Why I Quit Being a Cop to Work in Tech Sales
What would make a decorated federal investigator quit his job to start over at the bottom of the tech sales ladder? This video is the unfiltered story of Why I Quit Being a Cop to Work in Tech Sales. Taft Love shares his journey from working on a federal white-collar crime task force to grinding it out in San Francisco tech sales, including the day the CIA shut down his investigation.
Guest
Taft Love
Founder, Iceberg RevOps
Chapters
Full Transcript
Taft Love: I didn't work any drugs, but, uh, I can tell you at a local level, there are elements of it that feel pretty true. Like not the, the sexy side of it. The, the, again, like the brilliant people running these things. I, I don't really know if that's the case, but it's another place where like the level of coordination I found pretty interesting and, you know, I, I arrested people who had hookups in other cities or other states. For serious amounts of drugs when they had a windfall or finished selling whatever batch they'd had, and it is its own economy.
Sean Weisbrot: Taft's Love is a former police officer and federal investigator turned sales operations leader. He's built sales, sales development and operations teams for high growth startups like Panda Doc, smart recruiters, DocSend, and now leads sales teams at Dropbox. He also is the founder and chairman of a company called Iceberg Rev Ops, a revenue operations consulting firm that serves high growth startups. When he is not selling things or advising. He's flying his plane on volunteer missions to help people in need to get care. In this episode, we talked about his past as a cop, his experiences in Korea as well as mine in China, and we touched upon his experience with sales, what drove him to be in sales, and how all of these pieces of experience in his life are part of a long thread that string together in a way that brings us through a story. His journey in life was very fascinating and my only regret is that we didn't have enough time because we started late. So it's possible I'll bring him back on another episode in order to continue the discussion, especially talking about his volunteering with charity and flying his plane, which sounds so cool. I know you're gonna love this episode, and I know you're gonna love Taft. Please enjoy the show. So you were a police officer in the past and you decided to go into sales. What happened in your life that made you go. One thing doesn't suit me anymore and I need to do this other thing.
Taft Love: It's a good question. I think there are a few things there. There are a few elements that came together here. Uh, the first is my, my mom, uh, has been in sales all her life. Um, she was a pharmaceutical sales rep when I was a little kid. Switched to selling for a big furniture company and worked her way up to their VP of sales when I was in middle school. And, uh, and still today, like running a small furniture company. And that CEO job is a lot of selling. So first I watched my mom have control over her financial destiny and go from my parents having essentially nothing, um, to being, you know, they're not, they're not wealthy, but they, they do well and she has control over how much she makes. And I found law enforcement really interesting and I loved it. But, you know, I was coming up on 30 years old and I had never made $30,000 in a year. And I was the youngest in my department to become a detective. I then went on to join a federal task force. Uh, and had, I did, I did pretty well and it just didn't matter financially and career trajectory wise, I was waiting on the people above me in the chain of command to retire or die. And that's how you move up it. Uh, it's not a meritocracy the way that I watched my mom thrive in one. I thought somewhat naively, somewhat correctly, that like, Hey, I, I think I can do well at anything you plug me into. I think I have the right, uh, the right stuff to be successful. Anywhere you put me, I just need a chance. And so I spent a couple years trying to get a sales job, but I was in rural North Carolina and so small town, there weren't many good sales jobs to begin with. And the ones I applied for nobody. Uh, I rarely got a call and didn't know how to do well in an interview. So, um, I knew I wanted to make the switch and just had to figure out how. And so I'll pause there 'cause I think that answers the question of like, what, what led from one to the other.
Sean Weisbrot: I kind of feel like being in any position in a company where you're not the CEO, you're kind of waiting for your superiors anyways. No,
Taft Love: no. I think that is the case a lot of times. But PandaDoc is an example of where I came in as a brand new account executive and the sales team worked for me 18 months later and. I skipped the line in a big way by solving problems. Other people just sort of considered it part of the job.
Sean Weisbrot: Well, that's good to know. I have to say PandaDoc is not sponsoring this. I do use it. I do pay for it. It is pretty good software. So, PandaDoc, if you wanna talk to me after this, I'm happy to consider a sponsorship from you. So it took you a long time to try to find an opportunity. What was that breakthrough moment for you that made it, made the switch happen?
