S4E29 Ryan Staley 5 Powerful Lead Gen Strategies for B2B SaaS Sales

S4E29 – Ryan Staley – 5 Powerful Lead Gen  Strategies for B2B SaaS Sales
Ryan Staley – 5 Powerful Lead Gen Strategies for B2B SaaS Sales. My next guest is an experienced B2B SaaS sales executive who has helped companies go from $0 to $30M in ARR. In this episode, he talks about 5 powerful lead gen strategies and 1 powerful closing strategy for B2B SaaS sales. Please welcome, Ryan Staley.

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Key Timecodes

  • (00:37) – Show intro and background history
  • (02:03) – Deeper into his background history and business model
  • (04:46) – Podcasts value as a networking tool
  • (08:14) – Understanding his B2B business strategies
  • (16:00) – Deeper into his B2B tactical strategies
  • (19:00) – Online meetings X in person approach to close deals
  • (21:26) – Some strategies to close big deals
  • (25:39) – His thoughts about the AI and the business market
  • (30:52) – A guest takeaway about B2B selling
  • (34:27) – What is the worst advice he ever received
  • (34:51) – What is the best advice he ever received
  • (36:52) – Guest contacts


[00:00:00.320] – Intro
Hey, this is Sean Tapper, the host of Payback Time, an approachable and transparent podcast in building businesses, increasing wealth, and achieving financial freedom. I’d like to bring on guests to hear authentic stories while giving you actionable takeaways you can use today. Let’s go.
[00:00:17.290] – Sean
My next guest is an experienced B2B SaaS sales executive who has helped many companies grow from $0 on up to an over 30 million in annual reoccurring revenue. In this episode, he shares five powerful lead gen sources and one powerful closing strategy. All right, let’s get right to it. Please welcome Ryan Staley. Ryan, welcome back to the show.
[00:00:39.740] – Ryan
What’s up, Sean? Happy to be out here again, man.
[00:00:42.200] – Sean
Good to have you here. So why don’t you kick us off and tell us about your background for the listeners that don’t know who you are.
[00:00:47.890] – Ryan
Yeah, so super quick background on me. I guess if you look at my career, everything has been evolved around revenue growth. So started off, I had pretty much every single crap job you can have in sales, specifically in B2B space. I had B2C before, but B2B moved up the ranks, mid-market enterprise, and then did the same as a leader. So grew from underperforming units into top performing units, grew a business We’ve seen it from zero to 30 million in ARR. And five and a half years with only four salespeople, we didn’t have any marketing, we didn’t have any SDRs. And so effectively, what I did is once I left that company about three and a half years ago, I started helping companies implement the same strategy strategies to their business. So how to hyper scale without having investment or PE from the strategies and tactics that I used to do that. And then over the last year, I’ve been obsessed with AI and how to integrate that into sales and marketing so you can hyper scale yourself even more than what we did before. So that’s where I’m at, man. I have a podcast just like you called The Scale Up Show, where I share tips and tricks on AI and sales and marketing, as well as interview top tech founders And then, yeah, that’s what I’m focused on right now, man.
[00:02:04.120] – Sean
I love it. And with that previous episode, this is going back. This is actually season one of Payback Time I had you on. We talked about that journey of going from about zero to 30 million ARR. And I think you, at the time, just left your last corporate job, and we’re going full-time with what you’re doing now. So I was listening to you talk to Myron Golden. Listeners out there, if you don’t know who Myron is, this The guy’s a sales expert. He’s very good. And you guys had an awesome podcast there. So I recommend checking that out. But you mentioned you grew your business by 300 %. So I want to talk about that a little bit. Then I’m going to talk about SaaS sales So we’re going to talk about strategies because I’m big on SaaS. And I’m going to lead up to some AI discussions at the end. So why don’t you tell us, how did you grow your business by 300 %?
[00:02:52.940] – Ryan
Yeah. So I think… And this is something that’s been prevalent over time. It’s really interesting because the whole AI my ship, I completely pivoted my business. So that was effectively through consulting. So I started in 2020 in the prime middle crappiest time of the pandemic. Right before the point where people started washing down their groceries and stuff like that, it was right before then, which is always an interesting time. And so started off at first, I was just trying to figure out what the hell I was doing and what I wanted to do and who I wanted to serve. And I had ideas because I had this deep well of expertise in sales. And so what happened was It was funny because I just started meeting with people. I was looking at working with sales reps and then sales leaders. And what started gravitate people towards me is when I told my backstory on what I did. And people were amazed, that zero to 30 million in ARR Because that’s something that VC back companies will do, but they will have 30 people doing it. And they’ll have tons of cash they’re throwing at. I did with four people in a red ocean market that was highly competitive.
