Innovation, Timing, and Leadership Whether You're an Entrepreneur or Intrapreneur

Louis Gump joins us in the Sky Lounge to explore a question every founder and executive faces eventually: what happens after the acquisition? In this candid conversation, Louis shares how he helped build the mobile businesses at CNN and The Weather Channel, and became the steady hand guiding post-acquisition innovation at startups and growth-stage companies alike.

We unpack the differences between entrepreneurs and intrapreneurs, what makes someone thrive inside a big company post-acquisition, and how timing and self-awareness shape every meaningful career move. Louis also discusses the importance of clarity in strategy, the value of not rushing change, and why keeping founders involved after a deal often leads to better outcomes.

Louis is also the author of The Inside Innovator, a practical guide to driving innovation from within established companies — ideal for leaders navigating post-acquisition roles or scaling without the founder title.

Whether you’re scaling, selling, or staying to build the next chapter — this episode will meet you at the crossroads.

TAKEAWAYS

  • Louis Gump focuses on helping companies with fractional CEO and COO assistance.
  • Innovation is crucial in both startups and established companies.
  • Leadership is about empowering teams and fostering collaboration.
  • The Weather Channel’s evolution highlights the importance of adapting to change.
  • Founders play a vital role in maintaining a company’s innovative spirit.
  • Transitioning from entrepreneur to intrapreneur requires a mindset shift.
  • Successful teams value contributions from all members, not just leaders.
  • Self-knowledge is key for effective leadership and team dynamics.
  • Community engagement can drive significant local development and opportunities.
  • Understanding company culture is essential for fostering innovation.

ABOUT OUR GUEST

Partner in the Executive Operations Practice of TechCXO
Author of “The Inside Innovator: A Practical Guide to Intrapreneurship” available at booksellers and here: https://louisgump.com/

Experienced executive with a demonstrated track record of success in the media industry on multiple platforms. Skilled in Digital Strategy, Innovation, Local Media, Multiplatform Content and Advertising, Connected TV, Mobile Media and Marketing, Management, and Mergers & Acquisitions (M&A). Strong business development professional with an MBA focused on General Management and Leadership.

"…if innovation stops, flat-out negligence on the part of the acquirer, that's just losing an opportunity. And, you know, you've got to ask yourself why the acquisition happened in the first place."

LOUIS'S TALES FROM THE SKY LOUNGE

Todd Merrill:

Hi, welcome to Tales from the SkyLounge. It’s a podcast about business, consulting, and venture investing. We get out there in the world, we talk to people who are making it happen, and we get their stories.

Today’s guest in the SkyLounge, Louis Gump. Hey, Louis.

 

Louis Gump:

Hey, Todd. Great to see you.

 

Todd Merrill:

Yeah. Great to see you. Hey, Louis, who are you and what are you working on?

 

Louis Gump:

Well, first, thanks for having me on the show. And at this point, I focus on helping companies that need fractional CEO and COO assistance, and I help them operate the companies, to coach up their leaders, and to innovate from within.

 

Todd Merrill:

Oh, wow! Everybody needs that stuff. So, a lot of good stuff. And I know we’re going to have a great conversation today, especially, I see your book right behind you, which is a Guerrilla Marketing Tactic. Love it. And then, are those other books below it your favorite books, or did you write those too through the years?

 

Louis Gump:

I have written one book. Thanks for asking. Those are some of my favorites. One of them is Great by Choice, which is one of the less appreciated books by Jim Collins compared to Good to Great and Built to Last. And then there’s one called UnStuck by Stephanie Stuckey about reviving the Stuckey’s brand. There’s one on The Weather Channel, which is a story that I know large portions of very well. There’s one called Call Me Ted, and it is about Ted Turner’s journey, just an amazing story of, you know, a legendary leader. And then I think the one on the bottom is Amazon Unbound about the growth of Amazon. One of the most interesting things for someone like me who admires people who find new ways to grow is that Amazon has just, you know, had repeated instances of doing that really well.

 

Todd Merrill:

So, my favorite Ted Turner quote. You know, his history, I grew up around Atlanta, so he’s a legend, but I think his dad died early and had a couple of billboards, and that’s how he got his start in advertising, right? So, his famous quote is, Hey, Ted, what’s the secret to success? He’s like, early to bed, early to rise, work like hell, and advertise. So, anyway, but you worked at CNN for a minute, right? And I know there’s some incredible talent there for a while. Why don’t you tell us about … did you ever get to meet Ted? I know he’s a kind of legendary figure, but what was CNN like working there?

 

Louis Gump:

So, I never met Ted. I did work with a lot of people who worked closely with him, and it was just this extraordinary place to work, especially at the time, very dedicated to bringing people the news that mattered, with the, you know, arguably the largest news gathering team in the world. And it was very creative with a bunch of people who were just smart, and they wanted to do their jobs really, really well, some of the best journalists I’ve ever met. And one of the things that we found is that not only was it CNN, but it was within the larger Turner Broadcasting Company, right? You had TBS and you had Turner Classic Movies, and this was more on the news and information side, obviously.

In addition to that, there was entertainment, so you had this cross-pollination of people who had different strengths, different interests, and it was just a really vibrant time.

In my case, I arrived as CNN.com, the desktop site was very prominent and successful, and we needed to build the mobile business. And the company had decided we were going to get serious about that, and we kind of wrote a new strategy, built a team, and looked at ways to complement the broader brand. So, it was a really incredible opportunity to simultaneously build a business while strengthening the broader company.

 

Todd Merrill:

Mm-hmm. And some of the best engineers I’ve ever worked with, especially in the web space, had Turner on their resume out of Atlanta.

 

Louis Gump:

Yes

 

Todd Merrill:

I mean, really, really talented team.

 

Louis Gump:

You know, it’s interesting that it happens that way, and I think this is true with other great companies, too. At the time, we knew we had something special. I can tell you now, around 15 years after the time that I worked there, I’m still running into people all over the place who were meaningful contributors at Turner, and now they’re the experts where they are. It was like a training ground for the best and the brightest.

