In Episode 135 of “The Trusted Advisor,” RSPA CEO Jim Roddy talks leadership with two startup founders/CEOs: Philip Wegner of TechGrid and Shawn Harris of Coworked. Among the topics discussed are the differences between leading at an established company vs. a startup, how to navigate early-stage turbulence, and how to establish and maintain a “democratic but decisive” leadership style.
“The Trusted Advisor,” powered by the Retail Solutions Providers Association (RSPA), is an award-winning content series designed specifically for retail IT VARs and software providers. Our goal is to educate you on the topics of leadership, management, hiring, sales, and other small business best practices. For more insights, visit the RSPA blog at www.GoRSPA.org.
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Full episode transcript via Apple Podcasts:
00:00:01.180 –> 00:00:14.940
Roddy: Hi, Jim Roddy here from the RSPA, jumping in before today’s podcast to make sure you know, Registration is now open for RetailNOW 2025, the Retail Technology Channel’s number one trade show, education conference, and networking event.
00:00:14.940 –> 00:00:23.380
Roddy: Join RSPA and Retail IT Channel leaders live and in person, July 27th through the 29th, on the strip in Las Vegas at Caesar’s Palace.
00:00:23.380 –> 00:00:28.580
Roddy: With nearly 200 exhibitors, RetailNOW is one-stop shopping for VARS and ISVs.
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Roddy: With an expected 1,600 or more attendees, it’s the place for extreme industry connectivity.
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Roddy: Across just 48 hours, you’ll meet new partners and new solution providers who can accelerate the success of your business.
00:00:41.880 –> 00:00:50.580
Roddy: Now, as I record this, early registrations are trending well ahead of many prior years, so don’t miss out on what could be the best RetailNOW ever.
00:00:50.580 –> 00:00:58.720
Roddy: If you’re serious about the Retail IT Channel, you have to attend RetailNOW 2025, again, July 27th through the 29th in Vegas.
00:00:58.720 –> 00:01:01.700
Roddy: RetailNOW is where the industry meets.
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Roddy: For all the details and to register at discounted early bird rates, visit the RetailNOW website today at gorsp.org/retailnow.
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Roddy: Again, gorsp.org/retailnow.
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Roddy: I hope you enjoy today’s episode.
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Roddy: Welcome to another episode of The Trusted Advisor Podcast and Video Series, powered by the Retail Solutions Providers Association.
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Roddy: Our goal on the pod is to accelerate the success of today’s and tomorrow’s leaders in the retail IT industry.
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Roddy: I’m Jim Roddy back with you again.
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Roddy: Thank you so much for joining us.
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Roddy: As always, we talk with leaders in the retail IT channel about their leadership journeys and what they’ve learned along the way.
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Roddy: And in this episode, we’re gonna talk with two special guests who are both leading startup companies.
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Roddy: Philip Wegner is the CEO of TechGrid, a company he established in 2021.
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Roddy: TechGrid is a platform built for VARs and MSPs designed to improve the manual quote to cash process.
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Roddy: Prior to launching TechGrid, Philip was the founder and CEO of Secure Edge Networks, a managed services provider headquartered in Charlotte, North Carolina.
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Roddy: Philip, welcome to The Trusted Advisor.
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Wegner: Hey, thanks for having me.
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Roddy: And Philip, I remember when our paths crossed back in VARtech, I guess a year or two ago, and you did a product demo for me, and I was like, that is really neat.
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Roddy: You guys would be a great fit for the association.
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Roddy: So I’m glad you’re here and I’m glad VARtech happened so we could make this podcast today happen.
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Wegner: Yeah, thanks so much.
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Wegner: I appreciate that.
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Roddy: You bet.
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Roddy: Our second guest is Shawn Harris.
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Roddy: He’s the co-founder and CEO of Coworked, which has developed a product called Harmony, which is billed as the world’s first AI project manager.
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Roddy: Shawn’s also currently a fellow at the Black Venture Institute, and he’s a member of TBD Angels.
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Roddy: Now, previously, he worked for Zebra Technologies for seven years, TJX for five years.
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Roddy: He was a founder or co-founder of several other startups, and he served eight years in the Army National Guard.
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Roddy: Shawn, thank you for your service, and great to talk with you today.
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Harris: I’m glad to be here, Jim.
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Harris: Thanks for having me.
00:03:09.564 –> 00:03:09.964
Harris: You bet.
00:03:09.964 –> 00:03:21.084
Roddy: And I remember when we first met at NRF a few years back, and I’m glad everybody else went to the main floor, I went to the lower floor, and I’m glad you were exhibiting there.
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Roddy: It was great to meet with you then.
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Harris: Yeah.
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Harris: I’m glad that we crossed paths, and here we are today, and thank you for allowing me to be a part of the RSPA.
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Roddy: No, thank you.
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Roddy: And I’m so glad both of you guys are members of the association.
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Roddy: And I gave a one-sentence description of each of your organizations, but I’m hoping each of you, starting with Philip, can you tell our audience about the story of when and how your company started and what it looks like today?
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Roddy: So Philip, if you could tell your startup story first, please.
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Wegner: Sure.
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Wegner: Well, I started a technology integrator back in 2006.
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Wegner: And if you remember back that far, I think both of you guys have been in the industry that long.
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Wegner: It was when Wi-Fi networks and those types of things were very innovative.
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Wegner: And so I started a company deploying those big networks at the time in schools, hospitals, airports, and things like that.
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Wegner: And then as I grew that company over the years, I just grew really frustrated with how we’re functioning internally.
00:04:22.604 –> 00:04:28.204
Wegner: And having like one system talk to another system, building these kind of online experiences for our customers.
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Wegner: You know, the customer is really expecting an Amazon style experience and where they can log in and see what’s going on.
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Wegner: And we couldn’t make that happen.
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Wegner: And so, what I ended up doing is buying a software company in 2019 and then started building a lot of those components to actually run that company.
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Wegner: And I didn’t, I wasn’t visionary enough to think that I would be offering that to other companies, but we ended up selling off the MSP business and then packaging that software and selling it to other MSPs and bars.
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Roddy: Interesting.
00:05:01.884 –> 00:05:03.324
Roddy: And so, tell me about your company today.
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Roddy: How many employees do you have?
00:05:06.224 –> 00:05:11.824
Roddy: I guess if you could also talk about how it’s financed, if you don’t mind answering that question, the verticals you focus on.
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Wegner: Yeah.
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Wegner: So we’re currently selling software to MSPs and bars, who are supporting business customers.
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Wegner: We support MSPs and bars that are across all business verticals, selling to retail, selling to hospitality, selling to manufacturing companies, whatever.
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Wegner: Our product will fit kind of all those.
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Wegner: We actually did recently raise money, I’m assuming that’s why I’m asking the question, but Arnie Bellini is a major backer, who was the founder of ConnectWise.
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Wegner: Prior to that, we really self-funded.
00:05:41.084 –> 00:05:50.784
Wegner: The money that cost to build the software, we were using the profits of the main company to fund the development of the software.
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Wegner: It wasn’t until just a year and a half or so ago that we raised any sort of outside funding.
00:05:55.824 –> 00:06:06.044
Wegner: It really had a lot to do with Arnie, being kind of the godfather of the MSP industry, and then meeting him at an event, and then one thing led to another.
00:06:06.044 –> 00:06:12.404
Wegner: But prior to that, we were primarily self-funded, and we’re mostly a bunch of software developers at this point.
00:06:12.404 –> 00:06:18.344
Wegner: Most of our team is made up of people building things, and then we have a very small core team outside of that.
00:06:18.344 –> 00:06:20.584
Wegner: So we have roughly 30 employees today.
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Roddy: Got it.
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Roddy: I have to say, Arnie Bellini actually spoke at an RSPA event one time.
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Roddy: He was bringing that whole managed services as a service model to this industry.
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Roddy: I’ll never forget.
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Wegner: Interesting.
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Roddy: He had a couple of VARs on stage with him, and then they opened up to the microphone.
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Roddy: Any questions?
00:06:37.024 –> 00:06:42.504
Roddy: And a long time reseller got up to the microphone, and its first words were, this will never work.
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Roddy: But now that reseller, his son is now running the business, and I just talked with him recently, and now about two thirds or three quarters of what they do is all on a recurring revenue basis.
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Roddy: So I was told that Arnie-
00:06:54.724 –> 00:06:59.264
Wegner: What’s so funny about that is that it’s the IT industry that’s actually reluctant to change.
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Wegner: It’s so nice to see this, which is amazing.
00:07:02.944 –> 00:07:04.604
Harris: The one’s driving change, yeah.
00:07:04.604 –> 00:07:06.024
Roddy: Yeah, it’s all worked out in the long run.
00:07:06.024 –> 00:07:07.724
Roddy: So Shawn, tell us your story.
