The Wisdom Wall

“Getting a million dollar SaaS ARR is probably as hard as getting a million dollars in EBITDA, let's say in a services business. And guess what? They value those, those streams are valued exactly the same. So like the market is very efficient in terms of how it treats these businesses and these business types.”

“anyone who's worth being an advisor probably should have 25 to 50,000 dollars to put into your company.”

“the new Facebook, you know, at paradigm is targeting like creative is the new targeting. So for anyone listening, running Facebook campaigns, you don't need to target anymore. It's broad. You let Facebook's algorithm figure it out.”

“everybody tells you entrepreneurship is about freedom. They tell you it's about making money so much money that, you know, you want it to do with it, or they tell you it's about changing the world. And I think those are all lies. I mean, I think that the actual best highest purpose of entrepreneurship is to improve…”

“I think the most successful companies is somewhat obvious or not obviously, but it will take one square of that matrix. Like I said, customer service for banking and go, that is a very specific solution. I'm going to have the best models. I'm going to teach, I'm going to use open AI, but I'm going to really, really…”

“building an advisory board is one of the, I'd put it as one of the many distractions that entrepreneurs create to think that they're going to build a better business instead of just selling stuff to customers.”

“inside of a company, oftentimes the returns on capital are way higher than even an investor ever gets. Like there's initiatives, hiring five salespeople can have a 500% return in a year if you do it well, right?”

“I think, I think every problem can get solved with a weekly meeting.”

“I don't think it's good actually for me to be in these channels. Like, I think it's important that I'm not, actually, because when I'm in them, then it feels like, oh, Jesse's alongside. He knows what's going on, and even we had, we had our first version of those meetings last week, and Carolyn was like, Jesse, this…”

“the middle ones in my experience, you know, it's sort of the, the hammer and a nail thing, right? It's like, if you're a hammer, everything looks like a nail. So everything they look at us through the expected value of how big could this be? If I put a dollar in, will it get a multiple over it? And there's a lot of, in…”

“as the leader, sometimes it is important that maybe the team's a little bit less productive for your benefit, because you're ultimately the only person who can see everything that's happening and you're ultimately making most of the decisions. Right. And so it's not a crazy thing for people to have to do things like a…”

“I would tell people, most people, if that's similar, like you go give yourself two years, Quit everything, go all in and make it work. And I think that sets you up for more success around entrepreneurial ventures.”

“It's the whole conversation of whether the idea is big enough or not too big or no, it's all ego oriented versus just waking up in the morning and going, what will, what will make, you know, what will energize me today? What will be something I'm excited to do? And I think the more I've like my practice, it's a very…”

“the fear of commoditization of business is totally driven by venture. It's not driven by entrepreneurs because every business you can build a moat around over time and, and you can build some resilience.”

“And so that's the one thing about B to B that I think is beautiful is you can just get on the phone and start pitching people. You see their reactions, you get their feedback. It's, it's in some ways it's way easier than B to C.”

“when you're doing really big deals, you don't want to pretend like a person is into it when they're not into it. You really want to make sure they want it. And so they had a little rule where they were like, wait three days for your follow-up.”

“Recession is, recession is the economy goes down by three percent, sort of up by three percent. So we go from being a 20 trillion to being a 19.5 trillion or 20.5 trillion. Like, I just, I personally just don't believe in that effect. Like, you think it's an excuse? Yeah. Well, yeah, sure. Will the purchase rates be a…”

“there's certain advanced strategies you can still hack, but I wouldn't worry about them if you're listening and you're spending less than 500,000 dollars a month on Facebook.”

“on average for every ad dollar of any platform, there's about 20 to 30 cents in services, support, software, tools to make use of that platform.”

“fear is the most common. By the way, it's the most effective, so I'm not judging fear, right? ... Yeah, you put a gun to your head, you're gonna run faster than you've ever run, but the downsides of fear are that they leave a negative residue on you and others, and they're not sustainable”

“layoffs are a function of greed, and there was a moment where people were just overbuilding a lot, and that's what leads to layoffs, and that's what leads to a lot of this stuff.”

“I've missed 10% of my flights as a life rule. Um, you're spending too much time in airports if you don't.”

