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in all these roles, what you’re signing up to do first and foremost is to be a change agent. And you’re signing up to come in and really understand and listen like what is what is it that the business is really trying to do, and apply some of the tactics on how you go, go do it.

That’s Tim cop, who’s an investor at Hyde Park Venture Partners. And he’s one of my greatest mentors of all time, he was actually my lifeline when I was first stepping into my role as a marketing lead many years ago. And at the time, he was the CMO of ExactTarget. That’s chief marketing officer. And ExactTarget, or E T, was a marketing tech company based in Indianapolis, Indiana, that grew from a startup to IPO to the eventual sale to Salesforce for $2.5 billion. Now prior to that, Tim had some really cool experiences, leading marketing at web trends, and actually got his start in marketing, working for consumer brands, like Procter and Gamble, and Coca Cola. So Tim has a really unique perspective. And it also had some challenges going from B to C, that’s business to consumer to B to B, that’s business to business. But he also transitioned from this non tech industry into the SAS or software as a service industry. And we talk a lot about that as well. We talk about building brand and building a culture that lasts. We also dive into how to learn as you go and create your own playbook, which Tim is just a master at. There’s so much goodness in this conversation that I think we should just jump right in. So let’s set this thing off. Hey, Tim, thanks so much for doing this. Man. I am really excited to talk to you. You and I have go back many, many years. And I have just so many questions for you. But But first, just wanted to say thanks so much for being here.

Oh, yeah. Thanks for having me excited to do it. Of course, of course,

your thought leadership in the marketing space, particularly in in SAS, and technology is unparalleled. And I think of you as one of my top mentors in my entire career, when I started my career as Director of Marketing at slingshot back in the day, you are my lifeline man, like, I I probably had some we had fun. We had a blast. I probably had more stupid questions than I could possibly count. But I appreciate your patience. And I hope we can capture some of that in this interview here today.

Yeah, sure. That’d be great. Be fun. And luck. You You taught me a lot as well.

I appreciate that. Maybe maybe what not to do. Don’t Don’t do it. This young Sparky kid is doing and be a bull in the china shop. I really, really love the story of what you were doing when we first met back when you were the CMO of exact target. But before we dive into that story, I wanted to get a little bit more perspective on your earlier days and your experience working at some of the world’s biggest brands like Procter and Gamble and Coca Cola. Can you tell me Tim, what, what drew you to that first role in marketing at Procter and Gamble? And was that your first role in marketing?

Yeah, it was. So I started off early in my career bounced around doing a couple different things, mostly like in banking. My undergrad was finance and accounting, believe it or not, and went back to school. When when this whole era of the cloud started to come about, I realized I didn’t really have the tech chops that I needed. So I got my MBA in information technology. And then coming out of my MBA was recruited to p&g they dropped me in this role, kind of to help help the IT organization engaged with business and drive transformation. And the first role they put me in was as a Lotus Notes developer, and I can probably say it was the worst Lotus Notes developer all time. There was somebody worse than me, I’d like to meet them. And around that time, it was not called digital marketing. But all this work around websites and email and how do we use digital to help help build the brands was coming about so I ended up becoming one of the first digital marketing managers interactive marketing managers and was fortunate through that to be embedded with a couple of brand teams and got to do the launch of crest whitening plus scope, which was an Crest White Strips, which were both just amazing. And then was asked to kind of take a leap into the brand world for a while and that’s how it came about. I get to work side by side with a lot of the color leads in the brand world and frankly, at p&g, all the good action was happening and the brand’s that’s where you wanted to be. So that was kind of my lucky break, and how I ended up moving into marketing. And I was always this guy who came at it from this sideways view of how do you use technology? And how do you disrupt things?

Did it feel right when he made that transition from being in a Lotus Notes developer to being a brand marketer? It was,

so it was gradual. Thank god it looks. So here’s the thing about marketing, I think a lot of what is being taught in school on how to do marketing has nothing to do with how to be a marketer today, in some ways, the playing field was pretty equal, particularly when you think about digital, there was no playbook, I was literally making it up as I went. So if I had six months of experience that was probably six months more than anybody else had. ahead of the curve that I had going for me, no, it wasn’t natural at first, it was in some ways, because at first I thought I wanted to do architecture. And so I’ve always had this side of me that geared toward building things, and creative and design. And really, I just thought, like marketing was really like sales. I didn’t I don’t think I really knew what marketing was. And the more I think marketing is a lot of strategy. And I realized, man, I liked this work, the more of it I did. Well,

what were some of the external struggles you faced as you made that transition? I mean, obviously, obviously, you’re having an internal struggle kind of being like, Is this my identity? Is this what I want to invest my career into? But were there external struggles and that you’re facing there at the same time?

