Waseem Daher On Selling His First Business To Oracle, His Second To Dropbox And Now Raising $160 Million To Simplify Accounting

Waseem Daher sold his first startup to Oracle and the second to Dropbox. He’s now raised millions of dollars from some incredible investors to help other founders grow their companies by handling their backend office and accounting needs. His latest startup, Pilot, has attracted funding from top-tier financiers like Akkadian Ventures, Empede Capital, Whale Rock Capital, and Jeff Bezos.

In this episode, you will learn:

• How Waseem thinks about competition
• Hiring well
• How Pilot can help your startup

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About Waseem Daher:

Waseem Daher is the CEO and co-founder of Pilot, which specializes in bookkeeping, tax, and CFO services for high-growth technology startups. He is a three-time entrepreneur with two successful exits: his first company, Ksplice, was acquired by Oracle in 2011, and his second, Zulip, was acquired by Dropbox in 2014. He has a degree in computer science from MIT.

Connect with Waseem Daher:

• Crunchbase
• LinkedIn
• Twitter

Read the Full Transcription of the Interview:

Alejandro Cremades: Righty hello everyone and welcome to the deal maker show. So I’m very excited about the founder that we have today someone that has done it multiple times you know he’s built finance scaled exited I mean you name it so many times that they I was kind of like losing already. You know the. The my head you know out of how many times he’s done it but without further ado let’s welcome our guest today Wasim the hair welcome to the show. So your parents. You know we’re from lebanon you know, obviously you know when you have immigrant immigrantparents and and and.

Waseem Daher: Thanks for having me great to be here.

Alejandro Cremades: You get that inspiration too because you see them working so hard I mean I’m an immigrant myself. So I really understand you know what? what that looks like so give us a little of a walkthrough memory lane. How was life growing up. Yeah.

Waseem Daher: Sure I mean it’s kind of as you expect which is I think in in many ways a very classic as you said, kind of raised by immigrant parents who came to this country with very little sort of story which is both of my parents were born and raised in this tiny village in the middle of Lebanon. And they and basically their relatives and friends like everyone from that village pretty much moved to the United States in the kind of 70 s or 80 s mostly in the kind of like Cleveland area and like half of them became small business owners of various kinds like bars coffee shops that kind of thing the other half became doctors. My parents were a little bit of an outlier in that way. But it’s like I was surrounded by this notion that yeah you know, really valuing hard work really valuing family. You’re really valuing community.

Alejandro Cremades: And you also were this nerdy kid in school. So so so so what got you into the whole computer thing because you ended up landing at mit later on. But um, but the computers. How did you you know, get into computers.

Waseem Daher: Oh absolutely.

Waseem Daher: That’s a good question and so you know it’s interesting. Um, my uncles I collaborated to buy the first computer for me and my brother and my sister it was like I think a Christmas gift 1 year and I was just I don’t know I was very into it like there were computer games and stuff but also just like me. It. It was an opera. It was a place where you could just explore and do stuff and I think I always liked that kind of thing like of course I was very into legos and building things like all of that I think is kind of related.

Alejandro Cremades: And then you ended up going to mit and Mit O E Z you know made a pivotal you know thing in your in your career. Not only because of the lessons learned but then also because of the network.

Waseem Daher: Absolutely I mean for our 3 startups. They mean my cofounders have done together. It’s been the same founding team basically and we all met an mit undergrad like we were all there we were studying computer science together we were in the computer club together like the the network impact. Was huge. Absolutely.

Alejandro Cremades: And for you I mean it was a a little of here and there as a software engineer you know at the beginning you know you were doing some internships I mean you explored how it would look like at Amazon at Google I okay, cupid. But. Literally right? away you went at it. You know as an entrepreneur you know with the cofounders that you made at mit. So why did you go at it like so young you know I I kind of like write right? after you know, school kind of thing.

Waseem Daher: Yeah, in some ways. So first of all, it’s that Mike one of my cofounders Jeff had developed this technology as part of his master’s thesis and he actually was quite excited about it. He said hey I think this thing really has legs I want to do a startup. Do you want to do with me and my it wasn’t an obvious decision. But I think my thinking at the time was like I want to do it eventually I’d like to do a company eventually and what is the downside to doing it now and I think my perspective was and look this is ah a luxury to be able to say this my perspective was well if this doesn’t work out. I’ll just go back to the Google or the Amazon or the whatever as you saw you know I had a bunch of these internships previously. So I sort of had confidence that if this totally failed. You know I could return to being a software engineer somewhere and so as a consequence it did not seem as risky as maybe it it might have.

