Rick Nucci On Selling A Company To Dell And Raising $70 Million To Make Relevant Internal Information Available To Enterprise Teams

In the ever-evolving landscape of tech startups, few stories are as compelling as Rick Nucci’s journey from founding Boomi to launching Guru. A serial entrepreneur with a track record of success, Rick’s career is a masterclass in leveraging market opportunities and navigating the complexities of scaling a business.

Rick’s company, Guru, has attracted funding from top-tier investors like FirstMark Capital, Emergence Capital, MSD Capital, Slack, and Thrive Capital

In this episode, you will learn:

• Emotional durability and EQ are crucial for navigating the highs and lows of entrepreneurship.
• Identifying and acting on significant market shifts, like the move from on-premise to cloud software, can be a game-changer.
• Personal pain points and experiences can fuel innovative solutions and drive new ventures.
• Strong relationships with investors and partners can greatly influence the success and stability of a startup.
• Shifting from traditional business models to modern ones, such as SaaS, can provide a competitive edge.
• Building a steady and resilient team with high emotional intelligence is essential for overcoming challenges.
• Focus on solving real, pressing problems and ensure your solutions offer significant value to stand out in crowded markets.

 

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About Rick Nucci:

Rick Nucci is co-founder and CEO at Guru. He brings twenty years of experience in creating category-leading software solutions and companies.

Prior to Guru, Rick was the founder and chief technology officer of Boomi, which defined and led a new segment as the first-ever cloud integration platform-as-a-service.

Boomi was acquired by Dell in 2010, and Rick went on to run the Boomi business for Dell as its general manager, helping grow the organization into the industry leader it is today.

Rick frequently speaks at industry events about startups, SaaS and cloud computing. He holds a Bachelor of Science in Logistics, Materials, and Supply Chain Management from Penn State University.

Connect with Rick Nucci:

• LinkedIn
• TheOrg
• Crunchbase
• RocketReach

Read the Full Transcription of the Interview:

Alejandro Cremades: All right. Hello, everyone, and welcome to the Deal Maker Show. So today, we have a really amazing conversation in front of us. you know We are going to be speaking with a founder that has done it you know a couple of times ah with his first company, actually. you know He sold it to Dell. Then Dell sold it for $4 billion. dollars I mean, it’s kind of like unbelievable the value that they were able to create there. ah and they And now, you know, he’s embarked in a rocket ship, and we’re going to be talking about it as well. So again, brace yourself for a really incredible conversation. So without further ado, let’s welcome our guest today, Rick Nucci. Welcome to the show.

Rick Nucci: Hello, hello. Thank you so much for having me. Excited to chat with you.

Alejandro Cremades: So born in Pennsylvania. So give us a walk through memory lane. How was life growing up over there?

Rick Nucci: Oh, boy. Yeah, well, you know, there’s ah there’s ah there’s an amish Amish country in Pennsylvania, and that’s that’s sort of where i from where I’m from. I’m not um um Italian based on my last name. That might be obvious. But um yeah, sort of grew up outside of Lancaster, Pennsylvania. and um really was there um my whole life until I went to college um and um moved to Philadelphia ah in 1999 and have been here ever since and actually have had the plenty of moments to maybe move or do a startup in a more maybe predictable tech hub or something like that but actually have become an enormous fan enthusiast of Philadelphia. I think it’s a wonderful city so I actually love love living here and and do it by choice.

Alejandro Cremades: how How was it like for you to have both parents, entrepreneurs, and and how was it like to to be able to experience the going through the cycles for them?

Rick Nucci: Yeah. um And, you know, look, for for those that have been on the journey, I mean, there’s plenty of ups and downs. It’s never the way it’s reported about then the and the breakout stories we read. It’s always that squiggly line with lots and ups and downs. And that’s what it was like. But um I would say it normalized the experience for me. It felt Um, it felt like this is something that people often do. And, um, both of my parents, my, uh, my father bought a small business and ran it, um, and grew it for, I dunno, most of my life that I remember can think about that’s what he was doing. And then.

Rick Nucci: ah My mom also opened a retail store in ah in a mall in the in the area where where we grew up that was sort of tied to the to the other business. And like that was like what they did. And so it was great. And it had like everything. It had its ups and its downs. But I would say for me, it it made me feel as moments came up and I was like, look, I think I think i want to start something. you know it It didn’t feel maybe as foreign to me as it otherwise might.

