Founders - #408 How to Make a Few MORE Billion Dollars: Brad Jacobs

Episode Date: December 29, 2025

In 2024 Brad Jacobs wrote the book How to Make a Few Billion Dollars. In the book Brad explains how he built 8 separate billion dollar companies and other lessons from his 40+ year career as an elit...e entrepreneur. In the two years since Brad has made a few MORE billion dollars and so the sequel to his first book is: How to Make a Few MORE Billion Dollars. In this episode I share some of Brad's ideas on raising tons of money (Brad has raised over $50 billion), mastering his integration playbook, ideas for organizational integration, org chart design, and how Brad keeps his mind centered and in a positive place to handle the inevitable ups and downs of building great companies. Episode sponsors: ⁠ Ramp⁠⁠⁠⁠⁠⁠⁠ gives you everything you need to control spend, watch your costs, and optimize your financial operations —all on a single platform. Make history's greatest entrepreneurs proud ⁠⁠⁠by going to Ramp and learning how they can help your business control your costs and save time and money.⁠⁠⁠ ⁠⁠⁠⁠https://ramp.com Automate compliance, security, and trust with Vanta.⁠ ⁠⁠⁠Vanta helps you win trust, close deals, and stay secure—faster and with less effort⁠⁠⁠⁠. ⁠⁠⁠Find out how increased security leads to more customers by going to Vanta⁠⁠⁠. Tell them David from Founders sent you and you'll get $1000 off. https://vanta.com/founders⁠⁠⁠ Collateral⁠⁠ transforms your complex ideas into compelling narratives. Collateral crafts institutional grade marketing collateral for private equity, private credit, real estate, venture capital, family offices, hedge funds, oil & gas companies, and all kinds of corporations. Storytelling is one of the highest forms of leverage and you should invest heavily in it. You can do that by going to ⁠⁠https://collateral.com

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Starting point is 00:00:00 Two years ago, Brad Jacobs wrote a book called How to Make a Few Billion Dollars. I covered it all the way back on episode 335. In the two years since the book has come out, Brad has made a few more billion dollars. So his new book has the appropriate title of How to Make a Few More Billion Dollars. Brad was kind enough to send me an early copy of the book so I could read it and do an episode on it. So I want to jump right in the introduction. In the introduction, he talks about why he wrote this book.
Starting point is 00:00:27 He said after the first book, I started getting ink. from people on topics that I didn't cover enough are at all. This sequel provides answers to those questions. And he states why he would be qualified to write such a book. He says, I start companies from scratch, assemble teams capable of extraordinary success and turn abstract ideas into billions of dollars of tangible value. But this is my favorite thing about Brad is how much he talks about managing his mind and how over his nearly five-decade career, he has learned the tools to turn an imperfect mind
Starting point is 00:00:59 into a mind capable of building billions of dollars of value. And so he says, but I'm far from perfect. Psychologist Albert Ellis nailed it when he said, we're all valuable, fucked up human beings. Will count me among them. And so in the introduction, there's a series of what I would call like stand alone ideas from Brad. I just made a list and I just want to share some of those with you.
Starting point is 00:01:21 First, this is great description of just the magic of company building. So he says, for me, creating shareholder value isn't just financial. It's about bringing something extraordinary into. existence from absolutely nothing. Imagine this. One moment, you've got an idea. And before you know it, you're looking at 150,000 employees, billions in profit, and a soaring stock price on the New York Stock Exchange. It is the ultimate feat of business alchemy. Another standalone idea from the introduction, he says this is a very crucial thing. You've got to think extraordinarily big from day one. Nobody achieves massive success by thinking small and hoping to become big. And then the next
Starting point is 00:01:59 idea is the one that I've personally benefited the most. I've spent a bunch of time with Brad. Not only did I read his first book, I got invited to have breakfast at his house. I've recorded a new conversation for my new show with Brad Jacobs. That was actually shot and filmed at his house. If you haven't seen that, just search my name, David Senra and whatever podcast player you're listening to. And you can watch our two-hour conversation. And I've also spent time with Brad since then at a few events. And the biggest change for me was rearranging my, I say, inner monologue into a much more positive mindset. One of my favorite lines in his first book is so much of success in business comes from
Starting point is 00:02:38 keeping your head in a good place. So in this book, this is what he says. And I'll explain how he helped me change the way I think, literally, the way I think, literally. A proper mindset is essential. The ability to rearrange your brain and create that mindset is entirely within your grass. And so Brad has slowly had an influence on me. One time we were at a friend's mutual birthday party in Miami.
Starting point is 00:02:59 I was talking to Apollo Ono. Apollo is the most decorated Winter Olympian of all time. And Apollo listens to a bunch of episodes of founders, and he asked me that question. He's like, you know, most of the people that you cover on the podcast, they are extremely driven, but usually that source is because they had a really bad childhood, they had issues with their parents,
Starting point is 00:03:18 they didn't want to be poor anymore. There was some kind of negative fuel source that they then channeled into this extreme drive in persistence and focus. And Apollo asked, he's like, have you ever come across anybody where the fuel source is actually positive? And standing, I don't know, like 20 feet away, I go, hey, you see that guy? I go, do you know who that guy is? And I go, do you know who that guy is? And I pointed Brad and Apollo didn't know who he was. I go, that's Brad Jacobs.
