Ever been captivated by the thrill of startups? Ever pondered how some companies catapult to success while others crash and burn? Meet Sean Jacobsohn, a partner at Norwest Venture Partners and former enterprise SaaS executive. Sean's an expert in the venture capital space, and he's not afraid of failure. In fact, he’s the curator of a failure museum!
Sean’s unique perspective on failure is an inspiration for innovation and creativity. He shares his journey transitioning from business development to venture capital investing– an intriguing story that encapsulates his formidable years as a super organizer, the exhilaration of his venture capitalist career, and his current role curating the failure museum. Diving into Sean's insights, we unearth how the failure of products such as Orbitz can be a springboard for success.
But there’s more to Sean than his profession. A hardcore sports enthusiast, Sean shares how his hobby of collecting sports memorabilia helped him pay his way through college and honed his selling skills. The importance of relationship building, fostering long-term connections, and how sporting events can be a platform for this, play a big part in Sean's narrative. His love for sports segwayed into his career path and he passionately talks about his days of selling baseball cards, interning at the MLB and presenting to HBS students. Sean’s story is not just about turning passion into profession, but also highlights how failures like Coca-Cola's New Coke can be powerful learning experiences. Spend some time with us and Sean, and you'll walk away with a newfound respect for failure and the wisdom it imparts.
Producer: Anand Shah & Sandeep Parikh
Technical Director & Sound Designer: Sandeep Parikh
Executive Producers: Sandeep Parikh & Anand Shah
Editor: Sean Meagher
#innovation #technology #b2b #growth #venturecapital #vc #saas #saasmarketing #marketoutlook #abm #demandgeneration #demandgen #gotomarket #gotomarketstrategy #harvard #stanford #businessschool #sales #physics #pivot #cmo #chiefmarketingofficer #martech #b2b #b2bmarketing #ai #consultant #consulting #innovation #technology #innovatorsmindset #innovators #innovator #product #revenue #revenuegrowth #management #managementconsulting #founder #entrepreneur #entrepreneurship #data #analytics #dataanalytics #growth #growthmindset #growthhacking #salestechniques #salestips #enterprise #enterprisesolutions #enterprisesoftware #business #bschools #bschoolscholarship #siliconvalley #company #companies #smartgrowth #efficiency #money #sustainability #sustainablegrowth #process #processimprovement #customerexperience #value #valuecreation #funny #podcast #comedy #desi #indian #community
Ever been captivated by the thrill of startups? Ever pondered how some companies catapult to success while others crash and burn? Meet Sean Jacobsohn, a partner at Norwest Venture Partners and former enterprise SaaS executive. Sean's an expert in the venture capital space, and he's not afraid of failure. In fact, he’s the curator of a failure museum!
Sean’s unique perspective on failure is an inspiration for innovation and creativity. He shares his journey transitioning from business development to venture capital investing– an intriguing story that encapsulates his formidable years as a super organizer, the exhilaration of his venture capitalist career, and his current role curating the failure museum. Diving into Sean's insights, we unearth how the failure of products such as Orbitz can be a springboard for success.
But there’s more to Sean than his profession. A hardcore sports enthusiast, Sean shares how his hobby of collecting sports memorabilia helped him pay his way through college and honed his selling skills. The importance of relationship building, fostering long-term connections, and how sporting events can be a platform for this, play a big part in Sean's narrative. His love for sports segwayed into his career path and he passionately talks about his days of selling baseball cards, interning at the MLB and presenting to HBS students. Sean’s story is not just about turning passion into profession, but also highlights how failures like Coca-Cola's New Coke can be powerful learning experiences. Spend some time with us and Sean, and you'll walk away with a newfound respect for failure and the wisdom it imparts.
Producer: Anand Shah & Sandeep Parikh
Technical Director & Sound Designer: Sandeep Parikh
Executive Producers: Sandeep Parikh & Anand Shah
Editor: Sean Meagher
#innovation #technology #b2b #growth #venturecapital #vc #saas #saasmarketing #marketoutlook #abm #demandgeneration #demandgen #gotomarket #gotomarketstrategy #harvard #stanford #businessschool #sales #physics #pivot #cmo #chiefmarketingofficer #martech #b2b #b2bmarketing #ai #consultant #consulting #innovation #technology #innovatorsmindset #innovators #innovator #product #revenue #revenuegrowth #management #managementconsulting #founder #entrepreneur #entrepreneurship #data #analytics #dataanalytics #growth #growthmindset #growthhacking #salestechniques #salestips #enterprise #enterprisesolutions #enterprisesoftware #business #bschools #bschoolscholarship #siliconvalley #company #companies #smartgrowth #efficiency #money #sustainability #sustainablegrowth #process #processimprovement #customerexperience #value #valuecreation #funny #podcast #comedy #desi #indian #community
Hello and welcome to the Spark of Ages podcast, where we're talking of founders, innovators, ceos, investors, designers and artists. I'm talking game changers, about their big world changing ideas and what sparked them. I'm your host, rajiv Parikh, and I'm the CEO and founder of Position Square, a growth marketing company based in Palo Alto. So, yes, I'm a Silicon Valley entrepreneur, but I'm also a business news junkie and a history nerd. I'm fascinated by how the big world changing movements go from the spark of an idea to an innovation that reshapes our lives. In every episode, we're going to do a deep dive with our guests about what led them to their own Eureka moments and how they're going about executing it and, perhaps most importantly, how they get other people to believe in them so that their idea could also someday be a spark for the ages.
Speaker 1:This is the Spark of Ages podcast. In addition to myself, who will occasionally chime in to make sure we don't get too in the weeds with tech jargon, that's me. Yes, I'm going to do that. Today, we're going to meet with Sean Jacobson. Sean Jacobson is a partner at Northwest Venture Partners and a former enterprise SaaS executive with broad technology sales and business development expertise. He focuses on early and to late sage investment opportunities in enterprise SaaS, including mobile first business applications, human assisted AI, b2b marketplaces and industry SaaS and cloud solutions. He currently serves on the board of Elevate, enable, flowcast, legion, auro, propel, provis, horse Day and Spiff and led the investment in workado and channel 99.