Alejandro Cremades: So then in your case, you know like you went to college, and then you know it sounds like you went to work for another company versus like starting your own. I mean, what what happened there? what were What were you waiting for?

Rick Nucci: Well, i think um I think I was figuring out what the heck I wanted to do. I mean, I went to Penn State University, and my ah major was business logistics. And about halfway through, I was like, oh, no, I’m actually interested in technology much more. It it was the first moment of like an area of you know career work where I felt a draw or a pull. um And so long story short, rather than like changing majors or going through all that, I went to work for a logistics software company. It was really an ideal combination. I don’t know that I thought about it that way at the time, but it was an ideal combination of being able to get myself into technology while still leveraging my major. So that was what I did. And so it wasn’t like in college, I was sitting here going, when am I going to start you know my first company as much as like,

Rick Nucci: Wow, technology is fascinating. You know, I’m a big music guy. So like, I just bought all my music on CD now.com. And I just made some, you know, I clicked around and these things showed up at my house, like, i I’m all in this is like, this is amazing and revolutionary. And then it kind of went from there. But but but I did, I only was at that company for two years. saw the pain of integration firsthand, which is what Boomi does, um saw that firsthand, and with two other coworkers at that company, we left and started Boomi. So that was in 2000. So i really I really was only working at another company for two years. I was 24 years old when we started Boomi. We’d go visit customers. I couldn’t even rent a car yet. you know but like

Rick Nucci: um yeah yeah zero regrets. I mean, quite the opposite. Really, really fortunate that I that I ended up doing that and kind of jumping into the the pool, so to speak, at such a young age, because I think I just my rate of learning, I feel like just skyrocketed.

Alejandro Cremades: so Let’s talk about Boomi. Because Boomi was quite a success. i mean You guys ended up going through an acquisition with Dell, but you were talking about like leaving as an employee you know the company that you were working at with your co-founders and starting this other company. How was that transition? you know That sequence of events that needed to happen for you to be like, it’s it’s time to to get this thing done. It’s time to take ownership of my own future.

Rick Nucci: Totally. Yeah. I mean, it was it was this build up series of conversations with my two coworkers, this growing energy of like, yeah, we should do this, this this kind of mutual encouragement, like, hey, we should take the plunge and do this. And the this was that we were observing the problem of integration firsthand. I mean, look, forever and and in the enterprise, companies of all sizes, you you have to connect data between these different systems. You have to do it in an automated way. The the systems literally don’t work. They don’t run unless they are properly integrated together.

Rick Nucci: That’s a very well-known thing. But the way it was being done back then, broadly speaking, was people were just writing code. It was very relative to today, primitive technology. um But it it was it was very cumbersome. It was always the the problem. whenever the logistics software that I was working at was being deployed to customers, integration was always what the problem was. It was always the issue. It was always the like reason the customer Go Live was getting delayed or whatever. And we’re like, man, this is a product opportunity. This is what we should do. And so so it was the combination of like observing the pain firsthand, thinking the, hey, there’s got to be a better way feeling. And then um the the the sort of like mutual encouragement with this core group of folks where we were like,

Rick Nucci: Like, hey, let’s let’s like actually do something about this. And and so that that combination, I think, jumped us you know jumped jumped us into the to the world of starting our own business.

Alejandro Cremades: So then walk us through the journey of Boomi, because also with Boomi, what was the business model there? How were you guys making money? I think that’s for the people are that are listening to get it.

Rick Nucci: Totally. I mean, Boomi started its life as an on-premise software sold with a perpetual license with maintenance. The way software used to be sold back then, again, we started in 2000. We had our first paying customer in 2001, um and and that was the business. and the the the the We call that Boomi 1.0. The real challenge and the learning that’s just been seared into my brain forever, and I think we’re seeing it play out now in the AI world in in in a different but analogous way, is as we got into this space, there was never a question that it’s a must-have product ever. There’s a must-solve problem. Businesses must integrate their software together. That’s that’s known and obvious.

