In one line
Greg Crisci, the top Senior Enterprise Account Executive at Upwards (a childcare-benefits technology company), became the startup's #1 seller by treating novelty, deep industry obsession, and a design-honed pitch as his edge — a career he traces back to a lifelong "addiction to excitement" he had to confront through sobriety and therapy.
Who is Greg Crisci?
Greg Crisci is the top Senior Enterprise Account Executive at Upwards, a technology-driven care-solutions company (originally called WeCare) that matches families with caregivers and helps employers offer childcare benefits. Based in San Diego, Greg has been entrepreneurial since 4th grade — selling stapled booklets, then Pokémon and baseball cards, then candy through a small high-school sales crew — and founded his first company, Tip Network, in 2010 while waiting tables at Chili's and working at a fast-growing digital marketing agency. He joined Upwards in 2020 (starting for free during the pandemic), helped build its enterprise sales motion from scratch alongside the CEO, and closed benefit programs at large hourly-workforce employers including Amazon, John Deere, and Albertsons. Greg is candid about the flip side of a sales personality wired for the highs and lows: a gambling and alcohol addiction he now manages through a 12-step GA program, ongoing therapy, and a sober life.
Key questions answered
How did Greg Crisci become the #1 enterprise seller at his startup? Per Greg Crisci (Upwards), on Sales Success Stories, three things set him apart: an instinct to challenge the status quo and be novel ("you can't teach it"), falling in love with and going deep on his industry (childcare benefits — reading 10-Ks and investor theses, even running his own niche podcast), and content curation, organization, and a design mindset honed on an ad agency's pitch team building novel decks for clients like Best Buy and Hasbro. 0:01:29
What does Greg Crisci sell at Upwards and how did he get to #1? Per Greg Crisci (Upwards), the company was a B2C childcare marketplace that pivoted to enterprise when the city of Los Angeles asked for daycare access for first responders during 2020, generating press and inbound B2B demand. He started for free, was brought on as employee ~20–30, built the enterprise program with the CEO, and out-hustled the field — handling a pipeline "that probably 2 or 3 people needed to handle" — until deals started coming to him. He now sells strictly to enterprises above 10,000–25,000 employees on a team of about 5 AEs. 0:09:49
What is Greg Crisci's sales origin story? Per Greg Crisci (Upwards), the through-line from 4th-grade booklets to Pokémon cards to blackjack to hospitality tips to entrepreneurship was always the same — chasing the dopamine of "you never know what you're gonna get," each step riskier than the last. That wiring made sales, especially enterprise sales, a natural fit, but it also became a gambling addiction he later recognized as an "addiction to excitement." 0:14:10
How does Greg Crisci stay in sales while managing an addiction to excitement? Per Greg Crisci (Upwards), he leans on a 12-step GA (Gamblers Anonymous) program, goes to meetings twice a week, and keeps two therapists — one he's seen since 2010 and one specific to gambling. Reading Ego Is the Enemy helped him see how much of his drive was ego, and he reframed sales around impact over money: "it's the impact that I had versus the money that I got." 0:19:13
How does Greg Crisci deal with sales burnout? Per Greg Crisci (Upwards), he burned out three times — his most recent as recently as last year — and got through each by being a vocal advocate for therapy (cognitive behavioral therapy done consistently), leaning on a close support system, and being driven by something bigger than money: proving himself and creating impact. His advice to anyone at the wall is to reach out, talk it through, journal it, and do hard self-reflection about priorities. 0:26:46
What does Greg Crisci believe that most salespeople would think is crazy? Per Greg Crisci (Upwards), that long monologues are okay. He acknowledges Gong data linking shorter monologues to higher win rates, but argues a subset of sellers close more with them — if you can deliver a monologue like a "mini TED Talk," slowing your pace so the listener is on the edge of their seat saying "keep going," you can make people feel your passion through the screen. 0:49:24
What is Greg Crisci's actionable challenge for salespeople? Per Greg Crisci (Upwards), practice "catch it, check it, change it": when something triggers you emotionally — an ad, a thought, a conversation — stop, examine why, and use that self-knowledge to influence others in your pitch. Pair it with an "aha" habit: when a business model fascinates you, dig into how the founder connected the dots and write it down — a bank of examples that trains you to find root causes, which is exactly what enterprise sellers do. 1:14:03
Frameworks & concepts
- Catch it, check it, change it — a self-awareness habit: catch an emotional trigger, check why it happened, then change your response or apply the insight to how you pitch.
- Go deep to become novel — you can't decide to "be novel"; obsessively going deep on an industry or idea makes you novel automatically, because the fascination shows up in your voice and questions.
- The "aha moment" habit — when a startup or business model fascinates you, research how the founder connected the dots and write it down; the goal is a personal bank of root-cause insights you can cross-apply to other industries.
- Cross-pollination — taking a concept proven in one industry (e.g. multi-sided marketplace / ecosystem "network effects") and applying it to another; Greg used it to help push Upwards from a two-party model toward a government-employer-family-caregiver ecosystem.
- Addiction to excitement — Greg's reframing of his gambling/alcohol addiction: the core craving was the ups and downs and the VIP "big shot" feeling, not the money — the same wiring that draws people to sales.
- Working with your chronotype (the "When" principle) — from Daniel Pink's When: it matters not just what work you do but when; Greg reserves his most strategic, thoughtful work for his peak window of roughly 6–7 a.m. to 2 p.m. and books demos/meetings for the afternoon.
- Overusage leads to underperformance — a point Greg and Scott build together: when an aggregated tactic (a cuss-word stat, "email Tuesday at 2") gets widely adopted, it stops working, so the contrarian move often outperforms the data.
- Inventor vs. executioner — Scott's frame that Greg affirms: some sellers thrive being handed a system to run better than anyone, others thrive inventing the whole sales motion at a startup; knowing which you are should guide your career and company-size choices.
Notable claims
- Per Greg Crisci, only about 7% of companies currently offer a childcare benefit while 48% are looking to add or expand one.
- He out-produced the field at Upwards by handling a pipeline "that probably 2 or 3 people needed to handle," which established him as the top seller.
- Upwards sold childcare-benefit programs to large hourly-workforce employers including Amazon, John Deere, and Albertsons.
- He now sells strictly to enterprises of roughly 10,000–25,000+ employees on a team that has stayed around 5 AEs.
- Greg has burned out three times over his career — the most recent as recently as "last year" — and manages his recovery via a 12-step GA program (meetings twice a week) plus two therapists.
- He was diagnosed with adult ADHD, which he says helps explain both his spatial thinking and why the trait is common among salespeople.
- He cites Gong data that win rates rise with fewer/shorter monologues — then argues a real population of sellers closes at higher rates with longer ones.
Companies, tools & books mentioned
Companies & organizations: Upwards (formerly WeCare), Tip Network (Greg's 2010 startup), Chili's, Amazon, John Deere, Albertsons, Best Buy, Hasbro, Fry's Electronics, Product Hunt, Dwolla, Costco, Gamblers Anonymous (GA), Alcoholics Anonymous (AA).
Tools: Evernote, Google Alerts, Google News, LinkedIn, Gong (referenced as a data source), HubSpot (referenced re: cold-email tactics).
Podcasts: The Michael Singer Podcast.
Books: The Unsold Mindset (Colin Coggins), Ego Is the Enemy (Ryan Holiday), When (Daniel Pink), The Untethered Soul (Michael Singer).
Connect with Greg Crisci: LinkedIn.
Quotes
"Sales is some form of a gamble. You have the lows, you have the highs. And they can be really low and they can be really high. But as you see from my origin story, that is just how I was wired." — Greg Crisci 0:14:10
"It wasn't just an addiction to gambling or addiction to alcohol. It was an addiction to excitement. And that's the core of it." — Greg Crisci 0:19:13
"I'm the one that's going to like connect the dots that nobody saw." — Greg Crisci 0:55:43
"There's a saying, they say catch it, check it, change it. So you catch it, you think about it, you check it." — Greg Crisci 1:14:03
"If you are starting out now, keep front and center your mental health. And that means having some support system, having some awareness that things are going to go up, things are going to go down." — Greg Crisci 1:05:22
0:00 Scott Ingram: This episode is brought to you thanks to the generous support of The Sales Collective. They've got a little something for everybody. If you're leading an organization, The Sales Collective can help you introduce real sales process or improve your own process so that you can consistently generate revenue and help your sales team deliver more. If you're an individual contributor, they have a ton of resources, including their Sales DNA test that will help you identify your own areas of improvement along with 250 videos to help fill those gaps. Check them out at thesalescollective.com or top1.fm/tsc.
