A Conversation at Alfred Williams & Company's annual sales meeting

This was a conversation from an annual sales meeting with a dealer for one of the leading furniture companies in the world. When they asked me to speak, I said, let's have a conversation instead. You and me, let's plan it. Let's really spend the time to understand what you want them to take away, how you wanna impact their lives, and let's do the prep work to make you the interviewer. And let's drive a conversation that also turns into a really meaningful Q&A with the group of people there. Personally, this was one of my favorite, most vulnerable conversations or talks I've ever given. I would love your feedback on it. I hope you enjoy it and let me know what you think. Oh, and one more thing. Thanks to Ted for inviting me to do this talk. I had a blast. And also thanks for being an amazing interviewer. This was recorded on a phone that we set down in the middle of the table on an app we use called Otter. So the audio is not the best, but you can hear it and I think it's fun.

I am so excited to, um, to be a part of this, the kickoff of our time together. The next few days are all about you and you are a great example of what makes our company unique. So I think that this discussion is gonna be really meaningful and I'm hopeful that you get out of it what I have from building a relationship with Shane.

Lower your expectations though.

Uh, You know, I think we know that a great amount of our lives are spent in our careers. I heard an interview recently and the conversation transitioned to the topic of work-life balance. Who's heard the words work-life balance this week? And the interviewer stopped for a second and said, "Wait, wait, wait, wait, timeout, timeout. Work-life, isn't it just life?" It is simple but felt like profound. We don't unzip ourselves the minute we walk into the door when we get home. They really are one in the same. So what's really cool about today is we're going to spend some time talking about life as it relates to vulnerability, authenticity, and being present. 3 very powerful things that we're going to unpack together. I'm so excited to introduce Shane. He sparked such a curiosity in me since I met him and led me to redefine leadership, how I work, how I negotiate, how I think, how I speak. So with that said, who are you and why are you here?

I'm really glad to be here. First off, I would love this to be a two-way conversation and we're just kind of— my favorite thing is doing Q&A in general. And so if anyone has questions, you wanna interrupt me, like, I think he's full of shit, it's all yours. Here we go. So, uh, oh yeah, apologize for my language. I'll probably drop a few Cuss words. I really don't mean to offend anyone. You know, it's funny. I feel like I'm just like one of the luckiest people alive over the last like 15 years of working in technology. And yeah, I come from a little town in Peoria, Illinois. You know, I can like go through the little, "Hey, I've done all this stuff," on the fact sheet. But I kind of want to share 3 stories about, you know, my background as it relates to being here, why I'm excited to be here, and how I think I've changed a lot of my views over the last decades especially. And, you know, it started out— I was just in college messing around on the Internet and I found Twitter and I was like, 2006, '07 timeframe. And back then, like, Twitter was— even Twitter today, everyone's like, "Twitter is so stupid." And everyone was always making fun of me, it's a joke. And I just found this, like, passionate community of people that were all inspired by the Internet and the ability for anyone to talk and say something online. And that was— I I found that cool. I didn't go to college for technology. I went to Western Illinois University. It's the opposite of Stanford. I've been in San Francisco through the long last 10 years, and everyone, you know, it's like, "I went to Harvard." I'm like, "I went to Western Illinois." And so, that led me to meet a guy in Seattle named T.A. McCann, who, you know, my first work experience, it was just my curiosity of, "Cool, I like the social internet thing. It's kind of interesting. I think it could be more powerful in work and life." And T.A. was just this amazing mentor. And I met him actually through a person on Twitter. It was just random. Back then, that was so weird. Meeting someone online was not a thing that happened yet at all. I remember that being like, "Oh, the offline and online worlds are connecting. This is pretty cool." I didn't really think of it as a business. I just thought of it as like this cool side job. And T.A. was building a company which was mining your email inbox to find news about anyone you've ever emailed. And he was doing it to help know more about who you already know. So if you've emailed 10,000 people for the last 3 years, there's news about Ted today, I get an email, "Hey, you might wanna reach out to Ted, there's news about him." Great sales tool. And I was like, "Ah, I don't really know anyone with news about them." 'Cause I'm in college, no one had news about them. And I didn't understand business. I was like, "I don't know, that sounds pretty dumb. What about the social internet? It's kinda cool." And he was really a visionary of like, "Yeah, the social data on top of email would make me smarter in business." And he really understood it. And that random guy ended up just kind of taking me under his wing, invited me in to go build Gist together, and, you know, in under 2 years really went from zero to what's called today like a social CRM, really kind of competing with LinkedIn. We got a cease and desist from LinkedIn. That's how I knew we were doing something right. And that moment in my life was the moment where this guy ends up being a legend in Seattle. The person we're working for is Paul Allen, the founder of Microsoft. And that's who he was building the tool for on top of his inbox, and he was our first million-dollar investment. And then 2 years, we're going from 0 to 100 million people on the platform, and BlackBerry acquired it. And I think the moment of the lesson there for me and my background was being young and ignorant and lucky is the worst thing that could ever happen to you. Because then you become confident and you think you know what you're doing, but you don't. Down. And that led me on the next journey. And what you don't read on the bio is after that happened, I moved to San Francisco because that's where the— you know, it's like you want to play in the major leagues, go to where like the best people are playing. The capital's there, the talent's there. And after living in SF for 10 years, I will say it is a different place for people building technology. The way things happen there is at a speed that's unlike anywhere else in the world. But it was a bunch of white bro tech dudes that look like me. And I wasn't aware of it at the time. And so the next company, Zarli, actually, you know, it was right at the moment when you had Uber, you had networks of people that you could hire with a mobile app. It was called the push-button economy. That was happening about 2010. The CEO of Lyft is a good friend of mine. He was an investor in Assist. But at the time, like, we all didn't know if any of this was gonna work. And it's really weird now to look back a decade later, and all of a sudden we're all kind of like, "Hey, check this out, I can like, I slide over if I want to ball out tonight and get a black car instead of an UberX. And I'm like, oh, that's a cool feature. I don't know if that would work. And that was the— we were in this like very optimistic time. And Zarli ended up being this overhyped company. I think we were very unself-aware. We ended up with tons of money. We raised $35 million. Everyone lost their money, which you don't read in the bio, right? But it's very important because the company's still alive, but it got recapped. But at the time, we were so validated by everyone who was involved that we didn't focus on building a company that customers love, and more importantly, building a place that people love to work. And I think about 3 years into it, I was in this moment in the office, and I remember being like— and I was leading all product. There was 4 of us when we started in a loft, and all these things we didn't really take intentionally became things that I thought about later. Like, I don't know, if you have a family and kids and the founders are bros sitting in a loft till 9 o'clock at night, it's probably not a great place for, you know, Liat, who is one of my favorite people I ever hired, for her to want to work and like spend time. And I make her feel bad because I stay there till 9 o'clock and I don't have any kids. And I wasn't aware of that at the time. And the moment it happened, I realized we had a cool office. We had Meg Whitman was the head of our board, and Ashton Kutcher was our first investor, and all these big names. And 3 years in, I'm sitting there in our office, the swank office in downtown. We're not making shit. Like, we don't make any money. We make like 12 cents in revenue. Because it's not really working. But we have tons of funding. And so there's this disconnect. And I remember thinking, wow, we have 50 people here. We have amazing office. We had a skee-ball. We were the epitome of Silicon Valley, the show. We have a skee-ball table, ping-pong table, all this cute stuff.

You have beanbag chairs?

Beanbag chairs, Steelcase furniture, probably the main problem.

Yeah.

We were the— what was their— Turnstone? Or what was the startup line?

