LMSM 42 | Shaquille O'Neal


In this episode, Ian shares his story of landing a meeting with legendary basketball star, Shaquille O’Neal. Both literally and figuratively, this meeting with Shaq was among the biggest of Ian’s career. Ian made Frank wait until recording to hear the details of the meeting, which makes this episode even more fun. 

In this episode: 

  • What is Ian working on that could lead to this encounter? 
  • Why choose Shaq as a potential partner? 
  • How to prepare for a meeting that could change your life 
  • The importance of taking big swings 
  • Taking calculated marketing shots 

Watch the episode here

Listen to the podcast here

Ian’s Meeting With Shaquille O’Neal – Part 1

This is the first part of my story about the time I met with Shaquille O’Neal. In part one, Frank, who knew about this meeting, asked me all the juicy questions. We talked about everything leading up to this meeting. Why was I meeting with Shaquille O’Neal, for what company, for what business purpose would this serve? This is a blast to do this because I went on this trip to meet with Shaq. Frank was desperate to know how it went and I was purposely quiet about it. Everything that you will read in part one and part two of this episode is Frank knowing about the meeting with Shaq for the first time. We did no prep for this and he interviewed me so we could get all of his reactions. It was a fun moment for me to meet with Shaq. We had a blast doing it. This entire episode sets up the meeting and all of our preparation going into it. If you are a regular subscriber and you like our show, please do us a favor and give us a five-star review on Apple. If you are new, subscribe anytime. We’d love to have you. 


Ian, you son of a bitch. 

It’s an odd day for us. 

It’s an odd day and it’s an odd situation. We’ve got all kinds of things that are goofy. I’m in a hotel room in Florida trying to take a vacation but Let Me Speak to A Manager never sleeps. Some podcasts have guests. The Tonight Show and all these other places have these incredible guests. Famous people come on their show and that’s the whole premise of their show. Not here with Let Me Speak to A Manager. We simply talk about star encounters. That’s what we’re going to talk about. We’re going to talk about a star encounter. I thought it was worth breaking up my vacation to do this while it was fresh. You and I have not texted, talked or done anything. We’re going to do it in its raw form right here. 

Let’s do this. For the record, I haven’t told Frank anything about this. He’s dying. I had a meeting with Shaquille O’Neal and it was two hours long. It also involved a company that Frank is invested in and he has had to wait 48 hours to hear anything about this. He is hearing all this for the first time and he is bursting with enthusiasm about his investment and how it is being protected. 

I had lunch with my dad and he’s like, “How’s that alarm thing going?”I was like, “It’s going good, dad.”  

The Sheriff is in for a piece. What’s he in for? 

He’s in for $50,000.  

Frank’s dad, I’ve lovingly nicknamed him The Sheriff and somehow, it is stuck within his family. This late in life, he picked up a great nickname. He’s got this amazing mustache. He’s a very stoic man. Not nearly as gracious and talkative as Frank is but an amazing soul. He’s offering for lunch and one of the first things he said to Frank was, “Are we losing our ass in this $50,000?” Frank, it’s got to be amazing talking about a tech startup with your dad. 

It’s incredible. Talk about your all-time great ideas and bring your dad in on a tech startup. Here’s how I want to play this. You met with Shaquille O’Neal. Talk a little bit about the meeting, how it worked, what is it like to get a meeting with someone as famous as him? 

Why don’t I start before that, Frankie? I don’t know that we’ve talked a lot about Keep, this tech startup.  

I was going to get into Keep in a minute.

When something gets in your mind and comes into your universe, you see it everywhere. Click To Tweet

Maybe we’ll start a little bit. I am invested in a technology startup. I’m also the Chief Revenue Officer so I have equity that I purchased, and I have equity that I’ve been given for my role in my activities. The CEO is a good friend of mine that I’ve known for many years. We worked together at GE. He worked in the same office as me and he was on the same program as me. He probably came in three years after I did in the same sales program. For a short period of time, he reported to me. I was his sales manager. Years ago, we were driving all over the Midwest, making cold calls with customers and closing deals. After I left GE, he left shortly after to get his MBA at Harvard.  

Since then, he’s been a serial entrepreneur. He was in American Inventor, which was the predecessor to Shark Tank for an engineered bike rack that goes in your ceiling called The Claw and they’ve sold a million units of that. He sold that company. He also started a company called Code Guard, which backs up your websites. The first thing I did after I left NVR was rolling my sleeves up and dive in and that company because I’d invested in it seven years before to protect my investment, and it was a blast. It was a period of time where Code Guard was in a make-or-break moment. Sales and marketing were a big need that David needed help with. That’s a little bit more of my background in programming and code.  

I traveled all over the place with David. We went to Germany and went around to several large hosts and spent time with him on the phone every single day until we sold that company. The return of that company was close to 15X or 16X on investment. We sold it for about $30 million. Six months after that, David called me and said, “I’ve got an idea. I want to run it by you and see what you think.” It was for a connected car alarm. Think of Ring doorbells for a car. This was a device that looks like an Alexa that would fit into a cup holder.  