[00:03:58.500] – Ryan
So it wasn’t like I was selling the next sexiest thing in first of the market or anything like that. I didn’t have a Tesla as it came out. And so what I kept doing was I just kept reaching into that and looking at folks in terms of how I could serve them. I kept refining what I call my perfect customer profile, which was the top 20% of my ICP. So if you look at it, the best of the best in terms of profitability, revenue, as well as time to close. And then I focused on that deeper, integrated that actually into my podcast because they started getting companies that wanted to work with me that were guests on the podcast, and then basically converted that into new clients. So that’s how it happened. I mean, that’s a real quick summary of it, but from A to Z, that’s how it happened.
[00:04:46.280] – Sean
One strategy just highlighted there, which makes a lot of sense, is getting people on your podcast. Your podcast sounds like a lead gen tool. It’s not only a value add to listeners, but a lead gen tool. And then you have that warm introduction. And I assume from there, do you help… You bring them on as a reoccurring customer, introduce what you can do for them. Walk us through how that process works.
[00:05:09.520] – Ryan
Yeah. So it was one of those situations where that wasn’t my intent when I started the podcast. I love podcasts, personally, just like you. And so I’m like, All right, I want to do this. But what started happening on accident was that I started interviewing my prospects, and then it naturally started to happen where people were like, Hey, so what What exactly do you do? Walk me through that, right? Because they enjoyed the experience. They liked that I was promoting them. And then I’m like, What happens if I start to lean into this, right? And so that’s what I started to effectively do. I’m like, yeah, I’m going to actually focus on this, have the right people on my podcast. So it was really good because I covered so much ground, had access to anyone. And then you look at it like what happens effectively when you’re… If you think of it, it’s rooted in human nature. So a lot of folks will reach out now. They’ll leverage a spam canon of a sequencer of shitty sequences and try and get meetings with executives, whereas I can send out a sequence of emails inviting guests that fit my exact target and profile of people that I think would be good to have on the show, not just for potential clients, but also for the listeners, right?
[00:06:18.770] – Ryan
And the hit rate was amazing. I think on average, the response rate was probably 35, 40 % just from emails sent out. And then what happened was I just interview them, understand about their business, their journey, where they want to go and the outcomes they want to create. And then often that segue into things that I can help them with. And so that’s how it all went down. It was pretty seamless in nature. And there’s actually a couple of companies that I’ve helped with this. One of them, it was a founder, and basically she had about a $2 million company. I met her at Saaster, and she’s like, Hey, Ryan. She’s like, One of my biggest issues is pipeline. I don’t have enough pipeline. I don’t have enough prospects. And so I I said to her, I’m like, What are you doing on the content side? What’s your approach to that? And I walked her through and basically did an engagement with her where I helped her set up her pipeline, create that not just as a front-end pipeline engine, but also a content machine on the back-end. And she got close to a half million dollars in pipeline before she even launched her show.
[00:07:21.690] – Ryan
Got access to group presidents of Walmart and 711 in different countries. And those are people she wouldn’t have been able to access. And so that’s just an example of what’s possible. I’m now actually, it’s funny, had a couple of other companies reach out to me that are larger in scale and really want me to help them do this because if you have a large ACB, it’s like fishing with diamond. It’s one of the hardest things in the world is to get pipeline with high ACB prospects. But this is a mechanism to do that. And so it’s something that I would highly, highly recommend leveraging if that’s your space. Yeah.
[00:07:55.790] – Sean
To touch on some of the acronyms here, ACB, annual contract Contract value?
[00:08:00.930] – Ryan
Yes, correct. Annual contract value, sorry.
[00:08:03.400] – Sean
And then ICP?
[00:08:05.660] – Ryan
Ideal customer profile. Got it. Bcp is perfect customer profile. So think of that as- Got it. Like, if Pareto’s principal had a baby with your ideal customer profile, that’s what your perfect customer is.
