in which he was responsible for transforming a struggling business unit into the top performing office, creating an enterprise team from scratch and in developing a recurring revenue engine.
The new business unit resulted in growth from 0-$30M Annual Recurring Revenue, $30 Million in capital revenue, over (30) $500,000 plus contracts and a $20 Million contract (with ONLY 4 Sales people and without lead generation).
Ryan codified the playbook that he’s learnt and executed over every single sales role he’s held in his career and built out his own firm, Whale Boss, working with executives, CEO's or Revenue Leaders to implement a 7-8 figure sales system in relatively short, three-month sprints.
➡️ Talking Points
00:00 - Intro
04:18 - Ryan’s origin story.
14:05 - The importance of networking.
18:57 - How to move up market and sell bigger deals.
23:11 - Find larger new customers and sell more to existing customers.
24:51 - Customer referrals.
26:23 - Dropbox’s referral system.
29:29 - Help 100 million people grow their business.
35:24 - The secret strategy to sell to enterprise.
44:15 - Reinventing yourself later on in life.
46:46 - Good books for entrepreneurs.
48:12 - Ryan’s definition of success.
➡️ Show Links
https://www.linkedin.com/in/ryan-staley/
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➡️ Success Story Podcast
Stories worth telling.
Welcome to the Success Story Podcast, hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary.
On this podcast, you'll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups and entrepreneurship.
Scott will discuss some of the lessons he's learned over his own career, as well as have candid interviews with execs, celebrities, notable figures and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas and insights.
He sits down with leaders and mentors and unpacks their story to help pass those lessons onto others through both experiences and tactical strategy for business professionals, entrepreneurs and everyone in between.
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Welcome to Success Story, the most useful podcast in the world. I'm your host, Scott D. Clarie, and today I'm sitting down with Ryan Staley. Ryan is the founder and CEO of Whale Boss. His specialty is helping entrepreneurs land the biggest client they've ever landed. He comes from a background in business to business enterprise sales. Ryan has had repeat sales executive roles over his career. He's worked at Pitney Bose. He's worked at antenna software. He's worked as Vice President and Strategic Accounts at Flex Technologies Group. He is a chapter head at the revenue collective. He's a founding member of Rev Genius. He's a founding member of SalesHacker. And now he works, like I said, with his own company Whale Boss to help entrepreneurs close the largest deals they've ever had access to ever thought possible. He has over $150 million in revenue that he's personally close over the course of his career. And his claim to fame in his most recent role is scaling from zero to $30 million in annual recurring revenue with four sales people that he was working with under his tutelage with zero marketing, zero demand generation. So if you're just starting out regardless of whether or not you're selling software, you could be selling hardware, you could be selling a service to help you move up market and close larger deals. We have two incredible sponsors for today's episode. We have JustWorks, a tool that allows you to scale your small business easier, and then we have gusto, your one-stop shop for all payroll solutions. This is another episode of SuccessStory Podcast. They'll further do Ryan Staley. It'd be like saying YOLO and throwing all your money on GameStop. Now, granted, it could work out, but there's a lot of poor staff that lost a lot of money on that. You know what I'm saying? They're just going all in on a meme stock, right? All right, thanks again for joining me. Today I'm sitting down with Ryan Staley. He is a career sales and revenue executive. He had his first success in business as an inside sales rep, selling, cutting edge technology, training CIO, CTOs, and VPs. He finished number one nationally, was promoted to manager and then senior manager, kicking off an incredible career in sales, moving into more complex, larger enterprise organizations. He was a multiple year presidents club winner and equity holder. The experience building this incredible sales career launched Ryan into leadership positions in which he was responsible for transforming struggling business units into top performing offices, creating enterprise teams from scratch. The new business units he created in several, in one particular company, grew from zero to 30 million annual recurring revenue, 30 million in capital revenue, over 30 individual $500,000 plus contracts, and 120 million contract. If I'm not mistaken, with only four sales people, no lead generation, no demand generation, Ryan has codified his playbook across all the sales roles he's had over his career. He now has built out his own sales firm whale boss working with executives, CEOs, revenue leaders to implement a seven to eight figure sales system in an extremely short three month sprint. Ryan, very excited to have you on to break down your sales system to career. Thank you for coming on. What is your origin story? Like my superhero origin story? Well, first of all, thanks for having me on, man. It's good to see you. No, my pleasure. Yeah, I mean, doing like sales in marketing, I see everywhere. So you're doing a fantastic job of getting your name out there, man. Thank you very much. I appreciate it. I appreciate it. But this is this is about you. So yes, you're superhero origin story, and then your your your sales executive origin story, which is just as impressive, man. So where so you know, I walk through a little bit, but you know, give me some details. So you were your career sales. But was this on purpose? Did you go into sales on purpose? Or was this? What was it? Yeah. So I'll walk you through that. I'll walk. It was kind of interesting because like, and this is an end in the bio that you read, but everybody starts somewhere and my whole beginning into sales and what made it attractive to me. I mean, I started I was like a paper boy, you know, so