He's negotiated $1B+ in executive compensation. Here's his playbook. | Jacob Warwick

00:00:00What's the most common mistake thatpeople make when they're negotiatingtheir comp?>> Often we'll hide behind the easiestcommunication channel possible. I mightemail you my demands. The problem withthat is I can't control tone. If I pushback and the CEO that reads it's in theairport security line and pissed off andthey read it, they might be like, "Thatbastard wants more money.">> A lot of people listening to this arejust afraid to ask for more. I'm goingto come across as greedy. It's all goingto fall apart. But when you look at themoney that the company's making incomparison, like you're not beinggreedy. It doesn't have to be>> such an aggressive thing. It doesn't[music] have to be confrontational. Thesimplest advice "What's the chance therecould be a little more?">> That's not greedy at all.>> The core of your philosophy is make itvery clear to the company here's thepain I will solve for you and here's whyit's worth paying you this much more.>> These companies have significantleverage over you. They know what peoplemake, they know what others make, theyknow what they'll accept. You have tounderstand what value you can create andif you understand that value, you canhave that conversation with confidence.>> Today my guest is Jacob Warwick. Jacobis a professional negotiator. He worksbehind the scenes with his clients,mostly senior tech execs, professionalathletes, and Hollywood celebrities. Andhe helps them navigate their mostcomplex career negotiations,>> [music]>> including their comp, their bonuses, and

00:01:15investments, also M&A and takeovers andenterprise sales deals and more. He'shelped his clients secure over $1billion in additional comp. And he'stold me that he's negotiated against anumber of guests on this [music]podcast. He is very much under theradar, is not on social media, rarelydoes interviews, and in this exclusiveconversation, we get super deep on thespecific [music] tactics and psychologyof comp negotiation, including why youshould never negotiate over email, whoshould speak first when the question ofcomp comes up, the most common andcostly mistakes that people unknowinglymake when they're negotiating comp, andso much more. Jacob is also just a trulystellar human and I'm very excited to besharing his story. Don't forget to checkout Lenny's product-pass.com for anincredible set of deals availableexclusively to Lenny's newslettersubscribers. Let's get into it after ashort word from our wonderful sponsors.This episode is brought to you by Orkes,the company behind open-sourceConductor, the orchestration platformpowering modern enterprise applications.Modern systems are built onmicroservices, APIs, and event-drivenarchitectures, but legacy automationtools can't [music] keep up. Siloedlow-code platforms, outdated processmanagement, and disconnected API toolingbreak down under real-world scale andconstant

00:02:30change. Orkes Conductor [music]provides a production-gradeorchestration layer for coordinatingmicroservices, APIs, data pipelines,human tasks, and agentic [music]workflows with deterministic controlflow, retries, observability, andgovernance. Built for enterprise scale,Orkes supports visual and code-firstdevelopment [music] with built-incompliance and reliability. Through abuilt-in MCP gateway, AI agents handlereasoning and decision-making whilesafely accessing existing APIs [music]and internal systems as MCP tools. Thisenables agents to operate acrossenterprise environments and scale fromdemos to production, orchestratingsystems, agents, and humans together todeliver smarter outcomes faster. Learnmore at orkes.io/lenny.That's orkes.io/lenny.This episode is brought to you byMercury, radically different bankingloved by over 300,000 entrepreneurs,including me. I switched to Mercury fromChase over a year ago, and it is such aprofoundly better experience. It's likean [music] actual product person built abank versus a banking person building aproduct. It is fast, it's elegant, it issuper easy to set wires, to track myspending, [music] to set up triggers, tomove money around when accounts get low.We moved all of our invoicing toMercury, and