Speaker 1:It's way too many boards.
Speaker 3:But hey, Sean gets around.
Speaker 1:That's all the boards. Sean was previously a venture partner at Emergence Capital Partners, where he focused on enterprise cloud investments. After being an executive and advisor at Emergence Capital portfolio companies Hytale and Duximity respectively, before emergence he was an executive at Usendit and before that he was VP of channel management at Cornerstone On Demand, a human capital management software. As a service provider, sean helped grow the company from 7 million to 75 million in revenue and 300,000 subscribers to over 7.5 million subscribers. So now that's growth baby. He knows his growth.
Speaker 3:I think I'm beginning to see why he's on all these boards. I think I get it. He's a mega, mega exponential growth.
Speaker 1:Exponential growth. He's the guy. He's an outside chief revenue officer to all these companies. That's what he learned while he worked for these companies. Sean holds an MBA from Harvard Business School and a bachelor's in marketing, finance and international business from the University of Wisconsin. He's also on the board of the University of Wisconsin Business School. He's co-founder of the HBS Alumni Angels, the largest university affiliated angel group in the world, and is the founder, chief historian and collector for the new failure museum.
Speaker 3:He's a badger, awesome. So what are you excited to talk to him about?
Speaker 1:There's so many things you can talk about with Sean. I've been very fortunate to know him basically since he came out of business school, and he is a methodical organizer of people, events and businesses. He's just amazing at how he brings people together and he does it in a just, in a stepwise fashion. I think there's so much to learn from his abilities as you build your own career, whether it's in anything, business in the arts.
Speaker 1:It could be in organizations of any kind, nonprofits. The techniques that he pursues and the passion and zest by which he does it is something we can all learn from.
Speaker 3:He better be organized. See, he's got a lot going on. I can only imagine, his Google spreadsheets are very intricate. Oh, he's all over the place with that I'm excited about this failure museum. This seems really interesting.
Speaker 1:I'll tell you it's sports Coke too. This is so funny. It's old sports teams that are defunct. It's more recently, top tech banks that have gone out of business, like SVB and First Republic, or now have been acquired or taken over by the FDIC. He just loves this stuff, and people will send him all these items so that he can put it up in his museum, and he's written short descriptions about him on his website.
Speaker 3:Okay, great. Well, let's jump into our interview with none other than Sean Jacobson.
Speaker 1:Let's go, sean. I am so glad to have my close friend, sean Jacobson here with us today. I've had the great opportunity to know him basically since we came out of business school together so that's a long time ago and I've seen his incredible career progression from business development and super organizer to venture capitalist leader and super organizer to now the curator of the failure museum. So, sean, glad to have you here. You started this thing called the failure museum. You're in the venture world. You want successes, you want home runs. Why do you care about failure so much?
Speaker 2:In November of last year I went to a Warriors game and I got an FTX sponsored bobble head and that to me was like holy cow. This is a big collectible item.
Speaker 2:I grew up being a sports collector and I'm like, wow, this is a collectible item that I hadn't thought of before. And I raced home after the game and realized I had a Webvan hockey puck. I had a bunch of other collectibles at home and then I looked on eBay. I talked to some friends, got some donations and realized there's a huge collection I could build of failed companies and failed products.
Speaker 1:So you got that cryptocurrency SBF ball and you're like I can't believe. I'm sitting, they're giving me this freebie thing of a company that's failed completely, and so that made you kind of say, well, what, let me learn about these, because are you thinking that you can help people understand from that how to work towards success. Or is it like something iterative, like you're thinking, hey, part of doing what you're doing is to fail?
Speaker 2:You know, I've been at a few early stage companies as an operator and I've been a VC for 11 years. People fail more often than they succeed, but most people only want to talk about success. That's right. You can learn just as much from failure as from success, and I want to highlight some spectacular failures that we can all learn from, and there's multiple themes that cross all these failed companies and products that I'm going to start logging about.
Speaker 1:You know like I was, it was having fun. Like you have this site that you actually put together. So this is the amazing part. Like so I'm sitting there, sean and I text each other all the time and all of a sudden he sends me a picture of the FTX ball. Then he also he finds a bunch of these old Barbie dolls that were failed Barbie dolls. Apparently there's Skipper, there's grown up Skipper.
Speaker 3:There's like weird versions of Ken and it's like when you go to the 99 cent store and they have like cinnamon Coke, you know, like cinnamon Coke.
Speaker 1:He has Coke too. And then the next, the next thing. You know, sean has a website called farriermuseum. And then one day, when I walk into Sean's house, he's got a whole display set up like a professional display. It's like this glass display with all these items there. What made you do this, sean?
Speaker 2:I've got over 200 items there now.
Speaker 1:You have museum lighting and stuff.
Speaker 2:I do have museum lighting it is. It is super fun to have family and friends over and take a look at him and you know a lot of people can relate and remember some of these failures. I'm focused on the most spectacular failures that have no chance for a rebound, but I will at some point start setting those people that have pivoted. But some of these are the most spectacular failures where they've burned through hundreds of millions or billions of dollars and went to zero, that's right.
Speaker 2:Web van 880 million raised to launch in 10 cities before they proven one. Oh my God right.
Speaker 1:Isn't that the nuttiest idea ever? Hey, let's go for broke. Let's, because we can raise the money. Let's just go build. But this was like early 2000s and they didn't want to just model one area. They just felt like the internet was gonna grow so fast and we were gonna change so fast. So they just went and built a whole bunch of distribution centers, Because you know you can just replicate everything so easily in 88 places.
Speaker 2:One of my favorite items in my museum that I just got donated is a champagne bottle from webvans 1999 IPO day.
Speaker 3:Whoa, wow, I'll see you on my website.
Speaker 2:Whoa, take a look.