Yeah, it was funny that I was. So look, I was the only non Ivy League brand marketer in my class, he recruits from the best of the best. And, you know, I’m the scrappy kid who grew up in Cincinnati and went to the University of Cincinnati. And so what I didn’t have an Ivy League connections and pedigree I think I tried to make up for and scrap and hustle and trying to go about it in a different different way.

Can you give me an example of that?

Well, sure. I mean, literally. So when I looked at everything kind of went through PNG and classes. So you know, and a lot of it, like I said, recruiting from the best of the best, that is where you wanted to work 20 years ago, it is what you know, Google or Facebook, or fill in the blank is today, like one of the top questions you get asked as soon as you would meet other people, where do you go to school? Where do you do this? What fraternity where you answer, there’s this kind of this immediate sizing up particularly as you started to engage with the agency world. So everything that we did at p&g, really, at that time, a lot of it was project managing things with agencies, I mean, a brand team, even for a big team would be four to five people. And so like, you know, the entire Chris White Strips team, you could you could fit around a table. And but you know, our media budget was, you know, over $100 million. So a lot of it was the small team doing a lot of the strategy and getting the consumer insights, but working in this totally foreign world being dropped into one of the biggest, you know, creative agencies in New York, and trying to figure out how to develop advertising. Like I said, the good news is I don’t think anybody had a playbook for that. But you certainly feel like a fish out of water first.

I love that phrase, sort of like, I don’t think there was a playbook, right? Because I think one of the things I’ve noticed, over my time collaborating with us, you always had a playbook you already you’re always creating a plan and running by some sort of playbook even if it was the one that you created. Do you remember your first plan as it pertained to sort of your career in marketing?

You know, it’s funny, you make it sound far more organized than it is only and only with the benefit of hindsight, do I sometimes, you know, realize it was writing, you know, the playbook. And what I do what I found about myself, as I always like to take on new things, things that haven’t been done before, let’s go figure out how to do this. So as it moved into the world of software, which we’ll come on to later, how do you bring kind of a radical b2c mindset into a stodgy kind of stale b2b world? And how did those things come together? And there wasn’t a playbook for how you build a brand or kind of what a modern marketer should be within a b2b organization. Look, a lot of what I tried to do was go off and learn from some of the very best. So when I arrived at exact target, there was two people that really impressed me which were salesforce.com and Omniture. And I just went and studied everything they did, and and I went to all their user conferences, I studied all their meetups and groups, I’ve talked to some of the key leaders that are talking to their customers. So I think a lot of what’s happening is just not assuming you know the answer, but just observing, listening, what’s going on asking a lot of the right questions, taking a lot of what you think might work based on that kind of getting some pattern recognition that you will on the kind of things that work, but then not copying Exactly. How do you put your own flavor on it? You can’t just go from company to company and do the same things. Every company has its own unique culture and business plan and approach and what worked. But strategy, a strategy and execution is execution. And there’s some core principles you can apply. You just can’t copy all the tactics.

I love that. I think there’s definitely a unique flavor and style to everything I’ve seen you do. And I probably tried to mimic your patterns, maybe maybe too much to the point of being copycat until I realized I needed to put my own spin on it and adopt it, per the industry that I was in at the time when you’re in those roles at p&g, and Coca Cola. And even at Web Trends. As you were kind of creating this plan as you went along. What kind of walls Did you hit along the way? And is there one particular you can think of that sort of stopped you in your tracks for a little longer than some of the other walls that you either broke through or hurdled with a little more ease?