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00:04:16Jacob, thank you so much for being here.Welcome to the podcast.>> I'm very happy to be here andthank you for interfering with my sleepall week out of my excitement. Usuallyit's my newborn and toddler, but thistime I was waking up at 3:00 in themorning thinking about and it's going tobe a great chat. So, I'm very excited.Thank you for having me.>> I really appreciate that. It's going tobe worth it. It's going to be worth itmostly to us to to extract all thiswisdom from your head. So, we're goingto be going deep on negotiation. How tobetter negotiate for comp and this willtranslate into all kinds of other waysof in your life beyond comp. This issomething I personally been very, verybad at in my career. Like I don't knowif I like maybe one time I pushed backand negotiateda higher comp, but I just like I'vealways been really nervous to do thisand just really bad at this.And I imagine most listeners are nervousand bad at this. And you do this for aliving. You help people negotiate. WhichI don't think people even know this is athing that exists, that somebody's outthere that can help you negotiate. Andso, you've seen a lot of negotiations upclose.Most of the people you work with just asa context are very senior people, but alot of the stuff we're going to talkabout is going to apply to anyone at anylevel.Let me start with this question just togive people a frame of reference.

00:05:31How much comp are people generallyleaving on the table when they don'teven try to negotiate?>> Yeah, so typically what I've seen iseven without my help, just generalpushbacks, not aggressive, a simple"What's the chance there could be morehere?"kind of pushback. I mean, that's aboutas easy as it can get. You get theoffer, you say, "What's the chancethere's a little bit more?" Almostalways see a 20% improvement on that.And that is across the board fromearlier stage positions. Let's say theygave you a $100,000 offer, 120 could bethere just from a simple push back,which iswhen you're making that kind of money,that's life-changing, right? I'venoticed that when you make amillion-dollar W-2, same push back, 20%,sometimes more, just on the what's thechance, depending on how well you goingto navigate that interview process. Now,on average, when I'm calculating out,what I'm looking for with clients isabout 40% movement on an increase. Wehave seen as much as 100, 200, 300, 400%increases from initial offers.Most notably, breaking salary bands,which we all treat as gospel, which issomething we'll probably talk aboutthrough the course of this this podcasttoday. That uh you know, those thatchallenge authority and challenge in ameaningful

00:06:47and collaborative way willwin more than those that don't. Andwhat's interesting isI found that product product leaders,engineers, designers,uh some of the more tend to be moreintroverted and thoughtful types,negotiate more poorly than the obnoxiousmarketers and revenue leaders and themore extroverted types. And it'sfrustrating because if you look back atthe last, say, 25 years or so,product has really defined the techgeneration in so many ways. This isn'tto discredit marketers or anything likethat. It's just to show that there's acouple of sides of the business and andeveryone tends to negotiate a littledifferently. So, you looking back atyour career and say, you know, the greatLennyhad a tough time pushing back. I thinkthat's that's actually inspiring for alot of the listeners to see thatyou're not alone in feeling this. Itdoesn't have to be such an aggressivething. It doesn't have to beconfrontational. The simplest advicethat I can give you is, what's thechance there could be a little more?>> That's not greedy at all. It's just asimple ask. And even that, 20 30%. Soagain, a lot of people listening to thisare just like afraid to askfor more. There's like uh I'm going tocome across as greedy.

00:08:02Uh I'm going to it's all going to fallapart. They're going to be like, whatare you what are you talking about? No,no, forget it. Or they you know, theyjoin, they get better comp, and thenthey're like uh everyone kind of theyknow that I pushed all this and I'm thiskind of greedy person. Now theexpectations are higher.What do you tell people to help them getpast that and actually negotiate andactually go for it?>> Yeah, a couple things here. So first ofall, usually a company is extractingmuch more value out of you.Naturally, like 5:1, 10:1, 100:1, right?If you'reI know the audience is primarily producthere. I mean, you're developing productsthat haveinfinite scalability in some capacity.>> That's going to make the company a lotof money, and they are a big piece ofthat.>> Andproduct tends to be rewarded fairlywell, right? But when you look at themoney that the company's making incomparison, like you're not beinggreedy. And if you understand that valueexchange,you can have that conversation withconfidence. That's not to say that beinga tall poppy isn't risky. That's theterm. You over negotiate,I would rather my clients overnegotiate, reach a couple rungs up onthe ladder, and they get slapped down.They're still failing forward, andthey're growing in some capacity.Andif you can ideally align work thatdoesn't feel like work, it feels alittle bit more

