Shane Mac, a Silicon Valley transplant from his hometown of Pekin, Illinois, is a master of building authentic relationships based on trust and personal connection. In fact, he’s so good at winning people over with his honest Midwestern brand image, that he’s learned how to raise capital without ever asking for money.

I met Mac a few years ago at the Big Omaha conference in Omaha, Nebraska, and he’s consistently blown me away with his ability to grow funded companies ever since. He’s worked on the Gist and Zaarly teams, and he now runs Assist, a free-to-use travel and shopping chatbot for SMS and Facebook Messenger. This interview was recorded early last year, shortly after Mac closed a $5.5 million Series A round for Assist, which he achieved based on the strength of his professional relationships alone.

Mac believes relationships are the backbone of any business venture, and he’s a devoted practitioner of what he preaches. In our interview, he shares counterintuitive but proven strategies for creating authentic connections and gaining interest in your business. He believes in closing fundraising rounds by consciously refraining from making a direct ask. He also regales me with a too-crazy-to-be-made-up story of how he closed Assist’s $500,000 seed round in five days—over a holiday break.

If you like the wit and wisdom Mac shares in this interview, be sure to check out his podcast, ask., as well as his very unique and enlightening business book, Stop with the BS. Mac is very active on social media, so feel free to reach out to him on Twitter, Instagram and elsewhere @ShaneMac.

In this episode with Shane Mac, you’ll learn:

  • Why the best way to raise money is to avoid asking for it (7:05)
  • Step-by-step strategy for attracting investors, including one crazy success story (11:08)
  • How to build authentic business relationships based on trust (21:55)
  • Asking someone to tell their story is the best way to get them interested in you (32:24)
  • Why humility and gratitude are the keys to an outstanding pitch (40:56)
  • Actionable tips for making potential collaborators like you (50:06)

Please enjoy this conversation with Shane Mac!


This episode of Powderkeg is brought to you by DeveloperTown. If you’re a business leader trying to turn a great idea into a product with traction, this is for you.

DeveloperTown works with clients ranging from entrepreneurs to Fortune 100 companies who want to build and launch an app or digital product. They’re able to take the process they use with early stage companies to help big companies move like a startup.

So if you have an idea for a web or mobile app, or need help identifying the great ideas within your company, go to

If you like this episode, please subscribe and leave us a review on iTunes. You can also follow us on Soundcloud or Stitcher. We have an incredible lineup of interviews we’ll be releasing every Tuesday here on the Powderkeg Podcast.

Shane Mac Quotes from This Episode of Powderkeg:

Links and Resources Mentioned in this Episode:

Companies and Organizations:




The Kauffman Foundation



Geek Squad

Lonely Planet

Venture Capital Firms:


Binary Capital


Big Omaha


Stop with the BS

Software and Applications:







Shane Mac (@ShaneMac)

T.A. McCann (@tamccann)

Bo Fishback (@bowman)

Dennis Phelps (AngelList)

Ken Kamada (AngelList)

Galen Buckwalter (@jgbuckwalter)

Andrew Warner (@AndrewWarner)

Bryan Johnson (@bryan_johnson)

Jason Fried (@jasonfried)

Gary Vaynerchuk (@garyvee)

Robert Stephens (@rstephens)

Jonathan Teo (@jonteo)

Justin Caldbeck (@caldbeckj)

Daniel Houghton (@danielhoughton)

Sam Shank (@samshank)

Keyvon Beykpour (@kayvz)

Chase Jarvis (@chasejarvis)

Did you enjoy this conversation? Thank Shane on Twitter!

If you enjoyed this session and have 3 seconds to spare, let Shane Mac know via Twitter by clicking on the link below:

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For me, it’s how to build authentic business relationships based on trust.

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Episode Transcript

This week’s episode of Powderkeg is brought to you by our good friends at developer town. By leveraging their years of experience working with startups, developer town is able to help companies better understand the viability of potential software solutions, and quickly bring them to market. Developer town has created proven sprint to market processes. So large enterprises can move like a startup, you can find out more at developer Again, that’s developer Developer town, start something.

I look at life as solely based on relationships, and who you spend time with. And I optimize for it. And so like, that’s all I think about all day is like how to add value to someone that no one else is adding value to in that way, too. I never asked a marketer about marketing or sales and about sales, like you’ll learn, you’ll learn if you’re close enough with somebody by observing yeah, getting that close to them first.

That’s Shane, Mac, the founder and CEO of Assist, which is the platform that brings automated solutions to the world’s best brands like Charity Water, one 800, flowers and lonely planet. But what does that exactly mean? Assist is a free travel and shopping chatbot for SMS and Facebook Messenger. And you know what they’ve been doing chatbots since before they were cool. In fact, Shane and I recorded this interview at the assist offices in San Francisco, at a very interesting time in the company’s history, right after they closed a big round of funding in early 2016. Now, Shane is a unique CEO. And I love the fact that he and his company have had a lot of big wins to celebrate since the company’s founding. But one thing that they never celebrate is closing a round of funding. That’s distinctly unvalued. That said, few people build relationships and raise money as effectively as Shane. So in this conversation with Shane Mack, you’re going to learn about finding and utilizing mentors effectively. And you know, Shane has some incredible mentors that will talk about how to get people interested in investing in your company, tons of tips on fundraising, including why you shouldn’t ask for money when raising a round of funding. And we’re gonna get into so so much more. I’m your host, Matt Hunckler. And you’re listening to Episode 32 of powderkeg igniting startups, a show for entrepreneurs, leaders and innovators who are building remarkable tech companies in areas decidedly outside of Silicon Valley. And as I mentioned, assist is based in San Francisco. So you’re probably thinking, man, what gives that is in direct contradiction to what you just said the show is all about. But you know what the information in the show is too valuable not to share. Besides Shane is a Midwest guy hailing from Illinois, and we actually met in Omaha, Nebraska at a conference named Big Omaha. And I’ll tell you what, Shane’s approach to business has some very distinct Midwest flavor. That’s what I love about him. And it’s actually allowed him to thrive in Silicon Valley. So I wanted to share this story because Shane has just an incredible track record. And we caught him as I mentioned at a very interesting time. In addition to co founding assist, Shane is the founder of ask where he’s interviewed some of the world’s most influential people. He’s also an angel investor and the author of a book entitled, stop with the BS, which really captures Shane’s entire attitude around business. He helped build which sold to BlackBerry, he founded Hello there, which sold to k squared labs. He led, which has offices in Kansas City and San Francisco, and he built product at cobalt. We’ve known each other for years, and Shane just continues to build bigger and better companies and products. So we dive right into it in this conversation. Here’s Shane Mack All right, we are here fireside we’re here to sands fire, but we are here in the fire brother in your offices. It assists man. Dude, these are sick digs. Hey,

thank you. Welcome here.

Well, Shane, you are originally from the Midwest. You’ve already worked for some Midwest based companies. venture backed companies out of the Midwest. Kansas City. Right.

That’s Is that true? Isn’t bizarrely, Kansas City, wasn’t it? I don’t know. No one really knows what’s out there was best. I was always based in San Francisco. Of course, we had headquarters everywhere. Yeah, we’re in New York and wherever people want to see you or San

Francisco by way of Seattle. Right? That’s correct. Well, one of the things that’s that’s pretty cool. We grab drinks, just so people here know, we grab drinks together a couple of nights ago. And I think we talked maybe for three four hours about pitching the art of pitching the art of raising funding, which you just closed. I like to say

we did a series a and may go series ama so significant series i It was good. It was a good round from 12 investors Binary Capital led the round. And yeah, we’ve raised 5.5 million total cheers to you. I mean, we don’t really celebrate fundraising but our chairs just because

it’s I really love that you qualify that man because it is definitely a mile A song a milestone along the way, but not necessarily the end goal.