Well, that's not swank, but if you thought it was swank—

No, so clever to us. The CEO knew our CEO. And we were the first company ever to get their startup line. And they gave it to us for free if they could shoot the video in our office to feel like they were going into tech startups. So they used our office and had set this really plush office. We're spending like $25,000 a month on like— and we had like 10 people at the time. It was crazy. And it was just an abundance of money, but also It was really bad management on our part. We didn't really know. Like again, I was like, I think I got lucky and I was like, "I know what I'm doing. I'll go do this." And that was a huge lesson for me in the Zylie game. And I remember 3 years in, everyone was miserable. And I looked around, I was like, "I created this. My team, the people." And I was like, "We have all the cash in the world. We can do whatever we want. We have this cute office of fun and happy and nothing None of us are being honest that it's really not working. And I was really like trying to tell people what to do. Like, "We don't know. Get on board. We need to go do this." And like that was my— I thought what leadership meant and getting people on board with what we're gonna go do. Everyone ended up quitting. We recapped the company. Kleiner Perkins wrote it off and they invested $35 million. We re-raised $2.5 million. Beau moved to Kansas City. I was like, "I don't wanna go to Kansas City." city. So I'm gonna like step out. I'm done after 4 and a half years. And you know, Bo's still doing it today and actually just turned it around and it's going. I literally own, I think, like point as many zeros as you can think, one. That's about my ownership. I don't remember what it is because everything got reset and whatever. The lesson that I learned there is that you can have all the cute office furniture and games and startup-y, but building a culture of doing great work and building a great place to work and a place that is diverse at its core, a place that celebrates doing really good work but also living a balanced life and things like that. Like, you go through this and I think we all grow. And that really led me to do, which was my next company Assist, the last 7 years. And I was really lucky to find, my co-founder was the founder of Geek Squad and the CTO of Best Buy for 10 years. And he is a partner. You talk about intention. Every single detail of the Geek Squad uniform and the way they do onboarding and the detective nature of it and how they do training and the manuals they follow and how they— all of it is— there's 25,000 geeks in the world and it's still using the same playbook and logo that he designed on a napkin in 1993. So having him as my partner, we went into it completely differently. I think And that's where my whole journey kind of changed of how do I be the place where Liat, who has two kids and her husband, are proud to work at? How do we be the place that is curious first and I don't have to have all the answers? How do I lead in a way that is I should make the least amount of decisions? I have the least amount of information as the CEO. Why should I tell anyone what to do? This journey has been this like crazy experience. Like, letting go of your ego. How do you even get there? Working really hard to do that. And after about 45 employees, no one had quit over 4 years. And I feel like we finally got to a place where we unlocked something that changed how I looked at business, and it's more about life and how to make it a great place to work. 'Cause if you teach people how to be better at work, they take it home and they're better at home. And I think it's very important for all of us to take those lessons and really realize that it's not work-life at all. It's like just life and its work-life harmony really, how it all works together. That really has been now my mission is just to, you know, really help create places that are the best place to work. It doesn't have to be a place. We operate remote first. We have people in 15 countries and very global at its core. I published our diversity stats online. We were 60% women by the time we got acquired. I was very vulnerable. I put our stats out when we were 98% white dudes. And I said, "From this day forward, I'm gonna be aware of it, I'm gonna address it, and we're gonna talk about it." And I think, especially for like white men in today's world, to do that is actually very important to empower and build a culture for everyone to feel like they can be a part of. So that's a little backstory and kind of where I came from. And I think where everything kind of flipped in that moment in the middle when it all failed. And it led to, you know, I hope building better companies. And, you know, a lot of capitalism gets a lot of flack these days, and, you know, business and whatever. And I think business is one of the greatest tools for change. So I'm excited to be here. I'm excited to hear from you. Like, I don't know what you wanna know. I'm not a public speaker expert. I don't really— I'm not a Tony Robbins-ist thing. So I'm just curious to learn more about what you're up to. And have the opportunity to kind of share stories.

You understand now what— yeah, that's right. So my hope is for each of you that you leave as curious as I have from spending some time talking to Shane. You talked about—

I'm also Ted's brother. Just call it out. Every single person we meet, from the person who introduced us, he stops me. I'm getting ready to leave his house and he goes, He goes, "You look like my buddy Ted." And then later that day, I'm sitting next to him. I don't think I look like him, for sure. And he goes, he's like a furniture dude in town, if you'll meet him. And I was like, "Cool." And I'm sitting in the pool and we meet. And he goes, "Yeah, yeah, I just work on furniture." I'm like, "You're Ted." And that was like this moment, I was like, "This is incredible." And then I was like, "I have hair." See, I was waiting for the shift.

See how the hat changes, the attitude changes? Uh, it's a perfect transition. So I hope you leave as curious as I've been, and we have a lot of good things to talk about. So something you said that I think is really interesting— so how does— and you touched on a little bit— but how do you, how do you shift from being this young tech entrepreneur to sitting here talking to a group of salespeople and ops managers and design managers and with talking about words like vulnerability or presence, you know, like where's that shift? Obviously it came a little bit from some business—

getting your ass kicked, basically—

business experiences, but touch on that a little bit more.

Yeah, you know, it comes from really getting punched in the face, and being a CEO is one of those things that everyone glorifies it and it's really lonely at the the top. And unless you're really self-aware and asking questions and being open, people won't open up to you. And so it came from the moments of finally getting to that self-awareness and failing at the second thing allowed me to be like, oh, like, why am I trying so hard to prove that I'm successful? Like, all these moments.

Failing at the second thing.

Exactly. Like, once coming to terms with that and whatever. But I think the biggest secret is I've always just been genuinely curious. Like, I was the— my grandpa, I used to say, like, why, like, 5 times. And my grandpa was not curious. He was like small town Glassford, Illinois, like, I know how life works, and you do what you're told, son. And I was like, why? And then he'd be like, you say why one more time, I'm going to kick you out of this house. I'm like, all right, cool. And so I've always just been generally curious. And about 2009, I randomly kind of— I don't even know why I started it. I was in my basement. Seattle. I moved out there. My brother got me to move there. That's where I met T.A. And I was like, I kind of saw it as like a way to meet anyone in the world. Because I saw the internet, I was like, that's the power of the internet to me. I can literally talk to— there's no— like, you're connected to people. The whole world is connected. Connection's a commodity. So now it's, do you have anything to say that's meaningful to them that they care about? That's where we're at. That's the state of the internet today, in the world. So I'm sitting there, I'm like, OK, I see that. And I'm like, I'm just going to start asking people one question I don't think they get asked on Skype, hit record, and post it online. So I just started reaching out to people, "Hey, I'd love to ask you one question you never get asked." And literally, probably 95% of people wrote back and they're like, "Yeah, sure. When are you gonna do the interview?" And I'm like, "Hmm." First off, that's a really interesting hack to social relationships. So I'm like, "That's cool." And it became this thing called Ask. And I've been doing it before podcasts were like podcasts, but it was really just a podcast interview. And if you If you go back like 10 years ago and listen to them, I'm like, I'm a terrible interviewer. I'm like nervous, like, hey, we're here with Jason today. We're gonna do an interview about tea. Like, let's talk about tea. Jason, how's tea? Like, it's online. And then you learn that no one actually gives a shit about you and is not watching you when you're bad, and still being out there is fun. But creating content and building those relationships has been a complete change in my life. And so then what I realized, to answer your question, is Every time I would get off a call with someone I never thought I would have the chance to talk to, they always changed my mind about everything I thought was right in life. So then I get to this point, I'm like, I don't know anything. I know a little bit about something, and I think my philosophy has become, be really great at what you know, but be really open and honest about what you don't know. And getting to that place where you're really confident to say I don't know, we actually practice it at Assist. This guy named Stéphane, he's from Monaco, he wears sweet watch, he's got the fancy pocket thing, and he'd always be— sorry, I'm sure someone has a pocket thing. Nicholas, you're hiding behind the plant, Nicholas. There he is. And it was fascinating, like, we'd get in the middle of conversation and one of my favorite things was ask him a question that I knew he didn't know, not to trip him up, but just to practice. He literally could not say I don't know. Because he was so built in this perfection. I have to really be perfect and show that I'm perfect. And then finally, by the end of the sis, that dude's in therapy with me. We're hanging out with the counselors. He's like, "I don't know anything." It was great. But that really was the intention of the company. And so going back to your question, getting to a place where you realize that all of us in the world know nothing about everything and just a little bit about something. Is a very freeing place to get. And then you get to the next place of like, stop trying to act like you're so smart. Because we're kind of all just like trying to figure it out. We don't all really know. But we can write fancy bios that looks like we do. But it didn't say that he lost $35 million on that second part. And I think that's where getting there is like the best thing ever. And that's been where also that becomes the superpower. 'Cause when I was hiring, Michael, who's my co-founder of Ask but also was my coach for interviewing and kind of really helped change a lot of philosophy for me. Or Robert, I never believed I would have the chance to hire the co-founder of Geek Squad ever as my co-founder. Or Liat, who had led all revenue at Twitter from $0 to $100 million, became our Chief Revenue Officer. Or Stefan from Facebook, or a head of Apple Pay I hired to be our Head of Product. And all these big companies, and people would say, you know, You gotta compete with Perks and they're making a lot of money. How are you gonna get people from Facebook to work for you? And they have free lunch and they have all these cute desks and they have open office space and all this stuff. And no one cares. People want to be able to make decisions. That's it. That's the whole advice. You want to get people to be empowered and love your company and culture? Give them decision-making ability and give them control. And tell them you don't have a clue. And I would go to Liat and I was like, "Here's what I want you to do." whatever you want. I have no idea how to be a chief revenue officer. I have no idea how to run this part of the company. I just want to learn from you and build a company that we're proud to work at. And this is our intention of the company. And we recruited everyone. And that was, that was really the— getting to that point of curiosity and vulnerability is the superpower.

