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Pivot, adapt, pivot.

As entrepreneurs and business owners, pivoting and adapting is in our DNA. But that doesn’t mean it’s always a breeze. Determination, hard work, and grit can help us navigate and overcome even the most difficult pivots in our careers—and lives.

As a CEO, it's been nice to have been forced through that because I felt like I would have always been a pioneer and my kids would’ve said ‘ok boomer, not everyone’s gotta be at work.

Matt BrownCEO of ThumbStopper


Navigating Pivots with Hard Work, Determination, and Grit with Matt Brown

Katie Hankinson (00:02): Hi, I’m Katie Hankinson.

Mickey Cloud (00:04): And I’m Mickey Cloud, and welcome to Building While Flying, a new podcast from The Sasha Group where we interview business leaders about how they tackle challenges, stay resilient and navigate ever-changing skies.

Mickey Cloud (00:22): Welcome, Matt Brown, to Building While Flying. Matt is a 20+ year serial entrepreneur across the telecommunications and IT ecosystems, and currently serves as President and CEO of ThumbStopper, a SaaS social media marketing company based out of Tampa, Florida. We’re definitely going to dive into kind of your entire entrepreneurial journey, but would love to maybe at the top just allow you the chance to give a little more context on ThumbStopper and your current venture.

Matt Brown (00:48): Yeah, absolutely. And thanks, Mickey, for having me. Over the last 20 years, as you’ve mentioned, I’ve kind of been across the gamont of starting off as an entrepreneur in the internet hosting space, believe it or not, early on back when you heard those crazy noises and, “You’ve got mail,” from AOL. So, if you can remember those times, and maybe you’re too young, but… That’s right.

Mickey Cloud (01:11): Dial-up? Yeah, I’ve got that.

Matt Brown (01:14): Absolutely. As Gary himself says he knew that was special, that sound, and that was going to change some things. So, if you fast-forward through a lot of that stuff and where we’re at today with ThumbStopper is over the last 20 years, I’ve been really fascinated with digital marketing in general, it’s changed flavors every year since I’ve been doing this and it continues to get more complex really even though a lot of things online are getting easier, and with that complexity, we’re really trying to deliver value at the small retailer level. Where I’ve been as an entrepreneur before is at the retail level, and some of the places I couldn’t compete is because I didn’t have large marketing budgets. So, I’ve kind of become obsessed with how, ultimately, we would help connect retailers on the cloud and find consumers that were interested in purchasing their goods and services.

Mickey Cloud (02:10): Love having serial entrepreneurs like yourself on the podcast because your journeys are rarely linear, so you kind of fast-forwarded through that, so I would love if you could maybe even just wind us back and give us kind of that comic book 001 story and a bit about what led you to where you are today.

Matt Brown (02:26): Yeah, absolutely. So, if I were going to rewind all the way back, I had a short stint in college and I got a call from a very good friend of mine, who talked to me about becoming a technical recruiter and what an opportunity it would be, and he’s moved to Miami and wouldn’t believe how fun Miami would be, and he talked me out of college mid-semester into dropping out and taking this career move, and I realized quickly that there was something different about me and not being able to blend into corporate America, and so it was my short corporate job that had me dealing with technical people because I was a technical recruiter. So, I was finding developers for Royal Caribbean and cruise lines and different large companies that had tech projects, and what I learned early on is that I really liked this world of developers. They were this unique cast of people and characters that I got along with, and to me, it was a little bit like the military, there were all types of people, and I was amazed by that. I learned to talk the lingo, I picked up on technology.

Matt Brown (03:41): That was a short career stint. I moved to Tampa Bay, where I met my wife and over 20 years ago now, and was looking to get into business for myself and I loved selling on eBay. I was infatuated with eBay, and so I opened up these eBay stores and my claim to fame in 2005 is when the 40 Year Old Virgin featured one of our eBay drop-off stores, if you remember the scene, “I just want to buy the boots.” So, that’s my claim to fame as an entrepreneur, but the… So, back to the business of helping businesses and retailers get that inventory online started with those eBay drop-off stores and serving businesses, which ultimately led me back to hiring developers to build software platforms as we tried to scale that business, and here we are today with three different software businesses under the roof serving different verticals, if you will.