0:46 Scott Ingram: You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help you improve. To learn more, visit us at top1.fm. Here's your host, Scott Ingram.
1:02 Scott Ingram: Today on the Sales Success Stories podcast, my guest is Greg Crisci. Greg is the top senior enterprise account executive at Upwards in San Diego. Welcome to the show, Greg.
1:11 Greg Crisci: Hey, thank you for having me.
1:13 Scott Ingram: Yeah, this is going to be fun. I'm looking forward to digging into this. But before we get into all of the context around you and Upwards, let's kick things off with some immediate value like we always do. Let's talk about the top 3 things that you believe have contributed the most to your success in sales.
1:29 Greg Crisci: Yes. So I did spend some time with this. There were probably more than 3, but when we first got on this call, right, we were talking about presentation styles and the novelty about it. Something about me, and as we talked, I've been an entrepreneur pretty much my whole life from back when I remember of being in 4th grade, like I would staple a bunch of pieces of paper together. And I'd sell them for a quarter. There's a whole history of those little things adding on to each other to kind of get to where I was. But the commonality was just being different. It was being novel. The first thing that I thought about in the things that maybe has made me successful is I've tended to go against the grain. But when I hear like traditional things or when I hear things that like, this is always how it's done, It just physically makes me go the other way. I've been like that my whole life, and that I think has been one of the reasons why when I talk to people and when I work with people, that they just see something a little different. And it comes down to like, you can't teach it. And there's a book by Colin Coggins where he talks about authenticity and like, it's a big buzzword, but you can't teach it. And the novelty is not just some of the ideas, it's the way that you show up. Like I showed you before this, when I pitched John Deere, I showed up superimposed on a John Deere tractor. Like those little things were very, very novel. I think the novelty, it's hard to teach. You know it when you see it and you ultimately have to look inside yourself and then have that barrier that you just break down and you really just don't care what people think and you're just being you. Many people at my work would say the Greg-isms are like, that's just Greg. You are who you are. It's hard to teach. But again, novelty, I think, has been interesting. The other thing that I think has been successful for me has been falling in love and being fascinated with the industry. And I'll give 2 examples. My first company that I started, which was in 2010, it was called Tip Network, and it came out of me being a waiter at Chili's. And this is coming off of like, I was going to school as well. I was part of the entrepreneur program. I was reading like Malcolm Gladwell books in my like spare time. And I think there was a… I forget who it was… there was a quote, if not me, who? If not now, when? And I was like, I have to do this idea. Which the idea was, why can't I just leave my tip money here at the restaurant and then it makes its way to my bank account? And given 2010, there wasn't a lot of ways to move money. For those people that are in fintech, it was like Dwolla, or you had to like tap into the ACH network. Like, it was not easy. They did not have direct-to-debit. There was some closed-loop payment networks back then. But as I go on this tangent, it comes back to falling in love and being fascinated with the industry. So I got into this niche of tipping in restaurants, and I just went deep on it. Anytime I went out, I would talk to a manager. Anytime I would go out to a restaurant, I would talk to the waiter. My current industry is with childcare, and I have gone deep in the industry, so much so that I've also forced myself to do a podcast where I talk specifically about childcare tax credits for employers across the US, like very specific niches that both were fascinating to me. I think I know why I like them. But I think the going deeper than just I'm going to read like a 10-K, I'm reading like investor thesis about the space. So the care space is pretty new. Any event that I can get my hands on, talking to anybody that I can, but looking more for the trends in the industry and showing up and being able to have these conversations with people that a lot of people in my space, they aren't sure what a childcare benefit is. 7% of companies have one and 48% are looking to add or expand. And so I'm able, because I've just… instead of going out, I read about the industry that just comes across, just comes across when I'm talking to people. And I think that makes people feel comfortable that like, I got you, I know what I'm talking about. And I think that's probably the second is the falling in love and being fascinated with the industry. And the third would be content curation, organization, and a design mindset. And I believe in one of your prior guests, that was one of the things that they had talked about. I think it was more content curation and organization. I think I threw in design mindset, but this ties back to number one, which is creating novelty. In 2010, I started working at a digital marketing agency. I was always fascinated with technology and like online, and I was the one that was like building a computer from Fry's. I don't know if anybody remembers Fry's Electronics, but yeah, remember? And they had the cool like aquariums, but I dabbled into that. And in college, I got introduced to one of the owners of this digital agency, had done a presentation. And the presentation just blew me away because I never saw anything like it. The quality of the presentation, the imagery, the typography, the way he was speaking about it… I was fascinated. I was like, I need to go work there. And luckily, one of my professors knew the CEO, so I got an interview. I went through the interview process, and this was an up-and-coming agency. I think they had like 60, 70 employees at the time, and then within like a year, it went up to like 400 or Something around that. What I realized was I actually really didn't know about digital marketing. I think I faked it till I made it. I knew a little bit. I knew more than the other people interviewing. Let's just say that. But having that experience at a digital marketing agency, when I first got on, they said working at an agency one year is like working 5 years in the corporate world. And that's so true just because of how fast-paced the quality of thought that is there, like the density of knowledge and intelligence. It is everywhere. Everywhere you turn, there's somebody like… I definitely was not the smartest person there, but I was an entrepreneur. I had an ego. I thought I was, but I definitely got put in my place many times. But that comes back to how I think I've been able to be successful is I started obsessing a little bit with user experience and design. I'm not a designer, but I know what it looks like because I worked on the pitch team. The pitch team, we would have clients like Best Buy and Hasbro, like all these companies that are like, here's the next campaign, come up with something that is different. And I just got exposed to that for about 2 and a half years on the pitch team. I got to see what does novel pitches look like that you have to just put together really, really fast. And it has to be of agency quality. And doing that over and over and over, that helped with the novelty, but it also helped with the design mindset that ties back with curation and organization. I think I've been able to pull things together that not many people have been able to pull together, organize things in a way that people are like, that's interesting of how you layered that information. And then how do you make it look good? How do you actually make it look a little bit different? So those, I think, are the 3 things after I'd asked that question. Those were the 3 that came to mind.
9:20 Scott Ingram: Super interesting.
9:21 Greg Crisci: Any spark your interest? Well, any of them relatable?
9:24 Scott Ingram: Super interesting. So what I want to do is come back to a couple of those things rather than commenting on them now, because I want to understand a little bit more about how some of the dots connect in what you're doing now and some of your history and things like this. And then we'll come back to it. So why don't we first provide the context just around a little bit more depth on your current role, how you got to be the top performer in that role today.