You mentioned Ask the podcast and Michael, your coach.

Yeah.

I'd love for you to share, share with the group, talk about making less decisions about kind of what your rules to do business with Michael were?

I think that was— Yeah. It was funny. First off, I would ask him— he co-founded a podcast called Radiolab. It's probably one of the number one podcasts in the world and it's incredible. The level of production of Radiolab is incredible. He comes from WNYC, which basically invented podcasting back in like 2002. And so, he's kind of a legend guy in the industry. And We were getting ready to, you know, everyone's in a room like, we need a marketing budget. And for what it's worth, we had technology and salespeople at our company. That's really where we focused. And then we tried to hire everything outside of our company for any other— we had an HR team out of Kansas City, Nancy, who's awesome. And we really kind of had like an outsourced type model. And we really focused on, we're good at this. We sell to enterprise brands. We build AI technology. Those are the two core teams. And then we need to do marketing. I'm like, "Okay, what is marketing? What are we gonna do for marketing?" I love marketing. Really, it's powerful. Storytelling is everything. And I went to Michael and I was at dinner and I didn't know if I was gonna get to work with him or not. And then I realized how expensive he was, so I had to move like 4 budgets over to hire him. But I was really determined to work with him. But it ended up being one of the greatest kind of moves I think we we did. I wrote to him and I said that night, I said, here's what I want to do. I'm gonna make no decisions. I have no idea what I'm doing and I want you to just coach me and I'll be vulnerable and have you just tell me what to do. And that moment was the moment that the relationship was built. And he's like, I'm all in, let's do it. He brought in Paul, the producer. It's one of my— I mean, we produced a whole season of it, like 45 episodes. And then all of a sudden, having this guy behind me who's produced and done interviews with everyone and a coach to everyone. He's the coach of Jad, who's the guy on Radiolab. Changed— I mean, I was already working on this stuff. This guy just changed everything. And he helped us prep for this talk. And when he talks about intention, and here's the point of the day, here's what you want people to take away, and he wrote this, my ass is all over. I got thoughts everywhere. I'm just like, Michael, help. And he comes in, he's like, here's your 4 points. Here's what the point of the day is. Here's how we're trying to do it. Here's why we're trying to impact people's lives. And when I had him behind me, it was just like the superpower of being vulnerable to him and open to him allowed him to be a great coach. And you have to get there. It's really hard to get there because everyone's trying to fight back or prove. But you're like, I don't know, just tell me. I'm open to that.

What do you feel like he uncovered What was the kind of the initial thing that he uncovered that you realized you were maybe doing wrong before? Like when, what was that, what was the first bit of advice that, that really changed everything?

So one thing, this is a big one for me actually, and I think for everyone. One of the biggest things he ever told me was, when before I met him, I would do hours of research on who I'm about to interview. If I'm gonna interview Ted, I would research Ted and I would know he works in Nashville and I think I know everything about Ted. I'd come into it and I'd have like, these are the 10 questions I'm gonna ask Ted. And you prep, it's like sales, you're getting ready to go to a sales meeting, you have all your questions. And that's like my agenda, right? And the first thing he said to me, he's listened to some of my podcast interviews and he's listening to me do this, and he said, the biggest thing you're missing in life right now, and the biggest secret to doing interviews, sales, or anything about relationships is do the prep work, forget the prep work, and never get to question 2. And I was like, what do you mean? He goes, here's what you're doing. All you're doing is your agenda, and you're not listening to them because you're so worried about the next question. He goes, if you do an interview right, or you build a relationship right, or you do sales correctly, You never get to question 2. And he said, you have to purely be present in the moment. And it's really hard to do. Being just active listening and present is so like almost like cheesy. The first time he told me, I'm like, that's real good advice. Pay attention. And then you really focus on it. Am I listening? Am I thinking in my head about what to do next? Am I insecure right now? And then you get into active listening and really paying attention. And he goes, "Listen to every word he says. Listen to every single word and then ask them another question about that word. An hour later, you'll never get to question 2 and they will be like, 'Thank you, I've never experienced an interview like that.'" And that moment for me, I really took it to heart. I was like, "Okay, don't get to question 2.

Look over my notes." There's notes on the back. That's a problem.

And I did it. And you can, I mean, not like I'm a great interviewer, but you can drastically tell the moment 3.5 years ago when Michael stepped into my life in all my interviews than before. But in everything, and all of a sudden I'm like, oh, presence and paying attention in a world that's so distracted and everyone's got new shit and no one's listening to anybody. Just by actively paying attention, you'll get to whatever they want. And you'll never get to your agenda because it's your agenda, not theirs. And then the second piece of it, he goes, and in my head I was always trying to like, yeah, Ted, and here's what I think about that. And I would come back to me and I would drop some real knowledge smart bomb because I wanted everyone listening, and if the CEO of Salesforce listened to my podcast, then he'd be like, oh, Shane's smart. And he goes, stop trying to be smart. It's not your job in that scenario to be smart. Your job is to be curious in the relationship and the knowledge. The listener doesn't want to care about you and your insecurity to feel smart. And that was a huge— like, blew my ego. And that was a moment for me. Those two pieces of advice: one, you have to really get there with yourself and be insecure and be vulnerable. And two, doing it actively. Changed everything. Like, it really changed how I thought about presence and paying attention and asking questions, preparing for things. Oh, prepare, but that's what I want out of the meeting, not what they want. Let's just focus on what they want. I don't even know if I ever get to the next agenda items. We'll get to what really needs to happen. And those two areas for me, like, I was like, pfft. And it's one of those things where you hear it and then you're kind of like, "Yeah, whatever." And then you do it and then you're really focusing on every meeting. What's your name? Melissa. Melissa. And when I'm talking to Melissa and you're repeating your name, "I'm Shane." Like, things about interactions of how you interact and how you say names. And there was one guy we interviewed for another podcast called Chris Voss. And he led like one of the largest FBI negotiations in the world. And he talks about make sure they know your name and repeat it. And the psychology of the interactions. But it starts with being present and really understanding that you're there to serve them, not to serve yourself. And that, I mean, from then on I was going to meetings like, "Oh." Like, every day I'm just like— and I think the hardest part about all this is going through your entire life thinking you have it figured out and then dropping a bomb on yourself and being like, every single thing I thought is now like Shane's telling me is the opposite. And that's how I felt when I met these people that were— and you just meet pros, and you meet someone like Michael. Like the call yesterday, within the first 30 seconds Ted looks at me and goes, oh shit. Like, he's like— and funny, when you deal with pros, it's actually the simple stuff. The bullshit people tell you all this like tacky advice and tactical stuff. This is a new tool, and I'm a speaker and want to be successful, and like all this stuff. And the pros like, here's the deal, get in your own head, focus on it. Today Ted, he's like, you know, I'm in my bullets. I'm like, here's what you do, Ted, get on stage, forget your notes, and just talk to me for an hour and a half. And like, then you get there with someone like Michael who really prepped, is like, it changes, I think, how you do everything. And conversations are sales, are BD, are recruiting, are leadership. Leadership, and that kind of, I think, extends to everything.

Yeah, yesterday was a pleasure. So we're jumping on this call with Michael. So, you know, 60 seconds into it, I look over at Shane and I'm like, oh my gosh, like, this is— because what he did was he said— we had put this Quip document together where we had just like brain dumped all these ideas that we had.