Starting point is 00:03:42 He started eight separate billion-dollar companies. And he has some of the most positive, maybe the most positive, infectious energy of any human I've ever been around. And Brad started out with that. He talks about that in a little bit in this book, but a lot in his first book as well, that he used to just beat himself up. He used to have this, he used to expect perfection, and we didn't reach perfection. His inner monologue was so negative. And one of the things I learned from talking to Brad and observing Brad is like, over time, it's fine if you start out with a negative fuel source.
Starting point is 00:04:12 Most people do. But it is possible to move to a positive or a more generative one. And so over the past few months, it's like, hey, my fuel source isn't, what I wanted to be now is the fact that I love my work. I love reading biographies. I like making podcasts. I'm obsessed with making podcasts. Now I like talking to some of the greatest living entrepreneurs.
Starting point is 00:04:33 So much so that after some of these conversations I have, I can't even sleep. I don't do any drugs, but I have to imagine this is what it feels like when you take ecstasy. I am completely wired. And so what Brad has really influenced me, and it made me a lot, I would say, just nicer to myself. My inner monologues a lot nicer now. It's like I move to a generative source of motivation, where my drive creates more energy, creates more ideas. It creates more momentum the more it is used, where if you have a negative, or even if you have like a goal base, like say, okay, I didn't want to be poor anymore and now I made X amount
Starting point is 00:05:05 of money. It's possible to deplete that fuel source. And the remarkable thing about observing Brad and what I'm working towards too is like the work itself fuels the drive. And so now with a more positive mindset, you actually motivated your motivation is increased by building, by solving problems, by learning new things, by making something better. Could be your individual product that you're making better or your entire company you're making better.
Starting point is 00:05:25 And this generative drive builds on itself where the motivation and the drive compounds over time. And so instead of needing a constant validation of some kind of external, like money, praise, status, something like that, the act of creation itself generates its own feedback loop. I learn that from Brad. And again, I'm not perfect. I still, if I make a mistake or if I listen to a past podcast and I didn't like what I did, I can still critique myself and be kind of mean, but it is way more generative. And I'm actually shocked at how fast that changed.
Starting point is 00:05:53 So in this book, he's going to talk a lot about his actually, like the way he builds his company, the way he raises money, the way he integrates his acquisitions, how he designs his organizations. But just like the first book, I think some of the most valuable chapters are actually on how he has improved his mind over time. So back to the introduction, he says, there's always something urgent happening. When you're trying to build a giant company, there's always problems popping up. He says, I channel that pressure into a relentless drive.
Starting point is 00:06:21 One of my favorite stories I've ever heard, and that came to mind when I read this. It comes from Herb Keller, who's the founder of Southwest Airlines, who's the most successful airline ever created. I think they were profitable for 40 straight years. And he was asked one time, how do you handle stress? He says, I don't handle the stress. I like it. And so Brad says something very similar here.
Starting point is 00:06:39 I'm comfortable with a little bit of anxiety, even fear, when facing a decision that his huge consequences, because I believe that's a healthy trait in her leader. And then another piece of advice, you've got to love what you do. I love being a CEO. I get up early and work seven days a week. If there were eight days in a week, I'd happily work another day. It is a blast.
Starting point is 00:06:59 And then the last thing from the introduction before. I want to go to chapter four. I'm going to jump around. I really view Brad's books as reference manuals. You can keep the book on your desk. You don't have to read in chronological order if you don't want to. Go to the table contents, see whatever subject matter pops out at you and what's most important where you are in your career at that point and read that chapter. And so the first chapter I want to get into a chapter four, which is raising tons of money.
Starting point is 00:07:22 But before we get there, says a lot of this comes down to striving for clarity and reducing my own bias. And so before we get into chapter four, raising tons of money, I'm going to tell you about the presenting sponsor of this podcast. And that is Ramp. I've seen Brad Jacobs up close. He is personally involved in every step of the process as he builds these companies. Brad loves details. That is something that Brad has in common with. lot of history's greatest founders. They know their business from A to Z and their costs down to
Starting point is 00:07:53 the penny. And Ramp makes doing this effortless. Ramp gives you easy to use corporate cards for your entire team, automated expense reporting, bill payments, accounting, and cost control. And they do this all on a single platform. Ramp's corporate cards are fully programmable. You can set limits so the spending your team never gets out a hand. Most companies only find out about excessive spending after the fact. With Ramp, you can stop it before it happens. The chief accounting officer of Notion just said this about RAMP. Ramp is the only vendor that can service all of our employees across the globe in one unified system. They handle multiple currency seamlessly, integrate with all of our accounting systems, and thanks to their customizable card and
Starting point is 00:08:29 policy controls were compliant worldwide. Matt Paulson, who's the founder of Merkaby, recently switched to Ramp, and this is what he said about it. Ramp is the best. The amount of money you will save from unwanted renewals and employees who think company credit card equals buy whatever you want will far exceed the best credit card rewards program. Matt told me that Ramp has helped him save $420,000 a month. Take the time and set up a demo of the product, and you will see why many of the world's top founders are running their company on Ramp.