9:49 Greg Crisci: Yeah. Okay. So Upwards is about 7 years old. One of the founders is actually an entrepreneur friend of mine. I've known him since I started my company. How I got into Upwards was 2020, right before the pandemic. I had launched a startup. And it was in the trade show space. So not the year to launch a trade show startup, by the way. 2020 was not the year to do that. Everybody was saying, oh, it's gonna go like trade shows will be back. I gave it a couple quarters. At that same time, I saw on Product Hunt that my friend who started Upwards, which we were originally called WeCare, by the way, Upwards was originally called WeCare. They had started this program that allowed people to take their temperature via their phone of their kid. It was really more machine learning, would read what's on the temperature and give that person like a pass, like you don't have a fever, you can come to school today. So I saw that on Product Hunt and I reached out to my friend and I was like, this is amazing. Can I do anything? They had raised some money, but obviously in the pandemic, money was tight. So I ended up connecting with the person that was leading sales. And I just said, let me work for free. I had a little bit of funds in the background. I didn't really have a job because I had that startup. Let me work for free. So I ended up doing that for about 3 months, and then at that point I got brought on as an employee. So I was probably employee maybe 30, maybe 20, 30, and I was working on this more like temperature checking tool. Well, the same time during the pandemic, because the company is rooted in childcare, so upwards We started out as a B2C marketplace where we helped connect families with caregivers. So 2020 came around and the city of Los Angeles, because that's where the company started, reached out and said, hey, like, we need access to your daycare network for our first responders. That led to press, which then led to more B2B companies coming in. The CEO was managing the pipeline at that point. She knew that I had experience in B2B before, and so she said, hey, do you want come help me with this. It wasn't like you're going to start the program from scratch. It was just like, we're going so fast, can you pick this up? So for the first, say, 2020, 2021, 2022, I had started the program with her. So her and I were working together on this enterprise product. We ended up going to companies like… sold to companies like Amazon and John Deere and Albertsons, a lot of large frontline hourly workforces. And during that time, I was also able to help craft the pitch, which meant talking to a bunch of people. Like, it really helped with, I think, my more spatial thinking. And at that point, it was quantity over quality. A lot of people did not know about childcare benefits. And so it was pure hustle, I think, at the beginning of the sales and that hustle, but also getting into the industry and then people knowing who I am with the brokers. I then just started having deals come to me. And I found out because of just my work ethic, like I was able to handle a pipeline that probably 2 or 3 people needed to handle. And that was one of the reasons, just because of pure quantity and being the first person that then I was able to establish myself. And then as we started to hire more people, I started to move into a manager role. But I think like most people, Maybe I don't know if you have this experience. I wasn't ready for management. I thought maybe I was. There was something about it that I really liked more selling. So we hired some other AEs. I went back down into being an enterprise AE and we hired our new VP of sales. We tried to hire a CRO that didn't work. Hired a really amazing VP of sales and now I'm strictly senior enterprise, really above 10,000 employees, 25,000 employees. Right now we have 5 AEs and we've consistently been around 5. And I think that's what led me… some of the points connected to that allowing me to be at the top.
13:53 Scott Ingram: Awesome. Awesome. Awesome. So let's go a little bit further back. The dots are starting to connect. I'll come back.
13:59 Greg Crisci: Yeah.
14:00 Scott Ingram: But in terms of like the real origin story, I mean, you mentioned the 4th grade as we were talking through some, some of your points. How did you get into sales in the first place? What led to that?
14:10 Greg Crisci: So this is going to start out as a great story and then it's going to get a little bit deep, which I know we emailed back and forth about getting a little bit deep, which is fine. So 4th grade, I remember selling these like booklets. Like I said, it was like paper. I stapled them together and people paid me a quarter. And in my desk I just had a ton of quarters and I would like play with them and the teacher heard them. And took them away. I remember doing like some other things just to get money. So like that thrill of getting some money for something was like 4th grade. That then progressed into… and maybe you were during this time… the Pokémon craze, right? Pokémon and baseball cards, the foil cards, the Slammers. Remember Pogs? And I loved the premium ones. I loved that thrill of I don't know what I'm gonna get in this pack. So those dopamine rushes were starting real, real early for me. So that was probably my, like, you're talking what, 6, 7, 8, 9, 10, 11, 12, like up until teens. Pokémon moved into baseball cards, then that moved into blackjack. There's a commonality there, right? Like you never know what you're gonna get. It's a gamble. You're always chasing the win. And this was early. For those that are in San Diego, there's like 8 different Indian casinos. And back then, I think maybe still now, there's one that allowed 18-year-olds in. I was 16 and was able to get in. We also played blackjack in high school in this back room. We'd have like a blackjack table. So the progression now is getting into that rush. In high school, I was also the guy that sold candy, and I had like 4 different people selling candy for me. I mean, I was raking in the money in high school. I would go to Costco, buy all the candy, package them up, meet the people in the morning, give them their things. They would go sell. We meet after. I give them some of the money back. I take the rest. I got stopped for that. They didn't like that I had like an enterprise. That same time I was doing lawn business and like garage sales. It was just like chasing the money. So now I'm like 18, 19. In, I'd say my 20s was getting into hospitality, which the connection there is tips, chasing the ups and downs. Like you work hard, you make money. You don't work, you don't make money. That then led into entrepreneurship. So you can kind of see the things lead to another and then they get more and more intense. Moving into entrepreneurship is riskier than getting tips at a restaurant, which is riskier. Than selling candy in high school, which is riskier. So it just kind of goes all the way down. And as your income goes up, one of the things that I started to fall into was an addiction to gambling. And that makes complete sense, right? Because I'm in sales and sales is some form of a gamble. You have the lows, you have the highs. And they can be really low and they can be really high. But as you see from my origin story, that is just how I was wired. After exploring it for many, many years, and after I've decided to live a sober life and explore everything around this journey, it wasn't just an addiction to gambling or addiction to alcohol. It was an addiction to excitement. And that's the core of it. And the history shows itself. And not many people think about that. And I think a lot of salespeople may relate to this addiction to excitement, which is the ups and downs of getting that big deal, not getting that big deal and making it through. And so I just think naturally, because I was wired from the 4th grade to like, like these dopamine hits and ups and downs, which again, some of it's just genetic, it led me perfectly into sales and especially now enterprise sales. Which is like the money's there, the ups and downs are there, you're talking to the VPs. So when you talk about a gambling addiction, a lot of it is not just about the money, and a lot of people don't know that. Some people don't even do it for the money. I didn't do it for the money. Some people it is for the money. It was more for the VIP, to feel like you're the big shot. And entrepreneurship is similar. The basis of that is ego. And then that moving into enterprise sales, the basis of that is ego. And you get into the rooms with the VPs and you're the big shot and you're making the money. It all has made sense from how I was just wired all the way from probably even before the 4th grade to now where I'm at today.
18:54 Scott Ingram: Let me ask you this. So you don't gamble anymore today, correct?
18:58 Greg Crisci: No, sir.
18:59 Scott Ingram: So how do you manage You can't quit sales. So how do you stay in this role and not let the addiction to whatever it is become unhealthy?
19:13 Greg Crisci: Yes, there's a lot of things that you can do, and there are several resources out there. One program is through the GA program. So Alcoholics Anonymous has AA, gambling has GA, and being part of those programs help you stay the course because, right, it's a fellowship. There's a similar 12-step program and that you go through, and ultimately at the end of the day, you're exploring any of your character defects. Because the addiction got to the point where it was affecting my life, that was the big turning point, which was like, I could lose everything. And there's stories out there of people losing everything. It finally got to the point where I said, I cannot make that happen. And I've been able to take advantage of all these resources so that I go to meetings twice a week. I still do therapy with my therapist I've seen since 2010. I also have a therapist that's specific to gambling that I see less frequently but at a regular cadence, and that helps keep me grounded. So there was an exploration, I think, of the character defects, which part of it was ego. Like, sales for me was the big shot in the ego. And now that there's a book… I don't know if you've read it, it's called Ego Is the Enemy… having explored that I am now much more aware of how I conduct myself, what I'm actually chasing for, why am I actually doing this. I would also say the relation to sales and gambling… for me, sales is not about the money. For me, it's just surprising some people think it is, and some people it is, like that's their motivator is money. For me, especially as like a startup, as the underdog, it's the ability to say like, I did that. I built that. I sold that. I got into that account. It's the stuff that I did versus like, it's the impact that I had versus the money that I got. That may have been dancing around some of the question, but I think that was…
21:02 Scott Ingram: No, that was, that was good. That was good. That makes perfect sense. And I think you're spot on in terms of the stereotype for sure is all salespeople are in it for the money. And the reality is that I think early in our careers, that's more frequently the case. But at a certain point, at a certain point, you're like, you know what, the money is not the most important thing. And there's more impactful things and other things that start to drive us. I'm curious about our journeys are very similar in a lot of ways in terms of I've been very entrepreneurial. I call myself an intentional individual contributor because I'm not interested in the traditional leadership path. It sounds like you had sort of that same discovery. What was your inflection from entrepreneur to sales? Was that just situational? Do you think you end up going back into an entrepreneurship type of thing? Like, how do you think about those 2 things and their differences and their similarities?
