May 19, 2023

Episode 275: Jim Dries, Founder & CEO of

Jim Dries is the founder and CEO of, a provider of AI technologies for revenue professionals primarily in sports, entertainment, and university fundraising. empowers its users to effectively leverage the mountains of customer data their organizations generate to drive efficiencies that improve revenues without increasing costs. The vision at PILYTIX, is simple, as Jim shares, “We want to help organizations exceed their revenue targets by working smarter.”

Prior to founding, Jim’s career spanned leadership roles in finance, product development, sales, and marketing. Jim is a graduate of Yale University and the University of Chicago Booth School of Business.

Julian:Hey everyone. Thank you so much for joining the Behind Company Lines podcast.Today we have Jim Dries. Founder and CEO of PILYTIX, a provider of AItechnologies for revenue professionals, primarily in sports, entertainment anduniversity fundraising. Jim, I'm so excited to have you on the show today. Notonly because we haven't really had founders who you work within the spaces youdo sports, entertainment, and university, and offer, really .

Interestingtechnology solution for, something that they've been doing.

Time and timeagain, I'm sure that there's probably some standardization done, within theindustry, but you, you don't really think about these. Industries as, asparticularly, technologically innovative. So I'm really exciting on what notonly you're doing for these industries and, and, and what you're enabling themto do, but what does it mean for the entire industries overall and thetechnologies that they're incorporating.

But before we getinto all that, what were you doing before you started the company?  

Jim:If you, if you look at, I think most founder journeys, I've probably taken theroad less traveled in a lot of respects. So, right out of undergrad I got intoinvestment banking, not because I had any passion or enthusiasm for investmentbanking, but.

They paid prettywell. Yeah. And graduated college with some debt, so, gotta go make some moneyand kind of Sure. You just fell into that. And I, I did that for like four anda half years and I honestly hated every waking minute of it. But it was apretty good education, right? You, you, you learn a lot.

I, I learned morelike in my first week doing that than I did. In undergrad and any other sort ofwork experience before that. And then, by the time I sort of figured it out wastotally ready for something else, didn't know what I wanted to do. And I wentto a company at the time it was called Corporate Executive Board.

They've since beenacquired by Gartner, but got sort of involved with the world of sales andmarketing. Yeah, I was totally unqualified to, to be hired for that, but I wasjust really fascinated by the company and and, and it was, it was just fun,doing something that was new every day, learning, being in a sort of acollaborative environment.

To this day thereare people that I call on from that organization and then Did that for five-ishyears and then got into sort of, sort of parlayed that experience and that kindof skillset that I was building. Yeah. And got into a tech company, a small-ishtech company. And I was responsible for launching a new product there.

And then I ended upleading sales and marketing. And over that time we took the company from, acouple million dollars top line up to almost 15 when I left. Yeah. And you knowwhat I, what I kind of, as I was going through that, I was, I was kind ofalways looking ahead, what was I gonna be doing next?

Didn't really know.Yeah. But I was just like noticing. Challenges that I had at my last, at thetech company as well as the previous experience. Like where are their sort ofproduct areas. I, I, I did fall in love with product development when I wasmm-hmm. Working at the tech company and, is, is that was job was winding downsort of.

Came to a placewhere I said, it's now or never. I've always kind of had that thought, maybeI'll be an entrepreneur one day. Yeah. But never really had like the idea thatI was so passionate about that I had to do it. Yeah. And, and ultimately whatthis company became, was sort of grown out of that passion of like, yeah, andthis gets into this company now, but sort of.

How, how do we sortof get all the clutter out of the sales and marketing process so we can reallyunderstand Sure. Like where deals are and where should we be focusing our time?Yeah, because what I, what I had found, like salespeople, and any revenuecapacity, they're, they're human beings, right?

And we, we all getlike tunnel vision. We all have biases, tendencies, whatever you want to callit, where like, you'll spend so much time doing one thing. Yeah. And focusedand you, you're, you're sure of the outcome and then it doesn't happen. Yeah.Why? Yeah. Right. And wouldn't it be nice to know that we are spending time inthe wrong places earlier before we like spun our wheels and, and wasted sometime?

Yeah. So, yeah,that, that's what I was doing. And, and kind of the, the, the journey to, to,to starting this.  

Julian:Yeah, it's so fascinating. Thinking about, obviously you wanna jump intoPILYTIX in a moment, but it's fascinating to think about the transition fromthe sales you were doing into software sales. And I'm curious, who were thekind of the, the, the buyers that you were talking to previously before youwent into software sales, and what would you kind of define as something that'suniquely different about selling between different industries that, is, is anadjustment that most people have to make, whether it's coming from one to theother or, or vice versa.

