Episode TL;DR
In this episode of Making Sense of Your Money, Dan Pascone sits down with Gabe Lullo, CEO of AlleyOop, to break down how founders and revenue leaders can build a real outbound engine. They cover why SDRs should bridge marketing and sales, how to take prospecting off your top closers’ (and founders’) plates, and what it takes to create consistent, repeatable at-bats so growth doesn’t depend on heroic quarters.
Key Takeaways
- SDRs are the alley-oop between marketing and sales. Marketing generates awareness and demand, AEs close deals, and SDRs sit in the middle turning intent into qualified meetings like the perfect lob that sets up an easy dunk.
- Your best sellers shouldn’t be your primary prospectors. Every hour an AE spends cold calling instead of presenting and closing is a huge opportunity cost. Offloading prospecting to a focused SDR engine can materially increase revenue with the same headcount.
- Founders already outsource everything else sales development should be no different. If you’re hiring agencies for your website, HR, and recruiting, it’s logical to outsource a specialized, always on outbound function too.
- Outreach must be intentional, not “spray and pray.” AlleyOop builds structured campaigns around a clear ICP, TAM, data from tools like ZoomInfo, and the right channel mix (phone, email, LinkedIn) with lead scoring and multi-threaded follow up.
- Volume quality comes from tech-enabled SDRs. With the right tech stack, AlleyOop SDRs can make 150-200 calls per day 3-4x typical reps while still targeting intelligently rather than just dialing at random.
- Warm, well-documented handoffs matter. They don’t just “drop a meeting on the calendar.” Prospects get reminders and introductions, and AEs get notes, call recordings, and AI transcripts so they can step into the meeting fully prepared.
- Consistency is the secret sauce. Like the gym, prospecting only works if it’s done every day. A “sometimes” outbound effort yields “sometimes” results, which is why an always-on SDR function is so valuable.
- Salespeople are mini-entrepreneurs. The best reps think like business owners inside the business embracing variable comp, managing the ups and downs, and treating their patch like a franchise.
- Content and brand matter for founders and sales leaders. Gabe wishes he’d started creating content and building his presence on LinkedIn and via podcasting much earlier; it’s now a key part of his playbook.
Key Moments
- 00:00 – Intro & episode setup. Dan introduces episode 49 and guest Gabe Lullo, CEO of AlleyOop, and frames the discussion around building an outbound engine.
- 01:42 – What is AlleyOop? Gabe explains the basketball-inspired name and how AlleyOop sits between marketing and sales as an outsourced SDR engine booking meetings and demos.
- 03:14 – How it started (ZoomInfo story). AlleyOop began as a sales training company and evolved into SDR as a service after a client (now ZoomInfo) asked if they could just provide SDRs to generate more at-bats.
- 04:51 – “More at-bats” and opportunity cost math. Gabe walks through his three-question back-of-the-napkin calculation showing how much revenue is left on the table when closers are also prospecting.
- 06:07 – How a typical campaign works. Ideal client profile, total addressable market, playbook design, data sourcing, tech stack, and 6-month campaigns with a 90-day benchmark phase.
- 07:05 – Channels, volume, and lead scoring. Why they focus on email, heavy phone activity (150–200 dials/day with tech), and how they score and prioritize leads.
- 08:50 – Adapting to different ICPs and markets. From cybersecurity to HR to recruiters Gabe explains tailoring channel mix and tactics based on where prospects actually live (e.g., LinkedIn-first audiences).
- 10:07 – The “alley-oop” handoff. Warm introductions, reminders, LinkedIn connections, call recordings, and AI transcripts all handed to the AE to maximize show rates and outcomes.
- 12:35 – Founders and role separation. Dan and Gabe talk about the danger of trying to do sales part-time while also running the company, and why focused roles lead to better performance and better days.
- 14:13 – Gabe’s backstory. From executive recruiting to sales training to building dedicated SDR teams and eventually leading AlleyOop.
- 14:58 – Career fork in the road. 9/11 derails Gabe’s original plan to be a stockbroker; he considers law school, then chooses a commission-only recruiting job instead and never looks back.
- 17:05 – Living on variable comp. Why Gabe loves commission-heavy roles, why they’re not for everyone, and how to be self-aware about whether you’re wired for that volatility.
- 19:25 – Sellers as entrepreneurs & “Do Hard Things.” Gabe shares his blue-collar upbringing, the impact of early selling success, and why mental toughness matters as much as physical labor.
- 21:38 – Lightning round: wings, cameras, books. Buffalo chicken wings, why a good webcam is non-negotiable in a remote sales org, and the impact of John Maxwell’s 21 Irrefutable Laws of Leadership.
- 26:27 – Daily prospecting as CEO. Gabe still prospects every day to stay sharp, understand the market, and lead from the front.