I’ve not really thought about it in that way. But I think what comes to mind for me is just an all these roles, what you’re signing up to do first and foremost is to be a change agent, and you’re signing up to come in and really understand and listen like, what is what is it that the business is really trying to do and apply some of the tactics on how you go go do it. And the problem is, in doing that is you’re always trying to drive change. And the bigger a company is, the more difficult it can be. So there’s a lot of incumbency and bureaucracy. And that’s not the way that we used to do it. And that’s ultimately what led me away from some of the larger companies to be honest, and to things that are more fast moving and more nimble. So one of my favorite stories, Matt, is if you remember back when coke did the whole Diet Coke Mentos debacle from maybe 10 years ago now. Yeah, so it was amazing to hear. For those who aren’t aware, there was this period of coke bottles, and you’ve dropped Mentos, and I’m in with cause basically an explosion. So that’s either an opportunity or it’s a crisis. And it depends on how you looked at it. And I think coke at the time viewed it as a crisis. The guys who were off doing this, were called EP Burton, they ended up creating these huge fountains like the Bellagio fountains, and all these crazy things they ended up doing by by dropping Mentos and Coke and creating extraordinary experiments and cokes original response was they have to stop, you can’t do that. And Coke is very safe. And it’s not meant to play games with and some things like that. It was just more of a it was a bit like, you know, we’re coke. And you can’t do that to us. Well, look, the reality is the world has changed the Internet came about and consumers will do whatever they want. And the mandate from my boss was go make it stop. And I was like, I can’t make it stop. And even if I could make it stop, I don’t think we want to make it stop. So what I ended up doing was in Look, you can’t seek permission on this, you kind of have to seek forgiveness. So I reached out to the guys who created this, these crazy fountains and then went work with my team. And we created I don’t think I’ve ever had a chance to tell this whole story publicly. So it’s fun, cool. We went off and created the first video that launched on Google just after they had bought YouTube. And what it ended up being was the biggest Best Diet Coke Mentos experiment ever. And basically, we ended up bringing a lot of coke to them. And we let them do what they do. And we set it all up in a giant field. It was incredible. You can find it on Google, if you go and look. And at the end, it just said brought to brought to you by your friends at Coca Cola. And it completely changed the narrative. And it put us from being on the defensive. You can’t do this to us too, you know, maybe poking a little bit of fun at ourselves and kind of rolling Coke is meant to have fun. It’s about you know, celebrating a lifestyle and finding Americana and all these things. And it kind of tapped into that main vein, if I would have sat around and waited for permission, man, I’d still be sitting there. Nobody could approve that. It’s just you have to go off and do it. Because because it’s the right thing to do. And you believe

it’s such a cool case study. And it’s almost like you took a wall that you hit and turn it into a bridge that added a whole new dimension to the brand. Yeah, it

was it was a lot of fun. I did go home and tell my wife that night, we might need to pack our boxes to be ready to move. And it all worked out.

I love that you never shy away from taking a calculated risk. You’ve got to well, so you transition from this world of big brands and, and consumer brands to the enterprise and enterprise software and technology. Why did you decide to make that jump? And what were you seeking in that transition?

Yeah, there’s a number of reasons. But I remember the moment that hit me over the head and so like a lot of changes that can hit you gradually and suddenly all at the same time. So I think after 10 years of being in CPG at my core I knew I was probably built are born to do something else that was a bit more innovative, fast paced, and remember being in a planning meeting we’re talking about instead of growing at 4% What would it take to really break out and grow at 5% And, and this is true. And I was thinking I like but this is not for me. No. And it just hits you in that very moment that I was probably, you know, I could do this work, but I think what I was most uniquely created to do something else. And at the time look, I mean, it seems pretty obvious that a lot of the best work is happening and b2b marketing. Now, I think anyway, and 10 years ago, that was certainly not the case, I think there was only it was probably fewer than five b2b companies that even had a CMO 10 or 11 years ago. So for me, it was driven out of if I’ve been able to do any one thing, well, somehow, luckily, I’ve been able to spot trends, and I just really had this instinct. 20 years ago, digital marketing was the place to be then 10 years ago, this advent of on premise software to cloud and SaaS was the place to be. And at Koch, we were big users of web trends. And I ended up joining their customer advisory board, and then moved from the customer advisory board, they asked me to join their board of directors. And then from the board role, they asked me to kind of step into a CMO role. So tactically, that’s kind of kind of how it happened. And why I did it is, you know, after 10 years, I was ready for a change. And I was looking for what would be the next wave of things, and really just had this feeling it would be in SAS, and what we now call SAS, and how do we bring more of a disruptive kind of b2c mindset? And web turns? Was that a $75 million run rate business at the time, so way, way smaller than Coke, what do you make meaningful brand of coke? And people thought I was nuts for leaving? And maybe I was, but you know, it, it played out played out very well.