Jim:Well, so, I, I was, I was really fortunate in that, I, I got to work with hugepublicly traded companies. I think at one point we were working with like 80%of the Fortune 500. Wow. And, and, and selling solutions to salespeople. And asit turns out, like, You've gotta be on your game and you've gotta be sharp.

Yeah. And you'vegotta be able to listen. And Bali knowing I don't know if I can say this on, onthis, but like, I'll say it this way. You say, say whatever you want. Bs A Bs.You, you can't bs a BSer. Right. And so, what I learned is, the process of, of,of selling is really not about, Talking about how great products are, it'sreally understanding what challenges are, what, what it's a cliche, but youknow, what are those things that are keeping people up at night when they'rethinking about how to get their job done effectively?

And so, for me thatwas just like the greatest learning experience. Yeah. And then translating thatinto software sales. I'll, I'll, I'll tell you Julian, there wasn't. It, itit's really if you learn sort of the art of listening and Sure. Not just, and,and waiting pe for people to finish their thoughts and making sure that you'reallowing them to express themselves thoroughly.

I, I, I really lookmore at, at, at sales and again, this is now the third company where I'minvolved in sales to some degree, but start by listening. Right? Yeah. And,and, People will tell you what their challenges are as as long as you're askingthe right questions.  

Julian:Yeah. And what do you think it's in terms of what's important?

If I'm thinkingabout, as a founder, maybe I'm leading my sales motion initially before I evenhire sales individuals and their sales team. What, what, what do I need toincorporate into my process to really identify how to build that structure? Ito understand my process? Is it asking the right questions?

Is it under,getting customer feedback? Is it finding new ways to just identify moreinformation? Or is it learning more about your industry? What in particularhave you found that founders should kind of. Preliminarily pay more attentionto as they're gaining and building their sales motion before they start,investing in, in their team.

Jim:Yeah. I, I, and, and, and that's, our first handful of clients were soldentirely by me and probably talked to a hundred businesses before we evensniffed our first sale. Yeah. I, I, I think. In the earliest days, you've gotto be crystal clear on the vision, right? Yeah. Because I, I don't care whatcompany it is, the product will be better a year and two years, three years,four years.

And we went out tothe market with, with a pretty good product. Yeah. But it was nowhere near sortof the level of, of depth and certainly hadn't been informed by any userfeedback at that point. And so really kind of. Making sure that we're clearwhen we're talking to prospective clients about the vision, making sure that,the vision does something for them.

Right. And itdoesn't, it makes no difference whatsoever. If your vision doesn't line withtheir problems, you can have a nice conversation, but don't kid yourself thatlike, this is where you should be focusing your sales efforts. Yeah. So I,yeah, I, I, I think, I think as long as, you're asking questions that figureout is this somebody that you know ultimately is going to be a good partner forus and sort of grow their organization into whatever product we're selling?

Yeah. Yeah. I thinkthat's where you have to start.  

Julian:Yeah. Yeah. And you thinking about, those conversations a little bit more,where in the sales process do you find most companies having a challenge of, offinding that insight? I think about, our sales funnel at my company, and, andwe know that if we are, lacking in open rates, for instance, just talk aboutemail outreach, we're, if we're lacking open rates, we need a better subjectline.

If people aren'tclicking and, and having a call to action, we need to have better messaging orshorter messaging, or more concise, more branding. And then if, there's so manymeasurements that I think help us signal where we need to improve, but I thinkthere's always, areas that we're missing probably.

And what have youseen most founders or organizations, not consider in terms of the sales processthat ends up being more of an issue later on? That they're just unawareof?  

Jim:Yeah. And when, when I started this company, I probably didn't think in thoseterms. Sure. For better or for worse.

But, but, but I, Iwill tell you, at some point during every sales process, somebody's gonna wantsome proof of life, right? They're gonna want, sure. They're gonna want someevidence that this is gonna work for them. And, very often that involvestalking to another client. I think one of the things that we, yeah.

Did, and we, wemade like, and, and, and I won't bring everybody into the, i'll, I'll say Imade a million mistakes and especially in the early days of, of the company,but if we did anything really, really well, it was sort of really putting thosefirst 2, 3, 4 clients in a bear hug. Yeah. Making sure that they were using theproduct, making sure that they understood it and, and effectively sort of,Accelerating their ability to advocate for us.

Um mm-hmm. Becauselike at, at, at the end of the day, we can talk about how great we are all day,every day and sure we can get people involved in the vision, but at some pointpeople are going to want to see Yeah. Evidence and they're going to look tosomebody who's sitting in, in the same seat that they are.