Can you hear him in the back?

We had dumped all these ideas into a Virtual Document that it started, we started kind of somewhere different. We actually started with the story about how to be the, how to be this great interviewer, and then it just kind of morphed. But so Shane told me that Michael was going to help us pull it together. So we got on this call, and 60 seconds in, he says, well, Ted, now I, now that I know your voice, here's exactly how we should probably start this thing. And that's when I looked at Shane like, now that I've known you for 60 seconds? Oh my God, just when I thought I was really intriguing and really complicated. But it was awesome.

And anyone who knows Ted.

So which is a great transition. So I'd love for you to talk maybe a little bit about how does insecurity maybe meet this ability to grow or be curious. Admission yesterday, we get off this call, it was great, learned a lot, we're feeling really good about what we're doing, and I was walking into the hotel with Shane and I started to ask him a question and the question was very insecure and it was, "Hey, how do you think I did on that call?" And it came from a place of like, I'm on the phone with this guy Michael and he's—

Yeah, we talked about this yesterday. Right?

Like, how do you— How do you, how do you, what did you, I was searching for Shane to say, oh man, you did an awesome job. Well, it's a, it's a, did I do a good job on that call? It's a binary question, which I know you'll talk about like yes or no. Well, is he gonna crush me and tell me no, you blew it and Michael thinks you're an idiot and you know, like fingers crossed on tomorrow.

So I didn't, 30 minutes in, jury's out. Right.

So I didn't ask the question, but I'm sharing it because it was a moment where I was able to step back and say, why are you asking that question? Like, what's really leading to that? Which I think is really interesting related to your journey as to like the intention of your questions and what are you really trying to seek? And are you willing to be vulnerable to say, God, I was going to say that, but I want to explore why. Like, what do I do with that?

Yeah, I mean, it's funny. The biggest thing I learned— her name was Liat, our Chief Revenue Officer. And having a leadership team that always talks about this, having our leadership team be 80% women was probably the greatest thing I ever did, to be honest. Because it taught me a lot of this stuff of feedback is a gift. And I think I learned that through working with people who also truly believe that. The funny thing about your question is you weren't seeking feedback, you were seeking validation. And that's funny. My co-founder Robert always says, "People always come in for advice, but what they really want is validation." Because they always call, they'll talk for an hour about their idea and be like, "What do you think?" And they just wanted validation. How you ask for feedback and how you give feedback is what to practice. And what's interesting about feedback is, if you ask a binary question, levels of seniority then come into play, leadership or sales, whatever. And David Marquet, this guy, he was the head of the Navy boat, the Santa Fe. He was a captain in the Navy. He's one of my favorite, like, almost leadership coaches. And he's— we have the same ethos on life. And he really, for the last 7 years, became my Bible of assists. Like, he was behind me. We've developed a great friendship. And I got the opportunity to fly down to Florida to interview him. We posted the podcast about— for his book that launched called Leadership is Language. Best book on leadership. On leadership I've ever read that is very, very tactical. It is down to the words you use and why they're wrong, because we come from an industrialization society, not a knowledge-based society. And we haven't changed how we worked because we don't understand that the language has to change. In the book, you'll— I read it and I'm like, oh my God, I say everything in this book that he says not to say. But it's amazing to be aware of. And the feedback area that you're asking about, What he taught me, he said, "Don't ask binary questions because the person across from you will always default to the least friction." So, if I was reporting to you, which I know some people do, they might be here, I don't know. You ask that, "How do you think it went?" They're gonna say, "Great." Always. They're gonna default to the least friction that is validating whatever you wanted to hear. Instead, don't say what. A trick is is to use how as the question, not what. Starting a question with how forces you to think and have thought and present the environment that is safe. Like, instead of saying, "Everyone good with that decision?" Say, "How could this go wrong?" Okay, someone's got to answer. You made it safe now for both in client meetings too, getting to that with a customer, like, "How could we do this wrong?" Oh, they're telling you now. Oh great, that's great knowledge for me to know. I know now how not to fuck up. And using how is one of the most powerful tools, like a trick almost, to solicit feedback and give feedback in a very powerful way to make the safe space for the other person to feel comfortable doing it. And so I'm like, oh yeah, like you have all your tools, Mr. Leadership Guru Guy on the podcast. We did this on the podcast and I said, Does it work in personal life? And he said, yeah. He said, walk into Starbucks today and said, how was I as a customer? And I was like, interesting. They always ask me, how did we do serving you? And I was like, how? And I did it in Nashville. And she's like, you're great. And I was like, I feel great now. But then I said, what about with your wife? And he's like, you know, I've been actually meaning to do that. And I said, why don't you call your wife right now? So on the podcast, he calls his wife, and I said, what is the way you would frame this question to build a better relationship at home? And he said, you would use the word how, and you would say also a scale. So he calls his wife and he says, the right question is, on a scale of 1 to 5, or no, how can I be better as a husband? What's one thing that I can do to be better as a husband? And she ends up saying like, tell your thoughts out more, out of your head, because you're such a diverse thinker that I never really know what's going on. And he said, how am I doing right now on a scale of 1 to 5? And I wrote down before she said it, I was like, 2. She's like, 2. And I was like, gotcha.

And how did he react?