“I try to avoid standing meetings. And the reason is, is because what's important this week or for the next week or two is going to be very different than what's important in the following two weeks. And I like to change and shift my hour, like where I spend my time depending on where I need to be, you know, what needs…”

“my experience, okay, ours are really good when a company understands itself really well. Most people listening, me, you guys, like, we don't know our business that way.”

“people like him don't ask what's Correct or incorrect or what's right or wrong in the sense of running a business. They just do what they know and what they want. And I think there's something about entrepreneurs not worrying whether or not it's, is this the right course of action? He's like, this is just what I know.…”

“The third one I would, I would take issue with unless you're a Y Combinator venture funded. The third one you said, which is make sure that like few other people can do it. Right? Because, don't get me wrong, I, I think way more energy is spent on people being like, oh, it's not proprietary enough, or I found a…”

“hiring, especially in an early stage company, is extremely hard. Like, I was just talking to, to the CEO of Growth Assistant, I was telling her, a bet, a fifty-fifty is a good rate, and then when it comes to executives, it's even harder.”

“If you're gonna tell people you're a family, you got to behave like family and family doesn't fire people. They find other things for them to do. And there are companies, by the way, that operate like that. There's nothing wrong with that. But if you're going to run your business, if you have investors, if you're…”

“I think startups overly focus on it, and again, like, find it and use it as an excuse for why they can't close a deal. You know, if you think about HR software. It's a multi-billion dollar market. If you're starting a two million dollar ARR company, getting to three million the next year, sure, people, your sales…”

“no business starts being defensible. And I think it's important for entrepreneurs pitching when a VC goes, oh, how do you make this defensible? You go, well, today it's not defensible. If it was, how the hell would I be starting it?”

“fear is kind of obvious, but if I put a gun to your head, You're going to run faster than you've ever run in your life. So the benefit of fear is it's super effective. And that's one of the cool things about this paradigm is it never argues, because one of the first things an entrepreneur pushes back, oh no, but dude,…”

“it doesn't matter how good of a delegator you are, if you're thrashing your team all the time, or you're not organized enough to know what needs to get done by when. Like, delegation's gonna be tough.”

“I have to think through this TRM thing for people, because if the main task of the business, they're lower medium on, it's never going to work. Right. Adrian was really high on recruiting people from the Philippines. Like I did not, I never, I detected it going fine. You have enough people. But I was like, if I had to…”

“There are certain times in an organization where, you know, just like on an airplane, like the pilot has to take carte blanche and basically say, guys, I'm going to zoom in and I'm going to own this and we're going to, I'm going to quarterback the crap out of it. Um, obviously if you're doing that all the time, it's…”

“you and the CEO have to be out of the delivery of the service other than maybe coming in, whatever you're willing to do once a week, once a month. With like, I'll review stuff and give specific comments. And that's, and when you do that, it all gets up leveled into the organization.”

“Consider for a second that that founder doesn't know how to create safe space for themselves. How about that? Right. They have no idea how to actually even not judge and criticize themselves, much less anybody else.”

“One of the things we've overlaid on top of that, and I, I'll, you know, this format is like facts versus stories. And so we, you know, we try to get people really tight on, I don't want to hear spin in that meeting.”

“Typically if you're in a, if you're in a business that has demand built in, meaning people come and search for it, like insurance is very common in this way, or, uh, travel search is a way better, uh, way better place to start.”

“Facebook and TikTok, I mean, there's overhead and learning how to use their platforms. That's real. And so I would never start by spending more than 50 bucks a day.”

“your problem is not going to be that people are going to see your content and judge you. It's going to be that your content's not very good, and they're not going to see it. And, and like, but that's the reality of all these things, right? Like, the more I've been doing all this TikTok stuff and barely gets watched,…”

“I think one walk on a conference room floor, like I almost want to make it a requirement for gateway X before we start a business, we have to go walk a conference floor in our, in the industry, because dude, you learn so much about what's there, what's not there. You can kind of build a market map in your head.”

“even when a company is five, six, seven people, I think that's kind of the right time to start the values conversation, because, um, It sort of gives people a guideline. It's leverage for the founders to kind of give them a guidepost for what people will do when they're not around.”

“if you're a new, new founder starting out, I typically say like, give yourself two years. If you don't have anything going interesting within two years, Then probably you should do something else. Two years is a long time if you're giving it your all every day.”