Taft Love: I got a job with the Secret Service. So, the context here is, uh, even though I was on a federal task force, I still was employed by my local agency. They essentially lend out and a local detective who has a skillset they want or need for, for their, uh. For whatever the task force is doing, you know? So I was on loan from my, uh, from my department, so I was making no money. I put myself through undergrad and grad school as a cop was making effectively no money. I had a Bank of America credit card with like 20,000 in debt from putting myself through school on it and was losing money, just surviving. So. I applied for federal jobs. 'cause a lot of the guys I work with were FBI, secret Service, DEA and IRS. And I was cross swearing with the IRS. And so the Secret Service guys said, Hey, we do a lot of this white collar crime stuff. You should come apply with us. And so I did. I. Then, uh, around, I think it was like 2010, 2011, I can't remember exactly now. I, uh, I finally got through their process. I was essentially guaranteed a job, and then Congress didn't pass a budget and everything froze, and I threw my hands up and said, I'm gonna go do something else somewhere. Interesting. I, I lived in a. A wonderful small town and then drove down the road to go to work at a small town that had more tattoos than teeth. And, uh, I was, you know, uh, I, I wasn't enjoying it anymore and didn't feel like I had anywhere to go. So I quit my job and I had been reading a blog that a friend of a friend wrote from her school in Korea. For a year or two and I decided like, I'm gonna go do that. Seems interesting. I've never seen that part of the world. I'm gone and spent two and a half years living in Korea, um, working for, uh, several schools. And when I came home, my whole family had moved to, uh, San Francisco. They lived in Sausalito, actually right across the bridge. And so I got a Craigslist ad for, uh, the first was selling Google. Uh, back when Google hired local, uh, photography companies to do 360 photos inside of businesses, when that was like a brand new thing and I spent a few weeks banging my head against the wall, doing that, had no sales training, didn't know what I was doing, didn't make a single sale, and then ended up with a an SDR job at a startup where I got a little more support. And the rest is a kind of history that even though that company shut down a year later, I went to LeadGenius and then Panic, and then Smart Recruiters and then DocSend, where we were acquired by Dropbox. And so just, you know, got really lucky.
Sean Weisbrot: Okay. You've shared a tremendous amount of history in like five seconds and there's so much that I could ask you about, especially the chorea experience. As a person who has lived in Asia, I think there's a lot we could commiserate about. I've never been to Korea. I'll just leave that there for a moment.
Taft Love: Where were you in Asia?
Sean Weisbrot: Uh, China and Vietnam. So we'll leave that there for a moment before we go into Korea, because eventually I would like to get back to sales in kind of your journey with that. But before we do that. I have to know, what was one of the craziest experiences you had working at the federal level? Like a specific case that you might be allowed to say something about that was like, holy crap,
Taft Love: I didn't work, I didn't work anything so sexy that there are things I can't really talk about. Um, I did white collar crime, so lots of financial crime. Embezzlement the thing we, our task force, the way all of our cases started were, uh, the Patriot Act has, um. Has a provision for these things called sars. Suspicious activity reports. Banks, if they see something that meets the sort of federal guidelines for like, this is a suspicious activity, you should report it. They submit these reports. Uh, the most common is called deposit structuring. You walk in and out $9,900 of cash in the bank every day for a week, so you don't hit the $10,000 limit. And a lot of people do this expecting that as long as they don't hit the limit, nobody will ever notice. And of course banks, you do that even one time and banks start looking at you funny and ask if you want to do it, do you want to go ahead and report it just in case? And people say, no, no, no, it's not 10,000. And uh, so that's one way that we got pulled into cases. And so anyway, we had, uh, we had one. The worst name ever. We were, we were, uh, we were doing an interesting case that that dealt with people, um, with convenience stores, essentially scamming the welfare system, the, the WIC system specifically. And so this is food stamps. And the way it works today, unlike back in the day when it was actual stamps, now it's a card you get from the government. Lots of people need and, and survive off of this, uh, this support. It's a great program. And there are a lot of stores out there that, that essentially steal from the program. And so what you do is if you are a recipient, and let's say you, you are, uh, you're a drug addict. You, you want the money, not the food. And, and this is fairly uncommon across all people, but there, there's a subset of of recipients who, who scan the system. And so you go into a store and if your store is participating in a scam, which we were investigating, a large ring of them. You go in, you hand them your card and you tell them, Hey, I get $800 a month from the government. And they say, okay, here's $400. Give me your card. And they spend the month running your card for non-existent goods. So they make it look like you've come into their store 15 times this month and bought things. And it's a fairly sophisticated system. The thing that was most interesting to me is they, uh. They do not, um, there is no middleman that money is coming from the treasury into their bank account. So they are something about the, like lack of a middleman really bothered me. Like, my taxes go into the treasury and they're stealing from that account. And it just, I think all of us were, were bothered by that. Uh, among many other things. And so worst name, how large was the ring? I can't remember. It was dozens of stores all owned by one family. And,
Sean Weisbrot: but I mean, like in terms of the amount of money that was being handled.