Starting point is 00:08:57 Go to ramp.com to learn how they can help your business today. That is ramp.com. Okay, so let's jump into the chapter where Brad outlines all the different ways that he's raised money. He says I'm a big fan of capital markets. My teams and I have utilized them to fuel our growth strategies for decades.
Starting point is 00:09:12 We've raised about $50 billion in total capital to fund M&A and organic growth. We've worked with every investor category. Ultra high net worth family offices, private equity funds, sovereign wealth funds, pension plans, university endowments, long only mutual funds, retail investors, passive ETFs, and hedge funds as well as my own friends and family. There are pros and cons to raising money from each of these investor types.
Starting point is 00:09:37 I will lay out how I think about sourcing capital and how to stay aligned with your major investors once they're on board. So I just want to pull out a couple of the different types of investors that he's raised money from and how he thinks about them. Before we get there, he talks about being a massive fan of running public companies. I like running publicly traded companies. Being public makes it easier to build something big and lasting. It gives me deep access to capital markets on non-ownerous terms. No coupons, no covenants, and usually no board seats. In a matter of days or even hours, my team and I can raise hundreds of millions or even billions of dollars. There are more
Starting point is 00:10:13 advantages to being a public company and just funding. For one thing, it keeps your management team sharp. Every 90 days, the quarterly earnings release is a public report card for all to see. We share our perspectives on the quarter and analysts model our decisions in real time poking holes in those results. That's fair. Results that repeatedly hit or exceed the mark can earn a higher valuation multiple. So investors naturally want to know what's driving those numbers. Being public is also a free form of marketing. I've had acquisitions come to the table because someone saw our earnings report or read a note from a sell side analyst. Now, this is wild. Brad, Brad, sent me an early copy of his book. He didn't tell me that he wrote about founders' podcasts in that
Starting point is 00:10:53 book. And so this is what he said, which is a true story, by the way. While most of the investors in QXO are repeat investors from my previous companies, two of our current top 20 shareholders had never heard of me until I was profiled by David Senra on his founder's podcast, Brad, inadvertently. There's two people in the audience that didn't know who Brad was when I covered his book the first time, heard the episode, decided to look into this Brad Jacobs character and have since invested $750 million into Brad's company. My friend John Coogan says that is the greatest podcast endorsement of all time. Brad put me in the book and that was really cool. The elevated profile that comes with being a public company is not all sunshine and roses though. It also requires thick skin,
Starting point is 00:11:36 which Brad definitely has. No matter how well a company performs against Outlook, there will be loud doubters in the wings telling the world why they think the stock is overvalued. I'm comfortable with that trade-off. So then he gives you advice. Your dilution should be strategic. Trading equity for capital sounds like pure upside until you realize you're selling off chunks of your company. New shares issues dilute the ownership percentage held by existing shareholders. You're essentially trading ownership for fuel. And if you don't think through the math carefully enough, you can end up giving away too much for too little. So the first source of equity that I want to talk about, he talks about family offices over the last 20 years. A new class of investors has emerged. The offices that
Starting point is 00:12:15 manage the money of the world's wealthiest families. Family offices are often the first outside capital source that I will approach. The good ones are thoughtful, patient, and entrepreneurial. Unlike other institutional investors, family offices are usually not burdened by rigid investment mandates when making decisions. If they believe in a venture, they can move fast. Another advantage of family offices is that they're sometimes run by former operators or investors with real world know-how about building businesses. They understand The Grind. I have talked to a bunch of founders about this. Almost without exception, they said they would rather raise money from a fellow entrepreneur's family office than a professional VC fund. Family offices
Starting point is 00:12:58 can offer strategic guidance and access to their network. In some cases, the warm intro into a strategic customer or ideal executive candidate can be more valuable than the capital itself. Then Brad talks about private equity. Each of these, he breaks down, you know, you can read them each in a few paragraphs. Obviously, I highly recommend buying the book. And don't worry if you didn't read the first book because what's cool about this book, there's like a 30 or 40 page summary of Brad's first book at the end of this book, too. So Brad does not sound like he is a fan of taking money from private equity. He says, I generally avoid taking money from them. However, I've made four exceptions, and all four have turned out very well. In general, though, I would advise against using private equity
Starting point is 00:13:38 funds if you have the luxury to do so. As a group, they're entrepreneurial, but can be fair whether friends and their focus on self-interest can favor aggressive decision-making. That said, if you have an early-stage company and need to raise a lot of money, private equity firms can be ready-check writers. The next category he talks about is sovereign wealth funds. These funds are some of the best investors on the planet, but they're not easy to land. They're serious and professional investors, and they think in decades, not quarters. They also come with global networks and huge influence.