Yeah, hindsight is 2021 of one of the things you said actually reminds me of this of a story. And the thing you said was, you were thinking at the time when you’re at Coca Cola, that maybe this isn’t the thing you’re most uniquely qualified to do. And it reminds me of a story where you and I were grabbing lunch as, as we did at the Weber Grill downtown Indianapolis, one of your favorite spots. And it was a transition point in my career. And I was I was debating whether or not to go full time on unversioned powderkeg. And what we were doing, and was was really grappling with that decision. And I love your mentorship style 10 because you tend to mentor not necessarily in directives, but in questions. And the question that you posed to me was, Matt, you have to ask yourself, what is it that you can go and be best? In the world at? Yeah, not be good at what Yeah, can you do? What could you make work? And have it be a career that is success, quote, unquote, successful? But what can you go and be best in the world at? Yeah, and I wanted to ask you, I guess my question to you is, why is that such an important question to ask yourself, in your career, and in your life?

Well, I think there’s a couple of things. One, I mean, the bottom line is we’ve all been created in very different ways. And I think we all have our own unique giftings. And now more so than ever, there’s just unlimited variety and the things you can go do, or you can go create whatever you want to go do. And look, I think I would have been a fine brand manager at p&g. I hope so. And if I had really grinded it out, maybe I’d be one of 500 marketing directors, there still are 1000, or whatever number they have. But I would have been one of many. And hopefully I would have found a way to kind of hold my own. But I realized I was wired in a different way, which was, you know, to more about recognizing patterns and trends and creating new things and weaving together b2b and b2c. And so I think what ends up coming out of that is honestly, you’re just happier. When you’re doing what you were meant to do what you were uniquely created to do, you’re just a lot happier. The problem is, you’re not entirely sure what you’re made to do until you try a number of things. And so it doesn’t always hit you right away. And sometimes you got to go and experiment, try a few different things. But listen to that inner voice when you when you’re feeling like you’re off track or being pushed or nudged or called in a different direction.

I love that I think more data is always more helpful and can help you better understand what you could be best in the world. And I want to thank you, Tim for that advice, because I think it’s probably one of my most repeated pieces of advice that I’ve been I’ve ever gotten. I look

you’re doing it right. Yeah, I mean, you could have been one of several 100 directors VPs of marketing and a SaaS company. But what you’ve been able to do now with powderkeg is a platform and what you’re building out that that I believe is what you are pretty uniquely created to do, and few other few other people could do that in the way you have. So I think you’re finding your way.

I appreciate that Tim I could Do it without mentors like you. So I really, really do appreciate that,

you know, we all need it, because there’s things that other people see in us. And sometimes you just, you just have to ask, kind of have this, like personal board of advisors, I think 28 people giving you advice, but who are the, you know, four to six people who really care about you and know about you, and will kind of speak truth to you and can kind of push or nudge you in the right direction. And, you know, let you know, when you’re off track or say, Boy, I think I think you might have a calling to go and do this, which you might be really good at, we will talk about exact target. But what’s fascinating in that whole journey is I would say 80% of the people I hired had never had marketing experience. And it was just looking for people who had a calling to kind of do something else.

And I want to definitely want to get into the story of exact target. And when asked one more question before we take a quick break. And that question is for your personal board of advisors, Tim, who is that first person in the SAS world in the technology world when you made that transition to Webtrends? That was one of your first sort of personal board of advisors in that new role.

You know, the problem with some of the career path I’ve chosen, Matt is I’ve not had those people in the way I would want or hope. Because when I chose to do that, what if I wanted to ask people, should I go be a b2b cmo? They were like, well, what is that? I don’t know what a CMO like it was, it was such a novel sort of idea. They didn’t know. But what I did tracks, I didn’t have anybody within SAS, but it was very honest with my leaders at Coke, and they knew what things I was built to do. I was very honest with them. So a lot of it was just going back and you almost have to look backwards, I think for mentors and find people that you’ve worked side by side with and earn their trust and respect. And they’ll be very honest with you and vice versa. So I was more looking back on, you know, who are a couple of my key key managers at p&g, and, and in coke, so I went to them.

Is there one in particular that, that you remember or recall as kind of giving you some advice, whether it was in the gentle questioning way that I associate with you, or maybe even more of a tough love sort of feedback?