I had a paper route, multiple paper routes when I was there. I then became a bus boy and had the the the wage of $3.75 an hour plus tips. You know, so so that was fantastic. But what I saw on the way home from being a bus boy when I was like caked and that Italian food smell from the pizzeria that I worked at and just have my dress shirt this kind of stunk, right? Disgusting. So I'm on my way home. There's got to be a better way to do this, right? And I come from a blue collar family where my dad was a police officer. And my mom was a teacher and they just worked their butts off. And when I saw them doing his working so hard and they didn't have really big jumps in their income or they weren't necessarily compensated for the size of the contribution that they were delivering. So a light bulb went off at me. I'm like, there's got to be a better way to do this, right? And so on my way home and I basically see a sign and the sign says, you know, start your career here. $14.95 per hour like apply within, right? So I'm like, oh, this is amazing. What could this be? What is this mystery job? Do you know what do you know what this company is that I'm talking about your smile? No, I just I think it's some sort of I don't know some sort of call center, some sort of boiler room with. No, no, you would think it is, right? So of course, very similar to the movie boiler room, which I actually did work in a boiler room environment. We could talk about that later. But anyways, it was a group interview. So you go in and give you this big presentation about all these things. And basically, there's a company called Vector Marketing, which is the subsidiary of Cutco. You're familiar with the knife. Yeah, the knives. Yeah. And so anyways, I listened intently. I asked great questions. So like 99% of the other people that were there, they invited me for a job opportunity. So I'm so excited. I backed up my car. I'm like, all right, I got this job and making thousands of dollars a summer, screwed the three dollars and 75 cents per hour. I'm pressured. I'm going to make five acts that drop like hurry up, throw it in reverse. And by the way, at that time, I was driving a wood grain station wagon mini van that I crashed into a pole right there. And I'm like, all right, it doesn't matter. I'm making so much money this summer. I'm going to destroy it. Drive home. Make the pitch to my parents. And then they gave me the soul crushing blow of saying, there's no way and hell you're going to work for Cutco because all you're going to do is pitch our friends. Yeah. And they were kind of right. Because that's what I said. Like, where are you going to get all these leads from? I'm like, your friends, I'm just going to pitch your friends mom and dad. And so long story short, I did, I was not able to take the job. I caused $12 hundred dollars worth of damage. And I had to kind of grind my way out to pay that off. But that was kind of like the pivotal point that got me interested in more of a sales career. And then from there on out, I started in college and then grew from there throughout my career and just continually just chipped away at it, grinded and escalated my career. So, okay. So then you went into more traditional roles. You went into SDR. You went into manager, senior manager. You've done the gamut of sales stuff. So let's, we can touch on any any any piece of that because I'm curious was you mentioned boiler room. You mentioned SDR. I feel like you've done like every sales job in the world. But I obviously want to unpack like what you did when you grew a company to 30 million. Were there any notable career points between the Cutco SDR to the 30 million with four staff that you wanted to bring out that were just incredible things that you learned or anything like that? Yeah, I can give you a couple of nuggets. I mean, and just for clarity purposes, I never was an SDR. Oh, sorry. Like SDRs didn't even exist back then. At least the term that I was aware of. So I worked for inside sales. So it was like boiler room where I had a one call close people for a training package of like $4,000. Now it wasn't a stock that didn't exist or anything like that. It was legit. However, there was kind of two pivotal moments that that I experienced throughout my career that really changed everything and then helped pave the way for that trajectory of of basically what happened with that that road that you mentioned in my bio. And so one of them was I was a rap and when I was a rap, I was I closed zero deals in the first eight months there, which is really, really hard. However, I had a revolving door of managers, brand new office that was opened up. And finally, I figured out and found my way. So you know, month nine got a big deal, month 10 got a big deal, month 11 and 12, right? So I was just a slow starter, a fast finish with that. Then I continued over a years did the same thing, right? And basically, what happened was I got sick of work in 60 hours a week to make 100% of my quota. When I saw another guy who was flying on private jets, worked nine months of the year and only worked 30 hours a week, Matt. A sales rep is a sales rep was flying on private. Yeah. What industry was this? What do I have to fly? This is like managed services for printers like like HP like smart like managed princesses. All right. Well, so it was not anything sexy by any means. But he was used to making good money or she was making good money in. Yeah, he was really well. And you know, I'm sure I might be good to it. There's some other genetics that he was doing. But anyways, I'm gonna take the high road. And so what happened was I like really dissected what this guy was doing. Like I got to figure this out. So I reverse engineered it, found out this guy basically out of his whatever 180% of quota he hit it every year, roughly about 130% of it came from like two deals. And it's done like, okay, he's he's basically got two customers. He's doing that and then he's just adding on some other components, right? Every single sales company I worked at had the same kind of model where there was one or two people that would be, you know, those those people that are like chairman's club, 190% 200% everybody else was like 140% right? And it was the trend. It was a pattern. So what