Alejandro Cremades: And quite techy. What you guys were doing a case splice. What were you guys doing there.

Waseem Daher: Yeah, so we had some technology that could take software updates and install them without rebooting I’m sure you’ve seen that pop up that’s like you must reboot install new updates we had tech that could take those and kind of magically transform them so that you could apply them on the system while it was running and that’s. You know that’s not really that useful on your laptop or your phone. The idea is these server systems where the downtime is really expensive. You might have thousands and thousands of them like the target was these kind of like large scale server. It administrators.

Alejandro Cremades: And you were alluding to earlier I mean the different companies that you’ve built now 3 of them. You’ve always had the same cofounders Jeff Arnold and Jessica Mckiller so why what makes this say trio or these 3 more sketeers. You know so effective. Ah, building companies. Why are you guys? So good together.

Waseem Daher: Sure? Well at this point I think one of the reasons we’re so good together is because we have worked together a lot and so it’s sort of like you know there’s a virtuous ah you know virtuous cycle in that way here’s what I would say I think like the key elements to making it work are. Deep mutual trust and respect and actually like clear and distinct areas of ownership like we work together well because we know when we need to actually work together and we know when we need to not work together. In other words, what falls into any 1 person’s domain and like. No one’s relationship is perfect of course like obviously there’s still occasional voices raised or tears shed or drama. We occasionally still annoy the heck out of each other but it works and is productive because we know how to work well together and what that means is. We can actually focus on making the business successful as opposed to focusing on the logistics of figuring out how to work together.

Alejandro Cremades: And what about on the logistics because for example, on caselies you were there. The Ceo O and now you’re the Ceo of pilot. So how do you think that the dynamics between you guys have also shifted. To you know for you now to take the Ceo versus taking a Ceo role like you did on caseplays.

Waseem Daher: Yeah I think the title change actually has not really materially changed what it is that Jeff and I each spend time on I think if you looked at the portfolio of what were we each doing a k splice what we’re each doing at Zulla. What are we each doing at pilot. It’s actually probably pretty similar to how it used to be in the sense that I do think. For the really big strategic and important decisions of the company. They are really made by Jeff Jessica and me together and I I think there’s there’s something interesting about that which is if we don’t all agree I’m not saying we run the company by consensus, we don’t but if we don’t all agree. But look. They’re smart talented people probably what that suggests is maybe there’s something they see that I don’t maybe we should talk it through a little bit more It’s a good prompt to say let’s spend a little more time together on this and if we still don’t agree and the decision has to be made well look I’m the Ceo I will make the decision. But as I think a healthy prompt for. Well maybe there’s more here than you might you might initially think.

Alejandro Cremades: And how do you get to that point of trust.

Waseem Daher: Well I think you just got to put in the hours right? It’s like the the reason it works for us is we were all friends together at mit we were all you know we we’re a bunch of classes. We’d work together on Stuff. We’d worked on projects together. But I think the the place where that deep trust was forged was that that first company which is. Actually just doing it together and experiencing the highs and the lows and the pains and the joys.

Alejandro Cremades: So would you say that after this experience of now having built 3 companies with them team versus idea what are your thoughts. So.

Waseem Daher: Strongly strongly team and just to make the point even more explicit for both the second company and for the third company like when we left oracle we were like we want to do another company together. We all got together and we said okay, what are we going to do and same for the third company and the point is. For each of us was like we know this is a good team. We want to work together with this team I want to work with smart talented people who are going to challenge me to do good work where I feel like I’ve got a great dynamic and what we do matters but it actually matters a lot less than the team I would work on basically anything with this team.

Alejandro Cremades: So then let’s talk about case place. Let’s let’s go back to so to case place. How did you guys capitalize the business and how was that process to getting it all the way to the acquisition which was acquired by oracle hey first company first exit. Not bad.

Waseem Daher: Sure.