 

Todd Merrill:

Yeah, and that’s actually how I got on LinkedIn. I was at Sienna for the telecom bust, and then everybody, it’s kind of like today, everybody was laying off 10, 5% in the rolling waves, and then we all got eventually laid off. And then one of the companies that we had acquired out in the Bay Area, California, was somebody knew somebody, and there’s this screwy little startup called LinkedIn. Hey, like, everybody, LinkedIn, and then it was like, okay, this is kind of weird, but it’s all good. And then that was like the best thing that … sometimes that’s the best thing that can happen to you is to be a part of a really good nucleus of people, and then have it explode, and then the seeds scatter to the wind. And now, five years later, 10 years, 20 years later, you’ve got really amazing contacts and really amazing companies. But anyway, I think Turner’s kind of like that. So, you all did some really innovative work there, foundational pioneering work. That’s back when the web was kind of new, and everybody was figuring stuff out. So, I guess that’s one, the theme here is innovation, right? You wrote the book on all kinds of stuff. That’s one mode of innovation, right? When it’s all brand new, and everybody’s going like hell, and gets it, figured out, and there’s a lot of money in a big company. That’s a great mode to operate in, right? Did you learn any lessons from that for later? Or how do you compare and contrast it to other innovation cultures that you’ve been in?

 

Louis Gump:

There were a lot of lessons there. One of my favorite stories actually came after the fact when I was interviewing people for the book, and I spoke with Bill Burke, who was the first leader of Turner Classic Movies. And he shared a story with me. He said, Louis, I was hired, and I was getting a tour of the old Turner building right at around 10th and 14th Street here in Atlanta. And as he was walking through, the person who was leading the tour said, and that’s an office for our next business. And it was empty. And Bill said, “Well, what business is that going to be?” And the answer was, we don’t know, but it’s coming before too long. And sure enough, it was as Bill helped them to build businesses. So, it’s this idea that there’s opportunity out there along the way, even when you don’t know exactly what the answer is at the moment. Another thing for me at CNN was how important an extended team can be. For example, we were coming in. I was new to CNN, having had some great experiences at the Weather Channel. And I didn’t know a lot of the people that we were depending on for our success. But on the other hand, I was paired up with a technology leader who had been with the company for years. He knew virtually everybody, and he knew how to get things done. And I knew a lot about the mobile space. And so when we fused our respective expertise along with other people, we just grew something impressive in a relatively short period of time. And my boss was extremely supportive of what we were doing. But other people around the organization were, too.

Another one that I remember was from Jim Walton, who was the CEO of CNN for years, including all the time or most of the time that I was there. And we had a meeting with Jim when we were looking at a new way to develop an app for the iPad. And some people took the point of view that we should just deploy a version of the desktop CNN.com. And some people took the position that we should build a new experience that was customized for the tablet. You can probably guess where I landed on that one, which was, I thought, if we were going to superserve our customers, we really needed to think about this different platform. So, we put together a presentation. Our approach to create something custom was going to cost much, much more than a simple kind of translation of CNN.com. We went in to talk with Jim about it. And we had several leaders who were kind of unified on this approach. And we talked with Jim for a while. He listened closely. He was paying attention. And then at the end of it, he said, you know what? And I’m paraphrasing here. He said, this isn’t something that I’m used to this format. But do you believe in it? And he went around the room, and each of us, including me said, yes, we believe in it. I think this is important. It’s best for CNN. He said, “Well, I might not do it this way, but you’re the experts. So, go get it done.” And that was a real lesson in leadership for me.

 

Todd Merrill:

Disagree and commit, even if you’re the boss, right? Wow, that’s pretty rare, right? You know, you see a lot of people who are in those really powerful positions that just know the way it’s supposed to go, and they just follow me and let’s go. But I think it’s more powerful when you have a great team, you trust them, and you say, hey, get it done. You know, let’s go.

 

Louis Gump:

That’s right.

 

Todd Merrill:

I mean, that’s kind of cool. I mean, you don’t run into that mentality that much. And he’s obviously very successful, right? And it, you know, built a global brand, and it’s not many people get to do that. Pretty cool. And you mentioned Weather Channel. So, were you there before or after IBM bought them?

 

Louis Gump:

I was there before IBM bought them. And the timing on that is that the Batten family started it, in particular with Frank Batten, Sr., and several other people, Bond Stanley, Rusty Friedle, a number of people who were involved around 1980. And the company grew as the Weather Channel Network for years. And then around 1995, somebody in the organization said, hey, I think we need an email address. And there’s this dot com thing that I wasn’t there at the time, but I’ve heard the story, and it’s reliable. I think we need an email address. What do you think about Weather.com? And so it started as an email address, and then kind of grew from there and websites grew. And so Weather.com was literally started as a website in 1995. And I was there on the 10th anniversary. I still have the T-shirt, I think. And so fast-forward a little bit. I arrived in 2001 and still the Batten family owned it. And we saw the TV network continue to be highly trusted and used. Weather.com for desktop grew rapidly, and we incubated a mobile business that turned out within a few years to drive a significant portion of the value of the business, which was helpful when we got to 2008 and the family decided to sell it. And so the first sale was to NBC, Bain, and Blackstone in September of 2008. And then I think I’d have to go back and check the timing because I went to CNN in 2009. But in around 2014, I believe the business was sold, the digital and B2B business was sold to IBM. And later on, the TV network was sold to Allen Media.

 

Todd Merrill:

Okay. And it’s, boy, it’s, you know, going back a long time, you know, when you had to flip to channel 13 or 12 or whatever it was to get the weather on TV. Right? And then, boy, you know, Weather Channel, when is the last time you even turned on the TV to get to weather? Right? It’s on your phone. It’s ubiquitous. It’s everywhere. Why would you do that?

 

Louis Gump:

That’s right.