22:00 Greg Crisci: I believe my move to something more stable came from the unstableness that I caused. I caused a lot of unstableness, and you can only be unstable for so long. I would say throughout my since 2010. So like 2010 was when I was graduating college. I had a kid really young, I was 23. I was working at that agency, I was working at Chili's, the restaurant. And also my daughter's mother left the picture, so I was a single parent just raising a little girl with my parents. That was my first burnout moment where I realized I definitely burned out in probably 2011, and it was Pretty dramatic. Fast forward then to we sold the company in 2015. During that time, drinking, gambling, finding myself a workaholic because I was chasing the money. That led to another burnout, but I was all absorbed in myself. The ego was still there. And then this last time, I think because now I have a family, I've been married for about 4 years. I have a 13-year-old, a 3-year-old, another one on the way in about 30 days. You start to see that being an entrepreneur, like there's different types of entrepreneurs. And I think when you're young, the primary one is like, I'm going to be the next Mark Zuckerberg. That vision is amazing to have. The stress it can take on certain people can lead you to burnout for sure. The third time I burnt out was when I had gone into a leadership role and started hiring people, and I realized that… we can probably get into some of the leadership stuff, but I think it was that last time of just, I've admitted that I was powerless and my life became unmanageable, and I said I need more stability. So all of these years I rejected stability. I was like, I don't know if you were like this, but years ago I was like, I'm never going to invest in real estate. It's just too slow for me. It's too slow of a grind. I always liked the, like, you eat ramen noodles and then you're eating steak the next day because you got a big check. Like, that was my life up and down. That variability is not fun. So being 38 now, over the last 4 years, realized that there's more to it. The stability in traditional things are actually fine. That led me to going back into the corporate world and feeling more safe, feeling more secure, versus just trying to like make it… you're spending money now because you think that you're gonna get a million-dollar paycheck in 3 years because you're gonna sell your company. So that's, I think, going back to the tradition, going back to corporate has allowed me to do that. I will always be an entrepreneur. And I will 100% have another business or multiple businesses, but the outcome I'm expecting is not the next Mark Zuckerberg. The outcome is going to be like impact, but also sell your company for $3, $4 million. You're fine. Don't get greedy. That's amazing. You own 100% of a $3 million company. You sell for $3 million. I mean, you're set. So I think all of that has tied into me learning about ego and me learning about what's enough and I'm a man among men. I'm not the star. There's how many billion people in this world, right? And it's fine. I don't need to be the next Mark Zuckerberg. I don't need to be on the pedestal. I don't need to always have an opinion. And that, I think, has led me back into being in… it's not corporate. I'm still at a startup, but just having like a salary, it feels good. Finally.
25:47 Scott Ingram: Yeah, I want to come back to the burnout piece because I think the biggest difference in my experience between kind of the entrepreneur side and the corporate sales side. And the reason I went down that path was I was tired of managing everything. And man, you want to talk about exposing weaknesses, like there were plenty of areas that I was not great at. And to your point with ego, like you think that you are, it's just a mess. So once I realized my favorite thing, what I enjoy the most is the conversations, the impact through the sales, and I don't want to have to worry about the accounting side of things and the HR side of things and some of of the operational sides of things, and it freed up so much. I'm like, oh, I can just focus and do this and be really great at this one thing. Is… I should have asked this in the other order because I don't want to lead the witness here too much, but I mean, you talked about having several periods of hitting the burnout wall. How did you get through that each time?
26:46 Greg Crisci: I am a big advocate for therapy, and this was 2010, so even back then therapy was a little bit taboo and not really talked about. It's gotten way better, and now there's even companies everywhere, mental health. I was, I guess, humble enough to be okay. I talked about going to therapy freely, like it was a badge of honor to say that I go to therapy. So doing cognitive behavioral therapy, other types of therapy, and doing it consistently, that got me through. I have a really good support system. And support systems are at different points in your life. So back then I was in a band, if you can imagine a sales guy in a band. And can you guess what instrument I played?
27:30 Scott Ingram: You'd play the guitar.
27:32 Greg Crisci: No, it was drums, but close. So at that point, in that point in my life, right, like I had really diehard friends that got me through things. In all honesty though, alcohol got me through things. I would not want to do that again, but that addiction I think somehow got me through some of it. And like I said, if I were to go back, there are much healthier ways to manage and escape and things. And so during those times in my life, it was going to therapy, having a real close support system. I think part of it was I was driven by something bigger than money. I was driven towards proving myself to work for whatever that means and to whoever that means. But it was more than just money that drove me to want to keep going, which I think ended up being like impact and being able to show I did that. Like, that's what I did. I built that and I had this impact. I don't think if I was like in the money mindset that it would have got me through. One other thing is that when I was young, I had a kid young. And at that same time, I was in a band. And I thank my higher power or whatever it is that I had a kid, because I think if I would have went the band route, I wouldn't have been in the position I'm in now. That was a crossroad for sure. So divine intervention, whatever you want to call it, and I'm not advocating for it, but at my point at that time, having a kid really forced me to grow up a lot sooner because the 23, 24, 20, like that's when we supposed to find ourselves. And that was hard. So those are kind of the things that got me through to keep pushing those burnouts.
29:15 Scott Ingram: So lots of hard lessons, lots of learning about yourself through all of this over the years. If you could go back and start over and be a little bit more intentional, what would you do? Like if you were coming out of college today?
29:27 Greg Crisci: Yes. If I was coming out of college today, what would I do differently? Man, I think I probably would have stayed with music. And I know maybe that's not where the question was supposed to go. Maybe it is where it's supposed to go. But I think the underlying that was going towards something that I was able to be in a flow. And I'm sure you've heard about, read about the whole idea of flow and getting into flow. And if you can get into flow 24/7, you get to enlightenment and so forth. But music and playing drums was like, that was a high in and of itself. I think I would have listened less to society of you need to make all this money and you need to be an entrepreneur and you got to be the next Mark Zuckerberg, and took the path more of like, what could you do if you were not paid a dime for, for the rest of your life? And that was playing drums and music for me. And the path I took being young, and the ego was the money, the VIP, the fame. I've had a love-hate relationship with my drum set. I haven't played in many years because I'm scared to go back and play. I feel like I'm not good enough. And then there were years where I played every single day. But I think going back at that moment, it would be knowing that at the end of the day, this… like, we're here for how many years? We're here for a blink of an eye when you look at the history of the universe. Money and the quest for money and success. I think that quest led me to the burnout, and I think I would have pursued something more meaningful, if that makes sense.
31:12 Scott Ingram: Yeah, yeah, for sure. So now we can circle back to some of your opening points, right? I think that this idea of finding something that you're really just interested in and going deep. Something tells me that, that, that's a part of the way that you come across differently because of the curiosity that that breeds, right? If you're just hyper-interested in a particular industry or company or whatever it is, and your ability to go deep there, you're asking people questions, you're trying to draw them out, you're trying to just understand and gain perspective, and that becomes about the other person and not about you.
31:55 Greg Crisci: The quest for knowledge, I guess. Instead of starting the path by saying like, I want to be more novel… some people think like, I got to be novel, like, what does that mean? But the fact that you're asking that is going to lead you to a place that you're not being authentic, because everybody's seen the world through their own lens. Everybody sees it a little bit differently. If you start out by saying, I'm going to be novel, like, you've already not been novel. The other way is to go deep, and by doing that and just like geeking out on it, you will automatically become novel. You will just become different because you can hear it in your voice, you can hear it in people's eyes, you could see it because that's what they do in their spare time. In high school, I was the homecoming king, but I also was in band, which is a very like I realized that at that point that there were differences and my allegiance was to the band people because it was just… they were more real. And because of that, because of just that understanding early that there's fakeness out there, which is all the fakeness and the ego is all driven by insecurities. I mean, we're all in high school and nobody knows really what's happening. But I think by being obsessed with certain things, you will come across as novel. I think it'll just happen.
33:15 Scott Ingram: This novel idea is so interesting, and I don't know that it's necessarily wrong to want to be novel, but I think it's actually one level deeper than that, and it's wanting to figure out how do you do you best, because that is the most consistent success theme that I have found through this show, whether people realize it or not. It's when they're able to be themselves and be their best selves that they really, really shine. Because you should be pretty great at being yourself because it's natural, it's who you are. It's when you try to be something else that it all comes apart.