Speaker 3:So you better grab some Twitter plushies. Do you have a Twitter X?
Speaker 2:I don't, but you know Twitter's not a failure.
Speaker 3:Not dead yet. Not dead yet, I'm just saying, you can go out and grab a few things. Well, you know just why is there?
Speaker 1:to.
Speaker 2:There's some recent failures I've added.
Speaker 1:That's right.
Speaker 2:Yellow trucking.
Speaker 1:That around over 100 years. That's right.
Speaker 2:You also have WeWork. They were worth 47 billion. That's right Anchorstein Brewing. They've been around since 1896.
Speaker 1:They failed, they just failed. I just ordered Anchorstein beer last night.
Speaker 2:Well, that's the last of it.
Speaker 1:They're working through the last barrel. I just had some yesterday at Gott's Roadhouse. I don't get it.
Speaker 3:I see Theranos on here.
Speaker 2:They're not making it anymore. Oh, theranos, theranos.
Speaker 1:That's a rich one.
Speaker 2:I have a Theranos lab coat.
Speaker 1:Do you have one of their machines that broke vials while I was doing it?
Speaker 2:I don't have one of their machines, but I have decided now what my Halloween costume is Theranos lab coat with Theranos hat. I also have an Elizabeth Holmes business card.
Speaker 1:Whoa, you have one of those, yes, and do you know that maybe when you meet her you can bring her some Pringles with a Lestra in it, which was the fat additive, the super fat? This was supposed to be a substitute for fat. That actually caused some issues, right, some gastric issues. That caused a little extra, anyways, so he has that in his museum. He's got just a chock full honest tea, I thought we didn't.
Speaker 2:Honest tea just went under the shoe too. That's a new one, really. I thought Coke bought them now, but I guess they killed the product, but then they just killed it.
Speaker 1:They killed the product. So there's a lot of criteria by which you look at these, because you have companies, you have products, you have sports.
Speaker 2:Toys sports teams Sports teams and toys Default sports teams A couple. I can give you some funny sports team examples. Most people didn't realize there were two NFL teams in Wisconsin.
Speaker 3:What, what they were competing.
Speaker 2:There was.
Speaker 1:This is Sean's home. Sean came from. Sean grew up in Wisconsin, Went to University of.
Speaker 3:Wisconsin Right, you're a badger.
Speaker 2:So I've been studying failed sports teams from Wisconsin and the Bay Area. So in Wisconsin you had the Milwaukee Badgers. Even though there was the Wisconsin Badgers, there's Milwaukee Badgers and the Green Bay Packers. Incredibly, Green Bay, the smaller market, Smaller market Emerged.
Speaker 1:More passion the.
Speaker 2:Milwaukee Badgers never made it. I have a 1926 program Milwaukee Badgers versus Chicago Bears.
Speaker 1:Oh my gosh.
Speaker 2:Most people didn't realize that there was an NBA team before the Bucks.
Speaker 1:What the?
Speaker 2:Sheboygan Redskins was an NBA team 20 years before the Bucks Sheboygan had a team, the Sheboygan Redskins.
Speaker 1:This is insane.
Speaker 3:This world is exploding. I always thought Sheboygan was a made up city. I thought so too.
Speaker 1:I thought that was like a term that people from the North made, the folks that had that Northwest accent.
Speaker 3:Yeah.
Speaker 1:Yeah.
Speaker 3:It was like the substitute for I'm from the middle of nowhere, I'm from Sheboygan. It's like it meant the middle of nowhere. They had an NBA team. They had an.
Speaker 1:NBA team. That's going to hurt.
Speaker 3:Seattle's feelings.
Speaker 2:There was an NHL team in the Bay Area before the Sharks.
Speaker 1:There was.
Speaker 2:You know where that was? No, I had no idea. San Francisco Seals, san Francisco. Seals, and then it moved to Oakland called Oakland Seals, then they changed it to California Seals and then it died, Died.
Speaker 1:The Seals don't make it very long.
Speaker 3:So let me ask. So what are some of the lessons or insights that you hope the visitors of your museum will learn? How do you measure the success of your museum?
Speaker 2:I just like people having a chuckle, having to laugh. I think the failed companies hit a chord and people don't laugh as much because sometimes they actually experienced that pain. But when they look at some of the failed toys and failed products they can't stand but laugh, Like some of my.
Speaker 1:Like how about the AOL Looks like in one of them? You have the AOL CD.
Speaker 2:I do.
Speaker 1:And in kind of really funky packaging, Because I remember if you were on long enough you'd get these in the mail, these ubiquitous mailers that would first be a floppy disk and later was a CD and it was the AOL. How to get onto AOL, right, with these dial-up modems. And AOL got so wedded to that business model they were not able to break out of it and broadband eventually knocked them out right. They had a walled garden internet system where you can get all your content from one place. The internet came and kind of blew it up, but in many ways there's still walled gardens. But they didn't leverage it, they didn't move to broadband fast enough, and then Time Warner took them over and the whole thing was destroyed. Got any blockbuster items? He does have blockbuster.
Speaker 2:I do have a blockbuster. I have a be kind rewind sign.
Speaker 3:Perfect.
Speaker 2:But on the product side, though I think these companies are funny and all that, I think the products are even crazier in some ways. Bic has a huge following of men and they're like we need to attract women, so let's get into some other areas. Oh, no. So they have BIC for women, pencils and pens. They have BIC pantyhose BIC pantyhose and BIC perfume. Obviously, none of those worked. They're in my museum now Harley-Davidson was like hey, we're in transportation, but why don't we get into Cologne? So I have Harley-Davidson Cologne.
Speaker 1:Does it smell like motor fuel?
Speaker 2:I haven't even opened it yet. I don't want to bother smelling it.
Speaker 1:Kind of dab it on and see if it smells like exhaust, right.
Speaker 2:They're like let's get into cosmetics. So I have Cheetos lip balm, cheetos eyeshadow flip.
