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Episode 24: Fear, failure, and success: lessons learned from an entrepreneur extraordinaire

Sippin' & Shippin'
Sippin' & Shippin'
Episode 24: Fear, failure, and success: lessons learned from an entrepreneur extraordinaire

Tanya Phipps|September 30th, 2022


The entrepreneur journey is not easy – it’s filled with twists, turns, roadblocks, and endless questions like “who can I reach out to,” “what am I doing,” and “what comes next?” To thrive in the entrepreneurial space, new founders must find an intersection of three things: understanding audience needs, being good at addressing those needs, and maintaining that passion that started the business in the first place. We sat down with entrepreneur James Marks from Trivial, and founder of Whiplash, to better understand the road to a successful startup and everything that comes along the way. 


02:32 Authority, fear of rejection, and asking the right questions

04:40 First lesson learned: do one hard thing instead of 10

08:04 The “overnight” success story – what sticks and what doesn’t 

09:51 Customer base, community building, and where to find guidance 

15:49 Tales of woe: red flags to watch out for 

17:28 How to overcome assumptions and accept feedback

21:33 Taking action and solving problems mindfully 

26:10 Working on the business vs. working in the business 

3 Challenges for peak season 2022 (and how to handle them)


Brian Weinstein: Welcome everybody to Sippin’ & Shippin’. I’m your host, Brian Weinstein. We’ll be kicking it here every other Friday, quenching your thirst for an insider’s take to enhance your customer experience. So grab your drink of choice, kick back, it’s Sippin’ & Shippin’ time.

All right, welcome everybody to another episode of Sippin’ & Shippin’. I’m your host, Brian Weinstein, and I’m here as always with my co-host Caitlin Postel.

Caitlin Postel: Hey Brian, how are you today?

Brian Weinstein: I’m doing well, I’m doing well. It’s a Friday, so how bad can it be? I survived.

Caitlin Postel: That’s right, we made it.

Brian Weinstein: Yeah, exactly right. And today we have a very special guest, a really, really close friend of ours that we’ve known for a while. Founder and former CEO of Whiplash and entrepreneur extraordinaire, James Marks.

James Marks: Hey Brian. Hey, Caitlin. How are you doing?

Caitlin Postel: Hey James, doing well.

Brian Weinstein: All right.

James Marks: Nice to see you folks.

Brian Weinstein: Nice to see you, too. I mean, it’s been a while, but we’ve had some great shared experiences together, so really happy to have you join us today. What you’ve been up to, man? Give the audience a little bit of background on yourself and give us a little bit of where you are these days?

James Marks: Yeah, sure. So little bit of background. I started my first company when I was 17. I had to wait a week to sign my first lease because I wasn’t legally able to sign that document. That was a vegan grocery store in Pontiac, Michigan, which strangely did not thrive. A surprise to me, certainly, maybe not to literally anyone else. But that was something-

Brian Weinstein: It’s a bit of a meat and potatoes community there. So you gave it a shot.

James Marks: I gave it a shot and well, we can get into what did and did not go well there because some of it was truly magical. I don’t want to say it was all disaster. But that was the beginning of just being in business for me, I was the first entrepreneur in my family and so had a lot to learn. That was the beginning, I turned that into a screen printing shop, which somehow made sense at the time. Then turned that screen printing shop into a fulfillment business, which is how we got involved … which is Whiplash and how we all ended up together.

Brian Weinstein: Crazy. Was it a series of mistakes that led to the fortune?

James Marks: It was definitely a series of mistakes. I think that much is clear that that is definitely how I learned. So I have this weird problem … and I think it’s actually true for any entrepreneur. Where you have this challenging relationship with authority, where you need to disrespect some authority or you’re not going to do it in the first place. [inaudible 00:02:49].

Caitlin Postel: Screw the man.

James Marks: Yeah, there’s something contrarian about starting your business saying, “No, I can do it better.” But then also, it meant that like I said that about paying my taxes. Everyone’s like, “You have to pay your taxes.” And I’m like, “We’ll see about that.” They were right on the taxes thing.