00:07:07.724 –> 00:07:11.764
Roddy: Tell us about Coworked and how it came to be and what it is today.
00:07:11.764 –> 00:07:19.084
Harris: Yeah, so back in 2023, a couple of my co-founders and I got together.
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Harris: We had known each other for well over a decade, and we’re having exploratory conversations with retailers about AI and where we thought it was going.
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Harris: From some of those conversations, we started to realize this little kernel of a pain point that we were hearing, and oddly enough, it was centered around something that is a perennial problem with retailers, and that is the coordination of in-store deployments, that they do on an annual basis, and making it such that when store tech wants to do something for us, when HR wants to do something for us, when real estate wants to do something, that there is a harmonized schedule that’s built to reduce the impact on store operations.
00:08:09.724 –> 00:08:22.244
Harris: It was in this conversation that we, one, started to hear about the thing we had personally experienced, but hear more about the contemporary issues of the cognitive load on project managers.
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Harris: Like, I can’t do all of this, because it keeps changing and things are slipping through the cracks.
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Harris: And literally from that little bit of an inkling from a very large retailer, we started to ideate on and build Harmony.
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Harris: Harmony is an agentic project manager that is able to execute projects from end to end as a co-worker within the enterprise.
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Harris: But it was from that kernel of an interaction with a retailer, validated with a few others, that led us to build the platform.
00:09:06.044 –> 00:09:09.184
Harris: This is back in 2023.
00:09:09.184 –> 00:09:09.464
Roddy: Got it.
00:09:09.464 –> 00:09:12.204
Roddy: And so you focused solely on retail.
00:09:12.204 –> 00:09:18.824
Roddy: Can you talk about, if you’re willing to share it, how you’re financing and how many full-time employees you have or FTE equivalents?
00:09:19.924 –> 00:09:27.404
Harris: Well, one thing to update you on there is we are now across industries.
00:09:27.404 –> 00:09:27.944
Roddy: Oh, are you?
00:09:27.944 –> 00:09:28.344
Harris: Okay.
00:09:28.344 –> 00:09:29.104
Harris: Yeah.
00:09:29.104 –> 00:09:29.324
Harris: Yeah.
00:09:29.324 –> 00:09:33.484
Harris: We’re now, we support both retailers.
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Harris: We have a semiconductor company.
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Harris: We have an enterprise technology company that’s using it.
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Harris: We have a company and an energy company in Jakarta that’s looking at, we’re talking to a bank in Bahrain, like literally like it is, it is fundamentally a project manager that can work across projects.
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Harris: We initially self-funded the business.
00:10:02.764 –> 00:10:06.244
Harris: We got accepted into Techstars and got a little bit of money from Techstars.
00:10:07.924 –> 00:10:13.184
Harris: We recently raised Institutional Venture Capital.
00:10:13.184 –> 00:10:26.464
Harris: Now we are VC-backed startup, which it always blows my mind to hear the stats here, but even though we hear about it happening all the time, still like literally 1 percent of startups are venture-backed.
00:10:28.224 –> 00:10:38.964
Harris: We are venture-backed now and we are raising around right now to the kind of that will get us through to our Series A.
00:10:38.964 –> 00:10:39.784
Roddy: Got it.
00:10:39.784 –> 00:10:40.164
Roddy: Great.
00:10:40.164 –> 00:10:41.784
Roddy: How many people do you have?
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Harris: Ten.
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Harris: We have ten full-time equivalents working on this.
00:10:45.124 –> 00:10:45.744
Harris: Yeah.
00:10:45.744 –> 00:10:49.344
Harris: Majority are product folks.
00:10:49.344 –> 00:10:49.804
Roddy: Got it.
00:10:49.804 –> 00:10:52.224
Roddy: See, it’s funny because RSPA has 10 employees as well.
00:10:52.244 –> 00:11:00.244
Roddy: Like there’s a parallel, but I’m like, we’ve been around for 77 years, we don’t know where to start in terms of raising capital or anything of that nature.
00:11:00.644 –> 00:11:02.564
Roddy: Totally different.
00:11:02.564 –> 00:11:08.944
Roddy: There’s some similarities, but then there’s things that are totally different between a startup and an established company.
00:11:08.944 –> 00:11:21.464
Roddy: Shawn, if I can stay with you and ask you, because we have a lot of startups that are inside the RSPA, I don’t know of any where it was like smooth sailings, no turbulence from day one.
00:11:21.464 –> 00:11:28.304
Roddy: Can you tell us about a significant obstacle or challenge that you’ve encountered as a startup leader and then how you navigated it?
00:11:29.604 –> 00:11:49.664
Harris: Yeah, I guess like as I sat and I thought a little bit about this question, gosh, there are just on a daily basis, there’s probably more things that I run into as challenges than, more things I forget than actually stay resident.
00:11:49.664 –> 00:12:00.864
Harris: But I would say like the greatest challenge that you have as a startup founder is bringing the right people onto the bus, right?
00:12:01.424 –> 00:12:09.224
Harris: And for what it’s worth, getting people off that bus as necessary as well.
00:12:09.224 –> 00:12:17.624
Harris: And so there’s always this ideal of, for what it’s worth, higher slow and fire fast.
00:12:17.624 –> 00:12:36.544
Harris: Because at this stage, when you’re 10 people, when you’re potentially less, you need to have a very, you need to have what they would call like the A-caliber folks on your team, bringing to their division and mission of the enterprise, of your venture.
00:12:36.544 –> 00:12:43.864
Harris: And if you don’t, it can be detrimental to the limited resources that you have.
00:12:43.864 –> 00:12:57.124
Harris: And so I would say, for us, I’ve been very thoughtful about the individuals that we bring on to the mission to get things done.
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Harris: And yeah, when you ask about, what are the things that you run to that you haven’t gotten right?
00:13:04.584 –> 00:13:08.424
Harris: I’m very thoughtful about it, but you still can get it wrong.
00:13:08.424 –> 00:13:21.144
Harris: Being fast with making, being decisive with decisions, being driven to bring people to bear, that’s based on what are going to be the principles of your organization is key.
00:13:21.584 –> 00:13:29.984
Harris: And yeah, I’ll center there, but it’s been around hiring and firing of folks that we’ve had to navigate even as a small company.
00:13:29.984 –> 00:13:30.284
Roddy: Got it.
00:13:30.284 –> 00:13:35.364
Roddy: Yeah, because your product will take you so far, but your people have to develop and advance your product and everything.
00:13:35.364 –> 00:13:37.484
Roddy: Your people are everything.
00:13:37.484 –> 00:13:38.784
Roddy: Yeah.
00:13:38.784 –> 00:13:45.284
Roddy: Philip, can you tell us a story about an obstacle or challenge that you encountered and how you overcame it?
00:13:45.284 –> 00:13:52.484
Wegner: Well, I agree with Shawn that if you’re signing up to run a small business or be part of a startup, you’re really signing up for challenges.
00:13:52.744 –> 00:13:56.384
Wegner: And so you’re really signing up for turbulence, if you will.
00:13:56.384 –> 00:14:06.084
Wegner: And so every day you’re trying to figure out something new because you’re establishing something that a path that really hasn’t been had been gone down before, at least for your own company.
00:14:06.084 –> 00:14:17.684
Wegner: But specifically for me, the real big transformational thing for me was the pandemic, because at the time I was running an MSP, our major customer base was retail at the time.
00:14:17.684 –> 00:14:22.924
Wegner: And we were going into 2020 thinking we’re going to be, we’re going to crush it.
00:14:22.924 –> 00:14:24.804
Wegner: I was hiring people like crazy.
00:14:24.804 –> 00:14:33.444
Wegner: We were, we hired a big director of VP of Sales, and we hired a bunch of salespeople, because we’d really figured out the as a service model you were talking about.
00:14:33.444 –> 00:14:37.384
Wegner: And our goal was to go into retail and just absolutely print.
00:14:37.384 –> 00:14:39.624
Wegner: We were like, we’re just going to redo this over and over again.
00:14:39.624 –> 00:14:44.584
Wegner: And then the pandemic hit and everything halted overnight.
00:14:44.584 –> 00:14:57.904
Wegner: And I think our revenue dropped by 60 some percent in one month, because our major customer that we had millions of dollars slated for that year went bankrupt literally very, very quickly.
00:14:57.904 –> 00:15:00.364
Wegner: And then essentially what we were doing got halted.
00:15:00.364 –> 00:15:01.744
Wegner: It just completely stopped.
00:15:01.744 –> 00:15:09.144
Wegner: And what’s really funny about looking at us today is at the time, we were playing around with software.
00:15:09.144 –> 00:15:10.344
Wegner: I’d already bought a software company.
00:15:10.344 –> 00:15:15.664
Wegner: We were building some things, but we were kind of still in the MSP business and we had some software.
