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Success Story Podcast

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

By July 26, 2021March 4th, 2022No Comments

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.

After 2.5 years, Ryan shifted to a complex sales position for a privately held managed services provider that had no customer base in the Chicago market. He grinded and found a way to eventually becoming a multi-year President’s Club winner and equity holder through creating his own go to market strategy and execution plan.

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

  • 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.

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What is the Success Story Podcast?

On this podcast, you’ll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups and entrepreneurship.

The podcast is hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary.

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.








Read The Transcript (Machine Generated)


sales, people, customers, company, business, scaling, career, building, month, payroll, enterprise, ryan, started, biggest, selling, deals, referrals, scott, results, book


Scott, Ryan


Scott  02:00

Alright, 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 CIOs, CTOs and VPS. He finished number one nationally and 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 you’ve 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 dollar contract if I’m not mistaken, with only four salespeople, 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 on 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 ya. Oh, my pleasure.


Ryan  03:48

Yeah, I mean, do like sales and marketing I see everywhere. So you’re doing you’re doing a fantastic job of getting your name out there,


Scott  03:54

man. Thank you very much. I appreciate it. I appreciate it. But this is this is about you. So yes, your superhero origin story. And then your your your sales executive origin story, which is just as impressive, man. So we’re so you know, I walked 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? Yeah, so


Ryan  04:18

I’ll walk you through that. I was it was kind of interesting, because like, this is an 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 busboy and had the the, the the wage of $3.75 an hour plus tips. You know, so so that was fantastic. But what I saw all the way home from being a busboy 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? It’s disgusting. So on the way home, like, 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, my mom was teacher, and they just worked their butts off. And what I saw them doing is working so hard. And they didn’t have really big jumps in their income, or they weren’t necessarily compensated for the the size of the contribution that they were delivering. So a light bulb went off of me, I’m like, there’s gotta 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? And I’m talking about your smile? I


Scott  05:48

don’t know. I just I think it’s some sort of, I don’t know, some sort of call center some sort of boiler room? No, no, you would think it is right.


Ryan  05:55

So, of course, very similar to the movie boiler room, which I actually did work in a boiler room environment. And we can talk about that later. But anyways, it was a group interview. So you go in and I give you this big presentation about all these things. And basically, there’s a company called vector marketing, which is a subsidiary of Cutco.


Scott  06:15

You’re familiar with the knives. Yeah, the knives. Yeah.


Ryan  06:20

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 so excited. I backed up my car. I’m like, all right, I got this job and making 1000s of dollars this summer, screw the $3.75 per hour, I’m crushing it. I’m gonna make 5x that drop, like Hurry up, throw it in reverse. And by the way, at that time, I was driving a wood grain station wagon. Oh, minivan that I crashed into a pole right there and why it doesn’t matter. I’m making so much money this summer. I’m going to destroy up, drive home, make the pitch to my parents. And then they gave me the soul crushing blow of saying there’s no way in hell you’re gonna work for Cutco. Because all you’re going to do is pitch our friend. Yeah. And they were kind of right, because that’s what I said, like, where are you going to get all these leads from like, your friends, I’m just going to pitch your friend’s mom and dad. And so long story short, I did. I was not able to take the job. I cost 12 $100 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.


Scott  07:41

So okay, so you 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 see if we can touch on any any any piece of that because I’m curious was you’d mentioned boiler room you mentioned SDR feel 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 for staff that you wanted to bring out that were just incredible things that you learned or anything like that?


Ryan  08:21

Yeah, I  can’t, I can give you a couple nuggets. I mean, and just for clarity purposes, I never was an SDR Oh, sorry, like SDR is was 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 closed 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 basically what happened with that that growth 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 found my way so you know, month nine got a big deal. Montana got a big deal month 11 and 12. Right so I was just a slow starter fast finish that with that. Then I continued over the years did the same thing. Right. And basically what happened was I got sick of working 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 like Matt is.