Yeah, I mean, that’s why you didn’t read about it right? Like we don’t. I’ve been there before, we’ve raised $15 million a rounds $80 million B rounds at the last company. And everyone internally got addicted to the press around fundraising as as if it was a success metric. So we just don’t celebrate it, we find core metrics that you can look at daily, that are human, that if it was one or a million you can feel good about. So we have people help per day and thank yous per day. And so you can look at it if it’s five, America, five, school people, and it keeps you motivated by the right things. And so we don’t talk about it. And the only, you know, this gets out, maybe someone write about it, but we are not like hiding it. It’s just not what we care about. It allows us to have a chance. And so I think you get there after you’ve done a couple and you’ve raised or watched your CEO raise rounds. And then you realize how much it doesn’t matter for the success of your company.

I think in some ways, it definitely matters, right? In terms of the being able to hit those hyper growth metrics and continue to grow, especially in something doesn’t matter if

you tell people about it. Yes.

Okay, great, good, Greg, I just want to qualify because people are watching this particular video, because they want to know how to do the fundraising part. So back to the business part, getting to the thank yous, getting to whatever metric they’re measuring that first year really matters, it definitely gives

you the shot. And to be honest, we didn’t really have it figured out. And we still don’t have it totally figured out. Like we’re just getting started. But we were able to keep our seed round, we haven’t even touched our series, and we’re still on our seed round. And so you know, being in Silicon Valley, people burn a lot of money really fast. And they raised more money, and have a different stance now, like we’re very frugal. We made the seed round last a long time. Yeah. And it was the only reason we got to do the eight rounds, because we didn’t need it. So it was very much like I love the investors, they are some of the best in consumer. And we were lucky to kind of both agree on where we’re going.

Well, you know, it’s interesting, because you just closed this round of funding. And you did it without asking for money. In fact, your perspective is you shouldn’t ask for money, which seems totally counterintuitive, right? So I want to make sure you have a chance to talk about that. Because I think it’s the counterintuitive things that usually have the biggest leverage for entrepreneurs, because not everyone’s doing them.

Yeah, I mean, I’m gonna go into my philosophy on how I think the easiest way to easy is the wrong word, because fundraising is really hard. But the best way to raise money, if you have the relationships built, is to not ask for the money.

Alright, so we’re definitely going to come back to the building relationships part because you’re, you’re very good at that piece. But yeah, walk us through the process.

So I just have these two things that I like to talk about, during fundraising. For most people, that is their first time. I think it’s one getting to watch two of the best co fundraisers I would say that are both my investors now, as well as and Who are those guys? Ta McCann, who’s the CEO of just now the CEO of it’s called life well, and then both fish back who was at the Kauffman Foundation. So he’s been on both sides of the table, his job is to give away $100 million a year. That’s all he did. And then he was the CEO of Zaarly. And so watching him do the whole fundraising process as well.

Both great guys. Yeah, they’re amazing.

And I think after watching them, I kind of took the best of both of them and molded into just what would work for me and kind of how I think about things. But what is really interesting of anything, like, if you go in asking for it, you want something more than they want you. And I believe I’ve kind of watched over time that it’s easier to raise more money than less interesting. Yeah, those are my two points that most people when I hear them first time founders say, I’m gonna go raise just a little bit to get started. And they say, the feedback and advice they get is just go ask as many people as you can for money. And I think it’s like ass backwards. Yeah,

it was so time to. Yeah.

And so what I say and what I did, and really, I’ve just always done in the last, you know, this is my first go around a CEO fundraising getting these rounds done. And it was really about how do you set out a timeline to fundraise if you have a product and team so if you don’t have those don’t ever fundraise. Because in technology, like people are like, I have an idea I would this is this doesn’t subscribe to any of those people. Yeah, if you have an idea, then go sit in your basement and get a paycheck for somewhere else and find a way to build it. If you’ve built it and you think you have something and you want to start fundraising. The way that I think about it is never go ask for money. I basically have angel investors and seed investors. Angels are people with checks five to $25,000. seed investors are people that write one to $400,000 checks, usually more funsies you have to ask their partner stuff like that. The goal is to get one of them to bite and lead the round. So what I do is the only thing I ever ask is I don’t meet people, and I send them my product. And I ask them for feedback. And then all I ever say is, can I keep you in the loop? The only question I ever

ask, how do you send them your product? Like, what’s my guest?

Do an intro? Yeah, through an intro, or the reality is, I was only able to go do what I did. Because we had a product, which was a testament to my co founder, as well as seven years of building relationships. Yeah. So for seven years, I’ve been just sending feedback on products and investments and being helpful. And I never had an ask at all. Yeah. And then I was able to have 85 meetings in the month of January for our seed round. And it closed at 22. Investors. Like that only happened, because seven years lead up to it. Yeah. So the reality is, if you don’t start there, then you don’t have anything. Yeah, that’s a whole different thing. You still had 85 meetings? Yeah, it was insane. I mean, but that’s kind of the way we operate is like it’s go time goat. Yeah. And but I go in, and I say, Can I keep you in the loop? And everyone says, Yes, obviously, there’s like, no risk, right. And then I have a really, really strict format. And I have a three month timeline. And for the first 90 days, or the for the first 45 days of the 90 days, all I’m doing every week is showing that we can make progress, we can ship and that more people are interested. So by them saying keep me in the loop, I add them to the interested list. Okay? And how often

are you sending those updates every week? Okay. And I particular day doesn’t matter doesn’t

matter. And I say high level, kind of what’s new progress? What’s shipped, how we think about the space, if anyone’s joined the team or interesting has happened. Always show progress, no matter what, can you keep moving forward and make the list of people interested grow? Because the only reason people really invest? Is because they see someone on that list that they actually want to invest with? It’s not like it’s about you. It’s about product. And then those are the checkmarks. Yeah, and then it’s who else is in this game?

So are you are you actually seeing everyone on the same email BC seeing

your GCC? Okay, at this point, you’re not wanting to mention, you know,

who you mentioned, see who else is on that? That list? So my guess is that you’re that’s just written out? That’s, that’s the written out part. Okay. I just wanted to clarify that that portion, because it seems like that could be a potentially backfire situation. I’m not saying MCC everybody on.

So you take that and you say, just keep, keep giving the update weekly. And you you’re not raising money right now, just make sure that you keep them interested in show progress. And the goal is to go find a seed fund that wants to lead the round, right? But if you get into like Game Theory, manipulation type shit, what happens here is on the angel side, you’re like, Listen, I have a ton of angels, and I’m probably raising in a month or so. Yeah. And you want to just get as many angels that are helpful, really, like they call it smart money, or, you know, money that sweats is what like people call it Yeah, the other side is, if you want to, like really be an A, this isn’t like human manipulation, but you tell them that you have enough angels. And you really don’t want to take seed money, because it comes with a lot of like baggage. Sure that comes with, you know, more partners, more opinions, more money, more leverage that they have. And you

say that without offending someone.