- 27:33 – Bucket list & best money spent. Skydiving with his wife, aiming to attend an F1 race, and why good luggage and travel are their favorite sub-$1,000 splurges.
- 28:44 – Advice to his younger self. Start creating content and building a public presence much earlier LinkedIn, podcasts, and getting on shows like this.
- 29:42 – How to connect. Gabe shares that LinkedIn is the best place to follow him and AlleyOop content and invites listeners to DM him.
Episode Summary
In episode 49 of Making Sense of Your Money, host Dan Pascone welcomes Gabe Lullo, CEO of AlleyOop, to discuss what it really takes to build a serious outbound engine one that doesn’t rely on heroic quarters or founders burning themselves out on cold calls.
Gabe starts by explaining the AlleyOop name: in basketball, an alley-oop is the perfect lob that sets up an easy dunk. In go-to-market terms, marketing sets the stage, sales finishes, and SDRs are the lob in the middle turning potential into high-probability scoring opportunities. That’s exactly what AlleyOop does: they design, staff, and run fully branded SDR teams for clients, booking qualified meetings and demos so closers can focus on closing.
The firm actually began as a sales training organization, teaching methodologies like Sandler to full-cycle reps. Everything changed when a client (a small firm at the time, now known as ZoomInfo) said, “We don’t need more training. Our people can sell. We just need more at-bats. Do you have SDRs?” AlleyOop built an SDR team for them, ran it through IPO, and realized they’d found a much more leveraged niche: sales development as a managed service.
Gabe then walks through the math he uses with prospective clients. He asks: (1) How many sellers do you have? (2) What percentage of their time is spent prospecting versus closing? (3) How much did they sell last year? Multiply last year’s revenue by the percentage of time currently spent prospecting, and you get a rough sense of the additional revenue you could drive if you took prospecting off their plates and let them spend 100% of their time presenting and closing.
From there, he explains how AlleyOop designs campaigns: start with the ideal client profile and total addressable market, build a dedicated playbook, source data through providers like ZoomInfo and others, then deploy tech that lets SDRs hit 150–200 dials per day while still being targeted and smart. They run 6-month engagements, use scoring to prioritize leads, and adapt channel mix based on where buyers actually live email + phone in many spaces, LinkedIn-first in others.
The handoff is designed to be a true “alley-oop,” not just a random calendar invite. Prospects receive reminders and warm introductions; AEs receive call recordings, AI transcripts, and all the context they need to walk into the meeting ready to pick up the conversation, not start from scratch. AlleyOop’s North Star is not just “booked meetings,” but qualified meetings that show up.
Dan and Gabe also discuss founder-led sales and the danger of trying to do everything part-time. Founders routinely outsource their website, HR, and recruiting but still try to be both CEO and SDR. Gabe argues that a serious, always-on outbound function is as critical to growth as any of those other outsourced disciplines, and that consistency in prospecting is like consistency in the gym, you can’t expect results if you only go once or twice a month.
On the personal side, Gabe shares his own path. He originally wanted to be a stockbroker, interned in New York City, then had those plans derailed by 9/11 and widespread hiring freezes. He briefly veered toward law school before taking a commission-only recruiting job with a friend’s family firm. Making six figures at 21, he realized he was wired for performance-based comp and never went back to the “safe path.” That experience shaped how he sees salespeople today, as mini-entrepreneurs who must embrace volatility, think like business owners, and do the “hard things” others avoid.
The conversation closes with a lightning round: Buffalo chicken wings (Gabriel’s Gate for locals), investing in a proper webcam for remote sales teams, the impact of John Maxwell’s 21 Irrefutable Laws of Leadership, daily prospecting as a CEO, skydiving with his wife, and why he wishes he’d started creating content and building a LinkedIn presence much earlier in his career.
Full Episode Transcript
Dan Pascone (00:00)
I’m Dan Pascone, CEO of Tailored Wealth and host of the Making Sense of Your Money podcast, Real Conversations to Help High Earners Make Sharper Decisions So Their Money Works as Hard as They Do. This is episode number 49, and today I’m joined by Gabe Lullo, who’s the CEO of AlleyOop, to break down how founders and revenue leaders build a real outbound engine using SDRs to bridge marketing and sales, taking prospecting off of your top closers’ plates.
and creating consistent at-bats so growth doesn’t depend on heroic quarters. Before we dive in, make sure you’re subscribed on your favorite platform. And if you find the show valuable, I’d really appreciate you leaving a quick review. Thanks so much and enjoy.
Dan Pascone (01:05)
All right, Gabe, thanks for joining the Making Sense of Your Money podcast, man. Excited to have you today. Let’s have some fun.
Gabe (01:11)
Let’s do it, man, I’m ready to roll. Dan, I’m a big fan of yours and I appreciate you having me on the show.