Taft Love: Oh, we're talking, uh, dozens of millions of dollars a year across many, many stores across several states. Um, it is a lot of money and, um, not all of it was this scam. There were other scams that it did, but this was the biggest, this made up the bear share of their sort of, uh, fraudulent revenue. And so, um, there were, uh, we investigated this for a while and worst name ever one of the FBI guys, uh, because it's all convenience stores, named it Operation Inconvenience, which like, he got shit for forever. And, uh, so we, uh, we had like a war room for this because it kept getting bigger and bigger and bigger. And another element of this, another thing they did was they paid these people you call Smurfs. Like, uh, if you, if you know about like meth, Smurfs, Smurfs are the people you pay to go buy, uh, the ingredients for math. But another way that you use the term smurf is like people who go steal things for you and then you fence them. They also had a ring of people who would go to hundreds of other stores, Walgreens, CVS, stuff like that, steal things, and they had a giant warehouse of stuff, more millions of dollars where they're reselling stuff from other stores. They actually started a wholesale business selling into Walgreens and CVS and places they were stealing from. It was really sophisticated. And so one day we come into our war room and, uh, our boss, one of the assistant US attorneys for this case, he was assigned to us for this case, and he was like, well, uh, we're done. We were like, what are you talking about? We've been working on this for a couple years, and he was like, gotta got a visit today. The case is gone, another agency has it. We're like, we're. Four of the biggest federal agencies plus me, four biggest federal agencies and Lenoir Police Department, uh, are represented here. It reminds me of the, uh, as individuals we're formidable, but together, bill Gates and I are worth in excess of $20 billion. Um, so the, uh, uh, yeah, we were just like, what, what the hell? What's going on? And we, we don't know, but we are. We think that CIA took it from us because the owners were, uh, middle Eastern immigrants who had strong ties back to, uh, Pakistan. And we, we suspect and don't know and can't prove. And we were just left to wonder, um, we think it was taken from us because. Interrupting that money supply might have, have messed up another case. Uh, you know, an international case that we didn't have ties to. So that was the most interesting. It just disappeared.
Sean Weisbrot: Or the CIA was running it and they were funneling money to the Middle East in order to support someone that was against the ruling party of Pakistan. And they didn't want you to, you know. Takeover.
Taft Love: I don't know. I, I like to think, I don't know. I like to think that they would've just given these people the money and not stolen from, from welfare and, and businesses. But you know what? Also the, they gave guns to inner cities. So I, I don't, uh, uh, I don't know. I, nothing would surprise me, but I, I, I have no idea.
Sean Weisbrot: How did it feel to have the case taken away from you with no explanation?
Taft Love: It sort of bothered me for a couple days, but. You can either trust that there's some bigger goal being served or you can be pissed about it and let it bother you. And it's the old, like, this isn't a, an exact fit for the, for it, but like hatred is like drinking poison and hoping the other guy dies. There was a little bit of like, look, I can let this just really piss me off and I'm, I'm not gonna move on. We plenty of other cases to work and. A lot of other cases had big impacts on our local communities too, which was my angle in all of these cases.
Sean Weisbrot: Was there something specific that you learned from the case as a human being that's affected your life since then?