You just tell them, like you’re really interesting firm. And I have a bunch of angels, and I’m just gonna do angels and do a lower mountain. Any good investor wants to do more money than less, right? Once they make the decision of yes, I’m in on your company. They want to buy more of your company. Sure. So the reality is, more money to them is not Oh, my God, they’re giving me so much money. It’s they’re buying more of your company. Yeah, so that’s all valuation game. But the minute they want to do it, you can go from I’m just gonna raise like, 350 500, you know, to like they do 500 They’re like, Alright, we’re gonna raise mil and a half. Yeah. And that’s how you do it without offending anybody. You just talk through it, right? You’re like, I’m probably just gonna go Angel route. Keep it simple. Notes. explain your reasoning. And honestly, a lot of people do. And it’s not wrong to do and maybe that is your motive. Sure. But it’s a it’s a it’s a one strategy to get someone who you tell no to jump to want to do it. Because you’re not asking for their money. Right? The minute you do that. And you know, a guy Dennis Phelps, his was just more random luck for me. And I didn’t say any of that. He was just like, I fucking leadership now. And I was like, Alright, hold on, and he was like, 250 on my terms. 500 on your terms, or no, no. 500 and I was like, I don’t really need your money. I’ll just take the midterms. Yeah. And so then he was like, Alright, $250,000 I’ll lead the round. He’s the general partner at IVP which is one of the top four and all the valley and I was And he invested in Snapchat and Twitter be rounds, like big boy. And I was like, All right, sure. And then he was like, alright, well, you gotta get to more investors in the next five days. And on the round to get to 500k, or I won’t leave the round. Wow. Yeah, that’s true. That story is insane. Let’s talk me through it. So I’m at my mom’s house in Pekin, Illinois. Okay. And I have my iPhone five with me. Yeah, I don’t have anything else. And I’d met with

Dennis here in the city. Yeah, fundraising mode with fundraising.

Really, like I was in the beginning of like, oldest ticket down the road. So February is what I say Gotcha. Okay, I talked to ta a lot. He’s like it was from February. Think about that. And I never asked you to investigate. They’re just given the updates. And he finally said, like, I want to play and then invested 25 again. And I get this call from Dennis. And I’d had a meeting with them. And then I’m with my dad to December 26. Day after Christmas. The rules of fundraising are don’t fundraising holidays don’t fundraise in December. And also, if ventures available, take it. That’s like the key. Yeah. So Dennis calls me and he’s like, I’m outside this bar in Pekin, Illinois. So yeah, it said, you know, 250 on your terms, 500 on my terms. I was like, Dude, I’m not fundraising right now. And the problem is, that’s the truth. Because I don’t want to timebox anyone else and say, Hey, you have five days over Christmas to decide, right? That’s kind of bogus, right? So he’s like, alright, well, you know, I have 1000 companies. I want my money next year. And so I realized what he wanted was this 2013 tax incentive to invest. Okay. And basically, he’s like, alright, it sounds like shit, man. I’m like taking like an amazing investor who everyone would follow. Because the key is get somebody who everyone loves. And they the person gets someone that everyone wants to follow, because they missed all their investments. And everyone missed Snapchat and Twitter. Right. Right. And so you knew I knew that Dennis withdrawal everyone. I was like, my job’s done at that point,

right. It’s totally High School politics, right? Yeah. And

so he calls me and then I call back. And then the reality was, I didn’t have a company Corporation. I didn’t have a bank account. I had nothing. We didn’t start a debt. We didn’t build a product. We had a real product. It was in the App Store. People could download it. Sure. But we hadn’t made it a company. I was just kind of fucking around. And I was still exactly. So I had called Bo. And I said, here’s this situation. He was my boss. I see you. And I’ve been doing it for four years together. And I went to war. And I was like, here’s this scenario, and I’ll only leave if you’ll invest. And he’s like, on this. I think it’s a great idea. Go do it. And I think it’s like, I think it’s time for you to be your own CEO. And so I was like, shit, it’s like, Give me all that give me like the confidence be like, fuck it. I’m in. Yeah. So I called Dennis back. I’m like, What’s the deal? He’s like, I didn’t. I’m in Whistler Canada. I don’t, I can’t wire money over $200,000. So what I’m gonna do is I’m gonna send you a check. Overnight FedEx on Thursday, this Thursday, we have to know what Tuesday, I’m gonna send you a check for 10 or 50 grand. And he’s like, it’s quarter million dollars. And if you don’t get to 500 grand by Tuesday, and you can’t close the round this year, just rip up the chip. Wow, I was like, really? Like, fuck. So I call the attorney. I’m like, Hey, can we do a corporation backdated six months with founder shares, actually issue equity and stock so that we can get this real company by tomorrow. And he was like, that’s crazy. And I’m like, Well, okay, I didn’t ask you this crazy. Is it doable? He’s like, I mean, it’s gonna cost you I’m like, whatever, fuck it. Let’s do it. So we do that I call the bank and I’m like, hey, I need a bank account to wire half a million dollars to and the bank was like, no, no, we gotta go through like escrow and due diligence. And I was like, I call I’m gonna call Wells Fargo. They call and they were like, they were like, Hey, here’s a wire link. And it’s an escrow account, and we’ll figure it out. Like, alright, and I called up one other guy who wanted to invest kin who saved our ass, getting invested 200k With all his partners, and he didn’t get back to me till noon on Tuesday. Oh my gosh. So we had to close by 3pm, like, central time. And then I get one other guy emailed and I’d met him a couple of times, we always had to get coffee together. GALEN Buck Walter. And he’s a founder of eHarmony. And it’s just like the most thoughtful man ever. And I wrote him this email and said, interested question mark. And I wrote out like, Listen, this is completely ridiculous. And I’m probably timeboxing you. But I’m going to price the round. I’m going to issue equity. We’re not doing notes. I think it’s silly to do notes as well. It’s a whole different story. But we’re going to price the round, we’re going to issue stock. And if you are interested in this, like tax benefit that Dennis once, then oh, and working with me, then maybe we could do this and I need 50k And he writes back he’s like, can’t believe you thought of me. I’ve always wanted to work with you. That’s amazing. And we closed it on Tuesday. That’s great. That was the first 500k And then we did the wire man. And then we did a million No pun intended. We did a million more in January. So we did a $1.5 million seed round. That’s great. Yep. So part of that story is like, I needed dentists to bite right and I got lucky that he did. And then once he did, the rest of it was just sharing updates every single week showing progress. And then the email template is now Dennis is leading the round. Here’s the people interested. Yeah, let me know if anyone else is interested outside the group, and then you start getting it back like safety for me save under for me save it for me. And then the next week, boom, just let everyone know, probably about here’s why I’m so excited about these investors being involved. And you just continually tell your story of why other people are interested in you. And product progress.

Yeah. And team. So what happens? What happens when you have a week where you didn’t make the kind of progress you wanted to make? Because

always progress? Sure, that’s the truth. Okay. It doesn’t have to be that you shipped another product, right? It doesn’t have to be that you hired somebody new, it doesn’t have to be that a new asset investors interested or you land another client, it can be as much as you discovered something you never thought about in the market. You did research on competitors. And you think like, you have a better way to do it than that. I mean, there’s always progress. Yeah, that’s the only thing you could control and do share their share

the failures and the hurdles as well. And those updates.

Now I share once you have investors is very

different. That’s different than keeping people updated on the progress

totally. And like, here’s where we’re like, what are we doing? What have we done? What do we need help with? That’s TAS philosophy. And what do we need help with is very honest. It’s like we need this had to fire somebody you know, or we’re hurting hear we’re missing out. And so that’s very different than showing progress. Yep. And I think we’ve before you form a partnership and get investors, it’s about showing progress, and that you can ship and people are excited and just really showing momentum, then it’s about realities of like, you guys are partners now. And you have to like get this done, you should share what you’re weak at and how they can help and really get them on board. And the more honest you are, the more they want to help. And the more they trust you.