33:53 Greg Crisci: Yes, I 100% subscribe to that. And I think that's really exciting, right? Because basically what you're doing is you're working on yourself, you're exploring yourself, you're in the journey of you. And that ultimately, when you start talking with all the gurus and you come back to yourself, you come back to… Michael Singer calls it like witness consciousness. It's like you're in there, you are the person that is observing your thoughts. Like, you're not your thoughts, you're actually separate from your thoughts, but you're always in there. And you need to go find who that person is because most of us have been programmed either by society. Like, we have all of these… he calls them blockages… which were based off of like wanting to be comfortable. And so you create these barriers around you to be comfortable, but by doing that, you're not actually yourself. You like have this persona that you have to keep up, and then that just spirals and it spirals. And so the want to become novel, I agree, is about finding yourself, which is maybe a little cliché, But that didn't sound exciting to me though when I was 20, by the way. I don't know if that would be exciting to you when you were 20, but I wish it was exciting to me because now it's exciting to me now.
35:12 Scott Ingram: Yeah. Yeah. There's another way that you can apply the curiosity too, because you said something earlier that had me think about this just in terms of kind of the perspective, right? Like you have the perspective from within yourself, but sometimes it also helps if you have a good support system and you have people around you that you trust and you can be curious about yourself with other people, you can use them to explore And like, well, what's your perspective of me? Or how do I come across to you? It feels to me like this.
35:41 Greg Crisci: Oh man. Right.
35:42 Scott Ingram: But there's really, really powerful stuff and leaning on your sales leaders. I've done this with my customers. I've come back after the fact, like after I did a big deal, like, okay, what worked? Yeah.
35:54 Greg Crisci: Why did you buy from me?
35:55 Scott Ingram: That's a lot of where I figured out it was the authentic me that was the best salesperson. Like when I was just human and joked around and we had conversations and I cared about them and I was interested in them. Um, it had nothing to do with the pitch or the product or the way I said this, or no, no, it's just let's be real.
36:14 Greg Crisci: There was an aura about you in the room that you could feel. I remember when in 2010, when I was at the ad agency for a couple years, and we were at a restaurant or happy hour, one of the guys that I was working with, he just looked at me, he's like, you have a really trusting face. And I kind of was like, is that a good thing? Is that a bad thing? I put that aside because I was like, well, like, what does that mean? But now, if not only did he say that I had a trusting face, but he just said you have such a calm demeanor. So like, just the way that I show up is different from what I hear because I asked people, or when people told me things, it triggered something in me to go, okay, like if that's a common theme where people saying I have a trusting face or a calm demeanor when I go into these meetings, why am I anxious? Why? I still get anxious, like pitching on site, like my heart's beating a little bit. It might seem calm on the outside because there's been a lot of work on not talking as much and meditation, just calm, like not even… just don't care about the money stuff anymore. Like I just care about actually producing. The lesson there is ask people. And I even think there was a question that we were going to talk about where I was like, I forget which one it was, but I was going to ping one of my colleagues to say, like, if you had to answer this for me, like, how would you answer it? But I was scared to do that because I was like, it's hard. I'm not in the mindset right now for someone to give me feedback yet on my strengths and weaknesses. But if you can love that If you can learn to just like love that feedback, what do they say? You learn the most from your failures. Like you learn the most from the other people that are witnessing you and it'll help you, I think, either calm yourself or give you areas that you need to work on because there may have been a disconnect between what you thought you were projecting versus what actual people saw from you.
38:12 Scott Ingram: Yeah, exactly. Well, Greg, let's switch gears entirely. I want a full-on run-through of a typical day in the life, and I know you've listened to the show So the way I like to ask this is your alarm clock goes off. Tell me what time that happened. And I want a pretty detailed blow-by-blow till your head hits the pillow again.
38:31 Greg Crisci: All right. Well, I'm going to start out at 2:00 AM because for some reason over the last couple of years, I've been on a quest to have the best sleep. It was just something where this was when like sleep research was like getting big. And everybody says like, you want to be the most productive, get good sleep. I'm going somewhere with this story, by the way. It'll lead into my day. But 2 AM, I realized over the last couple years, like, I'll go to bed at like 8, 7:30, 8. My 13-year-old stays up later, which I think is fine. But then it's like 6 hours, and then I'm like wide awake at 2 o'clock. I'm up till like 4, and I'm reading Google Alerts. Like, I try not to do the doom scrolling. I try… if I'm going to scroll, it's on LinkedIn to learn something. Like, anything I do… like, you won't find me watching trash TV. So after I fall back asleep, if I do, my next wake-up is probably 6, 6:30, 7. And this is different if it's a school day or not. So right now there's no school, and I'm up at 6 6:30 because we have a puppy. She's about 8 months now, and we've been able to crate train really well. She was crate trained like within a couple weeks, but she wants to get up at 6 o'clock, 6:30. So either… it depends on… I'd say between 6 and 7 is when I'd get up.
39:57 Scott Ingram: So your alarm clock slobbers?
39:59 Greg Crisci: Yes, my alarm clock whimpers. And sometimes my wife will get up if she's awake she'll go. So it kind of depends, like there's some variables whether I'm gonna get up, she… I'm gonna let her sleep. But after that, then it is go say hi. I have another dog, she's about 5 years old. Go hang out with her a little bit out there with the pups. And then I'm into coffee. And coffee, I try to make coffee for myself but also for my wife. I like just that feeling of like bringing her a cup of coffee or being brought a cup of coffee. It's just like Such an amazing feeling. So after that, then the house is quiet and I work from home, so I'm 5 feet from my desk. And my desk right now though is in my master bedroom because we had another kid that took my office. So I'm in my bedroom like how many hours? 18 hours a day sleeping and, well, probably more than that. So I'll try to work from the couch. I like working from the couch. I'm not sure if you're a couch worker. Some people need to be at a desk. Some people like standing up. I have a pretty good indent in the couch cushion. So coffee. I then open up and I honestly start for… I think I've realized that my most productive times are about that 6, 7 AM till about 2 PM. From, I'd say, the morning up until like meetings start happening. Which I try not to book meetings until after like 11 or 12. And that's hard, obviously being in sales, but I'm not sure. There's a book. I don't know if you've read it. It's called When, and it's this idea that it's not just about like the work that you do, but it's actually when you work on it. So I've realized that my most productive time is that 7:00 AM to like 2:00. 7 a.m. to 1, that's like my most productive time. So I've made it a point to use that time to do more strategic, thoughtful things. And that could be in sales, we're doing business cases. I love doing those between the hours, the early morning hours, more like strategic connect-the-dot type things is morning hours for me. I have built a habit of any time I have to do something, I write it down. So I use Evernote, which there's probably better tools out there than Evernote, but I've just… I get into a habit of putting things in there. So I have a running list of things to do, and either the night before, like between that when I get my coffee, I will then start prioritizing like what needs to happen when. That's like the morning, right, is some of the prioritizing playing with the dogs, doing the more like in-the-zone type things. I don't, I don't know if you're like me, but when I drink coffee, it expands my mind. I get really focused, which by the way, I was able to explore that I was diagnosed with adult ADHD, which makes sense. A lot of salespeople, ADHD comes in many, many formats, but it allowed me to use that time, right, to like think spatially. So an hour, like 6, 7, 8, 9, 10, 11. Then you start getting into demos and meetings, internal meetings, external meetings. Periodically, I would say I'll go out. My daughter gets up like at 9 o'clock, my 3-year-old. So if there's a moment… actually, let me take a step back. My wife will come out and then I'll move into our room. Periodically, I have the blessing to be able to go out and just say hi to my daughter, um, hang out with her for a little bit, and then come back into work. So I try to take like little breaks here and there when I have time. Around 2 to 4, I would say about 3 times a week, I will go to the gym. This is also… I don't want to sound like I've always went to the gym. I've always struggled with going to the gym, but at our apartment complex They have a sauna and a steam room, which I'm going to tie that back to how did I get through some of the burnout. Saunas and steam rooms and some of those meditation stuff, they work really well for me. I may go do a sauna session, like a 30-minute walk, or a steam session, or all 3. That's usually like 3 o'clock to 4. So do that. That's about like an hour. Like, I try to make it an hour. Come back and sometimes have like one-on-ones between 4 and 6, sometimes end early because if I start at like 6 AM, just kind of depends on how I'm feeling, how things are going, looking at the priority list. Like, is there anything that's really due today or tomorrow morning? I would say I always, when I'm ready to like call it a day, I will reprioritize. What didn't I do? Where can move this? Can I move it to tomorrow? I'm kind of like setting up my next day, a couple days. 2 days a week I go to meetings, so I have some fellowship there. And the other days at about 5, 6, dinner. My wife comes from a family of 8. I think one of the proudest moments… she comes from a family of 8, so she's always wanted to stay home And I was able to provide that for her. And she can 100% go back to work if she would like, but she likes that traditional… like, both of our parents were very traditional, and so she likes taking care of the family. So we'll do dinner by like 6, 7. Then you're talking like bath with the kid, putting the kid to bed, which I give credit to my wife for 98% of that. Now we're like at 7, 8, and then it's bedtime. Like 7, 8. Yeah, you're like, I'm in bed 8 o'clock, 8:30. I may do a little bit of Google News. I set up Google alerts of like specific childcare topics or competitors and scroll through that a little bit. Then I put my sleep apnea machine on and I'm in bed.