Mickey Cloud (04:47): It’s amazing. I was not expecting the Judd Apatow appearance on the podcast today, but love it. Well, I guess you’ve been at the helm of multiple startups, and you’ve got kind of entrepreneurship in that thread of that story. What was your immediate gut reaction when you heard we were launching a podcast called Building While Flying?

Matt Brown (05:10): You hear the terminology all the time as sometimes running a business is like building a plane and flying it at the same time, so that’s what struck me initially, but we could go with so many angles about what that means, but I certainly… One of my greatest mentors used to tell me that I was a one-armed paper hanger, and that I always needed to find help in a certain department or it’s time to find a CEO for the company, etc, etc. But I wasn’t sure what to expect, and I listened to a couple of them, and it’s just very interesting. And as you know, we’re a big fan of The Sasha Group, so I was excited to attend.

Mickey Cloud (05:50): Yeah. Breakdown the one-armed paper hanger analogy for me.

Matt Brown (05:55): Well, I don’t know that I ever asked him to what the definition of that meant, but the visual to me [inaudible 00:06:02] everything that it said and that is if you can imagine having one arm to hold the paper and get the paper clip open to get the paper inside it, that is… Maybe he was telling me that I was trying to do something that might not be doable.

Mickey Cloud (06:18): Yep. Yep. Well, we’d love to dive into to your concentration on local retailers and what you’re building for them now, and so ThumbStopper is a social media SaaS platform that helps local retailers and kind of enterprise brands. When you launched the company, did you have kind of the local retailers in mind and you saw it as an opportunity to connect with enterprise brand, I guess? Where did the kind of the genesis for the idea come from and how is it kind of evolved?

Matt Brown (06:49): Yeah, absolutely. Our LotVantage product is hopefully self-explanatory. It’s anything that you would have on the lot in car dealers, powersports, marine RV, commercial trucks, farm and garden trailer dealers, they all have what they refer to as lot. So, whatever was on the lot, LotVantage would take up and help push that inventory across multiple platforms automatically, and what we realized once we got to where we had 7 or 8000 of these retailers across North America is how disconnected the manufacturers were with the retailers that sold their products, and we could see that manufacturers had digital assets for advertising their products available online, but the retailers were disconnected with that. And that’s what I wanted to fix when we launched ThumbStopper out of LotVantage in 2016, is that I really wanted, at this point, to approach the manufacturers and bring them in harmony with what the retailers were doing.

Matt Brown (07:55): And it wasn’t as important when I was dealing with the inventory that was on their lot, where it became important is when we transferred our focus over to social media, and when social media really started to shift how it was integrating itself into commerce, and that’s where there was a huge disconnect, as you saw brands across the world, big social media presences, but where they really needed to be focused was getting the presence in tune with the retailer social media pages that sold that inventory the same way that they did on the lot. So to me, the Facebook page, the Instagram posts, those are those digital lots now for organic content and inventory.

Mickey Cloud (08:39): So, take me through the… Because it sounds like you’ve got the big manufacturers, which are these large…. And the types of industries you just described, the car lots, the powersports, the farm and garden, those things. And then obviously the problem of the local retailers and optimizing and using digital media to sell and to drive foot traffic to their lots. Are you approaching kind of the enterprise-level clients first, are you going to the local retailers? I guess, how are you making sure that those are being connected and you’re helping to solve that issue?

Matt Brown (09:22): That’s a great question, and what we found… So, we went after enterprise initially, and we wanted to get the attention to the manufacturers, especially in verticals where they had co-op money, where they had money that was used to help advertise services at the local level for the dealers, and what that co-op money was accustomed to was local TV commercials and radio ads and newspapers, and what they weren’t accustomed to is this digital connection of things that were important and something started to change in like 2016-ish, and that was as you would search for a small business on Google and the expected results were that you would find out about that business’s location, or the reviews, or you would find their website, or you would find a number of things.

Matt Brown (10:08): In 2016, what became dominant was how your Facebook fan page became the number one search result. So, what was happening is you had an entire vertical industry focused on their website, and totally ignoring their social media presence, and the consumers were landing there because of the Google search results. So, it became apparent the same way that you needed up-to-date inventory on your website, you needed up to date inventory and organic content on your social media pages. And so maybe if I were trying to laymen and down a little bit, that’s how I would describe it.

Mickey Cloud (10:47): Is the focus of the business still on the enterprise level, or have you also I guess… I guess at what point did you realize maybe you could also help the local retailer side?