It seems to me that the equity you’re developing early on is just trust, for sure. And that’s something that I’ve seen you in particular, I mean, so we met at a conference in 2010. And I’ve stayed in touch ever since randomly running into each other on the streets of San Francisco or whatever city we might have. And every time I feel like not even that you’re trying to earn my trust, but I trust you more. One, because you’re honest and transparent about, you know, what are the hurdles right now, what are the challenges, but at the same time, you’re sharing the progress that you’ve made previously, whether that’s with your, your startup company or with your music. And so that’s one of the things that I think is probably your superpower, is in developing relationships that are founded on trust. Can you talk to me a little bit about your sort of philosophy on building genuine, deep relationships? Because you mentioned at the beginning of this, you’ve got to have the relationships before you even go down that path of raising money, or at least with your strategy?

Yeah, I mean, I don’t know if it’s because how it was raised your DNA or Midwestern gene, what it is exactly, but I’ve kind of you know, I think about it, a lot of why do some relationships turn out much better than others? Why are some very close and some aren’t. I definitely blur the line of professional and personal more than anybody else. I love first meetings when I meet people being the underdog. Like there’s a reason I wear flip flops and a jogger hat. It’s mostly just because I don’t want to be judged as like someone who’s important. Yeah. But then I spend all my time on two things really, which is, how do I ask personal really deep questions that make people uncomfortable? Like Andrew Warner really does that? Well,

yeah. And Andrew Warner Mixergy.

Yeah. Yeah. Like he’s become he’s one of our investors. He’s an amazing guy. And he he’s really good at, you know, I was at a dinner one time and he said, like, How’d you lose your virginity? Like, fuck, I don’t know, like. But he does say like that, right? He’s just kind of brings people together. But the other one really is, I’m always the one to take myself out. And I always share, like, the shit that sucks. And I feel like especially in this area, it’s like, everything’s great. Everything’s rosy. Yeah, I’m the one that gets people to talk about the things that aren’t rosy, the things that do suck the things that are bad, because I’m the one that shoot myself in the head first, right? Which is also a very good negotiation strategy. Because if you walk in, and you take out yourself on all this shit, you guys are doing bad. They can’t ask any fucking questions. Yeah, that you’ve already like, told him the truth, and they trust you more, because you’re fucking honest. So it’s all like a self perpetuating thing. Like if you’re just brutally honest of what you think you’re like, scared to share. You’re like, oh my god, like if I share? No, no, whenever you think, oh my god, if I share this, you fucking share it and you’ll be like, Wow, they’re fucking awesome. I say that. Now. They’re on my page, and they’re like me more.

Can you give me an example of when you’ve done that?

I mean, I do it in like every scenario I’m in so I don’t know, I feel like self deprecating is kind of just like my natural DNA and I just kind of like, but also an insane confidence that my mother gave me. So I’m like, but fuck we’re doing it. Every girl is just doing like fearless wicks mixed with that. How do you

balance that out that self deprecating, you gotta you know, you see, you gotta take yourself out before they even have a chance to because I always start here.

And then I go to the things that I’m really excited about, and the things that are really positive and how we’ve grown and where we’ve gotten to, in how do you motivate and get up, but he always had to start with being relatable. Right, right. And relatable is not superhuman? Yeah, relatable was like, Damn, he’s got a lot of problems, too. Yeah. So I just I think about that, like how to how to get on the same level with people in a way that draws them in versus you’re pushing yourself on them.

And so we talk a lot about the way you present yourself, how do you draw them in? How do you draw them out? As you’re developing relationships as you’re getting to know someone?

I stick to the personal side, I only do things when I know it’s in the vein that is on something personal they care about. An example would be Brian Johnson, the founder of Braintree. Yeah, he’s become a good friend of mine. That’s awesome. And the reason is because everyone probably goes to that guy and was talking about like world changing health ideas, because this fund is insane. He like only funds companies that are extending life form and shit

like crazy shit. Yeah. Yeah, nice. But everyone goes

to him like asking for advice, money, shit. Like, and he just gotten divorced. And I was like, scattered. I just wanted to like, meet new people go have fun. Like, let’s walk around the city. Where should we go? And like, let’s just talk about dating. Yeah. And all we did for a day is walking on this fucking town, had some drinks, and got deep as hell on dating, on relationships on why it’s hard on why it’s why aren’t we settled down? Why do people get divorced? And you tear down someone in the divorce realm? And really go deep there with them? Yeah, like, that was the trust bond. Once we had that, then we got into a lot of other things. And you know, we don’t work together, isn’t it about He’s just a friend. But we’ve gotten to where, like, you know, now all we text about his dating.

Yeah, it’s great. That’s awesome. What and you said, you said the word tear tear down, which is not your intent with people. It’s to get to the core of someone’s pain point. Right. Like when when you’re getting to know someone and understand their pain point, or does break down the barrier? Yeah, absolutely. Tear down the barrier. Find out really what makes someone tick. And I think that the thing that you do really well is and I’ve experienced this, just myself, I’m trying to think of some examples, all the times that I like, manipulated, you know that not even I’m kidding, not even manipulating what you probably did to not rescue or anything, no, but like when you when you when you, when you’re able to tear down that wall, you can find out how you can actually help someone for sure. Because if you just go to someone and say, Hey, how can I help you say, No, I’m fine. I’m good, right? Like that’s, that’s a natural response. Yeah.

Well, what if I knew that you liked kite surfing? The next time I went, I would invite you, right? And so I have a list and I literally have context on everyone in my life and what they like how I met them and who else they know that like the same shit.

Yeah. How do you track all that? Well, usually is just but now I just use a CRM. Okay, what CRM is streak streak. Yeah. All right. Just met the founder of streak at a well, not the founder, one of the one of the guys that streak,

Brandon, I mean, streak mixed with insane tagging in my address book. Yeah. Like, I’m Mike, my address book is name. Talent. Yeah. Like, what skill set do they have, I have them all coded. So it’s code marketer developer like, and then how we met. And then I write all these like tags on things I remember about each person, but I have tags across everyone. So I can then search surf, and have 20 people show up, right? I can search a bar and have 10 people show up and it’s like, I go to the bar too much. But it’s like that kind of matrix of tagging that I’m obsessed with. That’s what we’re obsessed with just is like how do you add context to all your relationships when you have too many relationships? Sure. And it gets hard.

Well, but if you have a system and you make it a habit Yeah, of of categorizing each one

yeah, that habit of then also an hour of day spending following up with them. Yeah. Like it’s work and talk to me about the follow

up and the in the actual process that you have. I guess I would call it more of like the habit that you’ve developed.

This is all I mean, this is how just worked Yeah. And watching him be obsessed with relationships. Yeah, in a way where he’s not like, he’s all different. He’s like IQ and I’m like, EQ Yeah, I mean, he’s genius EQ too, but like, he does it in like a military. I’m a professional athlete. I gotta spend an hour a day following people. I do it in like, emotional intelligence. How can Do something to be helpful that starts a conversation where we kind of then get deeper and have a more interesting kind of, you know, talk and then we trust each other more.

Yeah. And when you’re doing that are, are you in the back of your mind thinking maybe someday this guy or girl could be XYZ in my life? Or are you purely just saying how can I just deepen this relationship at this moment?