Dan Pascone (01:15)
Yeah, yeah, I’m excited to chat because we’ve got a few things in common and some mutual interests, not the least of which is how to develop a revenue engine. So we’re gonna get into that a little bit more. But before we do that, Gabe, tell our listeners a little bit about you, what you and your firm, Alleyoop, which I love, love, love the name of that firm. So we’re gonna talk a little bit more about the genesis of that as well. But tell us a little bit more about what you do and how you got into this.
Gabe (01:42)
Yeah, well, like the name, it’s a basketball term for those who don’t follow basketball. Alley-oop is really that amazing shot, that moment in the game where someone throws the ball up perfectly right next to the basket and then another player comes up, grabs it in midair and slam dunks it. And it’s just that amazing cannon finish moment. And the reality is that we take that analogy and bring it to sales and sales development.
You know, right now, marketing and sales have been always the two departments for running a go to market engine, but there’s that department in between they call sales development or business development. And that’s where we sit. We know our lane, and our lane is to not mess with the other two, but to really help bridge the gap between marketing and sales. And so our team, have hundreds of SDRs making millions of phone calls, outreach every single year.
and our clients come in and we can build them an on-brand STR department for them and run it for them and execute it for them so they don’t have to worry about managing it or running it and we generate introductions, leads, appointments and book demos right on their calendars.
Dan Pascone (02:48)
Very, very cool. All right, so let’s get into that a little bit more. The struggle between sales and marketing is as old this time as you and I know, and most of our listeners know that I have a revenue leadership.
as far as our client base is concerned. So tell us a little bit about, know, when, how, give us the start for Alleyoop. Like how did you guys get started and how did you kind of go at sort of, you know, filling this gap that we know is pretty pronounced.
Gabe (03:14)
Yeah, so 18 years ago when we started, it was a sales training organization. So we would come in and really train and teach whether it was Sandler training or different methodologies on how to actually enhance and enable existing full cycle sales teams. And one of our clients literally asked us, hey, we don’t need actual training. sales teams are killers, They just need more at-bats. They just need more appointments on their calendar. And like, do you have any SDRs? And we’re like, what’s an SDR?
And so we really started off with literally a need in the market from one of our potential clients. And ironically, that client was a small company back then, Infancy, but it’s now ZoomInfo, one of the largest data providers in the world. So when we were asked that, we built out a sales development team for them and ran it successfully until they went IPO. But long story short, that’s really where we started with the concept.
and then have been building SDR functions for many, many, companies. So that was our actual starting point.
Dan Pascone (04:13)
Yeah, it’s interesting because I think if you asked, you know, I sit on two sides of the fences here, being that I had a corporate role and led large sales teams and now being a business owner, I interact with folks in both seats, sort of the revenue executive, revenue leader, and also the smaller business owner. And I think most people would say exactly what you just said, right? I need more at bats, right? If I get more at bats, I’m gonna, you know,
my average will stay the same, right, to keep the sports terms going, then my average will stay the same, but I’m obviously gonna add a lot of top line growth. So like, how do you help firms to get more at bats?
Gabe (04:51)
Yeah, absolutely. And it’s about opportunity costs. we, you you’re a financial guy. So here’s our really quick math on the napkin math that we actually sit down with on every single prospecting call. And we asked them this question. There’s three specific questions. One question number one, how many sellers right now are on your sales floor? And that could be answered literally simply with one and that’s the founder, right? The founder is the only person selling that that that’s the answer. But let’s just say it’s a bigger company, yet a very small company, they only have two salespeople on the sale.
So we have two sellers. Okay, my next question number two is how much of their day is being spent prospecting and how much of their day is being spent presenting and closing deals and usually I’m hearing 60 40 70 30 and and usually the bigger number is actually of them prospecting so they’re self generating doing cold calls reaching out to people and Trying to schedule their days in their weeks and then I look at us. Okay, how much did they sell last year?
All they sell, $5 million. So what I do is I take that percentage of them prospecting, I multiply it by that revenue, and that’s how much money they could have made next year if they took prospecting off their desk and had a firm or us run it for them exclusively. And now your sellers, your people who are taking those at-bats, are spending 100 % of their day presenting and closing deals instead of 30 or 40 % of their day. And that’s really where we come in and what we look for.
How we do that is we have to obviously build them a very structured campaign based on their ideal client profile. We run a playbook and design it for them exclusively. We bring in data so we actually supply them with Zoom info data and other companies we use in the data world. And then we use the right technologies depending on where and how much volume we need to actually make. And then we use technologies and tools to enable our reps. And then we look at, what
reps do we have available to us that are similar in the type of experience that this company is representing? And then we build them that campaign and then execute. And we run campaigns six months at a time. And we usually see a benchmarking happening after those 90 days of prospecting. And then we see predictable results moving forward.