Rick Nucci: What we realized when we got into it was, wow, there’s a hundred companies doing some version of this very, very crowded market. It was, I think without having any foresight into the market heating up in a big way in this time period. And that’s great, but also was really, really hard to stand out. And like, I remember. Microsoft launching a product called BizTalk in 2000 or 2001 that was very, very competitive. And we’re like, yeah, this is probably not great. And Boomi struggled, I think, as a result of that for several years um in this, how do we stand out where a smaller startup, we were competing against companies that had raised 30, 40, $50 million dollars in venture capital.

Rick Nucci: you know At the time, I think we had raised about a million dollars in angel investment. and um we Long story short, but like we we need to change. and and and At the same time, what we started to see happen was the beginnings of cloud and and SaaS. um I think SAS really was probably the name we that that everyone was starting to use back in 2005, 2006.

Alejandro Cremades: you

Rick Nucci: We were early adopters internally at Bumi of Salesforce dot.com. We were early adopters of NetSuite and we were sort of bought into this idea of like, Boy, the way on-premise software is sold and delivered is just drastically ineffective and absurdly expensive. And SaaS is going to change all that, et cetera. We said, OK, imagine that happens. And this is really, I think, a blueprint that plays out so many times in tech historically. Imagine that big sea change event happens.

Rick Nucci: That is, you see enterprise software shift from on-premise to cloud. And if that were to happen, how would integration need to work? Because it would be quite different than it would need to work in an on-premise world. When you have everything in one data center, the way you integrate it together is quite different than when you have some things running on-premise, some things running in the cloud, connecting different clouds together, et cetera. So we said, OK, we’re going to create a brand new product that assumes that future is true. And we called that um product ah IPAS, or IPAS Product Integration Platform as a Service. And we launched that product in 2007. And that was um way early. I mean, we’d talk to customers, and they’d be like, what well, i’m like I got Salesforce, but you know I don’t really have a whole lot of like SaaS stuff to be like connecting up. right So we were we were definitely early to market, which was a strength and ah and a weakness. I think the weakness was,

Rick Nucci: um We really needed to learn how to find those early adopters. The way that we did that was we partnered with other SaaS companies. um And by partnering with those SaaS companies as they were selling, you know, success factors to Leo, um salesforce dot.com, NetSuite, as they were deploying their products to customers, they had to integrate them. And so and so it was sort of created this natural pull for us, great. But the strength of being that early was it gave Boomi the ability to be sort of the you know category re-creator, re-inventor, what used to be called enterprise application integration, the on-premise days, got reinvented as integration platform as a service,

Rick Nucci: Gartner finally ah published a magic quadrant. Boomi was very top right. And that really, really took off, you know, Boomi. And then in 2010, we were acquired by Dell. And Dell was really looking to get into the software world and and go beyond hardware. And that drove them to acquire Boomi as an asset. um So I’ll pause there, but that was a, you know, I think that shift and transformation um and bet has guided a ton of my thinking, you know, throughout the, you know, next sort of decade and a half of my of my work.

Alejandro Cremades: So walk us through the acquisition. How was that like? Walk us through the process.

Rick Nucci: Yeah, um I mean, in hindsight, it was a very um it was a very ah good acquisition. and And I say that meaning like, I’ve heard many horror stories. um You know, it was it was a very fascinating experience for me because it was a competitive acquisition. There were two companies competing. um and bidding on Boomi. And they both sort of manifested organically because we had partnerships with both of them. Dell obviously ended up being the the winning one, but it was sort of a fascinating you know negotiation. It was certainly stressful. you know This is your baby kind of thing. So there was a lot of that happening.

Rick Nucci: But Dell had brought in um this guy named Dave Johnson who ran k corp dev at IBM before joining Dell and had done 100 M and&A transactions. And you could really feel that through the process because they just had this, you know, they had it down. from due diligence to acquisition, to promising what they were going to do post acquisition, to following through on those promises, to setting up Boomi for success. Of course, there’s the, oh, we’re part of a huge company annoyances that happen. By the way, Dell told us that. I’ll never forget they set us down, the the HR team, and they’re like, so everything that you guys are used to doing, expect it to take about 30% longer than it used to take.

Rick Nucci: We’re like, okay, good. At the time, I didn’t really understand what they meant because I never worked for a company as big as Dell in my life. But afterwards, I’m like, okay, I understand what they mean because there is just stuff. like You have to do HR differently. You have to do finance differently. You have to do IT t differently. You just have to. and so like Sure, if that’s like the stuff that’s annoying you, talk about a first world problem, right? So good acquirer, good process. They let Boomi run untouched. um I remember clearly my my bosses at Dell, you know they were great. And really it was a very autonomous structure. It was like, look, we’re gonna fund the business. We wanna fuel its growth. We want you guys to run it. We wanna protect the culture.