Matt Brown (10:56): Yeah, absolutely. So, really it’s always been about the retailer, even as the enterprise focus. The focus on the enterprise was instead of trying to market to an individual retailer one at a time, to me that wasn’t going to scale, I’ll be long gone and retired before I could ramp a couple 100,000 retailers on to a connectivity. So if I went to enterprise, I knew it would help get me a certain percentage of customer penetration in a fashion that I could never do you like one-offs, if you will. That’s why it had taken 15 years to build LotVantage to the point where we had several thousand retailers on that platform. So, that was the plan of attack.

Matt Brown (11:39): However, what we realized is that there were three levels of what an enterprise brand would achieve with us getting a hold of them. One, they would be fully engaged with it and understand it, and that means we’re all in, connect as many retailers as you can for us. You’re getting impressions on our brand at the local level. We totally get it. So, that’s fully engaged. Then there’s semi-engaged, semi-engaged is, “Oh, wow. We really like it. However, we may not have co-op money for this program, but I’ll tell you what, we’ll get behind it. We’ll put our name on it. We’ll communicate with our retailers about it, and maybe even we’ll share in the cost of the product,” and that’s semi-engaged. Disengaged with a brand, and we have many of those, those are brands that have verticals that got decimated in COVID-19, and they’re saying, “All spending is cut.” We know those verticals and sometimes we even play pro bono in some of those, trying to get the connectivity and help them out.

Matt Brown (12:44): But if a brand is disengaged, we also have it to where we can organically consume the content from the brand, and the retailers can sign up today. So, the bicycle vertical is an example of where we’ve given up and said, “Here’s what we found out about bicycles.” The opposite of COVID-19, you couldn’t buy a bicycle. As a matter of fact, I helped D-Roc locate a bicycle for his parents during COVID-19 because you couldn’t find a bicycle. And so what we gave up on the enterprise side, and what we did is, we put all the enterprise brands into one brand manager and then we started marketing to what I said I wasn’t going to do, but I wanted to prove that if we could get a number of retailers on, then when we call the enterprise brand, we can already say, “Look, we have 150 a year retailers,” and that was a much easier conversation, and it seems to have moved them from disengaged brands to semi or fully-engaged brands. So, we’ve been all over the gamut with how we’ve approached enterprise and how we ended up at the retailer service level.

Mickey Cloud (13:52): I’m really fascinated by the business model because you’ve got to, at the end of the day, serve kind of two audiences, the enterprise brands and the local retailers, and the sales approach, the how you speak to them is got to be different in some ways because of just the different kind of processes and the different scale that they’re at, and so I was curious, in some sectors you’ve pivoted and you’ve gone directly to the retailers, and others, you’ve been able to continue to go after the enterprise brands. So I’m curious, just what are the some of the macro lessons you’ve taken away from this two prong approach that you’ve got?

Matt Brown (14:27): No, it’s a great question, and there’s a few things to unpack here. One is man, the enterprise conversations are way different. If you’re manufacturing outdoor power equipment, boy, the retailers in rural America with… When we went to the shows back before COVID-19, we would hear things like, “We don’t need social media. We’ve been doing it for 25 years,” and one of the things that came from that as an adjustment was really understanding the retailer, again, at the macro level, and boy, not only do we need to get them a connection, but we need to help them establish their social media presence where that brought on a little bit of overhead from an account management standpoint. One of the things that we launched was what we called the Account Growth Managers to help reach out to retailers to come onto a program, and what we learned as we brought on a fully-engaged enterprise brand is that those Account Growth Managers, by calling those retailers that were fully-engaged, we have 80% of their retailers that will onboard in a fully-engaged program versus maybe 15% of the retailers that might engage with a disengaged program.

Matt Brown (15:43): So, as we started to get some of that data and statistics, it’s changed the dynamics of the conversations about why a brand should be fully-engaged and what their expected ROI could be. But back to your using terminologies and acronyms, especially in the marketing world… And let me tell you, us tech people are the worst at it. When I hear people say things like IoT, that had to come from the bankers, nobody would… Or the word cloud is why would you ever make a terminology of cloud unless you want it to confuse the rest of the world and belittle them. Marketing does a lot of that too with their acronyms. We’re all guilty of it kind of in our segments of verticals, but it has in lot of ways the things that we learn when we’re… Opposite contrast retailer versus the enterprise.