Brian Weinstein: Well, I mean you have to, nobody’s going to tell James that he can’t take his vegan shop and turn it into screen printing shops. It’s not-

James Marks: Right. And no one’s going to tell me that I can’t. So there’s this interesting relationship with authority that I’ve been struggling with my whole life. Basically anything that’s going well for me now is because I insisted on doing it wrong the first time. Finding out like, Oh, okay, you do have to pay your parking tickets and then correcting for that.

Brian Weinstein: Right, right. Exactly, exactly. Somethings you can get away with. But you’re right, I mean, look, it all starts out with … and I came from a family business and it was very entrepreneurial myself. You’ve got to always be questioning.

James Marks: Yeah. Our friend Jeff from Whiplash said, “The entrepreneur always bets on himself.” I think that’s really true, and I think I get played by that sometimes. But it’s just, I’m going to bet on myself. Whether that’s a good bet or not, that’s sort of the entrepreneur’s perspective.

Brian Weinstein: Right. I mean, is it fearlessness?

James Marks: Absolutely not. So that’s actually-

Brian Weinstein: Okay.

James Marks: What’s a really interesting thing is when I look back at my successes and failures and just everything, there’s actually a fear of rejection that has been just ever present in everything I’ve done. Some of my … when I look back at a problem area, I’m like, “Oh, that was actually fear based thinking.” So it’s not a fearlessness, but maybe it should be. Or at least recognized, I don’t know.

Brian Weinstein: Right, right. Coming out of your first experiences, what was really one of the first lessons you learned?

Caitlin Postel: Oh boy. Where do you start? Pay your taxes.

James Marks: Yeah. Pay your parking tickets. Pay your non moving violations, they will come for you in the end. So that’s probably the first lesson I learned is that the state has more time than you do, and they will come for you in the end. No, there’s nothing too tragic there. But yeah, let’s see, going back to that grocery store, I was 17, turning 18. So idealistic and blended with that was this naïveté. They both sound ridiculous.

Brian Weinstein: Right.

James Marks: I was very naive.

Brian Weinstein: But you had them both? I had them both.

James Marks: So I think starting there, you’ve got to be filled with that optimism. What I try to do too many hard things at once. Looking back, you’re like, I was trying to do a vegan grocery store 30 years before vegan was a household name. Right now we’ve got Impossible and Beyond and it’s in every grocery store and you can get a vegan Big Mac or Whopper at Burger King. That was not true in 1995. So I was trying to do exclusively vegan in a very difficult, kind of burned out neighborhood, as a first generation entrepreneur, self-funded with a small inheritance. You can really pick one hard thing. Okay, what is our hard thing that we’re going to tackle? Maybe if you’re really good, you could do two. But trying to do all of them at once, it was just too much.

Brian Weinstein: Right. I guess it’s one of those things though, maybe the lesson that you learned, there’s things that you can draw from that you can extrapolate in your next venture. Is that fair?

James Marks: Yeah. That’s definitely fair. So it’s the school of hard knocks. I graduated high school a semester early, did one semester of community college and said, “This isn’t for me.” So what I meant was that I got all of my learning in business and just having it … like I said, everything has to defend itself to me. Talked to accountants or bookkeepers who, to me, just reeked of mainstream and the man. I didn’t want anything to do with these people. But I would sort of hear their thing through a filter of my problems with authority. Then they’d be like, “You should be making a profit and loss statement. And this is how you manage your business.” And I’m like, “Oh, we’ll see about your profit and loss statement. That sounds like something the man would say.”

Brian Weinstein: Right, exactly.

James Marks: Then going bankrupt and then I have to come to it myself. I’m like, “If only we had some way to track how much money we brought in and then subtract out our expenses. We’d know if we were going to have money for rent or not.” Then you’re like, “Oh, that’s that thing they were talking about.”

Brian Weinstein: Oh, the P&L. Now I understand.