happened was I started to really focus on that. And then what happened was when I was a leader, I hit a wall because I was my first time in management was grinding away. And essentially things started to take off, but they shifted me to apartments. So they're like, Ryan, you're great at big deals. We want you to start this enterprise team from scratch. And so one of the we had no playbook. We had no marketing department. We had no SDRs. We had nothing. Like it was just like, I didn't even have a team. They're like, just go figure it out, Ryan. Like awesome, sweet, right? So what I'm happening is I looked at that experience. I had prior. And I'm like, okay, this is a track record. This is what they're doing. So I started off like deconstructing all the big deals that our company had and what were the patterns and verticals and exact situations that they did. And then from that, basically I started to see patterns in terms of how people bought what they did and how they acquired different customers. And so I took that, that like basically that I modeled all those success factors and then put it into and packaged it into a process that I developed from scratch on how to sell enterprise deals. And what we did is we leveled up each year. So for example, our monthly reoccurring revenue for the size of the deal might be $20,000 a month, year one. Well, the next year we leveled it up and we got, we started getting $70,000 a month deals. Then it was $150,000 a month deals. Then it was, you know, $300,000, then it was $600,000. So that was the way we scaled really fast as we kept and specifically focused and we're really hyper targeted on continually expanding and multiplying our biggest customers. And that's how we would be resourceful and get those results. That's that's an interesting. So you were just now the name makes sense. You were going after the whales, you were going after that's the name. So that's that's the point where you scaled. So you and by the way, I guess I sort of skipped over this, but I didn't even I didn't even realize when I said it, but SDR. So sale development, right? I guess that's the that's the modern iteration of an inside sales rep for for whoever is listening and trying to unpack those acronyms. So as you as you went through, you finally ended up in the sales management position, you sort of reverse engineer this process. This is the process that you used to build out this $30 million revenue machine in your business. When when do you start to branch out on your own? This is like probably this is the this is probably where you start to understand like, okay, I have a process here. It's worked repeatedly and now there's an option for me to take this and and run with it because obviously other companies need this because they're always hurting with these enterprise clients. Yeah. And so I think a lot of it started. It was really interesting Scott because it started. I just I didn't really work on building my brand. I was so focused on achieving those results internally. And I networked it with customers or customer facing components, but not with with peers. I really it all their company that I never peers at my company. So I was kind of like in my bubble. And that's one of the biggest things I tell the salespeople it's always always always talks people outside of that. So what happened was I started talking to folks as I was building my brand and they're like, what'd you do? You know, because a lot of salespeople are competitive, but they're like, so so give me your baseball card. What are your stats? What did you execute on? Right. And then I started telling the phone like, huh, that's like really impressive. I'm like, it is. They tell me at work, I'm not doing enough. Yeah. You know, so like I was like, oh my god, like I got something here, right? And then I started asking around. I'm like, like, dude, nobody else is doing that. And so I'm like, okay, this is interesting. So basically what happened and we talked about this a little bit before is my firm, I started to work on creating a methodology and a framework around this. I started to create a course for sales reps, not for companies. My company found out about it. They didn't like it. It was in the middle of COVID. And they say Ryan's kind of free to leave, right? After being there for nine and a half years. So it was like the peak of COVID. So that's a whole other story we can I don't want I don't want to bring up a little heart. I don't want to bring up bad memories. Give you a little PTSD. Yeah, it's suck, man. But first four or five months, I was just trying to figure out what was going on. I mean, that's when the riots were happening in Chicago. There was all sorts. I mean, it was a really unique time. And I kept saying it myself as a point of motivation, like Ryan, this is going to be a hell of a comeback story. This is going to be a hell of a redemption story. And so I did an enterprise summit last year in October. And I started talking to people once again, this kind of came to the surface. And I'm like, I really want to be working with with CEOs. And when I started talking to my network and people are like, well, what you did, I want you to do that for my company. And so I started to focus on it. And the more I focused on it, the more it started to grow. And so now essentially I coach CEOs on how to implement those systems that got that result from me before in a resource constrained environment where they don't have tons of venture capital. Yeah. And now, and I actually, I love something that you said before that actually really resonated with me based on your own past experience and probably many others. There's a lot of a lot of founders that all they want to do is raise money. All they want to do is bring on investors. Oh, it's too slow to bootstrap. And for a lot of people, it is very hard to bootstrap. But you know, your purpose is, okay, there's other ways to to go up market, to close multi million dollar customers without having to have venture capital and and put on this and like incredibly stressful growth trajectory that you always go on when you take in outside money. So that's also something that's very, the fact you brought that up that you realize it a lot of founders deal with that. I think it's quite respectful. So