At the time, this was all just theory. He had drawn it out on paper. The reason why David wanted to do it was his car had been broken on multiple occasions in multiple places in Atlanta. Like most major cities, Atlanta has a major problem with car theft, car break-ins and everything else. From my recollection of that initial call, I poo-pooed it. At the time, I didn’t think it was as big of a problem as he did because I hadn’t experienced it. I live in a nice suburban neighborhood and that hadn’t happened to me. The other part of me was there’s no way this hasn’t been done before. My mind immediately went to Viper and some of the cheaper dashboard cams. My assumption was there’s no way no one is doing this.  

As I anticipated, you were going to interview yourself. Let’s think it through. He calls you up, you think about this, you hear about Keep, it’s an idea. What is interesting is a couple of things. You decide to unretire to do this. When someone comes up with a concept, what I do is concrete. The things that I do are real estate. You can drive it, you can see it, you can see what’s around it. What I’m fascinated by is the conceptual process of going out and saying, “We are going to change the world. This piece of technology does not exist and we’re going to create it.” What I would like you to walk us through is you’re going down that road with Viper. In the PowerPoint, you put together an interesting slide of how that went. I’m curious how both you and David arrived that there’s a need, this is how we’re going to do it, and the backstory.  

It was months for me to be interested. Most companies start with ideas and you have to beat those ideas up and try to find as many naysayers as you can or at least information to the contrary of what your thesis is. David’s thesis is, “There’s been no disruption in this industry forever. The technology is weak. There’s so much more we could do, the solutions out there are not effective, and this is a big problem.” When he brings this to me and says, “I want to do this and I want you to be involved with me. I have to go on my own.” My job is I listen to what he says and do research. The best way to do that is to act as a customer as if I had that problem.  

What’s fascinating about this whole thing is you go to Amazon. You look at the top ten products, you type in car security, car theft deterrence, and you’ve taken notes on what those products are. What are they? Do they work? You read reviews. I’ve read thousands of reviews on every product for a car alarm you could think of so that you can see what people think of those products. You Google Search the hell out of it. I started following multiple sheriff departments that I saw were always putting out in towns where car theft was becoming a bigger problem. What are those sheriff departments and police departments recommending people do to protect themselves? 

While you were learning this, I was a little bit late to rap. It was like when I discovered Biggie and I was texting you lyrics of his catalog and you’re like, “Yeah.” I’ve known about this stuff for decades but I was so excited to give you lyrics and things that I thought were fun. What you were doing was the same thing. You’re like, “Did you know this statistic?” I remember getting tax correspondence from you as you were learning about this.  

Everything in the discovery process with a startup is fascinating. David has the thing he says, “Nothing hits the cutting room floor. We keep everything. We store it and we keep all that information. You never know when you’re going to need to use a bit of information.” He’s insatiably hungry for new information and he’s specifically in tune with information that is contrary to what he believes. One of David’s superpowers as a CEO that’s made him successful and having done this twice successfully with great exits, more than most people I’ve ever met, he’s not into confirmation bias. He’s the opposite. He’s looking for information that attacks some of his strongly believed thoughts already.  

He doesn’t argue often when I call and say, “You’re off on this. I’ve got some new information.” He won’t take it at its word. He’ll go do his homework to see if what I’ve uncovered makes sense but he’s good at fighting his own confirmation bias. You have to be in a tech startup because all that matters is can you solve something? I did a lot of this research but as I was doing this research, I came out of my house one day in my nice, safe bubble of a community, and everything in my truck was all over the place. From the glove compartment to the main consul in the middle, everything is strewn all over the place. A pair of my Maui Jim sunglasses were stolen. I’m like, “Holy shit. My car got broken into.” I talked to a few neighbors and their cars got broken into. We did what everyone does, you go look at everyone’s Ring doorbells and there it is, a group of teenagers slowly driving through our neighborhood running and pulling up on door handles.  

I called Dave and was almost excited about it. I’m like, “You’re not going to believe this.” I don’t know if this happened to you, Frank. I wasn’t thinking about car alarms but now, all of a sudden, that’s all I was thinking about because I was trying to decide whether I was going to invest a lot of money and my time to be an officer in this company. The more I researched, the more I was in-tuned with hearing words about this. I would be at my pool and a neighbor would be like, “So-and-so had their car stolen.” I was like, “No shit. That’s three blocks from where I live.” All of a sudden, I start talking to you, you leave your car running and people steal a roast from you. 

I’ve got to tell that story. As you started, there’s a phenomenon that we can look up. I remember the first time I ever heard it. It’s back in the ‘90s. If you bought a white Ford Explorer, all you’d see on the road are white Ford Explorers. Ian would call me up and he’s like, “So-and-so got his car broken into.” We’re thinking about Calvin Johnson, the Megatron, the guy who played for the Lions for years had his car broken into. Do you want me to tell that story now or later? 

Tell it.  