“Carolyn, if something is 10 or 20% better, it's not actually better. Like, it's not a champion. It's just another iterative sort of, like, incremental ad. And, you know, she's never experienced this, and I think you probably have with the brew. I have a million times. I was like, when we have a winner, like a real…”

“what I like about these luxury brands and I think why they're so successful is they're the opposite of venture funded companies. You know, they, they cannot force growth by definitely by definition. If they force growth, they will stop being a luxury brand.”

“The other thing I do is at any given time, I'm probably working with, like, Three or four people on different ideas, but one thing I found that's just really effective is like, Hey, here's an idea. Like, why don't, why don't you go and let's go like, go do this and let's see what happens, see what we can learn from it.…”

“to me, that's like how I would probably try to build moats is get, make the best solution for a specific customer segment.”

“by the time the thing makes its way to a best practice hook, it's basically too late.”

“That's the whole internet is based on an arbitrage between revenue per impression and cost per impression or revenue per click and cost per click. That's for anyone listening. That's how the whole internet works.”

“Well, you have to get five to 10 a week because that's the, everyone is an at bat, right? And so that's number one, you gotta keep getting the sales meetings. Number two is you gotta adjust, you know, and again, ideally build a culture of adjustment after every sales calls at Kahani, we try to end it a few minutes…”

“If you're running the business, you're running the business. There's nothing wrong with that, but don't also try to do those other things because that's not going to work and vice versa. Um, if you're not running, you know, if you're not running the business, you have to find the right people and surround yourself with…”

“when you target, because you're limiting their freedom, they actually charge you more because they have less auctions you can be in at one time. Whereas when you say, go after anybody, I don't care. It lets them explore freely, which ultimately means you can be in more auctions, which is a higher chance of finding a…”

“There is a, I, my rule of thumb, you know, is 90 days of more than 50% of your time and energy to crack something. Like, to truly walk away and say, this didn't work.”

“I think most founders undervalue how important it is that they, it's a personal, it's such a personal choice. So in the case of John, I mean, John was like, Hey guys, you know, we're going to sell this business or, or I might, you know, I need to, I need to change the scenery one way or the other sort of, right. That…”

“typically when you go through like a salary negotiation with someone or a challenging situation, like Everyone basically prices in that you're going to hurt your trust with that person a little bit. I'm going to piss them off a little bit, but we'll get to a place. He's always like, no, how do you get your trust to go…”

“getting it across the finish line matters to the world, like people, the way you're treated, the way kind of that, that success”

“The predictions are going to be wrong for sure. We're going to get them wrong, but the, the thought process and the cycling around in your brain and talking through with your teams, that's where the value comes in. Cause then when you do spot something or something does come up, you're ready to take advantage of it.”

“By the way, that's one of my signs of like a mature, self-aware entrepreneur. Is when, like, a person says to me, like, I know this really well, so I'm gonna, but these things, like, I have no clue. And then someone, like, has the same level of knowledge on everything, I immediately don't believe anything that they…”

“if you spend too much money too fast on Facebook, you actually, their signal is not dialed in yet. And so you waste your money and you don't actually figure out demand.”

“Having someone from day one is, is much more critical than I thought, I think I realized, um, and so I would try to find that person now.”

“once you're at a hundred, you're never going to have more people reporting to you. It's not like the CEO of a 10,000 person company has more than five to seven people reporting to him or her.”

“When their seats are emptier, they try to get more mileage ticket flights because it's cheaper. It's basically incrementally a cost of zero to them, right? If an airplane is flying and it's going to go and there's a seat empty, they should sell it for whatever points they can get because those points, they come back in…”

“there's some guy in corp dev and private, that's their job. Their job is to know who you are. It doesn't really mean all that much. And the flip of it is there's nothing down downside about building a relationship with them, but it's towards the bottom of your priority list.”

“the second you raise institutional or professional money, which I define as sort of money raised from people who have raised from other people, right? Like, like, like Sophia said, it's their business, not a person's individual capital. Your business becomes a financial product. That doesn't mean you have to treat it…”

“Fear is very effective, right? You put a gun to my head, I'll run faster than I've ever run. But then as soon as the gun's gone, I stopped running. Right. And in his case, he got, became the richest man in the world. And, and Microsoft didn't sustain his motivation.”