Starting point is 00:14:08 The downside is that they take a long time. You have to start cementing the relationship brick by brick long before you need the capital. Before they invest, they'll perform 360-degree due diligence, not just on your numbers, but on how you think, how you lead, and whether you're the kind of person they want to partner with. Their backing can unlock opportunities you could never realize on your own. The next category is pension plans. Pension plans are excellent sources of capital when you're looking for big checks and low drama. They're not after board seats or special terms.
Starting point is 00:14:35 What they want are predictable returns over long horizons, which makes them a strong match for business models, like mine, that deliver value by compounding returns over time. Pension plans are not speedy investors. Decisions typically have to be passed through consultants and layered approval chains of investment committees, board members and trustees. It's a very methodical risk evaluation process and the money doesn't move until every box is checked. But when they commit, their capital is sticky.
Starting point is 00:15:01 They don't freak out during short-term market fluctuations. That kind of consistency is worth the slower ramp up. And then Brad talks about long only fun. funds. When your publicly traded company reaches a certain scale, significant daily trading volume, real revenue and earnings, and a substantial organization, you'll start to get attention from long-only institutional investors. There are two catches. First, most long-only funds only invest in large, well-established companies. And second, their investment attention span has come to resemble that of a hedge fund. 30 years ago, long-only funds would buy my company's
Starting point is 00:15:32 stock and hold it for a decade. Today, some might hold it, but they're just as likely to sell it in a few months. That's a long maybe in my estimation. Nevertheless, you're going to need good relationships with the major long-only players because they're probably going to be your second largest source of capital eventually after index funds. Then he talks about retail investors. Retail investors are often overlooked, but they can be a powerful part of your shareholder base once your company is public. Retail investors have their own advantageous trade. They talk. They post on Reddit. They share on X and they swap ideas in group chats and forums. If they're excited about a stock, they'll become online crusaders for your company. All that positive exposure can create
Starting point is 00:16:11 value because it shapes perceptions about your company and reaches existing and prospective investors, customers, and talent. And then he gives a cautionary tale on hedge funds. He says, this one, I learned the hard way. Hedge funds will tell you they're long-term investors and go on about alignment and conviction. But in my experience, most of them flip the stock as soon as the share price goes up. My team and I put together some pipes to raise money for QXO. Deals I thought were well structured. As soon as they were permitted to, the hedge funds we let in immediately sold out. In fact, one of them sold the stock the day before it was permitted. Hedge funds aren't built for what my companies do. That's not a criticism. They have a business model
Starting point is 00:16:55 and it's not about loyalty or patience. And then he ends the chapter talking about debt. Issuing debt is a powerful tool for a public company. Unlike equity, it does not dilute existing shareholders because no new shares are created. The interest paid on debt is often tax deductible, making a very efficient way to raise capital. Also, because debt must be repaid, it forces a company to be disciplined with its finances. With that said, he says he usually targets a debt leverage ratio of about 1x to 3x EBITA. I'd rather be slightly under-optimized on leverage and sleep at night than live quarter to quarter hoping nothing implodes. And then he's got two great standalone sentences here, the first one. The best investors don't just write checks.
Starting point is 00:17:34 they open doors and sharpen your strategy. The second one, which is my favorite sentence in the entire book, the most consequential decision you'll make in business and in life is who you surround yourself with. The very last sentence in this chapter is a great summary of Brad's prona view on this. Above all, remember that when someone wires money into your company account, they're trusting you to turn it into substantially more. You own that expectation.
Starting point is 00:17:58 Okay, so let's move on to chapter five, which is mastering the integration playbook. He says most acquisitions do not. create shareholder value. There are probably only a few dozen CEOs who are truly knowledgeable about all the ingredients to make an acquisition successful. This is important because if you're not substantially improving the companies you buy, you're just moving capital around. As an industry consolidator, I stake my reputation on my ability to transform separate entities into a cohesive profit machine through integration. If I focus solely on buying businesses and neglected to integrate them well, my companies would be a shamble of local branches with old branding, tech silos, and
Starting point is 00:18:35 teams that don't talk to each other. Operations that are left to linger for months or years under legacy structures limit their profit opportunities, yet this happens all the time. When we complete an acquisition, the very first step is simple but crucial. Ask questions and listen closely. In every acquisition, we ask what's working well and what could work better. The answers often come from the front lines where employees who have never been asked for their input reveal precisely what's working and what's broken. That is where we start with respect for the wisdom already within the organization. For most acquirers, integration begins the day a deal officially closes. But for my companies, that's too late. I do something unusual. I negotiate explicitly for unrestricted access
Starting point is 00:19:21 to the company from the moment we sign an agreement. Immediate access to employees is an essential condition for us. This is not commonplace in M&A. And so then he talks about how he does this. He says, we hold town halls and team meetings and visit field operations. I conduct face-to-face interviews with the top executives of the entity we're acquiring. So he wants to integrate right away. He says regarding the timing of this process, I generally take the Band-Aid approach and rip it off because I found the pros vastly outweigh the cons. Sure, there could be some kerfuffles when we do an integration quickly, but the sooner we get the operation running on our systems, the better. The same goes for business intelligence and dashboards. Our dashboards, our dashboards,
Starting point is 00:19:57 display performance data in a graphical way to erase the barriers between levels of financial and operational sophistication. Everyone gets the same point without big swings and interpretation. And he gives an example from his recent past. When QXO closed on the Beacon Building's products deal, we sent out a Zoom town hall invite to everyone with a beacon email address within minutes of the press release going live. I was happy that 3,600 people, the overwhelming majority of those invited showed up on three hours notice. Instead of lecturing about ourselves from on high, I gave a brief introduction and moved right into Q&A. It's essential to give new employees an open mic to share what's on their minds. And we respond just as openly. This starts
Starting point is 00:20:38 to create an environment of trust. And so something he'll repeat over and over again is that an acquisition comes with talented employees full of untapped ideas. You should ask them what they do to make what they would do to make the business better. It's not rocket science. He says, the town halls we run are far from polished presentations. In fact, being too slick can be a mistake. I make a point of being accessible, answering questions candidly without pre-screening them. And so there's a bunch of list of sample questions that he uses in the book. Here's a few of them.