 

Todd Merrill:

Yeah

 

Louis Gump:

Yeah. Viewing patterns have really changed. And I know a lot of people who have been in the thick of not only the evolution of brands like the Weather Channel and CNN and ESPN, but also trying to understand and anticipate the needs of customers as the capabilities and the devices have changed.

 

Todd Merrill:

Yeah, it’s tough. You know, I think what I’ve figured out is that technology is just a series of waves. Some of them are little, tiny, fast waves, and some of them are ginormous, you know, tsunami waves. And you’re going to see all of the different kinds of waves in your life. So, it’s kind of about knowing when to hop on and off. Yeah. I don’t know how you feel about that, but, you know, every company, no matter how long you’ve been around, seems to always have to reinvent itself at great, you know, more and more frequent cycles. And that’s, you know, innovate or die. We’ve all heard that kind of phrase over the years. But yeah, so Weather Channel seems to have done that, right? Do you feel like it’s because, you know, if it’s family-run and you have the founders still around, founder-led or founder-adjacent leadership, do you feel like those are the kind of people that still have the kind of DNA of, hey, you know, we started this thing. Why not? Let’s go do something else. Do you feel like that’s a big part of the secret to innovation in larger companies is having that DNA around?

 

Louis Gump:

I think having founder DNA or that mindset is valuable. It’s hard to come up with a one-size-fits-all approach. I think in some respects, the Weather Channel would have been very well served by continuing to be guided by such a principled company as Landmark was, the parent company of the Weather Channel that was owned by the Battens. And at the same time, one of the things that happened was that the industry changed too, so it wasn’t just the technology. It was also a situation where you kind of needed to be part of a bigger group to maintain relevance and to innovate, for the most part. And so that’s how you saw, you know, Turner Broadcasting become part of larger organizations and eventually turn into, let’s say, Warner Brothers Discovery and the next iteration, which is currently in the news. So, coming back to your questions, I think it’s really helpful to have founders involved, and if and when they think it’s time for them to focus on their next adventure, then finding people who sustained that concept of stewardship for a brand and innovation, those are two pretty important aspects to bring along with a great team.

 

Todd Merrill:

So, I talked to people and even on this podcast, you know, we interviewed founders who ran, you know, founded something, their name was on the T-shirt, and the domain name and you ran it for 20, 25 years and they sell it to private equity or whoever’s next or whatever, you know, a great, great run. And then that’s an emotional, like, for the founders, that’s their identity. Oh crap, you know, I’ve got to realize that I’m not a part of that anymore. I don’t even have an email address in some cases. But now it’s somebody else’s baby, and there’s definitely a different change in leadership. And then that next owner probably either is going to absorb you into a different culture because you’re a valuable puzzle piece to something bigger, or maybe they’re going to optimize you. The MBAs get ahold of you, but it’s a different necessary mentality of management. You know, how do you think about that? Is that when innovation stops, or how do we think about, you know. You have this founder that that’s done so well and kind of got a company up to steady state and productive, and it sells out for a variety of reasons. Maybe it’s cause they couldn’t get past a certain, you know, ARR, maybe it’s cause they just kind of like running it small, family-owned for a little bit, maybe it’s because it’s just time. They’re sick of it. But inevitably, somebody else with a different management philosophy, good, bad, or ugly, takes over. What have you seen happen in those cases to innovation in general?

 

Louis Gump:

There’s such a wide range of outcomes there. For starters, this is a very common situation where a company that’s run by a founder or a group of talented earlier-stage leaders, you know, they become part of a larger organization.  In direct answer to your question, if innovation stops, flat-out negligence on the part of the acquirer, that’s just losing an opportunity. And, you know, you’ve got to ask yourself why the acquisition happened in the first place. On the other hand, if what’s happening is you take some of the best things of the company that’s been acquired, and then you add on some of the best things of the acquiring company, and you continue to innovate, that’s when you can magnify success and tap into the true potential. So, as you can imagine, I’m an advocate for the latter.And another thing that’s important to understand for founders, I have this conversation all the time. I just had a two posts on it over the last couple of weeks on LinkedIn, because it’s so common. And that is an entrepreneur who stays with the company after a deal. And I know not everybody does, but if an entrepreneur does that, they need to understand that they’re shifting from being an entrepreneur to an entrepreneur. And if they miss that memo, then they’re going to have a lot of problems because you try to act exactly like an entrepreneur within a much larger company, you’re going to make it about three seconds, the company is going to say, ah, we don’t like this too much. Or the founder is going to say, this is driving me crazy or both. And so preparing…

 

Todd Merrill:

… I hear that a lot, by the way. Yeah.

 

Louis Gump:

You know, it happens all the time. And on the other hand, when founders do make this shift, they understand not only the mindset change, but also the process differences and the actions to take a bit differently. The founders can work some serious magic. Some of them go on to have a remarkable and broader responsibility within the acquiring company because they bring the best of being an entrepreneur, and yet at the same time, they know how to adapt. So, in most cases, the story is not written before the acquisition takes place. And there’s a lot of room to create your future after the acquisition.

 

Todd Merrill:

All right. Well, let’s drill down on this because this is something that’s vexing to me. And it, you know, as a founder entrepreneur, it’s like, why the heck would you stick around in that big, dumb corporation, but they’re not all big and dumb. Sometimes you get access to resources, you have a support team, oh my God, you can go a lot faster if that’s appropriate. Sometimes it’s not. What is that mind shifter? Can you tell us an example? I don’t know if you’ve been on that acquisition side of that transaction where you have a great leader that you want to keep in place and you were able to retain, but re-task with something interesting. You can’t just have them, you know, manage the P&L. Like the quarterly budget, right? That’s not going to, you got to give them some meat to go after, you know. What does that look like in a successful cause I’ve seen a lot of people go, eh, I’ll earn out, but I’m not going to be excited about it. And that’s it. Yeah. But what does it look like when you catch fire and you make that jump over into the next level?