Ryan  09:51

And, you know, I’m sure there’s some other shenanigans that he was doing but 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% according he hit every year, roughly about 130% of it came from like to do yoga, and stuff 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, 40%, 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, I was grinding away. And essentially, these things started to take off, but they shifted me departments. 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. Like just go figure it out. Right. Awesome. Sweet, right? So what ended up happening is I looked at that experience I had prior and I’m like, Okay, this is the track record, this is what they’re doing. So I started off like deconstructing all the big deals that our company had, 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, 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 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 deals might be $20,000 a month right here, one, well, the next year, we level it up and we got we started getting $70,000 month deals, then it was $150,000 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 in specifically focused and really hyper targeted on continually expanding and multiplying our biggest customers. And that’s how we’re able to be resourceful and get those results. That’s that’s an interesting, so


Scott  12:54

You were just now the name makes sense. You are going after the whales, the result you are going out to 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 sales development, I guess that’s the that’s the modern iteration of an inside sales rep for whoever is listening and trying to unpack those acronyms. So as you as you went through, you finally end up in this sales management position. You you sort of reverse engineer this process. This is the process that you use 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 run with it because obviously other companies need this, because they’re always hurting with these enterprise clients.


Ryan  14:05

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 and with customers, or customer facing components, but not with, with peers, I really other companies. I never with peers at my company. So I was kind of like in my own bubble. And that’s one of the biggest things I tell salespeople. It’s always, always, always talk to people outside of that. So what happened was, I started talking to folks as I was building my brand, and they’re like, what do you do? Yeah, cuz a lot of salespeople are competitive, but they’re like, so give me your baseball card. What are your stats? What did you execute on? Right? And then I started telling them like, Huh, that’s like really impressive. I’m like, it is they told 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, who 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 started to create a course for sales reps, not for companies, my company found out about it, they didn’t like it, it was the middle of COVID. And they say, Ryan, time for you 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.


Ryan  15:37

Yeah, it’s suck man, the 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 to myself, as a point of motivation, like Ryan, this is going to be a hell of a comeback story, there’s gonna be a hell of a redemption story. And so I did an enterprise summit last year, in October, when 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 I started talking to my network. And people were 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 for me before, we’re in a resource constrained environment where they don’t have tons of venture capital.


Scott  16:27

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, it’s too slow to bootstrap. And in 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 multimillion dollar customers without having to have venture capital and and put on this, like incredibly stressful growth trajectory that you always go on, when you take in outside money. So that’s also something is very, the fact that you brought that up, do you realize that a lot of founders deal with that? I think it’s quite respectful. So how is 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 proponent 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 what are your results, like, working with companies? So you make a bold claim, you say? How did you use 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 where you can go and implement. So walk me walk me through some of the results that you’ve actually had. What is your baseball card since you left?


Ryan  18:11

Yeah, sure. 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 at all, 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 doing something right. And what I’ll tell you, I’ll give you kind of the framework of kind of how I approach it. Would that be helpful? Scott,


Scott  18:41

It would be great. Yeah, I think that would be good. Because that’s, there’s two things that I want to speak about. I want to pull out of your mind as somebody quickly transitioning into entrepreneurship and how you did that. But obviously, the the sale system is also that’s key. Got it. We gotta go.


Ryan  18:57

Oh, yeah. Is that cool? Cool. All right. Awesome, man. So So basically, the way you look at it is there’s all the software companies that are being created, right. And I specifically focus on higher ticket companies. So companies that are selling solutions that are 30,000, or $40,000, 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 40,000 100,200 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 is all the software systems, all the software, I should say companies are being created tech companies are be creating, they spent all this time systemising the development of their software and the constant updating and an operating system for that, but they don’t create the operating system for sales. And so really, I look at that and like okay, what can you do to implement a sales operating system and there’s three components that I look at 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, they’re paying you $30,000 a month, the numbers add up really, really quick. A lot of times, too, if you focus on it, you can even double it. So someone’s paying you 20k a month, you can double it to 50k. It doesn’t take a lot of effort, where people go wrong. And the biggest mistake they make is they try and go from 20k a month to $200,000 a month. And 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.


Scott  20:48

So that’s the number  one sales off that piece. Do you do that? Do you recommend doing that with new products? Or like what’s the what’s the strategy to actually uncover that additional budget? Is it selling to another business unit within the company.


Ryan  23:11

This one is new, that new cost of Whales scale operating system, that’s the first one. So that’s net new customers. So the second one is what you just hit on is a secondary sale system, or a secondary sales process. So and basically that’s, that’s expanding existing customers, that the 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, they’ll 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 sitting in a room I was at a conference. There’s 5000 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 to less than 4% of the room had this in place. He’s like that’s the 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?


Ryan  24:51

It’s a system around customer to customer referrals. If you look at Dropbox, Dropbox literally grew from 100,000 users to 4 million users in 18 months because of a referral system. Interesting. That’s the main source of it.