Yeah, the few that jumped out one, you know, my dad, well, he doesn’t know, he still doesn’t even know what I do. What do you think he knows a lot about me and can just just ask questions, you know, and things for him. Like you’ve kind of made in some ways your VP of Digital Marketing at Coke, when you’re 29 years old? What in the world? Are you doing leaving to go to a startup? It could be that direct with me. Yeah, you know, I appreciated that I probably needed that question. Scott McCune, who was my boss at Koch, and now an investor in our fund and continuing to work with him and Mark rate Rex, who’s now the CMO at Cox Communications, used to lead marketing at AOL. Those were the folks that work most closely with a coke. And at first, they have to get over kind of this thing of boy, I think I want to leave, but through that, I think, you know, when you work side by side with somebody and you’re going to war, and you’re going to battle with with people every day that they want what’s best for you. And so once they get over the okay, you’re probably gonna go, then it’s trying to help kind of guide you in the right direction. And obviously, then kind of pushing you off with support and encouragement. So I was I was lucky to have that with both Scott and Mark.

Well, I appreciate you sharing that, Tim. And we’re going to take a quick break. But when we come back, we’re going to dive into some of the patterns you recognize working at a web trends and then exact target to the, you know, eventual IPO and sale of that company. But then even talk about some of your investments as an angel investor, and a venture partner at Hyde Park ventures. So don’t go anywhere, and we’ll be right back. Thanks for listening to powderkeg igniting startups. I wanted to take a minute to make sure you know that this episode is powered by verge in network of local communities with global reach for tech entrepreneurs, investors and top talent outside of Silicon Valley. verge has hosted more than 1000 entrepreneurs to pitch their companies at our events around the world in cities like Indianapolis, Indiana, Kansas City, Missouri and Nashville, Tennessee. Those founders have gone on to raise more than $500 million in capital collectively, and are disrupting industries creating wealth and changing the world. These are their stories. And if you haven’t subscribed to powderkeg yet, it’s not too late. You can subscribe wherever you listen to your podcasts. We’re on SoundCloud, Stitcher, overcast iTunes, Google Play all the major outlets and you can find all of the links to subscribe as well as show notes and transcripts at our website powderkeg.com. So that’s powderkeg all one word.com If you haven’t iTunes account, we created a handy link for you at powderkeg.com/itunes which is going to take you directly to our show where you can subscribe leave a review and see all of the awesome episodes from past guests like Brian Clark at Rainmaker, based in Boulder, Colorado, Karen Norman, upfront ventures in Los Angeles, California, and Max Yoder at lessonly. In Indianapolis, Indiana, it’s your subscribes and reviews that help us reach more people and share these founders stories from beyond Silicon Valley. So again, that’s powder keg.com/itunes. Back to the show. So Tim, one of my favorite quotes that I’ve heard you say, time and time again, is just because you’re in b2b, or business to business doesn’t give you a license to suck at marketing.

Yes, I have been known to say that.

I love that. Why, why? Why is that one of your most repeated mantras,

because b2b marketing socks I mean, seriously, that’s kind of the truth. People are people. And even if you’re marketing to a business, last I checked, like, you know, the actual building doesn’t buy a piece of software, it’s a person in that building that you broke build a relationship with. So it’s still B to C. So to me, it’s kind of B to B to C, or something I call B to H now, which is just business to human. But I do believe that. And I think part of the problem was, I think many of the most successful marketers in b2b today did not grow up in b2b marketing. They grew up in either b2c or came at it from the product side or different part of the organization. So and now, I think the marketing you’re finding is incredibly inspired, I think in some ways might be passing b2c,

I would absolutely agree with you, it’s been really cool to see and what you were able to accomplish, I didn’t see your work as closely at Webtrends, as I did at exact target. So I’ll probably hone in on that a little bit more with my questioning here. But, you know, the thing that you continue to repeat to me when you were helping grow that business was that brand is a leading indicator, or culture is a leading indicator of brand, rather. And then the other piece of advice that you continually reiterated is, you know, get your messaging and positioning

and what you do and why you’re different. How is anybody else in the company supposed to know? And if they don’t know how your customers supposed to know? And if you’re not being very clear on what problems you solve, and what things make you different? How do you even do demand generation, like, because you don’t even know who you’re supposed to be marketing to, and what what your message is. So, one, it gets rid of when you sometimes you just see a company, if you know what I mean? Matt is like a little like they’re having an identity crisis. And they’re like, just flip flopping around on who their brand is or what they stand for, and like, what is going on. And I think it’s because they’re so obsessed with the creative, and they’re not getting what they want. They’re just flipping agencies. But the messaging to me, if you think of an iceberg, and that metaphor, the messaging and positioning is all the work that sits under, you know, kind of the water level, and sometimes what you don’t see, and it’s just kind of the branding, then or the visualization that pops out on the top. But it is, if you don’t have that foundation, it’s really hard to have a clear visual identity. So one, it just drives focus, I think discipline as a company, but it makes everything else you do so much better. The reason people don’t spend time on it is it’s hard. It’s really, really hard