Waseem Daher: Yeah, not too bad at all. So the case by story is a very interesting one because there’s sort of a combination of things that enabled it we bootstrapped it. We did not raise any venture capital for the business but we got we did a couple things sort of nontraditionally to finance it one is we won a cup. Couple of business playing competitions. Actually there was one at mit called the mit one hundred k competition which we won we’ had entered the business in the early days and then we got a grant from the Us government from the national science foundation. There’s thing called an Nsf sbir grant so through the combination of like a little bit of grant money. A little bit of just initial capital from that business plan competition and then we just had a product. We sold to people now. It also helped by the way that we kept our expense rates super low and that we were all you know, 22 and eating ramen and living together in a like kind of crappy apartment in Cambridge. So our expenses were low. We kind of had that initial capital and then we just worked very aggressively to get a product into the hands of our customers that generated revenue for us so we we bootstrapped it and I think importantly, that led to I think a very very healthy appreciation for basically the value of the dollar and like. Hey you actually have to build the business with sustainable economics was a lesson that was deeply ingrained in us in that first venture.

Alejandro Cremades: So let’s talk about the acquisition. How did the acquisition you know happen with with oracle.

Waseem Daher: It’s it’s interesting because to this day I feel like I still don’t really understand and here’s what I mean by that one of the things that I think is a bit of a misconception is I think many founders or entrepreneurs believe that like oh. 1 day I wake up I decide I want to sell my business and I like go out there and I look for buyers and I’m not saying that that isn’t possible but that’s probably not going to get you outcomes that you’re particularly excited about because to really get an outcome that’s going to be. Interesting for you and for the acquirer there kind of has to be the strategic alignment. It’s like why strategically does this company benefit from having what we do in in the case of Oracle I think like you know, 2 years prior we had met with them and we talked to them about hey this is our. Capability. We could do this rebootless. Update thing on Linux we think it could be of of real interest to your enterprise customers and then we like just didn’t hear anything for a while like a long time like years and then just one day kind of out of the blue they sort of got in touch with us and I think the thing that was puzzling to me was like. Why why on that particular day did they choose to reach out what actually was the catalyst and the inputs that are very complicated right? It’s like what else is going on with the company. There are other strategic priorities. The mood of any given person at a given day. It’s like there’s a lot of serendipity that goes into this stuff and I think.

Waseem Daher: The only thing you can really do I think to sort of maximize the probability of a good acquisition outcome is a little bit paradoxical which is don’t build towards acquisition build a thing that your customers actually want and want to give you money for. Grow The customer race demonstrate that it’s valuable and then potential acquirers end up seeing that.

Alejandro Cremades: And I was he ended up being in the 7 figures. So quite a good outcome for for everyone. So you guys were there for about a year a little bit over a year doing you know what? it’s called a vesting and resting ah maybe not so much resting. But I’m sure that.

Waseem Daher: Ah, sir.

Alejandro Cremades: You know there was a point you know in time where you know the 3 more sketeers you know, got back together. You know, thinking about another problem that they were excited about and you know, bringing that solution to cover that problem and Ita eventually became sulip you know which was the next company I mean how did you guys time that I mean. Did you guys like count to 3 and they gave your notice at the same time at oracle how did that happen? Okay, nice.

Waseem Daher: So first of all, I was an 8 figure exit. Not not that the details really matter. But yes, exactly what you said which is basically a year and a day after the oracle acquisition we sort of knew we still wanted to do another startup. We wanted to get the band back together. It’s basically exactly as you described which is we make clear to the team. It’s not like one day we surprise them we sort of make clear to the team listen we think Oracle is a great company. We’re glad you’re excited about this technology we are committed to making this transition successful. But I want to just be clear. This is not going to be the long term home for the founders. We intend to go and do something new.

Alejandro Cremades: So then at what point do you realize that that’s something new. You know is knocking and it’s time to get going.

Waseem Daher: I think for us we sort of had this idea that we thought a year would be a good amount of time to kind of transition over the tech and there were of course some incentives to remain for a year but we sort of basically a year and a day we all got together. Like in 1 of our apartments and said okay, what’s the next thing going to be how do we get started on it.

Alejandro Cremades: So give us ah a little of an insider view on that you know what happened in that apartment get together.