46:12 Scott Ingram: Nice, nice. I'm jealous. I would love to get to bed just a little bit earlier, but that's a trick.
46:17 Greg Crisci: You can make it happen. You just gotta prioritize it.
46:19 Scott Ingram: Yeah, my wife might not be so down with it. So let's talk about about your information diet. What are you listening to, reading, watching, and when does that happen beyond the Google Alerts?
46:30 Greg Crisci: Yes, so I would say Google Alerts are great, so I'll just start there where you can set up keywords and you get the emails. I have it set every day so I can read those articles and then dig in a little bit further. I have found that Google News has been the best for me to like surface what I like I tend to stay away from politics. I try to only let in my brain what I want to let in. If you go into like just a regular Google newsfeed, I mean, you're seeing bombings and like all this negative stuff, just it's too much. And so I tend to stay away from that and focus more on like business stuff or philosophy stuff or technology stuff. And so that is done over the time. You can use Google News to like thumbs up and thumbs down, and I don't want to see anything from this. And so I love that part of it. Other stuff I like to do are industry… more like investor reports of the industry. So the care industry is I don't know how many billions of dollars, and for many, many years there were only 2 incumbents, and now there's probably like 30, 40. There's a lot of like new thesis stuff coming out about the industry and where it's going. I like reading about that stuff. Some books I'm finishing up, the book called The Untethered Soul by Michael Singer. So it's part of the journey of like exploring yourself and getting back to yourself. I like that type of stuff. The podcast… Michael Singer also has a related podcast, so I'll listen to podcasts and like the books I like. I do like some level of podcasts, but it's not as like sales stuff. It's More like self-help, but just like journey stuff, finding yourself and all the things that go with it. And that's like outside of just the sales stuff I have to read. So 10-Ks and annual reports and company stuff, right? Those are kind of the different areas. Maybe some Goodnight Moon every once in a while.
48:34 Scott Ingram: I was going to say, I remember those ages. I absolutely miss reading to my kids. They stopped putting up with that quite a while ago now. I'm shipping one off this fall, which is insane. Don't blink, man. Time flies when you're, when you're having fun.
48:45 Greg Crisci: I already have. I know.
48:49 Scott Ingram: I think of this as like the soapbox section, and I'm curious if there's something you believe that the average or typical sales professional would think is crazy.
49:00 Greg Crisci: Okay. Monologues are okay. I think most people would say can't go more than 30 seconds when you're pitching. Would you agree? What's your take on monologues real quick before I jump into my take?
49:13 Scott Ingram: Oh no, I can't lead the witness here, but part of my style and approach you will have noticed is I don't interrupt folks on the podcast, right? If you want to monologue, you monologue, and you've been monologuing, but it's all good.
49:24 Greg Crisci: Yes. And I've not necessarily done that on purpose, but that is just also who I am. There is definitely data out there from Gong that are like, your win rates can go up this much by having this many monologues. I get that. But the flip side of that is there are people that are successful having monologues. There is a percent that close more or that have better win rates when you have less monologues. But then there also are a whole population that have monologues and still have higher close rates. Right. But that comes back to, I think, the novelty in the way that I pitch. Like, I like there being a moment where I am… think of it as like a TED Talk, like a mini TED Talk. Where I'm trying to use my voice and I'm trying to use like me as a way for them to get into the passion and feel the passion as much as I'm feeling it. I would say most people would think I'm crazy for saying that monologues are okay to an extent, but you can't just monologue the monologue. You have to learn how to like slow your talk. Like you need to dive into how do you deliver a monologue. Where the outcome is the person like on the edge of their seat going like, keep going. I think that would be something crazy that are like, there's no way I would do more than a 30-second monologue. I wouldn't. I would argue that I do a couple-minute monologue because I'm telling a story and I want them to get on the edge of their seat and just feel how passionate I am through this computer. Like, if you can get them to feel that through a computer, I mean, that's amazing.
51:02 Scott Ingram: Yeah, I'm gonna step up on the soapbox in the soapbox section because I think…
51:06 Greg Crisci: let's do it…
51:06 Scott Ingram: drives me crazy, all of these aggregated stats. Take the monologue example, take anything that says, oh well, if you do this, you'll be successful or you won't be successful. If you tell jokes during sales calls, you're going to be successful or not. I'm like, well, that's so individual. And I think it comes back to this novel, is it who you are kind of a thing. Like, if that's your style, and it works for you and you're able to execute that well, then you will be successful doing that. Even if the data says on average, people are not successful with that. So I think we get so hung up on this. I hate, I'm going to say it. I hate aggregated data like that. And that's why I do this show, because I think it's so much more interesting to get into the individual. I mean, what these tools really need to start to do is say, Scott, when you do this, you are better, or when you do this, it doesn't work and your rate goes down. But trying to compare the unique Greg to all other random salespeople, it's garbage. It drives me crazy. And I think it leads us to do… again, it actually leads us away from what we might be natural and successful in doing. But I read some study that said I should start using the F-bomb all the time. Well, if that's not your style, it's really not going to come across well.
52:35 Greg Crisci: Yeah, I think going back to like what I had talked about throughout my life, I would shy away from the traditional things. Everything that everybody else was doing, I would go the other way. So when I hear these stats too, I look at it and I go, I don't want to do that because if everybody's going to be doing that, I need to do something else, right? I can't do that. But then there's also the flip side. Like, I've been trying to formulate this argument, so I'm going to say it and maybe you can help craft it. When people say things like, maybe it was like those that cuss have a 70% lift in their conversion, whatever it is, there's the opposite though. The other 30% of people, what are they doing? Again, I'm trying to like formulate what I'm trying to say because I've been trying to think about this for a while. About the aggregated stats. It ties back to though, when I see something, I want to go the other way. So if someone says you have to drop the F-bomb because your conversion rates will go up, what about the people? There has to be people that do not drop the F-bomb where their close rates are significantly higher than those that do. You know, like, I think I kind of got it out there, but I've always been like, sure, that's a great stat. Well, I don't want to drop the F-bomb because now everybody's going to do it. It was like cold email when you have those HubSpot inbounds and then they have those sessions where the cold email marketers are like, you got to put oops, dot, dot, dot. Then everybody does it. And then like, it's good for like a week and then everybody does it. So when I see those stats, I'm just like, oh, I got to go the other way. I have to like go the other way. And I was like, I'm just wired that way. So instead of saying, oh, I'm going to latch on to that, it's like, yeah, like I want to not do that. I want to do something else.
54:18 Scott Ingram: I think that the idea that if we can agree that the common way When something is overused, let's say overusage leads to underperformance, right? When everybody is doing something, that thing stops working. To your point, as soon as we put out a study that says, oh, you should send an email on Tuesday at 2 o'clock, well, what happens next? Then all the emails come at Tuesday at 2 o'clock. Tuesday at 2 o'clock doesn't work anymore, and you would be much better served to your point, by going in the opposite direction. And it's definitely one of those kind of counterintuitive things. And that process, I mean, it's just been accelerated so fast because we're all sharing this information and everybody's, oh, we want to put out these stats and all these things. Whatever the lines are about statistics being like the highest form of lying, heck, 83% of statistics are made up on the spot anyway. To me, it's all garbage. Like this aggregation idea. Is just leading everything astray. Because you actually articulate a really good point. If I do this and that leads to a 70% higher close rate, but what if we just isolated the single top performer and turns out they close 3 times higher than that and they never do that? So now what can we learn? Well, nothing. Throw it all out. It's all garbage.