Mickey Cloud (16:35): Yep. I think another complication in your world probably comes from the fact that you’re building for platforms that are themselves all the times changing. So, you’re building technology for companies to better utilize Facebook, Instagram, Google, Snapchat, etc. So how do you as ThumbStopper, as the tech solution on top of these tech platforms, keep up with kind of the fact that they change all the time, integrating new features or just changes to platforms while keeping clients not confused or just updated on kind of the ways these platforms are engaging.

Matt Brown (17:14): I’ll tell you, from a barrier to entry, it’s wonderful thing to be in once you’re in the ecosystem. From a daily grind, it never stops. And back in the early days, Craigslist was the perfect analogy of a company that turned my hair gray at a very early age. And they had no API, and they didn’t want technologies… Their terms of use were translating some religious book. My attorneys couldn’t figure it out, and my internal operational people couldn’t figure it out. So we were stabbing in the dark, and a lot has changed since then, and now we fast forward into the social media giants that are under constant political pressure. They’re making changes with organic content, and who the terrorists are involved in some of this nonsense that happens online, and we get the shrapnel from that. It’s already tough enough in the business, maintaining the APIs and the current code base, and the amount of competition that is doing different things and changing the AI, but on top of it, the shrapnel over the last few years from the political consequences on social media has been a bear.

Mickey Cloud (18:32): Yeah, I know. Because you’re at the mercy of the platforms, right? It’s the great kind of challenge, I think, of when you’re building SaaS in this way, but there’s still that need for it.

Matt Brown (18:45): And companies like Google are trying to become social platforms again with Google My Business. It’s one of the new products that we’re getting ready to launch, and so now you’re looking at a search platform that wants social updates at the local level for the businesses. So, it’s just never-ending, and I’ll tell you, it’s a young man’s sport today.

Mickey Cloud (19:08): That’s super true, but what those gray hairs and experience give is that experience base to go back on. And so I guess, I’m curious, you’re a serial entrepreneur, you’ve been through a couple different ventures. I’m sure you’ve had the high highs, and I’m sure you’ve had the bruises and scratches along the way. I guess what’s the biggest scar you’ve got from a tumble, and what did it teach you?

Matt Brown (19:37): The high highs and the bruises, they come every week, especially if you’re really continually trying to push the boundaries, and I really like what I do. The biggest scar that I have, the biggest nightmare that I had was December 2013, Craigslist released that they were going to start charging for advertising, and they were going to do it in four days, and 40% of my revenue as a company went away overnight. And I was faced with many challenges. One was, okay, we’re going to go from a profitable company to burning a lot of cash, and was I ready for that? Two was, was I able to solve the riddle of within a few business days of building a transaction platform to handle collecting the money needed from the individual advertisers, and then how do I hand that off to Craigslist with no interface? So, that was an eye-opening moment for me that as an entrepreneur, I had always preached, “Focus. Focus. Focus. Focus. Focus.”

Matt Brown (20:43): I became focused on a singular point of being the 10,000 pound gorilla. I still think today I’m Craigslist’s largest provider of listings on the planet, and we became wide-focused, and that was tough for me as a CEO because I always felt like we were the best at class, and I didn’t want multiple platforms to be mediocre at. And so as we’ve added platforms, it’s been an obsession to kind of continue the same quality of product that we always had in Craigslist. I didn’t know if we were going to solve it, and it ended up six months to recuperate that 40% of revenue that took me 11 years to build on. And it was brutal. I mean, it was just a life-changing event.

Mickey Cloud (21:35): Yeah. No, I mean, that underscores kind of that previous question on how do you keep up with the platforms, especially when they’re going to make that kind of change, and you’ve got four days to prepare for it. I imagine when you have something like that that you’re going through, the team around you really matters, and that’s something that as I’ve gotten to know more about you and your company is that one of the reasons our team loves working with you is kind of your passion for team and culture building. A huge component, in my mind, of team and culture building is talent attraction and talent retention, and so I’d be curious. You’re in Tampa. I’m in Chattanooga. Two midsize markets. It’s something we talk about all the time as a city here in Chattanooga is kind of talent attraction and talent retention, and especially in the time of remote working and kind of economic development, and all those types of things, I’d be curious, what’s your approach to talent attraction and retention been at ThumbStopper and then more broadly maybe as a mid-market community like Tampa?