Waseem Daher: I think the question was okay, what problems do we have that we think need to be solved where we think we are good potential solvers for those problems or maybe here’s a more structured framework I think for every business I think for a successful business. You need a couple of key elements element number 1 is you need a large market size. You need to be solving a problem that is big and painful. So that when you succeed you have actually potentially built you know a billion dollar or multibillion dollar customer or multibillion dollar business so you need to Target. Kind of a big media opportunity. So the importance of the market size is key the second kind of question is like why now meaning what has changed about the world to enable this company to exist like probably again the scarce resources not the idea lots of people have great ideas. Why doesn’t this company already exist. What has changed about the world that makes this the time and place for this business and then the third question is why this team why is this team uniquely going to be able to execute on this particular problem and that that’s kind of the framework that we used. I don’t know that we had it so explicitly nailed when we were thinking about the second business but certainly by the time that we were thinking about the third business that was kind of the framework we had to say fine. How do we evaluate the caliber of any idea which is market size. Why now why? us.

Waseem Daher: And and basically like how hard is it going to be or what? what’s the easiest way to really test that the market is interested in this particular thing.

Alejandro Cremades: So tell us then about sulip. So then you guys you know land on the idea of sulip. So what was the business model there and how you guys make money.

Waseem Daher: Sure so the insight on zulip um, which I think was was spot on I think I have some comments in our execution. But I think the insight was spot on at the time this was I think like August Twenty twelve and the insight was listen. The. The group chat experience at work is actually pretty awful and in many ways it has dramatically lagged behind what consumers were used to in their personal lives like in your personal life. You know August 2012 you had the iphone or the Android phone like you had pretty robust kind of 1 on one and group messaging but at work you were still using like I don’t know this like almost like early two thousand s late 90 s like chat technology. And it was 1 on 1 base. There was not really robust group chat your options were sort of like I Rc which was kind of the domain of you know nerds like us or basically like a jabber server. It was like the the state of the world was very clearly going to look different in the future than it did in the present. And that became clear to us because again we had sort of played around with this stuff ourselves. We said we think we can build the solution that will actually you know make make workplace chat at work a lot more robust and a lot better and I think if you look at the success of slack as a business. They really really did a solid job of executing on.

Waseem Daher: Kind of that insight or that thesis.

Alejandro Cremades: But this company I mean it was a it didn’t take that long. It took get a choir I mean we’re talking not even about not even 2 years before the acquisition materialized with Dropbox. In this case I mean you guys had some liquidity you know from the previous acquisition from. From oracle from case plus so how do you go about financing the operation.

Waseem Daher: So with this company. It was ah with sulip. It was much more kind of on the traditional venture capital path meaning we had raised a bunch of money from angel investors kind of right out of the gate I think it was like one point five one point six million something like that and basically we called up. Essentially investors and advisors who we connected within our first venture and we say you know we’re getting at it again. We’re going to do another company with this founding team. Are you interested in getting on board. So we raise a fairly substantial at the time um angel round and the plan was to go raise a venture series a and all that other stuff and. While we were kind of in market exploring the series a options. The Dropbox offer kind of came on the table and was very interesting. You know again, it’s like these these things are so driven by things that are broadly out of your control. So in the case of Dropbox specifically like.

Alejandro Cremades: So how did that offer come on the table. Yeah.

Waseem Daher: Drew and Arash the founders were mit alums and I knew Drew specifically for my time at mit and so he was aware of actually what we had been doing with case Splys he had followed along with that journey. He was familiar with the tech. He’s familiar with the caliber of the team and so one is that he personally kind of like knew and could vouch for the team being great. And 2 was that it was very aligned with kind of Dropbox’s strategic priorities at the time where the view at the time was look We’re really good at the kind of file sync file sharing thing but we want to sort of do more at work. We want to not just be about files. We also want to be ah. About communication about collaboration about collaborative editing and so there’s a bunch of other stuff. The Dropbox was doing at the time that that the kind of concept of like a group chat at work sort of folded into that very nicely.

Alejandro Cremades: So then here you go again, you know second company second exit how many figures are we talking about my god got to respect the 8 figures now in this case for you guys you know again, you know you pass the 2 year Mark you know that vesting.