Rick Nucci: And they really did that. And I really was in no rush to leave. And I always named them as a great acquirer. And they really were. And when I did leave, um I did it over a six month period because I wanted it to be a non-event that the founder was leaving. I didn’t want it to be this sort of dramatic thing or have any potential negative impact to Boomi. And so I remember in 2013, January, sitting down and saying, like, hey, listen, like, I’ve got to do this thing. I’ve got to start. I’ve got to start, Guru. I’m just like feeling it. um But I’m not in a rush. And so let’s sort of assume that by the summertime, I’m kind of phased out. I want to make this easy. I’ve got my successor already lined up, Chris McNabb, who did a fantastic job running Boomi the next 10 or so years after I left. um and so And so that was kind of the story. But yeah, looking back on it, it’s like um great experience, great acquirer, the things that were quote unquote, annoying, you know first first world problems. They did they did write by the Boomi team.

Alejandro Cremades: and they ended up selling for a lot of money.

Rick Nucci: and then And then fast forward to 2021, they sold it for $4 billion dollars to private equity. And um I think that was a phenomenal outcome for Dell and and for Michael Dell.

Alejandro Cremades: That’s incredible.

Rick Nucci: And I think it um set up Boomi for the growth and the trajectory they are on now, which is really phenomenal. And ah they are continuing to innovate in the space. They are fully leaning into AI in their world, just like we leaned into cloud in the early chapter of Boomi. And i think it’s I think it’s amazing. And so they now yeah they now are running um as their own independent entity and I think have have huge opportunity ahead of them.

Alejandro Cremades: So then let’s talk about Guru because, you know, obviously after such a successful, you know, journey, you know, I mean, when Guru, the idea comes knocking, I’m sure that you thought about it, you know, a few times before taking action.

Rick Nucci: Yeah.

Rick Nucci: Absolutely. Well, you know, it’s the whole like, uh, if you could go back to high school again, you know, what, what would you do do a different thing? But I mean, like Boomi Guru, um, was born out of a personal pain. And what we saw happen at Boomi was, um, knowledge sharing and being able to, you know, allow employees to self-serve quickly, find the answers they need to do their job, um, is actually immensely difficult. it’s it’s it’s broken um and and you know it’s it’s it’s ah arguably even harder or or or even more broken today because of the proliferation of SaaS and the amount of places where knowledge and information is siloed across the company. and The way we saw it manifest was

Rick Nucci: um internally, it’s everything from like, how do I position against a competitor to how does this new product feature work to internal process and procedure around HR or IT, t right? i think I think we all can sort of, we we all sort of live the pain in our work of needing to find this information and find it quickly and be able to understand if what we’re finding is actually accurate. And we just tried using a bunch of products. There were, there were wikis out there and intranets out there and, you know, Our belief is that those those categories of software have have just failed. They’ve just failed failed customers. um There are some good you know nuggets taken out of them, as happens with all old categories of software. But you know we tried using all those. We’re like, there has to be a better way, essentially. And that and that really led us um to start Guru and built the… you know I remember sitting at a at a Gartner conference. This is like the moment. right I remember sitting at a Gartner conference and

Rick Nucci: There was a session and it was about an intranet vendor, a big one, a very big one. And the event start the session started and I was sitting in the back because I just wanted to learn at this point because I was like, I think I want to do this right. And the room was full of customers of this vendor. and up on stage was five Gartner analysts. The vendor wasn’t in the room. it was the It was the Gartner analysts and the customers. And the session went off the rails in the first 10 minutes. Whatever agenda they had got completely derailed. And what it became was this very passionate,

Rick Nucci: frustrated energy in the room about the internet and why it wasn’t doing what it was supposed to be doing and when was it going to work in the cloud and when was this going to happen and when was that and I and i was blown away. I’m like first of all the vendor’s not even here. like These poor Gartner analysts are sitting up on stage like trying to answer these questions like they’re product subject matter experts. It was it was fascinating. and I walked out of that session and I’m like, that amount of energy and passion around something like an intranet, I have to like i have to start this company. and like That was literally like the moment.