00:09:17like play with strongcompensation, you don't always need tonegotiate hilariously for the top of theband or break the bands just because youcan, right? This isn't to be greedy.Right? But it's just to understand thatthis value exchange isn't fair for youregardless of how it works. Like thepath to wealth is through ownership,right? And as a W-2 employee, you'rebeing taxed heavily.And it it makes sense to push a littlebit in this context. So, that'stypically where I start. I want you tojust have the confidence to know thatit's okay.>> Let me come at it from the otherdirection. Uh a lot of people listeningto this podcast are founders or hiringmanagers, managers.They may not be super excited to hearwe're giving people advice on how tonegotiate harder for higher comp.What could you say to them to make themfeel a little bit better about ussharing this sort of advice?>> So, I will challenge them as well. Now,IHow important of a priority is toptalent and maintaining and retaining toptalent to you?Right? When you were thinking about howquickly the speed of innovation ishappening. You've had a lot of great AIguests on the channel recently. Right?Like the exponential curve of growth isincreasing.If youhope to stand a chance, you need toattract the top talent.

00:10:33And you need to keep that top talent cuzit's very expensive to replace them.I'm not suggesting that people beat youup for the sake of beating you up.So, this is uha myth about negotiation that'sadversarial.What I teach is how can we be morecollaborative? So, the conversation is,"Look, Lenny, as a founder,can you help me understand what'simportant to you? The value that thiswork will drive." And then naturallywe'll come to terms that make a littlebit more of a value exchange make sensethere. So, often times some of the waysthat we're breaking the boundaries ofcompensation isn't necessarilyadvocating for a busted base comp leveland bonus percentage.Often times we're putting performanceincentives, milestone triggers.If the company grows to 100 million ARRand I contributed this to it,what would that outcome look like? Wouldthat be another tranche of stock orwould that be cash or would that youknow, we'regetting more creative here.And so, what's interesting isfor the longest time I had a I had adifficult time advocating for this. Andhaving been a CEO and founder myself,I understand why you don't want to do itcuz it's hard. It's hard to make this.And everyone also thinks they're toptalent.

00:11:48And when everyone thinks they'retop talent, somebody's got to be lying.Right? It can be difficult to understandthat. So, those that I found are moreconfident to push towardsperformance-basedtend to have more skin in the game. Tendto want to stick around and see thatsuccess happen. Those are the types ofpeople I want working for me if I wantto be a very competitive organization.I have started to have theseconversations with a couple Fortune 500companies as well as some talentconsulting companies, think bigrecruiting firms, where they've broughtme in to advise on the comp committeesso that they can get more creative withtheir structure so they don't losetalent. Because nobody wins when youhire a top performer and they leave in10 months. The recruiting firm losestheir pay, right? Their performance pay.The company now has to go back andreplace that person. It usually costshundreds of thousands. And in some ofthe realms that we navigate in theFortune 500, it will cost millions ifnot tens of millions to replace the lostIP there.So, the argument here is it's okay toget creative. Reward it when you see it,right? I'm not suggesting give everyoneeverything I've been the company and andtotally ruin your business model.But, if you want to be competitive, becompetitive with your pay as well.>> That's

00:13:04a great answer. And we werechatting before we started recordingthis, and you shared that you've helpedpeople negotiate with many of guests onthis podcast, like people that they werehiring, and you helped them get highercomp.>> I won't mention any names.Um some recently were in in the realm of10 million plus on increases incompensation across a a team of just ahandful of folks.Uh again, Fortune 500,um but the alternative was lose them tocompetitors and have the stock dropafter the CEO made announcementspublicly in their earnings calls.And so, they don't knowthatit may have cost them 10 million today,but it saved them 300plus, 300 500 in this business process.So, the success will be there, and Iwould sayalmost anybody would pay 10 to save 300.>> And the way you operate, just so peopleunderstand, is you're very behind thescenes. You work with clients, and youadvise them. You're never involved inthe negotiation. You just give themadvice on how to approach it.>> I would call it fingerprintless, andthere's a reason for this. So, it'sit's not yet popularized. Maybe it willbe with some of these uh in AI ICs andthese hot scientists are pulling down$100 million contracts. Maybe this willchange soon.