Starting point is 00:21:09 What are we doing that should be stopped immediately? Where are we over-investing in this business? Where are we under-investing in this business? What are we doing that annoys our customers? What are we doing that delights our customers? Are we prioritizing the products and services that our customers value most? What are the biggest causes of waste or inefficiency in our operations? Does your compensation structure incentivize you to keep doing better?
Starting point is 00:21:35 Are we making decisions fast enough? Are we too bureaucratic? And then these answers to these questions, Brad says, this is when inherited issues usually come to light. We come away with a list of targeted actions that matter to our employees. These get turned into work streams with named owners who are accountable for the deliverables. I am eager to meet anyone who interacts with a customer, either in sales or support. I ask questions, scribble down notes, and always end by extending an invitation to email me directly.
Starting point is 00:22:02 This is well worth my time. Brad is also huge on employee surveys. He says quarterly all employee surveys are one of my absolute favorite tools for running a business. We also sent a version of this survey immediately after we buy a business. It sets a respectful tone and communicates an important message that we want to hear the truth so we can act on it. And then the important thing about the way you do these employee service, all you have to do is just ask three questions. We keep it simple with three questions derived from a longer list. Number one, what's working really well? Number two, what needs fixing? And number three, what's your single best idea to improve the company? As a result, we end up with a set of clearly defined
Starting point is 00:22:44 prioritizations, milestone targets, and end goals. It keeps everyone focused on the thing that moves the needle. And then he also talks about how he does these integrations. One of the most important things is he always has a person that is responsible for every single line item. And he calls this a throat to choke. A single integration can have thousands of specific line items. Each one is assigned a single throat to choke, an owner who is personally accountable for the outcome on a firm completion date. I want to jump to the next chapter, which is called organizational integration.
Starting point is 00:23:22 And so Brad says the first question to answer in organizational design is, how is this business we're acquiring going to create value? I will start with the organizational chart. The blueprint for well-run companies. Over the years, I've reviewed thousands of organizational charts, some elegant and efficient, others chaotic. I've found that the org chart is often a good indicator of a company's focus. Get the people part right and it can become your greatest competitive event. get it wrong and you'll spend years untangling dysfunction and losing money and so he goes into designing the optimal organizational chart when it's done properly someone from outside the
Starting point is 00:23:58 company can look at the chart and immediately understand how the company is structured some people do crossword puzzles i do org charts and he talks about some of them are so confusing he says these are incoherent and bloated because no one's ever stopped to ask what is the optimal organizational architecture to accomplish our goals for good org chart design at the heart of that design is this question. Where should decision-making and P&L authority sit? The answer always guides to a role, not a person. Always keep it simple.
Starting point is 00:24:32 If it looks like a bowl of spaghetti, it probably runs like one. A great org chart should fit on a single page, a clean, geometric structure with minimal dotted lines and no asterix. Brad has a great line from his first book where he says, empty seat is less damaging than a poor fit. And so he talks a little bit about that here. It takes commitment to let an org chart seat stay open until the ideal person is found. An empty slot is far less risky than filling it with the wrong person.
Starting point is 00:25:03 My company's org charts reflect what we want the organization to be, not what we've been handed to work with. We never compromise the structure to check a box and we'll hire from outside the company if we need to. If I look at a business to see a Frankenstein orch chart, an amalgamation of charts from prior M&A, it tells me that each leader has been allowed to keep their fiefdom intact to the detriment of the whole. We take a fresh look at every position and categorize it as a must have, a nice to have, or what the hell. And we're diligent about taking a broom to that third category. The nice to have category is a larger cost reduction opportunity than either of the other two. So by keeping the most promising nice to haves and saying goodbye to the rest, we can optimize the headcount. And so he has some funny examples of these org charts, the thousands of orchards that he's seen.