 

Louis Gump:

Well, what it looks like is that the prior owner who has sold still has a lot of commitment to the brand and is able to subordinate their ego to the needs of the broader organization. So, the point that you raised earlier about identity, still identify with having started it, but recognize now you’ve got a broader team that’s responsible for the success. I’ve seen this work really well, several times. I’ve been involved both on the acquiring side and also on the being acquired or kind of being part of an acquisition side.

One of the best ways to make this work is when you have somebody or a couple of somebodies who are your advocates and guides within the acquiring company, what I call a Sherpa. Somebody who can essentially show you around, make the introductions, advocate when you’re not in the room, that sort of thing. Although I’ve been part of a number of acquisitions, one that comes to mind that I’m aware of is Bleacher Report, when Turner acquired Bleacher Report, and that has been very successful for Bleacher Report, and I know the founders made a really big difference within Turner Broadcasting. At the same time, we had this group of experts within Turner who helped the founders achieve their dreams.

 

Todd Merrill:

Okay. Tell me about that story. Like, let’s drill down on that a little bit.

 

Louis Gump:

Yeah, absolutely. And one of my favorite stories from that, it came up when I was doing research for the Inside Innovator, and I was talking with Lesley Wainwright, who was a lawyer within Turner, and she was on the acquiring team, helping with post-merger integration, and she started learning more about the business, and then she was more valuable than just her legal guidance, and as Turner saw this, she became more valuable in a variety of parts of the business. She eventually became very senior within Turner and went on to become general counsel of play on sports, for example.

 

Todd Merrill:

Oh, yeah. I know them. Yeah.

 

Louis Gump:

So, these sorts of acquisitions are not only opportunities for founders, if they want to stay, and they don’t have to. There’s not a right answer here. It’s, you know, whatever’s best for the person, but for the founders who want to stay, there’s great opportunity to actually achieve even more of their dreams with the additional resources that you refer to, and it’s also an amazing opportunity for people who are already part of the broader organization to grow and to take some of your best and brightest and essentially to groom your next generation of leaders.

 

Todd Merrill:

Hmm. Okay. Yeah. I mean, something to think about. So, I’ve got this book, and we talked about this at dinner. It’s Accidental Empires. How the boys of Silicon Valley did all these great things and can’t get a date. It was some kind of clever subtitle. So, they studied a lot of the early tech companies, Microsoft, Oracle, you know, Sun, Cisco, I think, was in there. And then they said, hey, you know, what defines success and what all these people have in common. They did a lot of research. And then I think there’s been some follow-on books, but you know, one of the things that stuck with me was, hey, when you’re starting, right, there are three very distinct quantum phases of development there. And it’s like an army, right? You have commandos, an army of invasion, and the army of occupation. You won the war; take the bullets out of the gun. By God, don’t do anything to screw it up. Right? 

And then their research was that everybody really falls very neatly into one of these three buckets, with a very, very rare exception of people that can shift from one to two, or two to three, right? And then those are your leaders. And if you’re a growth environment, you need to kind of recognize that there are special circumstances that you need to look for and pull that out and make them in charge of stuff. Like for me, personally, that resonated. And I said, hey, you know, I’m a commando coder, so I love to code early. And then shift gears. And then I’m a very good operator when it gets a little bigger. Right? And then I don’t want to code anymore in a bigger environment. I’m more of a people leader in a bigger company. And then when it gets to like, don’t do anything without having three meetings about the policy. Like, no, thank you. I don’t want to be there. Right? And then so to kind of over, I believe that that’s true, but I think there’s another nugget here somewhere. So, that book specifically said intrapreneurs always fail. That’s stupid, which clearly is not true, but clearly, there’s some headwinds, right? So, if you make it to the army of occupation, you’ve won. There are a lot of antibodies against doing anything new and different, and disruptive. Like, you don’t want to disrupt a good thing. How do you, I know you got thoughts on that. So, it sounds like in the companies you, you know, examples you’ve been in, they didn’t quite make it to the end of that evolution. There’s still a shooting war. There are still friendlies around that understand innovation. Maybe that’s where we are. Right? And so how does one, what do you say to that? And then, how do you innovate in a large established company that has all these resources, that is a great place to innovate, if you can get the green light? What does that look like?

 

Louis Gump:

Yeah. So, I’ll first go to this distinction among three types of people, and then go a little bit to what it takes to innovate within larger companies, especially as someone who’s done both and had the privilege of working with amazing people who are most naturally wired to kind of succeed at these various stages. There are some people who are so naturally suited for entrepreneurship that if they see anything beyond about a 15-person company, and somebody who asked them to go to a meeting, then it drives them crazy. And on the other hand, there’s some people who shudder at the thought of having the risk of a large portion of the company on their shoulder. What they want is to be part of a much larger organization and they never want to be part of an early-stage business. And then there are a lot of people that are in the middle. So, I think Accidental Empires, I haven’t read it yet. I want to, but this construct that you described I think from the way I understand it now and reserving the right to update this after getting more familiar, I think when they underestimate is the middle. My research and my experience indicate that actually there’s a sizable group of people who can go back and forth. These days I talked with a lot of college students and, you know, there’s discussion about being an entrepreneur and there’s all sorts of good things about being entrepreneurs. I don’t pick one or the other, and I don’t judge either. But what I can say with high confidence is that the skills and the approaches that are needed to be an entrepreneur are a lot different than the ones needed to be a successful entrepreneur.

 

Todd Merrill:

Okay. Interesting.

 

Louis Gump:

You know, timing matters. And for example, if you have somebody who’s closer to the middle, then you can say, hey, maybe you wanted to start that software company when you’re just out of school. Maybe you wanted to start the lawn mowing company. Maybe you wanted to start the marketing company, the coffee shop, you know, you name it. But maybe you have student loans, and maybe you want to learn from people who have been there and done that. For a person who has those sorts of interests, they maybe want to get a little financial stability, learn from great mentors, and that sort of thing, and have a higher probability of success. Maybe you want to go work within a larger company first. On the other hand, a person at the same stage might say, hey, someday I have more obligations. I have fewer obligations right now. I have a big idea. I want to go get it done. The cost of failure or the risk involved is acceptable. Maybe it’s a great time to go become an entrepreneur.