Here’s what happened and I’ll ask you what you thought of it. I call Ian up and I’m in hysterics laughing and I’m in a fortunate position. I had gone and bought a Christmas dinner and all the components to put it together. It was an expensive roast, a bunch of pork chops and fish. It was $650 worth of stuff. What I did, like a complete and total dumb ass, is I went up in my office and I left my car running. Thankfully, I have my keys. I left my phone in my car, left my car running, and I went upstairs to grab something. Invariably what happens when I do this is I get into something. I’m sitting behind my computer and an hour and a half go by.  

As I’m walking into the building, I bumped into the owner of the building and he and I started talking. He comes back 5 to 10 minutes after I talked to him to say something else to me. I’d already been interrupted once and someone’s like, “Someone is at the front door.” I figured it was the same guy again. I go down and there’s a woman standing there. She’s like, “Do you own the black SUV? The one that’s running?” I said, dripping with sarcasm, “Yeah.” She’s like, “I’m pretty sure someone broke into your car. I saw a kid on a bicycle. When I pulled up, his bicycle was parked behind your car and I’m pretty sure he was in your car. I’m like, “Okay.”  

LMSM 42 | Shaquille O'Neal

Shaquille O’Neal: If you’re not a homeowner, the car is your biggest investment. There are people who drive cars for years, and all their valuables are in there.


I walked downstairs and looked and it’s the same experience, Ian. It’s like these pieces that go directly to your glovebox and they’re like three-year-olds. They throw everything around the car. There’s crap everywhere. There’s a knife, your flashlight, and all this stuff in your glove compartment are all over the place. I shut my car off. I go back upstairs. I’m like, “He broke in but he didn’t get anything. He didn’t even find my sunglasses.” It dawned on me. I had gone to Yellow Umbrella and spent $650 on food. The kid took my soft cooler on his bicycle and pedaled off with it.  

I called Ian and I was like, “You’re never going to believe this.” He’s like, “I can’t wait to tell David.” The best part of this story is I go back to the store where I was to buy my beef or my fish. They all know me by name. They’re like, “Why are you in here? Didn’t you were just here?” I’m like, “Someone stole my bag of food.” They were like, “That sucks.” One kid pipes in around the counter and goes, “Can you imagine, You roam in your neighborhood with that big roast over your shoulder on your bike? He’s going to be the man.”  

When Frank told me this story, it took him an hour because Frank gets into hysterics sometimes on his own stories. He was giggling and I had to keep making him repeat everything and he would go back. 

I told my wife this and my wife was like, “You do realize how fortunate you are that at $650, you don’t cancel Christmas. You just go rebuy it.” I said, “I’m incredibly fortunate.” That’s what we’ve talked about, Ian. For us, car theft is often an annoyance. If someone steals a pair of our sunglasses or somebody does something, we go back out and rebuy it. I’m going to seed this and I’ll have you answer it. When you start doing your research, you start to realize the average age of most cars. If you’re not a homeowner, the car is your biggest investment. Most people are driving cars for years and valuables are in there. We can joke about me being a dumb ass and getting ripped off for $650 worth of meat. Regular American people, normal people, their cars are a big deal. This is sacred turf and it’s constantly being broken into. Why don’t you talk a little bit about that, Ian?  

The average person losing $650 of cash, $650 watch or $650 worth of groceries could break them. Most people don’t have a lot of money in the bank so theft is a big problem for them. Getting back to the finish, because that was a perfect segue, there are the analogs. You start seeing them everywhere. When something gets in your mind, it comes into your universe. You see it everywhere. I was seeing it everywhere even in my circles. I run in more fortunate circles than the average bear these days. I didn’t grow up that way. Now, the people I interact with have enough money where a break-in won’t kill them. I was seeing break-ins everywhere, even in my town of Vienna, which is an expensive zip code, so there’s that.  

Also, in that search for what are the solutions, it’s a question that you’ve got to ask, I was finding old stuff. You’d find all these top ten lists. You’d see the top ten sellers in Amazon under the car theft and car security and it’s still The Club, which is a big piece of metal that goes on the steering wheel that’s been around since ’85. You still saw Viper in the top five list. Viper is notoriously bad at false positives of alarms going off when fireworks go off or a big truck hits a bump because it’s vibration-based. It’s been banned in a lot of big cities because they’d go off all night and keep the neighbors up.  

One of my favorites, 6th on a top 10 list, was this little $5 device that blinked red and does nothing else. It was a placebo. It was a deterrent. The comparison would be sticking a security sign in your front yard even though you don’t pay for the security to make the thief think that you had security. That was one of the devices that I found in one of these top ten lists. The more I researched, the more I realized that there wasn’t anything good from a technology perspective. That got me more excited. The more I researched, the more I saw that a lot of this is growing. This is an enormous problem.  

There are a lot more vehicles on the road than homes and Ring sold for a $1 billion valuation. When you look at analogs of other companies, this is months of research and it wasn’t one call where I told David that I’m in it. It took him a lot of conversations where I was like, “This is worth spending a big chunk of my time over the next five years. This could be big.” That’s a little bit of how we did the research. The device and product were exciting. We had ten pending patents on it. We quickly realized that a lot of people hadn’t done some things we were doing in the space. That was probably a few years ago.  