Starting point is 00:26:00 He says, I've seen companies where someone manages, and he put that in quotation marks, someone manages one person. That's not management. That's companionship. And it pains me to think shareholders are paying for it. You want to eliminate as many layers as possibly. He says layers are the number of rungs between the person on the front line and the CEO. Every layer slows down communication and decision making. The goal is to flatten the org structure, not to the point where no one knows who's in charge, but flat enough so ideas move fast.
Starting point is 00:26:31 I've seen org charts where there are nine layers between the customer and the CEO. That's bureaucracy. The shorter and more direct the line from problem to decision, the better. And he says most of the acquisitions that he does, the cuts don't come from the front lines of people actually serving the customer. It comes from bloated management. So he talks about he had a very wise chief operating officer, this guy named Waylon Hicks. And he says, Waylon Hicks was fond of saying that a fish rots from the head.
Starting point is 00:27:00 Meaning if your leaders aren't top tier, their bad characteristics cascade downward, dragging performance with them. Typically, when we acquire a business, most of the people we exit do not come from the front lines. They're in the mid to upper echelons of the legacy operation. That is where we usually find most of the bloat. A fish rots from the head. Okay, so now I want to go back to the very beginning of the book. I want to touch on the two chapters that are about getting your mind right or how Brad gets his mind right would be more accurate. Before I jump into that, to tell you about two tools that you should be using for your business. The first one is Vanta.
Starting point is 00:27:40 Vanta helps your company prove your secure so more customers will use your product or service. Customer trusts can make or break your business. And the more your business grows, the more complex your security and compliance tools get. That can turn into chaos. And Vanta helps you tame that chaos. You can think of Vanta as you're always on AI-powered security expert who scales with you. Vanta automates compliance, continuously monitors your controls, and gives you a single source of truth for compliance and
Starting point is 00:28:06 risk. So whether you're a fast-growing startup like cursor or an enterprise company like Snowflake, Vanta fits easily into your existing workflows so you can keep growing a company that your customers can trust. Many companies will not sign contracts unless you're certified and that causes you to lose out on sales. That is why the average Vanta customer reports a 526% return on investment after becoming a Vanta customer. Vanta will hope you win trust, close deals, and stay secure faster and with less effort. You go to Vanta.com for slash founders, and you can get $1,000 off. That is vanta.com forward slash founders.
Starting point is 00:28:41 Another valuable service I want to tell you about is collateral. Most companies have a hard time telling their own story. There's a great quote from Don Valentine, who's the founder of Sequoia that illustrates why this is so important. He says the art of storytelling is critically important. Most of the entrepreneurs who come talk to us cannot tell a story. Learning to tell a story is incredibly important because that's how the money works. The money flows as a function of the stories.
Starting point is 00:29:02 And that is exactly what collateral does. collateral transforms your complex ideas into compelling narratives. Collateral crafts institutional-grade marketing collateral, and they do this for private equity, private credit, real estate, venture capital, family offices, hedge funds, oil and gas companies, all kinds of corporations. I have friends that have used collateral for their marketing collateral and have raised billions of dollars of capital and have made hundreds of millions of dollars. I will leave a link down below, but make sure you go to collateral.com
Starting point is 00:29:30 and improve the way your company tells its own story. So the first two chapters of this book are the tools that Brad uses to keep his head in a good place. He says mental clarity is even more vital to your success. Throughout my 46 years as a CEO and entrepreneur, I've discovered that maintaining a clear balanced mindset is essential to strong leadership, not just for good decision making or resilience in the face of challenges, but also because clarity can give you a huge edge. How you manage your inner state can be the determining factor. It is imperative to center your mind. Keeping your head in a good place is crucial for business success.
Starting point is 00:30:04 So before creating anything of value, I first need to get myself centered. And so he starts with two quotes from Lao Zhu, the famous Chinese philosopher. And he says two of his most powerful tenets are knowing others as intelligence, knowing yourself is true wisdom. And the second one is mastering others
Starting point is 00:30:19 as strength, mastering yourself as true power. From the 6th century BC to today, the philosophy behind those words hold true. Our success flows from inner control. I'm an advocate for what I call rearranging the brain. Consciously reshaping thought patterns, perceptions, and emotions to access more expansive ways of being. Mind transformation techniques take continuous practice and a genuine heart and soul commitment. I've dedicated this first chapter to detailing my personal meditation
Starting point is 00:30:49 practices. To be clear, I'm not a meditation teacher or a guru. I'm a fellow explorer who meditates twice a day every day to chill out and stay centered. And so he says, I began transcendental meditation TM when I was 16 years old. I started practicing meditation twice a day. I've been doing that for decades without missing a single day. Meditation is a tool for sharper decisions and bolder visions, not just relaxation. Meditation for me is not about replicating a particular experience. It's about profoundly letting go. And then he describes one of the techniques he uses. Two times that I've been with Brad, he's done this, he's actually done this in front of me and led the other people we're with into this practice. He goes into a lot more detail in the book, but here's the
Starting point is 00:31:33 high level. He says I do a technique based on Queen Gong practice where I open my hands outward, close my eyes and think, I am in the universe. I let myself become a mind without a body floating in a vast, mostly empty space. It is a very liberating feeling. Then I'll bring my arms inward and think and the universe is in me. I will think I love the universe and the universe loves me. It puts me into a completely different state of awareness, one that helps me enter a blissful frame of mind. It also stimulates creativity. And it reminds me of the gigantic context that informs all of our lives, which helps keep things in perspective in business. I think that's the most important sentence. When the inevitable problems of the day hit, they seem small by
Starting point is 00:32:21 comparison. And so he uses a combination of about five techniques. He says, your best ideas will not come from thinking harder, but from thinking in different ways. More often than not, I'm practicing mindful meditation, which is like watching a movie. I'm not the director, the producer, or even an actor. I am simply the audience. Anything can happen in that movie, and I do not resist it. Meditation in all its forms is more than just a concept. It helps keep you in the zone with your head in a good place and gives you the skills
Starting point is 00:32:49 to think differently while maintaining an inner peace. Consider the techniques I describe in terms of the benefits they deliver. positivity, the headspace to think expansively, relaxation and rejuvenation amid chaos, and the ability to keep problems in context. This produces boundless creativity and the capacity to be inspired. In high-stakes business situations, emotional balance is a powerful advantage. And that moves into the second chapter, which is making your way back to center. What happens when you're knocked off balance?