how is it, how has it been because when, you know, the fact that you've done this for companies, you did this for your own company, it blows my mind. Honestly, the fact that they let you go because of a course that brought them X million dollars. Honestly, like I have, it is what it is. I have my own thoughts about that, but that's okay. You know, I'm all about building personal brands and I'm a big component of it, regardless of whether or not you're in or out of a company. I think it's only a benefit to the company at the end of the day, but you know, not everybody agrees. So moving on from that. So what are your results like working with companies? You make a bold claim. You say, how did you, the way you phrase it is seven eight figures implement seven eight figure sales systems in a three month period. I'm assuming industry agnostic doesn't matter. This is what you can go and implement. So walk me, walk me through some of the results that you've actually have. What is your baseball cards? If you left? Yeah, sure. And, and, you know, as a, in full transparency, this is something that I've been working on really for six months. So it's still like the results, you know, I don't have tons of baseball card stats on it. All that I will tell you is that like 90% of my customers are renewing after the initial three months because they want me to keep working with them. So obviously I'm, I'm doing something right. And what I'll tell you, I'll give you kind of the framework of kind of how I approach it with that be helpful Scott. It would be great. Yeah, I think that would be good because that's, uh, there's two things that I want to pull out of you. I want to pull out of, of your mind as somebody quickly transitioning into entrepreneurship and how you did that, but obviously the, the sales system is also, let's keep. We gotta go. Yeah, cool, cool. All right, awesome, man. So, so basically the way you look at it is there's all you software companies that are being created, right? And I, I specifically focus on higher ticket companies. So companies that are signed solutions that are 30,000 or 40,000 dollars or more. Really? Because it's a lot of, it's a completely different motion. If you're selling a $99 a month product or a $299, it's completely different than if you're selling 40,000, 100,000, 200 and up, right? So that's, that's kind of my niche that I work on because there's so many more complexities to do that. And so basically the way I look at it is there's all these software systems, all these software, I should say companies are being created tech companies are being created. They spend all this time systemizing the development of their software and the constant updating and operating system for that, but they don't create the operating system for sales. And so really I look at that and I'm like, okay, what can you do to implement a sales operating system? There's three components that I look at when we're doing that. Number one is that, that specific strategy I mentioned before is, okay, what are your top five clients? And how do we replicate and expand them every single year, right? What's the process so that if you have five customers that are paying you $20,000 a month, how do we make that 10 customers next year that are paying you $30,000 a month? The numbers add up really, really quen. A lot of times, too, if you focus on it, you could even double it. So if someone's paying you 20 K a month, you could double it to 50 K a month. And it doesn't take a lot of effort. Where people go wrong in the biggest mistake they make is they try and go from 20 K a month to $200,000 a month. And a lot of the customers like they don't have the references, they don't have the infrastructure to support that. Whereas if you go more of a doubling motion, it's a lot easier to make that bridge. So that's, and that piece, do you do that? Do you recommend doing that with new products or like, what's the strategy to actually uncover that additional budget? Is it selling to another business unit within the company? I just want to take a second and thank the sponsor of today's episode JustWorks. JustWorks relieves all the headache to do with admin work or HR work for your company. If you're a small business owner, if you're an entrepreneur, JustWorks is going to allow you to focus on building the business, not working in the business, right? Work on the business, not in it. And all the, all the admin headaches that come with running and scaling of business, JustWorks is the tool that allows you to get those off your plate. So these are just some of the things that JustWorks does. It allows employees to onboard themselves in a few minutes. It gives them immediate access to all your healthcare insurance plans, large national group insurance plans. It gives you access to 24 seven HR consultancy. You can access anytime. It allows you to run payroll, manage benefits, figure out state by state regulations and tax implications. It allows you to disseminate all of the sick leave policies, insurance policies to your staff without having to be bogged down with administrative headache and answering questions. Your staff can use JustWorks. Your employees can use JustWorks so that you can truly focus on growing your business. One of the biggest issues that entrepreneurs have or small business owners have and I've seen it firsthand and I've spoken to a lot of entrepreneurs and small business owners is that they get too caught up in running the day today and they don't focus on the vision. And if you don't focus on building the company, if you don't focus on the vision of the organization, it's not going to grow. So you owe it to your employees to invest in tools like JustWorks so that you can focus again on that vision and focus on building. And then the other admin components that you just don't want to take on, that's where JustWorks has your back. If you want to learn more about JustWorks, go to JustWorks.com and you will see a full list of all the various things they can do for your business, all the tasks they can automate, all the headache they can remove. So go to JustWorks.com for more info and you can find out exactly how JustWorks can help your business. All right, let's get back to the show. What's the go-to? Well, this one is