00:15:16.324 –> 00:15:26.564
Wegner: When the pandemic hit, I remember calling my product manager and saying, okay, we’re going to build software.
00:15:26.724 –> 00:15:34.604
Wegner: And in my mind, I’m thinking we’re going to build software until we die, because I don’t see how we’re going to make it through this thing.
00:15:34.604 –> 00:15:39.324
Wegner: And what ended up coming out the other side is that we had built a platform and all this kind of things.
00:15:39.504 –> 00:15:44.884
Wegner: And what was transformational for us is we never would have had time to build if it wasn’t for the pandemic.
00:15:44.984 –> 00:15:54.704
Wegner: If the pandemic wouldn’t have hit, when it hit at the timing, we never would have had the time to really to build what we have today.
00:15:54.704 –> 00:15:55.564
Roddy: Interesting.
00:15:55.564 –> 00:16:03.024
Roddy: So, I’m going to ask both of you this question, but Philip, first, since you brought it up, you said, like, you know, when you’re running a startup, you’re signing up for Turbulence.
00:16:04.464 –> 00:16:05.564
Roddy: Why would you do that?
00:16:05.564 –> 00:16:09.524
Roddy: Why wouldn’t you go get a J-O-B where there’s less Turbulence?
00:16:09.524 –> 00:16:11.164
Roddy: Like, why do you do this?
00:16:11.164 –> 00:16:11.804
Wegner: I don’t know, man.
00:16:12.184 –> 00:16:22.664
Wegner: I think it’s something, it’s a DNA thing, where there’s, like, just a personality trait, whether it’s stupidity or this belief that you can do something.
00:16:22.664 –> 00:16:28.764
Wegner: Because literally, if you just look at the numbers, like, just pure math, and let Shawn said earlier, like, they’ve raised venture capital.
00:16:28.764 –> 00:16:30.324
Wegner: Almost nobody raises venture capital.
00:16:30.324 –> 00:16:33.744
Wegner: So he’s already, like, in the less than 1% of, like, startups, you know?
00:16:33.744 –> 00:16:37.224
Wegner: And then, like, the numbers, like, 83% of those companies fail, you know?
00:16:37.224 –> 00:16:38.704
Wegner: And so you’re signing up for something.
00:16:38.704 –> 00:16:48.184
Wegner: I think you really have to have some sort of purpose-driven, reason-to-do-it, and hopefully that really is why, is you’re a missionary, not a mercenary.
00:16:48.184 –> 00:16:57.984
Wegner: And that’s really, for me, it was always kind of the thing, is I feel like I’m a man on a mission, and so that’s gonna require me to go through some pain.
00:16:57.984 –> 00:16:58.584
Roddy: Got it.
00:16:58.584 –> 00:17:07.364
Roddy: Yeah, and you said, you know, sometimes it might be stupidity, and I’ve always liked the quote, there’s a very fine line between bravery and stupidity, and sometimes you don’t know which line you’re on.
00:17:07.804 –> 00:17:11.864
Roddy: Shawn, why are you in the startup world?
00:17:11.864 –> 00:17:27.724
Harris: Yeah, so I’ve definitely been asked this question quite a few times, and parts of me say that from a nature perspective, that I definitely think I have a little screw loose that is willing to take the risk.
00:17:27.724 –> 00:17:28.644
Harris: The risk, right?
00:17:28.644 –> 00:17:32.444
Harris: I mean, at least like the perceived risk, right?
00:17:32.484 –> 00:17:41.584
Harris: Because fact is like there’s risk in even having a full-time job, like in terms of like how that all works.
00:17:41.584 –> 00:17:46.644
Harris: I think a lot of folks realize that to be the case.
00:17:46.644 –> 00:17:51.024
Harris: So I think that from a nature perspective, I think I have a little bit of screw loose.
00:17:51.044 –> 00:17:58.224
Harris: From a nurture perspective, I literally grew up around a lot of entrepreneurship as well.
00:17:58.224 –> 00:18:00.504
Harris: And so I got to see it with my own eyes.
00:18:00.504 –> 00:18:04.804
Harris: I got to see the good, the bad and the ugly and said, okay, I can do this.
00:18:04.804 –> 00:18:06.684
Harris: I can be that, right?
00:18:06.684 –> 00:18:15.584
Harris: And so I think the combination of the two lent itself to me having a willingness, a tolerance to it as well.
00:18:16.304 –> 00:18:33.824
Harris: And I would be wrong for not saying I have an extremely, extremely supportive wife, extremely supportive wife who allows me to do what I do.
00:18:33.824 –> 00:18:34.724
Roddy: Excellent.
00:18:34.724 –> 00:18:40.564
Roddy: You know, the mindset thing makes me think of, I had a coworker who, I remember he had to be out for, because he had to have neck surgery.
00:18:40.564 –> 00:18:42.964
Roddy: I’m like, man, why do you need neck surgery?
00:18:42.984 –> 00:18:46.724
Roddy: He was like in his mid, late 50s, and he said, well, I served in the military.
00:18:46.724 –> 00:18:54.284
Roddy: I did a lot of skydiving, and then he did extreme altitude skydiving, but he obviously couldn’t do it anymore.
00:18:54.284 –> 00:18:55.504
Roddy: And I said, do you miss it?
00:18:55.504 –> 00:19:01.804
Roddy: And he just said, every day, every day, like I cannot find the rush, being this close to the ground.
00:19:01.804 –> 00:19:04.664
Roddy: And that’s the thing sometimes how entrepreneurs are, right?
00:19:04.664 –> 00:19:05.944
Roddy: People who lead startups, right?
00:19:05.944 –> 00:19:07.064
Roddy: They need that rush.
00:19:07.064 –> 00:19:12.924
Roddy: They couldn’t, even if they were making more money somewhere else, you’re getting a steady paycheck, they need that adrenaline.
00:19:12.924 –> 00:19:15.824
Roddy: And that’s again the parallel that I draw.
00:19:15.824 –> 00:19:20.424
Roddy: So let’s talk about the difference between being inside an established organization, right?
00:19:20.424 –> 00:19:22.504
Roddy: Philip, you built up Secure Edge, right?
00:19:22.504 –> 00:19:23.924
Roddy: Had an established organization.
00:19:23.924 –> 00:19:27.984
Roddy: Shawn, you worked at Zebra, as I said, seven years, and now you’re leading startups.
00:19:27.984 –> 00:19:37.164
Roddy: So Philip, if you want to go first, what do you see as the biggest difference between leading at an established company versus something that’s more of a new co?
00:19:37.984 –> 00:19:43.584
Wegner: Well, I’m a firm believer that if you scale an established company well, then you’re building it around small teams.
00:19:43.704 –> 00:19:53.364
Wegner: And this is a philosophy that I have, is that you really want to build small teams that are effectively building something or doing something.
00:19:53.364 –> 00:20:06.004
Wegner: And what happens at a large company or the tendency is, you end up getting with a lot of this communications overhead and collaboration overhead, and so you end up with just this meetings fast going on internally.
00:20:06.084 –> 00:20:08.584
Wegner: And so you go to a big company and you’re like, hey, what did you do today?
00:20:08.584 –> 00:20:13.384
Wegner: I had seven meetings, where there’s meetings with customers, no, they’re all internal.
00:20:13.384 –> 00:20:18.124
Wegner: Well, you’re literally just collaborating across team, like who is actually doing work?
00:20:18.304 –> 00:20:26.104
Wegner: And the really hard part when you’re scaling a business is keeping that from happening as you start to grow your company.
00:20:26.104 –> 00:20:30.844
Wegner: So I’m a big believer in working backwards if you’ve read that book.
00:20:30.844 –> 00:20:41.544
Wegner: A lot of the Amazon style of leadership and Spotify and some of these other organizations have adopted the same type of organizational structure where they have small teams with single threaded leaders.
00:20:41.544 –> 00:20:50.524
Wegner: And so they’re really good at building these small teams that are building something and working on something and then having a leader that their entire job is to accomplish that particular goal.
00:20:50.524 –> 00:20:58.204
Wegner: And so I think that’s as we grow TechGrid, that’s going to be kind of the style that we’re going to use to grow the company.
00:20:58.244 –> 00:21:04.084
Roddy: Yeah, small teams, I worked for a couple of brothers who were entrepreneurs and they would always talk about independent stand-alone operating units.
00:21:04.084 –> 00:21:04.444
Wegner: Yes.
00:21:04.444 –> 00:21:04.604
Wegner: Right.
00:21:04.604 –> 00:21:09.364
Roddy: Even though they owned all of them, they made sure that they could have some level of independence.
00:21:09.704 –> 00:21:09.884
Roddy: Right.
00:21:09.884 –> 00:21:13.564
Roddy: Maybe they share the same handbook and accounting systems and things like that.