[00:08:15.970] – Sean
Well put. All right, so just a pause point here. I do like to talk to the audience a little bit. So Tykr is a B2C SaaS, and we don’t have to or I don’t have to jump on Zoom calls or do presentations that get people into the platform. B2c is very low touch. You want people to trying it out. Netflix is a great example. Duolingo is another good example. But where Ryan plays, his space is B2B SaaS, and that’s a different animal. You can’t just put up a site and add a lead magnet and people are going to be coming in and buying. You have to. We’re talking bigger dollar amounts here. So people are going to be spending more money, which means you got to work as a consultant and walk them through the value So Ryan’s specialty, again, is that. So I’d love to dive in a little bit on touching on how do you help companies because your business is whalesellingsystems.
[00:09:10.910] – Ryan
Com. It’s actually, it’s rianesdaily. Io. My company is WhaleBoss. So I did that email domain, specifically, so I wouldn’t get hammered as much with the spam and outreach. You know what I mean? People just copying it. So that’s been effective so far.
[00:09:27.500] – Sean
Lesson learned there, create a really long an email, so it’s hard to copy. That’s awesome. All right, so let’s dive into, how do you help companies generate more leads for B2B sales? And then we’ll transition to, how do you help them close more sales?
[00:09:43.170] – Ryan
Yeah, so I think there’s multiple There’s a lot of ways to do this, and this market is exponentially changing over the last few years. So if you look at all the external pressures, the model of SDRs is dead, in my opinion. There’s still use cases, but the one size fits all, have A sales development rep, reach out, make calls, send a ton of emails. That is a dying breed, and there’s multiple reasons for it. There’s more and more barriers than ever before that existed to prevent that from happening. There’s a lot of other ways to do it, which I think are highly more effective. The number one thing that I would look at, though, whenever you say leads or pipeline, is it always correlates back to your annual contract value. Because So what you mentioned with B2C, it’s very simple to get someone to hit on a website. Not very simple, I should say. It’s a different process. It’s not simple. It’s a different skill set. But to attract folks or to leverage influencers or joint ventures to do that and get them to try your product and use it. Versus trying to get access to a C-level executive at a larger company.
[00:10:56.040] – Ryan
I mean, you used to be at a larger company, right? You know how it works in the executive position. It’s a much different place. So your options for that are outbound, like I mentioned, is one of them. I like referral-led growth is one that I think is really strong, that’s massively underutilized. And so effectively, that’s systemizing customer to prospect referrals through your client base, which you’d be shocked with how many companies do not do that. It absolutely blows me away because referrals close in 75% of the time at 125, 150% of the close rate. So it’s It’s literally insane. Podcast is a pipeline, one of the things that I mentioned there. And then the third one that I believe strongly in is effectively, and these are all non-AI related, by the way, you can integrate AI into them, but they’re not relying on it. There’s community-led growth, so you could effectively work in a community where your ideal customer profiles are, answer questions, be helpful, and then you can convert them into a Slack community. You can do that and convert them into appointments. You can do it via social, leveraging the same principles within there.
[00:12:06.280] – Ryan
Then last but not least, one of the things that I think is often missed, if you look at outbound or targeted prospecting, is there’s so many associations, groups, or centers of influence that are out there. One of the things I think is often missed is effectively, if you target those groups, you got to find them that have the exact niche of your customer, not just your general space. So for example, I would look for something. If I was targeting CIOs, I would look for something that’s targeting the CIOs within the specific verticals that we had and with the exact type of clients we want. Pursue them, ideally get a board member of that group as a customer, and then push that out. So that’s how I would approach it in a real quick snapshot.
[00:12:55.120] – Sean
I love that strategy. I’ve thought about that. Here’s another example would be, let’s say you’re selling a cyber security product. And I talk about this with my audience, especially in your investing in stocks. I really like cyber security. This is not financial advice, but Fortinet is a stock I hold. And the contracts can be hundreds of thousands of dollars and up to millions of dollars a year. You’re not going to sell that with one email. It’s like you got to get people on a call. But how do you get in front of a whole bunch of businesses you can be part of a cyber security association? And it could even be niche down into to, let’s say, cyber security for manufacturing or for pharmaceutical and get in front of the board and say, Hey, I have a product that can help these people. And that can be an easier process than trying to knock down doors.