not new customers. Okay, okay, okay. So the Wales scale operating system, that's the first one. So that's not new customers. So the second one is what you just hit on is a secondary sales system or a secondary sales process. So and basically that's that's expanding existing customers that in terms of the average spend or the average cart value, average dollar value, lifetime value, whatever acronym you're using. And so what happens is companies will spend, especially on larger deal sizes, those spend six months, eight months, nine months, sometimes even a year getting a customer, they get the customer and then they don't talk to them. They don't have a process that after they get that customer, how to create continual value while also seeding and selling every time that they see them of the next problem they have. Because let's face it, whenever you get one problem solved, there's usually five new problems that occur as a result of that, right? So that's number two. Number three, and this is this is my favorite. This is what I'm on fire about just because it's so simple and Scott, I had an epiphany about this when I'm staying in room. I was at a conference. There's five thousand entrepreneurs and Tony Robbins asked like, how many people have one of these systems in place? How many people have two of these systems in place? How many people have three? By the time he got to two, less than four percent of the room had this in place, he's like, that's these single like one of the single biggest components you could do to double and triple your company. And you want to know what it is? It's a system around customer to customer referrals. If you look at Dropbox, Dropbox literally grew from 100,000 users to four million users in 18 months because of a referral system. Interesting. That's the main source of it. You're right. I think you're 100 percent right. Nobody really focuses on that, right? Yeah, so that's that's that's a specific example. There's another company that I know it's true. This is an out on the web or anything like that, but essentially they grew from one million to about five million in 18 months and sold to LinkedIn. And they did that through a referral system. So it's like you build up all this capital with your customers, but you don't systemize on them spreading their word and accelerating the word of all the work that you've done to them to make them happy. And that's something that I don't think I've ever heard discussed at an enterprise level ever. Really? Because you ask for referrals. You ask for referrals when you when you complete an RFP. Maybe you ask for some referrals to record a video and throw it up on your website. But those are not systems. Those are one off transactions to get some social proof, right? Yeah, how do you build how do you build an enter what's the drop box? Do you know the drop box example? How they built it? How they yeah, that's super simple. And I'll give you this as a takeaway, but then I'll give you kind of like high level framework of of kind of how I view it or approach it. But like all drop box did is they included in their implementation, you know, seven steps to implement it and get started. And step number seven was if you refers to people, you get an extra 250 megs of space. That's it. So that's that's that's a real simple one. Now grant that's on a lower ticket 99 dollar a month one. But on the enterprise side, there's a lot of opportunities. And so the way I approached it and I got hit by a bunch of different angles with this. But basically I use the behavior design that was that created Instagram that the founders of Instagram used to basically explode that platform. That's social media platform. So I use the behavior design from that to make it super drop it into an existing process that you already have. So it's not all these new things that you got to do right from your team's perspective. And then also I lit I leveraged the behavior dynamics of a lot of psychology. And I'll give you a simple principle that works just wonders. And this is very, very simple. However, it's got to be customized to the individuals. But like, for example, if you heard of Robert CLDNA's book persuasion or persuasion or influence that persuasion, persuasion, yeah. So the reciprocity principle, which is number one, is the idea. And I love this example. It's so simple. I really get it. Is that, you know, when you go and you go to a diner, you go to a restaurant and your waitress comes or waiter comes and they're like, all right, here's the bill. Before that, the ones that give you something, you get a 17% increase in tips, right? Now, if they make a custom or specific to you, like they bring you the bill and it's unexpected and they come back like, Oh, here's some coffee. I realize that you really like coffee, you can take this to go. Those people get a 30% bump in their tips. And it's because people feel the need to reciprocate if you give them something of value, specifically on the spot. So that's part of the process that we integrate in there. And then the third last but not least step is you map the process on your side, you map the behavior dynamics, but then at the same time, you mirror those to the peak emotional experiences that your customers have throughout their journey from the point in which they sign with you to the point in which they have their first win to the point in which they're, you know, over the moon. And those are the right times to ask because you give them something, they're super ecstatic. They love you. And then you got to make it easy for them and then they'll give you those referrals all day long. That's, that's very, very smart. So this is the three part, this is the three parts, this is the implement. Now, how do you, how do you do this in three months? That's, that's, that's not easy either. You can, you know, you go into an enterprise organization, you do it over a year, but what about the three month piece? Yeah. And so in full transfers, I'm not working with billion dollar companies on this, right? No fair, fair. Yeah. So just a little bit more agile. These are people that are selling to enterprise companies, selling to big, big deals I should say. So, so it's, now granted, however, I will tell you this, there is one of the biggest