James Marks: Now I understand. So everything has had to defend itself to me. I think I’m a bit of a skeptic in a healthy way, sort of.

Caitlin Postel: So James, moving towards the fulfillment, the story of Whiplash. It’s a story I love to tell, it’s so well received. I guess the way I tell it is the way that the media likes to tell those stories. I’m doing air quotes for the folks that can’t see it. So the overnight success story, and I was surprised to learn that you had tried … Whiplash was your third try. I never knew that, I’d leave that out of the story.

James Marks: Well it’s because no one knows about the first two because they were dead in the water.

Caitlin Postel: Right. So tell us a little bit about what made the third try stick or what you did differently that made the overnight success, that was 12 years in the making.

James Marks: Yeah. So in case it goes back to, there’s a point after the grocery store where I had a screen printing shop. We did t-shirts and stickers for bands, basically. Bands and small businesses. So one of the natural things that happens there is the band goes on the road and who is going to run the web store while the band’s on the road? We can’t just not ship orders for two weeks. So there’s this obvious relationship where we’re making all these shirts, what if we just kept them on our shelf and then shipped them out as people ordered them? Which we now know is called fulfillment, then it’s the beginning of a warehousing business.

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So, that was really trying to figure out how to expand the screen printing shop. I’ve actually seeing a number of other screen printing shops, I’ve got friends who have had that work successfully and were able to pull that off. I couldn’t, for whatever reason. I think I didn’t know enough people and there wasn’t like a cold start problem, where if you don’t have enough customers to make it an ongoing activity and profitable or at least generating interesting revenue. Then it just kind of dies on the vine. So we did that twice where-

Caitlin Postel: Learn that lesson twice. Yeah.

James Marks: Yeah, exactly. I think I just learned it again six months ago. I think I’m continuing to learn that lesson that you need to launch with customers. You can’t just launch into a vacuum in this field of dreams, build it and they will come. You need some daily volume for people to care and stick around.

Brian Weinstein: I would imagine, you’re like, okay, you’ve got all these grand ideas. You get them out there and who you getting them out there to? And if you don’t have a flow.

James Marks: Yeah. This goes back to the grocery store. I had some friends in the music scene and I think I had not realized that I thought my friends were going to be my customers and it’s going to be this magical land where they’re all in here every day buying their groceries and this is how we’re going to get this business to work. That’s just not the way it works. Maybe your friend or somebody who really cares about you just going to support you in some way. But you need a customer base. You need many more people than you know currently and your customers are going to be built out of strangers. So I think when you have that cold start problem, it’s how do you get that small base of maybe strangers, maybe friends, to get you going? Just so you can make it over that first six months, let’s call it.

Brian Weinstein: Well, using your band analogy or using a band analogy, you first start playing out in public and all of your friends and family come to see you and you’ve got this sort of mini packed house for a few shows. Then they all have to go to work the next day.

Caitlin Postel: It sounds like how our podcast started, Brian.

Brian Weinstein: Right, exactly. Exactly. Cold starts are never easy.

James Marks: It went a little too close to home.

Caitlin Postel: That’s right. I felt it.

Brian Weinstein: So with a complete distrust and disdain for the man, where did you go as an entrepreneur to learn more and get some guidance? And how did that work?

James Marks: Well, I think as a mistake, I just always turned to myself. I always thought I had to come up with the answer myself. Just maybe a little bit too afraid to ask questions, was afraid that I would get bad answers. So I thought I had to do everything myself. I think it held me back in a lot of ways. I put the question back to you, where do these networks come from? Because I don’t necessarily know that I have the right answer.

Brian Weinstein: Right. Well if there’s one thing that is out there is more prevalent now, I think it’s people can find their people, their community. That’s out there. I certainly have met serial entrepreneurs like yourself along the way. Is there an entrepreneurial network out there? Or a network of entrepreneurs, I should say, that you can turn to for guidance?