Taft Love: I think it just opened my eyes to the, the level of coordination that happens in some of these criminal enterprises and. This isn't like on TV where there are like brilliant, sophisticated people running it, but like minus the characters. A lot of things you see on tv, like they're, they're rooted in, in reality more than I realized working as a local officer and detective, I didn't see the scale of these things. And so we would have people, I guarantee you I worked cases as a detective where Walgreens got, you know, had. $500 worth of stuff stolen. And to me that was an isolated incident. So getting to zoom out and see that, like, Hey, I bet some of these cases I worked and, and just like couldn't solve. Are tied to this bigger thing than, than like, we got our arms around with, uh, with the help of a lot of agencies.
Sean Weisbrot: Hey, just gimme 10 seconds of your time. I really appreciate you listening to the episode so far and I hope you're loving it. And if you are. I would love to ask you to subscribe to the channel because what we do is a lot of work and every week we bring you a new guest and a new story. And what we do requires so much love so that we can bring you something amazing. And every week we're trying really hard to get better guests that have better stories and improve our ability to tell their stories. So your subscription lets the algorithm know that what we're doing is fantastic and. No commitment. It's free to do. And if you don't like what we're doing later on, you can always unsubscribe. And either way, we would love a like if you don't feel like subscribing at this time. Thank you very much and we'll take you back to the show now. Have you seen the show Breaking Bad?
Taft Love: Yeah. Yeah. I love that show.
Sean Weisbrot: Was there any truth to it from the point of view of a federal agent and what you've seen?
Taft Love: I didn't work any drugs, but, uh, I can tell you at a local level there are elements of it that feel pretty true. Like not the, the sexy side of it. The, the, again, like the brilliant people running these things. I, I don't really know if that's the case, but. It's another place where like the level of coordination I found pretty, uh, pretty interesting. And, you know, I, I arrested people who had hookups in other cities or other states for serious amounts of drugs when they had a windfall or finished selling whatever batch they'd had. And it is its own economy and that is super interesting. And in that sense, I. I think minus a lot of the like, you know, hitman stuff and a lot of the violence is a little over the top and probably not. True to life, but, but a lot of the other stuff feels kind of real.
Sean Weisbrot: Let's move on to Korea, 'cause I think we, let's, let's lighten the mood a little bit. Okay. How old were you when you moved to Korea? Where in Korea did you move and what were your expectations of Korea? And, we'll, we will stop there.
Taft Love: Good questions. Uh, I was 27, so I was among the older people there. It was a lot of like 22, 23, 24 year olds with me. Um, I moved to a town called Daegu, which is a familiar, um, a Koreans will call it a small town. It's the size of Chicago. And my expectations, I honestly, this is, this is true of me across a lot of my life and really frustrating to my, to my wife, I think. I didn't take any expectations with me. I tend not to, to like get really hyped about what something's gonna be and just like try to enjoy the experience. So I showed up knowing that it was gonna be weird and different to relative to what I'm used to, but I having no expectations and I, I am happy to dive into this was. Very helpful because I had a, a rough experience early on. And so had that been like a bubble burst relative to these, like really high expectations, it would've been harder to deal with. But, um, I essentially got thrown in the deep end in the sense that I was assigned to a, a school that had what they call a, uh, uh. Oh my gosh, I can't remember what they call 'em now, but the teachers who were assigned to foreigners to like help you around and get you settled in and, uh, the one at my school, her husband's mom got sick. They moved back with his family in the UK like a week before I got there. And the guy that was assigned to me didn't know enough English to even explain that to me. And so I was in the deep end, uh, in a rural school, just left to fend for myself essentially. And so no expectations were, were, uh, that was very helpful.
Sean Weisbrot: I think having no expectations is a great way to go through life because if you have an expectation and your expectation isn't what you experience. Then you're either going to be excited by an underestimation of the expectation or disappointed by overestimating the expectation. And so by having no expectation, you free yourself and allow yourself to just experience what comes. So you asked about. China and all that. I was there for 10 years. I also lived in a rural town called Wuhan.
Taft Love: That's where my youngest sister was born. She's adopted from China. She's from Wuhan.