companies in the world that I'm in conversations with that is not doing this. So like it scales from up and down, which is why a lot of people are highly interested, and then you map the metrics to it and it's insane. And it's even backed by HubSpot that 92% of, I think it's maybe 84, it's 84% I believe 84% of new purchases start with a conversation from a peer. So I put some gasoline and accelerate that, right? Yeah. So the three month thing, what you're asking about that is basically it's, it's the way you look at it. And when I work with folks, and I'm going to start to, to codify this into a course and a training that I'm doing, so that I could expand this out to much more people, because I believe that you can make an impact on, Scott, I mean, the number I threw out there is 100 million. I still got to do a research, make sure that number is achievable, but help 100 million people to grow their businesses by giving first to grow their business, which I think is beautiful about the model, because people light up when you, when you do that. And how it's done in the three month period is really looking from macro to micro. What is that company specifically doing? How are all their processes system set up? And then how do we map those kind of different components to them? And then at the same time, plug into what their customers are going to respond to. So look at it from like assessment to execution is kind of how I approach it. I love that. I love that. Okay. Now I now I have entrepreneurial questions, because I, the only reason why I'm really curious about your entrepreneurial journey, is because it is fresh. And you just did a complete pivot in the middle of a pandemic. And you're not, you know, you saw, you saw your hair, you're not, you're not, you're not, you know, game over. Yeah. I think it's looking bigger every day, but that's okay. That's okay. Whatever. You still have some. So it's been like an okay couple months. No, I was going to say so it, so I wanted to ask you entrepreneurial questions about your journey. But is there anything about the selling system or some of your sales experience that we didn't go into? Because you gave a really nice summary, but I didn't want to cut and cut anything out. Well, yeah, I mean, I'll give you a micro. I mean, long story short is there's a lot of complexity to really big deals. Yeah. And what I'd recommend is if you're a founder or your CEO and you want to move up market where you're trying to muscle this up and do it on yourself, work with someone who's been down that path and not someone that has necessarily worked at Oracle or an SAP, not that there's anything wrong with them. However, a lot of times the brand recognition is different than working with something that's completely unknown. So my recommendation doesn't have to be me. There's other people out there. I'm sure that you can find, but work with someone who has been in your situation where they're going from an unknown brand to selling really big companies, because there's an art to it. So something that you get anything else about me that's just a little advice or tip. I just want to take a second and thank the sponsor of today's episode, Gusto. Gusto is the easy online payroll and benefit solution set up for small businesses. So really, Gusto is payroll benefits onboarding HR all in one place. And it helps you accomplish all of that, but keep in mind it is built for the business owner. It is a people first platform. It is the most user friendly tool that I've ever used. And this is really just to remove all the busy work, all the admin work away from running a business. So let me just list out what it takes care of because it really is an all in one. So it does payroll, W2s, 1099s, health benefits, 401ks, offer letters, onboarding checklist, software set up, they transition your entire business from whatever you're previously using to Gusto free of charge. They also have on-demand access to HR experts in the platform. You can get unlimited pay rolls for a monthly price, automatically file all of your taxes, state and federal. When customers migrate to Gusto, they don't leave. 94% of their customers say that Gusto has dramatically streamlined all of their payroll headaches compared to whatever software they're using before. And three out of their four customers say that they can run their entire company's payroll in under 10 minutes, which is absolutely insane. And a huge huge huge savior for anybody that is trying to run a business themselves that doesn't have all the help in house just yet. Or perhaps they do have the help and they're just not efficient or they're not quick and you want to perhaps scale that person. That's what Gusto can do for you. And they're also offering a great discount for everybody who is a success story podcast listener. They're giving you three months free of the tool. So if you go to gusto.com slash Scott, you get three months free of payroll solutions. There's no limitations on your account. So go to gusto.com slash Scott, sign up and you will remove all of the headache when it comes to running your business and you can now work on your business as opposed to in your business. gusto.com slash Scott, I promise you, this will get rid of all the pain points, all the headache. This will be the best business decision you've ever made. All right, let's get back to the show. And just I guess one thing that just I just thought about what about what about the risk in putting, you know, all your eggs in one basket so to speak going after enterprise versus maybe winning some smaller deals quicker. Is that an issue? I think no, because I don't believe you should do that, right? It'd be like it'd be like saying yellow and throwing all your money on GameStop. Now granted, it could work out, but there's a lot of poor staffs that lost a lot of money on that. You know what I'm saying? Or just going all in on a meme stock, right? So so and while we're on the topic of investments, real simple way is look at and you don't need to hire a whole new enterprise team, you can with this method, you can start to have your team expand up and do it and look at it like a balanced portfolio, right? If you want to start going up market, have 30% of them be enterprise, you know, over 50% being mid