James Marks: So what I have found … so I’m starting another business right now over the last year and any community I joined … there’s some interesting communities out there. There’s a website for Bootstrappers and they’re just building their first businesses and they’re all together. There’s some support, but it’s like social media where I think sometimes it hurts as much as it helps. Where you do meet a couple of interesting people, but then you’re also comparing yourself to other people on there and you’re getting their highlight reel and comparing that to yourself. Sometimes feeling bad about that, sometimes discouraged.

The thing that I have working right now is that we’re building a business that requires a lot of trust. We’re building profit and loss statements, we can see people’s revenue. The only people who I realize want to work with me right now are some of my oldest friends, some of the people that I’ve known for literally 20 years at this point, who are willing to talk about the problems that they have. That there’s this huge trust issue. Because if you don’t know me, I’m just some guy off the street saying, “Hey, what problems are there with your business? I want to fix them.” They’re like, “We don’t have any problems.” And this wall goes up.

So it goes back to you have to start a business, you’ve got to have that trust somewhere. I think what I should have done when I left Whiplash was launch my next business out of Whiplash in a way that everyone knew I was doing and solved a problem that Whiplash wasn’t solving. Okay, I’ve got my 10 customers, it’s friendly, it’s known that I’m doing this. Then use that as the momentum. I didn’t deceive anyone, everyone knew I was leaving. But I didn’t build that bridge as much as I should have. I think that was a mistake. Because that was my network. Those were the people that trusted me, people that I was employed alongside.

Brian Weinstein: Right, right.

James Marks: And going back to why the third fulfillment attempt was different, what we had was a customer at that screen printing shop, which was Modest Mouse. Which Modest Mouse is like indie rock legends, platinum selling band. So we figured we could build a business around that, that there was enough daily flow that you could have at least a part-time employee showing up every day and building this thing and there was a reason to kind of keep it going. We mistakenly thought it was go, if we’ve got Modest Mouse, everybody else is going to come running.

Caitlin Postel: There it is. That’s where the story gets familiar for me, that’s where I start.

James Marks: That’s not at all what happened. It took years still even from that point. The second customer was my friend’s, Ghostly International, who’s a renowned digital techno label. Then we started waiting into the problem and the story that Caitlin has been telling, which is, they needed a warehouse management system. We didn’t even know that term at the time, we’re they need just a system that works well and communicates all this information. It was five years in before we started calling it a WMS. This guy didn’t know what a WMS was.

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Caitlin Postel: Right. PNLs, WMS-

James Marks: Everything has to-

Caitlin Postel: Those acronyms.

James Marks: Yeah, exactly. I’m not listening to that acronym. I’m not going my own thing.

Caitlin Postel: I’m going to Google it and poo-poo on these answers. These aren’t right.

James Marks: Exactly. And then you’re like, “You built a WMS. We got to a term for that.” You’re like, “No. Okay.”

Brian Weinstein: So, I would imagine what we want to convey here too is a message to entrepreneurs who are listening. For young entrepreneurs starting out, what are some of the cautions and red tales. Tell your tales of woe, James. Tell those red flags that you may have swam past and haven’t realize, “Oh, that’s why it was there.”

James Marks: There are so many. I think one of the biggest ones that hit me personally, and I think I had read about it in books and I had to experience it myself to really get it. Just like the silent assumptions, where you’ve answered a question yourself and maybe didn’t even realize you had made an assumption, but that you’re going out on a limb. My example of that is in the beginning of Whiplash, we were buying the postage to ship all these packages and that’s on a cash basis. We were billing our customers net 30, so at the end of the month, we’d prepare them at invoice, they would write us a check within three days. They’re very fast payers and pay us back for all that postage.

But what it meant was we couldn’t afford to run the business because we might spend, at the time, it was like $5,000 a month on postage that we weren’t going to get back for 30 days. We just didn’t have the money to float that for them. So this was becoming worse and worse as the company got bigger. I assumed that if I asked for more money from my customers or to change the payment arrangements so that we would have that float, they were just going to leave. I was like, “This is critical to their businesses. I can’t ask for more money.” There’s all this fear and assumptions around what I think is going to happen if I tried to change the payment relationship.