55:43 Greg Crisci: Yeah, I think like maybe when I would hear those stats of like Dropping the F-bomb increases something. My brain is like, who thought to do that? That's interesting, right? Like somebody had to think that up. Somebody had to make that connection and then somebody had to go like do the research. That's kind of fascinating. I'd want to like talk to that person to be like, how did you get to that? And I think this is something that I, and maybe we'll talk about, I don't know if we were going to talk about habit. That I would recommend. Maybe we can steer into that because it's related. One of the things that I have been doing since I can remember is when I would feel something that triggered me, like emotionally, whether it's like an ad, something that I saw, or something on the radio, or something on TV, I felt it. I would stop and say, why? What did they just say that made me do that? Because that's fascinating, right? If you can figure out how to trigger somebody emotionally, it happens everywhere. But I came to the habit of stopping myself and going, wow, like, why did I like that? Why did I like the way that they said that? Or why did I like the way that they did that? Also relative to that, anytime I would do that, I would also write it down, by the way. Like, I have a whole notepad in my phone about like moments that triggered me or ads that triggered me. But I also did it with startup ideas, and that taught me to get to the root of things. Like, how did they put those together? How did they put 2 and 2 together? An example would be… I forget the company name, but they were disrupting the remittance industry. The old way of doing it was like you would have your bank and you would have to like go through this SWIFT system or like this legacy system that had all these checks and balances. Of moving money from like the UK to the United States or whatever. That was the way that it worked. You went from one place to the other. But the aha moment was like, that costs a lot of money. Like there's a lot of regulation in that. But what is happening every day is that people are actually sending money to each other in the US. They ended up doing was saying, I don't need to send money from the UK to America. Because there's already money flowing through people in America. So I can just kind of reroute that money from people already in the country. So the money actually does not have to leave the country, which is where the expense came from. And it was like that aha moment that I was like, how did you come up with that? And that applies to like any idea. How did you as a founder come up with that? Like, what led you in your life to get to that aha moment So I would write all of these down. So that has been my habit for many, many years because as an entrepreneur, I'm not the entrepreneur that is going to invent something wildly new, like the really innovative stuff. I'm the one that's going to like connect the dots that nobody saw. And I knew that in order to do that, I didn't want to reinvent the wheel. So in order to not reinvent the wheel, I just became aware of what everybody else was doing and I wrote it down. So that at some point in the future I can say, oh, that business model was interesting, or that connection was interesting, and try to apply it in a unique, different way to… I was in the trade show industry. I took marketplace concepts or other concepts and applied it to just a different industry. And that stuff happens every single day. So going into the habit part of it, detecting when you feel triggered and stopping and figuring out why, like, I just loved doing that. But also, if you want to get more like the business stuff, look at their business model and go, what was the aha behind that or the why behind that? Like, why did they do that? And write it down and get into a habit of doing that. And you're going to have just this whole bank of you trying to get to root cause, which I think is a really great skill to have. Little soapbox there, but moved into habits.
59:52 Scott Ingram: Yeah, I love it. And I think this idea of… I think of it as cross-pollinating. Right? It's like this industry has done this thing this way forever. And yet in this other industry, we could apply that thing or vice versa. And it's completely novel and completely unique. And nobody's ever done this. Like, well, this other group's been… this is par for the course. I've been doing this for decades. Yeah, I bet. Is there an example of that that you have incorporated within Upwards? And being one of the first sellers there, I'm sure you've invented half of the sales process and half of the positioning anyway. But is there a specific example of that?
1:00:28 Greg Crisci: There has to be. Early on, Upwards was a B2C company. I mean, it's kind of D2C, and then it was B2C. And I'm trying to think of… there was this whole idea of ecosystems and like network effects. There's like this foundation of… there's these foundational companies that marketplaces have blown up over the years and like Marketplaces were like new 10, 14, 15 years ago, and then they became entirely huge new businesses. And then when you start looking at the players in the marketplace and why a marketplace between those players is interesting, you can apply that marketplace idea to Upwards where it started to become not that we were just like we helped families, public families, and then we helped employers, the ecosystem model was like, that is the model we have to get to, which was government has to be part of this equation. Employers have to be part of this equation. Families have to be part of the equation. Caregivers have to be part of this equation. Seeing how other companies like expanded their marketplaces to go from just like 2 stakeholders to more. That at the time was fascinating. That was new years and years ago. Like, oh wow, like you're adding a 3-sided marketplace. That's fascinating. How did you even think to do that? And where does value cross and where it doesn't cross? You take these aha moments of like, oh wow, you brought in different parts and you made it into an ecosystem. And so then that concept was like, well, we could do that at Upwards. Government needs to be a part of it, employer needs to be a part of it, family and provider, and you could also throw in philanthropy. So it's like 5 or 6 different constituents. But if you sit at the middle, because these companies that you're researching are like, they win because they sit in the middle between everybody, we took that concept over. It's not anything new, but it was new years and years ago, and applied that to then expanding the model, which that, like, that kind of stuff I was able to help with because I was like the only salesperson and I had that. It was just right time, right place, right attitude. That's like a simple example of using aha moments that have already existed in business models that people already existed and just saying, we're going to do that and running with it. I'm sure there's others, but that would be one thing I can think of.
1:02:58 Scott Ingram: Yeah, man, being the first seller in a startup, it's such a unique thing. I've got another close friend who's in that same position. Actually, he's been on the podcast. And when you move into a large organization with a very established product and everything else, like there's a sales process, you just step into it. This is how it works. These are all the steps. This is how we position. Everything is just laid out for you and you just kind of like run the play versus you have to draw up the plays. You're like, I don't even know how many X's and O's there are on the field, let alone how this is all going to move. And it's one of the things that, as I help people sort of think through their sales career and where they're best positioned, you really have to understand that about yourself. Like, are you comfortable in that place where you have to invent freaking everything? Nothing's going to be given to you. You're going to have to create it because it does not exist. Or Are you just an executioner? Give me the system and I will run that system better than anybody else on the planet. You just have to understand that. And some of that is size of company, maturity of company. There's a whole lot of other dynamics there I think you have to consider because I've seen plenty of people who are wildly successful. I mean, in both sides, right? They're wildly successful as an executioner. They go to a startup and it's a disaster and vice versa. They're completely different things. I mean, it sounds like you've pretty much always been in this more entrepreneurial startup-y type of space where you've had to invent this system and do some of this cross-pollination along the way. Is that fair?
1:04:36 Greg Crisci: Yeah, totally. And I think it comes back to my addiction to excitement and the ego and wanting to like, I did this, this is what I did, and it's all about me, me, me. But I do agree that understanding and wanting to try both of it, both models, I don't think I would be happy. I probably know I would not be happy going to a large company with everything already figured out because I need to be a little bit different. And that's just me. But like you said, there are people that are like, I love that. I love structure. And that is totally fine.
1:05:14 Scott Ingram: Let's pivot that because one of the things I like to ask is just what advice you would have for somebody that's getting started in a sales career today. What would you tell them?
1:05:22 Greg Crisci: This one is definitely a harder question just because I have been scarred. The natural part of me, I want to save people. Like, a lot of people want to save people, but the latest craze is stoicism in philosophy. So really, the stoicism is you can't control what people do to you, but you can control how you respond. Part of me is like, not don't do it, Like I said, it's hard because I burnt out 3 different times in sales, and I don't want to say that. It is a great career. It's an amazing career. So I want to preface that with my own story is different than other people's stories, and maybe this will help someone just think a little bit about what they're getting into. If you're just getting into sales, I would think about, are you okay with people saying no? Many, many, many times. Like, do you take that personally? If you take that personally and you still want to be in sales, we got to work on it. And to work on that, you would want outside perspective, therapy, reading about it to get yourself out of that. Because I think I do see when people start, the no and the consistent no can get to a lot of people. I would Also then say, if you are starting out now, keep front and center your mental health. And that means having some support system, having some awareness that things are going to go up, things are going to go down. I think that's really important because people, I think, get stuck there. I think those would probably be like some suggestions I would have when you're getting into it. I also am an advocate for You're young. Take as many big risks as you can. Do it then. That is your time to do the craziest things, test the craziest of things. Everything leads to another thing. Every stepping stone will lead to another thing. Do it. Get into sales. Try it out. Go do it. I would just… from having done it and having burned out many, many, many, many times, for me, the drive to be in the boardroom, which I was able to finally get at the boardroom table, like I did that. I didn't like it. I didn't like it. So all of this time I spent and energy I spent just obsessing over money and being in the boardroom, it was not worth it for me. Some people, you get to that place because that's who you are and that's what you want to do. Go ahead and do it. So that would be off the top of my head, some suggestions.