And he said in the past when he was the head of the Navy and submarines, like, that was a mindset, he said, I would be so nervous to get that feedback. But all of a sudden the feedback is such a gift and he felt so at ease. It's like, "Now I know." And 30 days I'm gonna follow up and check back on that moment. And you know, to tell a longer story here, so there's a cool moment that like— there's moments in life where you kind of just like don't know why it happened, but it's just everything goes goosebumps and you're like, "That was something." I just like, what? I don't know. I don't know if you're religious, spiritual. I was like, "Whoa." And it happened with David. So our company was launching launching, and it has to do with this how question. Our company was launching probably the biggest deal of our entire life in 2018. The executive team of Apple's flying out, AirMark's there, a competitor is also in the deal, but it's all of our technology, but we had to like use them for a little part. So there's a lot of like tension there. And this lady named Amanda is our head of partnerships, and she's kind of ran this deal for almost 9 months. And it's gonna be the first time ever without an app You can buy beer in a seat at a stadium via text messaging on Apple Business Chat with Apple Pay built in. And you can just scan a code on the back of the seat, say, "Two Bud Lights, Apple Pay," beer's delivered. So it's like a pretty radical operations changes. There's a person at the old stand, like pre-Uber, like they're waiting for you to get in line. Like, there's no Uber anymore, there's no line anymore. And all of a sudden, the hawkers, we built a bot so it was coming to their Apple Watch. So they're just walking around, not like, The friction of collecting money is gone. So they're just walking around with their beer. It's like 2 Bud Lights, Shane Mac seat 134, section 2. So like frequency goes up, caught, reorder. It's a huge— it was a simple thing, but it was a big deal. It's probably our biggest deal of our company's life, actually. And we're there in the morning of this day, 5:00 a.m., and we went out that night before, and I was so calm. I was like, man, we're just gonna crush it. Nothing works. 5:00 AM, nothing worked. The technology's breaking. We don't know why, because we're load testing it. 5:00 that night, the Phillies game's happening no matter what. We have the whole stadium lined with every single seat, bright green QR code, scan this to order beer. It was one of those moments in my life, you know, we get all nerds and we're sitting at computers, and you just forget things. And then you walk into the Phillies stadium, and you're just like, damn. Like, it's big. And you're like, oh, this is real. And then the Apple team's there, and it's really meaningful for them, actually. It's a huge deal. And I'm like, okay. So all of a sudden, I had invited David because I was like, hey, I'll probably have some time the day of. We can hang out. We could do an interview. Your book's launching soon. Let's just get to have lunch. All that's out the window. I'm like, David, I'm on like SOS mode, and you're welcome to come hang out, but there's 30 of us on a group chat with people in Europe and America and West Coast. And we have a big problem. It ended up being the coolest blessing ever. The guy that I've trusted to really take his philosophy of giving away control and giving away decisions and build a leadership philosophy around is now standing behind me while I'm doing it in a pretty crisis moment. Get through the day. About 1:00 PM happens and Amanda is freaking out. I mean, this is her biggest move of her career. For us, it's as a company. She knows that. I know that. Our intern Adam's there, who's phenomenal. I tried to get this guy to drop out of Cornell. I was like, "Why are you an intern? Like, don't go to college and then come back and work for us. Just work for us and like go back to college." Didn't work out. He went back to Cornell. And he actually is the producer of Ask now. He works on the podcast. He's amazing. Anyways, we're there, and this other company had been really kind of a lot of friction. And they were doing the agent side, and their only job was to do analytics. And whenever an order came in, Bud Light 2, it would show up in their dashboard. So the person that's giving away the beers could see that we need to give 2 Bud Lights to the person delivering the beer. And like, and it wasn't really built for that. They were kind of hacking it, and they didn't really tell their boss. They didn't bring up the problems that it could be. And 6 months earlier, I told our team, I said, here's the deal, this company has no incentive to make this work for us. We're here for Apple and the deal with AirMark, and this is what we're here to do. Build their software as a backup plan, so when it fails, we have our bases covered. And about 1 PM that day, I get this call from Claudio, who's our head of engineering, and I'm like, "Hey, did you— their stuff's not working." And what happened was, it was just that they were hacking their own product to do something it wasn't supposed to do. 'cause we really needed like a POS dashboard, which is like called point of sale system, which is basically order comes in, I did it, and like it has a queue of all the past orders, and that was really what we were trying to have for our people that were behind the scenes. And we had built the perfect one, 'cause we built it just for this use case. And Claudio was like, "Yeah, yeah, boss, obviously we built it. It's here." And he like turns it on, and I was like, "Magic." And we're at this moment, and I'm like, "Holy shit." So I was like, "You guys," "Listen, we're not gonna make you look bad in front of Apple, but you've been a pain in the ass to work with, and you're done here. And you're gonna go back, we're gonna make this work, and it's gonna be very successful, and you will do great. But get out of the way." And Amanda, at that moment, was still like, never used this software. She's like, "I don't know how it works. I haven't even seen this thing. Where did this come from? You like magically made software appear out of a box?" And like, I'm like, Claudio's in like my hero. Like, at this moment, Carlo— we flew Carlo here from Italy, he was on the team— and he's there, he's like, "Hey, boss, obviously we built it." And I'm like, "You guys are legends." This moment, though, is where it all changed. And Amanda goes to the stadium, and I'm like, "Whew, we're good." You good, Amanda? You good? I'm good. And I said, "Are you good?" And she said, "I'm good." I said, "Will you tell me if you're not good?" She said, "Yes." Okay, I go to lunch with David. I sit down. I get a call. She has a question. She's like, I've never seen this software. Like, oh, I said, man, it'll be fine. When I get there, we'll be there in an hour or two, whatever. Like, it's gonna be fine. The software works. It's really simple. Doesn't matter. If you need me, you tell me. She said, okay, I will. I said, promise? Yes. Get off the phone. David goes, what'd you do wrong? I was like, I don't know. I thought I was pretty empathetic, told her really clearly to call me if anything's wrong. He said, call her back right now. This ends up being a pretty pillar. He wrote this whole story in the book because basically he's documented the whole day. He's videoing, taking photos, and I'm freaking like the F out and blowing it. And like, we're like, we don't know what's gonna happen. And then he goes, call her back and say this: on a scale of 1 to 5, how much would you appreciate me being there right right now? She goes, 5. I literally had this like, but I have it right now. Like, it was, it was like we dropped $5 on the table. We hadn't even got our waters yet. We ordered already. We're like, cancel everything, ordered an Uber, went to the stadium. And how I framed the question changed everything. And that moment for me was one of these like profound moments that you think you've been doing everything right right and I've been doing it all wrong. And I had no idea. And I really practiced it. I was— this is 5 years after doing leadership training, thinking I'm being good, I'm asking questions, I'm really invested in all these things and completely got the opposite answer. All she wanted me to do was be there. But she would never say it because she's a top performer. Top performers don't want to be needed. Like, and all these things, I'm like, oh shit. And David's like, exactly. And we walk in, team put our hands in, goes out. The most digital orders in a stadium section ever in the history in one night, first night. It is the future of how we interact. It is not downloading an app. It is talking. "Hey Siri, order me a beer." Like, this is what's happening. This is all going. The next day, email up to Tim Cook, CFO of Apple. You can go back to Q3, July last year. And ends up on the Apple earnings call. And it's like the biggest story ever. And actually, it was more for the Apple team. They were so proud. And it was like the biggest moment shift for them. And we all made it happen. And it ended up being a good thing. And the lesson— and it was so profound for me personally, but for everyone— that how you frame that question changes everything about the situation at hand. And having David, and also being a place where I was vulnerable enough to David to trust him so that he would speak up and say that. Most people, if you're not there, he wouldn't— I'm not gonna give you feedback on how to run your company, you're a CEO. Instead, we have a relationship where I'm seeking feedback all the time and I trust him at that level. And that's why he spoke up, which ultimately changed the entire day. And all of a sudden, being on the Apple earnings call when the CFO of Apple is like in the Philly stadium event, went off and telling that to Wall Street and like that allowed us to hire the head of Apple Pay, Anish, who's now our head of product. We made that moment and I'm poaching everybody. We sit across from Facebook and I'm like, don't you want to be on this side of the table? Like startup equity, you're already like too cashed out and that company's too big. And so that was always my recruiting strategy too. We recruited out the partners, but then it made the partnership better. You know, we still work with Apple all day. Apple team flies to London. We meet and like we We have that, that moment of that event that we all did together changed the trajectory of our company, me personally, and I think it started with feedback. It started with creating the environment and the vulnerability to allow someone to give it to me. Then doing it and changing my language with Amanda. She presented to the CIO of Aramark on that Monday. I've never been more proud. She gets done with this presentation. If I was to have done the deck, it wouldn't have— I don't even know how to build decks, first. Second, she gets done and the CIO, this is the big— and Ironmark's huge. He goes, "This is fantastic." And she delivered it with such confidence and calmness, because it all went off well. But had that switched and we not had those things and little things could have went wrong, that Monday is the meeting where like, Honestly, everything, we had to fucking cancel it and move it a week out. And we're not really, you know, we didn't make it work. And instead, it was the biggest moment. She walked out. I got her an Apple Watch for her. I got her an Apple Watch just to like thank her. And she starts crying. She's like, this is like the moment of my career.

And isn't it cool that thank you for that. It's an awesome story.

That was a long story. I'm sorry. The point is just ask how. Right. Ask how.

Couple of my mental notes are: ask Cal, move your ego out of the way, be willing to accept the feedback. Because I think we could all fall into that situation where David's saying, call her back and say this, and we can say, but, but see, but you don't understand, see, I can call her and say that, but there's all these reasons why we don't think that that will work. And just being able to trust David to say, I'm just gonna do what you're telling me to do and to see how it played out. You know, there's a question I wrote down that I really want to read because it's really important and it ties beautifully into this, I think. How do you manage ego when you want to be the best and feel like you have to be the smartest?

Hmm, lifelong struggle, right? I think that's kind of what we're all talking about though. Everyone has ego. I obviously have ego. I'm like driven to do something. And there's like a bigger purpose of why I'm here, why I, you know, selfishly like me speaking and getting feedback obviously makes me feel good. And the key I think that shifts is being aware about it and being open about it. And shifting to sharing and demonstrating openly is when you're able to then start saying, "I don't actually know that." Help me. Teach me. But I do know this. I'll show you. I really think this is like this, but I don't know it. And that's where you create the safety space where people can give that. But also, it really kind of, it changes the moment that you accept it. And most people are trying to look really smart. Once you stop trying to look really smart and and just do great work and be empathetic about it, all of a sudden people— you start opening up other people. Like our relationship is built off of the fact that that's how we started. That's why I'm here. That's why you were like, come do this, because like every time— because we're open together and that creates the safe space. That is really hard to do, especially if you don't have leadership that does that and provides that It seems amazing. I had a story earlier today from, I think it was Katherine with a K. Katherine with a K? No. Katherine Anderson. Sorry, you're awesome. How long have you been here?

With Alfred Williams?

Since 1983.