So we got to this very bad day where I woke up, the bank account is negative. Sean, my co-founder and I are tapped out. I know neither of us can really afford to put any more money into the business. We’re just like, “We can’t ship today. What are we going to do? We literally are going to break our promises over this.” so I see that, take a shower and just try and decide how I’m going to react to this. What I decide is we’re going to have to switch to a prepayment model. All of our customers are going to leave and that’s the best we can do, is we’ll just start over with this prepay model.

We find some room on a credit card somewhere, we get through the day. That day I email our customers and say, “Hey, we’re going to switch to this model. I’m really sorry, but we have to do this.” The response is still overwhelming to me, I get chills just thinking about it, how wrong I was. No one cared. They all switched to the prepay model, with the exception of one customer asked if they could go into it in a month instead of immediately. So our business changed overnight from something that was killing us, to something that just worked and could grow frictionlessly. And nobody cared. I had made all these assumptions about how that was going to be reacted and I was just so wrong.

Caitlin Postel: Yeah, it’s wild and I was reading a few of your articles and I loved the line where you said, “Do not confuse assumptions with the truth.” I think we’re all very guilty of doing this. This assumption that you made blindly could have buried you again.

James Marks: Yeah, yeah.

Caitlin Postel: So it’s like, how do you take those calculated risk or what you call, get outside the building to overcome these assumptions?

James Marks: Yeah. So the reality is I wasn’t talking to my customers about my problems. Because the reality is that it was a very collaborative relationship. I think I am a little bit sensitive about money and you’re scared to talk about money cause it’s an admission and you’re like, “Hey, we’re having a cash flow problem.” You’re making yourself vulnerable in that moment. Maybe your customer-

Caitlin Postel: Sure.

James Marks: I’m worried my customer doesn’t want to hear that we have a cash flow problem. They’re like, “That’s your problem, not mine.” But we had a collaborative relationship with our customers, where we can have those conversations. I wish I hadn’t waited until I was against the ropes about to go bankrupt on this issue and just called it a little bit earlier. I can think about approaching it with more confidence, which is just, “Hey, we’re having an issue. I know it’s just a function of how we design this and we’re going to fix that. It’s not a big deal.”

Caitlin Postel: The power of communication and conversation, they were asking their end users for the money up front. They know the cost associated with this.

James Marks: Right. Because that was what I was thinking, was like, “Oh, they are used to having this float loan because they don’t have to pay us for net 30. They get it from their customers up front. This is going to kill their business.” The reality is … I forget the terms for all this. But I was projecting is what [inaudible 00:20:24]. I was having cash flow problems, I assumed they were having cash flow problems. They were actually running their business that had been up and running for years, they didn’t have the same kind of startup problems that I was having. So I was projecting and I think it’s hard to see through your projections sometimes.

Brian Weinstein: There’s a fear of the answer that you’re going to get back. I always used to joke that I crave feedback, I loathe criticism. The same can be said-

Caitlin Postel: Not you, Brian. No.

Brian Weinstein: For asking the questions and you’re afraid of the answer that you’re going to get back. Especially in a case like you were in, because if your customers had fought back, you would’ve been in a pretty sticky placement at that point.

James Marks: I would’ve been out of business. I think a loathe feedback, hate criticism. My wife and I talk about this, when you’re like, “Oh, I want to show you something.” And they’re like, “Are you looking for feedback or a pat on the back?” Because it matters. You’re like, “Actually, I don’t want feedback. I want you to tell me I did a good job.” And sometimes it’s what you’re looking for.

Caitlin Postel: I love that. I always say, ‘What kind of listener do you want me to be?”

James Marks: It’s a quick check in before I ruin your night.