00:21:13.564 –> 00:21:14.984
Roddy: But is that kind of what you’re saying, Philip?
00:21:15.384 –> 00:21:16.204
Wegner: 100 percent.
00:21:16.204 –> 00:21:19.344
Wegner: There’s there’s entire books written on the subject.
00:21:19.344 –> 00:21:25.464
Wegner: And then there’s a lot of really good ones, specifically about how Amazon scaled that is really, really good.
00:21:25.464 –> 00:21:32.004
Wegner: But there’s another good one by Jeff Lawson, the founder of Twilio, where he talks about building with small teams.
00:21:33.144 –> 00:21:33.484
Roddy: Love it.
00:21:33.484 –> 00:21:33.804
Roddy: Thank you.
00:21:33.804 –> 00:21:34.964
Roddy: I’ve written that down.
00:21:34.964 –> 00:21:37.164
Roddy: So working backwards, I will check that out.
00:21:37.164 –> 00:21:44.024
Roddy: So Shawn, what’s the difference work in Zebra, work in an established company versus a startup world?
00:21:44.024 –> 00:21:44.284
Harris: Yeah.
00:21:44.284 –> 00:21:50.464
Harris: I think the first thing I’d say is the degree of support that you have within a large enterprise.
00:21:50.524 –> 00:21:55.224
Harris: So literally, there is going to be an individual who can make your PowerPoint.
00:21:55.224 –> 00:21:59.624
Harris: There’s going to be an individual who will help you reset a password.
00:21:59.624 –> 00:22:02.344
Harris: There’s going to be an individual who’s going to help.
00:22:03.964 –> 00:22:08.764
Harris: Maybe you need help with writing an e-mail or doing something like this.
00:22:08.764 –> 00:22:12.344
Harris: There’s somebody for everything inside a large enterprise.
00:22:12.344 –> 00:22:23.684
Harris: I think that’s just a function of the need for specialization because of the need for maybe having individuals that are going to be doing a given task the most optimally.
00:22:23.684 –> 00:22:29.824
Harris: As a startup founder and having the startup mindset, you need to be a generalist.
00:22:29.824 –> 00:22:33.824
Harris: You need to be able to cover a lot of bases.
00:22:33.824 –> 00:22:47.764
Harris: I think that gives you the, sure, you’re going to be not as deep in a lot of things, but you understand very clearly the interconnection between a lot of different disciplines within an enterprise.
00:22:48.924 –> 00:22:53.584
Harris: It serves itself, being a generalist is a key thing that’s required in a startup.
00:22:53.584 –> 00:22:57.604
Harris: It serves you very well in the space.
00:22:57.604 –> 00:23:02.224
Harris: It doesn’t serve you very well in a large enterprise.
00:23:02.304 –> 00:23:19.884
Harris: I guess, unless you’re doing entrepreneurship, where you’re given the opportunity to run a new thing within the enterprise, and certainly the ideals of what that looks like and takes is a whole other conversation as well.
00:23:19.884 –> 00:23:23.624
Harris: But those are the things I think about, support and specialization.
00:23:23.624 –> 00:23:24.144
Roddy: Interesting.
00:23:24.144 –> 00:23:27.504
Roddy: And so for those on YouTube, I’m turning my camera a little bit.
00:23:27.504 –> 00:23:31.264
Roddy: You can see a magazine cover on there from age 23 to 28.
00:23:31.964 –> 00:23:34.804
Roddy: I published a sports magazine, so I owned my own business.
00:23:34.804 –> 00:23:36.864
Roddy: It was up in Northwest Pennsylvania.
00:23:36.864 –> 00:23:42.944
Roddy: After going through that experience, I remember thinking, there are a lot of countries that have a year of military service that’s mandatory.
00:23:42.944 –> 00:23:48.864
Roddy: I thought, man, there should be a year of self-employment that is mandatory because it totally changes your perspective.
00:23:48.944 –> 00:23:52.784
Roddy: Because if you work for somebody, you’re like, I need a paycheck, I need this, I need that.
00:23:52.784 –> 00:23:53.524
Roddy: You take care of me.
00:23:53.524 –> 00:24:00.204
Roddy: And I was like, my payroll was going to the mailbox, crossing my fingers, opening up like, oh good, checks are here.
00:24:00.284 –> 00:24:07.144
Roddy: And like you said, Shawn, nobody’s bringing in donuts, because it’s just you to start off with from that standpoint.
00:24:07.144 –> 00:24:08.584
Roddy: So I don’t know what you guys feel about that.
00:24:08.584 –> 00:24:11.364
Roddy: I don’t think I could get elected president on that platform.
00:24:11.364 –> 00:24:13.564
Roddy: But I think it’d be beneficial.
00:24:13.564 –> 00:24:19.664
Harris: Yeah, I’m with you, I’m with you, actually literally on both fronts.
00:24:19.664 –> 00:24:22.864
Harris: One, yeah, the year of service I think would be wicked.
00:24:22.864 –> 00:24:25.704
Harris: Just having lived it, I think it would be foundational.
00:24:25.844 –> 00:24:35.244
Harris: Second is my alma mater, actually Bapsin College, which is known for entrepreneurship for the undergrads.
00:24:35.244 –> 00:24:36.424
Harris: They do that.
00:24:36.424 –> 00:24:40.544
Harris: Pretty much every undergrad needs to run a business.
00:24:40.544 –> 00:24:42.264
Harris: Every undergrad needs to run a business.
00:24:42.264 –> 00:24:46.024
Harris: Yeah, so it’s part of the learning there.
00:24:46.024 –> 00:24:50.424
Roddy: All right, Philip, will you join my crusade that everybody has a year of mandatory self-employment?
00:24:50.424 –> 00:24:52.504
Wegner: My kids are already trying to sell stuff to people.
00:24:53.164 –> 00:25:00.864
Wegner: I have a 10-year-old little girl and she will take something from your desk, paint it and then sell it back to you.
00:25:03.664 –> 00:25:05.564
Roddy: Very good.
00:25:05.664 –> 00:25:15.384
Roddy: I don’t have an official master’s, but I had no debt from the, I guess I had a little bit of debt, but I was able to pay that back pretty quickly afterwards.
00:25:15.384 –> 00:25:17.184
Roddy: But boy, what a learning experience it was.
00:25:17.184 –> 00:25:20.424
Roddy: It is walking on a tightrope with none.
00:25:20.424 –> 00:25:25.484
Roddy: Again, I was running a really tiny micro business, but a lot of lessons there.
00:25:25.484 –> 00:25:31.604
Roddy: Enough about that and we’re going to pause to let our listeners and viewers know about the Retail Solutions Providers Association.
00:25:31.604 –> 00:25:46.224
Roddy: The RSPA is North America’s largest community of retail technology, VARs, software providers, vendors, and distributors to accelerate your access through an RSPA membership, whether you’re an established company or a startup, email membership at gorspa.org.
00:25:46.224 –> 00:25:51.624
Roddy: Also, we want to thank these companies who support the RSPA community and make this podcast and video series possible.
00:25:52.044 –> 00:25:53.924
Roddy: Our Platinum Sponsors, Blue Star.
00:25:53.924 –> 00:25:58.624
Roddy: Our Gold Sponsors are Cocard, Epson, Heartland, and ScanSource.
00:25:58.624 –> 00:26:08.504
Roddy: And then finally, want to make sure everybody knows, registration is now open for RetailNOW 2025, the Retail IT Channel’s number one trade show, education conference, and networking event.
00:26:08.504 –> 00:26:13.924
Roddy: This year’s event is set for July 27th through 29th at Caesars Palace in Las Vegas.
00:26:13.924 –> 00:26:16.264
Roddy: For more information, visit gorspa.org/retailnow.
00:26:19.344 –> 00:26:22.844
Roddy: RetailNOW is where the industry meets.
00:26:22.844 –> 00:26:23.184
Roddy: All right.
00:26:23.184 –> 00:26:29.384
Roddy: So you guys have shared a lot of your company stories and intertwined some of your personal leadership traits in there.
00:26:29.384 –> 00:26:31.984
Roddy: And Shawn, I’m hoping you can take this question first.
00:26:31.984 –> 00:26:34.684
Roddy: So how would you describe your leadership style?
00:26:34.684 –> 00:26:41.264
Roddy: Are there like a few overarching words or phrases that represent what you’re striving for as you lead Coworked?
00:26:41.304 –> 00:26:50.204
Harris: Yeah, I’ve kind of relied on this ideal pretty much my whole career, that I’m an individual that is democratic but decisive.
00:26:50.204 –> 00:27:03.684
Harris: When it comes to running any team, whether it’s a team internal to a large enterprise or it’s a startup, making decisions and moving is important.