Speaker 1:Cheetos, lip balm. Yes, yeah, cheetos, lip balm. Just regular Cheetos, or barbecue Cheetos, or spicy barbecue Cheetos. Did you lip balm?
Speaker 2:Maybe those would have worked. Maybe those would have worked, but credible, some of these products, amazing.
Speaker 1:I like this one. It's called Coin Digital Credit Card. It seems very digital. What Coin 2.0? What is that? It's a digital card which had a 50% failure rate which led to its demise. So was the idea of the coin thing that no one could steal your credit card Because you had to put in a code every time you were going to use it.
Speaker 2:It just didn't. So like a two-factor authentication, Like 50% of the times that people want to use it. It failed at the point of transaction. Wow, so like they would go in.
Speaker 1:They think they have amazing security, but in fact it was just an embarrassment to them. So reliability matters when you have a credit card.
Speaker 2:It's amazing how people sometimes just don't check out, check with their target market they're selling to. They don't actually check to see their product work. But something.
Speaker 1:I bet you some of these things, though they must have gone to investors like you, sean, and put together pretty elaborate business cases. Somehow these things got funded. They did what do you think they did? Like that movie pass, right, remember that thing how it exploded just a couple of years ago. A movie pass but $15 a month to go to unlimited movies.
Speaker 2:That's in my failing museum too no-transcript.
Speaker 3:I jumped in on that. That was great. What was the idea of MoviePass? It was a monthly subscription right to go see movies, see it was so.
Speaker 2:The concept was they thought this could just be like Jim membership. I'm going to get these monthly fees for the Jim membership and people won't go that often, so I'm going to make some money. The problem was people used it so much that they lost money in every customer.
Speaker 3:But it's come back Right. So I think MoviePass has come back. It's not totally dead.
Speaker 1:Well they may have. Somebody else might have bought the name. I think it's the actual theaters now having a monthly subscription. So the problem, I think, with MoviePass was that they had to pay the movie theaters when people went to it and they were hoping that what Sean's talking about kind of like Planet Fitness.
Speaker 1:you pay them 10 bucks a month but they hope you never go. But the reality is is that but if you're the actual movie theater, you can get away with it, because it's your cost, you own the, the plant facility. So if you're AMC, you can get away with something like this.
Speaker 2:And you can direct people to go to certain times that other people may not be going to movies.
Speaker 1:That's right and offer all kinds of deals. So maybe it's reincarnated in something else, which may be. Another idea about this is that just because something's failed, it doesn't mean you can't turn it in, that you can't learn from it and turn it into something else.
Speaker 2:Absolutely. I do have an example of something that turned into something else, but from a different owner Orbitz Orbitz. Orbitz was a drink, it was a lava lamp looking drink, it didn't work what. But someone liked the name travel company liked the name and took the name and turned it into something very different Turn it into a great product.
Speaker 1:A lot of people use it. They do very well in the travel business, right. The OTE, it's the OTE business, right. I even see in your museum a DeLorean, which you know. Deloreans may be gone, but the opening doors, the Go-Wing doors, are on the Tesla Model X and the latest Cybertruck is going to have a stainless steel frame. So you never know.
Speaker 3:Yeah, you never know, it may affect itself in a new way. So I'm curious, like how failure sort of inspires you. You're a VC investor. Let's just get into your background a little bit. Like how did you get into VC investing? You started in real estate and then in sales growth. So take us through to where you're at today.
Speaker 2:Yeah, I mean, I was in real estate.
Speaker 1:That's the part I don't get. Like not, I don't get. I'm actually intrigued by. So before business school Sean went, Sean worked at a real estate firm as a real estate analyst.
Speaker 2:I. My goal was always go to business school, and then at business school I tried to figure out what I wanted to do. But I had a huge interest in entrepreneurship. I ran the entrepreneurship club at business school and when I left business school, I joined Elance, which is now Upwork.
Speaker 2:That's right I joined, there was like 15 of us in a two-bitter apartment in New York, pre-revenue, pre-venture funding. We got some venture dollars from Kleiner Perkins and they moved us out to the Bay Area back when people thought you need to be local to your VC. World's different now, and so I ended up working at a few different startups wage works and then cornerstone. After that on the business development and sales side and as an operator I was doing a lot of angel investing and advising, so it was kind of doing the VC job as a hobby on the side.
Speaker 1:You were. You were actually. This is the amazing part. So Sean's has this normal job in all the different places that he had where he's an operator. Yet if you bumped into Sean and you had a business idea, he would introduce you all over the place to all these VCs. And I did this because I started a few companies. Sean started sending me stuff and people would take the meeting with me. So Sean worked this notion of building influence from the beginning right, because even when you went to business school, like you talked about, you ran a bunch of clubs, ran the entrepreneurship club, and afterwards you got involved in the HPS alumni club, the Harvard Business School alumni angels.
Speaker 2:I actually started that with Tom Cervantes. He started the HBS alumni angels, which became the largest university affiliated angel group in the world. We have 15 chapters across the world. I like the idea of people being able to share deal flow, share diligence with each other, and then one day I was asked if I wanted to become a VC.
Speaker 1:That was 11 years ago and which company were you at at the time? You were in one of emergency emergency capitals portfolio companies.
Speaker 2:I was at you send it one of emergency companies and they asked me if I wanted to join them as a VC, and that was a really pivotal moment in my career.
Speaker 1:Is this something you wanted to do? Did you want to do venture capital, like if I go back to your Harvard Business School or even your University of Wisconsin application way back? Did you write, one day I'm going to be a venture capitalist?
Speaker 2:You know, I never thought of it back then, I think, while I was an operator. It definitely appealed to me, but I never proactively interviewed for it. I think it's really hard to be a successful VC if you haven't had operating background. It's not just about picking a company, it's about winning, and a lot of times the best companies get five or six term sheets. And then it's about adding value post investment. And in order for an entrepreneur to pick you and think you can add value for the life of the company, they want to know you've been in their shoes before. That's right.