Brian Weinstein: Right, right. Exactly right. Exactly right. So are there any other areas … I mean, that was a great one. Again, for younger entrepreneurs or maybe someone that’s only coming out of their first bankruptcy. What are some other areas to focus on to really drive forward? Look, there’s two phases to it. I guess I’m going to ask this in a two part question. One is, what are some other areas? But two, you get to the first of level of success as an entrepreneur. I’ve always felt like the old expression, if you’re not growing, you’re dying is really, if you’re not innovating, you’re dying. So where are some areas and traps and pitfalls to watch out for there, as well?

James Marks: Well, I can only speak to my own patterns that I’ve picked up on. I think one of the things I’ve noticed is I reach for taking action right now, even if it’s the wrong action. Somebody’s like, “We need to get to China.” And I’m like, “Great, I’m going to start swimming because we got to get to China.” And they’re like, “That’s a bad plan.”

Brian Weinstein: That’s a bad plan.

Caitlin Postel: But I thought you said that’s what we were doing.

James Marks: Right. They talk about having a disposition towards action. I think I’ve got that. And so sometimes you need a disposition for thinking two steps ahead to that moment where you’re drowning, still clearly in US waters.

Brian Weinstein: It’s interesting, you say that because you do get yourself trapped in a situation where you want to move forward. Everything is, you’re busy. And taking that step back to be more strategic in your thinking sometimes is so difficult to do when you’re in the moment.

James Marks: And are you busy with the right activities that are setting you up long term? Because if you’re paddling to China, you’re busy, you’re very, very busy. And you feel engaged and it’s a life or death struggle, literally in that case. But it’s all the wrong work.

Brian Weinstein: Yeah, absolutely. You’re not seeing the fact that you’re out there paddling and you’re fighting off the sharks and you’re making your way across. While if you had thought it through, you could have been there already and been activating whatever your next strategic plan is.

James Marks: Yeah, exactly. So trying to understand, I guess, how you’re spending your time. I keep a lot of notes personally. Every 30 minutes of my day is documented. Just talking to myself, basically, I’ve realized. Trying to form my thoughts into, am I working on a high value problem right now? I know I’ve got personal traps that I’m actually indulging a little bit right now, but I know it’s a trap at least. Which is going deep into the solution myself, I like to wade into the technical area, I like to wade into the code.

I realized, actually, once Whiplash was at a sufficient scale, that there was real complexity to manage there. I was actually hiding from some of the other problems that I didn’t know how to solve. Oh, I don’t know what’s happening with maybe a lawsuit or an HR situation. I don’t really know what the plan is there yet. Let me go spend 35 hours working on some code where things are clear and I know what to do. This idea that if I just work hard enough, I’ll fix it and everything will be better. I was actually hiding from some of the other stuff that I should have been addressing and higher leverage activities for a CEO.

Brian Weinstein: Right. I mean, some escape to the bottom of a bottle, others go to coding.

James Marks: We’ve all got our vices. Brian, don’t judge me.

Brian Weinstein: As long as you don’t judge mine.

Caitlin Postel: Coder tequila. Either way. Either way.

James Marks: I got a little bit lucky in life and that I’m slightly allergic to alcohol. So there’s some natural protection there.

Brian Weinstein: Right, right. Exactly. Exactly. No, that’s great. It’s just so hard to sometimes rise above and as a business owner, you get pulled into these, helping put out fires and doing so many different things that it is hard to continue to work on your business.

James Marks: Well, so that’s the fascinating, the language you use there sums it up. Are you working on the business or are you working in the business? The reality is, I think once it gets going a little bit, you end up being in the business. Which means no one’s working on the business.

Brian Weinstein: It’s one of the easiest things, I had a business coach, and we talked about that years ago, before I had sold my company. He said, “I see what you do and you’re very in the business.” I will say, and it’s really a matter of, I had some great people working for me. But I didn’t have any great leaders to backfill me in the role that I was playing, working in the business. That did not allow me to work on the business and I think that’s a real critical piece as you’re growing businesses.