Waseem Daher: Sure this again, a kind of 8 figure outcome.

Alejandro Cremades: Um, a period and then the 3 of you you know again, got together on the apartment. You know to discuss about market to discuss about the why now and then you arrive on your latest baby which is pilot now with pilot. You guys have been added.

Waseem Daher: Yes, that’s true.

Alejandro Cremades: For over six years which is like in dog years especially you know the startup live and and given your previous you know experiences with caselies and and with with sulip. You know, obviously it’s it’s the longest you’ve ever been at a company pushing things together. So why.

Waseem Daher: Yes.

Waseem Daher: Sure so pilot was motivated by pain. We felt very viscerally and very directly in our previous ventures. So first maybe 2 seconds about what pilot is we do accounting tax prep fractional cfo work.

Alejandro Cremades: Pilot.

Waseem Daher: Principally actually for high-growth startups. But for other companies. So. In other words, you hire us and we do your accounting for you and the way that we do it is we employ a bunch of accountants who are full-time employees of ours who sit in our office who do the accounting. And then we’re kind of building the iron man suit for them under the hood. We have an engineering team that builds a bunch of software that we use internally to do the work more accurately more reliably more consistently and and the way we got here is that this was a huge paint point for us in our previous ventures in two ways. Pain number one was again remember the first company we bootstrapped so we had no money and so having no money I think sometimes causes us to make good decisions and sometimes cause us to make bad decisions. One of the bad decisions we made in the first company was not to hire an external accounting firm. It was I bought a copy of Quickbooks and I was like I’m pretty good at math. I’m just going to figure this out and so as I was doing the bookkeeping again along with my co-founders and other and other folks of the company I think 2 things became very clear thing number 1 is wow this is tricky you you really do want the help of experts to get this right? but insight number 2 was There’s also a lot here that is really mechanical and tedious that the computer should be doing like we should be writing software to help do the work and the reason to have the software do the work is not because it makes it more efficient. It actually makes it more accurate and so those 2 ideas together are ultimately what form pilot it’s.

Waseem Daher: Computer can help out a lot here. But also I don’t want to buy accounting software. What I want is a partner who can actually solve the problem for me and that’s a little bit like that’s a little bit of a strange shape for a technology company. Probably the average. Technology founder would have said I’m going to make an accounting software package that you buy and you use yourself and we said no we want to solve the whole problem. We Want to be the accountant for the company because that’s what we wanted ourselves in the previous ventures I didn’t need another piece of accounting software I needed like a trusted expert. Who effectively could be on my team.

Alejandro Cremades: I mean and and in this case, How do you guys make money.

Waseem Daher: Well, it’s very straightforward. It’s a subscription. You come to us, you pay us monthly or annually to help out with the accounting with the tax prep with the cfo services and the same you hire us basically instead of hiring the firm down the street that you might have worked with.

Alejandro Cremades: And why would you say especially now that you’re on your third rodeo. Why is it so important to be laser focused on the customer.

Waseem Daher: Well so this is something I feel really strongly about which is as a founder you kind of have 1 job in a way you have to make a thing that people want that they’ll pay you for and that they’ll tell their friends about and. If. You’re not doing that it sort of doesn’t matter what else you do it doesn’t matter if you’re exceptional at everything else, but you fall short at that particular objective. The business will not be successful and so I think that’s really clarifying. It’s tempting to spend a bunch of time worrying about what are my competitors doing or. You know what how should my office look or how should we think about this you know decision Abc it’s like if it’s not ultimately in service of building a thing that your customers love and want to pay you money for like don’t waste your time on it.

Alejandro Cremades: And also while you’re being laser on the focus and and and really focused on the customer. How do you go about not getting too much in the weeds.

Waseem Daher: Sure So I actually I would say almost the opposite I Love to get in the weeds I think you should get in the weeds and the reason yet it’s a little bit counterintuitive I think a lot of people think like oh you’re building a thing at at significant scale like.

Alejandro Cremades: Why why? why? go ahead.