Speaker 2:You've been in the trenches you feel their pain Exactly and a lot of the entrepreneurs that I work with. They come from product and engineering backgrounds. My go to market background is a differentiator and most companies succeed or fail based on go to market not on the technology necessarily. It's usually go to market makes the difference.
Speaker 1:What does go to market mean to?
Speaker 2:you. It means picking the right early customers that will help influence the roadmap and help influence the next set of customers to come in and then scaling that in a repeatable way, moving up market, moving to other industries, finding channel partners to really amplify what you've been doing. And I find a lot of times the best distribution wins not necessarily a best product, but if you have the best product and the best distribution, it's game over.
Speaker 1:Really, and where did that insight come to you? Was that why you were at Elance? Is that why you were at Usended? Is that when you got to Cornerstone on demand? Or is it the combination of all those things?
Speaker 2:I think I saw it at all three of those places. All three of them later became public companies. I joined them all at the Series A round and they all later went public and didn't raise that much venture capital. Nowadays there's a lot more venture capital out there than back then. Cornerstone, for instance, only raised 36 million before they went public. But a big way that we got to scale was we had really good distribution, had partners all over the world represented us in accounts, so we didn't have to hire as big of a sales team as some of the competitors out there.
Speaker 1:So when you are at Cornerstone, right, I think one of the things you did is you built up that channel capability, and when you were building that channel capability, how did you do well where others would? What did you see as your strength? A lot of this is like you have to get someone else interested in promoting your product, your technology product, which was basically learning and training services. This was a software product, all about helping companies develop their own people.
Speaker 2:I mean, the best partners are those where your product will help them sell more of their own product. So I found other HR software products where what we had we had learning management, performance management and recruiting some other HR software companies and HR services companies that didn't have those but their customers were likely asking it for those where, by adding our product to their suite, they could beat certain competitors in the market. And so I found resellers in places where our direct sales force wasn't strong, so down market certain industries like higher education, healthcare, international. And then we found referral partners where our sales team was strong, you know other services firms, some handful of software firms, so then we could hire a much smaller sales team and have a lot more leverage.
Speaker 1:That's amazing. So because of that leverage, because you were helping and you were giving them referrals or you were helping their services capabilities right, you were, you were triangulating how they get value from you you were able to amplify your whole sales team.
Speaker 2:I was and we had resellers, so in some people like ADP had several thousand sales people reselling our product.
Speaker 1:That's a huge home run, right? You don't have to hire that many folks. You can hire folks that help train them.
Speaker 2:And they're upselling the cornerstone product to their customers. It's really hard to get your own new logo. It's a lot easier when a partner can sell their new product to their own customer. Yeah, they already have a relationship.
Speaker 1:It actually gives them a reason to come in and hang out with you, right, Like I'm not just here to play golf or go to dinner or whatever. Hey, I got something cool in you to talk about with you, right, Because otherwise they're like, oh, another payroll thing, whatever. You know. Yay, you added benefits, right, but now they had something really interesting and new to sell and that added value to them. So then you went from there and then you eventually went into the venture world. How did you find the right companies to invest in? Right, there's a lot of venture folks out there and emergence has done very well, but it's not one of the ones you hear about, like you know, you hear about the five top five or six. How did you differentiate?
Speaker 2:I find that a lot of ECs have their own thesis and otherwise it's really hard to focus your energy. My thesis is next generation players where there's disruptible incumbents. So I look at companies where there's SAS 1.0 or on premise products that people are using not because they love them but because they're the only options. So if you look at Cornerstone, for instance, there were on-premise products that we replaced. You look at wage works, where I was at before, we were replacing some SaaS 1.0 products. So I saw that as an operator and I brought that into my venture career.
Speaker 1:Right, so there's already budgets, there's already a buying process, there's already a known category, already a known category that you look it up.
Speaker 2:And I find a lot of companies out there are creating new behavior and if you train people on this new behavior then they try to sell you a product and then that might be a long sale cycle. Small ACV in a year. They'll tell you if they like that new behavior.
Speaker 1:Right, so it's like a missionary sell.
Speaker 2:Yeah, and it's really hard for a startup on very little money to do well on a missionary evangelistic sale, Right.
Speaker 1:so they're established lane and you just come in and say I got something that'll do the same job that you're doing today, but much better. Yeah, it did, or lower cost or more integration with other capabilities.
Speaker 2:Yeah, if you think about it, in a lot of cases it's a next generation solution that is much easier for employees to use, much easier to implement, much easier to configure to your use case. Now, it doesn't mean that you're always doing replacements. You may be augmenting right, yeah, like an example, spf. So SPF is in the Sales Commission Management Space.
Speaker 1:Still today, 70s. There's Caledis in this area.
Speaker 2:Caledis, exactly. But today about 75% of companies are doing things on spreadsheets In part because they think Caledis and exactly are hard to use and hard to implement. Spf will replace them in some deals, but in other cases they're replacing spreadsheets. But it's a known category, a known software that exactly and Caledis created the market for.
Speaker 1:Right. I mean, there's another one like a workado, right. There's how many players in this iPad space. Or there's MuleSoft. There's tons and tons of companies, right, and they're coming in and they raise something like $400 million, right? It's a tremendous amount of capital in a space that was pretty well known, but they transformed it.
Speaker 2:And that team comes from one of the legacy players, tipco. And then you've got Flowcast, which is the next generation of Blackline Legion's, the next generation of Chronos Elevates, the next generation of Wageworks. So, that one's like really close to my heart because they're disrupting one of my former employers.
Speaker 1:It's amazing. So you take that approach and then find those entrepreneurs. Do you look for them, or they come to you?
Speaker 2:I mean, it goes both ways, but in most cases I've identified a legacy product that needs to be disrupted and I go out there and try to find someone doing something at space. There is one company where I saw the same opportunity, but I couldn't find a company I liked, and that's Oro. I actually found the team to work on this together.
Speaker 1:What does Oro do?
Speaker 2:Oro's in the procurement software space.