Right? Yeah. Theyknow that I've got a vested interest when I walk into any sort of. Salesmeeting people know that I have a vested interest in selling them a product andtaking their money. Right, right. I mean, that's, it's, it's commerce andthere's nothing inherently dirty about it. But given the incentive structures,like they want to know that this is going to work for them.

And so I think oneof the things that we did really well was making sure that. Our clients, werein a position to, to sort of tell our story on our behalf, just based on, onthe successes that they've, they've had with it. So, yeah.  

Julian:Yeah, yeah. Well said. And thinking, moving into, politics and, and what you'vebeen able to do, describe, what in particular did you see in these industriesthat I don't think a lot of people consider, university sports, entertainment,what was the previous incumbent of their sales process and.

What did you, whatgot you into these industries in particular, and, what, what problem were, areyou solving right now?  

Jim:I, I wish I could like tell you, Julian, that this was like the vision, thestrategy when we started and, and it wasn't very candidly. And, and I'll, I'llkind of walk through the journey of how we ended up, where we ended up.

Yeah. But when,when, when I started and I, I, I mentioned before, like made a millionmistakes. Yeah. And one of like the common entre, and I didn't know this at thetime, but turns out it's a pretty common entrepreneurial mistake where you lookat sort of your product, you think about the vision, you say, yeah, like whatwe've built and what we're building.

Has applicabilitylike universally to any in, in, at the time we were looking like any B2B salesorganization needs our product. And, and, and therefore we went out to like theentire universe. Right? Yeah. And. Unfortunately, we actually had some successwith that. We kind of, for, for the first couple of years were, were spread in,in a whole bunch of different sort of industries, company sizes.

There was like noconsistency. And then without sort of the, the full journey of how it happened,we, we kind of accidentally fell into the world of professional sports. To yourpoint, I didn't know they had sales organizations like, yeah, forgive theforget the decides going by. No. But I didn't know pro sports teams had likelegitimate sales organizations and sales operations didn't know that.

Like I've gone toplenty of sporting events Yeah. And got my tickets at the box office or a boxoffice or on, one of the secondary markets like StubHub, these types of places.And when we got into sports, the Sacramento Kings were our first pro sportsclient. And we had a sales rep on the West coast who's like, Hey, I'm going up.

I got a meetingwith the Sacramento Kings. I was absolutely convinced that he was just usinglike company resources to go watch a basketball game. And, and, and I, I, Ireally challenged him and he's like, no, no, he is like, they've got 40 people,they're selling products ranging from a, a couple thousand dollars all the wayup into the 6, 6, 7 figures.

Wow. Yeah. They'vegot, various sales cycles. They're using They, they've got abunch of other tools. Wow. Like this, this looks like a good fit. And I'm like,okay, you go do that visit, but I think you're wasting your time. Sure. And acouple weeks later we get a contract. The reason we, we stayed in that industryand, and are, are still very active in this industry is because and I didn'tknow this at the time, but lots and lots of folks want to get into that space.

Like they look atsports, they look at entertainment, they, they, they think it's got some sexappeal to it, and they want to be around it and they want to, and, and at theend of the day, We're supporting the revenue professionals, yeah. They'resurrounded by four walls and a screen and, it's like they're, they'refundamentally not different than any other Yeah.

Sales organization.But the beauty of, of pro sports for us is that pro sports, we, as, as sportsfans, we can look at them and the teams and think, oh, they're, they'recompetitive. They don't compete for, for business, they don't compete formarket share because they're all in different markets.

Yeah. And so whenyou do right by one of them, they will tell their, friends and neighbors, so tospeak, the folks around the leagues that they're in that we're, we're doinggood work for them. And that's really kind of how we got our first five, six,before we did any marketing in that space.

It was just purelyword of mouth. Yeah. And then pro sports took us into university sports. So I'min Austin university of Texas. We just, we got in with their senior associatead who's coincidentally she's now working here at PILYTIX as our VP ofmarketing. But at the time, we, we had this hypothesis, like the large schoolsare selling very similarly to the, the, the pro sports yeah.

Organizations thatwe were working with. And so we, through the University of Texas, we got intocollege sports, same type of business, but we were there for maybe a couple ofweeks before people at Texas started coming, coming to us, saying, Hey, Can weapply sort of the same tools that you all are using to help us fill thestadium?

Can we use that toidentify new donors to help our Yeah. Our gift officers sort of acceleratetheir processes, that type of thing. And and and sort of a, a buddingfundraising business was grown.  

Julian:Yeah, and, and describe what, what the what the technology allows them to do.What kind of insights are you gaining as a sales team?