Matt Brown (22:38): Yeah, a few things to unpack there as well. So, hate to keep bringing up COVID-19, but it’s the elephant in the room in every conversation still today, and it’s reality. I was lost, now that I see myself post-this whole going through what we went through in the last 18 months, and I was obsessive about not having remote employees. As a matter of fact, I have a developer that’s been on our team, I want to say, 13 years and he inherited his grandfather’s house in rural New York and it was like I was beside myself, “I don’t want to have remote employees,” and this is a few years back, and that worked. And when COVID hit and we were forced to go remote, and I think we went remote early on. I came home early from a vacation. It was going off in March. I said, “Close it down. This is the scariest thing we’ve ever been through,” and what I’ve learned from that is, my God, what a close-minded CEO I was before.

Matt Brown (23:40): And even though our average retention was 7.8 years average for employee, and I think it’s 5.8 now, and that’s because we’ve doubled the size of our staff, but looking back, the opportunities that it’s opened to get people. And we always preach, “Work-life balance.” What better way to be able to stay home and deal with things that you need to deal with, and at the same time, be productive. I didn’t think it could be done before this event. I know that it can be done now, and I’ve seen it done, I’ve also learned from that there are people that need to be in an office. There’s the other side of that too. The approach to the culture has always been big for us. I always pride ourselves on going, “We just interviewed a really talented candidate, but from a cultural fit, it’s not going to work.”

Mickey Cloud (24:36): Mm-hmm (affirmative). Gary, our CEO/Chairman, was very much in your camp of he was someone who… We never really had a remote policy for VaynerX. It was you were in the office because we were believers of the serendipity of kind of those collisions that you have in an office place, and we’re such a collaborative industry and our model is all based on kind of an integrated model of creative and media and strategy and production, and so we’ve got to all be together, and then obviously the pandemic tells you otherwise and we’ve had to learn.

Mickey Cloud (25:16): It’ll be super interesting, I think, for us as we are starting to think about, “Is there a light at the end of the tunnel, and how do we start to plan for a post-COVID world? What is the right approach in terms of time that people should be spending in the office?” I think there’s kind of everything’s on the table right now, and so I think every company is trying to reimagine what do they use their physical office space for and how do they attract and retain talent. I think it’ll be super interesting in the coming months and years.

Matt Brown (25:57): It’ll be interesting to see how the data comes in. I mean, I think collaboration in several instances is still gold and I think on the sales and marketing side, boy, there’s nothing like a whiteboard. You just cherish it. Once in a while, I get a newspaper and go, “Wow. This is so obsolete, but my God, what a great feeling,” and I think you get that great feeling on a whiteboard with a group of people as well. So, I still think there’s a lot of room for collaboration, but as a CEO, it’s been really nice to have been forced through that because I felt like I would have always been a pioneer and at some point, my kids would have been saying, “Okay, boomer. Not everybody’s got to be at work.”

Mickey Cloud (26:40): Well, one last thing. We love this building while flying analogy for entrepreneurs because it speaks to kind of the nimbleness, the flexibility, the foresight needed to operate kind of in business, but also because pilots, they’re renowned for their in-flight checklists and the training that kind of keeps them calm under pressure. So, if your back’s against the wall say because Craigslist has changed their policy and you’ve got four days to react to it and you just got to make a tough decision for the business. What’s that internal checklist or process that helps you get through it?

Matt Brown (27:13): Man. I mean, nothing substitutes just driving in and determination and hard work and grit. How did we solve the riddle? I was lucky enough to have a development team to where there were some 2:00 AM and 3:00 AM, and 18 hour days, and testing and logistics, and just enough people being around the room and kind of nervous and sweating and crying, and we greulled through it and nothing beats… When I get older and the only things that matter are kind of the memories and the stories in the rocking chair, those will be the times that I look back on that were the best times of my life, and you hear your Gary all the time talk about, “Wish it all would go away, so I can just prove all the critics…”

Matt Brown (28:10): And I love what goes through when you’re just broke again and when you got to do it all over, and maybe it’s the sociopathic tendencies CEOs have. I don’t know, but nothing beats the hard work side of it. And if you build the right culture, there’s only one word that comes into the right culture is are people loyal to their teammates and other people, and loyalty comes with just all types of adjectives around it on how those people will react.