Rick Nucci: um And and and started guru with with Mitch Stewart who’s my co-founder and cto he and I work together at boomy so we work together since two thousand and two. um He ran all the engineering we left and started it and you know he was feeling the pain personally as well at boomy um yeah that was sort of the inception moment of like. This this this has to exist in the world we have to do this you know.

Alejandro Cremades: So how do you guys make money at Guru? What is the business model there?

Rick Nucci: So it is a seat-based subscription. So it’s very simple pricing um and ah effectively you know it tends to be something that is um purchased and used by the entire company. So the very predictable math is you know how many employees the company has. um Sometimes they also deploy Guru to partners or BPOs or or or folks like that where knowledge sharing is really, really critical. um That’s effectively going to be the the price for Guru. So we really wanted to keep it simple and and and predictable.

Alejandro Cremades: And you’ve also raised a about $70 million. Obviously, after such a successful exit you know to a company like Dell, I’m sure that raising money wasn’t that difficult. So how did you go about it? Why did you go about it with the people that you did? And how has it been going through the cycle stool and the financing with Guru?

Rick Nucci: totally Totally, yes. i feel I feel very fortunate with the investors we have at Guru. We have um um Firstmark Capital, Emergence Capital, Thrive, um Excel. Really, really strong VC firms with really great partners that um are on our board and guide us and really great networks. Um, you know, Amis Johnny from First Mark led Guru’s Seed. He also led Boomi’s Series A. And, um, I sort of just, uh, didn’t really shop the, the, the Seed round, um, and just sort of went right back to him.

Rick Nucci: because I just had a good experience with them. I mean, we we were, you know if you think about the years of Boomi, that was during the global financial crisis. There was plenty of tumultuous times. IT spend really got hammered in 2008. Everybody got kind of freaked out and did a lot of you know pauses in spending software, a lot like we saw play out in tech in 2022, 2023. That definitely happened. And so when you can see a VC in, uh not great moments and see how they behave and show up you know for me i’m like yeah i want to i want to work with this guy again so yeah i’ve i’ve been working with him since 2008 2007 i think is probably the first time i met him um and has really been been a phenomenal partner because um you know he’s that prototypical investor that is smooth through the storms you know he’s he’s not he’s not he’s not the you know

Rick Nucci: He’s sort of the calm the calm voice through the through through the crazy things going on and I just sort of value and appreciate that um in him. um The experience of fundraising, as you suggested, at Guru was quite different because we had a great outcome at at Boomi, fundraising was just very, very different. um The other big difference was geography was a really big thing, um and now it is not really a big thing, in my opinion. and What I mean by that is, you know being in Philadelphia building a tech company um was really a weird thing to do in the early 2000s. When we got acquired by Dell, one of the articles, wire Wired covered it, and the headline of the article was something like,

Rick Nucci: Dell finds its mojo in Philadelphia? question mark like that’s the Of the whole story they can tell about the acquisition, that’s what they focus on that we’re in Philadelphia. It’s like, yeah, look, like we actually have internet. We’re not all Amish. like There is some like actual cool stuff going on in Philadelphia. Anyway, but when we were fundraising for Boomi, That was an immediate objection we had to overcome every single time. Philadelphia, you’re not in, you know, even New York wasn’t considered a viable tech hub yet in 2007, 2008. It was starting to be, right? But it was like, oh, if you’re not in the Bay Area, you’re not, you know, you’re you’re not a viable, you know, option. And we were like, that seems very flawed. So that was hard. That was a lot, you know, a lot of conversations didn’t go anywhere simply because we were in Philadelphia. Whereas with Guru,

Rick Nucci: um Geography really i would say is is ah irrelevant in our fundraising journey and like when excel let our series see. They spent a lot of time sitting us down telling us like look by the way like we funded spotify we funded atlassian we funded message bird like all these businesses that that blew up in quote unquote non tech hubs. We actually love it. you know So they had sort of this opposite bias with their growth fund. And so they actually loved that we were in Philadelphia. I think they had recently funded another Philly company, Go Puff. And so anyway, so the the GEO thing kind of went away, I think, that being a second timer went away. But yeah, over the years,

Rick Nucci: really for us the decision to raise venture capital, you know, we’ve never been a company that’s had what I’d call a, you know, alarming or or outrageous burn rate as a business, but we have always believed in the in the opportunity and ability to leverage venture capital to, you know, subsidize growth to be able to, when we saw something working, when we saw our first sign of product market fit, I think we crossed over a million in ARR in 2017. And we were like, okay, it’s time for our Series A because we sort of knew we could spend money, put money to good use and really double down on those personas we were closing and bringing in. And we sort of played played that out through the next you know several chapters of our growth.