Just to paint thepicture a little bit more, I've, I'm a user, I've been doing this process. Ifinally get this new tool, PILYTIX, and then what am I enabled to do? What is,how, how is my effectiveness, increase because of the, the n new tool?  

Jim:Yeah, that's, that's a great question. So, We've taken the approach of takingvery sort of specific elements of the sales process and building tools aroundthem because, I think there's a lot of tools that, that, especially in thiscall it sales enablement space where people sort of have packaged their toolsas like the be all, end all.

Like, yeah, buythis product and your sales are gonna grow up. We take a very granular approachand the granular approach goes like this. We start at the top of the funnel,right? How do you identify your best leads? And we are operating in spaces andthink about it, sports buyers yeah. Or, or, or donors to a university.

There's a lot ofpeople who are able to write checks to mm-hmm. Either buy those products ormake those donations. How many of them are interested, right? And historicallywhat these industries have done is they've just like smiled and dialed. They'vegone through these huge long lists and just called, and called and called andemailed and, and all of this.

And our wholeapproach is how can we sort of enable them to work smarter, not harder. So westart at the top of the funnel, figuring out if you've got a contact databasewith a half a million or a million people in there. Most of them are not goingto buy, most of them are not going to write a donation check.

Right. Yeah. Sowhat are sort of the signals in the data that align with people who are interested?Right? Yeah. And you mentioned a couple of them earlier. Are they opening youremails? And, and just, these are just a few examples. Are they opening theiremails? Are they, are they going to your website?

Are they clicking?Yeah. When are they doing this? How often are they doing this? Had they everbought a product? When did they buy, what did they buy? How often? And so we'relooking for sort of, we always look at any sort of demographic or mm-hmm.Infographic if we're talking b2b, but we're looking for those attributes tokind of as, as a baseline, like, is this person capable of?

Buying our productsor making a donation. Yeah. But then it really comes down to the interestlevel. And that's the hard part because interest levels are fleeting andsomebody who's interested today. Yeah. Are they gonna be interested a week fromnow? Two weeks from now? Maybe, maybe not. But the best bet is if you know thatthey're interested today, get them in the hands of Yeah.

Get those prospectsand, on the desks of, of your, your revenue professionals. Yeah. And we've gotother tools like, one of our, the first tool we ever, we ever came to marketwith and it continues to be our number one seller is a tool it's called thePipeline Accelerator.

And really it's,designed to sort of take the rep bias out of, how they prioritize their, theirefforts, right? And. This just gets back to the humanity of, of, of all of uswhere, we, we will read certain signals or we'll have some compelling reason tolike focus a lot of energy on one prospect.

And that's great ifthat prospect ultimately yields the result we're looking for. Yeah. More oftenthan not, we're spinning our wheels. Right? And so we've got a tool that makessure that, that helps reps sort of. Kind of clear through the clutter and focuson those opportunities that they should be so that they're not wasting theirtime on, on frankly, folks that are, are never gonna write a check.

So, yeah. And howhas been others? But I mean, that, that gives you Yeah. Hopefully aflavor.  

Julian:Yeah. No, and, and it does and, and I'm, obviously it sounds all great, but,and how, how are you able to kind of offer that transparency in such an opaquekind of landscape in terms of, it's hard to gather that data from these differentresources because Yeah, it's great to say, but like clicks and email trackingcompletely different platforms that don't necessarily communicate.

How, how has beenthe challenge of, of building to integrate those resources and what are somethings you've learned along that process of, of building technology, beingthat, say you're not an engineering background, even though, in scalebusinesses, the technology piece is a new frontier for you.

If, if obviouslyyou've worked with them before, but, how are you able, what are some thingsthat you learned along the way that, that you were surprised about?  

Jim:Yeah, what, what you just said was one of the big learnings, cuz we go into alot of organizations early, And, they'd tell us how, how well their data wasintegrated and in a lot of places they'd say, oh hey, everything that you guysare talking about in terms of, some of these behavioral attributes, we'vealready got them in Salesforce.

Um mm-hmm that someof them, maybe more often than not though, what we found is that we had to godirectly to the original sources. And what that did is it frankly compelled us.To build an entire integration platform. And we had to do that sort of side byside. We had products that were market ready, but we had to build thisintegration platform.

So what ended uphappening is we had to invest an awful lot of time, a lot of manpower, andfrankly a lot of money in building. A, an underlying platform that was powerfuland nimble enough to deal with all sort of the, the digital marketing systems.Yeah. We work in pro sports. We've worked with several different ticketingproviders, different CRMs.