Sean Weisbrot: Cool. I was there 2008 to 2013, and I thought it was going to be a rural town. I was very wrong and completely misled by the person who helped me find the job. In a good way, in a bad way. Good. Because it was a metropolis, but it wasn't modern. And so there were things about life that were more forward thinking and like there were, there were more modern aspects than in America, but some aspects were far behind the us. And so I felt a lot more free in a way, but I also felt more constricted. I felt more free because I could pay for cash. I could pay everything with cash. I could like get a motorbike and ride, ride around on the streets. I could basically do whatever I wanted and nobody cared as long as I wasn't hurting anybody. It was like lawless in a way, but constricted because there was very little I could do. Nobody spoke English, which I had no expectation that anyone could speak English. And I was happy that I ended up there because if I hadn't ended up in Wuhan, I probably wouldn't be able to speak Chinese. Soon after I arrived, the social media platforms got banned and they were never unbound, and so my 10 years in China. When I was in China, I didn't have access to Western social media, and I barely even looked at YouTube. So in a way, I felt like my twenties were probably a lot simpler and happier than most Westerners because I wasn't becoming addicted to social media, and I'm still not addicted to social media. I barely touched social media. Even into my late thirties. But from a business point of view, now being out of China and back in the West, it's a detriment because there's so much about social media that I don't understand that I'm now having to learn about. I'm having to pay Gen Zers to teach me how to do it. So that's a, a high level, brief overview of my experience in, in China. Uh, I wanna delve a little bit more into Korea 'cause I don't know anything about Korea and. If anyone's listened to, you know, multiple episodes, I talk about China probably once every six or seven episodes. 'cause people like, it's, it's new for every guest because they don't know my backstory. But the audience has probably heard elements of it. So I try, if I do talk about it, I try to speak about it in a different way each time so that it's new for them. Anyways, so you mentioned the, the city, town, whatever you wanna call it. Daegu, a good British friend of mine I met in Vietnam, had a girlfriend from Daegu, and so that's all I know. I think Daegu was the town that had the church with the Super spreader event in COVID a few years back, if I'm not wrong. I think so. I think so. There was like 30,000 people got infected because of like one person from one event. They went to, they went to like an event that was in a, a stadium for this group, and they just got everybody infected.
Taft Love: Oh my. So we, I guess you were in the, or you lived in the place? That was the original super spreader. And then I live in a, a place that was, had a 30,000 person event,
Sean Weisbrot: but I left Wuhan like seven years before COVID started. Right. So I haven't even been back there in like nine years. To Wuhan. To Wuhan, yeah. Although I still talk to my friend. They've got like seven or eight friends that I'm, I still talk to that are in Wuhan. So as COVID was starting, I got to hear what was happening in Wuhan that no one else knew about unless they were from Wuhan. And yeah, it was, uh, quite scary. But that's a different conversation. So. How long did you end up staying in Korea? I think you said, was it two years? Three years. What was the most important thing that you learned about Koreans living there and about yourself? 'cause I learned a lot about myself living in China. So I'm curious what you've learned.
Taft Love: Biggest thing, I don't know if this is gonna be a very satisfying answer, but I, I think it's the most honest one is growing up, first of all, growing up in, in a, you know, rural southern town, there were not many foreigners generally, like everybody was white or black, Southern and Baptist like that. That was our community and. So we, uh, and, and I think from media, I had this, this impression of basically all East Asians, as you know, smart and great students and you know, things that in hindsight are totally silly. But I had never had any experiences that sort of disabused me of this notion before. And so for me, the biggest thing was I, I remember telling my parents a, a few months into being there and it was like. It's just like America in terms of like, people are just people and different personalities and there are kids who are, who fit the stereotype as we see it, and most of them absolutely don't. And some, some people there are assholes. Most people are nice. And it's just like the cross section of Korea in terms of just things other than culture and language are the exact same as as the US.
Sean Weisbrot: So your biggest takeaway was people are people no matter what culture they're from.
Taft Love: Yeah. I, I think so. I, that was a big one coming from my sort of, yeah, some sheltered, not in the, not in the like helicopter parenting sense, but in the like small town not having seen the world since.