Where I get more concerned is when people assume that the only path to being successful in terms of fulfillment, in terms of contribution, in terms of finances is when you buy into this myth that if you go start a business, you’re just going to turn into Mark Zuckerberg or Sara Blakely. Right? Most people find it doesn’t happen that way. And so I think it’s great to learn from and to consider entrepreneurship. But I think also a lot of people have amazing careers starting in a midsize to large company and then later on finding their way into entrepreneurship. I know many CEOs who have taken that path. And so I think we’re being a little narrow in definitions. If we just say, well, you’re kind of one or the other, and then there’s a judgment attached.

 

Todd Merrill:

So, it’s not so black and white, and maybe the model is better at the early stage than the later stage. And I believe that’s true, right? And you have people who would take a risk that would be talented at building things. There are builders everywhere. And then, you know, pick a big company these days, right? If they’re not building, they’re dying. And then, so even in very, very large, very well-established companies, there are still new projects. You still have to find the people that want to stretch a little bit, take a little bit of a risk. It’s not really a risk, but like in the corporate world. Oh my God, it’s something with an unknown. You know, there are a lot of people that are very allergic to that. It sounds like the secret is kind of understanding the culture you’re in. You can’t do anything you want, but there are going to be projects. And you just have to watch for one to go by. Is that the secret for intrapreneur versus entrepreneur?

 

Louis Gump:

That’s one angle. I don’t think there’s a single secret in terms of the thing that you do or the path that you take, but it is very important picking up on your point to understand the culture because a person who will be successful, let’s say just to pick a dynamic, let’s say that one company is very relationship-based and another company is very technology-based, and if you are more naturally suited to work in a relationship-based environment, you’re highly collaborative, your EQ is off the charts, maybe you find the company that is dedicated to innovation that also values those sorts of skills. And if you go into the one that’s technology-based and that kind of abrupt to the point, maybe short cycles and short attention spans, maybe that’s a place where the same person is going to have tougher sledding. Vice-versa.

If you have somebody who’s like, I just want to tell them like it is. I want to get straight to the point. I don’t have time to deal with all this people stuff and talk to the three other people who matter here, then maybe they’re better at the bigger company, or maybe they’re a better entrepreneur because I got to tell you, and I’ve both gotten this right and I’ve also had some misfires in larger organizations when I thought I was just being direct or candid. But it turned out there were subtexts that I didn’t understand. And so in these larger companies, you know, first find one that’s dedicated to growing and innovating, has budgets for these sorts of things. Typically, in any company that’s really great at this, the CEO walks the talk. They show up at the innovation days, and they’re reviewing the proposals. People don’t feel like they’re going to get the mallet on their head every time they come up with a new idea, you know. Some places it’s just like, “Hey, we’re busy.” But in places where there’s a track record of growth, in places where there’s a track record of acquiring companies and then building them successfully, Oracle might be an example of that, by the way. At least in some cases, you know, then you look for the culture. And when you find the match of the dedication to growth, the cash flow to fund new operations and culture, let me tell you, there’s a lot of magic there.

 

Todd Merrill:

So, do you carve out a like an innovation center or a you know, does it roll up to a very senior C-suite or is there a committee or how do you see these things manifesting in successful conditions? You know, is it one person? Is it a couple people? Is it like a whole committee or is there a formal process for submitting proposals or what does it look like at scale for intrapreneur success?

 

Louis Gump:

Yeah, there’s a bunch of best practices, but for starters, I’ve rarely seen a company succeed when there’s a single person who’s primarily responsible for innovation and everybody else is supposed to just go get their job done. In much more success when everybody understands that they’re a steward of the company, they’re a steward of the brand and it’s up to them to look for opportunities to drive innovation, whether it’s breakthrough innovation or whether it’s incremental innovation or whether it’s something in between.

If you look at something like the innovator’s dilemma, one of the ways you can handle this is by taking a business and putting it off to the side that can be very successful. Fusing it into the larger company later if that is something that a company wants to do, can sometimes be difficult. I also have seen situations where innovation centers, innovation hubs are very successful. Accelerators are very successful. However, the place where it’s most common for those to go wrong is when the people in the innovation center essentially take on the mantle of driving innovation and they exclude the operating businesses, where they’re more successful is where the leaders of the operating businesses have not only a commitment to innovation, but also goals related to it, and then they work collaboratively with an innovation center and leader.

 

Todd Merrill:

So, it goes back to your earlier comment. You know, a lot of people go for a bigger company. They learn how operations are successful, what that looks like. So, they know what the end kind of looks like or toward the end. And then they jump out, and they go, okay, I know what we’re building toward. It’s not haphazard. You know, there’s a structure here. And then that makes it a lot more successful. We were talking at dinner last… go ahead, you had a point.

 

Louis Gump:

Oh, yeah. I was just going to say, I’m thinking back to the mentors that I’ve had. The Weather Channel, for me, was transformational. And I’m thinking of a range of people like Debora Wilson, like Joe Fiveash, and many others like Lisa Chang, with whom we all learn together. And you know, I learned from some of the best, and now, to the extent that I’ve had some successes over time and I feel like one of the most fortunate people around in terms of a career, that’s because I was around some of the best there and at other places, and you have the opportunity not only to get things right, but also to learn and to fail. And when you do those things in combination, they tend to be pretty good testing grounds and pretty good preparation to lead and help others achieve their own potential.