00:14:19In Hollywood, you have anagent negotiate on your behalf, and theykind of are serving as that middlemediator.That's not common in the corporatecorporate America right now, right? Now,if that happens, it almost dilutes theleadership and presence of theexecutive.And so, how I work is similar to anattorney, where all correspondence goesthrough me before it goes to the endrecipient. So, let's say that you'regoing to talk to the CEO, you call mefirst. We prepare the game plan, westrategize, you then perform, then wedebrief. Then, the CEO sends you anemail. That email comes to me, we draftit together. I usually test my client'sinstincts first, rather than just doingthe work for them. Test their instincts,polish the language,because every step of the way is anegotiation.Now, this also slows the process down.We want to go slower, and I'm sure we'lltalk a little bit more about that in thepodcast. Too hasty equals risk.So, as you slow down, often times wewant to take a couple of days torespond, not to be a jerk or belligerentor to manufacture some fake urgency, butit shows a little scarcity and thoughtprocess to your time and we get tocalculate and collect

00:15:34informationthrough the process.>> This is so interesting.What What's the most common biggestmistake that people make when they'renegotiating their comp?>> They don't understand when it starts.So, the It starts much sooner than youthink. So,I've I've got myself in hot water withthis before, too, becausealike a LinkedIn profile and your resumeis a snapshot of what you've been in thepast,but it doesn't help you negotiate in theforward.Right? So, if somebody can say, "Oh, I'mlooking at Lenny and I'm looking atproduct manager." If that's all theysaw,they're not going to know all this workthat you're doing in the future ormoving forward and what your vision is,things like that. So, they stamp you asproduct manager Lenny.Right? Now, you're media mogul icon,whatever, right? But there's a gap thatyou have to fill. Right? So, the thingsyou say on LinkedIn serve as aperception.The headshot that you have serves as aperception. I used to joke that I couldscan profiles, I would know how muchmoney someone made by the quality oftheir headshot.And you can seeand it would like it was wildlyconsistent. It was almost frustrating.But anyway, what you're putting out intothe world, the narrative you sharepublicly, starts to become how you'reknown, your reputation.If you arepositioned

00:16:50as a commodity, you will be treated likea commodity.Right?So, often times the less you share isbetter because when you're on the phonewith somebody, you can correct thenarrative and steer the conversationwhere you want it to goversus have to live by the sins of whatyou did 10 years ago as an example. So,the things you share with recruiters,they take notes.When a recruiter calls you and says,"Hey Lenny, how much money do you expectto make?" and you say, "Oh, you know,225. That sounds fair." You know, 5years later, they call you and theyexpect you to make 225 again, notrecognizing that you've grownexponentially since then. So, everythingyou communicate starts to serve as thatvalue chain across the board.Another mistake that people make,and you mentioned this a little earlier,it feels uncomfortableto get quote unquote confrontational orto feel like you're asking for too much.So, often will hide behind the easiestcommunication channel as possible.So, I might email you my demandsdemands, right? Or my negotiation.And the problem with that is I can'tcontrol tone. I can't control,especially when you're negotiating athigh levels,if I push back,