Starting point is 00:33:21 In any endeavor, it is important to keep the ups and downs into perspective, especially the downs, spoken like an entrepreneur with over four decades of experience. Losing your center is not a failure, and perfection is impossible. I know that our brilliantly flawed universe will inevitably generate some outcomes I do not like. Not only am I okay with that, I also recognize that good things can come from those outcomes. Or at the very least, I can learn from them. When I stopped expecting flawlessness from myself and others, this is something he also talks about in the first book. that really resonate with me.
Starting point is 00:33:56 When I stopped expecting flawlessness for myself and others, I could let go of frustration and put that energy to good use. I believe in this imperfection mindset so strongly that I've woven it into the culture of each new company I start. Mistakes are not failures. They're the very substance of our growth. And one thing that Brad does is really good at zooming out and trying to put everything into its proper context.
Starting point is 00:34:19 So he's like, well, how did these human traits that we deal with now, how do they evolve, and do they make any sense in our modern environment? So he talks about this right now with the fight or flight response. He really likes to zoom out. Take the fight or flight response. For our more skittish ancestors
Starting point is 00:34:35 catastrophizing harmless rustles in the bushes gave them a survival edge over those who ignored potential threats. Their vigilance was passed down. Today, that same wiring can leave us anxious in safe environments. We pump adrenaline, our hearts race, we sweat.
Starting point is 00:34:50 Prolonged, it can zap our energy. heightened tension and leave us caught in cycles of worry. Anxiety and pessimism, once vital to avoiding danger, now often manifest as excessive risk avoidance. As a serial CEO, I couldn't have built global public companies without embracing calculated risk. Evolution reminds me that these feelings are echoes of the past, not accurate guides for contemporary decisions.
Starting point is 00:35:17 When we recognize these inherited tendencies for what they are, outdated survival strategies we give ourselves the power to step out of their grip evolution explains why anxiety and self-criticism show up so strongly but it doesn't dictate how we respond to external events today so then he gets into some of these tools that he's found very helpful the first one is rational emotive behavioral therapy r ebt brad likes the work of albert ellis talks about some of the ways that ellis would help people get back to center So he talks about this group environment. They're talking about, you know, people would share something that was making them angry, anxious, or depressed, something that was knocking them off center. And so as Ellis would then ask the person to close their eyes and get in tune with that negative emotion. When he felt they were ready, he'd say, okay, now make yourself half as upset as you just were. They would sit in silence for a minute or two why they do this.
Starting point is 00:36:10 And essentially, he says Ellis was demonstrating that external events in and of themselves do not make you upset. What makes you upset is what you tell yourself. In my experience, most people carry on an intermittent internal monologue of self-criticism. It's a quiet, often unspoken commentary, invasive, persistent, and deeply personal. Nearly everyone I know underestimates their own worth. This is what Ellis referred to as stinking thinking. Ellis's work profoundly reshape my understanding of perfectionism. I used to hold myself to punishingly high standards, demanding constant.