 

Todd Merrill:

Wow! You know, I was just thinking about like the PayPal mafia. Yeah. So, PayPal is a great company. Very famous for all its alumni, Peter Thiel, Elon Musk, you know, they’ve all gone on and done amazing things. There’s something in the water there, or maybe they bounced off each other; they figured it out just right. And then, boy, you know, PayPal is not exactly synonymous with innovation today, except they bought Venmo, maybe that was innovative. So, what point do you kind of look at them and go, okay, this is no longer fertile territory for innovation? Is there always that point that inevitably comes, where do you think, you know, it’s a matter of getting the right DNA in a company to keep it going?

 

Louis Gump:

It’s the DNA. My perspective on this is that while there are a lot of factors, including industry evolution, including financial levers, and whatnot, most of the time, it comes down to leadership and leadership has a disproportionate effect. And if we look at the media industry, for example, nobody around us is going to change the mega trend that streaming is growing and traditional cable viewing is declining. I don’t care how good you are, but figuring out how to meet the needs of viewers, where they are with content that resonates and a business model that is sustainable, that’s possible. And not only is it possible, but some of the best and brightest are figuring it out. 

 

Todd Merrill:

I know you do some executive coaching. Where do leaders come from? What do leaders look like? How do you grow leaders, or are they made? I guess that’s a bunch of rapid-fire questions, but maybe we can kind of kick that around for a little bit.

 

Louis Gump:

Boy, there’s a lot of fertile ground there for discussions. I’ll start with this point about are leaders born or made? My experience is that a large portion of the people I know how to find have the capability for leadership, and a lot of it is learned. And the learning comes through an approach that includes curiosity, an approach that includes integrity. I’ve never met a successful leader in an innovative business who doesn’t work hard and, at the same time, someone who can take time to set boundaries and focus on the things that matter the most, at least over time. So, there’s a set of skills that are pretty common among people who have outsized success. And beyond curiosity, one of the next ones, especially in the context of an entrepreneurial venture, is the ability to build bridges with a lot of different types of people. So, I’ll start and then look back to you for the other parts of this topic.

 

Todd Merrill:

Yeah. So, building bridges, and when you’re the napkin holder in a startup, you know, you do whatever the heck you want, right? And people kind of have to either follow you or not. But as the size of the organization grows and as you try to do bigger and bigger projects, even if you’re a solo, you still need help from a lot of people, right? And then there are a lot of subtle ways people can shut you down or not help or not exactly, you know, torpedo you, but they’re not going to help you either. I don’t know. It’s kind of interesting. So, building bridges, curiosity. So, do you think these things are taught, you know, like I had one startup in the late 1990s and we were all working like hell and we’re all technical and we didn’t know what we didn’t know, but we knew, like none of us knew, certain parts of the business, marketing and, you know, financials and that kind of thing. We knew we needed help, but we didn’t know where to go. Right? So again, does this kind of come back to, I think you have to have a crucible experience or be a part of a great team before you can then become a leader. Is that how people learn stuff through osmosis or do you learn a lot by being a part of a successful culture? Is that a part of it? Or do you think you can get it from MBA school, or I don’t know, Boy Scouts or Junior Achievement, or other places? How do we create more leaders in society, or if you had a kid who was promising and you liked them, what would you coach them on how to grow to become a leader?

 

Louis Gump:

So, the definition of a leader is a person who has followers. And one of the most interesting things about that definition is that it doesn’t say whether you’re an effective leader, more effective, or less effective. It just says you’re a leader. And so I would say, you know, getting into situations where you have the opportunity to practice that is a really good start. And gosh, you know, if you’re going back to, let’s say, teen years, whether it’s scouts, and I know, I’m very familiar with the scouting program, I think that Scouting USA is one of the best youth leadership programs in the country. In addition to that, you know, if you care about sports, look at ways to … whether there’s an official title or not, but you act like the kind of person you would want to have leading your team. If you’re interested in theater, look at ways to act like the person you would want if you were leading the team and beyond. And then, as you grow into business, one of the most important things is to value the contributions of others. And one of the quickest ways, as opposed to building bridges, is to burn bridges. But if you’re going to do that, one of the best ways to do it is to think that you know it all. Not only does that tick other people off, but you’re also leaving the contributions from other people off to the side when you really need them. And you know, I remember starting as employee 1 of NewsON, and I know some things about product and I know some things about marketing, but I knew how to find people who are experts at product and experts at marketing. And when we brought them on board, and I’m thinking of specific people here, we just got that much better. I didn’t know at the time, I’d never had to figure out how to get health insurance for a company. But as employee 2, I had to, I was like, you mean somebody doesn’t do this for me? And the answer is no, you know. By the way, I was cleaning carpets too, but I had to figure out, you know?

 

Todd Merrill:

Ha ha ha, yeah.

 

Louis Gump:

So, then I had to figure out where an insurance broker is who could help me get health insurance so that we could take care of our team members. So, that’s not just an administrative task. That’s also a matter of creating an environment where people are valued. So, it can be from little things or ones that look administrative, all the way to a groundbreaking product. We ended up being a finalist for app of the year at CES, and we had good technology and we had great content, but what really made us succeed and brought us to the forefront was adaptability, curiosity, and a commitment to lifting each other up.

 

Todd Merrill:

Okay. So, there’s an old Indian saying, American-Indian, you know, if you want to go fast, go alone. If you want to go far, go with a group. That’s really true, right? You have to have a group of folks, and you all have to want to be there. Yeah. Huh. Neat. And then, so when you go into an organization, I don’t know if you, you know, it sounds like you’ve had a lot of success. If you go into an organization that’s struggling a little bit, and you see that there’s a leadership failure kind of what’s the go-to playbook, or what do you look for in terms of knowledge, skills, and abilities? Sometimes it’s exactly the wrong person, exactly the wrong place, but very rarely, right? Usually, it’s just that something is a little bit missing, and they’re coachable. Yeah. What do you see when you go out in these executive coaching kind of opportunities?