But you left for 6 years. You left for 6 years, right? I left for 6 years. And the fact that your story you were telling me That you came back says everything about the culture and I think what you've built here, which is incredible. And the fact that you let me come even speak here and talk about this stuff says already that you're intentional and trying to do this at your company. That's 98% better than anyone else out there because a lot of people aren't self-aware at the top and then it just stems down to everyone that through through every stage. And the fact that you came back obviously says a lot for what you already have here. And now it's just thinking about when personal life and work life are blending so much, how do we all be more open and vulnerable as a team, which will lead to more opportunities, more honesty, more feedback, which leads to all of us becoming better people. And that's the game here. It's not about work. It's like we're all here, half our life is here, and that's not worth not enjoying your job or not making me better so that I go home and like, you know what, today I practiced feedback, now I'm gonna practice it on you, Jocelyn. How can I be a better husband? You know, like, but it is overlapped, and I think once you start doing it and spending time with people who do it, that's the secret. You know, it's funny moving to Nashville. It's very Southern, which isn't bad, but it's very closed. I think men there are very closed. And I say the word therapy in Nashville and people think I like died. And it's like, are you alright? I'm like, no. What I'm saying is when I talk to people sometimes, coming from San Francisco, like everyone's, you got two therapists? Like I got two. Like San Francisco is so open. And it's like, we're all kind of just trying to be better. Why can't I talk about that? Why is there such a stigma? I'm in Peoria, Illinois. Literally, when I say it there, it's like, "Whoa." And then all my friends are like, "Man, I'm really struggling with life." I'm like, "Oh, you finally told me that. Like, have we tried to like figure it out? What are we struggling with? Have we talked about it?" And just being in an environment that is open to talk about things— and it won't start there. You're not gonna start with like, "Hey, you know, I've been doing all these things." But we made it a very open open initiative at a company exec level to offer mental health services as a core offering of the business. And once you start that, you're like, it was a bigger purpose too, because everyone's trying to design perks. And this is a rant, but everyone designed these perks, and after doing ping pong and cute office space and all this stuff, I'm like, that doesn't work for someone with a disability. That works for a bunch of dudes playing ping pong. Then you start to think about What is the perk that works for everyone? Giving them their time back. Making them more productive. I shouldn't decide what food to order to eat, actually. I should just make an environment that is designing perks that are one-to-one. I don't know what services you need. We'll fund all of it up to $1,000. Here's 1,000 resources of mental health services. I hope everyone gets the help they need on whatever they need. That's one-to-one, serves everyone, and it works for everyone. And once I started thinking about that, it actually changed a lot on how we thought about the company stuff. But going back to the vulnerability stuff, I think creating that space is hard. And it's, it's funny, I'll tell you like a really private story. I was talking to David, we were talking about therapy. In the military, therapy is a mental disorder. When you're filling out your thing, you have to say if you've been to therapy before. So you're filling out your application to go to the military, to go lead and shoot pretty big guns, and if you've ever done therapy, that is a something that they have to evaluate. Versus someone who took the time to really explore and improve themselves is now going to be in control of really big guns. And David's telling me this, and this is a podcast, and then I talked about I've been to therapy, and I'm like, you know, I was so stressed. Like, everything sounds great when I was— you know, it's so stressful in the high-growth industry. We were a little too early, we raised millions of dollars, and like all these things. And then you start working on yourself, whatever. And I did this, and my dad— I've been trying to get to open up for years. He's very closed. He's got 3 ex-wives. He's very insecure about it. You know, he's an awesome, awesome Awesome guy. All he wanted was a perfect, you know, all he wanted was to build a great marriage. And like, he had one with my mom for 25 years and whatever. I get an email from my father about a month ago because I opened up on that podcast and with David, and David's talking about it, the submarine captain, and we've made that a safe space to talk about these kind of things. I get an email and I would love to read it. And my dad said, hey, I just wanted to let you and and your brother know, for the last 2 months I started going to therapy and it's actually really changed my entire life. And I was holding so much in. And thanks for creating a place where I won't be like judged. And judgment is the killer of everything. And that is what we're all kind of like running away from. And so building that space where my my father then felt comfortable to tell me. That's what you get when you create that space. By you doing it and being open about it, whatever that vulnerability is, other people will start doing it too. And that is the secret. And then it's just this compounding flywheel. And then if people aren't self-aware, they have a huge ego, command and control leader, don't effin' work here. Like, that's it. This is what we're building and this is why we're building it and this is our intention. Intention, and I think building an intentional culture and life is important. So that's my rant. I don't even know. I don't mean— yeah, great. What is your name? Laura. Laura. Got it. I remember.

How do you go about navigating clients that may not be on that same level of vulnerability? Yeah. You know, that aren't necessarily somewhere or don't seem to be embracing feedback, or since we're in a sales or leadership role, how would we go about navigating that?

It's interesting. It's a hard one to do. This goes into active listening and some of the strategies around— this is something I want to talk about. I don't know how long we're here. One of the most interesting things about active listening is there's a quote, one of my favorite quotes about fundraising and raising money and business. And it's from Brad Feld, I believe, who was an investor in our first company, Gist. And he said, "Ask for money, get advice. Ask for advice, get money." The way to do it is actually to flip it so that they're coaching you. So use questions and curiosity that are showing your insecurities or things that you're nervous about and let them help solve it for you. So an example would be like, how can I help make this better for us? And if you start thinking about it, it's called like calibrated questions. And in active listening, it's a very specific way to ask questions that allows the other side to coach you and the situation, because then they feel in control. So not everyone's gonna get— I'm talking about a company internally. Everyone would be like, kumbaya, therapy, culture, vulnerability, that. I totally get it. You're working with like construction. My dad, he's at work. He grew up in command-and-control leadership. Do your job. Do what you're told. Because it's a— he was a steamfitter and it's industrialization. You gotta do the thing and plug it in. But now we're in a world we need people to think, not just do. And you want them to think, you need to ask them questions in the right way that allows them to be able to think. So the way to package this is think about it from putting them in control of the situation and being— they feel valued if they're teaching you something. So not like play dumb, but really situate the situation. How am I supposed to do that? Let them tell you. You say like, what are you trying to accomplish here? When they kind of get like, it goes off the rails and they're being a jerk and whatever, you're like, what are you trying to— go back to what we're trying to accomplish together. And reframing questions is calibrated questions that allow them to take that control is super powerful. Another one is— this is crazy that it works, but this is from the negotiation interviews— and the power in business or relationships of saying no, not saying yes. Everyone, if you hear like a leadership coach or sales, you know, you get like sales consultant people that are like, Yeah, rah rah, sales challenger aspect, woo! Challenger Chapter 7, I'm like, I can read a book. You know, like those kind of people. I have an allergic reaction to consultants. That moment is actually fascinating about no. And so what's interesting about the word no is it actually makes people feel safe. So if you want to get someone to say yes and get on your page at the end of it, get them to say no before anything else. So an example is this. If you said, if you said to a hotel person, you walk in, "Would it be crazy if I asked you for an upgrade or like an early check-in today?" No? You've disarmed them by actually the word "no." Gives you a sense of safety and control. That moment, then they're on your page. So it's very tactical, it's very unique, and it— but it can totally change by getting them to know that. And someone in a safe space tells you their secrets. You know the secrets, you close the deal. And that area is fascinating. You want to do it with your spouse. So if you said— if you said, you want to order DoorDash tonight? I love Papa John's. You're looking for yes. I don't really know.

You're about to solve like, what are we having for dinner tonight problem?

All done.

I'm really interested.

So, reframe the question. Are you against me ordering Papa John's tonight? No, that's fine, let's do it. No. It's things like that in psychology. And as long as you're not manipulative, you don't have an ulterior motive, or a different agenda, as long as you're authentic.

So he has it solved.

He has not solved—

you just ruined the whole dinner analogy because it's definitely manipulative.

Definitely— Well, you know, I would say manipulation and motivation are the same coin. It depends on your intent. Right? We're all in sales. We're all in persuasion. We're all in this thing, trying to figure out life. If my intent is, "I believe we can really do something great together," then that's motivation. If I'm trying to screw you, that's manipulation. But all these things all go back to what's your intent. If your intent is pure, it's fine. But Papa John's, like, you know—

You can just really not eat there.

Yeah. But that's an interesting— did that answer your questions?