Mickey Cloud (28:44): I want to actually dive in a little bit deeper on that last point you made, which is just around team and how and how you build that. So I’d be curious, you’ve got to build that with intentionality, and so what are some of those pillars for you guys that have helped you stand up those long retention numbers and build that type of environment?

Matt Brown (29:04): We’ve taken a foundation approach that’s kind of fashioned on one of my mentors telling me about when he worked for Arthur Andersen, and there were steps that you go through traditionally that would help you at best be successful 50% of the time. Arthur Andersen would tell you that if you do all the things you need to do, the six candidates, the interviews, the number of people in an organization that needs to touch them, the cadence of how that goes down, and you follow all those rules, the progression is that you’re only going to be right half of that time and end up with that candidate. We’ve taken a little bit blended approach to putting more emphasis on the culture, and the fit of people.

Matt Brown (29:46): So, we get the entire teams involved depending on the department these people are going to be integrated into, and we go through kind of a fun process of making sure that there are cultural fit. Again, we’ll pass on talent if we think that this person is going to be an asshole in the organization because those things bleed out deeply. So, I don’t know if that answers the question, but that’s kind of our approach.

Mickey Cloud (30:09): Yeah. No, I mean, I think that filters. So, the filter of, “Can you get along with everyone else,’ has been a critical one and kind of Vayner’s growth, and you’ve got to live by it. That’s the other part of it is if you’re mean, there’s no… You can’t be a jerk to people and work here. Then if someone shows up and gets through in, and is starting to show some those tendencies, you’ve got to be able to either talk to that person and get them change their ways or let them go because it slows everyone down.

Matt Brown (30:40): The investment of mental health too. I mean, it’s been a real topic, obviously again, rewinding back to COVID. You started to see how important it is for people to get the balance, and get the help that they need, and there was a big investment on our part where we took part in making sure people had the kind of the mental health awareness for themselves.

Mickey Cloud (31:06): As you have looked back over kind of your entrepreneurial ventures, and could you share kind of what are maybe some top three pieces of advice you have for entrepreneurs?

Matt Brown (31:18): Yeah, absolutely. One would be, do as much as you can early without taking money, and get as far as you can down the road because your company will continue to increase in value, and you’ll have to give up as little as possible. Two would be, stop buying things you don’t need. Don’t flex. Don’t flex early.

Mickey Cloud (31:49): Especially not early, yeah.

Matt Brown (31:50): Yep. Three would be, mentors. Finding people outside your circle, stop listening to your family, stop listening to your friends. Get outside your comfort zone. Find people that are making things happen in your community. Go be a part of something. I don’t care what it is, but find people that you are attracted to like a magnet and you feel that same attraction, and find people that have been through things and get mentoring help.

Mickey Cloud (32:21): On that last bit, who are some people that have played that role for you, and how did you find them?

Matt Brown (32:27): A number of people that play that role for me, I’ve picked up over the last several years through just networking and even reaching out. I mean, we found Gary Vaynerchuk. He didn’t know he was influencing us, and I’m like a million other fanboys, right? But there are remote mentors that don’t even know their mentors. More importantly, even are just people in your community that are doing business things. You’d be surprised. If young people came and sat down with me and said, “Hey, Matt. Listen, starting up a business, whatever. I want some advice.” Real entrepreneurs that have been through the rush and been through the grind, they want to help. I mean, we don’t get time to do enough philanthropy and if we can help other entrepreneurs, reach out to people that you know are successful.

Mickey Cloud (33:15): Those three pieces of advice resonate with me and I’m sure with a bunch of our audience, so I appreciate that. Matt, thanks so much for taking some time today and sharing your entrepreneurial journey and lessons, and all that you’re building with ThumbStopper and That’s Us, and in the entire kind of venture there. So, thanks for your time, and we’ll chat soon.

Matt Brown (33:37): Thank you, Mickey. Appreciate it.

Katie Hankinson (33:41): Well, now that we finished that thoroughly interesting interview, we’re getting ready to land, but before we do, Mickey and I spent some time unpacking some of the key takeaways that really stuck out to us.

Mickey Cloud (33:52): We liken this to the post-game show, where we break down the really extraordinary nuggets that we can all benefit from, including us here at The Sasha Group. So, get ready for The Sasha Sidebar.

Katie Hankinson (34:09): Hey, Mickey.