 

Louis Gump:

Yep. It helps to ask a lot of questions and not just for my knowledge, but what I’ve found is that a lot of people already have a running start on what needs to be done to fill in any gaps. Another thing that’s clear to me is that, and there’s a lot of research around this, a lot of people succeed the best when they mostly use their strengths. So, what I’m looking for then is to understand what people are best at, where their natural skills, their natural interests, where it almost, they say, even if they didn’t pay me, I’d want to do this because for them, it comes naturally, but to other people, it doesn’t. I look for ways to dial that up. And at the same time, I’m looking for a derailer. And, you know, a lot of the time, this will be on the softer side. Sometimes it’s technical, but a lot of the time, it’s an interaction style. It’s something where a person is communicating in a way that’s different from the culture of the company, and that sort of thing. And as a person who’s both gotten this right and gotten it wrong, you know, after a while you develop some radar on this. And I’ve just spoken with so many people. So, I’m looking for ways to spend about 80% of the time on building strengths, about 20% of the time on addressing weaknesses on an individual level, and then I’m looking for ways to make sure that we have the combination of leaders, so not only do things get done, but also there is the opportunity for kind of mutual respect and trust at the end of it. If you don’t have that, a lot of other things are really hard.

 

Todd Merrill:

So, let’s go back to this, intrapreneur is fascinating to me cause I’ve always just dismissed it as that’s stupid. You know, it’s not going to work, but I think you’re helping me come around on this. So that founder of that company that gets acquired needs to shift gears, sounds like they need a mentor or a Sherpa, is what you said, right? And they need a refocusing, so is that a great time to bring an executive coach and go, okay, you’re the CEO, you’re valuable, you’re now part of something bigger. We got to kind of redefine, you’re not going away, you know, but your role does have to change. Is that a coachable moment? Is that like right when you like to come in?

 

Louis Gump:

It’s just as important to have some sort of guidance then that is a little bit detached as it is for onboarding. And I think onboarding coaching for a new team member who’s entering a new company, that’s a pretty well-trodden path. It’s important. It’s valuable. You can read the first 90 days, and you can take some of those practices, but having somebody to bounce ideas off of is especially valuable for your own journey.

What I would also say for an entrepreneur and other team members who go into a larger company, there is similar value because even though they understand the kind of the pluses and minuses, the contours of their own business, they’re learning about a new environment and so you can have the same idea, the same widget, the same service, and with a successful integration and kind of people interaction, you’re off to the races. And if you start getting friction, then some of it is direct conflict, but a lot of it is quiet. The business just doesn’t give as much attention. You know, in a larger organization, it’s easy for an acquired company to get lost. And that’s as big a missed opportunity and cost as something that just simply invisibly fails.

 

Todd Merrill:

You know, it’s all about people and culture. It’s just amazing how that keeps coming up again and again and again. And leadership drives both of those. Right? Super critical and yeah.

 

Louis Gump:

Yep. If I could there, and there’s one other thing as we’re talking about it, that I didn’t say explicitly and is assumed, and that is, it’s very important to have a coherent, straightforward, and easy-to-understand strategy. Even if you’ve got a 50-page strategy document, and I hope most people don’t, but you’ve got a 50-page strategy document, if you have something that you can describe to somebody in between 30 seconds and two minutes, so that anyone from the most senior executive to the most junior entry-level employee can understand what your strategy is. That’s very powerful. And so if you combine that with the other things you mentioned, you increase the probability of success and people feeling like they can make a difference.

 

Todd Merrill:

You know, as a part of an acquisition, it was a rollup, and then it wasn’t indiscriminate. There was a strategy, and there are a bunch of companies that are stuck around that 25, 10, 20, 25,000 or million dollar a year ARR, and then, to grow, they had to do something else. And they kind of exhausted their niche. And then the pitch was basically, hey, we’re at this kind of company, and then it was like one of those trivial pursuit pies, you know, we’re the first two pie pieces, and then we do this. And then we have this theory that there’s a bigger company here, but we need this piece, and that’s you guys. We need this piece, and you all need to help us figure that one out, and this one and that one. So, you knew where you were, you had a clear swim lane, and why we’re doing it, and everybody was like, huh, yeah, that makes a lot of sense, you know. And then they came in, and it was a very successful acquisition. It was everybody’s kind of on board of, okay, I get this, you know. Hey, I got some ideas. And then in that kind of culture, it’s good for a lot of reasons. Now, Tripwire is Tripwire, and they became a big company and did really well. So, yeah. So, anything else you want to kind of throw on there? Did we cover all your basic points of success from your book for intrapreneurship?

 

Louis Gump:

Well, I think we’ve got a running start. One of the things that we haven’t covered is self-knowledge because let’s assume for a moment that there’s no single right answer, that this is situational. When someone takes the time to understand what they’re best at, that’s really helpful. We’ve talked about strategy. We haven’t talked too much about identifying opportunities. That’s a whole set of things we could discuss there. And then there is a concept that I wanted to mention also for our listeners around building teams, and that is the concept of the round table. And what I’ve found is that it’s perilous for anyone to assume that they’re the most important contributor on a team, even though that happens all the time. And here’s how it goes down. The product person, as a person who’s been a product person. 

So, I’ll start where I’ve been as a product person, you say, “We’re the most important because we create the products that the customers use.” And the technology person says, “I’m the most important because they can create all the products they want, but it only works when I do a good job.” And the salesperson says, “Well, actually, I’m most important because I’m the person who makes it rain. And you can build the products, and you can offer them in the marketplace, but only if we make the money, is this business going to go?” And then you look, say at legal or HR, most of the time, they don’t think they’re the most important, but often they’re critical to success. So, my recommendation is that everyone take the mindset figuratively. And sometimes, if it’s possible in an office, literally, to have a round table where everyone has a voice. And when you do that for the purposes of building a strong new business, you tend to have a much higher probability of success.

 

Todd Merrill:

I think that’s true. Ego-less, you know, we’re all in it together. We all have a part to play. Yeah, I think that’s true. And then, you know, identifying opportunities, maybe people should call you to run through that exercise.