Yeah. And dif andso that, that was, that was probably the biggest thing that we found is that ifwe were going to be able to provide reliable, accurate, precise output, thatyou could go back and actually measure like. What did the PILYTIX tools say andwhat actually happened? Yeah. Like we want to be able to tell a really goodstory that this is actionable and will help you drive revenue.

Yeah. In order forus to do that, we had, we had to start with a good, clean, usable data set.Yeah. And, and part of that was just building a structure that was nimbleenough to deal with kind of all of the nuances with all of the clients that,that we worked with.  

Julian:Yeah. Yeah. Thinking about, whether it's external or internal, what are some ofthe biggest risks that you think the company faces today?

Jim:Biggest risks. Yep. Yeah. Well, I mean, I, I think, I think any company and anyfounder always has to be concerned about competition, right? Yeah. And I thinkone of the things that we have to acknowledge is, The best products don'talways win. Right. And good packaging and, and good presentation and greatmarketing can, can certainly beat a great product.

And so, yeah, whenwe look at our risk, like we've got to consistently tell our story and makesure that we continue to differentiate ourselves and differentiate what we do,how we do it. We've taken an approach of being like, Totally open andtransparent. Like if you wanna look under the hood, look under the hood.

Yeah. There's,there's always some risk that somebody who's really sharp could look deepenough under the hood and, and start to recreate our, our tool sets. I, and Isuppose that's a risk to some degree, but frankly, we'd rather err on the sideof being totally transparent because we want people to know what they'regetting.

Yeah. So, and thenthere's always, I would say the biggest risk, and unfortunately learn thislesson the hard way is, is the risk of the unknown. Right? Yeah. When, whenMarch of 2020 came around and our company was growing and we were hitting ourstride and we had, man, we had lots of pro sports clients and they were likedriving good results and they were talking about it, and frankly, they weremarketing us for us.

Then the whole,the, like, the whole industry stopped on a dime. Yeah. And and, and so like,hopefully that's a once in a lifetime like cataclysmic event. Yeah. But youknow, none of us know with any certainty, what's what's around the bend. And Ithink one of the things that we learned from that episode is we learned a lot,but.

You've gotta benimble. At the time, 90 percent-ish of our revenue was, was coming from prosports, that 90% went down to zero. Like Yeah. Almost overnight. Yeah. We hadlong-term client client contracts, but at the, at, at the end of the day, likeit's good to have focus. It's also good to have.

Enough of adiversified revenue base so that if, God forbid, something happens in onesector that, you know, yeah, you can, you can keep the lights on and, and keepgoing while, while, while you're waiting for things to, to bounce back and,yeah. Pro sports eventually bounce back. But yeah, it was, I mean, I hopethat's not a risk, but Yeah.

Who knows? Whoknows?  

Julian:Right, right. Yeah. There's not another covid. Yeah. Yeah. Agreed. Agreed. Ifyou think about, if everything goes well, what's the long term vision for thecompany?  

Jim:Yeah. And that's a question that comes up all, like all the time. And, a lot ofpeople will say like, what's your exit strategy and how, how long are you goingto do this?

That's never kindof been part of the vision. The vision has always been growth. Mm-hmm. And inthe back of my head, I, I can say if we're growing, there will always beopportunities, but get really good at what we're good at. Scoop up as muchmarket share in the markets that we're currently in.

Yeah. Between prosports, entertainment and, and certainly universities, that's a lot of terrainfor us to cover. Yeah. Keep growing, keep listening to the audience that we're,we're serving and, and, and make sure that our products are, are meeting theneeds that, that they're dealing with.

Yeah. Long term,that's, that's, that's what we're doing. And, and I'll tell you if, if timewill tell if I'm right on this, but I, I just have to believe that if we'regrowing and we're growing at a good clip and. Our employees are happy andcontributing, like good opportunities will come along.

Yeah. Does it meanwe'll be swallowed up by some bigger player? Does it mean We'll, we'll, keepgoing. And, this'll, this'll be the last company I ever worked for. I, I don'tknow. Right now the focus is growth.  

Julian:Yeah. I love that. I love this next section I called my founder faq. So I'mgonna hit you with some rapid fire questions and we'll see where we get.

Okay. First questionI always like to open up open it up with is what's particularly hard about yourjob day-to-day?

Jim:What's particularly hard about my job, day-to-day? The fire drills, theunknown, the, yeah. I'll, I'll quote the. Great philosopher Mike Tyson. Everybody'sgot a plan until they get punched in the mouth, right? Yeah. And so I, everysingle day, I, I, I start a little before eight o'clock.