positioning piece is so difficult, because as a founder or as a CMO, or marketing lead you it is easy to flip flop, right. And I think one of the best things you can do is, is just make a decision and stick to it and be consistent. But how do you how did you go through that decision making process? When picking what the final positioning and messaging would be like? What are some of the important things to consider?

Yeah, and boy, I’ll be honest, I’m still working through this every day. I think it was a learning on how to get better at messaging and positioning. And the first thing I found and sorry for any of the agency folks on the phone, I don’t think messaging and positioning as an outsourced bubble item, I believe it is so core to your strategy and who you are, it would be like trying to hire like a consultant or a designer to like create my life plan. I just, nobody knows you better than you. So how am I how you outsource that. And so one of the first mistakes I see is letting somebody else do it. And I think it’s just the hard work that you need to go do. And then the second part of this, there’s just a lot of consensus building and an alignment kind of internally. And it’s just, it’s got to be something really driven from the CEO. So in this case, Scott was really passionate about it. I think, at the end of the day, this has got to be a lot of founder DNA really has to just who’s into this process, but it’s also if it’s a quote unquote marketing thing, it won’t work. I mean, you have the privilege of leading this on behalf of the entire company. So Have you need to go and speak to people in product and in sales and be out on the front line and talking to customers, and you just have to be thoroughly immersed in the whole process and all the key leaders in the process and get buy in from everybody. So people can, you know, that word or this thing I did that or I helped contribute to this. In the end, people feel kind of a part of it more than like, here’s our messaging card and the marketing team deploying it to you. And because we’re giving you this, like, laminated sheet, you should now know what all of our messaging.

Absolutely. Well. And Scott, of course, you’re referring to Scott Dorsey, co founder and former CEO of ExactTarget. Yes, thank you. Yes. Yeah, of course. No, no, I, when you say, Scott, I know who you’re talking about. Yeah. But just just in case, we don’t have Indianapolis.

Target. There are lots of scouts. But yeah. Matt’s got Dorsey. Yeah,

very true. And I’m sure you’ve worked very closely with him on the messaging and positioning when you got there to exact target. That must have been an awesome experience working that closely. With Scott, can you maybe share some of the experiences there when you were first diving in and rolling up your sleeves? That exact target?

Yeah, you know, so the first thing is, a lot of people realize what exact target was at the end, but may not have realized the journey of kind of where it came from. I mean, when I arrived, I think there was seven or eight people on the marketing team, it was a tremendous selling organization. So honestly, if you think about sales, and marketing is interconnected gears, the sales gear and just rip the teeth off the marketing gear. They were so overbill relative to marketing, and we had so much work to do, Matt, it was I remember, the first thing was, I just think, oh, my gosh, he’s putting they’re not being set up for success. Because I, I went around and asked everybody, what, what are the most important things we should focus on? And after I got that list of 26, things like when the analyst report and redo the website and increase our leads by 3x, and build out the culture, and can you do messaging and positioning? And I was like, wow, there’s, there’s a lot here, and welcome to the modern CMO. So the first thing was the best marketers, I believe, are ruthless, prioritize errs. And a lot of it was just constantly gathering requirements on what what it was that people thought look like success explaining to them that they’ve been heard, here’s the whole list of things. But these are the things that we need to go do first, and you’ve kind of got to gotta trust me on that. And I remember Scott and I initially just having lots and lots of prioritization discussions on you know, what things fit in, where how do we make different things a priority. And fortunately, he has a, just a love and a passion for go to market and marketing and customers and was willing to kind of make that investment and, you know, personally get involved in a lot of these things. And I think that’s what I think it’s authenticity, which is kind of an overused word now, but I don’t know what else to use. It’s gone. I think I’ve always used but I think what really made the exact target brand and messaging stick out was just the authenticity of it. And it really, it came from Scott, it came from the leadership team, and then it just sort of worked its way all the way through.