00:27:03.684 –> 00:27:13.284
Harris: And so the democratic side of me likes to hear, and the curious soul of me wants to hear the ideas and thoughts and considerations.
00:27:13.284 –> 00:27:21.684
Harris: And if an individual has a decision that will be value add to what we’re trying to accomplish, let’s go.
00:27:21.684 –> 00:27:28.564
Harris: If we are fumbling around trying to figure out what to do, I will decide what to do, right?
00:27:28.744 –> 00:27:30.744
Harris: And push and push and push.
00:27:30.744 –> 00:27:36.424
Harris: And so I like to characterize myself classically as being democratic but decisive.
00:27:36.424 –> 00:27:44.984
Roddy: And democratic, just to expand on that, you’re talking about like, make sure everybody’s weighing in, getting feedback, having the dialogue back and forth.
00:27:44.984 –> 00:27:47.504
Roddy: Is that how you would describe when you say democratic?
00:27:47.504 –> 00:27:49.284
Harris: Yeah, everybody might be an overstatement.
00:27:49.284 –> 00:27:58.744
Harris: Those who are willing to, those who are actually actively and willing to contribute to making a decision, 100 percent, right?
00:27:58.744 –> 00:28:06.104
Harris: But I’m not going to like seek everyone if they’re not trying to be an active and engaged part of that process.
00:28:06.104 –> 00:28:14.044
Harris: And when it’s all said and done, we’re going to make a collective or individual decision quickly to move forward.
00:28:14.044 –> 00:28:18.044
Harris: So that’s speed, especially in a startup.
00:28:19.084 –> 00:28:26.884
Harris: Life speed is very important because every delay is a incremental deduction in your available resources, right?
00:28:26.884 –> 00:28:30.364
Harris: And so decisions matter and they need to happen fast.
00:28:30.364 –> 00:28:30.784
Roddy: Excellent.
00:28:30.784 –> 00:28:33.004
Roddy: Philip, can you describe your leadership style?
00:28:33.004 –> 00:28:34.664
Wegner: Well, first of all, I love what Shawn said there.
00:28:34.904 –> 00:28:40.424
Wegner: And I think it’s really important to have an environment where people are open to say what they’re thinking.
00:28:40.424 –> 00:28:45.244
Wegner: And I think a lot of people in a leadership position think that, oh, I’m the leader, I tell people what to do.
00:28:45.244 –> 00:28:48.684
Wegner: And that is really a dumb approach.
00:28:48.684 –> 00:28:53.564
Wegner: Really what you’re doing is you’re getting the best idea and then bringing the best idea forward.
00:28:53.564 –> 00:28:59.064
Wegner: And so we always have a conversation internally and I’ll call somebody and say, hey, I need you to debate me on this.
00:28:59.064 –> 00:29:01.784
Wegner: And what I’m not looking for is for them to agree with me.
00:29:01.784 –> 00:29:03.924
Wegner: What I’m looking for is tell me what I have wrong.
00:29:04.024 –> 00:29:08.284
Wegner: I’ll actually say, hey, tell me what’s wrong with what I’m getting ready to say.
00:29:08.284 –> 00:29:10.444
Wegner: Put your critical hat on.
00:29:10.444 –> 00:29:18.364
Wegner: Because if you’re in a position like Shawn is in where you’re running a company, people can come and just have this yes mentality because Shawn’s the boss.
00:29:18.364 –> 00:29:24.884
Wegner: But if you come in and it’s positioned as, hey, we need to get to the right idea and if your idea is better than mine, we need to know.
00:29:25.644 –> 00:29:27.784
Wegner: I think what Shawn said is really, really important.
00:29:27.784 –> 00:29:36.284
Wegner: What I would add is, and what I want, and I don’t know that I have this, so I might be aspirational, but I really want to be a servant leader.
00:29:36.504 –> 00:29:43.104
Wegner: A lot of people in business, they’re like, oh, you run your own company, so isn’t it great being the boss?
00:29:43.104 –> 00:29:46.864
Wegner: I’m like, no, that’s actually not at all what it means.
00:29:46.864 –> 00:29:56.864
Wegner: What it means is if I have a thousand customers, I have a thousand bosses, and if I have 10 investors, I have 10 more, and if I have 50 employees, I’ve got that to do with as well.
00:29:56.864 –> 00:30:02.964
Wegner: Really what I’m trying to do is I’m trying to be able to serve all those people effectively, and that’s actually the really hard part.
00:30:02.964 –> 00:30:04.764
Wegner: I think about being a CEO.
00:30:04.764 –> 00:30:08.744
Wegner: So I’m thinking about a lot of things, like when I’m working with a customer, how can I serve you?
00:30:08.744 –> 00:30:10.804
Wegner: Because that’s literally how we make money.
00:30:10.804 –> 00:30:17.124
Wegner: If I can serve you and provide value with what we’re building, then you’re going to pay me a lot for that.
00:30:17.124 –> 00:30:19.084
Wegner: There’s an exchange of value there.
00:30:19.084 –> 00:30:26.944
Wegner: If you’re an employee that’s coming to work for TechGrid, I want to be able to provide a great environments when you come in, you want to work and you want to do a good job.
00:30:26.944 –> 00:30:32.684
Wegner: So I’m really thinking about how can I provide the best environment possible for you to do a good job.
00:30:32.764 –> 00:30:40.344
Wegner: So I really want to be and try to be a servant kind of leader.
00:30:40.344 –> 00:30:43.464
Roddy: Yeah, and let me follow up on that and Shawn is going to ask you this question as well.
00:30:43.464 –> 00:30:47.584
Roddy: So like Shawn just talked about the speed which you have to move forward.
00:30:47.584 –> 00:30:51.424
Roddy: If you have a company that’s been established for a while and people are like, well, here’s how the culture is, right?
00:30:51.424 –> 00:30:55.864
Roddy: It’s either open, everybody can exchange or people say, hey, watch what you say.
00:30:56.404 –> 00:31:10.304
Roddy: So I guess, Philip, how do you quickly, as quick as you can, establish that open communication that people feel comfortable telling the owner of the company, the boss that many of them perceive to be, even though you say, don’t call me that.
00:31:10.304 –> 00:31:12.644
Roddy: How do you get them to be able to speak up?
00:31:12.644 –> 00:31:14.124
Roddy: Or is it just the people that you hire?
00:31:14.564 –> 00:31:15.624
Roddy: How do you do that?
00:31:15.624 –> 00:31:21.084
Wegner: I think it’s a combination of all those, but it truly created an environment where you encourage people to disagree.
00:31:21.184 –> 00:31:22.964
Wegner: And that doesn’t mean that you’re all out fighting.
00:31:23.444 –> 00:31:26.584
Wegner: That just means that you have productive disagreements.
00:31:26.804 –> 00:31:39.844
Wegner: If I can go into a meeting with a 25-year-old straight out of school or whatever and have that person challenge me, then I feel like that’s very, very good and very, very healthy in the right kind of way.
00:31:39.844 –> 00:31:42.544
Wegner: And so it’s something that I’ve literally tried to foster.
00:31:42.544 –> 00:31:48.484
Wegner: But just tactically, one way is to speak last in the meeting.
00:31:48.484 –> 00:31:53.464
Wegner: So if you have something that you’re going to weigh in on, you don’t go, hey, let me tell you what I think, and then what do you guys think?
00:31:53.464 –> 00:31:55.964
Wegner: Because they tend to go whatever you think.
00:31:55.964 –> 00:31:57.424
Roddy: So it’s like, hey, Mr.
00:31:57.424 –> 00:31:59.804
Roddy: Wegner, one of the finest, another fine idea from you, sir.
00:31:59.804 –> 00:32:01.024
Wegner: What do you think about this?
00:32:01.024 –> 00:32:03.624
Wegner: And then have that person weigh in first.
00:32:03.624 –> 00:32:07.064
Wegner: I’m not always good at that because I have strong opinions.
00:32:07.064 –> 00:32:09.864
Wegner: But ideally, you would speak last.
00:32:09.864 –> 00:32:10.644
Roddy: Got it.
00:32:10.644 –> 00:32:14.324
Roddy: My old boss used to, in meetings, he would write down smart silence on the agenda.
00:32:14.324 –> 00:32:17.664
Roddy: And then when he wanted to speak, he would just retrace it.
00:32:17.664 –> 00:32:20.564
Roddy: That kept him from jumping in too soon.
00:32:20.724 –> 00:32:28.284
Roddy: So, Shawn, how do you, again, you talked about that Democratic, how do you get people to talk?
00:32:28.284 –> 00:32:28.584
Harris: Yeah.
00:32:28.584 –> 00:32:37.004
Harris: So sticking on the Democratic side, one thing that I know within Coworked that I’ve been really driving home is the fact that we are in this together.
00:32:37.004 –> 00:32:38.584
Harris: Like this is not just about Shawn.