We raised $4 million for this business and that’s when Frank came in. The people that are in on that $4 million investment are friends and family of David and me. Like what we’ve talked about with real estate, it’s one thing for me to say I’m in with my money. When I start calling people that I care about and how they feel about me, I took that level of research up an insane amount. If you want to learn about something, go teach it and sell it. I got a lot more investors by raising that money. 

Before we turn the corner on this, I want to exhaust something that we’re talking about here for a second. When I quit NVR, I didn’t know what I wanted to do. You and I have talked about this multiple times. I ended up picking the space that I’m in for a very significant set of reasons. I started in the heat of the recession so I knew that I could manage the downside. I knew that my asset was going to be turned around quickly in 90 days. I also work fast for 90 days so I could always get my money back out. I also realized that my competitors, Wall Street, hadn’t shown up yet and they’re in my business in a big way. Tech is my business in a big way but when I decided to get into this business, those things weren’t there.  

What I started to understand was I almost got excited. I realized, “Holy crap, I have an unfair advantage in this market because of my training, the things that I’ve done, and everything along those lines.” Before we get into the actual company and the deal, as you’re in this vetting process, what is it like when you realize, “This guy is right. We have an advantage.” There’s a need and an advantage. We’re competing against people that aren’t organized. When your competitor is Lieutenant Jack Klaric from the Cleveland Police Department, we’ve got to pull up that 1980s video and use it. He’s holding The Club and he’s talking about that. That has been a joke in my friend circle for decades and that’s your number one competitor. Talk about that excitement because I feel like that’s where good ideas and good companies start. 

I spent probably more time on anything than the competition. You look at all these police departments, they come out and they say, “Protect yourself. We’ve seen a rash of car thefts. Here’s what you should do to protect yourself. Lock your doors, park in a well-lit area, park in a garage, and don’t leave valuables on a seat where people can see it.” When you look at that, it’s like them throwing their hands up. There’s not much you can do. Your car is not your own. If you think about those things, those are the same things that the police were saying in 1915 about a Model T. That’s the same process. There’s no technology and there’s no protection. You read all that and you’re like, “My god.”  

There are a lot more vehicles on the road than homes just sold for a billion-dollar valuation. Click To Tweet

A lot of the other stuff you’d read too, people shame people so it’s like, “I got broken into.” They’d be like, “Did you leave your keys? Did you leave it unlocked? Did you leave it in your driveway? Was it not parked?” It’s gotten so normalized that people almost shamed the person who got their stuff robbed out of their cars if it’s their fault that some a-hole went and took their stuff. It’s wild. The more I studied, the more excited I got about it.  

It felt like a blue ocean thing where while there are a lot of runways. If our product does what you’re saying that you think you could build, David, we could kick a lot of ass. My role in companies when I’m with David is on the negotiation side. It’s on the sales and marketing side. For me, in particular, the challenges that I would be faced with in this business, I was very excited about. I felt confident that if David could build a device that he told me he could build, we could run away with some sales on a product like this. 

For those of you that read regularly, you know that Ian retired and the only thing he’s committed to besides this incredible podcast is coaching baseball. What I wanted to ask you are two things. What is your title with Keep and why did you decide to unretire to do this? 

My title is Chief Revenue Officer. I fought David. I didn’t want any title. I wanted him to call me an equity partner or whatever you want to call me but that’s my title. The reason why I decided to go all-in on this is that in your career, you only come across 4 or 5 people that no matter when in your career, you would want to do more. You are someone much like that with me, Frank. David is another one in my small circle of people that I trust implicitly. He’s a lot like me in some ways and probably even more than me and you. There are a lot of things where we’re different. We complement each other well.  

We’ve been selling things together since we were kids right out of college so we know each other. We can finish each other’s sentences a lot. There are some people that I’ve come across in my career that one plus one equals three. When we have a discussion, normally both of us get strengthened and we get off the phone with a better idea than both of us had when we got on. It’s been like that for over twenty years. He’s a guy that I have fun working with. He’s a fun guy to work with. He’s the smartest person I’ve ever worked with. He’s got an unbelievable brain.  

He’s a president of a student body at Georgia Tech, mechanical engineer, Harvard business degree. He’s a lot smarter than I am. I strengthen him a little bit. He does have an engineering mindset. From a sales perspective, I add a lot of value to him. The two of us make a good partnership. When David comes and talks to me like when you bring a real estate deal to me, I just take it more seriously and I get more excited about it because I’ll have fun. and I trust him. He’s someone I’ve worked with for so long that I don’t need to kick the tires too much. When he has an idea, I give it more attention than I would someone else. 

I want to talk about a couple of things here. First of all, I want to talk about the fact that we need to do a party now that everyone is vaccinated and the world’s opening up again. I’m down in Florida. It’s a fantasy camp. It’s like COVID never existed here. It’s incredible. I want to get Paxson and David in a room together and get at least eleven bottles of wine and sit the two of them next to each other. You and I sitting at the back with popcorn and watch the two of them go at it. That would be fun. In all seriousness, in my life, I can think of a handful of moments or conversations that I’ve had where I can remember where I was, where I was sitting in the conversation. This is an enormous compliment to Ian.  