I, I, I have myschedule in front of me. I, I've got my to-do list like everybody else does.And then something explodes, yeah. Hopefully it's a good explosion. Hopefullyit's somebody, who's who, who wants to talk to the CEO before they sign areally big contract. But it's always something.

Yeah. And so Iwould say for, for somebody who loves consistency and loves pattern, justgetting into a pattern yeah. That's pretty hard.  

Julian:Yeah. That's, yeah. Yeah. Thinking about also, in, in, and a lot of foundersfind that network is, is a big kind of value add in terms of going throughthose challenges, going through day-to-day, finding new strategies to,alleviate whether it's issues, how have you been able to really find thatcommunity of, at least as a founder being that now there's not a localized,obviously Austin we talked about before.

The show is definitelyan increasing localized pool of just tech talent. Entrepreneurs, leaders,innovators. But you know, in terms of the spread, it, it's fairly wide. How areyou as a founder able to continue to broaden your network while running yourcompany? Being that it's, it's a little challenging now but it's crucial tohave the right people around you.

Jim:It's really important and I'll, I'll tell you what. If I had more hours in theday, and maybe that's an excuse, but to say that I, I really wish I could spendmore time just picking the brains of, of people who have been there and donethat. Yeah. Yeah. I, I'll tell you, I try to make myself available when peopleare, are starting, people I know are starting new ventures and, Kind of goingthrough discussions like this, like the, what have you learned?

Yeah. I, I'll tellyou there, there's a few people in my very close network. I, I've got one A, afriend of mine, he's, he's become truly one of, one of the, the closest friendsI have who has been a ceo. He's a little bit older than I am. He's been doingit for a long time, and he is been phenomenally successful.

It's like everytime we talk business, I think I'm at CEO school. Right. Because, because, andit took me a while to figure this out. The, there are really no fundamentalchallenges that I have to figure out that somebody else hasn't already figuredout a hundred times before me. Yeah. And so, There, there are a few people, andI'll tell you what, I've also talked to other founders who, you ask them kindof what they did and they either clam up or they talk about luck or that typeof thing.

And I'm like, man,that we're not gonna vibe because I don't believe in the concept of luck. Goodluck, bad luck. Sure. And and, and so I, I'll tell you that the people Ireally. Look to for advice are the people who have been in the seat, the peoplewho have struggled. Yeah. The people who have gotten punched in the mouth and,and found a way to just get back up and keep going.

Yeah. And, and I'lltell you, the flip side is where don't I go from my network? In the early daysof this company, I took every single VC call they would call, right? And. Andsome of 'em had really good ideas and most of them had good intentions. Yeah.So I'm not making a judgment call, right, sure.

But when you kindof get to the, The questions of what would you do? It's so much more powerfulhearing it from somebody who is sort of out there on the ledge without a safetynet and, and, and hearing from them and what they did. Yeah.  

Julian:Yeah. And, and kind of in that same vein, what's something that you're betterat now as a founder that you wish you were better at earlier on?

Jim:Hiring people. Yeah.  

Julian:How, how's that improved and, Right. Questions. Well, right, right. Talentpool. Yeah. Curious.  

Jim:Sure. All, all of the above. But I guess, I guess the, the real sort of broadanswer to what am I better at, ideally, the things where we've made some of thebiggest mistakes.

And so, when, whenI started this and I, I did. I, I, I was really fortunate to be able to have acouple of great folks who came in early. Yeah. And were loyal and helpful. Youstart to figure out, hey, we need, we need a developer for this role, we need adata scientist for that role.

Like, and I thinkfairly, we looked at resumes and if we had nice conversations and we likedthem, we hired them. Yeah. And, and that worked sometimes and, and other timesit was like such an abysmal failure where we just hired the wrong people to thepoint like not only were they a bad fit, but yeah.

They were also kindof bringing down the temperature in the room, kind of Sure. Kind of killing thevibe a little bit. Sure. And that's like deadly. And it really, a couple ofthose earlier hires really did set us back and What we do now is, and, and wetell everybody when, when they're interviewing with us, like, it's gonna be aprocess.

You're not gonnatalk to one or two people. I, and I don't care if it's like for an entry levelwhere eh, if you, if you flame out, it's not the biggest deal or all the way upto like the, VP type of level. You're gonna talk to everybody and not literallyeverybody, but six, seven people probably.

We give everybodyon the interview in, in that interview committee, veto power. Like, if youdon't like them, if you find something, ideally you'll debate and discuss, butif there's just something that is such a red flag, okay, fine. Yeah. We, wewant to work with people that we just want to, we want to be around, yeah. Andso, I think that's been the biggest thing and, and. If it's a technical role,we really test Yeah. And push to, to find their technical chops. If it's asales and marketing role, we want some evidence that they've done it before,but then we also, we want to figure out like, how are they gonna adapt?