[00:13:46.570] – Ryan
Oh, without a doubt, man. I call it vertical to horizontal, right? And it was funny, like real-world example, a company, I don’t know, they’re about 30 million. I was working with them. They had 14 different verticals that they focused on because they had a horizontal solution. However, we found that 86 % of our last three years revenue came from three verticals. They had no specialization. It’s just what they did was especially unique and valuable for those verticals. So I’m like, hey, what do you think would happen if you focus instead of dispersing your time across all 14 of these verticals? What happened if you focus the majority on these three? Do you think that would be valuable? Everything from enablement to track to events like you mentioned? And yeah, because I We did it, and it helped us double our deal size every year, and then 100X our largest deal size when you do that.
[00:14:36.120] – Sean
I love it. Circling back to the number… The first strategy you mentioned, outbound. When I think of outbound, I think of Alex Hormozy is big on calling. His reps, part of his companies, have to be making 200 calls per day. Is that what you’re talking about? Is that consistent calling?
[00:14:54.070] – Ryan
Yeah, it’s calling. I think it’s a little different because he’s his dollar value for what they’re selling, it’s like… Well, I guess it’s… I’m trying to think of his old company, Jim… What is that, Jim Launch?
[00:15:08.590] – Sean
Jim Launch.
[00:15:09.500] – Ryan
Jim Launch. That’s what it was, right? Yeah. Acquisition. Com is probably different because of the fact that there’s They’re trying to access CEOs that aren’t hanging out on social as much, right? Sure. So I would imagine it’s a combination of calling, emailing, engaging on social. There’s a lot of different ways to engage people. But I would classify it in that bucket.
[00:15:31.870] – Sean
Got it. Okay. I’ve got five here you listed, and you can correct me if I’m wrong here, my note-taking ability, but I’ve got outbound, referral-led growth, podcast, community-led growth, and associations. Is that broken down correctly?
[00:15:45.960] – Ryan
Yeah, it’s perfect, Matt. And then often the sweet spot is when you integrate multiple- Sure. Strategies or multiple levers. The level of maturity that you’re at in the business depends on which one you want to pull first, in my opinion, right? So that’s That’s how I would approach it.
[00:16:01.320] – Sean
I love number two, which is the referral-led growth. And I assume a conversation would be with a current customer, and you’re going to raise the question, do you know anybody else that is in your line of work that would be open to a conversation? Do you pitch it like that?
[00:16:18.990] – Ryan
There’s multiple ways to do it. I think there’s a lot of affiliate models and referral programs for lower-end dollar spend. What I I’ve discovered and why I started to focus on this is because we got… When I was a revenue leader, we got $20 million deal from Whole Foods, Amazon, from a referral from a deal we didn’t even win. That’s how we got into the opportunity. And so Once again, with the podcast, I’m like, What would happen if we just leaned into this? Or a company that’s got 500 customers, what would just happen if you leaned into it? It’s like that fishing with dynamite or bringing a gun to a knife fight. Those are the things that happen. And so most people treat referrals as an event instead of a process. So just like you have a sales process with multiple steps that creates the end result versus a one-time like, Hey, will you buy this shit? Same thing with referrals. That’s a piece of it, but you also have to integrate What’s the right time? What are the emotional peaks that the buyer is having? Because they do go through ups and downs, just like a relationship or a marriage, where there’s ups and downs.
[00:17:25.870] – Ryan
Asking them in the right way at the right time, and then giving them incentive that is genuine and doesn’t make them feel dirty. Because as you know, we’re going to be in a company before there’s a limit. Sometimes there’s a 50-hour limit on what you can accept as a gift because of policy. So there’s ways around that. You can donate to their charity, You could give them information instead. You could have them be part of an exclusive mastermind within your own company. So there’s a lot of different ways you can leverage it from an incentive structure.
[00:17:53.720] – Sean
Got it. I like that approach, the referral strategy, a bit more than outbound. That’s not my jam, but I know some people are good at making those calls.
[00:18:03.710] – Ryan
It works really good. It’s one of those things that, just like anything else, it requires work. And most people think, as Hormozy would say, they think there’s a silver bullet when it’s really 100 Golden Beebies, right? That you need to execute on it. And just with any other, just even creating content, doing a podcast, anything that you can think of, it’s not you just show up and then it just starts raining like a hurricane. It requires work and consistency consistency and optimization over time to get you there. Now, granted, there are better paths than others, but that’s the way it is.