Dan Pascone (07:01)
Got it, so it’s typically like a six month engagement. You’re gonna do everything you just said plus supply the people and then sort of measure what the ROI is from that campaign.
Gabe (07:05)
Correct.
Yes.
Yep, and we’re doing email and we’re doing significant amount of phone calls. Our reps with our tech stack are able to execute 150 to $200 a day on average, which is literally three to four X industry averages. And we use technology to make that happen. And we’re also scoring leads as well on the front end. So we’re not just calling, know, mud against the wall and seeing what sticks. So we’re very intentional about using tools to get intention of why we’re again, we’re prospecting.
who we’re prospecting, when we’re prospecting, how many times we’re prospecting, and that math yields results. And so we’re setting up appointments, qualifying those appointments, and literally embedding it right into their CRM and on their calendar. Or we actually pass over warmer leads. Now these aren’t marketing leads, these are people we’ve actually had conversations with, but the only thing that’s, you know, is not 100 % a hot lead is because of timing. Maybe they just started at their new company and they need a month to settle in.
Maybe they just launched a new initiative or they just hired a group of people and they need a month to settle in. If someone is interested to talk within a 90 day period of time, we pass those over so our clients can nurture them directly. But our North Star is of course is a hot meeting booked on the calendar and that’s what we deliver.
Dan Pascone (08:24)
Yeah, and I know you told me before we went on live that you’re able to, or being that you’ve been in this for 18 years, you’ve been able to develop these systems and processes for a pretty wide range of companies, verticals, sizes, et cetera. Tell us a little bit about that experience. I’m curious how your approach may differ from working with a Zoom Info to maybe a small company that all of the sales is being developed by the founder.
Gabe (08:50)
Right. So we’ve worked with 1600 different brands over the last 18 years across every vertical industry and in market and size you can think of. Now we don’t do B2C, know, we are not, you know, reaching out to people on Instagram. We’re in the B2B space. But if there is an appointment or a demo or a discovery call that sits within your sales journey, very much we can book a, probably book a, a build a, excuse me, a program or campaign around it just based on our
previous experiences. So yeah, I mean, we look at first off the ideal client profile and the total addressable market and we’ve worked backwards from there. You if you have a huge total addressable market, you know, maybe a higher volume play with a parallel or a power dialer makes the most amount of sense, but it may not even be the phone. I mean, maybe your prospect don’t pick up the phone. Maybe there are a set, you’re selling a cybersecurity and it’s an impossibility. So what do we do differently there?
Maybe you’re calling HR people or recruiters and they’re living on LinkedIn. Well, maybe should do a LinkedIn outbound campaign and we can live there. Now, we do believe in multi-channel, multi-threading and doing every single thing we can to at least get someone’s attention, but we definitely want to triple down on things that your audience is just living on. So that’s what we focus on.
Dan Pascone (10:07)
You started to touch on what was gonna be my next question, which is kind of like the ollie then the oop. So I imagine that the handoff from your team and your campaign over to your client is typically just a book demo call or is there typically some sort of like warm introduction handoff in between?
Gabe (10:26)
Yeah, so we’d like to make it as warm as humanly possible. So it’s not just one we put on the calendar and hope and pray it shows up. You know, just because we put meetings on the calendar, that’s not what we get excited about. We get obviously excited just as our clients get excited about meetings that actually show up that actually have interest. So what we want to do is we want to actually hold us responsible to everything up to the meeting. So we do that through reminders. We do that through connecting on LinkedIn. We do that through a warm introduction email.
to the salesperson who is at our client and the prospect themselves. We’re also enabling our clients in a big way. So we’re sending them a push notification of all the details they need to know about that prospect, including the recording of the call that we had with them and an AI transcript of those notes as well. So on the client side, they’re going into that demo with literally every single thing they need, including the conversation we had with them.
to go into that call is prepared as humanly possible.
Dan Pascone (11:26)
Yeah, I love it. You also touched on a point that is, firmly and passionately believe, and frankly I’ve built my whole business structure around, which is sort of this bifurcation of sales and service. I think that’s been done for a long time, especially in the tech space. But you mentioned allowing the founder or the CEO to get out of the sales lane and allow that to be done.
really intentionally, really on a full-time basis. And what I love about that, and I’m curious to hear your perspective is, I believe that when there’s a function that’s as important as sales, and I’ll call it sales and marketing together, having somebody try to do that part-time and then have all these other priorities, it really, really gets watered down. And frankly, I tried to do it at some point in time in my career and I.
I didn’t really love what my day-to-day looked like, so I’m a big believer in separating roles, being really, really targeted in the function that you’re performing, and allowing you to have kind of focus and clarity around your day. How have you seen that sort of translate, especially with like founder-led sales teams?