Sean Weisbrot: That's still a profound kind of lesson because so many people grow up inside their own culture. I. Don't have the opportunity to experience someone else's. You may go to like Greece for a week with your wife. What do you get? You get some beach, you get some boat. You don't get Greek culture, right? You may go to Portugal for a week, you'll see the church. That's like a thousand years old, right? But you're not gonna get the people. So you have to stay somewhere for at least a month before you can really get a, a small insight into those people. And oftentimes I think Americans are probably really guilty of this is. Making the assumption that America is the greatest country in the world and Americans are the greatest people in the world and everyone else is beneath that. And I can say that I experienced that as a younger person and having left, you know, the US at such a young age, I was 22, that I started to realize from the people I met that like America is not that great actually. Like no, country is great and a lot of countries are actually bad if neutral, neutral, if you're lucky, bad, most commonly, especially when you look at what their governments are doing in different countries. And so I came to fall in love with China knowing that China had a ton of problems. Accepting that the US had a ton of problems, realizing that those problems are not gonna change, but finding that, you know, they're both great, but they're both not good. And the question of where is the best place to live is a matter of the place that you feel the problems are not insurmountable. And I would rather have lived in China than in the US because of my experience with learning the language. And as a result, getting into the culture and feeling included in society in a way that I felt I didn't really, I, I, I wasn't really able to in the us. You go, but you're American. Like you're a, a white, cis male, you're America. But, but like, I don't feel American. I don't, I mean, I, there there's elements of American culture that I have tried desperately to beat out of myself and cannot, and traveling through dozens of countries has been helpful, but. For most people, you will always be that thing you present as, and so when I'm in America, I'm American. When I'm in Germany, I'm American. Even though I look German and have a German last name in China, I look American. Even though I can speak Chinese and if they don't see my face, they don't know that I'm not Chinese from my accent or from the way that I speak. Yet, I will still always be that thing that I don't wanna be, and so the most important thing that I've found is home is where you feel the most comfortable and you're able to tolerate the, the, the problems. It's kind of like, it's kinda like marriage, and I can say this because I've been married and divorced. The best kind of marriage is one where you understand the flaws of your partner and their flaws are not insurmountable or they're not completely unacceptable. They're they're tolerable because everyone has flaws, and those flaws will piss you off. At some point, and it depends on how you handle it. So you have to have a humor about it because you are gonna have flaws and you are gonna piss off your partner. And that's just life. And if you're gonna commit to being together for potentially decades, 50, 60 years, suffer some people, you just have to learn to tolerate it. And so it's like, it's the same thing with where you choose to live and what company you choose to work for, or what company you choose to run. Bring it back to the business side, right. So, is there anything else about Korea you wanna share before we kind of get back into business mode? No, I, I can't think of anything. I have a question. What's your favorite Korean food?
Taft Love: Oh, man. So I would say it's, uh, this fermented stew called, uh, Jiang. It's, uh. Uh, yeah, like, uh, fermented soybean stew. That was my absolute favorite.
Sean Weisbrot: That sounds delicious. You'll have to send me the name of that written down so I can look at the Korean restaurants.
Taft Love: Yeah, you got it.
Sean Weisbrot: It's a, it's a vegetarian dish, I imagine.
Taft Love: Yeah. It's often, is it often also paired with seafood, but Yeah, at its base, it's a vegetarian dish.
Sean Weisbrot: Love it. Totally interested. Love Korean food. I love the dish where it's like the cylinders of, uh, rice. It's like li liquified rice that's then formed into a cylinder. Yeah. Doc, when you put hot, spicy sauce on it. Mm. That's so good.
Taft Love: That's everywhere. Street food, all over Korea. You can get Yeah. Dock is what it's called. It's a, a bunch of different forms it takes, but yeah, that's the most common one.
Sean Weisbrot: So let's get back to. Business, sales leadership's, all this. Yeah. You've, you've worked for Panda Doc, you've worked for DocSend. Mm-hmm. I'm noticing a pattern here of document, document signing. Was there anything about documents that, that was sexy for you because you were maybe in the past working as a police officer and an investigator that something you just like crossing t's and dotting i's, or was there something else that drew you to those businesses?