00:32:38.584 –> 00:32:43.524
Harris: This is not just about my other co-founder, Sulak or Ravi.
00:32:43.524 –> 00:32:44.984
Harris: This is about us.
00:32:44.984 –> 00:32:46.044
Harris: We are in this together.
00:32:46.504 –> 00:32:54.064
Harris: And we have a door wide open to emergent ideas and ideas just because of the machines.
00:32:54.064 –> 00:32:58.824
Harris: The very nature of what we’re doing is still novel and new, right?
00:32:58.824 –> 00:33:05.364
Harris: Where we’re building a capability that is probabilistic in nature that is doing work, right?
00:33:05.364 –> 00:33:08.584
Harris: And so one of the things, it’s words.
00:33:08.584 –> 00:33:10.564
Harris: It’s first through words.
00:33:10.564 –> 00:33:12.464
Harris: It’s then through action.
00:33:13.004 –> 00:33:30.584
Harris: And I love what Philip was saying about speaking last, about really making sure that everyone, again, the Democratic side of me, making sure that everyone I hear in meetings, everyone who’s in that meeting, I’m hearing kind of what they have to say.
00:33:30.584 –> 00:33:42.364
Harris: And then for what it’s worth, I’m very good with like, that’s a great showing it, proving it through action that we are accepting of anyone’s idea.
00:33:43.404 –> 00:33:45.044
Harris: And I think that that speaks volumes.
00:33:45.044 –> 00:33:57.244
Harris: And if you’re talking about, I think you might have had a little bit in your question centered around if you’re going into an enterprise or an organization that kind of has a culture established where that may not be the case.
00:33:57.244 –> 00:34:12.684
Harris: Certainly, I think those things that I just mentioned still stand true, but then it just takes time to actually show people that you are genuine with your desire to kind of take in anyone’s idea and that those ideas actually can come in and impact the business.
00:34:12.684 –> 00:34:13.064
Roddy: Got it.
00:34:13.064 –> 00:34:13.524
Roddy: Love it.
00:34:13.524 –> 00:34:24.184
Roddy: The other thing I would add just from my own personal experience, if you find yourself making a lot of statements or offering conclusions, that’s going to shut down conversation because of the title that you have along with it.
00:34:24.184 –> 00:34:34.784
Roddy: But if you’re asking questions and then saying to people, I’m not trying to lead you into something like I’m genuinely looking for your unvarnished opinion here and then praise the people who give a differing opinion.
00:34:34.944 –> 00:34:37.004
Roddy: So, all right, well, that’s a great-
00:34:37.004 –> 00:34:43.784
Harris: There’s a saying along the lines of the question is the answer, right?
00:34:43.784 –> 00:34:47.224
Harris: As a leader, that’s super important.
00:34:47.224 –> 00:34:49.964
Harris: So, I’m plus one on that.
00:34:49.964 –> 00:34:50.864
Roddy: Amen.
00:34:50.864 –> 00:34:56.664
Roddy: So, let’s talk about some experiences from early in your careers that have shaped you both as leaders.
00:34:56.664 –> 00:35:02.584
Roddy: And Philip, first, do you have a story, you have a learning experience that’s really stuck with you and shaped these leaders?
00:35:02.624 –> 00:35:04.744
Roddy: You talked about something like at COVID.
00:35:04.744 –> 00:35:10.664
Roddy: I’m curious if you go back even further, like really early days, you’re like, boy, was this formative and me being a startup leader.
00:35:10.664 –> 00:35:10.944
Wegner: Yeah.
00:35:10.944 –> 00:35:17.844
Wegner: So, I actually, I would, a lot of my shaping, I think, was from my parents and it was before my career.
00:35:18.064 –> 00:35:22.724
Wegner: I didn’t have a tremendous amount of mentors in a traditional sense.
00:35:22.724 –> 00:35:26.784
Wegner: And so, a lot of the things that I took into my career came from my parents.
00:35:26.784 –> 00:35:31.744
Wegner: So, my dad was actually a Baptist minister, and my mom was a school teacher.
00:35:31.964 –> 00:35:35.884
Wegner: And I just remember growing up when my dad would be a minister at a church.
00:35:35.884 –> 00:35:44.384
Wegner: And I remember one thing specifically when—in a small church environment—I don’t know if you guys are churchgoers or not, it doesn’t matter.
00:35:44.384 –> 00:35:49.344
Wegner: But in this kind of environment, you have essentially elders that vote on the minister.
00:35:49.344 –> 00:35:59.044
Wegner: And I remember being in my parents’ green station wagon with the wood paneling on the side and waiting in the car while the church was voting on my father.
00:36:00.064 –> 00:36:09.404
Wegner: And it was just like this thing where I watched my dad serve, and then the people that he was serving were basically voting on whether they were going to keep him or not.
00:36:09.404 –> 00:36:11.004
Wegner: And that was a really kind of a pitiful thing.
00:36:11.004 –> 00:36:15.904
Wegner: But what was pitiful for me is my dad saying, I don’t think I’m supposed to go anywhere.
00:36:15.904 –> 00:36:22.824
Wegner: Like he basically was saying, I think that I’ve been called to be here, and until I feel like I’m not, I’m not going to go anywhere.
00:36:22.824 –> 00:36:33.424
Wegner: And it just filled me with this—like looking back, there’s a will that my dad had where I watched him work and serve.
00:36:33.424 –> 00:36:36.004
Wegner: And then he would not waiver on that.
00:36:36.224 –> 00:36:39.084
Wegner: And for whatever reason, I think that’s really embedded in me.
00:36:39.084 –> 00:36:43.864
Wegner: And it’s just like a character thing or a not quit thing.
00:36:45.004 –> 00:36:50.404
Wegner: And so as long as I feel like I’m doing the thing that I’m supposed to be doing, I’m not going to stop.
00:36:50.524 –> 00:36:53.664
Wegner: And that was something that my parents kind of gave me.
00:36:54.824 –> 00:36:58.164
Roddy: Great story, great that you drew that from that experience.
00:36:58.164 –> 00:37:03.544
Roddy: Shawn, what’s an early learning experience that you want to share that’s been really influential on you as a leader?
00:37:03.544 –> 00:37:16.184
Harris: Yeah, if I could just double down on the idea of like my parents, specifically my father, was so instrumental in my development.
00:37:16.964 –> 00:37:19.884
Harris: As a curious soul, he fed me.
00:37:19.884 –> 00:37:31.304
Harris: He was actually by my side in terms of being like the same sort of person who was willing to take in that new things, to have a growth mindset.
00:37:31.304 –> 00:37:38.024
Harris: And I think it’s just served me so well in life as a foundational element to who I am.
00:37:38.024 –> 00:38:06.684
Harris: I would say secondarily, my experience in serving in the Army, being responsible for, you know, operating a tank, being responsible for the people who were under my purview, like I think was also a time of understanding what it meant to be a part of something bigger than me.
00:38:07.904 –> 00:38:42.264
Harris: And at the same time, learning for what it’s worth, how to manage to, if you will, the commander’s intent, to manage to having a plan, but also making it such that individuals know the right things to do, is something that is very, it’s a part of my way of working today, with all of our team members, co-founders, partners, customers, and certainly will be beyond.
00:38:42.264 –> 00:38:49.704
Roddy: And it sounds like because, so thank you for that, Shawn, and it sounds like because of both of your experiences, those are just now how you’re wired, right?
00:38:49.704 –> 00:38:54.244
Roddy: Like you don’t even have to think about it secondarily, and other people don’t have that shared experience.
00:38:54.244 –> 00:38:57.744
Roddy: And sometimes you’re probably looking like, geez, why aren’t they behaving in this way?
00:38:57.744 –> 00:39:05.964
Roddy: But it seems like it’s that, you know, that foundation really at your core, that just causes you to operate like you do every day in a leader as a startup.
00:39:05.964 –> 00:39:06.644
Harris: Got it.
00:39:06.644 –> 00:39:07.704
Harris: You got it.
00:39:07.704 –> 00:39:08.104
Roddy: Excellent.
00:39:08.104 –> 00:39:15.844
Roddy: So one of my goals in 2025 is to be brave enough to ask this next question to every leader who’s appearing on the Trusted Advisor and talk in leadership.
00:39:15.844 –> 00:39:19.764
Roddy: So and Shawn, if you can be brave enough to go first with this.
00:39:19.764 –> 00:39:25.424
Roddy: So you operated a tank, so we know you passed this test before.
00:39:25.424 –> 00:39:30.644
Roddy: So can you tell us about a mistake that you made as a leader and what you learned from it?
00:39:30.644 –> 00:39:36.364
Roddy: Again, it could be recent, it could be a long time ago, it could be a colossal disaster, it could be just where you fell short.