Mickey Cloud (34:11): Hey, Katie.

Katie Hankinson (34:12): That was a great interview with Matt Brown. How was it to be chatting to one of our Mentors clients?

Mickey Cloud (34:17): Yeah, it’s super interesting because Maribel, who heads up our consulting and mentors program, she I think is Matt’s kind of day-to-day point of contact and kind of led the work that we did the growth plan for ThumbStopper, and so I had never met him before. I’d always heard about business. I had heard Maribel had spoke glowingly of him and kind of his reputation and how beloved he is by his team and his company, but it was pretty cool to kind of dig into the business in an informal way, where it wasn’t a kind of client to agency relationship, but instead just kind of a business owner to business leader kind of thing.

Katie Hankinson (34:55): Yeah, catching up on his story. And he definitely is a serial entrepreneur, having gone through all of those stages.

Mickey Cloud (35:01): And that’s just what’s cool about the mentors program is we get to connect with founders, with builders who are looking for new ideas and new ways to really get that kind of exponential growth.

Katie Hankinson (35:15): Yeah. I thought it was interesting when you were talking about the platforms and keeping up with the platforms, and Matt told that story of the most stressful true difficult time that he’d had when Craigslist changed their whole model. And overnight, he lost a gigantic chunk of his revenue.

Mickey Cloud (35:37): 40% he said.

Katie Hankinson (35:38): Insane, and yet, obviously came through that stronger and having diversified a little bit more, and also really used his skills to pivot the platform to actually still be able to provide his clients with something that would work on the new form of Craigslist. I feel that it’s really interesting with a lot of what Gary has said, what we often say to our clients about just not being too beholden or too romantic about any one platform, whether that’s a platform that you’re using to run your business on or run your advertising on. Just that idea of not having all your eggs in one basket when the landscape changes constantly.

Mickey Cloud (36:16): And it’s interesting because he had kind of put the perspective on of, “The focus is good. I’m going to be the best on Craigslist,” but then when his business model got rocked because they made an update to one of their policies, it forced him to kind of have a wider focus, a broader focus, and that’s the reality when you’re building on top of these platforms, or you’re relying on platforms for so much of your revenue, it’s a bit of a dangerous game. Gary always talks about it, whether it’s beachfront property, you kind of think about it that way.

Mickey Cloud (36:51): So, when Clubhouse is skyrocketing with attention or TikTok. You go early not because on the chance that you could do something there that can really kind of take the business off because of the organic distribution you’re getting on those platforms, but also for the learnings of the next time something comes around that’s related to audio or to vertical video, or to these other things. If you test it out, Clubhouse and TikTok and what it can do for your business, then you’re better at it the next time something that plays with those core skills comes around.

Katie Hankinson (37:23): Talk a bit more about that because I think that’s something we often say to our clients like, “You don’t have to be on every platform,” but the thing to bear in mind is it’s worth experimenting and trying as much as possible.

Mickey Cloud (37:35): Yeah, it’s it comes down to time and effort, right? And that’s what’s great about our mentors clients is we can be very honest and open with them about this, that if you’re asking for exponential growth, sometimes it’s going to take more work and more time to put in effort to learn how to put out great content on LinkedIn and take advantage of their organic distribution, how to do duets on TikTok, and how to post Clubhouse rooms, and things like that. And yeah, it might not have an immediate payout on the business, but there’s experimentation, there’s learning, there’s also brand-building opportunities.

Katie Hankinson (38:13): Yeah, I thought that his top pieces of advice for entrepreneurs were such a… There’s such a strong thematic developing around really don’t overextend yourself or don’t flex too early, which I thought is so true. You never know when that creative moment may happen, and then the other big one, which is time and time again such a core part of really driving success with business is surrounding yourself with people who you can learn from and who are making things happen, whether they’re remote or immediate mentors. It really is such a theme among all the people that we’re speaking to.

Mickey Cloud (38:54): Yeah. So, I think maybe the question for our listener out there, I think maybe we would love to know if you’ve had a moment in your business where you have been too reliant on a platform and something shifted and changed, and how did you kind of navigate through that?

Katie Hankinson (39:09): All right. Mickey, we chatted a bit today about The Sasha Mentors program, which Matt at ThumbStopper is a part of. So, I thought it might be an idea to give some context on what that’s about.