Ian and I were talking. I was sitting in the parking lot of the Gold’s Gym in Richmond. I was about to go in, the phone rang, it was Ian, and I picked it up. Ian and I ended up talking for well over an hour. This was the conversation that you had with your boss about, “I’m turning 40. I’ve got a decade left and I need to position myself. If I’m going to spend my 40s somewhere, I need to spend my 40s doing this in a way that’s different.” What ultimately happened is it wasn’t when you walked in but you got a huge raise. It was a huge strategic thing. Ultimately, it pole-vaulted you to leaving when you did because of some of the things that you negotiated in that conversation.  

Do you remember that conversation you had with me and talking about that? I want to pivot into something you talked about with Keep after this. My takeaway from that conversation with you was this, Ian is playing a high-stakes, meaningful version of chess with his career. He’s being incredibly strategic in how he sets things up. He’s setting things up where he doesn’t necessarily know exactly what the answer might be but he’s given himself 5 or 6 different outs and I thought that was an incredible conversation. 

I remember talking about that and telling you what I did after the fact and that was shortly before I turned 40. At the time, I wasn’t sure if I was resigning. I was almost giving him the option of, “Let’s find my replacements. In six months, I’ll leave.” This was about three years before I left NVR where I said, “You paid me well. I have a fancy title but I’m still doing a lot of the same shit I was doing ten years ago. I don’t know if this is how I want to spend my 40s.” I’m like, “I like you and we get along and it’s worth me telling you that these thoughts are going through my head so that you’re not surprised one day if I tell you I was serious about spending my 40s differently.”  

I didn’t want it but it was a big promotion, a big title. I was handed the keys to all the offices in the company and millions of dollars worth of stock options. I remember telling you that I’m not sure that’s what I was trying to do but that’s what came out of it. That was their approach of saying, “You are going to spend your 40s doing this.” That didn’t work either. It took three more years. I did want to spend my 40s doing something different than what I was doing. 

When I talk to people who know you from that portion of your life, and there’s not a lot of them that know you well enough and that I have a mutual relationship with. Those who speak honestly to me about it. The few people that I do know about it are like, “Why the hell did Ian leave and leaving that much money on the table? You walked with a huge exit but you left a ton on the table.” What I’m curious about is why jump from the frying pan back into the fire? Where is this similar? Where is this different? Why?  

I left a lot of money, eight figures worth of stock options. At the time, I was working fifteen-hour days. I worked on Saturdays. I traveled all the time. I was doing it in a business that I didn’t care about at all so it was a soulless grind to make that kind of money. With a tech startup, everything is exciting and new. I’m not working fifteen-hour days right now. There’s going to be a point where I do. I look forward to every meeting that we have now with Keep. I look forward to getting on our daily scrum calls and listening to what our engineers are working on. There’s something different, Frankie, and you know this, of inventing something and being a steward of someone else’s ideas, which is what a big company is.  

For me, it was going to be my own money into this, my equity. I knew the owner well and trusted him and I could make a big impact on something that was starting. Even if they gave me the CEO role at NVR one day, I’m not going to make a big impact. You’re still doing the same things that the founder created 50 years ago. To me, if I’m going to get busy again, I want to do it in something that’s mine, that I have equity, my ideas are valued, and I can make a big impact on the product, the direction, the strategy, the marketing, the financing, everything.  

I was never going to do that in a Fortune 500 company. No one is. The CEO doesn’t even do that in a Fortune 500 company because the board is telling them what to do and mutual funds that own your stock, all of that. For me, that’s a big difference and I’m still able to do this and coach all of my teams. I don’t have David saying, “Meet me in Atlanta,” every day. He knows I can add value from where I’m at, wherever I’m at, and I can do it on my own schedule. The two are just incredibly different.  

I know that. I asked that intentionally. My takeaway there are three. What I hear is if you work for a company and you’re unhappy but you like the company, figure out how to create a role that allows you to thrive within that company. At certain places, you can’t do that. At my company, I’ve had these conversations with people and we’ve moved across platforms and different segments. We have the ability to be creative. You have that at Keep because Keep employees can write their own story there because it’s not as structured as a Fortune 500.  

LMSM 42 | Shaquille O'Neal

Shaquille O’Neal: Until you shut it off, you have no idea how much a big company takes off your mind space and how much you are capable of creating.


I have a business coach, I told you about him before. He and I were having a conversation. He’s like, “I’m going to give my kid a bunch of money so they don’t have to go to college and start a business.” I’m like, “Cool.” He’s like, “Wouldn’t you take that deal?” I’m like, “No. I take both.” He goes, “What do you mean?” I’m like, “I feel like college and I feel like working at NVR for twelve years has set me up in a way that’s different from other people who I compete with within my space.” The reason for that is they gave me a nomenclature background structure. They taught me a bunch of different skills. I got talented enough to take those skills and do something else. It’s like what you did, Ian. You built a skillset at GE and NVR. You took those things and did something different with them.  