market, it may be 20% being small and medium business. It all depends on your business. But or if you're mid market enterprise, you do a 70, 30 split to start and then it could eventually move to 50, 50 because then you have the lawns and then the short and medium wins too for cash flow purposes. That's smart. Very smart. Okay. Let's let's break down your entrepreneurial journey. So you were you were you're starting a course, you were let go. What do you do next? Do you work like how did you decide to start this company and and one of the steps you took? Yeah, man. So I always had the dream of starting my own company and doing my own thing. I think like I stayed. I probably should have left like three years ago to be completely honest. Like I stayed two years too long. And the reason being is I was always, you know, once you start to get to a point in the corporate world, you make good money, it's safe. And it's almost like you feel bad if you turn your nose at that and say like, hey, I'm going to I'm going to do my own thing and start from scratch, right? My situation was a little bit different. So I was forced into it. However, not once that I look for another job. I'm like, I'm going to find a way to make this work. And it's been my dream. I don't want to ever work for someone else again. Now that's where I'm at right now. Maybe it changes, right? So I burn my boats. I mean, and dude, I'll tell you, man, when you first have it, it was really hard. And I haven't told this to anybody at all. So your folks are first to hear it, but in a sense of vulnerability. Yeah. Like because it's not it's not a wound anymore. It's probably more of a scar. But I remember like it was not a good day in the daily household. My wife was like, what are you going to do? You know, she was upset. My son thought that you played in band at the time. And I love the little guy. He was like, Dan, am I going to have to play my saxophone for money? Like we get kicked out of our house. You know, and it's funny now. However, it was got wrenching to see like my family and all that indecisiveness. So I just started shipping away and trying lots of things. I had some mentorship in different areas. I joined some coaching groups to upskill myself because that's the fastest way to get results. You got to invest in yourself to get those outcomes. And I started trying a lot of different things and really taking note and worked a lot of hours. Yeah. And really it kind of got to the point where that was the first five months of it. And then once I made the shift, you know, I had a lot more clarity around what I needed to do and how I needed to approach it. So the biggest thing that I think is really, really important that I made the mistake that I'll share with you the listener is that I try to do too many things at once. And I still have the curse of the shiny ball syndrome every now and then now as well. But to really narrow it down on one offering and just absolutely crush that offering. And then you could think about scaling later. So that's that's my advice and that's that's kind of where I'll be out into and I'm out of the thick of it now and things are exciting. That's amazing. And that's good for you. Very good for you. So congratulations, but that's not easy. And so you found this, you found that this is, you know, you had your product that you had proven out that it has worked and then you just sold it. You sold this strategy to businesses. And now when did you close your first deal as an entrepreneur? Was it month five? Yeah. Well, so I started having people as funny because I started having people want like want me to coach them on how to sell because I helped sales reps like I helped one person increase their income from never being in B2B sales to almost like 500K and like a couple of years. So, so people, I started, I had some coaching students like right from the get go. Like people wanted me to work with them and help them. So I had kind of different avenues where I started to do that. My first consulting company that I closed was right after I did the enterprise sales summit. And it was kind of on accident because I wasn't focused on it. But I had someone for my network tell me I want you to help me with this. And then I had someone else for a referral tell me like, Hey, like I want you to help with this. And and then I started getting more referrals, leveraging my own dog food. And that's where my passion for referrals comes. I basically started to create, you know, really, really good cash flow and momentum from harnessing referrals. I was even focused on that. Scott like originally like I wasn't I didn't play inside my network with that. I was always silent in my company. Like I said, so I'm like, this could be the best one of the best gifts that I could give entrepreneurs or startups that are starting. If I could teach them how to do this and systemize it. And right and and right now is it is it still you that has to go in and teach or are you are you starting to classify this because you said you're trying to do that. Yeah. So I have customers that I work with one on one. And obviously there's limitations to that. You know, in terms of scaling your time. And so I'm doing that, but I'm going to have some new offerings coming out very, very shortly. So I'm excited to that. I'm going to have a course. It's probably going to be a bootcamp type fashion like a 12 week course to implement this. And I think, I mean, it could it could deliver massive, massive results. I mean, one of my customers, they had with one of these just one of the operating systems I mentioned, they had a person who is spending 25% of their time. They was in the training department before. And they got the entire ROI on the consulting engagement in like a month and a half. It's pretty damn good. Yeah. And so when she starts to see results like that, you're like, okay, there's something here. I got to share this with people. Very good. And I'm curious because you're still like you're still living at what was the biggest biggest misconception about entrepreneurship building your own business that you had going in that you sort of matured on over the past year. Yeah. One of the biggest things is I waited too long to to leverage other people. And smart. Okay. You know, I