Waseem Daher: Surely, you should just build a process and like let the process run and that would be true if you were one ah hundred percent sure that you were building a process around a thing that was correct and I think the thing that I’ve seen time and time again in startups is. You have an imperfect view of the world. You have an imperfect view of the world formed by what you’re hearing from your customers from your prospects just like from what you’re what you’re hearing from other folks and over time that view is refined and the way that that view is refined is by getting exposure to almost to more data. And the problem with kind of like trying to build it into a scalable thing all at once is you are removing yourself from kind of that additional learning about the world that impacts how you think about what your customers want or don’t want and so I’d encourage folks to be overly scrappy to overly get in the weeds. Rather than to try to build the perfect process from day one and let it run.

Alejandro Cremades: And as you’re building the perfect process or the perfect company. How do you think about competition to.

Waseem Daher: Yeah, so this is a this kind of goes back to my first point about if it’s not in service of making the customer experience better. You shouldn’t be doing it and the danger with competition or with like thinking too much about your competition is your competition actually does not really matter. And here’s here’s why I say that in almost every business again almost every business not universally true. It is very rare that there is truly a market dominating winner take all like even in categories that you think. Have obvious leaders like for crm salesforce is like the obvious name there. Salesforce’s market share is like 30 but twenty thirty percent that’s that’s a lot but it is not 50 or 70 or 90% like there is a robust system of of other providers that do this stuff and so it’s. If. The market is not winner-take-all you should care less about what other people are doing. You should care more about what your customers are saying if your customers are happy and they’re giving you money and they’re referring other people to you and they’re promoting you your business will be successful independent to what anyone else does and if your customers are not happy and they’re not promoting you. Doesn’t matter what your competition is doing your business will not be successful and so the danger about spending a lot of time thinking about competitors is if it if it is done instead of spending that time talking to your customers I think that’s a big miss.

Alejandro Cremades: And just for the for the people that are listening to in this case I mean you did finance capitalize very well the operation. Um, how much capital have you guys raised today.

Waseem Daher: Yeah, we raised about $160,000,000 from Sequoia Stripe Jeff Bezos and a bunch of other great folks.

Alejandro Cremades: I mean a bunch of other amazing folks I mean you have hoard Luman from yext. He actually was on the podcast. They very recently Adam D’angelo the founder of Quora Drew the founder of Dropbox we have a paul english founder of kayak.

Waseem Daher: Nice.

Alejandro Cremades: I mean and I could keep going on and on and on with all these like absolute rock stars that you have in how how the hell did you land this people.

Waseem Daher: It’s a good list. Well again, it’s like this is this has been our sort of whole career in the making it’s like these are folks that we encountered either through the mit connections. Through the case place connections through the oracle connections through the zob connections through the Dropbox connection. It’s like over time just like folks that have been in our network that have been excited about what we’re up to and who wanted to kind of come along for the journey on on this third one

Alejandro Cremades: And what does that process of activating your network. What does that look like especially for the people that are listening that are wondering hey you know I’ve gone to great schools I built some great people that I have access to how how do you go about activating that.

Waseem Daher: It’s a good question and I think it requires like some real authenticity meaning the way that we cultivate these relationships was not like oh there’s a task on my to do list to like go network. It’s. Really just sincerely like keeping folks up-to date on what’s happening with you and your business asking them for help when and asking them for help when you need it and I think that that’s a little bit counterintuitive in the sense that like the the thing that’s so exciting to me about so many of those investors are. These are folks that I would pay money to get advice from and so the prospect of being able to get advice from them and being able to get funds from them is like very very interesting and that is only possible because we’ve sort of cultivated this relationship with them over in some case literally decades.

Alejandro Cremades: Now obviously you guys have been at it for about 6 years so if you were to go to sleep tonight and you wake up in a world where the vision of pilot is fully realized what does that world look like.

Waseem Daher: So The the basic I think desire sort for what are we up to ultimately I think the the mission and the mandate is pilot is your trusted partner who runs your back office for you which causes your business to be more successful and the like fundamental problem we’re trying to solve is. Everyone in the world who starts a business of any kind whether it’s a tech company or a coffee shop or a doctor’s office or whatever it is they start it because there’s something they’re trying to do in the world. There’s a product they’re trying to make or a service they’re trying to provide and they’re excited to commit their energy towards causing that to occur. And so they get started. They start their company or they you know they have the company up and running and what they soon realize is there is way way way way way more to running your business than just providing that product or service. There is all of this back-office stuff and the backoffice stuff is like particularly tricky because one it’s. Really important and the reason you can tell it’s important is because big companies have entire teams devoted to running these operations well and two is it’s rarely the area of expertise of the business owner and so really I think like what is pilot look like in the limit if we’re super Successful. It’s. We should be doing all of this stuff for you. We should be doing it better more reliably more accurately more scalably certainly than you could do yourself or than anyone else can do it and the consequence of that is your business should be more successful like if we could give you.