My third takeaway is you only get one life. You’ve helped me with realizing when you’re in the moment, enjoy the moment. You realize I have more money than I need. I don’t love this anymore. The moment right now is coaching and being with my family and my kids. You and I talked about it a lot. What is fascinating is that Keep turns into what you and I both think Keep is going to turn into. You may end up with more money than you stated in the NVR and you did it in a way that allows you to be engaged, having fun working with people you want, and be excited about what you were doing. That is a holy crap kind of a thing that most people miss.  

When all of this happened, it’s one of these deals where you said something before I left in NVR where you said, “Until you shut it off, you have no idea how much a big company takes of your mind space and how much your mind is capable of creating.” I always remembered you saying that to me and it’s true. Once, all of a sudden, you’re given 60 hours back a week to use your brain to read, study, talk to people and think, it’s amazing how many avenues you can go in life.  

The key is saying no to the first few that hits you to stay busy because you’re nervous. I had to say no to a lot of people that I’ve enjoyed working with in my career because I thought of myself doing the job and thinking, “Money is the only thing that would be interesting about that.” Taking some president job for another big company but doing the day-to-day job sounds terrible. I’m not interested. You’re right about you can go about any avenue. If Keep does what it’s going to do, I’ll make significantly more than I would have made staying at NVR. 

That’s a position of being fortunate. It’s worth pausing and saying that. Getting your Christmas dinner ripped out of your car and buying it a second time is a place of being fortunate. It’s positioning. It’s a bunch of other things but there’s a fortune in that. Ian has earned through hard work, discipline, smarts, negotiation, everything else, the ability to create a fortune and opportunity for himself, which is cool. Let me ask you this because I want to pivot to the second half of this interview. I want to talk about what happened. Is there’s anything on Keep and David, your relationship, why did you do this? Anything that doesn’t specifically deal with going to Atlanta that we missed that would help our readers understand exactly what we’re talking about here? 

I don’t think so. To get everyone caught up, we have a prototype that works sometimes and we are working our asses off to get a production device that can work 100 times whether you make a million units or not repeatable in any temperature, in any space, any light and anything. There are 50 electronic components inside of our bill of material that all interface with each other and that are all controlled by two PCBs which are circuit boards. That’s the brains of the device and there is interference.  

All of these have little electric interference they’re kicking off that are screwing up the others. There’s a cellular module. There are two sensors. It is a highly engineered ten patent product that works sometimes in our prototype and it’s probably going to be another 6 to 9 months before we have a consistent production device that can be manufactured out of a factory consistently to where we could take an order of 100,000 units from Best Buy, Target or Walmart.  

That’s the phase of the challenge that we’re in right now. We’re not selling this unit. We have one that works. We have a lot of good CAD renderings of what the device is going to look like and all of the other key components around the family of products. That’s where we’re at. We’re burning about $100,000 a month. We have $4 million that we raised so there’s probably $3.2 million or $3.3 million in the bank still and we are racing to get that production device. Sometime around early spring of 2022, we will have raised another $10 million to $30 million so that we can go ramp up our inventory based on some sales that we’ve got. For anyone reading, that’s where we’re at in our life cycle. 

I’m going to come back at the end of this thing and talk about the need to spin plates and do multiple things at a time. What I want to get into right now is you got back to Atlanta. We’re recording on a Friday. You flew to Atlanta Wednesday morning and you flew back Thursday night. Let’s go to the overview. What did you do? Who did you go see? How did it come about? What did you do? Talk to me about Atlanta. 

The title of this episode is Ian’s Meeting with Shaq so there’s no mystery in this. In late January of 2021, David texted me and said, “Do you got a minute?” This was late at night. I’m like, “Sure.” This is not unusual that Ian and I would talk at 9:00 or 10:00 at night. Innovation strikes at weird hours. I get on the phone and he’s like, “I’m looking at this Big Brothers and Big Sisters of Atlanta. There’s an auction item of one-hour mentoring with Shaquille O’Neal.”  

Like everything, these random thoughts that come across your desk, my initial thought was, “What the hell would we do that for?” It didn’t immediately strike me as something that would make sense. I’m like, “How much is it?” He’s like, “Right now, the current bid is $1,500.” I’m like, “What are you thinking?” He’s like, “Shaq was an initial investor in Ring. He did all the commercials and Ring is the analog for our company. That’s the business analog.” I’m like, “You’re right.” He was involved pretty early before they sold to Amazon.  

The more we started talking about it, I’m like, “Isn’t Shaq a cop?” We start googling and I’m like, “Damn, he was a cop.” I remember seeing a bunch of the hats. He’s been an assistant deputy. He’d got his training in LA as a police officer. The more we start researching, I’m like, “He might be the most famous cop on the planet.” We’re starting a security business that’s going to help police officers catch people that are in the crime business around cars.  

We start thinking more about his marketing prowess. Everyone knows Shaq. He’s probably one of the most recognizable people on the planet. The more I’m looking up, I’m like, “Damn, it’s not just Icy Hot. This dude invested in Google. He invested in Ring. He owns 100 Papa John’s.” You go through the list of things he’s promoted and been involved in. He’s been a spokesman for Pepsi for over 35 years. He’s a larger-than-life guy. I’m like, “$1,500, bid on it. Let’s do it.”  