Yeah. And I have a very real situation that happened yesterday that will really, really hit home the first point you made about asking the customer the question of, like, what do you suggest we do. And I failed. Hi, I'm Ted, and I failed yesterday on a phone call with an account manager and a customer, and I'll tell you why and how I could have done it differently. But ego and wanting to be smart gets in your way. So you're on the phone with a customer, there's a construction aspect to the project which we often deal with. It's modular casework, so it's part of the construction phase. They want us to punch that out and prior to installing loose furniture as we know it. And they're insistent that we put trim and tiles on the Etho nurse station during the construction phase. So we're all that are in healthcare related that understand why we're— that makes us nervous, right? So there's punch, and punch takes 2 to 5 weeks, and it creates all sorts of issues. So with the intention of being smart and bringing coming with a solution, we start talking about padding product. Well, padding product works sometimes, but if you use the padded product as a workbench, it still gets ultimately damaged, right? And everybody's had a piece of furniture used as a workbench. So what I could have done was said— and this is where ego gets in the way— because what if I ask them what they think I should do, then they're gonna— I'm afraid they're gonna respond respond and be like, "Well, you're the furniture guy, like why are you asking me?" So we don't ask the question, but maybe you're on to something.

Because another secret—

if I said though, "I have some ideas about how we've done this in the past. Is there anything that you think I'm missing?" Yes, I think you should pat it. Great idea. Don't have to own that you already know that that's a thing. What you might then suggest is say, how about we just talk real closely about when we put the tiles on and we try to put it a little bit, a little bit closer to move in. Not when HVAC has A-frame ladders over the top of workstations and we all freak out. FTS, my man.

Yeah.

Right. Like all that's very real, but I was afraid of thinking the moment to say it that way. Cause I'm afraid that there's going to be a response back to like, why didn't you know that?

And that's the right question. It's not binary. Your job is not to be smart. Your job is to make them feel smart in every interaction in life. And if you do that, everyone will love you. If we're all seeking— you know what I love in life? I love thank-yous. I'll take one thank you over 5,000 people who say you're an idiot. I don't know why. My ego?

I love it.

I feel— people say thanks, like, not everyone's like, "Oh, thanks." But like, but it comes from this kind of stuff. And that is really the secret there. And I want to go back because if this is a question of sales, and I think it's the most powerful one, it's like, well, they're not to that level yet, how do I really go? Another part of active listening, and active listening is funny when you say it. I remember someone told me like, do you do active listening? I'm like, yeah, listen all the time. And then you really get into it, you study psychology of language and really active listening and paying attention and how to frame and whatever. There's a ton, there's a ton of stuff in this. Another one for your specific situation, I think it goes into this, is Label their feelings. So, and the biggest way to know their feelings is nonverbal. Watch for the moment when you know that something triggered there, where they, that was the thing, and use the language that is, "It seems like," "It looks like," or "It sounds like." And if you label their feelings, that leads into also doing the calibrated questions. Those two superpowers usually can defuse any situation or big ego or I know what I'm doing. I know you know what you're doing. It seems like this— yeah, exactly that. Great.

Cool.

Let's go. And I think those are really powerful tools too. Because I mean, not everyone's nice and vulnerable and self-aware. You know what I mean? There's a lot of egos and I know and insecurity. It all comes from insecurity. So then if you know it all comes from insecurity, then just help them feel more confident. That's where it all comes from. Because the reality is the insecurity comes out as defense. And that is the thing. So when you don't really know what you're doing, that's why you're more insecure. And we're all in those situations. And being aware of that and helping them not feel that is a huge superpower that you can give them. I think that's a cool thing. And then in business, the thing we're looking for as Black Black Swans. The piece of information that changes everything. That's a Black Swan event. It's one of my favorite books on economics written by Nassim Taleb, and it's called The Black Swan. And it's why economists are terrible at predicting anything. Right? Because like, it's all unpredicted. And the reality is, the unknown unknowns are what change the world. You go in with the known unknowns and the knowns. You go in, "I think I know what they want." But the safe place and the feelings of that and making them feel confident and oversharing ends up with the black swan that, you know, the boss actually has something that they're really insecure about, that they actually have a connection at another competitor, and then this, and then you can make it about, oh, it's actually about your career move to make sure that this space is designed— whatever it is in your scenario, that's the black swan information. And the best way to get black swans is by creating creating the safe space and making them feel like they're smart, because then the more they feel smart, the more they talk. And the more they talk, the more you know. And the more you know, the more likelihood you have a piece of information that no one else has. And that is the secret to everything of sales in general, is like, how do you find the black swan? And knowing how to create the environment where unknown unknowns come out— that was like a Donald Rumsfeld quote. He said it In war and in real strategy, the unknown unknowns are when everything changes. But the minute you can get that information, everything changes for you too. And the way to do that is to create space that gives people safety. And all these kind of things around active listening are a way to do that, that might help you get over that kind of situation.

Who else has a question?

Kara, how are you?

Great, how are you?

I'm great, I'm in Charlotte, I'm just hanging out with my brother. Is there another Diet Coke? Oh, thank you. What is your question?

So like, out of all the things that you've learned from What was the hardest thing to implement in your life? Like the way you— Yeah.

Doing it for me personally. I really struggle taking care of myself. I, when I was running the company, I basically, you know, I moved to Nashville to really get healthy. I was 150 flights a year. I was, you know, an office in SF and New York, and I was doing the back and forth every day. Day, flying to Seattle for a T-Mobile meeting, flying here, Facebook. Like, I was going, and without having someone to be accountable to, or I'm just really bad at it. I love like taking care of others or always doing it for other people, but I never did it for myself. And really trying to do it for myself, be accountable to myself, you know, I need someone, I need a babysitter. So I hired a trainer, I moved to Nashville, and I paid this guy who, you know, like the Rift You know that guy who's 20 with the water jug? Like that guy? And I was 30. I gained— I was about 235 when I moved to Nashville. I'm like 205 now. I gained 40 pounds. And the arc of the 40 pounds is literally the arc of fundraising for our company. So stress, I'm not taking care of myself, alcohol at dinners. And whatever it was, I needed someone to be accountable to. And being aware of that myself and how to do that. So I said, here's the deal, I do messaging, I like messaging, I'm gonna pay you $100 a month. You're, you're 20 and you're ripped and you have a six-pack. First off, if you give me a six-pack, I'll give you a $1,000 bonus. So he's like, yeah! And he's like an artist in Nashville, he's like, a grand, let's go! I'm like, alright, let's go. Um, has he gotten paid yet? Obviously not. And the secret was, it took me a while to pay him back, but you know, The secret was, I said, and guess what, I've never had a six-pack and I don't think we're ever gonna get there. But I said, I want you to text me every single day. Give me a simple workout. I'm on the road all the time. Make it so I can work in a hotel. I'm trying to travel less. Just make sure you check in every day via text. I'm gonna give you $100 a month and a $1,000 bonus if you get me a six-pack. Every single day, this guy named Jason, he is, he doesn't even, this guy named Jason, I call him Jason Pushups. In my phone. And he— I mean, he texted me this morning, yo bro, and he's like such a bro, and he's like the coolest dude ever. He's— I think he's 20, I don't know how old he is. And every day, every day he texts me and he'll send me, you know, 20 sit-ups, 10 push-ups, 15 squats, how's your weight going, and he checks on me every day. And it's literally been— it changed everything. It's like I have someone to be accountable to. And that's just one example of I try to just get back to taking care of myself because I really neglected— and The Secret, obviously everyone knows, is like, it all starts with your health. And if you're not in good health, like, how can you make others in a company, etc.? And I just barreled through and like made it happen and like do it. But I think the company might have been in a whole different space had I been much better taking care of myself and taking my own advice on this. I I'm pretty vulnerable and self-aware and try to be more. But from a health perspective, physical health and mental health, and trying to meditate, man, I can't. My brain's like, blah, blah, blah. And I try hard for 3 minutes, and I'm like, ah! And then you do it, and you're calmer. And a calmer you makes a calmer company. Stress doesn't do anything. Like, stress makes terrible decisions. We all run around manically stressed. How do we change that? And so I think for me it's been a moment of focusing. And, you know, I'm lucky to have the time and the kind of this moment in my life to take a little break. And so it's been cool to do that, build new relationships, meet new people, industries I don't know anything about. I don't know anything about furniture, but like It's all the same. I don't really care about furniture, because I think business's purpose is to create a good place to work for people's lives. So it doesn't matter. It transcends all industries. So that's my hard thing. What's up? What's your name? Lauren? How are you? Lauren from Charlotte. I like Charlotte. It's a good city.