Waseem Daher: Finance team and the legal team and the recruiting team and the it team and the real estate team like we give you the powers that like a fortune 500 company has in these departments but we could use it to turbocharge your small business somewhere like surely that would make your business more successful. And I think that’s ultimately what we’re looking to do. We’re kind of like trying to democratize the capabilities that these huge companies have and we’re trying to bring them to the average business. That’s out there starting with the accounting or starting with the financial back office but certainly that’s not the limit of the ambition.

Alejandro Cremades: And definitely you guys have been. You know? Well you have been well on your way there because you’ve been growing like crazy I mean just on the employee count in the last year alone according to Linkedin insights. We’re talking about over thirty two percent on the employee count. So. How do you go about adding people so fast without breaking things on the culture.

Waseem Daher: I mean it’s hard. It’s hard and I think it is ultimately requires you to lean very heavily on our robust hiring and onboarding process which is like first of all, you have to understand what the roles you’re trying to hire are you have to really crisply understand like. What is it that we’re trying to do with this role and what does success look like and then you need to build an interview process that actually tests for that and I think that sounds obvious but people don’t really do it people like these kind of like gimmicky gotcha interview questions or like well would I be friends with this person like that’s actually not the question the question is are they going to excel in this role so you have to design an interview process that really probes deeply on all of the things you think are needed for success in the role and can actually like form good decisions in a really principled you know way that minimizes bias that actually. Sets you and the potential employee up for success if you bring them on board.

Alejandro Cremades: Now we were talking about the future earlier. So let’s talk about the past but let’s do that You know with the lens of of reflection here imagine if I was to put you into a time machine and I’m able to take you back in time.

Waseem Daher: Sure.

Alejandro Cremades: Back in time you know to that moment where you were still at mit you know, maybe at that point where you were you know, getting together with Jessica with Jeff he was the 3 of you guys. You know, starting to ah brainstorm about a future a future where you could do something together. Build a company of your own. If you could enter that room and be able to look at the 3 of you the younger selves and be able to give 1 piece of advice before launching a business now that you are on company number 3 exactly with the same co-founders. What would you tell your younger self. You know. Obviously and also Jeff and and Jessica if the 3 of them were to listen because typically our younger selves. You know they they don’t listen that much. But let’s say they were actually listening.

Waseem Daher: Sure I think probably you know, interestingly the first company we kind of almost stumbled into by accident which is again it was kind of Jeff’s master’s thesis we’re like the tech is cool but like we didn’t know anything about how to run a business or how to evaluate a business or so probably I would leave the team with. Kind of framework we discussed which is being really thoughtful about market size being really thoughtful about why now being really thoughtful about why us and that really laser laser focus on staying extremely close to the customer to make sure you’re really validating. You what you? what? you ultimately have is a hypothesis about the world. You think the world behaves in a certain way and your job is to kind of prove or disprove that hypothesis and the way that you do that is you kind of have to really test it in the field you have to talk to the customer you have to make sure they’re excited like there’s no substitute for that kind of like. Proximity or closeness.

Alejandro Cremades: I Love that now for the people that are listening. What is the best way for them to reach out and say hi.

Waseem Daher: Great question, a kind of bunch of options. Um, certainly email is always good I’m just wasim at pilot.com you can also find my substack. It’s wasimm dot substack dot com and I’m at withsim on Twitter as well. And then on Linkedin I’m just Linkedin Slash in /wdother so any any of those would be great and then pilot is at pilot.com we’d love for you to check us out there.

Alejandro Cremades: Amazing, well amazing. Well was him. Thank you so so much for being on the deal maker show today. It has been an honor to have you with us.

Waseem Daher: Thanks for having me this is it was great I loved it.

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