[00:18:37.250] – Sean
I like how you phrase it. It’s not an event. In other words, one ask, it’s a process. That’s the key right there because I see so many people making the mistake as they ask once, Well, this strategy isn’t working. Well, it’s more than just asking once. It’s a process. And as you said, you hit them in those peaks and valleys where their emotions may be high one day, low another day. How do you work through that over time?
[00:18:59.550] – Ryan
Yeah, exactly. Cool.
[00:19:01.140] – Sean
All right, we touched on lead gen. Let’s go to the end of the equation here, which is closing. I assume in this world, post-COVID, you’re trying to coach your customers on doing a lot of Zoom calls or team calls. Is that correct?
[00:19:15.610] – Ryan
Well, those happen anyway. I don’t need to coach them to do that.
[00:19:18.510] – Sean
As opposed to phone calls?
[00:19:20.290] – Ryan
Yeah. I think I would take it one step further, and especially with larger deal sizes or even mid-market deal sizes. Their There was a study done on this. Did you see the study done on Zoom versus in-person reactions?
[00:19:34.540] – Sean
I did not.
[00:19:35.750] – Ryan
I think there’s like, damn, I wish I would have saved that hard call. I got to look at it. But there’s close to, and I think a 70 % higher level of stimulation in a person’s brain when they had an in-person interaction versus over Zoom. It was related to the neurons and your brain and the attention levels and all those different areas of when you had an in-person meeting. And so I think, and here’s a prime example, there’s folks that I met with, they were local, and always met with them virtually. And I’m like, why don’t we get together? We’re close to work in business together, went up, met up with them, was an It’s been an awesome experience. Got to know them at a completely different level versus a Zoom meeting, which is often time-blocked of like, okay, I got this one, then I got the next one, then I got the next one, right? And so that in-person meeting allows for variability. And it could be coffee, it could be food, it could just be a sporting event, or it can just be just physically meet with them for a live meeting, and it’ll be transformative, which so many people are ignoring right now, which is crazy.
[00:20:43.700] – Sean
So does that mean we switch back to a mode where we’re jumping on planes and meeting people in person?
[00:20:48.960] – Ryan
I think there’s a hybrid, right? I think it’s so funny because before it was like, I’ll jump on planes and everything like that. A lot of the virtual meeting stuff sucked because we tried to use it for a while. Then it’s gone to all virtual meetings and people dread being on back to back to back to back Zoom meetings, right? It actually drains your soul if you do that and ages you, which I actually believe it does age you. But I think there’s a good balance, right? You can qualify shit up front by having those Zoom meetings and make sure it’s a really good opportunity. And then once it’s focused in, go do the live stuff. I think that’s still really critical and important.
[00:21:26.690] – Sean
Love it. So we teed up closing. Let’s Let’s dive in a little further. What are some strategies that work really well for helping close sales, especially the larger dollar size? Yeah.
[00:21:37.540] – Ryan
So this is one of my favorite ones, and I would love your feedback if anybody ever leveraged this with you. When in your prior corporate life, right? So what I would say is that the big one for me is, I call it a reverse close. So effectively, once you get to the end of the process, if you look at it, we got what I say is a strategy meeting, which is strategy meeting is more like a run. So that’s making sure if you have a complex sale that all the variables that you’re making assumptions on are there. The ROI is clean, the buy-ins there from alignment across multiple different buckets, budgets, and departments. And Everything’s working in unison. So once you have that, basically you’re getting verbals on everything and you’re tightening up the last few pieces of the buying process. So that’s that meeting. When it goes to proposal meeting, most people don’t do that strategy meeting. So I think that’s one of the biggest mistakes people can make. Then when we look at the proposal meeting, what happens is you go through there and reverse close effectively is like, Okay, we agreed to this.
[00:22:43.970] – Ryan
You basically identified, and you start from… I should say, let me take a step back. You start from the end and work backwards. So what you want to do is understand from the potential buyer, when do they want to implement? Not when do they want to sign the agreement, but when do you When you want to start implementing this, what would be a target date that you have for that? Say it’s February, right? So if it’s February, then you work backward and say, Okay, we need, let’s say, two weeks prior to implementing for onboarding and all that. So absolute latest, we need the contract signed by mid-January, okay? What are all the checks and balances on your end you need to go through prior to that agreement getting signed in terms of legal, in terms of board meeting approval, in terms of sign off? And what will happen through that process is you have an estimate of those dates for each one. You write them out on a sheet and then you talk through those. You have it on a PowerPoint slide and you say, Okay, implementation this date, signing this date, negotiation this date, as a business person, what am I missing?