Yeah. Universally,I'm the last person to, to, to talk to somebody in the hiring process. I, Ialmost never talk about their skillset. I'm just trying to figure outcharacter. Yeah. And it's hard, right? People, yeah. People know how tointerview. But, one of, one of the things, and I guess the final thing I askanybody Yeah.

In addition to if,if I figured out that they've got, it looks like integrity, they, they're agood character. I also ask the question of like, what's your long term dream?Yeah. Right? For yourself, what's your goal? Right. And. I think most peopletend to give a response that they think I'm looking for, and I like, I, Iencourage 'em to back up.

Like, your goal isnot to be a senior vice president, like your dream. That's, no, nobody, nobodyever dreamed of that. What's, what's your,

Julian:you never know. Maybe PILYTIX.  

Jim:Yeah. Yeah. Hey, well I'd like, I'd like to think that, but you know.Everybody's got some ambition outside. Right? Right. Is there something in thisrole that will put them closer to that path that, that they ultimately want toachieve for themselves?

And it's reallyinteresting when you get people talking about that you, you, you figure out, isnot only are we the right fit for them, but if we are the right fit, what aresome of the things that they really value? Yeah. And some of the things thatmake them tick.  

Julian:Yeah. So yeah, I think it's, yeah, I mean, I, I love, I love the way you kindof think about, how, how somebody fits in based on what their ambitions are.

Because, ultimatelythat does arise, in terms of the work they do day to day, if they feel likeit's improving a skill that's an important, attribute for, for an eventualfuture, they're even that much more motivated to, have high pro, highproductivity, but also feel empowered feel fulfilled by that, role.

Where I think a lotof companies maybe, think too much about that particular responsibility inshort term. So, It's exciting to see that, that's kind of incorporating yourphilosophy. I think it's a mature kind of way to think about bringing peopleon, especially I'm sure at this point, it's crucial to continue to scale withthe right individuals on the team and and to continue to grow.

And I always liketo ask this next question because I love how founders extract knowledge out ofanything that they ingest. Whether it's early in your career or now, what booksor people have influenced or impacted you the most?

Jim:Books people. Well, I, it's, it's, it's interesting. I, I have such little timeto read these days that the books that I read tend to be business books. And,and they tend to be They tend to be books that are directly related to theindustries that we're in. And, and very often, I mean, look, it's, 21stCentury, I think a lot of people are writing books to have some sort of marketinfluence.

The, there's,there's the one i I most recently read and it, it did give some really goodideas. It's all sort of about the next wave of philanthropy and mm-hmm. What dowe have to think about to sort of like, achieve larger fundraising goals.Gentleman out of Australia called Ryan Jennard.

Mm-hmm. And he's inAustralia now. I got to know him a little bit when he was here in Austin. But,just like anybody who can kind of look at the same thing I'm looking at andjust have a totally different point of view on it I, I'll tell you, I am, I amnot above sort of, the, the.

The, the two minutesound, sound bites, that world that we live in where like, you get, you get onsocial media Yeah. And, they're and I, I will follow people. Sure. Specificallyon LinkedIn. I, I really don't spend any time on any of the other platforms,but on LinkedIn. There's, there's a woman that I used to work with.

She's got a hugefollowing in the in the sales and marketing space right now. Her name is JenAllen. She's with a new company I believe it's called Lavender. But like, thenagain, it's just like, yeah, anybody who can give you, in, in, in the 10minutes that you're in the car or on the subway or The, the bus coming to work.

Like anybody whocan give you 10 minutes of like really impactful, thoughtful, yeah. Just commonsense business advice. And and, and that's actually an exam. And there's a fewof those, but that one that I just mentioned yeah, we've, we've got pretty muchour, our whole revenue team here, sort of like pretty religiously followingthat one.

Yeah. Because it's,it never misses. Yeah. And so, I don't know, One of, one of these days, I mighthave a few more hours to, to pick up a few books, but yeah, it's, these daysit's kind of reserved to to folks that are sort of influencing and trying toinfluence the, the, the spaces that we're playing in.

Julian:Yeah, I'd love to ask that question too, because, founders find inspiration outof so many different ways and it really shows how many initiatives are outthere for, you to listen to one thought leader in your space, me another,another founder, and how exciting it is in terms of the shared information.

But also I think I,what I love about this podcast is, You seem to tie the, you tie the thread withhow businesses operate and how people are really, thinking about, not only thebuyer journey, what they're delivering, their value, their product. And it's,it's super cool to learn from those individuals like yourself as well.