Gabe (12:35)
Well, they’re outsourcing typically outsourcing everything else when you start a company, right? You know, going to professionals like you for financial, you know, needs, are they building the market? Are they actually is the founder building the website? Are they probably probably not right? So it’s like they’re using a marketing firm to build the website. They’re not building the website part time, right?
So, you know, they’re not using, they’re probably using an HR, outsourced HR function to support the handful of employees that they currently have. They don’t actually have a head of HR when they have three employees. So they’re already outsourcing all the other parts of their business. You know, usually maybe do a staffing firm to source new hires as well. So having a turned on function that is completely customized and white labeled for prospecting.
I believe should be treated no different than hiring a company to build your website. And so just having that done right and turned on all the time is what’s the most important. Because everyone will say in sales, the number one thing in sales is consistency. And just like working out, can’t get in shape if you work out part time once or twice a month. Similarly here, you need to be prospecting every minute of every single day if you want to do it right.
Dan Pascone (13:37)
Yeah.
Gabe (13:49)
And it’s very difficult to do that when you’re juggling five other things running the company. So that’s why I think you should just look at it from that lens and that perspective, like you do the all the other parts of your business when you’re starting up.
Dan Pascone (14:01)
Yeah, we could, there’s so many good analogies between sales and exercising. I mean, that’s a pretty pronounced one. I’m with you on that one. All right, so let’s learn a little bit more about you, Gabe. How did you get into this? Tell me a little bit about your backstory.
Gabe (14:13)
Yeah, I started off in recruiting. So always been in the people business. So I started off in executive search and executive staffing and, you know, find my way really loving recruiting for revenue positions and heads of sales and heads of marketing. And then I got into that sales training function where I was actually training salespeople on how to sell. And then once we know we realized that there was a need in the market for sales development.
That’s where we actually doubled down on the SDR world with Alieu. So that was essentially my journey to the company.
Dan Pascone (14:46)
Very, very cool, very, very cool. Tell me a little bit about like, is there one decision you made? Is there like a pivotal point within your career that sort of shaped and brought you to where you’re at today, leading Ali?
Gabe (14:58)
Yeah, I mean, I was in school and I, you know, I thought I wanted to be go, go out and you’ll be a stock broker. You know, I, you know, I watched all boiler room and I’m like, I gotta go and you know, you know, sell stocks. And so I was doing internships in New York city and realizing, you know, this is something I wanted to do. And then all of sudden nine 11 happened and there was job freezes across the board. All of the places that I interned for work hiring because of everything that was happening. And so I just kind of like,
Dan Pascone (15:07)
Yeah.
Gabe (15:27)
thought what do I do next? And I actually took the LSATs, got into law school and I was gonna go to law school. Now I had zero interest in wanting to do that but I just felt like that’s what I needed to do because there was no other opportunities. And I was always told, hey Gabe, you know how to talk, you should be a good lawyer. The people who are in sales, I know a lot of people in sales, every person I in sales have been told they should be a lawyer in somewhat part of their life, usually early on, right? So I was that guy. And then I said, you know what?
Dan Pascone (15:42)
Yeah, sure. I got that as well growing up. I got a lot of that.
Gabe (15:55)
don’t know if I really want to do this. And then I was presented with an opportunity to work for my good friend’s dad’s recruiting business. And I said, you know, I’m going to defer for one year and, and go, you know, hard on this. And I made six figures, you know, as a 21 year old in that space, and I never looked back. So that was a massive decision point. I kind of like that fork in the road is like, go out, do I go out and be a lawyer and go down that road?
or do I do everything my parents, my friends, and all of my associates tell me I shouldn’t do and get a sales job? And so I did that and I’m really happy I did.
Dan Pascone (16:33)
Good for you, good for you. Tell us a little bit about your financial journey along the way, right? you know, sales professionals is interesting because, you know, we do a lot of work with sales professionals and it’s interesting because you’ve got this dynamic of like, eat what you kill, variable pay, know, lack of consistency, great upside, but a lot of downside. So how is that?
come through in your financial journey having been in some way, form in a sales role for the majority of
Gabe (17:05)
Yeah, mean, well, financially, you know, I’ve always had an incentive, a commission, a bonus, you know, a carrot, if you will, in front of me. And I think that is extremely motivating for me. If you talk, if you present that to my wife or my cousin or my sister, that is the opposite of motivation. Right. So I know for a fact that, you know, people just can’t, you know, be in a position where, you know, they’re paid based on performance.
Dan Pascone (17:26)
You
Gabe (17:32)
I mean, for six years of my life, seven years of my life, I was commission only. And that was by choice because I made more in commission only comp plan than I did on a hybrid comp plan. And so that to me always excites me and it motivates me. So from a financial perspective, that keeps me going. And I’ve never not gotten some sort of commission in my life. And I’ve been doing this for 25 years.