Speaker 1:There's lots of those Koopa Ariba.
Speaker 2:There are a lot of those, but they're doing supplier relationship management or maybe a CRM for suppliers. Koopa and Ariba do that on the side, but I thought there was an opportunity to do this as a standalone company and they do. Compliment on Ariba or Koopa today.
Speaker 1:So you found the team from your former contacts, or did you find it? So one of the things I find interesting about the way Sean does things, he's got a set of ways to meet with you.
Speaker 3:It just sounds like if Sean's researching your company or your field, you better watch out. That means you're ripe for disruption, it seems like to me.
Speaker 2:Well, that team actually, I met through Legion, so the CEO of Legion was the chief product officer of Ariba and I met the next chief product officer of Ariba through him, and that is the person that is now CEO of Oro.
Speaker 1:That's amazing, and how'd you meet him, sean? You got an introduction.
Speaker 2:I got an introduction.
Speaker 1:But there's something I'm Sean, so Sean is a super organizer, so he just doesn't reach out randomly to something or someone or something. So usually you like going to sports games, right, you like going to the Warriors, you like to go to the Niners, you like to go to the Giants.
Speaker 2:Well with him. I actually got to know him through golf, oh, through golf. At the time he was golfing more than he does now, but at the time we got to know each other in the golf course and then eventually decided to work together.
Speaker 1:Amazing. You'll have like a weekly golf thing and you'll invite three or four people every time. I'll try to golf a couple times a month and bring entrepreneurs some in the portfolio, some outside the portfolio, all right so one of the things I think that's interesting about you, Sean, is that you run all these ways of organizing people and bring into your network in a super disciplined way.
Speaker 1:And some of them can be around golf. He's put up a pickleball court in his yard in Hillsborough. Oh yeah, pickleball's all the rage. He, through the business school alumni clubs, has sports events or a sports night where you meet the management of the team. You sit and ask them questions beforehand. You get to meet, sometimes the president, the general manager, ask about business, ask about their players and then you watch the game together. It's a networking thing.
Speaker 2:I mean, I love sports, but I also love the business of sports and the only way you can get access to some of these people the presidents, the GMs, the CIOs of the team, or if you bring people they want to meet. So, depending on how much capacity they have, we'll get anywhere from 50 to 150 HBS alumni on an annual basis to go to the Giants, the 49ers, the Warriors, the Sharks.
Speaker 2:And even the earthquakes and the earthquakes. And we have done it at the A's and the Kings before and we'll have them talk to us before the game and then we'll sit in a box after the game and they'll come and interact with us.
Speaker 1:So it's like a multi-way thing. You endear yourself to the team because you're helping them with their business development effort, providing a great experience to people who went to some of the schools involved, right. And then they all come together at this one place, so, and you get to watch the game too, so it's a right.
Speaker 3:I've gotten a chance to watch, meet the Giants and put on their rings, put on their World Series rings, and meet their president and general manager, and it's just a super fun time, right, and you create a special experience with everyone Do you find that like is the idea that you because if you're playing golf and pickleball with these folks you know is the idea that you sort of get people you know outside of the pitch, so to speak, so that you can kind of find out who they are really Like? What are you looking for when you're having these you know out of the boardroom meetings?
Speaker 2:That's a good question. I mean, I think our philosophy at Norwest is don't be the lunch guy. No one remembers the guy that takes you to lunch. Yeah, and lunch is typically like an hour. What I like about sports going to sports or playing sports is you spend four or five hours with the person. You really get a chance to know them. You know when you, when you invest in someone, you're you're investing in a company for next 10 to 12 years. You want to know that they're coachable, that you can work with them, that other people will want to work for them. I mean, a big job as a CEO is hiring people, is selling the prospects, taking care of customers, fundraising, and you're going to go through some very tough times together and you want to know that you can work together and I think sometimes you can get into some incredible conversations when you're together for four or five hours.
Speaker 1:Right, yeah, it's really powerful, right, it's way beyond the surface, because you know.
Speaker 1:If it's one thing, well, you have the game. So you know you're going to go for something where you can split your attention right between the game and hanging out. But then before that, you get together, you chat, you have some drinks together and you're creating multiple experiences within the experience and in that way you get to see that person and how they act with you and act with each other and act with others, because many times you just don't go with them. Go with that one person, you'll take two or three other people.
Speaker 3:This is why my move when I was dating, before I settled down with my wife, was bar hopping, and it took you a long time. Something took me a little bit, but it was bar hopping. That was. My move Was like all right, if this first experience is going well, let's get out of this place and go to the next spot, grab some tacos across the street. Let's go to the next spot, let's go to this next fun thing, because then you have like four or five experiences in one evening and you have so many outs, there's so many places you can be like well, that was great, my Uber's coming.
Speaker 2:But if it went well, like it did with my, wife.
Speaker 3:But our first date, it was it was. We went to five spots together. We just couldn't get enough of each other. We kept wanting to hang out.
Speaker 1:In your case, you guys started. You guys just started dancing randomly, Isn't that something like?
Speaker 3:that, yeah, but our first official date we met on the dance floor bar. First official date was was this multiple spot adventure. And I think when you go through something, you have this shared experience. You feel like in one night you've you've known this person for months. You kind of come out of that with this broader perspective on them.
Speaker 1:Did you do this before you started as a VC, or were you doing this before that?
Speaker 2:I probably have done it more, since I've been a VC, but I still think it was important on the sales side and the business development side to build these deep relationships, because it's not just about the transaction. You're also building a long-term relationship, huge relationship, it could be it could be as long as.
Speaker 1:As many marriages right. I mean you could. If you come in at seed stage or series A stage, you could be working with this person for over 10 years and then maybe you're going to fund them in their next company, which I think you've done. Yeah, that's pretty amazing. When you were in business school and you decided to go down the entrepreneurship route, what inspired you? Was it your mother, father, family experience? Did you bump into someone that became your mentor? Or was it a book you read? What got you into this?