I mean, both right? I think at all times, everyone’s like, in our world, everyone’s optimizing for something. Sure, right? I’m optimizing for the type of people you want to be around and spend time with because they have similar interests are way different interests, but their motivation is the same. They have the same ambitions, they really want to go get shit done. And, you know, they look they believe in their family, they spend a lot of time just they’re good people. Yeah, but the list is a list that I have, which is who at what time in the future? Could I do something with whether it’s work, whether it’s play, whether it’s just have a conversation? And if it’s none, then why the fuck are you talking? Really? Right? Yeah. And so you’re kind of like, you’re kind of defaulting to that when you meet some of the first time of like, Is it someone you want to spend time with, again? Why, if it’s somebody want to work with again, then you know, I definitely spend more time on that list. Because you never know when timing is gonna happen when you go start a new company. And for someone else that you’ve met, that you think would be amazing to start a company with, to have the same break of time to be able to start a company with you and not have something else going on another company. Another thing is very low variance. So the bigger that list is, the better. Yeah. And so that list for me is huge. And I have been building it for 789 years. And like, I spend a ton of time making sure that I’m always staying in contact and being relevant with that list.

What do you what do you say to someone who who hasn’t been doing that? You know, maybe they connect with someone with link, you know, on LinkedIn afterwards? Maybe they throw a business card into a shoebox, which may or may not find their way to their to their CRM, but maybe the tagging doesn’t happen. What do you say to that person? Now?

Don’t do that. You know, I didn’t even know what I was doing at the time. And it turned out to be the most powerful thing I did, which is when I got into not asking. But it’s totally ironic, because I started to ask. So when I started ask, can you give us

a 32nd pitch on the ask ask interviews,

has turned into something a lot bigger start by asking, but we help design products and experiences that help people learn by asking the right questions. Ask interview series is me just asking one personal question to someone that leads to a conversation. And I email people. And so one key learning is I was doing this when I was 20. Yeah. And I remember my first interviews, they were just like, horrible. But I was just, I had a content platform. And I had a channel and I had something that I could ask someone to join and tell their story, not mine. And everyone does. Everyone in this industry has an ego. And they want to tell their story. Whether or not you’re big or not. Who the fuck knows. So I just started asking. Yeah, and everyone kept saying yes. And then the minute I got like, people in our industry, it was like Jason freed did it and then Gary Vee, did it. And then the head of the fucking Navy joined. And I was like, I just kept asking people to join. And then Robert Stevens who now works with me, I met him because asked, but when you have a reason ask somebody to tell their story on a platform, whatever it is, like, there’s so many ideas around this. I think like, what tools do you use would be really fascinating. So I’m gonna build that blog. So I can just see like the list of tools that everyone uses. Yeah. What is your story? What is your personal life? Whatever it is, to let someone else tell their story. Yeah, is the single greatest way to get someone to say yes, it’s what you do to me right now. Like, it’s this you’re doing it

that’s like some judo, Judo shit, right? It’s

but you know, people will say yes, ception that you might not other have had access to. It’s the reason you do it. You get to learn. But you get to really connect. If you emailed me again, or text me, I would always respond now. Right? Yeah, we’re on a different level. And I didn’t realize I was doing it at the time at all. Sure. I was just like getting into it. I was like, man, every time I get off an interview, I don’t like it’s so different than what I thought about the world, like, Fuck everything. Ridiculous. And then I was like, Shit, I’m getting yeses from everybody. Or it took me like six months and I got the process down. And then I was like, Alright, how do you really make this into something where from there to follow ups to getting personal to adding value to never asking them for anything, right? Always staying in touch, could build out a network where you can actually create friendships and bonds and trust and then work together with people or just become friends with people. I’ve never started by like wanting something from them. Because if you walk in the door with a question, needing advice, you’re always perceived as it’s not levels, but they have a perception of you and you have a perception of them. Yeah, so obviously never be a fan. And so that’s kind of the way that I think about it. And the way that it’s kind of happened. And now like, I’ll never, I go to the people that I’ve worked with or node ask for, like advice or mentorship, but that’s never who I go to in the public. You’ll never see me do an AMA, right? Like, I just don’t do them like I don’t as a contributor, or as a asker. I’m not the one that’s like, how do I do marketing? Like, fuck, fucking cares. Go in the back room with someone you trust that actually teach you? Yeah, go work for someone that does a great marketing. And so I never think about it and a person I don’t know, I want to go seek knowledge from Yeah, I think it’s the biggest fail. It’s the biggest failed conferences, it’s the biggest fail in networking. Like, I hate the word networking. It’s so terrible. And you see a line to go ask someone a question. Absolutely. And really half time, I just want to pitch their shit. And that person’s gonna fucking remember, like, didn’t even know you and you have 100 other people. And so I think it’s the largest fails when people do that.

And so instead, you’re encouraging people to ask what kind of question?

No, that’s a good way to do things that let that person tell their story. Yep. And not be the one seeking advice. Yeah. advice should come, in my opinion in a back room with someone you’ve trusted or worked with for a while that can really help you. Or if you can’t get it, and you don’t have those relationships, you should go work for a person you want to be.

Yeah, was it? That’s great advice. Thanks.

I think the single worst advice in the world has worked for a job title. And the single best advice that colleges don’t tell you is pick five people in the world you would want to be and do anything in the world to work for them. Because people change the trajectory of careers, not titles ever. Yeah, titles are bullshit across all you need them in structure. I completely believe that in corporations and companies, you need titles that you can put on your resume. But to be a director of product and a director of product at three different companies means nothing. Yeah, right. And so titles become kind of just worthless. There’s no accreditation to a title. There’s accreditation to Stanford and Western Illinois, where I went like, are the folks Western like you went to Stanford these better? Like, that’s how it works. Yeah, not in job titles. And so you get out and you have this thing, and you still be proving yourself. But when you find someone like I got really lucky to find TA and like, he took my direct trajectory from here to here. And that was it. I was like fuck with, like, I don’t know what my title was. But working for him has been the single greatest trajectory change in my life. Yeah, absolutely. And I think that’s kind of something that no one talks about.

Well, and you mentioned, you mentioned the difficulty. I

think I got so off track. No,

I think we’re 100% on track, because this is your superpower that you’re developing. And I think that dissecting it and helping entrepreneurs understand that relationships are important. And it’s a discipline for them to do and that before raising a round of funding. You know, maybe they don’t have seven years to do this. But if they have seven months before they think they’re going to start raising around, they should start today. Ya know, start by doing the right things today, and you’re only going to get better. I do like the fact that ta treats the relationship aspect, almost like a professional athlete.

It is me that’s how I become Yeah. Because it’s it’s hard sometimes to think about the process of looking through all your contacts in it. There’s news about them seeing if there’s stuff to follow up on see if there’s things you remember, like Oh, shit, getting up getting all your follow ups back. I mean, my inbox every day has 25 follow ups. Because I like I’m obsessed with following up. Sure. And I think it’s the single greatest thing you can do people who don’t follow up to like the hated saying, and that alone takes hours.

Yeah, but it doesn’t feel like work. Do you schedule it?

I used to but now I just do it just to get to know wake up and it’s first thing to forget

about so you had to schedule it until you develop the habit. Yeah. And now it’s it’s just part

of it didn’t feel like work, right? Never did. I was like, yeah, like it’s someone looking at me. And she’s like, No, dude, that’s work. He’s like, this will pay off. This is the core of everything you’ll do. What is life depend on to make decisions? I was like, I don’t know. It’s like people to everything in your life will be determined by what someone else says yes or no to deals, hiring decisions, product trusting you, when they join your team, they start to work for you. I was like, he’s like, he’s like whether or not they work for you or you work for them or they fund you or they trust you or you burn a bridge. He’s like to people decisions. It’s all the whole life. And he’s like, so spent talking to him on it.