And is that what you ended up prioritizing their exact target net number one spot is getting that messaging, right, Matt, I’d

like to say it was. The reality is, I think, Mark, in some ways, nothing else matters that accompany more than sales. And I think if you a lot of what you’ve got to do as a new leader is build credibility, and and get some quick wins. So if I want to wait to a conference room for 90 days and just said guys, just go off and build our messaging, I that would have been tough. And theoretically, it was the right thing to do practically, I don’t think you could do that. We just had a lot of work to do to build credibility with the sales team. So I remember running around all their regional meetings, lots of individual sales deals, jumping in and helping wherever I could. Turned out, that was the best thing I could have done, because I wasn’t going on some kind of, you know, like cheesy, like 90 day listening tour or something like that. But it was all the context I got from meeting like all of our salespeople, and so many leaders that I think then Then help me better do some of the messaging and positioning. So honestly, it was building a lot of engagement and hopefully trust with the sales team that kind of gave you the I don’t know, sort of the political capital, if you will, to go off and work on things like messaging and branding.

Wow, that’s that’s just a great lesson in and of itself. And there’s a lot more I could dive in on just we’ve had hours of conversations about how to build your marketing dashboard and what metrics to focus in on and we’re all gonna have to probably save that for another episode because I I really want to better understand your transition, you know, of course ExactTarget IPO and then subsequently being acquired by Salesforce for $2.5 billion. It’s made a massive impact in Indianapolis and the entire SAS ecosystem. system. And you’re now investing, you’ve invested privately in companies and then join the teams with Hyde Park ventures based out of Chicago initially, but now leading the Indianapolis office. Why was that your next step after after that acquisition?

Yeah, it took me a while to figure it out. To be honest with you, Matt, I kind of like if the first 10 years of my career was sort of the CPG, digital marketing bucket of things. And then the next 10 years were kind of SAS, sort of b2b cmo, it was a bit of like, where I was being recruited and naturally polled was to well, one either stay at Salesforce or to go and do that for another company. And right or wrong, probably one of the things that you know, is coming out, that you’re figuring out about me just through this conversation, is, probably once something starts to be fairly easy, I should just stick with it. Like, the easiest thing to do would have gone to be come another, join another pre IPO b2b SaaS company and go do it again. But I’ve got this sort of internal push or instinct to go write a new playbook to go and do something else. And one of the things that we experienced during our journey and exact target was just how difficult it was to raise capital as a as a midwestern company became a lot easier as we went, but at the early stages really tough. And so it first started off is the desire to just help other earlier stage companies and entrepreneurs at that point, you know, after running hard for a bunch of years, not not in a way that it was doing it, you know, at a sort of 80 hour week pace, but how can you just get involved and, and help and at least that people are gonna make mistakes, help them make different mistakes. And so it was jumping in and making investments or helping with messaging and positioning, sort of doing whatever you could and I really enjoyed it found it personally rewarding, but also found being a person of one that doesn’t, it doesn’t scale well, doesn’t scale well at all, both financially or in terms of your time. And so I ended up doing literally, five deals with this group called Hyde Park ventures out of Chicago in a period of six months. And so we met with one another and just realized, boy, we like to look at the same deals. And after a period of time, it became clear to them that they’d like to raise a second fund, and they would like me to join for that second fund. And it just became kind of natural thing on both sides.

What was the biggest lesson you’ve learned so far, in your transition into that venture capitalist role

that it is hard, much harder than I would have thought? Like, it’s as hard as being an operator, but in a very different way. Entrepreneurs and operators are doing all the hard work kind of day in and day out in the trenches, Birdman, being a VC, you kind of get, I don’t know, like, you kind of get this impression, it’s sort of what you do is you write checks, and you show up at board meetings once a quarter. And it’s just not true. There’s just a lot of work that goes into to doing that work really well. So I think that was the first thing just how tough it was. The second thing, if I do sort of confess, things that I struggle with, it was like, I don’t run these companies anymore, I’m not the operator. So it’s my job to kind of point out things that I’m saying, or potential issues, but realize at the end of the day, you’re you’re handing this off to somebody else to go solve it, that’s just different. You know, you’re not being helpful as an investor, if you’re jumping in and overriding the management team. So your your guide has to be starts to transition a bit more and like being a coach instead of a player.

Either there any books that you’ve read that have been particularly helpful in that coach role, and they don’t necessarily even have to be venture capital related books that you know, maybe maybe more of some of the leadership books that you’ve read along along the way?