Scott  25:13

You’re right, I think a year and a percent right now, but nobody really focuses on that. Right? Yeah. So


Ryan  25:20

that’s, that’s, that’s a specific example. There’s another company that I know too, this is an out on the web or anything like that. But essentially, they grew from 1 million to about 5 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,


Scott  25:54

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 on 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 a How do you build an entry? What’s the Dropbox, you know, the dropbox example they, how they built it.


Ryan  26:23

That’s super, super simple. And I’ll give you this as a takeaway, but then I’ll give you kind of like the high level framework of, of kind of how I view it or approach it. But like all Dropbox did is they included in their implementation, you know, seven steps to implement it and get started. And step number seven was, if you refer to people, you’ll get an extra 250. Meg’s of space. That’s it. So that’s, that’s a, that’s a real simple one. Now, granted, that’s on a lower ticket $99 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 use to basically explode that platform, that social media platform. So I use the behavior design file from that to make it super and 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 a team’s perspective. And then also I live, 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 Steele Dini, his book, persuasion, persuasion, or influence that persuasion persuasion, yeah. So the reciprocity principle, which is number one, is the idea. And I love this example, because it’s so simple everybody gets it, is that you know, when you go and you go to a diner, or you go to a restaurant, and your waitress comes, or weight or columns that are like, Alright, here’s the bill, before that, the ones that give you something, get a 70% 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 realized 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 they’ll depth and then you got to make it easy for him. And then they’ll give you those referrals all day long.


Scott  29:05

That’s, that’s very, very smart. So this is the three part this is a three part system that you 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?


Ryan  29:21

Yeah. And so in in full transparent, I’m not working with billion dollar companies on this right? No, fair, fair. Yeah.


Scott  29:27

So just a little bit more agile.


Ryan  29:29

These are people that are selling to enterprise companies selling to big deals, I should say. So. So it’s a no brainer. 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. It’s insane. And it’s even backed by HubSpot that 99 92% of things maybe 84 it’s 84% I believe 84% of new purchases. Start with a conversation from appear. So I have put some gasoline and accelerate that. Right? Yeah. So the three months and what you’re asking about that is basically it’s, it’s, it’s the way you look at it. And when I work with folks, I’m going to start to, to codify this into a course in 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 gotta do your 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 it’s really looking from macro to micro, what is that company specifically doing? How are other processes systems 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 respond to. So look at it from like, assessment to execution is kind of how I approach it.


Scott  31:06

I love that. I love that. Okay. Now, I know 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. Every day, but that’s okay. That’s okay. Whatever you saw some. So it’s been like, Okay, a couple months? Um, no, I was gonna say so. 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 we didn’t go into? Because you gave a really nice summary, but I didn’t want to cut cut anything out?


Ryan  31:50

Well, yeah, I mean, I’ll give him a micro I mean, long story short, is, there’s a lot of complexity to really big deals. 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 it does 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 a really big companies because there’s an art to it. So something anything, anything else about me that’s just a little advice or tip.


Scott  35:00

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


Ryan  35:24

No, because I don’t believe you should do that. Right. It’d be like, 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 forced apps 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 um, so 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? Do you want to start going up market have 30% of them be enterprise, even over 50%? And being mid market and maybe 20%? being small, medium business? It all depends on your business? Yeah. But for if you’re mid market and enterprise, you do a 7030 split to start, and then it could eventually move to 5050. Because then you have the lawns and then the short and medium wins to for cash flow purposes.


Scott  36:20

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 what were the steps you took?


Ryan  36:37

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 gonna, I’m gonna 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 gonna 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 burned my boats. I mean, in dude, I’ll tell you, man, whenever Sam, it was really hard. And I told this to anybody that also your folks are first thing here, but a sense of vulnerability. Like, because it’s not it’s not a wound anymore. It’s probably more of a scar. But I remember, like, was not a good day in this daily household. My wife was like, What are you gonna do? You know, she was upset, my son thought that she played in band at the time, and I loved the little guy. He’s like, Dad, am I gonna have to play my saxophone for money, like we get kicked out? You know, it’s funny. Now. However, it was gut wrenching to see like my family, all that in decisiveness. So I just started chipping 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 I worked a lot of hours there. 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 the I made, the mistake that I’ll share with you listener is that I tried 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 can think about scaling later. So that’s, that’s my advice. And that’s, that’s kind of, you know, where I’ve gotten to and I’m out of the thick of it now and things are exciting.