00:39:36.364 –> 00:39:38.884
Roddy: So again, a mistake you made and what you learned from it.
00:39:40.544 –> 00:39:52.444
Harris: Yeah, I guess as you’re navigating through, I say enterprise, there are classically three different lenses that you’re working through.
00:39:52.444 –> 00:40:01.064
Harris: One is the Fortisworth political lens, there’s the strategic and then there’s the cultural.
00:40:02.364 –> 00:40:20.564
Harris: I think that as a leader, I have, I can think of some vivid memories that I won’t be specific on, but I can think at times when I have stumbled the ball on the political, right?
00:40:20.564 –> 00:40:35.864
Harris: Truly understanding the soft power that’s at play, the individuals who are, for what it’s worth, truly in control of a situation is not necessarily positional.
00:40:37.164 –> 00:40:41.464
Harris: And I feel like I’ve gotten that wrong.
00:40:41.464 –> 00:41:34.464
Harris: As an individual who, any individual who is trying their best to lead from where they are, I think keeping a sharp perspective, keeping an open mind to these factors, to these lenses, again, the political, the strategic and the cultural, where the political can be aligned to things where I just, I, I, maybe I, the structural, the structure of the enterprise is not necessary, the lines of power in the enterprise, that culturally, there are the ways that things happen within an organization that have nothing to do with what’s in the, you know, employee handbook and strategic, making sure that you are aligned to what the company is trying to accomplish, right?
00:41:34.924 –> 00:41:42.204
Harris: There are three key things that would ask individuals to kind of hold close to as they’re trying to engage in an enterprise.
00:41:42.204 –> 00:41:45.884
Roddy: And political people think like, oh, politics, that’s bad.
00:41:45.884 –> 00:41:55.324
Roddy: But are you talking about when you say political just in terms of like the whole people dynamic, like being people smart, being people interaction smart, and how all those dynamics work?
00:41:55.324 –> 00:41:57.544
Roddy: Just to my understanding that correctly?
00:41:57.604 –> 00:41:58.244
Harris: Absolutely.
00:41:58.244 –> 00:42:08.224
Harris: But there is a, you know, people have agendas, and you need to be very thoughtful about what is the motivations of others.
00:42:08.224 –> 00:42:10.804
Harris: And what I was getting at for me, I’ve gotten that wrong.
00:42:10.804 –> 00:42:11.844
Roddy: Okay.
00:42:11.844 –> 00:42:12.484
Roddy: Got it.
00:42:12.484 –> 00:42:13.804
Roddy: No, thank you for that.
00:42:13.804 –> 00:42:17.424
Roddy: Philip, you want to share with us the time you made a mistake as a leader?
00:42:17.484 –> 00:42:17.864
Wegner: Mistakes?
00:42:17.864 –> 00:42:20.004
Wegner: How many times, how much time do we have?
00:42:21.304 –> 00:42:34.224
Wegner: So the ones that stick like the top of my now is, I think if you’re leading a company, hopefully that means you’re some side of visionary, if you will, and you see the future, or you know where your company is going to go.
00:42:34.224 –> 00:42:36.484
Wegner: Specifically, you’re building a product like Shawn or myself.
00:42:36.484 –> 00:42:40.184
Wegner: Hopefully, you’ve got a vision for what that product needs to go.
00:42:40.184 –> 00:42:44.564
Wegner: And what you probably also are, and what I also am, is you’re an optimist.
00:42:44.564 –> 00:42:46.804
Wegner: And so you’re a visionary and you’re an optimist.
00:42:46.944 –> 00:42:51.084
Wegner: And I believe if you’re a visionary and optimist, that’s a recipe for bad decisions.
00:42:51.084 –> 00:42:57.904
Wegner: And for me, specifically, what that means is, oh yeah, we’re going to be there in six months.
00:42:57.904 –> 00:43:04.644
Wegner: So let me go ahead and start hiring people now that I know we’re going to need to have, because it’s only going to take us six months to reach that goal.
00:43:04.644 –> 00:43:08.844
Wegner: And so for me, what I’ve consistently gotten wrong is the timeline.
00:43:08.844 –> 00:43:13.104
Wegner: Because in my mind, again, I can see the future, what I think is correct.
00:43:13.104 –> 00:43:15.584
Wegner: And then I can also oversimplify what we have to do.
00:43:15.864 –> 00:43:18.684
Wegner: And then I can say, oh, we’re going to be there faster than we are.
00:43:18.684 –> 00:43:32.664
Wegner: And so what I think has to happen when you’re like that, which most CEOs probably are, you got to put people in your purview that can conflict your view.
00:43:32.664 –> 00:43:38.864
Wegner: So even somebody that has just a, hey man, are you sure this is the right?
00:43:39.244 –> 00:43:43.644
Wegner: You’ve been saying that, and it’s taken us a year and a half to build this.
00:43:44.584 –> 00:43:47.544
Wegner: So just have somebody to double check really your decisions.
00:43:47.944 –> 00:44:01.964
Wegner: And then for me specifically in a startup environment, letting the business force me to do things in some instances, like hire more people, let the revenue force me to do something, don’t forecast what needs and then hire in advance.
00:44:01.964 –> 00:44:05.724
Wegner: And different people think different things on that, what I just said.
00:44:05.724 –> 00:44:10.704
Wegner: But that’s the approach that I’m taking, is I’m letting the business force me into it.
00:44:11.764 –> 00:44:13.484
Harris: Yeah, I agree with this.
00:44:13.524 –> 00:44:14.264
Harris: I’m sorry, I agree.
00:44:14.344 –> 00:44:15.844
Harris: I was going to say, I agree as well.
00:44:17.544 –> 00:44:18.704
Harris: There is a difficulty.
00:44:18.704 –> 00:44:27.924
Harris: It’s hard to balance allowing yourself to be in a situation where now you need to do something, where it’s trying to act ahead of it.
00:44:27.924 –> 00:44:37.864
Harris: But 100% in a startup, you need to be in a position where, oh my God, I am now in that situation, time to act is the way you have to operate, for sure.
00:44:37.864 –> 00:44:41.204
Roddy: And that’s where the importance is, the speed that you can move is an organization, right?
00:44:41.204 –> 00:44:45.104
Roddy: Because if you can’t get, you can get too far ahead of it and then screw things up.
00:44:45.104 –> 00:44:49.104
Roddy: But if you’re too slow to react, then you’re going to be far behind.
00:44:49.104 –> 00:44:55.424
Roddy: So that’s what it sounds like what you guys are saying is, you got to stay close to the situation and then be ready to move when the situation calls for it.
00:44:55.424 –> 00:44:56.064
Roddy: Yep.
00:44:56.064 –> 00:44:57.024
Roddy: Right.
00:44:57.024 –> 00:44:57.544
Roddy: Excellent.
00:44:57.544 –> 00:45:03.004
Roddy: So we’ve only got a couple minutes left and I definitely want to get an answer to this question.
00:45:03.004 –> 00:45:05.984
Roddy: And so, and then Philip, if you can go first.
00:45:05.984 –> 00:45:14.044
Roddy: I’m curious, some leaders that you’ve looked up to as mentors who’ve helped you shape your leadership approach, I guess, in addition to your parents, you both already talked about that.
00:45:14.044 –> 00:45:20.204
Roddy: And I’m curious, like, what did they say, what did they do that’s had a lasting impact on you?
00:45:20.204 –> 00:45:26.904
Roddy: Because I’m sure a lot of people listening to this are future leaders looking for mentors, and a lot of other folks are mentors, and I want to see what advice they can offer.
00:45:26.904 –> 00:45:29.984
Roddy: So who’s somebody you looked up to and what did they say or do?
00:45:29.984 –> 00:45:36.504
Wegner: Well, currently, I really go up to Arne Bellini, who’s on the board, but I’ve only had a relationship with him for a year and a half.
00:45:36.504 –> 00:45:48.084
Wegner: But I’ll just say that if you’re ever able to connect with somebody that is 20 years ahead of you, literally in every way, or even five years, that’s so valuable.
00:45:48.084 –> 00:45:50.624
Wegner: I was talking about earlier about the mistakes that I made.
00:45:51.804 –> 00:45:58.924
Wegner: I’m running a lot of things through somebody like Arne, and Arne is fixing my perspective.
00:45:58.924 –> 00:46:00.364
Wegner: But early in my career, I didn’t have that.
00:46:00.364 –> 00:46:01.624
Wegner: I didn’t have a lot of mentors.
00:46:01.724 –> 00:46:06.964
Wegner: I actually tried to establish them and I was never able to do it.
00:46:06.964 –> 00:46:15.784
Wegner: What I did is what I see behind you is I read a lot of books, and I got a lot of knowledge from reading like you do, voraciously.
00:46:15.784 –> 00:46:19.704
Wegner: That’s literally the things that we’re doing now, or things I learned five years ago.