Well, I mean, there’s just some great one, I mean, that, like just things like a degree to me that are kind of timeless. And to me, what you do find is, they talk about this elusive thing and venture called pattern recognition. And I thought that was a silly concept. But gosh, I get it now. And so you can start to understand when, you know, you can almost ask a company. Boy, I bet you’re having a slow quarter. Yeah, well, how do you know that because I work with eight other companies, and they work in the same space. And it’s been tough the last couple months, or when you realize that companies sort of hit these net, it’s hard to get to a million dollars, and then that kind of three to five, and then to 10, and then to 25. So what are these natural glass ceilings, just things that present themselves over and over? So what you’re able to do is at least I think it’s the difference, you know, having played football before this, it’s the same game, whether you’re on the field or in the stands, but your vantage point being in the stands is so different than what it is on the field, and you just see things in a different way. So you’re able to coach more from from a macro perspective, and I always wondered how are our board members able to ask such smart question and it’s been drilling on something just fast. And I think it’s just because they were watching the game. And a lot of times they played the game before, and now they’re watching it. And so you get this really different perspective. And a lot of man, I wish there was a book a lot of it was just from, we had a amazing board of directors at at, and a lot of it was watching and learning from from from those days.

Well, I think there’s a lot we could dig into deeper here. But I would love to say that for a future conversation, hopefully get you back on the show here, Tim, if people want to find more of your writing and thoughts on SAS and leadership, where can they go? How can they find more about you and what you’re doing?

Sure. So I never thought I would become a writer or have my own website. But what I found is there’s not a playbook for a lot of these things. There’s that playbook word again, what once I was asked a question more than three times, I figured it was probably time to sit down and write an article on it, or just one, it became a more efficient way to kind of scale my time. But it also kind of forced me to be better in terms of like really crystallizing my thoughts and being more precise and clear on how to go and do things. But less from a macro thought leadership standpoint more from a in the trenches, what do I actually go do standpoint is what I’ve tried to look at. And so we’ve created this website, and it’s just called cmo VC, like chief marketing officer vc.com. Yeah, you know, we’re not nearly as far along as your map. But we’ve got, you know, eight or 10,000 folks who have signed up, which I still, you know, I can’t believe and I’m grateful for but just use that as a chance to talk about everything from leadership to venture capital to sales and marketing metrics and everything in between.

It’s so awesome to have access to your knowledge there, Tim, you know, even knowing that I can send you an email or pick up the phone and call you and knowing that you’ll respond is awesome. But having it all there written down to just dive into and read as you publish it or as needed when I’m struggling with a particular marketing tech issue. I always think oh, you know, before email, Tim, maybe I should just check his blog and see if he’s already written about this. And so 90% of the time you have, so I cannot recommend that enough. And obviously, Tim is on Twitter as well. We’ll have all of your stuff linked up in the show notes on powderkeg.com, including that Mentos video that you did with Coca Cola.

Absolutely.

But thank you, Tim, so much for being on the show. And I hope to see you at a verge of powderkeg event here soon. Yeah,

absolutely. Thanks for having me.

You bet. That’s it for our interview with Tim cop, but it does not have to be the end of the conversation. You can find him on Twitter at T B cop. That’s AT T B cop and he’s very active on Twitter. Also, of course, make sure you check out cmovc.com That cmo like Chief Marketing Officer VC like venture capitalist.com He has so many so many good insights and lessons learned there that he’s captured in really easy to read fun to read blog posts, so make sure you check that out. And if you liked this interview, you might enjoy episode 12 which was with Rodney Williams, who also made the transition from corporate to start up, he was actually a Procter and Gamble employee as well and made that transition that leap into the technology world into the startup world from his corporate background. That’s episode 12. Again, with Rodney Williams, who’s the founder of listener, you might also really enjoy episode 30 That is powder keg episode 30 with Dave Knox, who’s the co founder of Bradberry accelerator program in Cincinnati, who Tim actually worked with they’re at the grand jury. Dave also worked at Procter and Gamble before diving into the startup world. I don’t know there must be some kind of trend here where Procter and Gamble is just churning out the next generation of startup entrepreneurs. But that is a really interesting conversation. And Dave dives into not only that transition from corporate to startup, but talks about how to cooperate and compete with large companies as a startup. Really interesting conversation there, so make sure you check out episode 30 with Dave Knox