00:18:05and the CEO that reads it's in theairport security line and pissed off andthey read it, they might be like, "Thatbastard wants more money." That's allthey take away. Even if you perfectlyworded it, you got it all, you know, asclean as it can be. If you catch them atthe wrong time, you have no control overhow it's received.Right? So, it's always better to have atleast a video call, if not in person, soyou can share tone, you can read bodylanguage, you can correctevery step of the way.Often times we also try to negotiatethrough recruiters, right? You could dothat like I I Jake I did the thing,Jacob. I talked to a recruiter. I spenta half an hour explaining it. Theproblem with that is you're playing agame of telephone.So, the same thing happens. I I explainit to the recruiter. I get the toneright. The recruiter goes to the CEO andsays,"That bastard wants more money." Andthat's all they communicate, right? So,people negotiate with the wrong folks.You have to go to the one who has skinin the game, who controls the P&L, whocontrols EBITDA. What what's what'stheir motivation? That's who you want totalk to.And so, some people might also have aconcern with well, how I go around therecruiter? I don't want to be look bad.We have to do that respectfully and nowwe need to plan what that communicationlooks like.And so

00:19:20the important thing here is justbecause it's uncomfortable doesn't meanyou don't need to do it. It just meansyou don't know how to do it.So when something's uncomfortable, youhave to run towards that because that'swhere the growth happens.I love how tactical we're getting here.So following this thread, so the advicehere iswhen you get an offer and you want andyou should basically you're saying youshould always negotiate in some way youshould push back. Your advice here isdon't do it over email. Make sure youfind a way to do a video call withessentially the hiring manager or theperson that is has skin in the game thelike the finances and the budget. Thereare situations especially at high levelsmore deals are closed on the golf coursethan they are in a boardroom.Right? So there are situations where youpull someone into a different element.This is called home field advantage.Right? So if you go to a company to havea conversation, you're out of yourelement inin a situation where you may not performyour best.The other thing people don't do is theydon't control the time of which theyhave a conversation. CEO wants to hop onat 6:00 in the morning. Get your ass up,get that presentation and go.You need to say I'm not available atthat time.I'm in and you read your own bodylanguage. I'm strongest between thehours of 10:00 a.m. and and 1:00 p.m. Iwant a meeting in that time. So I willsay I'm

00:20:35unavailable until that timebecomes available.That also communicates scarcity that youwon't get pushed around.Right? So it's scary to do that to saynoto the CEO, I'm actually only availablehere. That also creates a rubber bandeffect that makes you more attractive.Right? And so often times it actuallyopen AI did this which is funny. And Ididn't realize what the reason was, butI had some clients interviewing forC-suite roles at open AI.And so pushing Sam Altman around alittle bit which I'm okay with.I'm okay with that. Umbut so they used to walk outside of theoffice and just walk downtown SanFrancisco instead.Right? You take someone out of theelement, you get the endorphins going,you're walking and talking. You're Theimportant piece here is instead of youand I being confrontational,like negotiating between each other,we're walking walking side by side.So it's almost like you could put yourarm around the other person, you'resolving the problem together. Thesesound like minorthings to consider, but the bodylanguage and the tone and thecollaboration and the energy starts toflow more naturally when you do This isall behavioral psychology, right? And sowhat Funny story, why I found out OpenAIdid that was because they didn't wantany executives going into the officebecause it was such a mess.

00:21:52It was like the biggest startup you'veever seen. So I used to joke that it wasa two midgets in a trench coatpretending to be a real company, right?And uhso anyway, the point was let's take themto a place where we can controland have an advantage over theconversation. So that's the way that youcan think about where are you going tofeel most comfortable? What hours of theday are you most comfortable? If you canbring someone to a lunch or a coffeewhereyou're on even playing field or evenyour home field, you will perform betterin those situations and you have morecontrol over that than you may think.>> So the advice there is try to get thisconversation out of their office.>> It can be, you know, but if I'm aproduct manager and I'm talking to adirector, that may not be possible.Right. Right. They might just say,"Look, you got to come into the office,you got to do this." Right?I'm pushing like when I'm talking abouta C-suite level, like you could pullthem out of the office, "Hey, let's goget drinks." Like sometimes these dealsare closed at 8:30 at night after aconcert or something like that. So it'seasing that situation. That being said,it doesn't mean you couldn't try. It'slike, "Hey, I've got a couple ofquestions. Are you open to, you know,take a walk down AT&T Parkand and have a conversation about it?"You could pull them out of that, you canstart to build a stronger relationshipthrough that and you're more likely toget your way.>> Talk us through this the kind of this