[00:23:46.850] – Ryan
You have a dialog about it because a lot of times, buyers don’t really comprehend all the steps involved with it because there’s so many different areas. And so what that does is that basically brings any objections to the surface. It brings out if they’re not ready. They’re not quite where you thought they were going to be. And so then it makes it really simple, transparent, invisible to what you need to do to make that happen as a reality while covering all the objections at the same time.
[00:24:12.050] – Sean
Gold. I appreciate that. That is awesome. I love it. I know people selling B2B here are going to be like, Okay, all right, I have to do that. So that makes perfect sense. And I’m actually, because we’re in a growth stage here with Tykr, I’m on the receiving end. So that strategy just walked through. There’s a sales guy I was on a call with, with a marketing agency that was literally doing not the same what you walked through, but pretty similar. I’m like, I see you. See what you’re doing.
[00:24:43.310] – Ryan
That’s awesome, man. Good for him.
[00:24:45.930] – Sean
That’s awesome. Let’s take a quick commercial break. Do you feel like stock investing is too confusing, too time consuming, or too risky? It doesn’t have to be. If you ever considered investing on your own, but you don’t know where to start, I welcome you to check out Tykr. Tykr guides you through your investment journey by steering you towards safe investments and away from risky investments. There were two main reasons why I created Tykr. Number one, I wanted to remove emotions from investing. In other words, I wanted a software to make buying and selling decisions for me, so I don’t have to. Number two, I wanted to save time. Analyzing stocks can take hours, if not days, and I didn’t want to spend all day looking at the computer. I have other hobbies in life I’d rather be enjoying. Playing. If you’re interested, you can get started with a free trial. Visit tykr. Com. That’s T-Y-K-R. Com. Again, tykr. Com. Let’s transition to AI. Since you’re spending a lot of time on artificial intelligence, what are you doing to maybe help your own company and then help your customers?
[00:25:50.390] – Ryan
Yeah. So internally, I’ve created what’s called the prompt matrix. And I have my team and myself doing work that would never have been possible without this. And so effectively, the way I look at it is you look at a lot of the AI products out there, 95% of them are built on top of the large language models. Now, there’s other ones that are, it’s probably maybe 90% now, but they’re built on the large language models. And so my view is if you truly understand and own and understand how to dominate the large language models in terms of usage, then you could arbitrage the other $10,000 a month you would need to spend by just understanding the core foundation of it. And so I’ve done that from pretty much I use it in every part of my business for an AI-first business, all the way from content creation to strategy to time to to execution, to arbitrage money. All those areas I leverage internally. And so that’s how I approach it. Like I said, it’s not just sales, it’s not just marketing, it’s operations, strategic thinking, product, everything. So that’s how I approach it. Basically, what it is, is I leverage best in breed prompts that I could innovate on top of, categorize, have a library.
[00:27:09.590] – Ryan
And then basically what happens is, the beautiful thing about it, Sean, is now if I want to execute something, I have it set up, so I just type in one word and it has a very long involved prompt that executes for me so that I don’t need to do it. So I not only prompt and understand how to do it better than 99% plus of people, but I can now do it 95% of the way faster. And then I just keep innovating on top of it. That’s what I do for my company, and then I’m doing the same thing for other organizations, helping them with their revenue function, because literally, BCG Consulting did a study with Harvard, and you could effectively 200% the output of people by doing this when you span it across quality, quantity, and speed. And so that’s what I’m helping companies do so that they could create asymmetrical exponential results. It could get implemented in a week or two weeks. Sure. So, yes, that’s what I’m hoping companies do. And I have the sales AI accelerator to help companies or individuals do that on their own as well if they want.
[00:28:07.200] – Sean
What I’d like to do is just go a layer deeper to give a tactical example of what that looks like. I know this might be part of your service offering, so don’t give the whole recipe away. That’s okay, man. But let’s walk through an example of how this works in practice.