Scott  39:08

That’s amazing. And that’s good for you. It’s very good for you like Susan gratulations that’s not easy. And use a you found this you found that this is you know, you had your product that you proven out that has worked and then you just sold it you sold this strategy to businesses and now that when did you close your first deal as an entrepreneur? Was it month five? Yeah, what?


Ryan  39:31

So I started having people it’s funny because I started having people want like, want me to coach them on how to sell because I help sales reps like I helped one person increase their income from never been in b2b sales, almost like 500k and like a couple 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 from my network told me, I want you to help me with this. And then I had someone else from a referral, tell me like, hey, like, I want you to help with this. 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 solid 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.


Scott  40:50

And right. And right now as it is, it’s still you that the acid go in and teach, or are you are you starting to course defy this? Because you said you’re trying to do that? Yeah, so


Ryan  40:59

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 gonna have some some new offerings coming out very, very shortly. So I’m excited that I’m gonna have a course, it’s probably gonna 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, that a person who is spending 25% of their time, there 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 once you start to see results like that, you’re like, Okay, there’s nothing here. I got to share this with


Scott  41:50

people. Very good. Then I’m curious, because you’re still like, you’re still living at what was the biggest? What was the biggest misconception about entrepreneurship and building your own business that you had going in, that you sort of matured on over the past year?


Ryan  42:08

Yeah, one of the biggest things is I waited too long to leverage other people and smart. You know, I tried to lone wolf it and with my pride, and my I’m gonna figure this out, this is what I’m gonna 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 that would have massively accelerated, like, where I was going, and how


Scott  42:31

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?


Ryan  42:39

Right? Yeah, I had 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 it be with your content, whether it be your your podcast, development, whether it be leads, I mean, there’s so many different things.


Scott  42:54

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 the classic like first time, I don’t even know his first time just classic person who’s never scaled before problem. They just feel like could do everything themselves.


Ryan  43:08

Yeah. And that’s, that’s, I mean, that’s a match. 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 danfo?


Scott  43:19

I did. It is a familiar name, but I don’t, I’m not placing. Maybe I’ve seen it in the past.


Ryan  43:25

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.


Scott  43:42

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 your business going forward? Or did we cover most everything? No,


Ryan  43:55

ma’am. 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 podcast as well. Sales and Marketing built freedom.


Scott  44:08

Nice, very nice. Okay, good. All right. Biggest challenge you had in your entire career. How did you overcome it?


Ryan  44:15

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.


Scott  45:01

What would be one thing you would tell your 20 year old self? I have a 20 year olds, not even my 21. So I can’t even drink yet in this scenario, right? I know you’re still responsible, because then the lessons go downhill once you start drinking for the next five years, so don’t.


Ryan  45:17

So here’s what I would say is like, early, early, early on my career, one of my one of the beautiful gifts that I got from 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 that who those people are, what do they look like? What do they believe, and reverse engineer that and you can do anything and really fast time. And it took me a long time to figure that once I figured that out. I mean, things took off like a rocket.


Scott  45:56

Good advice. Very good advice. You just touched on this, but I’ll see if you get a different answer. The the person or people who have been really influential in your life, what did they teach you?


Ryan  46:09

Yeah, I mean, you know, my parents, and my wife, Mike is just just being loving, and putting your heart out there and just being supportive no matter what the situation. And that’s, 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 side, Scott, you know, so. Okay. So that’s what I would say is just people being there for you in situations where you really, really need them.


Scott  46:39

Okay, what’s a podcast or a book that you’d recommend people to check out? Besides all the ones you already recommended?


Ryan  46:47

I’m dropping stuff left and right. Okay. Can you have two books? Is that cool, man? So I have like a little recency bias. But one book that’s really good for exponential thinking, is a book called u squared. Have you ever heard of u squared? No, I don’t know that these are new to me. It’s only 36 pages long. And it’s it’s one of the most thought provoking books that a mentor of mine recommended me to read it every single week. Because it 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 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 inspiring people at an emotional level. And I think it’s, some of the stuff is really beautiful. And what he did, I know he gets painted as like a kind of a jerk or hardcore guy, but there’s some amazing things that he did that could help you if you’re interested change the world.


Scott  48:05

Um, what does success mean to you?


Ryan  48:12

That’s a good question, man. And I have the Type A achiever where it’s like, I gotta 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.


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