Thanks for listening to powderkeg igniting startups. I wanted to take a minute to make sure you know that this episode is powered by verge in network of local communities with global reach for tech entrepreneurs, investors and top talent outside of Silicon Valley verge has hosted more than 1000 entrepreneurs to pitch their companies at our events around the world. Those founders have gone on to raise more than $500 million in capital collectively, and are disrupting industries creating wealth and changing the world. And if you haven’t subscribed to powderkeg yet, it’s not too late. You can subscribe wherever you listen to your podcasts or on SoundCloud, Stitcher overcast iTunes, Google play all the major outlets, and you can find all the links to subscribe as well as show notes and transcripts at our website So that’s powderkeg all one If you have an iTunes account, we’ve created a handy link for you just go to That’s going to take you directly to our show where you can subscribe, leave a review and see all the incredible episodes from past guests, including Brian Clark at Rainmaker, based in Boulder, Colorado, Karen Norman, at upfront ventures in Los Angeles, California, and Max Yoder at lessonly. In Indianapolis, Indiana, it’s your subscribes and reviews that help us reach more people and share these founders stories from beyond Silicon Valley. So again, that’s back to the show. So when you’re I’m gonna bring it back to the the raising funding partner, and I want to make sure that we’re keep an eye on time here. But the way that you quote unquote pitch is it’s not a traditional pitch, you’re not in there, you know, going to 85 people with a deck in hand and saying the same thing at every single piece. Is that right? Not a lot. Yeah.

Not a lot of actually raised at the deck. Okay, I didn’t have a deck. Yeah, I let them play with their product beforehand. And they got it, like photos of interview. That was kind of the the it was a really easy, I think simplicity of pitch is critical. Because they just grasp it, boom, done. And by the time we got on the phone, I think the best way is to tell us to tell the story of how long you’ve been doing it. Because if people forget that the moment you’re showing the product, no one else knows you’ve done it for nine months, right? They’re like, Oh, you just built this in a day. It’s great. Tell me the story of how you discovered this. And having the moment usually three months before that day of when you figured something out. One thing that was so big and different. You’re like, holy shit, this works in every city in the world you upset 100 I remember saying that a fucking 100 times. That was the light. Yeah, because we figured out how to mind every Instagram photo in the world to be a better rating system than Yelp. Okay, that’s crazy. And it wasn’t possible three years ago, the photo didn’t exist three years ago. And yelps only in 100 cities and it’s a $5 billion company. ridiculous statement. We’re like two guys with an app. Right? But that moment is what everyone could grasp. It was simple. And it was like we just did this and we kind of hack this and we had a V one thing we threw it out and you kind of like show a failure story. The discovery story and the fucking Oh shit. And the OSHA is the most where it’s gonna be so dialed so simple. That’s the only thing I repeated. Yeah, I was like, dude, photos of the new view. Holy shit. Why the fuck would I go to Yelp? There’s so many like negative people just screaming negative shit. Photos are always positive. And people say they like it. This is the better fucking reading and it works everywhere in the world. And like, you’re like Fuck Yeah, fuck shit knew. I was amazing. And like, but that is the that flow in the come that come up. Let me see all excited. Let us yeah, like I was like, it was fucking real. I was like, fuck, I mean, I do believe it. And the thing that helped us out a ton, was it was the holidays. And everyone was traveling. Yeah. And it really fucking worked everywhere in the world. So investors were like, dude, I’m in Seoul, South Korea. And it works. I’m like, no shade fucker. I told you, you know, like I wanna and, you know, it was like, we were lucky. It was actually a really interesting, like, everyone was in Paris and London. And they’re like, dude, I’m like, Yeah, to be built it.

Man, it’s awesome. I think there’s some nuance. I think there’s some nuance the way that you position that, too, in that you let people come to their own conclusion about it, as opposed to telling them, we’re going to be the next Yelp. You didn’t say those words. Yeah. You said Yelp is in Yelp is in every city. And we’re we’re a better rating system. And you said up much more eloquently than I just

did you know, you don’t like Garth Brooks is the best performer in the world. Why is that? Because after every song he acts surprised, he always acts surprised that everyone still loves his songs. The key to the moment when you let them like digest it is for you were just so surprised that it was that big, it actually worked. You couldn’t believe it. Not being able to be like, I couldn’t fucking believe it worked everywhere. That that mentality is so powerful of a human emotion to show gratitude and surprise that no one thinks about and I’m a I’m a musician, so I do it on stage all the time where like, should I believe no one showed up like that. That is if you go to a Garth Brooks show. He’s just one of the single best performers in the world. He’s the most highest grossing musician I think ever. I’m not a country fan, but I’m gonna go to one now. He’s incredible. Yeah, and after every song, he’ll stand there, always sold out. And he’s just like, it’ll draw it out forever. And it’s like gratitude with like, I can’t believe this is real. That emotion takes wins. Yeah, no one hates him. And it’s the single most powerful emotion to draw people in. Because I didn’t say like, we’re better than Yelp. That’s ego, right? I said, I can’t believe you also in 100 cities, it works everywhere. That emotion is huge. That’s relatable. And that’s like, no, that’s like real deep psychology shit. But that’s emotions that when it’s real, you can tell, you can tell that like, I wasn’t bullshitting you there, because I got excited about like, literally, we built this shit, and it works in focus on South Korea. We’re like, wow. So it but I think it’s one of the most powerful things. Absolutely. That no one talks about that’s like, never talked about of that they go in with, like, tell them you’re most confident, and I never do that. You can feel my confidence. But I’m never saying my words of like, I’m the best, we’re gonna win. They suck. I don’t take anybody else out. It’s just draw.

And at the same time, you’re taking yourself out? Totally. Along the way. Exactly. That’s great. So what what was the number one thing that surprised you about raising this last round of funding for you when you’re out, quote, unquote, pitching, which wasn’t actually pitching because you weren’t asking? The eighth round?

Yep. I mean, our eighth round was for having nothing like we were just getting started. And connecting so instantly with the lead investor, Jonathan, who also was Snapchat, Tinder, Instagram, like the dude is just like clockwork. We closed in eight days. We did most of the negotiation through a group text message. Me and Jonathan and Justin, the other partner, all through mostly text, that’s great texts and screenshots. I’d like screenshot stuff on my lawyer and ask a question. And we ended up with great terms for both sides. And I was so surprised that we could go from we met, I introduced to my team, and we met again. And we signed a term sheet in a this was a Thursday, and we signed on a Friday.

And what’s the number one thing that you attribute that to?

Who I got the intro from? And two things. One is luck, because every investor right now has messaging on their, on their, like, I need to invest in a messaging company. Sure. So I feel like every a investors like shit, there’s this one, there’s this one, there’s this one, I need one, they already got a rounds. So in that, in that thing, I would imagine that Binary Capital who’s a round lead, already had this, like, we need to find a messaging company. And so because we hit it off, we were already in there. Like, we need this. So that’s the key is like, if you don’t get in there, then you’re fucked. Anyways, that’s where it sucks is like it could be amazing. You hit it off, and they draw you along. I also didn’t need a law. Yeah, had 1.1 millstone in the bank. And I was able to just sell the team. Yeah. All that talked about was the team that I’ve worked with before.

Right. And which is built relationships.

Yeah. And the space. Yeah, it’s all my ex people that I’ve worked with the last companies, and the space in which we get excited about him. And the product was really good. The demo was great. And like it worked really well, etc. But I think it was they had it on the roadmap. Yeah. And Brian Johnson injured me. So Brian Johnson. So I also think about this is, I think the strongest way to network is to be thought of as the, for me, my personality is to be the person who makes people have fun. Yeah. Because then when they have fun in the future, they’ll invite me, which is how you get closer to people. Right? And when they have fun, they’ll think of me. So Brian Johnson flew here with with, flew here and came to my concert. My last show. That’s awesome. He then goes to Necker. He’s in Necker Island, him Branson and Jonathan are the investor. Yeah, a party and he’s like you would love Shane calls me FaceTime from Necker with them. like, Yo, you gotta meet Jonathan. Then I’m like, well introduce us. I get a three way text from Brian, Jonathan me. And that’s what led to our first meeting. And that’s what it pulls here. And I think Jonathan really respects Brian because Brian has just sold Brian G for like, $650 million dollars like, he saw that tree. And how I met Brian was the Robert Stevens, who I interviewed for ask. And it all goes back to just I asked to interview for ask on Twitter.