Starting point is 00:36:48 and excellence and leaving no margin for error. Unsurprisingly, this only led to disappointment. Ellis taught me to reframe rigid demands as flexible preferences to aim high but not crumble if I fell short. By embracing the inevitability of human error, I discovered a more resilient mindset and a far healthier foundation for both my business endeavors and my personal relationships. Through his REBT, Ellis helped millions of people confront and reshape their irrational, self-defeating beliefs the core of his therapy is to identify those beliefs
Starting point is 00:37:22 and reframe them into more rational ones and so he's a bunch of lists of examples of this so like your rational belief would be I must be liked by everyone to feel good about myself well you need to reframe that
Starting point is 00:37:34 into a rational belief that would sound something like I prefer to be liked but I can still value myself even if some people don't like me and he lists like 17 of them I'll just give you some other examples irrational belief
Starting point is 00:37:43 others must treat me fairly are there awful people reframe that to a rational belief. It's preferable when others treat me fairly, but I can't control their behaviors only my response. Irrational belief. I should never feel anxious, sad, or angry. Rational belief. Emotions are natural and they serve a purpose. Irrational belief. I must take responsibility for other people's problems. Rational belief. I can be supportive, but I'm not responsible for fixing everything for everybody. Irrational belief. If I feel it, it must be true. Rational belief. While
Starting point is 00:38:11 my emotions are important, they don't always reflect the full truth. I can challenge my feelings with evidence. And so then Brad at the end of the section says, when I find myself out of the zone, when I find myself off center, I try to pay attention to what I've been telling myself that made me upset and I reframe it in a more constructive, rational way, literally saying it to himself in a better way. I find this extremely effective. The second tool that he talks about a lot is cognitive behavioral therapy, CBT. It is widely considered to be the gold standard for helping people free themselves of problematic thought patterns, learn behaviors, and core beliefs. And so Brad writes, what I learned from CBT is that we're all born with
Starting point is 00:38:49 schemas. Schemes are cognitive frameworks to shape how we interpret the world. Core beliefs are part of schemas. So are behaviors and emotions which are often developed during childhood. These schemas act as prisms through which a person interacts with life. Over time, this can lead to cognitive distortions in how a person thinks, especially when the schemas are rigid and over-filtering are negative to begin with. When I'm out of the zone, it's usually because I'm upset, anxious, sad, or angry about something. There are a couple of ways
Starting point is 00:39:21 I can approach this. I might use Albert Ellis's method and ask, what am I telling myself right now? What is my irrational belief that I need to reframe? Irrational and distorted thoughts must be reframed in a constructive way to engage with life more validly and happily. The
Starting point is 00:39:37 way you think affects the way you feel. CBT taught me how my interpretation of a situation, through automatic thoughts can skew my emotions and behaviors. It also gave me an incentive to consciously question my negative thoughts. And so previously he had examples of irrational belief, rational belief. This time, he has distorted thought, reframed thought. And a lot of this has to do this negative internal monologue, so distorted thought. I mess this up. I always screw things up. Reframed thought. This one
Starting point is 00:40:07 didn't go as planned, but I've done well before and I can learn from this. Distorted thought. I feel like a failure, so I must be one. Reframed thought. Feelings aren't facts. just because I feel this way doesn't mean it's true. Distorted thought. They said I did a great job, but they were just being nice. Reframed thought. They didn't have to say anything at all. Maybe I really did do a good job.
Starting point is 00:40:25 And so he gives a bunch of other examples in the book. The next tactic that he uses is dialectical behavior therapy. And this section is really short. A dialectical approach means viewing something from multiple perspectives and interpreting it in different ways that were all valid. The fourth tool that he uses is positive psychology. This is also very short. The fourth technique in my re-centering toolbox is positive psychology.
Starting point is 00:40:48 Instead of asking what's wrong, it asks what's right and how can we build on it. And the fifth and final one is mindfulness. Mindfulness is a powerful and uplifting approach to life. It involves radically accepting yourself, others in the world, non-judgmentally and unconditionally, without trying to change a thing. And it requires intentionally paying attention to what's happening in the moment. And he talks about one of his teachers translated mindfulness from the Buddhist monasteries to a secular form. He says his method was elegantly straightforward.
Starting point is 00:41:19 Pay attention to the present moment without judgment and without trying to change it. That is all. By systematically directing the mind to each part of the body and practicing mindful breathing as well as a slow, intentional movement,
Starting point is 00:41:34 this trains the mind to anchor itself in the here and now for mental clarity. Mindfulness is a tool I use for emotional regulation when something is going haywire in an MNA transaction, or I'm dealing with any of the myriad challenges that inevitably land on a CEO's desk, I practice mindfulness to get back into the zone. One of the most powerful things I can do as a business leader
Starting point is 00:41:58 is to be fully mindful of the person I'm with in that moment. It could be a customer, a shareholder, a teammate, a vendor, anyone. When I give a person my complete attention, I'm treating that encounter as something meaningful and that person as someone important. Sometimes I think to myself how fortunate I am to be right here right now with this person or group. So those are the five frameworks in my re-centering toolbox.
Starting point is 00:42:23 If I get thrown off center, I reach for one or more of them, REBT, CBT, DBT, positive psychology, or mindfulness. The techniques overlap and sometimes I mix and match them, but the goal is always the same, to get back to center. It is not about eliminating problems since they're part of the gig but about responding to them intentionally from a grounded
Starting point is 00:42:46 place. I don't pretend to have it all figured out. I slip up sometimes. Like when I catastrophize or catch myself demanding perfection for myself or others, but I pick up on it faster now and I reframe it faster. I return to the zone more smoothly.
Starting point is 00:43:03 No one stays perfectly centered all the time. But knowing how to get back to center will help you navigate the ups and of life and business.

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