1:08:00 Scott Ingram: And what about… let's think about this directly for somebody that has hit that burnout wall. So somebody, they've been in sales for a while. Some number of years and they're like, oh my God, I'm at that wall. What do you tell them?
1:08:11 Greg Crisci: If you are at that wall now, reach out to somebody. I think talking it through, writing it, journaling it, getting it out, I think is really, really important. If you're at that wall of burnout, man, I think you got to do some self-reflection. You got to do some self-reflection. You got to do self-reflection. As you can tell, I'm pretty scarred from my burnouts. My last burnout was like last year. I think I'm still getting over it. And so I'm trying to think about the things that when I was at that stage, what got me through too was I had people around me that I honestly confided in. That was really, really key. And I would let the conversation go and I would listen to their feedback. And ultimately it came down to priorities. And who I really wanted to become. I think it's probably the most cliché of it, but I sat down and I said, I want to be there for my family. But in order to be there for your family, you have to do certain things. So every choice has a consequence. I learned that the hard way. If you're there at that moment where you're like burned out, reach out, start talking through it. It's not the end of the world. We have so many years ahead of you. You've already learned so much. You have the choice now. You get to decide what you do next. And that's that.
1:09:35 Scott Ingram: Yeah, I think the reach out thing is the first step. I mean, it's not to make this a sobriety podcast, and we've done several. And in fact, let's see, if you go to top1.fm/sober, I think is we've kind of collected the episodes where this has come up. And for some, it's been a huge, huge thing. But the first step is just acknowledging it. Like, you know what? I'm fried. This is not working. So that's step one, because you can't ask for help if you haven't gotten there. And then it's just a process. I mean, I've been through this recently, and sometimes it takes a while. Like, what exactly is wrong? Where's the disconnect? What do you need to reconnect to, to pull yourself forward? I mean, asking yourself the question about, can I do it where I am? Can I do it In this role with this company, or does that have to change in some way, shape, or form? There's a lot of stuff there. I don't think you can do this career for a long time and not get to this place. So we've almost all been there. So come to the summit, join the Sales Success Society, right? Like get plugged in because man, we'll tell you.
1:10:45 Greg Crisci: And it's hard. Like part of me is like, you want to save them. Right? You can't control what people do. You want to save them, but they're going to have to experience it themselves.
1:10:55 Scott Ingram: I think this is also the ego is the enemy piece. You have to be willing to admit there's a freaking problem here. And the worst part is the problem is you, which is really a blow.
1:11:07 Greg Crisci: Yeah.
1:11:08 Scott Ingram: Greg, you've done a pretty fantastic job of leading yourself through many of my, my typical questions, and we've covered a lot of ground. Is there anything that we didn't touch on that you hoped that we would?
1:11:20 Greg Crisci: I like the flow of things. I liked how the conversation just flowed. I wanted to make sure that I got out to reach out. There's resources out there. When I finally admitted that I had a challenge and I had to call one of the numbers that you see on all the ATMs, That was a big moment. I didn't want to do that, but man, that changed the trajectory of my life, just making that call. So for those that are out there, it's hard, it's tough.
1:11:53 Scott Ingram: Greg, what immediately preceded that? What was it that you're like, you know what, this number has stared me in the face for years, but I actually need to call this? What was that?
1:12:04 Greg Crisci: That was I would say definitely a little bit personal, but I think it's important. I think there was a moment right before that where I essentially got caught and I lied, and I finally, I think after the years of like being in this addiction, stepped back and was like, damn, I'm actually hurting somebody else. And at that point it was like I have tried other things. I thought I could do it myself. I thought I can get over it. And I was like, I could lose all of this. I could lose my wife. I could lose my kids. And I think I just came out of this like, it's not about you anymore. Like, you are not the center of the world. That came out of just years of doing what I was doing. Before that, it was that idea It was the, I could lose everything that I think is really important to me. I lied. And that was like, I never did that. And the one time I did it, I got called out and it felt really shitty. The first step is admitting we were powerless and our lives had become unmanageable. And that's what happened. I didn't know what else to do. One of my colleagues says, you have a good way of Gregging your way out of things. And I was like, I can't Greg my way out of this. I needed help and I found it and it was there and it was willing and it's been there the whole time. I just never saw it and I finally took it. And honestly, it's been the best thing that I think I have done and I think it saved a lot. That is kind of what happened right before I was like, I got to call this number.
1:13:44 Scott Ingram: Yeah, that's awesome. That's awesome. Great stuff. I always like to wrap this up on something actionable, right? Folks are listening to this and we've had a great conversation. But what would you encourage them to do? What's the action they can take over the next week or 2 that's going to improve themselves and improve their results?
1:14:03 Greg Crisci: I'm going to suggest more of something foundational, something more foundational that it can produce immediate results, but it is a foundation for, I think, the rest of your business career, which goes back to the 2 things of when you feel triggered by something, stop. There's a saying, they say catch it, check it, change it. So you catch it, you think about it, you check it. Like, what happened? Like, this applies not to just like being triggered by an ad. It could be a thought that you have, a conversation that you have, but you catch it, you check it. Is this right? Is this feeling right? Is this thought right? Or in the business world, like, why did they do that? That's really interesting. And then the last part of it is you can change it. You have the power to do all of that. The first advice is like, tune in a little bit when you feel yourself being triggered by something. Figure out why. Like, why did that happen? It's not only helpful for you as a person, but also if you know what triggers you, you use that as part of your pitching. You become able to influence and have people actually feel something outside of just, I'm going to be here and give you a pitch. Like, I want people when I pitch them or talk to them to like feel something outside of just we're going through the motions. In order to do that, you have to know what it feels like. And in order to know what it feels like, you have to catch it when it happens. And the second thing that I think is actionable is the aha moments of things. And I mentioned how I do it, which is when I look at something or when I hear something in the context of like a startup or a business model, and I go, that was really, really fascinating. And then you kind of got to dig a little bit deeper to be like, how did they put that together? That could take a little bit of research. Like, you research the founder and you're like, oh, for me, I was in the restaurant industry, so The tipping company that I started, that makes sense. I was in it. And then writing it down and getting into the habit of doing that, you're going to be able to start identifying root causes a lot easier, which is what the enterprise salespeople do. We have to try to dig, figure out why things are happening. The actionable one is test that on what is just available. And the ones that trigger you emotionally are the ones that are probably the most impactful ones, or the ones that are really like game-changing. Because if they're triggering you emotionally, like you're not special, other people are going to be triggered by emotional, and other people will have the same emotional reaction. And then you just dig a little bit deeper. Well, why, why did they do it that way? Why did they do it this way? And that leads you to some level of root cause analysis, which is exactly what you're doing as an enterprise rep or even in sales. You're trying to get to that root cause so that you can layer on your services to solve that root cause. So that would be some things I have advocated when I mentor students is keep that journal of both when you're triggered by things, feelings, why, explore it, keep exploring it. And then if you find something that's just like, holy shit, how did someone come up with that? Write it down and you'll refer to it in a year from now, 2 years from now, 5 years from now.
1:17:35 Scott Ingram: Awesome. Greg, this has been a blast. Thanks for taking the time.
1:17:38 Greg Crisci: Of course. Thank you so much for having me. Thanks for listening to the Sales Success Stories podcast. To be sure you never miss an episode and for an invitation to our Sales Success Community powered by Influitive, subscribe to our newsletter at top1.fm.