I want to interject here a little bit. It’s like your research on finding out how woefully unprepared the car industry is for disruption. You were calling me about incredibly cool stories about Shaq. It’s like, “He invested in this. He invested in that.” He didn’t invest in Starbucks. His quote, “I don’t think African-American people drink coffee.” Years later, I walk into a Starbucks and I get pissed off that I missed it. What’s interesting is this became a figment of someone’s imagination. Between being brought to you and you going, there was a ton of work that went into making sure you’re prepared to have everything laid out. In case you got pulled in a certain direction, you’re ready to talk about it, which I thought was fascinating. 

If we had David on here, he would probably tell you the same thing. At the time, he was in Big Brothers Big Sisters because he’s been to that event a few times with his wife. His wife is the vice president of Goldman Sachs. They’ve bid to these charity auctions before. They’ve bid on these silent auctions before. Truthfully, it wasn’t just Shaq. We were looking at 7 or 8 different people we were bidding on. David would tell you that part of it was he was in the middle of design engineering and selecting components and our product wasn’t moving fast enough. He was in design engineering hell. He wanted to do something fun that might be able to get some attention to the company, something marketing-related or sales-related. More than anything, he was looking for some diversity of experience because he was in the weeds so much product-related.  

We bid on several different people. All these bids start creeping up from $500, $1,000, $1,500, $2,000, to $2,500. It’s a 24-hour open window and all the bids keep coming up. As they get bigger, we’d like, “We can stop bidding on Julio Jones.” We’re bidding on a whole bunch of Atlanta Falcons that were on there. Shaq was the one we kept coming to. It was a perfect fit to talk to him. It kept going up. We ended up spending $11,000 and we won the bid. David quit telling me about the bids at some point. You know me, I go to bed early anyway. I woke up in the morning with a little screenshot saying, “You won a one-hour mentorship with Shaquille O’Neal. Congratulations.” I sent it to you right away and being like, “Check this out.” You’re like, “What the hell. Why are you talking to Shaq?” I’m like, “I don’t know yet. We’re going to make something of it.” 

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I was in the car going somewhere and I got it bleary-eyed. I looked and I’m like, “Shaq? What Shaq?” What happened between you guys winning and you guys going down there? This is January 2021. We’re talking five months later. Talk to me.  

Big Brothers Big Sisters sends you an email and says, “We’re going to work with Shaquille O’Neal. Do you have any specific dates?” This is Shaq. This is one of the busiest dudes on the planet. He runs a podcast. He has a YouTube channel. He promotes over 30 different products and does advertisements for him. He has a regular host on TNT’s NBA show pregame, halftime, postgame. The charity work that he does is outrageous. He’s an assistant deputy to the sheriff of Henry County in Atlanta. Everywhere you look, Shaq is somewhere. He raps. He has video games. He’s in movies.  

It wasn’t like we won the auction in February and wanted to meet with us. We got silenced for a couple of months. We were okay with that because we wanted our product to be a little bit farther. We were okay with it not being right away. We got an email from Big Brothers Big Sisters saying, “Here’s a few dates to work with Shaq.” At first, they were talking about, “Maybe we could do it at the TNT studios.” We got all excited. We were going to get a camera crew and audio. We can use all these clips of talking to Shaq about our device, car crimes in general and as a police officer.  

The charity reached back out to us and said, “It’s going to be at the Four Seasons at 5:00 on June 9th, 2021.” This gave us about 3 or 4 weeks, knowing the date. In advance of that, all I’ve been doing is consuming Shaq content since February 2021. It’s insane how much time I’ve spent researching The Big Diesel in that time and getting to know him. I’ve been peppering David with little Shaq snippets. I probably have over 100 hours of research into Shaquille O’Neal in those few months. He’s everywhere. He does everyone’s podcast.  

What do you hope to get out of this? 

Going into this meeting, the most aspirational hope is we get Shaquille O’Neal excited enough where he wants to invest in our company and be a partner, help us market it, grow it and do things. Take it back a notch on the aspirations. We’re still in a place where we’re making changes every day to what’s going to be our first device. I did strongly believe that he was going to have some thoughts about our product that came from a different perspective of a guy who’s been a police officer and a guy that grew up in the streets of New Jersey pressured to be in gangs.  

He understands car theft from a thief and law enforcement perspective. He understands it from being early in Ring in the security business. I did believe that no matter what, we were going to learn a lot by sitting down and talking to a guy like that. The third thing that we want to learn from him is how he would go about marketing a product and getting as much attention as possible for a new technology product like this from the start. 

Let’s talk about the meeting. You show up. You’re there. You’ve done all your prep. What do you bring with you? How does it start? How do you get into a pitch with a dude who gets pitched constantly? 