First off, you're a great speaker. I know you said earlier I'm not a good interviewer. You are. I've enjoyed it so far.

It's just, I think, whenever I think about things, it's like, If it comes from stories that have actually happened and it's true and it's authentic in anything, it's like, that's the point. So when I watch public speakers and they're kind of like the make-a-million-dollar success guy and he's just like never built a company or done— it's like, how do I take this guy serious? Or this lady? And so I don't know, I just try to be, you know, honest and open and share stories that happen because like it's all I have. It's kind of like the the past and trying to figure it out.

That's not my question.

Oh, what's your question? That was just a compliment. Alright, thank you.

My question is, what's next? Like, you've done so much, you have all these amazing accomplishments, but I would guess from your personality, you're thinking about next steps.

All over.

Can you share any of that?

I don't—

Because you've accomplished so much. Accomplished so much, it's like, okay, is that it?

No, I mean, I think when you start working with people who are always about ideas and the future and just building companies, it's, it's not like you're going after some goal. It's not some like wealth goal. It's not some like, if I did this, I'll change that. Honestly, to your question, I've been really focused on what do I do every day when I wake up and I'm like, I want to keep doing this for the rest of my life. How do I get there? And I'm closer than I was. I didn't feel that when I did companies, actually. I was like, this is so stressful. Once I can get this to here, I'll change myself. And I think it's the wrong philosophy, and I'm trying really hard to do that. For what's next, my promise to myself when I moved to Nashville was to make no decisions for a year. Because big decisions, whether I buy a house, whether I start another You know, you start a company and you raise millions of dollars, you're in it for 7 to 10 years or you're losing everyone's money. So that's a decade, right? So I'm kind of at this moment where I'm just like, what do I want to do that every day I feel like I want to keep doing this? And then that's how you build better companies, because you have a long-term view. You'll meet people that are like trying to flip it real quick. If I do this, I'll flip it. And like, why? I spent all this time. The worst part about selling is I missed was all the top performers leave. I spent all this time recruiting the most all-star team I've ever dreamed of recruiting, and now I don't get to hang out with Robert every day, who's one of my favorite humans in the world. Literally the smartest, most interesting, cool guy, and I don't get to sit next to him every day like I did for 7 years. So now I'm like, how do I build for the lifetime kind of view? Ask for me, If you do something for 11 years of your life and now you're more excited about it ever today than I was 11 years ago, making the world more curious is a cool mission. I would love to interview everyone in the world. I would love to democratize conversations so that everyone can do an interview. Coaching TED to host was actually a really cool— I think TED, you know, did an amazing job. Like, for real. And getting everyone to be more curious at a leadership level at a life level. Feels like a cool mission to go on. So, you know, Michael was my guy that I was paying, you know, a lot of money to produce our show. 3 years later, that the fact that I could give him half of Ask and make him my co-founder. We don't make any money yet. We don't really know how we will. If you have millions of people who listen to your stuff, we could go sell ads. We could do a coaching program. We could build software. We don't know yet. Right now we're on the like brand building of 11 years in. I couldn't be more excited than ever to interview everyone else in the world and really not about me. What shifted in Ask is it used to be Shane the interviewer. And now I wanna democratize conversations and be like TED for conversations where everyone can have a conversation. And so building that platform is something that I'm inspired by. I'm on, you know, different boards and I co-founded a company, like I'm just talking about things I'm proud of. Like I co-founded a company which is probably one of my most And this is like more of in the coaching type world of how it happened. The company's called Squared Away. And 3 years ago, 4 years ago, July, or March 2016, my assistant Michelle, who was in Hawaii, virtual assistant, I worked with her for 3 or 4 years. She's phenomenal. And she is a military spouse who's always moving around. And this company called Zirtual, they raised like $10 million, typical SF story like we had. They ended up going under, bad cash flow management. And Michelle calls me and my buddy Daniel, and she's like, like, the company went under, I don't have a job. And I'm like, look, I'm paying you, Michelle, you're my assistant, you now work directly, I'll help you start a company, whatever. A year later, I'm like, you know what, I was really— I was— it was when I was going through my, like, real allergic reaction to startup perks, that phase of my life. And I'm like, you know what, I want to give everyone in our company a personal assistant? Why do I get one as the executive, but the team doesn't get one? How much could I give back to everyone's life if everyone had a personal assistant? And first off, people are really bad at delegating and actually don't know how to use a personal assistant, because they're like, "That's my job. I'm supposed to do the work." And that's a whole different leadership philosophy of giving away control and empowering, whatever. So, I call Michelle and I'm like, "I actually am drunk." And I'm drunk in South by Southwest. Yeah, true. Alcohol and, you know, thinking definitely leads to some weird shit. So I'm in South by Southwest and I'm like, "Man, I want to give time back to everyone." And also, one assistant could be used between like 5 to 7 people. It's virtual. You don't need to be in the same office anymore, whatever. And I was like, "Michelle, do you have other military spouse friends?" And she's like, "Yeah, a lot of us." Because they always email me on my blog because I always talk about being I'm talking to a mom who is in Hawaii and there's no jobs and she goes and applies and they're like, "Oh, you're gonna move in a little bit, so we probably can't hire you." Also, remote work's exploding, contract work is exploding, etc. So I'm like, "Okay, I'll help you start a company. I don't know what it's gonna be called and I'm gonna be your first customer. Assist is gonna pay you. Get 3 or 4 friends and you're gonna be the assistants to us." And the key was I let people use it for their personal life too. Your life doesn't stop at work. So you want to plan the trip for this weekend, you want to book an Airbnb, you want to do all the work, you want to find a babysitter, you want to get someone to pick you up. And that was the secret to it. The bigger secret was the cheapest thing I ever did and the most valuable thing everyone loved. Because it was $150 per employee per month. Because one assistant for $700 a month could support 5 to 7 people. So all of a sudden this— and so I have this So I wrote a blog post about it. All my founder friends start emailing me. "Hey, what's this like superpower assistant hack?" And I'm like, "It's not really a thing." It's like Michelle and whatever. So I was like, "Michelle, call Robert." So Robert's like a genius brander guy. And his advice was like, "Go drink a bottle of wine, think about what you really do for people, and write down like 5 names." And she calls me and she's like, "Squared Away." I'm like, "Oh, that's a great name." 2 years later, my biggest like proud moment in life, Michelle, coaching her to be my assistant, is now CEO of Squared Away. We have 90 employees. There's over 140 customers. It grew 580% last year. Shit's chaos, don't leave me wrong. It's like everything's breaking everywhere because it's just going. And she's giving away control. We're hiring the team. We have 5 team on our core exec team now. Like coaching her and watching her go from my assistant, who, you know, you're probably making, you know, 30 to 40 to 50, 20 grand. I don't know how much you make to then becoming a CEO and then in under a year going from $50,000 in monthly recurring revenue to, or no, $5,000, like $50,000 a year to last month we did $1.5 million in ARR and she's just like, And she'll come to me now and say like, "I have such imposter syndrome. I don't have any idea what I'm doing." And I'm like, "We'll get it. We'll get there." And that's been like— I'm in the mode now like, "Can I invest and create a framework, whether it's with Ask, whether—" to create other CEOs. And if I can turn my assistant into a CEO, like that's a cool moment. And for me, it's one of the most proud. I mean, it's like 90 women. There's one dude named Dan. Dan's awesome. And like, it's, you know, we give the world their time back. And so it kind of, it all fits together. It's virtual. That's something that I've really enjoyed building. But maybe that's what I get to do next, is just be involved with companies, you know. I'm a co-founder of it, and you know, I own a good part of it. And it's been like something where I didn't really even see it, to be honest. It was like this little side thing that kind of happened, and now just working. That's a really hard thing, actually, to be a coach to someone in that scenario where she's just like, "I don't actually know," and work together and like evolve. Anyone can do it. Anyone can be a CEO. I believe that. Shane, I think we need to end our time, but this has been absolutely amazing. No, thank you all for having me. I'm around all day, all night. Are you coming to the banquet? Yeah, for sure. I'm looking for an award.

Please join me in thanking Shane Mac.