Speaker 2:Well, probably it wasn't from family, because most of the people in my family were doctors or teachers, so I was the first one to, you know, get into the business world.
Speaker 3:I think.
Speaker 2:At HBS it allowed me to explore a lot of different avenues and, running the entrepreneurship club, I got a chance to meet so many entrepreneurs that changed the world and I got super excited about that.
Speaker 1:I mean, you were in the middle of the technology revolution, right? So the internet revolution, that was 1996.
Speaker 2:Is when we started HBS and we left in 98. It was a rage now.
Speaker 1:Yeah, and a lot of people out of business school would go investment banking or consulting. That was straightforward way to make money. But you said, no, I want to be in entrepreneurship. Was there like a class? Or you just said this seems cool.
Speaker 2:I did take one class which I thought was super cool, but you know, when I was coming out, most of our classmates are going to like B2C internet companies, and I never could really understand how to attract and retain consumers. And some of those people picked good companies. Most of them didn't, but I've I always understood if you could solve the business's problem and solve it well, they will stay with you forever, and then you could sell more things to them on top of it. So I pursued the B2B path right out of business school and that's my whole career has been focused on B2B.
Speaker 3:So what got you into business? Like you know, if you, if you were raised by doctors and teachers, you know what was the kindling that even got you excited about going to B school.
Speaker 2:But you know I did have a hobby that became a business growing up. I had a sports collectibles business in middle school, high school and college.
Speaker 1:There you go Sports collectibles. Yeah, so you were. You collecting cards, or?
Speaker 2:I was collecting cards and autographs, memorabilia so I was doing it for fun. But then I realized, hey, I can actually build a bigger collection if I buy and sell and make a profit off of some things that I didn't want as much, and so I know a pretty big collection that I've held on to for a long, long time. It also helped pay my way through college.
Speaker 1:Really.
Speaker 2:I had advertisements all over campus University of Wisconsin saying I was buying collections. So I buy people's entire collections and sell the pieces.
Speaker 3:Wow, ok, yes, you break it down. You buy like a whole set of baseball cards and then sell like the whatever top 10 best cards or something like that.
Speaker 2:Well, I'd buy way more than that. I mean people. Let's say I'll buy things where people have like 100 sets and tens of thousands of cards and yeah, I could sell the sets or the individual cards or mix. You know, I did do some traveling Like this is kind of pre-internet. I would travel to a city that would appreciate certain players, like people will pay a premium for Yankees players in New York.
Speaker 3:Sure.
Speaker 2:They'll pay a premium for Cubs and White Sox players in Chicago, so I would do a little bit of traveling. Sell these for a premium.
Speaker 3:Yeah, this makes so much sense. This is how all my cousins ripped me off is that they would always like include a Red Sox player and trade for cards, and I would just be a sucker for it. You know it'd be like.
Speaker 1:It'd be like I would want to call your Stremsky card or Jim Rice card.
Speaker 3:No not even a no, no, that it'd be like. It'd be like Rich Gedman, It'd be some. It'd be some bench number.
Speaker 2:Oh, come on.
Speaker 3:And I'd be like, wow, that's a red Little Buckner yeah. I mean Buckner might be worth something.
Speaker 1:Yeah. So you actually then said I'm going to go city to city, take all these, all these cards I bought and then try to sell them. Would you go to card card conventions?
Speaker 2:Yeah, I went to. I went to card conventions in different cities.
Speaker 1:That's amazing. And then you just figured this out and it became one of your obsessions or one of your passions. I'd say not. I wouldn't say obsession.
Speaker 3:Is this where you learned how to be a salesman, how to sell?
Speaker 2:I think that's probably where I learned the selling part of it. Yeah, it kind of came naturally to me and I was able to do it with something that I had a huge passion for. And then, if you think about that sports collectible business and hobby, when I got that FTX sponsor bobblehead at the Warriors game, it brought back memories and made me miss collecting and it brought out a new set of collectibles in my life.
Speaker 1:So now you know, like, okay, I can take that same passion for sports, transfer it a bit to the world of business, transfer it to products that people beyond sports, that people know and touch and, like some of I don't know if you saw the Barbie movie, but some of your collectibles, the some of the failed Barbie products, what's the one growing up, skipper, growing up, skipper, pregnant. Barbie pregnant Barbie all of a sudden. Like people can relate to that and it's a great conversation piece.
Speaker 2:Yep, All of the discontinued Barbies that are highlighted in the Barbie movie I have in my music you had it, I think, before the before the movie. I got this stuff before the music before the movie Now it's a lot harder to get these items. That's right.
Speaker 1:Well, that's really fantastic, sean. I think it's super fun and super interesting to learn about what got you into this whole game. Now, at the stage of career that you're at, what you know you're, you've been in adventure capital for quite some time now. How many years?
Speaker 2:11 years 11 years.
Speaker 1:Is this what you see yourself doing for a long time? Do you ever see yourself becoming an operator? I know you've operated our friends group, our walking group, but would you ever be an operator again?
Speaker 2:I think this is my last career move.
Speaker 1:This is your last.
Speaker 2:Being at Northwest. I love being a VC. It's amazing privilege to have a chance to help so many entrepreneurs change the world. I can't imagine walking away from my colleagues at Northwest and my portfolio companies. It's a perfect job for me.
Speaker 1:In a way, you're still an operator because some of your own portfolio companies have talked about during board meetings. They have the Sean pipeline, so you are actually one of their channel sources.
Speaker 2:I always tell my companies I want to be their number one lead source. I am out there all the time.
Speaker 1:That's really awesome. Say you were in a in a parallel universe and there was anything else you would do. What would it be? It could be you could do podcasts, you could do presentations, you could do art, you could do riding motorcycles, you could play. You could be a golf pro. Sean, imagine you could be a golf pro, maybe.
Speaker 2:What would you be, I mean, if I had to turn back the clock and I had the skills? I love to have been a baseball player.
Speaker 3:All right.