[00:28:23.950] – Ryan
Yeah. So I look in five categories: time, execution, admin, money, and skills. Those are the category buckets that I think you can leverage it for. And so I’ll give you a couple of examples. If you look at it through a jobs to be done structure, what are people actually doing on a day to day basis? An example, let’s say for sales is something that took 15 minutes and you do it, I don’t know, 15, maybe 20 minutes or a half hour. Let’s say it does a half hour and you do it daily. If I can cut that to a couple of minutes, that’s a lot of time you’re getting back in your week. And that’s just one task. So if you look at sales or marketing or a lot of jobs, think of it. Remember when we went through the industrial revolution where folks were doing everything by themselves, like hand digging everything, and then we started operating machinery to do that for us. The weird thing is we’ve gone through that same cycle again where white collar workers are doing everything with all these minutia tasks, all these tiny tasks, and it’s death by a thousand paper cuts.
[00:29:27.730] – Ryan
If you leverage AI, you can have the same transition that the industrial revolution had, where instead of doing the white collar task like we did before the industrial revolution, we’re now doing that on the knowledge worker side, and you can let AI leverage and do a lot of that for you. That’s one example in terms of time. Another one What I look at is more of a deep work function. I actually did a post on it on LinkedIn, effectively, and I’ve talked about this on my podcast, The Scale-up Show. But what I created is a whole entire sales organization in 20 minutes. So effectively, what I did is identified what the comp structure would be for a team that I was hiring, what the KPIs are evaluated on, how to manage them on a quarterly, monthly, weekly process, how to create a tech stack for them for under $1,000, and then how to create a job description to actually hire them. I did that all in 20 minutes. That’s like a deep work application you can leverage for this as well.
[00:30:20.580] – Sean
That is incredible. Great examples. I love to tie back to the Industrial Revolution and how we’re facing the same issues today. I have experience within the insurance space. And there are so many repeated steps done over and over manually. And it’s like, I remember asking this question five, six years ago. Isn’t there a better way? Can’t we use AI to make this easier.
[00:30:47.330] – Ryan
You’re on the forefront. You’re talking about five years ago, so makes sense.
[00:30:51.880] – Sean
No, this has been great. Before we jump to the rapid fire round, is there one great takeaway you can give to people selling selling B2B?
[00:31:01.260] – Ryan
Yeah, I think it’s hard right now for a lot of folks because there’s a massive influx of tools, especially with the whole AI revolution. I mean, it’s exploded in the number of tools. So I think the number one thing if you have your own company or you’re a seller is become a master of getting attention. And it takes work, but there’s a deep well of building your own show and creating content. It’s organic that people want to hear from, that’s valuable to other folks. So it’s effectively the product-led growth approach of attention. And so no matter what space you’re in, what type of company you have, if you’re in B2B, those are table stakes right now. And a lot of People are still not doing it. They think if they spam out hundreds of emails a day, it’s going to make that happen, and it’s going to get worse and worse with that. And because of the new restrictions with Google has and some other email providers, It’s going to disrupt a lot of companies. So I would say focus on that, and then that’ll take care of everything else, right? So that’s the number one thing.
[00:32:08.550] – Sean
I love that advice. I’m actually starting to see people who are not just business owners, but people who work for companies that are starting their own podcast to help really solidify that what you just said is become a master at getting attention. And it’s like you take this personal branding, which you’re building up this moat around yourself, because not everybody’s going to start a podcast and stick to it. But a company may want to hold on to you longer. They may elevate your value within the company, and other companies may see you and be like, I see what you’re doing there. Hey, we’ve got an offer for you. Conversations could go that way. It’s cool. I just met a guy this week that, not a business owner, but started his own podcast and helps promote the products within the company he works for. I thought it was a brilliant play.
[00:32:56.750] – Ryan
Yeah, sharp, man.
[00:32:58.230] – Sean
Cool. All right. Well, let’s We’re going to transition to the rapid fire round. This is the part of the episode where we get to find out who Ryan really is. If you can, try to answer each question in about 15 seconds or less. You ready?
[00:33:09.860] – Ryan
Yeah, let’s go, man.
[00:33:10.980] – Sean
All right. What is your favorite podcast?
[00:33:13.150] – Ryan
I like Marketing Against the Grain from HubSpot. It’s got the CMO HubSpot and CMO Zapier on it. Really good stuff there.
[00:33:21.820] – Sean
Awesome. All right. What is a recent book you read and would recommend?
[00:33:26.130] – Ryan
So many, man. One of my favorites, I give this to the CEO, is around my show, it’s called The Gap and the Gain by Dan Sullivan and Ben Hardy. Love that book. It’s about measuring backwards to create momentum moving forward.