Really the Twitter approach

Twitter is this is the reason I you could tie the a round back to a tweet from 2010. That’s Robert Stevens. Can I interview you about Geek Squad to be on? The Ask interview show? He came on? And now he’s our CEO. Now he works with me.

That’s awesome. Because of a tweet. Well, Congrats man on all the progress so far. I’m not gonna say too much congrats because I know that raising the round isn’t everything but congrats on building the product building awesome team. Really, thank you so much for taking the time to To tell the story, I think that we could talk about this forever, man like I, especially the aspect around the psychology of making instead of you wanting to be connected with someone else, the psychology that we’ve talked about is sort of that, like that inception of you getting them to want you. I mean,

this is this is the there’s keeping up with relationships. And once you meet someone, and who the intro was or the environment, I mean, I’m huge on like playing music, right? Yeah. So you don’t ever play a show? If you’re going to have 50 people, you do it in a 30 person menu? Yeah. Right. The last one was 450 people, we did three numbers and vignettes. Right, because you never want to, you know, have a thing where it looks like no one wanted to be that demand

should always outpace supply. Yeah. And so

when you first meet someone in the how to manufacture intros, this is what I’m also obsessed with. And so I don’t know that you want me to tell the Daniel straight? So the best one that I’ve done recently, and I’ll caveat this with, you should not do this if you have malicious intent, right? This is I don’t know somebody. I think that if we knew each other, and our companies had something aligned, there’s something we could do in the future. Yeah. Well, what I’m not going to do is walk in the door and say, I think there’s nothing we can do in the future. Or check out my company, right. So I went, we’re in the travel space. So I went to the number one travel conference. And I was like, I made friends with the person who was running the conference. And she let me just sit backstage. Yeah, so I’m at the conference gift. And every 15 minutes, a new CEO is ready to go on stage. I’m just sitting there talking to him bullshit, mostly about my tattoo with Daniel. He’s the CEO of Lonely Planet. Sam shank was there with hotel tonight. I knew he invested in Kayvon. So I was Periscoping. And then I got him to ask him about Periscope. So then we’re talking about Periscope never even followed up, followed up with him same as our investor in a round. And like that one just happened. I stayed in touch with Sam but that’s how it happened. Then Daniel, I was like lonely planets. Fascinating. They’re a book company that wants to become a tech company. I think we’re kind of building this people are more like guidebooks. He’s a fucking guidebook. I don’t know what we’re gonna do in the future. But it seems like there’s something here where he has this global brand is a new CEO. He was young that like, I would like to know him how to be a better CEO. How is he running this 500 person company? As a 28 year old? I was like, This is crazy. So he goes on stage comes off we talk about he asked me what my tattoo because I like crossed paths with them. Right? It’s like I set myself to cross paths with them. I didn’t say they want to speech. I just act like I knew nothing about them. Yeah. And I then he was talking about his wife’s tattoo. And so we talked about violin and cello and stuff. Yeah. How to say if I’m ever in Nashville, you know, I’ll let you know. It’s a cool. So I then proceeded to email Daniel, like three months later, right afterwards as a great way to you know, if I’m in Nashville, three months later, last December, I said, Hey, Daniel, I think I’m gonna be in Nashville, January 21. To the 24th. Wednesday through Saturday,

how far ahead is ham? Was this like a month, kind of weeks? And then

he’s like, dude, if you’re here on Thursday, it’s a great cocktail was like, great. That’s all it said. There was no ask was one sentence in an email. He’s like, Yeah, never respond to random request. You know, like, but I remember this guy. We talked about techy. So I booked my ticket after the email. For three weeks I research everything about Daniel. Yeah, I research. Lonely Planet is a company how this younger guy got put in a CEO who the new owner is, but I’d went deeper. And I was like, I went to see who the first person you ever followed on Twitter was? It was Chase Jarvis. Yeah. It was one of my investors. And like a friend of mine, he’s been to ask, and he’s just a mentor. He’s awesome. Seattle routes. Yeah. So then I looked deeper. Daniel used to work in Seattle Times as a photographer. I’m like, Alright, photo journalist. I told Chase. I’m like, do you know Daniel? He’s like, I don’t think so. And then it’s like, look them up. So Daniel had applied for chases course in 2009. And he didn’t get it. So I’m like, it loves Chase. Yeah, he loves photography. He’s a CEO who just had a fire 100 people. So he’s in the space. And we’re gonna go have cocktails. So I go into this meeting. And the way I do is, if at the end of it, I think we’re going to be better connected. I’ll do this. Yeah. But I also have an intention to tell them that I did this to him in the future, which I have told Daniel, right. So I go to this meeting, acting like I know nothing about Dana and I walk into Lonely Planet and I fly to Nashville. I go there, we’re just hanging out. And he’s like, Let’s go have a cocktail. We’ve got a cocktail. And so I broke out 15 minute blocks of time for two hours.

Where were you hanging out before the cocktails at the other office at their office

headquarters? Yeah. And we go upstairs a suite bar, and we sit down having cocktails at the bar. And I knew that if I started talking about snowboarding, that he would start talking about a snowboarding film company he bought, which would have led me to talk about the fact that I know Chase because I have a friend that does video shit to me. So I set this up and the whole point of that is instantly he has more interested in me than I have in Him. And so he I started snowboarding. He’s like, man, dude, I just bought this company. Let me play like we bought this freakin video company Check this shit out. So he shows me this action film on his phone. I’m like, dude, one of my fucking like best boys and one of my investors that our company does shit like this all over the place. And he’s like, Who’s that? And I was like, it’s kind of Chase Jarvis. And he was like, you know, Chase Jarvis. And I was like, yeah, so I had chase that so I text Chase and chase rides back and was only playing it and I was like, Yeah, great. pre planned. So then, was this pre planned? No, maybe? I think so. Yeah, I had it all pre planned. Even the demo was pre planned. So then the next hour, I just dug deep. I was like, man, I was like, we just had to lay off 45 people at my last company like that was the fucking worst started talking about and then he got deep and then we went really deep into like, how shitty it is delete people off and like, how much planning to do and how it sucks and like, he’s like, I just started crying. When I got on a plane after I was done. I was like, fuck me to like, all this shit. As got to a place where then we have this fucking bond. Yep, hour and a half later. We’re like three whiskies in his head. What the fuck do you do? I was like, Oh, we just have this like an app. We think guides or you know, people are there to guide books. Yeah, I was like, hey, it’s called assist. He does it. He just messages this thing. instantly connected with a local, it’s a beautiful card. He realizes we’ve integrated all these API’s you can book lifts, order reservations, book, a hotel, all within a chat. Yeah, someone’s giving them like a real personal local experience, which is everybody

search for initially, when when he got to a sushi date

with him in his wife in San Francisco. And so it keeps going, he’s going then you can leave a tip. We’re gonna go to the Apple Pay. And the demo is sexy as hell yes. Online. And he just sits back and he goes, holy shit. And I’m like, What is he? Like? He’s like, how the fuck? How many people? Are you? How big is your team? How much have you raised? And I was like, oh, you know, like, we did a little seed Brown, blah, blah, blah. We just do this whole story. And then you know, that was not eight months ago, nine months ago. I mean, since then, Daniel and I talk every other day. And about four months ago, I was in San Francisco, we went out got drinks. I was like, let me just tell you that I knew everything about you. And I met you. And I was like, here’s how I break down.