James Marks: Well, it really turns into how big the business is going to get and how far it’s going to go. When we were talking to VCs early in Whiplash and Whiplash didn’t really end up being much of a VC business. We took a little bit of funding in the end, shortly before we were acquired. Years before that, we’re talking to VCs and we would get rave reviews. But what they were listening for I think was really that question. Because the rave reviews they were getting was like, “Oh, James is fantastic.” Which was flattering, but then the VCs are like wrong answer.

Brian Weinstein: Right.

James Marks: James doesn’t scale.

Brian Weinstein: Right. No, 100%.

James Marks: And I’m like, “You don’t know how hard I’m going to work.” They’re like, “We don’t care.”

Brian Weinstein: Prove the man wrong again, James.

James Marks: Right. So of course, I take that as a little bit of fuel for the anti-authoritarian fire, which is ultimately why I sort of don’t. I think it’s interesting, this whole entrepreneur authority thing, there’s a lot there for me to unpack still. But VC, it’s really asking for permission. Please sir, may I run this business? It’s just like, no, no. I think I’d rather be a bootstrapper, even though I have friends who are VCs and I see the power. I’m not saying we won’t do it again, but I realize it just feels like giving power away. Like the whole reason I’m running a business is so I can like, no, we’re going to do this right, we’re going to do this … what I think is the right way to be done. Which is thankfully serves customers and all those things.

Brian Weinstein: The evil just becomes when you … in order to get to and see your vision through when you need their cash.

James Marks: Right, right. Exactly. Exactly.

Brian Weinstein: Damn you money.

James Marks: Yeah. Maybe if I had different … if my inclination was to like screw over customers, then maybe there’d be something evil in my approach. But I am so customer driven. I think there’s a chart where I’m just extremely high on empathy and I’m like, “Oh, that customer who just fired us, filed a lawsuit and was [inaudible 00:29:08] against us and fabricated this lawsuit. I can see where they’re coming from. It’s like, that’s not always helpful. I think it actually limits me as a CEO. I think a CEO can sometimes be a little bit low empathy and just say, “Here’s the path and I don’t care who gets … heads will roll.” Type thing. I’m not that guy. So I guess at this point in my life, I’m just like, I don’t want to be that guy. Maybe I’m not Steve Jobs, that’s fine. I just want to be myself and do my thing and hope that there’s value in that, basically.

Brian Weinstein: Well, as that entrepreneur, you have a passion for your product or service. And anyone who will give your product or service the time of day, you’re going to have passion for them too.

James Marks: Yeah, exactly. I think these are the questions I was asking when I left Whiplash and trying to figure out my next act, which I’m still in the process of. But I came to this question, I think through my coach gave it to me, who do you want to serve? Because at the end of the day, when you show up and your inbox is full, or your phone’s blowing up or whatever. Who do you want in your inbox demanding answers? For me, that goes back to the indie businesses and artists and bands and people that I can relate to. It’s like I want their businesses to thrive. So as long as I orient around helping and being of service, then I think the rest takes care of itself to a degree.

Brian Weinstein: Yeah. No, that’s amazing. It really sums it up and it sums up … look, I mean, this is, again, the opportunities that are there for entrepreneurs to come in and find their passion and help share that with whomever in their way, the opportunities are there.

James Marks: Yeah. And find that intersection point of what do people need help with and what am I good at? And what do I have passion about? Because when you get all those three things to line up, then suddenly you’re gold.

Brian Weinstein: Yep. Absolutely. All right, James, man, it’s been great catching up with you and appreciate you coming on today.

James Marks: Thanks for having me. It was fun.

Brian Weinstein: Been awesome. Caitlin, you want to walk us out?

Caitlin Postel: Sure. James, thank you so much for joining us. Always a pleasure. Thank you everyone for listening. Tune in next time on your favorite podcast platform. Thanks guys. See you soon.

Brian Weinstein: Peace. Thanks everybody.

James Marks: Thanks everybody. Bye, bye.

3 Challenges for peak season 2022 (and how to handle them)

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