About two weeks before the meeting, David and I built a Google Doc. It was our Shaq prep doc. I’d been taking notes. He’d been taking notes on everything. I listened to 20 to 30 podcasts where Shaq would get interviewed for an hour to the point where I knew his answers. He was on with Conan O’Brien, Oprah Winfrey, Steve-O from Jackass, and Rex Chapman, the Knuckleheads. I listened to all of them. I listened to his podcasts. I watched his YouTubes. David read both of his books. Every bit of research that we were getting, we would dump into this Google Doc.  

David and I started having conversations daily about our approach. How are we going to build rapport? How are we going to break the ice? We would delete things. Adam would bring it back in. What we ultimately decided on was David was going to leave by thanking him for being involved in the charity. He was going to mention that both of them were military brats and that Shaq’s dad was stationed in Germany at the same time that David’s was stationed in Germany. The two of them lived in Germany at the same time, which I thought was pretty interesting. We decided that’s going to be our icebreaker.  

We built a list of questions that we would at some point like to ask Shaq and that felt choppy. The more we went through it, I said, “David, we need three main areas where we need to ask him open-ended questions. All we should do is keep peeling the onion by saying, ‘Tell us more.’ The conversation will be more engaging than if we pepper him with questions.” Everything in the prep, if you think about it, Frank, we talked about what we should wear.  

We’re meeting in a lounge with Shaquille O’Neal, 7’1’’, 380 pounds. Where are we going to sit? How early are we going to get there? Are we going to be able to get a corner table? We don’t want to be sitting in the middle of a Four Seasons restaurant lounge where people are asking for his autograph the whole time. How do we get the corner table, wherever that is? How do we case it? What do we wear? Should we wear a tech startup? Should we come across as the cool tech guys with our Keep t-shirts? Do we wear a shirt and tie and be as respectful as possible? We ultimately decided on sports jackets and button-down shirts with jeans and sneakers. That was to show him as much respect as possible.  

Shaq, every night on TV, wears a suit. We didn’t know if he was going to wear a suit and then go to the studio. Along the lines of being the best-dressed person in a meeting, we didn’t want him to come in and be better dressed than us. It will look like disrespect. Do we bring a camera crew? We ultimately decided no because we felt like he would be more guarded and it could start the meeting off bad where he’s like, “Why are there cameras here? I’m not wearing a mic. What are you going to do with all of this?”  

The truth is if he wasn’t interested in working with us after, how much would we do with a bunch of footage of us talking to Shaq? At some point, that would wear off. You can’t keep using it. At some point, if I were Shaq, I’d be like, “Quit making it seem like I’m part of your company.” We decided not to record it. Little things. Do we ask for an autograph? The answer was no. We’re not going to ask for an autograph. That’s not what this meeting is about. If we want an autograph, I can go on eBay and pay $300 for an autograph of Shaq. 

Do we take a picture with him at the end? The answer turned out no on that. This is a business meeting. Let’s not fanboy out. We tried to think of every contingency we could think of, Frank, of how this would go and where it was going to be and all that. The meeting was going to be at 5:00 at the Four Seasons. Big Brothers Big Sisters was the one coordinating. We still hadn’t even interacted once with one of Shaq’s managers or handlers. I flew into Atlanta that morning, got to the office with David, and did our final prep.  

We got to the Four Seasons an hour early for this 5:00 meeting. I still was half thinking he’s going to cancel because he’s that busy. I still believe that was going to happen right up until we got to the Four Seasons. At around 4:00, we got an email from Big Brothers Big Sisters saying, “Shaq is going to be an hour late.” He was going to come at 6:00. Now we had two hours to hang out with the Four Seasons and prep a little bit. His manager, an incredibly nice guy, got there at 5:30. I get the sense this is pretty normal for him. He gets to places before Shaq does to maybe case to joint a little bit. There’s got to be safety concerns for Shaquille or who’s there, what they’re doing with a guy that big and that well recognized.  

He got there. He had his kids with him. He came over, shook our hand, set his kids down at a table, sat down, and talked to us for ten minutes. David and his manager were at Georgia Tech at the same time. They had that in common. He’s an incredibly nice guy. He apologized that Shaq was going to be a little late. He told us a little about what to expect. We told him what Shaq could expect to make sure that was in line with what they thought because Shaq gave his time up. We wanted to know what maybe Shaq’s expectations were.  

LMSM 42 | Shaquille O'Neal

Shaquille O’Neal: So much can be learned just by sitting down with the right people.


We had sent a long email with a bunch of who we were as a company. We found out from his manager there that Shaq never read that and never got to them. We were like, “That’s cool. This is how the meeting is going to go.” We sat and waited until 6:00 when he would arrive. By the time Shaq got there, the Lounge at the Four Seasons was crowded. All the tables were filled with people eating dinner. It was a pretty crowded lounge but we had the best corner where there was a ton of privacy. We had two walls behind us, a little bit Sopranos style where you always sit with your back to a wall.  

That was a dynamite lead-in. Part one of Ian’s meeting with Shaq is now concluded. Tune in to part two where we sit down with The Big Diesel who blocks out the sun as he walks into the Four Seasons and learn about how that meeting goes. The juicy part is just beginning. 

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