And I know we'recoming to the, the close of the show here, Jim. So last little bit is I wannamake sure that we didn't leave anything on the table. Is there any question Ididn't ask you that I should have? Anything that we didn't chat about that wethat you wanted to bring up? Anything left on the table here?

Jim:Oh, this is your show. I'm, I'm just going around for the ride cuz I, , I'lltell you like, I, I really do enjoy , these conversations and, and, and I, Iwill, without sounding hopefully like I'm pandering to you. I, I, I will, Iwill say, I think what you're doing is playing a really valuable role because Ithink there are a lot of people out there, and I was one of them at one pointwhere you're thinking of starting something.

Yeah. And you don'tknow what you don't know. But, I, I figured probably I would make somemistakes. I figured I, I had a good vision. But yeah, that was, there, there'sso much between those two points, right? Yeah. And yeah, I, I, I think, I thinkthis is good for, for, for founders to know and, I, I don't know if this is aquestion you have to ask, but the, the question that I very often get askedmm-hmm.

From people who arethinking of starting new enterprises is the advice I give is if you've got a, abackup plan, take it, roll it into a vault and flick it in the trash. Because,because I'll tell you I probably, if I, if I was smart and reasonable, Iprobably would've started this with a backup plan in mind.

Mm-hmm. Becausethat's just a very sort of responsible thing to do. Mm-hmm. But I'll, like noneof us know what we're getting into entirely when we start this thing, thesethings, and some of the days are really, really tough and If, if there's, ifthere's, if there's a really easy exit, I think a lot of people are going totake it.

And, so I, theadvice I gave is probably not the responsible advice, but if, if you reallywanna make this work, I think you have to at least approach any sort of startupventure as. It, it has to succeed. Yeah. Yeah. Most, most of them don't, right?Yeah. Most, most of them don't. And, and I think part of it is when the goinggets tough.

I think a lot ofpeople, if there's an off ramp, they're gonna take it.  

Julian:Yeah. Yeah. It's interesting. One thing that popped into my head in response tothat was, And it's almost like visiting somewhere versus living somewhere for acertain amount of time. It's like not having the alternative to have thiscomfortable, familiar kind of, option.

But it's reallyabout giving that new opportunity a chance to actually grow, learn, and fosterthis kind of new learning. A lot of it's just shutting that door behind you andand, and throwing away the key. And, and I, and I love that philosophy cuz youknow, I did that. I'm sure you did that as well.

And I obviouslyit's painful, but you, you, you can't do it any other way. At least. At least.I, I mean, I'm in agreement. I maybe other people have a different differentopinion, but I, I don't see any way to do it.

Jim:Yeah. And I'm sure, and I'm sure there are exceptions to the rule, but I just,I, to simplify it, I, I, I really think you've gotta either be all in or allout.

Yeah. Because yeah,if, especially if you're doing anything that is new, innovative, hasn't beendone before. Yeah, it's gonna be hard. Yeah. It's, it's gonna be hard, likefull stop and you have to be ready for it.

Julian:Yeah. Yeah. Agreed. Well, Jim, I know we're at the close of the episode here.It's been such a pleasure chatting with you.

Last little bit iswhere can our audience be a fan of you? Where can we find you? Give us yourplugs, your LinkedIn, your Twitters, your, whatever we can find and support notonly you as a founder, but also you know, PILYTIX and, and what you're workingon.  

Jim:That's awesome. I appreciate that. Website is and that's P I L Y T

You can get me onLinkedIn at Jim Dries, and that's d r i e s. Pretty easy to find. There aren't,there aren't too many of us out there. But yeah, those are, those are theprimary places that you can, you can find me amazing. I encourage anyentrepreneur to, to reach out. And if, if I can carve the time, I love havingthese conversations.

I'm more than happyto share my time and anything I've learned along the way.  

Julian:Amazing. Jim, it's been such a pleasure learning from your experience, kind ofhow you've, come to, to be where you are today, what you're working on, PILYTIXand how you kind of tackle the sales process in a really, productive, and, andalmost using technology to enable already the skills people have, but, Do itmore intelligently.

Have more insightsinto what's working, what's not, and really drive, outcomes on delivering, whatthese teams are, are looking for in terms of revenue targets and, and, and, andmore strategies that they wanna accomplish. So it's been such a pleasure havingyou, Jim. Hope you enjoyed yourself and thank you again for being on the showtoday.

Jim: Idid, I had a lot of fun. Thanks Julian.  

Julian:Of course.

Other interesting podcasts