“media has a crazy, I mean, it's the original software business, right? You do it once and you, that's it. And it's the same thing we're doing right now. We record this once and that doesn't matter if a thousand people listen to it or 50,000, it doesn't, it doesn't cost anything more.”

“there's a lot of people out there who are inexperienced, but seem to be really great. That's my favorite group to hire from. But the biggest mistakes I've made of is people who are smart, who are experienced, but like they talk a good game, but they're not actually that good. And I think for a first-time founder,…”

“I wouldn't now tell anyone listening to ever try that. Like if that happens, if you're Nikita and in nine months, they buy you for a hundred million. God bless. Like that's amazing. I don't think that's the norm.”

“pretty much within five or 10 people working for you, more of your job is about people and about leadership than it is about the idea and about the market.”

“When you control someone's salary, and you control their livelihood, you'll never be the same as them, and you can't, even if you want to be buddy-buddy with them, it's never the same, and you have to take that responsibility, and be very careful about how you, how you manage it, and how you wield it”

“one of my big recommendations is always, wherever a person seems to come in most commonly, if you're a manager of that person, just ask them to try to come in a couple levels above it. Right? And as a person, if wherever you see yourself at, try yourself to come up a couple levels. If, by the way, if you go eight rungs…”

“if you tell me what you recommend, it forces you to think about an issue. And I get to see the quality of your thinking. And even up front, even a very experienced person may have a five out of 10 hit rate with like, I would do the same thing. But then it creates an actual interesting conversation.”

“And so by task, you could have a very senior person who actually has never done a certain thing inside the organization. And if you don't create, if you're not aware of their task relevant maturity, Then you're going to end up either managing them too far or too close.”

“Oftentimes where delegation breaks down is like, you're either flying too low. The person is as at the, Hey, I know what to do next. Stop Telling me what to do, all these specific things. That's micro. Or it's the flip, which is like, they need various prescriptive instructions, and you're like, oh yeah, just tell me…”

“every company has values, whether stated or unstated or whether lived or unlived, right? It's whatever people get paid, promoted, hired, fired based on, like, it's how those decisions are made.”

“I mean, look, I think, uh, you know, like anything, it's funny, you just don't think about it, but, like, you should have diverse banking partners. Yep. You know, have, like, even we were, we were in the middle, like, of trying to figure out how to do this with the private equity guys and the, and the tenuity, the…”

“One of my frameworks I like is the I, the we, the it, like, what does this mean for me? What does this mean for my team? And what does it mean for the company? Like the group, like the whole thing. And so like being able to very clearly dispel what that means.”

“And so like one of the most common human thing is to collapse that future state in today and be mad that you don't have it. Right. And it's like, well, why don't I know how to lift bench press, 300 pounds yet? That's like, well, you just, you're at one 50, like you haven't done the work to get to 300, you know, like,…”

“for anyone of us coaching someone, I would say, here's what I believe, here's why, here's what I'm gonna do to validate it, and here's what would change my mind, if, and, you know, I'll keep you, I'll keep you abreast, so now, again, someone goes, oh, this person has a point of view, they've thought deeply about the…”

“lesson number one of selling your company. It ain't your company anymore.”

“one thing that just happens in businesses as your business gets bigger, investors pay a higher multiple. It's more stable. It's demonstrated more sort of staying power. And so what a lot of these private equity firms do, and we were sort of a part of this arbitrage was, Hey, I can pay you, you know, X multiple. I can…”

“Once you have a real written offer in your hand from a serious party or a few, right. Then, then you, the leverage flips very quickly. First you're like getting, get around to fall in love with me. Oh, a few people falling in love with me. Okay. Now I get to pick and I can call the other parties and go, here's the…”

“And so I think the core of self limiting beliefs are actually in my, my opinion, the upper limit problem.”

“Imagine you were spending millions or tens of millions or hundreds of millions of dollars to buy a business. What would keep you up at night? Just think that's what you got to put yourself in the shoes of the acquirer. And that's what a lot of the legal stuff is about. Are you telling me the truth? Will you promise…”

“I think it's one of the most unseen roles in any kind of success like this, um, and I'm, even now, we're still unpacking sort of, you know, my appreciation, gratitude, the things I, I didn't even know I, Know I was feeling or know that I needed, that I was getting, uh, from that”