Taft Love: I think it's almost entirely coincidence up until Dropbox, really. Um, and now funny enough, I run the Inbound sales program across several Dropbox products. One of them is Hello Sign. And so, um, now, now Dropbox sign and no, I, I think it was, it was mostly coincidence and I joined, I. Because it was a job that was available and my, uh, I wanted to sell something interesting that I had used before and liked, and so that, that was an obvious choice for me. Um, DocSend, I, the product was almost incidental. I really loved the founders and these three guys were. Smart and humble and thoughtful and treated their company well and and so I joined because of them and it just happens that it's in the same space. I think they liked me because of my history of documents more than I liked DocSend because it's a document startup.
Sean Weisbrot: Fair enough. DocSend, it sounds like you joined DocSend at an early time since you had a meeting with all three founders.
Taft Love: Yeah, it was, it was pretty early. Even when Dropbox acquired us, we were fewer than a hundred employees. Um, so I, I joined when we were, I don't know, 30 and, uh, I already knew one of the founders pretty well from just our social slash business network. And then the other two, I got to know them pretty quickly and figured out like, oh, these, it's two more. Guys who, who are a lot like Russ and in terms of the culture, I think they're building. And so it was a, it was a very easy sale for me.
Sean Weisbrot: Fair enough. I, I don't want to discount, there's two other things that I wanna mention, which I, I don't know how to fit all the time in for, unfortunately. But you also co-founded a, a revenue operations consulting firm. Which is one of the reasons why we're talking, 'cause generally I only interview people that are running companies. Um, even though you were introduced as someone working for a company. Uh, so the fact that you have your own company pre-qualifies you. Um, what's the difference between selling for someone else and selling for yourself? Because you have a consulting company and you've got those clients, and so you have to sell those clients on why they need. Revenue operations. So what's the difference between selling for yourself and selling for others?
Taft Love: From in, in the sense of how I think about it, there's zero difference because even though I, I work for Dropbox, I very much think of myself as the CEO of my teams. And I, the fact that, that I'm not the one, you know, it's not my bank account, the money's going into doesn't really matter. Uh. That and that attitude has served me well. So I've really leaned into it, but I tell all of my sales reps, you're the, you're the CEO of your role. If you are anything else, this isn't gonna work. So, no, I, I don't actually treat them differently at all. Um, and I, I don't sell much iceberg anymore. I, I have a. A CEO who I hired a year ago once we grew to a point where it was hard to manage two things at once. And so I'm, I'm founder slash advisor more than, uh, more than in it day to day. But I still help out with sales here and there. And I'm a big believer in, there was a podcast I listened to years ago where their, their mantra, the thing they said all the time was, have a mindset of plin and be helpful. Those were the two rules for sales. Um, no one deal ever matters so much that you should do anything other than be helpful. And if you do those two things, you will succeed in sales. And it's been true for me. I, I, so I treat both sales exactly the same.
Sean Weisbrot: So then, what's the most important thing you've learned from having your own company? Because I believe it's your first
Taft Love: Yes. Yeah. It's, it's my first, it was for the first. 18 months, just me doing consulting on my own early mornings with east coast companies before I started my day job. Now it's grown to, we're 11 or 12 people now, and I think the biggest thing I've learned is once you get even past your first few employees, I, I started seeing areas where I had holes as a leader and, and gaps, and it took me longer than it should have to. Both recognize and address them, but filling, understanding that you have gaps, knowing where they are and filling them with people who have those strengths is how you build a good company. And that's something I, I spent a year or two sort of in the doldrums, you know, not, not understanding well enough and learning the hard way, but that's the biggest takeaway for me, is that's how you build a strong company.
Sean Weisbrot: All right. I love it. Is there any one last final piece of advice that you would give people about life, travel, experience, anything that your grand vision of the, the future, whatever it may be?
Taft Love: I think this has worked well for me. I don't know if it'll work as well for other people, but my general advice is say, yes, it has worked in life. Say yes to opportunities that that come along. And as long as they're not dangerous or, or cost you too much, then, then say yes to things. And, um, that's been true for conversations with random people where I've, I've, you know, had amazing experiences thanks to that, all the way to, um. You know, work asking you to do something that isn't on your five year plan.