[00:33:39.280] – Sean
Nice. All right. What is your favorite movie?
[00:33:43.820] – Ryan
It’s funny. This goes back to my childhood. One of the first things that come to my mind is Goonies, which is an old-school movie. I would say that. You go more like, recent times. I really like Ready Player One. I thought that was cool. I don’t know if it’s my favorite, though, but they don’t make them like they used to, man. It’s tough.
[00:34:00.820] – Sean
We could go down a rabbit hole in this, but I was talking one of my best buddies last night. The amount of good movies coming out, it is few. And maybe it’s a sign of me, well, you and I, getting old.
[00:34:11.840] – Ryan
Yeah. You see so many, you get jaded, right? So I think that’s part of it.
[00:34:16.130] – Sean
To those that are not watching the YouTube version of this episode, you’re just listening, he’s got a Tommy boy picture behind him. Brilliant, brilliant movie. Thanks, man. Classic. All right. Next question Question here. What is the worst advice you ever received?
[00:34:34.110] – Ryan
Yeah, I would say, work for the same company, just put in your time and things will work out for you. That’s what I would say is the worst Especially now. Maybe that used to be true, but it’s not the case anymore.
[00:34:48.230] – Sean
It ain’t 1955 anymore. That’s for sure. It’s true, man. All right, flip that equation. What is the best advice you ever received?
[00:34:56.690] – Ryan
Yeah, I think it really When it comes to, and there’s a lot of things I could say on this, but failure is a requirement, not an option, if you want to build something amazing. And that’s probably accumulation of advice from a lot of CEOs I’ve had on my show as well as leaders I’ve worked for because I used to be afraid to fail and would do everything possible not to, and it helped me back in so many areas of life. So I wish I would have known that when I was younger.
[00:35:27.730] – Sean
100 % agree. I see so many people held back because of that fear of failure. It’s like you have to fail, fail forward, fail fast. My audience has heard me say that before. Sorry to be a broken record. What Ryan just said, spot on. All right, last question here, the time machine question. If you could go back in time to give your younger self advice What age would you visit and what would you say?
[00:35:47.620] – Ryan
What age you would visit is a good one, man. I think there’s a couple of things. If I went back to 21-year-old Ryan, there’s two things I would say. It’s like, don’t drink so much, right? From that perspective, you’re going to waste away a lot of your life. And then the other aspect was, and I wasn’t reaching out to Paul by any means. I just went out on the weekends and did that. And then the second aspect is, if you want something, don’t wait, go after it and just make it happen. You don’t need to be a certain age to do something. You don’t need to have a certain level of experience to be able to pursue something. And you build it along the way is the way I approach it.
[00:36:29.500] – Sean
Just to drill in there real quick, Ryan’s in Chicago, so he’s not too far from Milwaukee. Did you go to a state school in Illinois?
[00:36:37.860] – Ryan
I went to Millican, which is right by all the state schools.
[00:36:41.410] – Sean
Okay, sure.
[00:36:42.290] – Ryan
Eastern and UFI and ISU, and All of them, right?
[00:36:45.910] – Sean
The college life, those were the days. Not really, but an experience for that time. But anyway, this was awesome, Ryan. Really appreciate your insights, your advice. Where can the audience reach you?
[00:36:59.630] – Ryan
Yeah, Yeah. So you want to listen to my podcast like this called The Scale Up Show. If you want to know more about me, my content, what I can do, who I serve, I would say my website, rianstaily. Io. It’s going to get upgraded soon. But rianstaily. Io That’s always a good one. And then I publish on LinkedIn all the time with content that I discuss in terms of written content, like what I share. So definitely check me out on those channels.
[00:37:23.800] – Sean
Awesome. All right, Brian. Thank you. Thanks, Sean.
[00:37:26.350] – Outro
Hey, I’d like to say thank you for checking out this podcast. I know there’s a a lot of other podcasts out there you could be listening to. So thanks for spending some time with me. And if you have a moment, please head over to Apple Podcasts and leave a five-star review. The more reviews we get, especially five-star reviews, the higher this podcast will rank in Apple. So thanks for doing that. And remember, this show is for entertainment purposes only. If you heard any stocks mentioned on this podcast, please do not buy or sell those stocks based solely on what you hear. All right, thanks for your time.
[00:37:58.720] – Sean
We’ll see you.