Mickey Cloud (39:19): Yeah, of course. So, the mentors program is… What I kind of term is it’s our holistic business consulting offering, so we work with clients that are mature businesses, established businesses, but they’ve maybe hit a plateau or they’re just looking to really exponentially grow their business, and so the main deliverable, what we provide after going through kind of analyzing their entire operation, not just marketing, but looking at supply chain, looking at their partners, how they’re operating their businesses, is a growth plan and then we work with them over a three year time period. We’re helping them to implement that growth plan.

Mickey Cloud (39:56): And on the implementation side, we actually take a piece of the upside. There’s a performance share aspect to it, and so it’s a total situation where as our clients win, we win. And so, it’s total kind of alignment of those incentives. We take on a few mentors clients every year, and it’s been really awesome to see that… There have been some businesses that haven’t just grown 5%, 10%. It’s like they’ve doubled the size of their business in two years, three years, gone $10 million business to a $20 million business after kind of implementing our growth plans.

Katie Hankinson (40:25): Yeah, it’s a great way to push past a plateau or maybe with some businesses who are stepping into a new business unit or part of the market. Awesome to see. And we’ll get Maribel, who leads our program, on the show for a future episode so we can chat more about Mentors. And then on the other side, still in the vein of education and community, for business owners or leaders who are looking for other ways to learn, maybe not ready for something like Mentors yet, we also have Stork, which is our membership community of business leaders. Stork takes the form of a pretty active Facebook community, a very diverse set of different companies and a regular program of marketing education around how to think about branding, business, digital marketing tactics, and more. And it’s a great way to just get access to the thinkers at The Sasha Group, and to chat about some of the philosophies that we talk about every day as well as be part of a community.

Mickey Cloud (41:22): It’s a super active community and it’s awesome to see all the different business owners and leaders that’s in there. So, if you want to find out more about Stork or Mentors, you can check out the website, you can DM us, you can email We’re very active and we’ll have a chat with anyone about either Mentors or Stork.

Mickey Cloud (41:43): Thanks for joining us, gang, and for building while flying with The Sasha Group today. I hope you learned as much as we did. We’ll meet you right back here next time for another flight.

Mickey Cloud (41:55): If you’d like to hear more about how business owners and brands are navigating these times, tune in to the next episode And if you’re so kind, please rate and review us. Plus, we love feedback, so let us know what you think, what you’d like us to dig into next on Building While Flying, across brands, businesses, marketing, and more.

Katie Hankinson (42:09): Original music by Fulton Street Music Group.

Welcome to Building While Flying!

This weekly podcast is brought to you by the Sasha Group. We’re the consultancy meets agency arm of the VaynerX family of companies. We help ambitious companies build strong brands that flex with the times through strategy, branding media and marketing.

In ever-changing times, businesses and brands have to shift and adapt. And across all sectors, there is an air of experimentation. Business owners are trying new things out in the wild;  building the plane while flying.

Our pilots, Katie Hankinson and Mickey Cloud, will be talking to a diverse range of business leaders and founders. They’ll explore how these guests tackle various challenges while staying resilient and committed to growth. Through these real-life examples of strategies put into practice, we hope to inspire you to experiment and develop your own strategies as we all navigate these uncertain times together. 

Matt Brown is an expert in pivots. 

His career has been full of them—from leaving college to work as a technical recruiter, to keeping up with the platforms that literally drive his business, to adapting to the remote working environment, and much more. After realizing the disconnect between manufacturers and the retailers that sell their products, Matt launched ThumbStopper, a SaaS social media marketing company, to help bridge the gap between online and IRL inventory and retailers’ and brands’ social media presences. 

In this episode of Building While Flying, Mickey and Matt unpack the macro and micro pivots at each step of his career. Matt explains how ThumbStopper came to be, and talks about how adapting to new data and updates constantly changes the dynamics of conversations he has with his clients and partners. He revisits a career nightmare involving a Craigslist terms and conditions update that made nearly half of his revenue disappear overnight, and how his team persevered to quickly build a solution. Lastly, Matt and Mickey discuss the importance of company culture and team building, and how those impact talent retention over time. 

Other in-flight topics:

  • Matt’s career path
  • Adapting your business based on new data, statistics, and platform updates
  • Grit and determination during challenging times
  • Impacts of remote work
  • Importance of culture and team-building
  • Advice for entrepreneurs

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