 

Louis Gump:

Happy to do that.

 

Todd Merrill:

So, I heard there’s something kind of sports ball going on in Atlanta in like a year or something. You want to talk about that?

 

Louis Gump:

That’s right. You know, a small event that involves something, I think, around these parts, they call it soccer, is that right?

 

Todd Merrill:

Okay. All right. Yeah. World Cup, right?

 

Louis Gump:

So, we’ve got an event coming up, the World Cup. And if I heard correctly, there are going to be seven games played here in Atlanta. There will be games in other cities, too. And there’s a major development that’s happening downtown called Centennial Yards with a $5 billion investment to essentially help with the fan experience and transform an area that, for a long time, has been avoided by many. I know. I worked at CNN Center, and when I was there, we called it either the Gulch or the Pigeon Pit. And those were names for a reason. And now I was just down there a couple of weeks ago, taking a tour of Mercedes-Benz stadium, and I looked at what is coming together. It’s going to be tremendous. And especially when combined with the work that David Cummings and crew are doing, Jon Birdsong in South downtown, you know, we’re going to see a whole lot of change and a lot of opportunities for people to have a better experience than they’ve had in decades in that area.

 

Todd Merrill:

Well, I mean, so what a great thing. I was here for the Atlanta Olympics, and that was a wonderful experience for a lot of reasons. Yeah. So, it’s kind of fun spiffing up the town a little bit and then inviting in the neighbors for a good time.

 

Louis Gump:

Yes

 

Todd Merrill:

And that work in South downtown has kind of been really important. You know, that area has kind of come and gone. I can remember when I was a kid in the, gosh, the ‘70s, you know, we’d come up here, and I was a page for a day. And then the big thing was, you know, underground Atlanta was finally open again, and it seems to be this like heartbeat of Atlanta. It’s on again. It’s off again. It’s on again. It’s off again. So, it feels like that whole area should be on again. Yeah. So, that’s a good time. And so you’re involved with that. And then sounds like that’s different from business, but it’s kind of related to business, right? What’s that like working with a coalition of very high-powered business execs and then also community government? Is that like herding cats, or is it kind of a fun thing because everybody’s excited and there’s a lot of energy or, you know, who’s leading the pack down there?

 

Louis Gump:

Yep. So, it’s a real privilege to be part of this group. I’m active in the Media and Entertainment Society at the Technology Association of Georgia, and also known as TAG for anybody who isn’t as familiar with it. And TAG is doing some great work to educate and bring people together and to advocate along with others who are active in our community. And it’s in this case, inspiring to see what’s happening at the intersection of media and entertainment on the one hand and technology on the other. For example, there’s going to be a new entertainment space. I think it’s run by Cosm, and it’s the same outfit that put together the Sphere in Las Vegas. It’s going to be incredible. We just haven’t seen anything like it. And so I think what we’re seeing is that, you know, doing your day job is not enough from my perspective. You can, and look, we all have various aspects of our life at various times, but I think anyone who can get involved in the community in some way that works for the other obligations and other interests, that makes a lot of sense to me. And it’s a super exciting time to see the development there.

I can remember going to the World of Coke when it was down there at the Five Points area, and now, of course, it’s over at Centennial Olympic Park. And the other thing I would say is, having both toured the area around the stadium and Centennial Yards and also South downtown, I think that this one has some staying power. I perceive that we are going to see benefits for decades because of this.

 

Todd Merrill:

That’s amazing. Yeah, I’m sure we will. And it’s great to see all the energy down there in Atlanta.

Well, Louis, it’s been great having you. And it’s all about getting out there in the world and making things happen. You’re probably a man with a bunch of great travel stories. You want to share a couple of them with us before we go?

 

Louis Gump:

Gosh, there are quite a few, but one that comes to mind is a trip that I took to Denver back when I was active in the Mobile Marketing Association, speaking of being active in the community and by extension industry, and at the time there were a lot of questions about how to do both text messaging and also mobile advertising, and we had to bring people together from around the ecosystem. So, there were a bunch of us from media companies, bunch of us from wireless carriers, bunch of people from service providers, bunch of people from brands and marketers, and we all got together in Denver to create documents and guidelines so that the industry we would govern ourselves instead of inviting regulation because we didn’t take on a leadership role. And thankfully, we were very active in that. And after we had had enough of these gatherings, it almost became like a traveling circus, and we would show up in different places. And one of those was Denver. And we got there at a time when it was winter-ish, I don’t remember the exact date, and there was snow on the ground. And after a long day of meetings, we went over to a rodeo and we were watching, you know, these people hop up on broncos and bulls and ride around, and some of them stayed on and some of them got thrown off, but they all were in the ring. They were in the arena. And it occurred to me that’s a lot like people who innovate.

People who say, “Hey, I’m up for this.” It doesn’t have to always mean that I’m staying on the horse or the bull, but I’m going to make sure that I’m participating. And I thought it was a great metaphor for me that I keep in mind, aside from the fact that we all had a lot of fun together, in addition to the hard work. So, I think that’s the one that I would mention the most. Lots of good road trips along the way as well.

 

Todd Merrill:

Wow! Very cool. Well, Louis, it’s been great having you. How can people follow up with you on the internet after this, if they want to talk to you about leadership and coaching?

 

Louis Gump:

Thanks for asking. Well, I’m easy to find on LinkedIn, so they’re welcome to go find me there. And also, they can go to my website, Louisgump.com. And on the website, there’s a lot more information about the Inside Innovator and a place where you can sign up to reach out. So, either one should work.

 

Todd Merrill:

Awesome. Well, thanks. Thanks for coming Louis, and bye for now.

 

Louis Gump:

Bye for now. Thanks a lot, Todd. Take care.

What is the Sky Lounge?

Tales from the Sky Lounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people who are shaping the future of these industries. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.

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ABOUT OUR HOST

Todd Merrill, Interim and Fractional CTO, CISO

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

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email: Todd@SilverbackCTO.com
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