But at the end of the day, I think it’s super important to be self-aware of that because it is not for everybody. And there’s a huge turnover in sales, more so than working in the restaurant business. And if you think about it, right, so you have to be wired for it and be ready for making those types of financial commitments. Because to your point, one month you’re eating lobster and the other month you’re eating ramen noodles.
So that’s way too up and down for people. And so you have to be consistent and be financially aware of that.
Dan Pascone (18:27)
I love that. mean, I think that that like, and it’s not an easy process to go through. Sometimes you just have to get it with experience, but identifying if you’re made for variable compensation, performance-based pay. The earlier you can identify that in your career, frankly, I think the better off you will be. And that helps to probably frame a lot of decisions. I’ve seen folks, it take them a long time to figure that out, frankly.
But I think whether you’re a sales professional or even a business owner, you’re gonna have some level of risk that you have to deal with. How have you seen the best professionals that you’ve been around? Because I’m sure you’ve been around some great sellers and some great business owners. How have you seen the best people that you’ve been around kind of manage that and use it as a motivation, but not have it be something that like,
has a negative impact on their performance, but also their life and their relationships. Because I’ve seen that.
Gabe (19:25)
Yeah, for sure. mean, it’s like you look at analogies when you look at the boxer, right? You know, if you’re getting backed into the corner, do you fold and say, you know, uncle, or do you come out swinging and you have to have that back in the corner type mentality? many, many times when you’re either building a business or running a sales career. And if you think about it, you know, I treat my sellers who work for us, they have a salary, they have a commission, but I enable them and talk to them as if they are building their company within my company.
Dan Pascone (19:53)
Right.
Gabe (19:53)
And if you’re not operating as a seller, like an entrepreneur, as a business owner, or, you know, think about it like a franchise, if you will, at your job, then you’re going to have the tough times completely take you out. I mean, I love podcasting. We have our own podcast. called do hard things. And the reality is, is it’s, it’s born on this story. I grew up in a blue collar town of Buffalo, New York. You know it well. And most people in my family and in my upbringing were always
having to do something physical to make money. They actually had to lift heavy things, they had to go snow plow, they had to go on the roof and they had to fall off the roof and get hurt on the job. They were sweating, they were smelling like fish at the end of the restaurant shift. That was the family that I grew up in. And then I, at 11, realized I was doing a fundraiser for my school and I was selling T-shirts to save our local Niagara Falls aquarium. And it was funny, I actually…
Dan Pascone (20:44)
Okay?
Gabe (20:47)
sold more t-shirts than any student out of all the schools regionally. And I’m like, my God, I have to talk and make money? This is like mind bending information. How cool is this? I don’t have to lift heavy things. I don’t have to get hurt on the job. This is great. But then when I realized that it’s just as hard and it’s not hard talking to people, and yet it is hard for some, but you can figure that out. The hard part is what you just said is going through the dumps.
Dan Pascone (20:56)
How cool is this?
Bye.
Gabe (21:14)
is going through the inconsistencies, it’s going through the challenges, and it’s doing the hard things, even though it’s not physically challenging. And that’s where I think people have to really get their mindset checked. Who are you listening to? Who are you following? What books are you reading? What podcasts are you listening to? You kind of have to get obsessed with just getting better every single day at this, or you’ll be left behind, especially in the world of AI.
Dan Pascone (21:38)
I love it, I love it. That’s a great place to pause and we’re gonna transition now into the lightning round, Gabe. So I never give our audience much of a heads up on the lightning round, because we just want it to be super organic. So here’s the deal. First thought that comes to your mind could be a long drawn out thought, could be a story, could be one word answer, whatever comes to your mind. You ready? All right, let’s do it. We’ll start with an easy one. I think it’s an easy one. One meal for the rest of your life, what would it be?
Gabe (21:57)
Yeah, ready.
Well, I’m from Buffalo, so has to be chicken wings.
Dan Pascone (22:05)
All right, so I happen to know Buffalo well. I used to have an office there. What is your wing spot in Buffalo? Because there’s always been a lot of debate around that. What’s your spot?
Gabe (22:14)
There is a big debate and I’m asked this a lot and we actually have a family that has gone to pretty much everyone and we grade it and we rate it. So we’re very fanatical about this. I like Gabriel’s gate and no, don’t. I’m not affiliated even though it’s the same name as mine. It’s Gabriel’s gate on Allen street in downtown Buffalo. Very, very good wings, but also there’s of course Duff’s, is pretty big. Yep. Anchor bar, which is where they started it. Yeah. And then, you know, you can look at so many now, but the
Dan Pascone (22:21)
Okay.
Yes.
Duff’s is popular.
started it.