Rick Nucci: um but But yeah, I would say I would say i feel fortunate in working with a solid group of investors. Again, you hear a lot of horror stories and I think for us, it’s just been a really positive experience.

Alejandro Cremades: So obviously, when you bring in more investors, you know they’re backing on a vision. And we’re thinking about the vision here. you know If you were to go to sleep tonight, Rick Nucci: , and you wake up in a world where the vision of Guru was fully realized, what does that world look like?

Rick Nucci: Yeah, that world looks like you have a um a ah AI-centric you know assistant that is your you know search and research partner in order to do your work, that there is nothing going on at the company that you cannot instantly access and find. And the work to do the work part of your job goes from chore and pain and daily grind down to This is energizing because I’m focusing on the work I was actually hired to do. And and we believe that um AI, ah generative AI in particular, and and where LLMs are going will allow us to drastically transform how that problem gets solved. And so that that is the that is the world. like

Rick Nucci: everyone I’ve ever met that’s worked professionally has used an internet, has used a wiki. I’m not sure I’ve ever met one that said that was a great experience. And and our goal is that it it it is a joy, it is a pleasure to be able to use Guru because it’s just going to give you that answer you need, that insight you need and get you into the the the work that you’re actually trying to get done.

Alejandro Cremades: And what about, the we talk about the past with a lens of reflection. If I bring you back in time to that moment you know that you were still you know working as an employee for another company and and right that moment where you were about to make the jump with your co-founders, I would say before, right but right when you were making that jump and giving the notice, let’s say you were able to show up right there with your younger self and be able to give that younger self one piece of advice for launching a business. What would that be and why, given what you don’t know now?

Rick Nucci: um Investing in self awareness, personal coaching, um maybe maybe that could be ah CBT, cognitive behavioral therapy, whatever you want to call it. Any playbook, any founder advice, anything about product market fit, anything about you know ah MVP thinking, all that stuff comes way lower in the list to me than the emotional durability that can be learned and gained. um Maybe it’s meditation for some, whatever whatever the thing is.

Rick Nucci: It is the hardest thing I’ve ever pursued in my life to start a business. It is um immensely gratifying. It is immensely stressful and at times immensely frustrating. And so um it is all about EQ and not only for myself, but I would also tell myself it matters for me and anybody I’m hiring, certainly the leadership team I want to build out. EQ’s got to be top of the list because how they show up is going to go straight down into the teams that they’re building and I can’t tell you the amount of times when we have had the emotional resilience and the awareness as a team to be able to endure really hard moments

Rick Nucci: is mind blowing to me. And when I see the way this team shows up and handles hard things or bad news or good things or stressful things, they are an even keel steady team that really doesn’t get freaked out, really doesn’t get spooked by things. And that to me is the ultimate skill of all skills because you can, you know, once you’ve got that down, And you and you are operating in that mindset, you will learn a new thing twice as fast, you will by default be open and curious, instead of being closed and critical and being open and curious sets you up to have a growth mindset to rethink about old problems in new ways I mean, you will just process everything so I would 10 out of 10.

Rick Nucci: forever, any founder in any business at any stage, I would say it is the EQ, the self-awareness, the mental resilience, the well the wellness and mental wellness and wellbeing that will be the biggest ah ROI that you could ever look for. it

Alejandro Cremades: That’s amazing, Rick Nucci. So for the people that are listening, Rick, we’d love to reach out and say hi. What is the best way for them to do so?

Rick Nucci: ah LinkedIn is where I spend most of my time from from a social perspective, so you can easily find me on on LinkedIn. Just look at Rick Nucci and I will be there and would love to say hi.

Alejandro Cremades: Amazing. Well, hey, Rick. Well, thank you so much for being on the Dealmaker show today. It has been an honor to have you with us.

Rick Nucci: ah Thank you, Alejandro. I appreciate you.

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