Speaker 2:I grew up playing baseball, played with my father. A lot went to a lot of games with a problem in Wisconsin it was cold half a year so I couldn't play.
Speaker 3:Didn't you also have an internship at MLB?
Speaker 2:I had an internship at MLB where I worked with the CFO, and I'm starting to see my son in me to some level. He's eight years old. Every day I'm home. He wants to play baseball. He was in two baseball camps this summer. He's going to be in a baseball camp through the school year. I never had that type of opportunity in Wisconsin. There weren't those kind of camps and he couldn't play baseball year-round, and I've been a coach for his last two years of baseball.
Speaker 1:It is the most fun ever to be a coach, isn't it?
Speaker 2:It is so fun.
Speaker 3:I love it, Can't wait. I got a four year old. I can't wait.
Speaker 1:I'd say I have four kids and I got a chance to coach every one of them at some level in soccer, early soccer or baseball or something, and I would say, as the fatherhood experience, probably my best experience with them, because I could put them out there, I could work with them and other kids. You saw the growth of kids, especially when they're super young and they're totally unskilled, from that to actually being able to catch or throw a ball or kick a ball or something like that, or be a teammate. That's it. I think there's nothing more fulfilling than when you see that growth. And then one of the things we used to do at the end of the season is we would, whatever team we were, if we were the Red Sox or the Yankees or some soccer team we would make their own baseball cards with a picture of that player and them and say how they are like that player. So, like Arjun, my son is like a little Pele. He's super fast, super nimble, and we would relate that player to the person.
Speaker 1:Yeah, those are collectibles and the kids always like Arjun, still has that it is on his side.
Speaker 3:I wanna get his autograph. There you go. It's amazing, no, I mean. That's why I always go back to like gymnastics teacher when people for that question of like, if money wasn't an object, you know what would I do. It's like the purity of just being with children and watching them sort of progress and being such an instrumental part of that. I think there's nothing more honestly fulfilling personally. So it makes a lot of sense. But you wanna be the player. If you had the skills, were you? I just wanna know like, were you a competitive in baseball growing?
Speaker 1:up I was very competitive in baseball. Sean is competitive today at everything he does.
Speaker 3:So what was your position?
Speaker 2:You know I was a pitcher earlier on, but then I gravitated more toward outfield.
Speaker 1:Who's your favorite outfielder?
Speaker 2:My favorite outfielder today.
Speaker 1:Of all time Either one Of all time.
Speaker 2:I mean probably Robin Yacht.
Speaker 3:Oh, okay, growing up in Wisconsin, yeah, yeah, yeah Makes sense. I idolized. I'm curious why didn't you go into the business of sports? Did you ever consider that?
Speaker 2:Yeah, I considered it. You know, I did internship in Major League Baseball. I did a one year field study for the NFL. I didn't feel like there was a same sort of entrepreneurial opportunity. There's a lot of structure in these leagues and teams, not a lot of opportunity to do things entrepreneurially. So I decided I'd rather be a fan than an employee and I enjoy the sport a lot more being a fan. Yeah, that makes sense.
Speaker 3:I love that.
Speaker 1:Sean, I think this was a great experience, great talking with you about all your experiences. I've known Sean for 20 years or more and I got to learn some new things about Sean. I love the baseball card collector and the sports card collector portion, and then how that passion enabled him to get into business of all different levels, eventually into venture, and then come back on this interesting failure museum, which is so relatable now because it goes back to being able to collect and being able to share, and then from that passion you get to do what you love to do all the time. It's really fun.
Speaker 3:To me. What I've learned from Sean is how, throughout his life, it really seems like he turned his passion into his product. They always say follow your passion, follow your passion. But if you can't turn it into a product, if you can't turn it into something marketable, sellable, or in some way have it actually fill the coffers and support you, then that can be actually kind of a destructive path. But it seems like you always found a way to make it very productive, whether it was hocking baseball cards across the country or getting an internship at the MLB, or figuring out how to get to the Golden State Warriors president to present to HBS students. I mean, you kept it always close to you in a way that sounds like it really fueled you all the way through, and so to me that's my big takeaway.
Speaker 1:If there's one thing I'd say I learned from Sean the most over the years is try to do the things that you love to do and make that part of your whole world, like there's not a work world and a friend world. You can literally fuse together all your interests and let them all enable. It's like building that flywheel. You can build that flywheel If you love people, if you love certain things, you can incorporate people into this and they all build upon each other. And one of the great things I get to look forward to every week is at least almost every single week, I get a text from Sean about something. So I want to keep that going for the rest of my life.
Speaker 3:All right, thank you, sean. Thank you, thank you.
Speaker 1:So what do you think? I was really excited to sit down with Sean. I've known him for a long time and I've been as good friends, but I learned new things about him.
Speaker 3:Just talking about all this failure in sports, you know it just brings me back to Buckner, that ball going through his legs and how it changed, obviously, his life. It's like you can't control that part right. The part you can control is the diligence, the work that you put in every day, the effort, the incremental effort that you put in, not the results. Sometimes that's up to a lot of other capricious.
Speaker 1:And so for every new Coke which is widely judged as a failure, coca-cola is still running and is still one of the most profitable probably the most profitable beverage company and food company in the world. So from that failure they keep learning, and from other people's failures we can learn a lot, and I think that's the cool part about that museum you can reflect on something, you can laugh about something, but then you can learn from it and from the seeds of it, build something amazing.
Speaker 3:But you know how this podcast doesn't become a failure. Is if everyone listening goes ahead and gives us a rating and a comment. Right, that's what we need.
Speaker 1:That's what we need.
Speaker 3:So help us not become a failure by jumping in there if you're on Apple or Spotify or Stitcher or wherever else you're listening to this to drop in a comment. It's been such a pleasure Rajeev doing this one with you. It's a huge pleasure with you something. ["sunday Perique"]. All right, this show is produced by Sundee Perique and Anand Shah, production assistants by Tarant Alley, edited by Sean Mayer. This has been an effin' funny production. ["sunday Perique"].