Gabe (22:43)
The underground, the place, if you come here and you talk to the locals, they’ll probably throw Gabriel’s gate at you for some.
Dan Pascone (22:49)
Yep, I’ve had Gabriel’s Gate, very, very good. I think I’ve had each of those three that you’ve mentioned. awesome, I love it, really good stuff. Yeah, I love it, I love it. All right, this’ll be an interesting one for you, because I know that you surround your clients with technology and tools to help them to have the alley-oop, so to speak. What’s one tool or technology other than your computer or your phone
Dan Pascone (23:16)
that you can’t live without.
Gabe (23:17)
My camera. And the reality is is that I buy a 1080p camera for every single employee at my company the day they start. And I don’t rely on their MacBook camera because I don’t want the nostril view. I don’t know if you know what I’m talking about, right? You’re looking at your laptop and you get this visual nostril view coming at you. The reality is is we are a fully remote company with hundreds of employees and salespeople are people people.
Dan Pascone (23:24)
Interesting.
Yes, thank you.
Gabe (23:41)
and you need to see the other person. Now, I’m not talking about just for prospects and conversations like you and I are having, which are super important to have a good camera, but just internal conversations with your managers and colleagues, it is so important. Every one of our sales reps live on a video sales floor, and they’re literally seeing the other people next to them. Similar to what you would expect in office in a cubicle type setting or an open floor concept, but virtually, and it’s so important to really understand what people are thinking.
how they’re communicating, body language is so important. So camera technology for us is really first when it comes to our ability to communicate.
Dan Pascone (24:17)
And do you have a recommendation there for those that are looking to improve there? I don’t necessarily need you to plug any specific brands, but like, are you just getting like a webcam instead of just using their typical laptop camera? What are your thoughts for sellers out there as to how they can show up literally the best way possible on these virtual calls?
Gabe (24:38)
I have a $2,000 Canon, know, Canon, excuse me, you know, real camera. Now that’s my webcam and it’s, you know, I graduated to that because I’m doing podcasts, I’m doing videos, but I want to stand out when it comes to camera. You can look at things that are just at $200, like Logitech cameras are really good. They’re, they’re out there. I don’t, I would not recommend spending more than a hundred to $200 on a camera unless you’re going into the podcasting world, but that
positioning of it, so you’re making eye contact, the lighting that you’re having so you actually look good on camera. Those are things to think about when doing sales demos and video calls each and every single day. I’m telling you it sounds kind of like, you know, just nuance, but it’s so important when making a first impression.
Dan Pascone (25:28)
I love it. Great advice. I completely agree with that one. You mentioned books earlier. Is there a book that influenced how you think or lead?
Gabe (25:37)
Yeah, I mean, my original book is called The 21 Irrefutable Laws of Leadership by John Maxwell. That’s one of the first books that I read. Anything from him, he’s written 20, or sorry, 80 books. I’ve seen him live at seminars and conferences. You know, one of the things in there is there’s different laws, right?
Dan Pascone (25:44)
Yeah.
Gabe (25:55)
The one is the law of association. So if you look at the sum total, and you could talk economically, of the five people you associate with and hang out with, and if you statistically look at their incomes and you do the average of that, it’s right around probably what you’re making, right? So that law of averages is so important. There’s so many other laws that are in there that are super, super important that taught me the basics and fundamentals of leadership.
Dan Pascone (26:21)
Love it, love it. What’s one habit that you would say has had a major impact on your success?
Gabe (26:27)
I prospect every day. I’m the CEO of a prospecting company. So that sounds like I should be doing it, but there is really no need for me to be doing that every day. I have a lot of people doing that for me and with us. So, but I still do it because it keeps me sharp, right? When someone who’s brand new decides, Hey, to jump in my Slack channel and asks me for help or advice.
Dan Pascone (26:29)
Okay.
Gabe (26:50)
I can give him that advice or her that advice that is actually relevant. It also helps you. Yeah. It helps you understand what the market is doing. It helps you understand what your competitors are doing. Helps you understand, you know, just, just being aware of what’s going on in the market because that’s our product. Um, but of course it also brings us business too, which is of course is fun, but being the first person prospecting, especially if you’re a founder, uh, even though, like I said before, you don’t want to be doing it all day. Like,
You are probably now hire us to do it, but you still want to be in those conversations and in those relevant meetings, even if it’s just a few times a week.
Dan Pascone (27:26)
Love it. Can you share a bucket list item, one that you’ve already accomplished and maybe one that you’re working towards?
Gabe (27:33)
Hmm. This is a good one. Well, I jumped out of an airplane, and I, I convinced my, I convinced my wife who I would tell you if I had all the money in the world and I bet I would have never convinced her to come with me, but I did. And she thought it was the greatest thing in the world. And so we did jump out of an airplane. and that was super fun and we’re big F1 fans. So we’re, our next thing is to actually, go to an F1 race. That’s our goal to do it this year. So we’re excited to.