00:23:07the process you would recommend from Iget an offer, recruiter sends me, here'syour offer.300k salary, some kind ofequity.What's kind of like the step-by-step youAnd I know this is depends on the role,seniority, type of company, PE, VC backstartup. Cuz it's very scary to pushback and be like, oh, I want more.UhWhat's like that first email / reply tothat email look like typically? Likewhat are some phrases maybe you'd use?And then what's the How do you open up aconversation where you plan to ask formore if you're meeting in personespecially cuz that feels so scary.>> So first we want to approach withgratitude.Right? We're thankful that we want tomove forward. Right? So, Lenny, Iappreciate you making me an offer,right? I'm excited to work with you. Wewant to show enthusiasm, which alsoshows some confidence.We have to show that the deal is goingto get done even if you're on the fenceabout it.Right? Now, it's not to say you're soexcited that it's a sure thing andyou're not showing that you'redisappointed even if you are.Right? So, I'm grateful. I'm lookingforward to working with you. I want toreview this over the next couple ofdays. Right? Talk to my wife about it.You know, talk to an advisor so and so.Later on when you're a high-levelexecutive, you're talking to legal,you're talking to advisors, you'retalking to a

00:24:22coach. Like you may havefive or six people see that. Right?Employment lawyer, all that. That stuffis expected. Right? So, you're goingthrough the process. I'm going to take acouple days to process this. I'll getback to you. I may have a couple ofquestions.Right? But we'll loop back and itshouldn't be a problem. I imagine westart working together in a coupleweeks.Right? So, the point is you have to sellthat the deal is going to be done.Which helps them feel likeit's going to move forward regardless.Right? So, any ask that you make is notgoing to be egregious.Now,often times, the higher you anchor, thebetter you're going to perform.Which can be frustrating because youdon't necessarily want to be like, "Oh,I increased it 40%." or anything likethat. Now, this is where a lot of nuancecomes in.So, we might say, you know,come back 3 days later, want to have theconversation, let's take a walk in thepark and talk through it, right? Youknow, I've got to be honest with you,where this offer stands right now,I don't feel comfortable moving forward.It's a little lighter than I expected.Right? I may start saying something likethat. And then just waitand see what they have to say.Maybe they say, "Well, what did you havein mind?" It's like, "Well, what's thechance you can sharewhat the range looks like for this andwhat type of performance did you expectfor each of these levels?"Right? Or they may say, "We We

00:25:37compedyou in the middle part of the range."Right? You might say, "What does the topend look like? You know, what what mustI doto fit those needs for you? Can you helpme understand?" Now, for a lot of folks,especially in this market and this if ifwe talk about what it was like in 2021versus what it's like now,there's some over-leveling that'shappened. So, there are people that areC-suite going back to VP and VPs goingback to directors, especially as they goto bigger companies.Often times I'll say, you know, as wehad this conversation, I I'm likely alittle more horsepower than youanticipated.Right? What's the chance we can come inand restructure the comp for the type oftalent we're bringing in here?And so, this is a line that we used. Uhthere were three folks last year thatwere the in ranges of 185 to 285, thatdeal landed at 1.1 million when we weredone. With increases in stock, big cashincreases. Two deals that were comped at600 that landed at 1.1 and 1.2. So,doubled from that. And these weresituations where the role started atsenior director and were up-leveled toVP because they were reaching for toptalent in that situation. So,there are opportunities where it'seasier to steer if you're really, reallygood. Right?