00:46:19.704 –> 00:46:30.824
Wegner: Then the other thing that I did that I think is very valuable and relevant to you is, I think associations and getting around other leaders that are doing the same thing you’re doing is so valuable.
00:46:30.924 –> 00:46:35.124
Wegner: Literally, it’s not necessarily a mentor, it’s really a peer.
00:46:35.124 –> 00:46:36.984
Wegner: This isn’t a plug for you, I know that’s what you do.
00:46:37.504 –> 00:46:50.664
Wegner: But literally, that’s where as I was growing my company, as an MSP, that’s where I was learning a lot is in these peer environments where I was meeting with another CEO, maybe their company was way larger than mine.
00:46:50.844 –> 00:46:52.464
Wegner: So I could learn a lot.
00:46:52.564 –> 00:47:03.244
Wegner: And what’s been great about a lot of associations is that people are very, very open and sharing even if they are technically a competitor in another market.
00:47:03.244 –> 00:47:06.684
Wegner: So I think those are all really valuable strategies.
00:47:06.684 –> 00:47:07.184
Roddy: Excellent.
00:47:07.184 –> 00:47:07.584
Roddy: Thank you.
00:47:07.584 –> 00:47:10.704
Roddy: Shawn, who are some leaders you’ve looked up to?
00:47:10.704 –> 00:47:11.884
Harris: Yeah, I’ll be honest.
00:47:12.504 –> 00:47:15.584
Harris: I am going to bring it back to family and say my brother.
00:47:15.584 –> 00:47:21.064
Harris: My brother is an executive at a very large company where he runs HR for the company.
00:47:21.404 –> 00:47:31.724
Harris: And the thing that he’s given me is his perspective on like a first principles way of thinking about his behavior and individuals.
00:47:31.724 –> 00:47:34.944
Harris: That has been incredibly helpful.
00:47:35.804 –> 00:47:49.724
Harris: He may not necessarily know it, but his perspective on the world from this rooted, you know, what is the behavioral things that an individual is trying to, what are they trying to achieve?
00:47:49.784 –> 00:47:51.564
Harris: What is their motivations?
00:47:51.564 –> 00:47:55.024
Harris: Has been so valuable for me.
00:47:55.024 –> 00:47:59.884
Harris: And so I’d say like, yeah, I definitely like lean on him quite a bit.
00:47:59.884 –> 00:48:04.604
Harris: And I’m blessed to have him as a brother in my life.
00:48:04.604 –> 00:48:12.504
Harris: And then as Philip said, reading, read, read, read, read, read, read, read, read, read some more.
00:48:12.504 –> 00:48:14.504
Harris: Yeah, like it’s like, what do they say?
00:48:14.504 –> 00:48:15.564
Harris: Reading is fundamental.
00:48:15.564 –> 00:48:18.004
Harris: There’s no if ands or buts about it.
00:48:19.944 –> 00:48:25.564
Harris: You may not per se remember everything that was in it, but there’s nuggets that will stay with you.
00:48:25.564 –> 00:48:34.384
Harris: And those nuggets create adjacencies and adjacencies yield the ability to innovate and think differently about a given moment.
00:48:34.384 –> 00:48:44.264
Harris: And so I think my brother’s ideals around first principles, like being able to just consume things that construct then mental models and how you look at the world.
00:48:44.624 –> 00:48:53.764
Harris: So you can go and don’t be reactive to a moment, but be able to step back and go, I know what’s going on here, is just incredibly important for me.
00:48:53.764 –> 00:48:54.244
Roddy: Thank you for that.
00:48:54.244 –> 00:49:01.504
Roddy: And I’ll tie both of your answers together because the first time I engaged with the RSPA was 2006.
00:49:01.504 –> 00:49:05.324
Roddy: I was president of a magazine publishing company.
00:49:05.324 –> 00:49:09.764
Roddy: And I happened to connect with Mark Olson there, who’s now the retired president of APG Cash Shore.
00:49:09.764 –> 00:49:11.124
Roddy: I was in my first year as president.
00:49:11.124 –> 00:49:13.524
Roddy: He was in his 20th year, just like you said, Philip.
00:49:13.824 –> 00:49:14.904
Roddy: And I connected with him there.
00:49:14.904 –> 00:49:16.644
Roddy: And I was like, tell me, what’s a secret?
00:49:16.644 –> 00:49:22.424
Roddy: And that was his big thing, was read and interact with a lot of people who have been there and done that before.
00:49:22.424 –> 00:49:27.384
Roddy: And Mark is still a really, really good friend and really helped me in those terms.
00:49:27.384 –> 00:49:31.964
Roddy: Like you said, somebody’s been down that path before and they can share their stories and their experiences.
00:49:31.964 –> 00:49:34.864
Roddy: And again, Mark was board chair of the RSPA as well.
00:49:34.864 –> 00:49:36.744
Roddy: So I’ve got to plug the association.
00:49:36.744 –> 00:49:38.904
Roddy: So all right, we’ve only got a couple of minutes left.
00:49:38.904 –> 00:49:42.304
Roddy: And so I want to get your final advice for the audience.
00:49:42.404 –> 00:49:43.504
Roddy: Shawn, starting with you first.
00:49:43.504 –> 00:49:58.084
Roddy: And if you can put it within 60 seconds, say you’re in an elevator ride and you’ve got a small business leader, somebody who’s maybe a startup leader thinking about doing that, what advice would you give to them as you’re going from floor one to floor 37?
00:49:58.084 –> 00:50:00.604
Harris: Yeah, focus on putting yourself around good people.
00:50:00.604 –> 00:50:26.724
Harris: I think in the world that we live in where there’s this disconnect that’s occurring, where there’s so much digital medium between us all, I think it’s critically important to put yourself around people who are good people, smart people, people who are just however you want to characterize it, better than you and let them help to level you up to them and then put yourself around more people that are better than you.
00:50:26.724 –> 00:50:35.044
Harris: And so I think just doing that and then nurturing those relationships is number one to me.
00:50:35.044 –> 00:50:35.904
Roddy: Excellent.
00:50:35.904 –> 00:50:37.184
Roddy: Philip, what would be your advice?
00:50:37.484 –> 00:50:39.744
Roddy: So we got out to 437 with Shawn.
00:50:39.744 –> 00:50:42.804
Roddy: Now that person has to go back down to your writing with them from 3701.
00:50:42.804 –> 00:50:44.964
Wegner: I was literally going to say the same thing that Shawn just said.
00:50:44.964 –> 00:50:49.224
Wegner: So I think surrounding yourself with the right people is so important.
00:50:49.224 –> 00:50:52.244
Wegner: And I think that applies to a lot of different parts of the business.
00:50:52.244 –> 00:50:58.124
Wegner: So if you’re building product, I think surrounding yourself with the customers you’re building a product for, helps you build a better product.
00:50:58.124 –> 00:51:03.704
Wegner: And if you want to be a better leader of a company, you want to be with other leaders who’ve led other companies and done a good job.
00:51:04.084 –> 00:51:10.244
Wegner: As humans, we tend to like people that are at our level or below because that’s what makes us comfortable.
00:51:10.244 –> 00:51:16.864
Wegner: But if you get in a room with people that are way above your level, all of a sudden, it’s pushing you to be something that you’re not.
00:51:16.864 –> 00:51:18.904
Wegner: And that is uncomfortable.
00:51:18.904 –> 00:51:22.984
Wegner: But that, I think, is what helps people rise to the next level.
00:51:22.984 –> 00:51:23.524
Roddy: Amen.
00:51:23.524 –> 00:51:24.464
Roddy: Very well said.
00:51:24.464 –> 00:51:25.204
Roddy: Very well said.
00:51:25.204 –> 00:51:27.744
Roddy: Well, that does it for this episode of The Trusted Advisor.
00:51:27.744 –> 00:51:34.804
Roddy: If you enjoyed our discussion, be sure to subscribe to the RSPA YouTube channel and The Trusted Advisor podcast so you never miss an episode.
00:51:34.804 –> 00:51:40.004
Roddy: Before we go, big thanks again to Philip Wegner and Shawn Harris for sharing their wisdom with us today.
00:51:40.004 –> 00:51:45.384
Roddy: Thanks also to RSPA Marketing Director Chris Arnold for his production work, Joseph McDade for our music.
00:51:45.384 –> 00:51:48.324
Roddy: And last but not least, thanks so much to you for listening.
00:51:48.324 –> 00:51:55.744
Roddy: Our goal at the RSPA is to accelerate the success of our members in the retail technology ecosystem by providing knowledge and connections.
00:51:55.744 –> 00:51:59.464
Roddy: For more information, please visit our website at gorspa.org.
00:51:59.864 –> 00:52:03.224
Roddy: Thanks for listening and goodbye everybody.