tried to loan wolf it with my pride. I'm like, I'm going to figure this out. This is what I'm going to do. Right. And I started talking to more and more people. And at the same time, I wish I would have outsourced different components of what I was doing. And I would have massively accelerated like where I was going and how. Do you outsource stuff now? Like I like it's just it's not just you now. You're starting to grow like team and build it there. Right. Yeah. I have a different contract. You don't even have to hire people full time right now. That's the beautiful thing, right? So you can ramp it up whether be with your content, whether be your your your podcast development, whether it be I mean, there's so many different. You're talking about this before. Like how I'm, you know, like I'm trying to do that now just because you and it's like a classic like first time. I don't even know it's first time. It's just classic person who's never scaled before problem. They just feel like you can do everything themselves. Yeah. And that's that's I mean, that's a map like. Here's the thing. Somebody told me there's a great book to read on this is Who Not How? Have you ever heard of the book Who Not How? By Dan Fulton? I the it is a familiar name, but I don't I'm not placing it. Maybe I've seen it in the past. I can't. Okay. So any entrepreneur that wants to get more skilled at outsourcing read that book. Like it totally changes the game in terms of your time. Like you could buy your time back at a discount massively. It's insane. So that's my tip. Okay. Good. That's good. Okay. I like to do some some rapid fire career questions to pull it at the end. Is there anything else that you want to touch on about what you're doing with their business going forward or do we cover most everything? No, man. We we pretty much covered anything. Everything. So just like if you're interested. Connect with me. I mean, like connect with me on LinkedIn and I've a podcast as well sales and marketing built freedom. Nice. Very nice. Okay. Good. All right. Biggest challenge you had in your entire career. How did you overcome it? Yeah. I think my biggest challenge in my entire career was when I got demoted even though I was doing well because I was burnt out and fried. And at the same time, my relationships were melting down with my family with my kids because I was so burnt out. I was fried. And how I overcame it is I started focusing on things outside of work. Just like I did goals for work. I did goals about relationships and fun and life and and that changed everything. My results got better. Everything got better. So that's one thing I'd recommend. Good. Smart. Very smart. What would be one thing you would tell your 20 year old self? The 20 year old's not even my 21. So I can't even drink yet in this scenario, right? No, you're still responsible because then the lessons go downhill once you start drinking for like the next five years. So don't. So here's what I would say is like early early early early on my career. One of my one of the beautiful gifts that I got for my parents is to work hard. And that's only a piece of the equation. So my advice I give to my 20 year old self, not my 21 year old self is to really seek out the best of what you want to become, who those people are, what do they look like, what do they believe and reverse engineer that and you can do anything in really fast time. And it took me a long time to figure that once I figure that out. I mean, things took off like a rocket. Good advice. Very good advice. You just touched on this, but I'll see if you get a different answer. The person or people who have been really influential in your life, what did they teach you? Yeah, I mean, you know, my parents and my wife, my kid is just just being loving and putting your heart out there and just being supportive no matter what the situation. And that's been absolutely amazing with all the ups and downs that I've had in my career. So this is a different answer. It's more of the emotional sides got, you know, so that's what I would say is just people being there for you in situations we really, really need them. Good. What's a podcast or a book that you'd recommend people go check out besides all the ones you already recommend it. The one way I'm dropping stuff left and right. Okay. Can I give two books? Is that cool, man? Yeah, for sure. Go for it. Go for it. So I like a little recency bias, but one book that's really good for exponential thinking is a book called you squared. Have you ever heard of you squared? No, I don't know that. These are new to me. It's only 36 pages long. And it's one of the most thought provoking books. It's a mentor of my recommended me to read it every single week because it's all about thinking differently and ways that can exponentially increase your life. So that's book number one, book number two that I am in the middle of that I'm absolutely infatuated with is the innovation secrets of Steve Jobs. I could have read that book 10 years ago and not get out of it what I'm what I'm like internalizing right now with how truly truly masterful he was at vision and inspiring people at an emotional level. And I think it's some of the stuff is really beautiful when he did. I know he gets painted as like a kind of a jerk or a hardcore guy, but there's some amazing things that he did that could help you if you're interested change the world. Very good. What does success mean to you? Oh, that's a good question, man. And I have the type A achiever where it's like I got to see results like tangible results. I heard Tom Bill you say this and it really, really hit me is like how you feel about yourself when nobody else is around when you're by yourself. Like how do you feel? Like and that that's pretty powerful, man. That is. Yeah, very that's a good answer. And then most importantly, where do people connect with you? All your socials, website, any of that. Yeah. So my website is Ryan Staley.io. That's the best. So my podcast is there. I get content there then you can connect me if you're interested and need some help on some things that we talked about. Awesome. That's all I got. Perfect. That was awesome. That was really, really good. Thank you, man. Let me make sure this is all.



