Dan Pascone (27:37)
Okay, all right, that’s good. Check that.
Gabe (28:03)
to do that and excited to see more attraction on that sport.
Dan Pascone (28:07)
I love it, I love it. Best money under $1,000, so the best purchase under $1,000 you’ve ever spent.
Gabe (28:14)
my gosh.
We like to travel. I mean, I love buying luggage. We bought some really nice luggage and it just changed our way. And we actually like to travel more because it just, it just feels good. So traveling to us is great. We were in three different cities the last three weekends alone. Working remotely allows us to do that. And so just being excited to see the world, I think that that allows us to do that for sure.
Dan Pascone (28:24)
Sure. Yeah.
Love it, love it, good stuff. All right, last one. Advice you would give your younger self, what would it be?
Gabe (28:44)
It’s a great one. would say the biggest thing is to just put yourself out there more. And I know that’s kind of weird because in sales, that’s literally what the whole game is. But I slept on content creation for a long time. know, four years ago, I started posting on LinkedIn and I literally had 2000 followers.
Dan Pascone (28:56)
Yeah.
Gabe (29:03)
You know, now I have, you know, a lot more, but I will say I would have done that a lot earlier. So put yourself out there, create content right from the, you know, from the horse’s mouth, I think is the most important thing you could be doing. You know, I could be doing a lot of other things right now, but I’m here with you because I think this is super valuable to get not only, you know, yourself out there, but to network and to meet people and to, and to be aware. So.
I should have started a podcast a long time ago. I should have posted on LinkedIn a long time ago. That’s what I would have told myself in my earlier days.
Dan Pascone (29:36)
I second those, I, know, better late than never for sure, but I second both of those. All right, and then finally, if our listeners want to connect with you, collaborate, learn more about Alley-U, what’s the best way to follow you, connect with you, learn more about your.
Gabe (29:42)
Yeah, for sure.
Yeah, LinkedIn. I post twice a day myself every day. We have a ton of content also being reshared from my profile, from my team who’s posting. And so there’s a lot of great free advice and content there. I tell people, if you can watch all my videos, you can do what we do. Or you can save yourself a lot of time and we can do it for you. But either way, we’re very active. And you can just DM me or send me a connection request with a note.
There’s a lot pending, so just send me a note. Let me know you saw us on the show and we’ll send a connection back and have a conversation.
Dan Pascone (30:21)
I love it, I love it. Great stuff. Gabe, thanks for coming on. Really enjoyed the conversation. Appreciate your insights. Thanks for joining us today. That’s it for the episode. You can find our podcast along with our newsletter and YouTube channel all free at makingsenseofyourmoney.com. And as always, prioritize your version of a rich life.
Resources & Links
- MakingSenseOfYourMoney.com – podcast, newsletter & free resources
- Tailored Wealth – official site
- AlleyOop – SDR-as-a-service & outbound engine
- Gabe on LinkedIn – @gabelullo
Frequently Asked Questions
What does AlleyOop actually do for clients?
AlleyOop designs, staffs, and operates fully branded SDR (sales development) teams for B2B companies. They handle ICP/TAM targeting, data, outreach (phone, email, LinkedIn), lead scoring, and booking qualified meetings and demos directly onto the client’s sales calendar acting as the bridge between marketing and sales.
How is this different from hiring one or two in-house SDRs?
Instead of building and managing an SDR team yourself (recruiting, onboarding, tech stack, training, management, and constant optimization), AlleyOop provides a turnkey, battle-tested outbound engine. Their SDRs typically achieve much higher activity levels thanks to specialized tooling and process, and clients benefit from 18+ years of cross-industry experience.
Why shouldn’t my top sellers keep prospecting for themselves?
It’s an opportunity cost problem. If a rep is spending 60–70% of their time prospecting, only 30–40% is left for presenting and closing. Freeing them from prospecting lets them spend nearly all their time in high-value conversations, which can materially increase revenue without adding more headcount.
How does AlleyOop warm up handoffs so meetings actually show?
They don’t just drop a meeting on the calendar. Prospects receive reminders and warm introduction emails, SDRs often connect on LinkedIn, and the receiving AE gets notes, call recordings, and AI-generated transcripts so they can step into the conversation fully briefed. The goal is high show rates and quality, not just volume.
Is outbound still worth it in a world of AI and digital noise?
Gabe’s view is yes with the right focus and consistency. Intelligent targeting, multi-channel outreach, and a dedicated SDR engine that runs every day can cut through the noise. AI and tools help SDRs work more efficiently, but they don’t replace the need for human, relevant, well-timed conversations.