Was you surprise?

I don’t think so. Because he afterwards, he was just like, I think the truth is, if you’re honest about it, yeah. Then they’re like, fuck, that’s clever. I should be more like that. Right? I should be better disciplined about like, how I get in the door. Yeah, it’s like, if you go to a bar, I’m not gonna sit down next to it. I’m always gonna sit next to the girl. Yeah. Because then you’re just like setting yourself up to like, run into each other. But I’m never going to talk to her. I’m only gonna talk to the bartender about something that I think she’ll ask about. Because if she asked me, then she’s a predator, if I ask her on the predator, never be the predator. And so I think about this all the time. It’s crazy, because I’m like, I never need to be the one that’s seeking. But you’re always trying to get someone to seek.

That’s like a perfect example of bringing that philosophy to life. And I appreciate you sharing it. Because I think that if more people took the time, and discipline to use even just some of those strategies, in order to better get to know someone, and have a better opportunity of connecting. Yeah,

I’m just more open about it. Right? Yeah. Like most people would be like, Oh, I just asked a lot of questions like, Okay, fuck off. Like, yeah, I asked a lot of questions. But like, I’ve done a fuckload of research to Yeah, and I’m not sitting there pitching. So I knew exactly what questions to ask to get to an emotional trust level. Like, there’s very big difference than that, and letting like feeding somebody’s ego, like, how did you start your company? Like, I’m gonna ask that, right? So I can talk about snowboarding, or you lead someone down a path where you know, you’re gonna get to something that you mutually have in common, which is very different. Yeah. And no one does it. And they think like, it’s not work or bid like, that’s all it is. And as long as you’re not at the end of the tunnel, what worry, he’s like, I fucking like your product. I was like, I like your brand. I hate your products. He’s like, That’s cool. And, like, they have an amazing brand. And they’re a huge travel brand. And it’s a CEO who I want to know, to learn from and respect. And now he’s become one of my friends. That’s awesome. And I think that and friends and like trust is how business gets done, to be honest with you, when you like, get in the backroom. It’s all just like, that’s how that’s how things happen.

Well, that’s, that’s how you close around. And that’s how you you don’t have to pitch. Yeah, I

mean, that’s, it’s one strategy. I’m not saying is the only the best strategy is you build a product that just takes off and people are chasing you, right? Then you do whatever you want, right? If you don’t have that happen, which is hard as hell, and it doesn’t always happen. A lot of strategy is involved, even in relationships and building and trust so that you can do it, even if you don’t have the traction needed. Yeah. Which is more of the scenario that we were in.

Is there one connection? Like the connection with the CEO of Lonely Planet? Is there one in particular that sticks out in your mind as a key connection that you made? And then how did you get that connection?

Um, like, I mean, Robert Stevens. He’s the founder of Geek Squad. It’s like a $4 billion company now he started on a bike Take on Minnesota. I asked him to do an interview for ask on Twitter. He said, Yes, I interviewed him. I then invited him to the acid dinner where Andrew Warner was a moderator. Yep, with a bunch of people that he thought were more influential or as influential was him, the founder of geek, the founder of the host of Mythbusters was there. He was there, a big venture capitalist was there. Chase was there all in like all in then Andrew was the moderator. And the only thing we do at ask is, you can’t have a phone, you can’t record anything, you can only write in a notebook, and everything’s gonna be insanely personal. And we just, it goes deep, it seems like it’s insane. And actually, it’s kind of a little too aggressive. But it’s everyone leaves there with a mutual different respect they had for everyone in the room than ever before. So he came so then him and I afterwards, he wrote me this note of like, holy shit never been anything like that. And then we just kept kept sharing ideas. He became a mentor of mine. And then when it came to really get him to join assist, I mean, I went all in. I was like, I love this guy. I could do nothing else to have a person on our side that’s loves messaging, as much as we do loves the business messaging space. And we, I went like to the it was hard. Actually, I got to the point where I was chasing him because I was here. We had a lot of other options, you

know? Yeah. What were you like, noticing it and being like, oh, man, I gotta pull back and present.

Yeah, it was really hard. Actually. It’s hard when you like, you want to hire a mentor? Yeah, it’s different. Even working with them is always hard. I think we’ve had to learn how I’m no, like, we both have opinions. But it’s not like oh, by the way, Robert, do you wanna do you know, like, no, no, like, we’re both here together now. Much different, right? Yeah. So we did a handwritten scribe. I don’t even know if you want me to tell it. So like, our hiring our culture is very much built on. He walked me to the wave Oregon, the first conversation we ever had. It’s a cool site in San Francisco. It looks over to Alcatraz. Yeah, I mean, I remember seeing Instagram photos, the Oregon. Yeah. And so we actually had walked there. And I had a handwritten scribe on handwritten paper because he loves making handwritten paper and notebooks and stuff. With a calligraphy writer, write his welcome letter, sign it to his wife, so I love his wife. Like she loves it. We didn’t get along well, yeah. And then I signed it with m&ms One shot opportunity lyrics at the end, that’s awesome. It’s like a two page scroll in a box that is engraved with our logo, with a hand written with a notebook that has a handwritten letter from me engraved in it with two keys inside that makes the exactly our logo diecast. And once you and once a team, and together you make the company, because a lot of the things I was inspired by to do that were how he built Geek Squad. So I had the uniforms, and I had the logo in the bottom of the shoe. So when everyone walked around with mud on their feet and leave the logo alone, it’s like he was always obsessed with like, things that made them feel like secret agents together. Yeah. And so I was like, how do I build that culture, and I was doing it, but it was based on his side, then I just did it to him. And then he joined. That’s incredible. So it was a lucky day I was in school. So it’s cool to be able to sit next to that guy every day and you know, jam on ideas with?

Yeah, man. Well, I’m excited to see what you guys do next. And that I think that once you get to that next stage, whatever it is, we’d love to have another conversation and

anytime talk through it. I love it. I mean, if there’s anything I can do, I think my style is very suited to my personality. And so I don’t think it’s the only way at all actually, I don’t think a lot of people do it this way. It’s just the way that I know. And it’s worked for me to know, but it’s how I look at life is solely based on relationships, and who you spend time with. And I optimize for it. And so like, that’s all I think about all day is like how to add value to someone that no one else is adding value to in that way. That’s why I never asked a marketer about marketing or sales or about sales, like you’ll learn. You’ll learn if you’re close enough with somebody by observing Yeah, be getting that close to them first.

Absolutely. Well, hey, man, I appreciate it. And it’s due for another beer. Sure. Thank you. That’s it for an interview with Shane Mack. But that does not have to be the end of the conversation. Shane is one of the most prolific entrepreneurs on Twitter, Instagram, all the social platforms. You can find him at Shane Mack, that’s Shane, M A C, on all of those platforms, and you can find his company at assist on those platforms as well. So make sure you check those out. I also really recommend you check out his interview series ask and you can find all of his interviews at start by And for more stories on entrepreneurs, leaders and top talent outside of Silicon Valley, subscribe to us on iTunes at you want to subscribe because we have some great guests Coming up, so don’t miss it. We’ve also got a helpful companion You’re gonna find show notes there with all the links and contact information we mentioned in the episode, as well as some other useful articles and interviews in the powderkeg community. So thanks for listening and you’ll be hearing from us real soon.