00:26:52I can see why somelisteners are like, "Well, I'm not therein my career yet."In that case, this is just how it getsdone.Right? This is how bigger moves happen.It doesn't mean you can't push for maybe20% more naturally. That I would startwith, what's the chance there's a littlebit more here?I was expecting this, right?Again, more nuances cuz if you open upwhat you're looking for too early in theconversation,that can be difficult to come back fromlater on. It's not entirely egregious,but one of the first things out of arecruiter's mouth is how much money doyou want to make?Which is eerily similar to an illegalquestion, which is how much money do youmake?Right? But if you say, "What do you wantto make?" then it's okay. And that'swhere a lot of people get hung up aswell. I love that phrase you just sharedof"What's What's the chance there's a bitmore here? I was expecting number X." Isthat Is that the phrase you recommend,that approach of just a soft pushbackjust to see?Uh sometimes. Uh again, it reallydepends on the leveling. If you arevery senior,I I typically don't want to re-anchorwith a number because you should neverbe so sure of what you're worth that youwouldn't accept more.>> Mhm.>> Right? And when you anchor, that's

00:28:08theceiling. And what often happens isnaturallythey want to split the difference.And so, I'll have a quick There's aquick Hollywood story here. So,we had a writer who had a $700,000contract.Right? So, 700 and the agent that I wasworking with was was saying like, "Thisuh this writer has the most aggressiveattorneys in LA."Right? They're super aggressive. Uh andI said, "Well, how do you know?"First of all, well, that's what they'reperceived as.So, the production studio offers thiswriter 700. The attorneys come back andsay, "We want 1.3."Right? 1.3 million. And the studio said,"Fine, we'll do a million." And theysettled at a million. And I find thatreally interestingbecausethe studio came up 300,000and the attorneys lost 300,000. So, yousplit the difference right in themiddle. So, if the attorneyssaid 1.5, would the deal have come in at1.1?If the attorney said 1.7, would it havecome in at 1.2? Right? DidHow do we know?The way I see it is those attorneysweren't aggressive enough. We didn'tfind the ceiling there, did we?Like that was lazy negotiating. Right?

00:29:23So, it still made the client 300,000.They were excited, right? The attorneyswere excited. They made more on theircommission. The agency was excited. Theygot 10% of that. But we didn't find theceiling, did we?That was lazy negotiating.Right? So, those are things that you gotto slow down to really understand whereis the value being made here. In thatmovie, like that movie could make 50million dollars. You think a 1 millionfor writing was worth it? Or someone whocontrolled the creative there?I don't know. A 50 to one valueexchange, why not push for more?Why not put some milestones in that ifthis movie makes more than 50 mymilestone is increased. This is how likeTom Brady had his contract at Tampa Bay.Right? Win eight games, get a half amillion dollars. Win 12 games, get amillion five. Go to the playoffs get anextra this. Win the division, get this.Uh get this get to the Super Bowl, X.Win Super Bowl MVP get two and a halfmillion more. Like so, performance-basedtriggers.>> I love just how how much you love this.It's just clear this is so interestingto you.>> it's really nerdy, I know. Like I I'velike obsessed over it in a in a weirdway, but uh I don't know. It's uh it'sbeen kind of baked into my my psyche fora long time. Probably because I I feltso powerless growing up that I'm sointerested in how how power

00:30:38works. And Iwas so scared to advocate for myself andI was the least assertive person thatyou know until I met my wife and shetaught me how to be assertive and nowI'm like off to the races. So, that'sbeen helpful.>> Uh on that note, uhdo these tactics work on on kids andwives? Is this something that translates>> Yeah, absolutely not. I would notrecommend that. Especially if your wifeknows what you do for a living and hearsyou on the phone all the time and youtry to say, "What's the chance?" Andshe's like, "No chance." What's Don'tdon't pull that on me. I know whatyou're doing, right? And toddlers areterrorists, so I don't I haven't figuredthat one out. I I've resorted to bribesand maybe that is a little Machiavellianon the on the toddlers. You can be youcan be out of your mind working on that,but yeah, don't recommend it with yourspouse.>> I would pay a lot of money for a versionof you for toddlers. Oh my god. It'slikeI try to negotiate with my kid, I'm likeI'm like 3 minutes, he's like six. I'mlike4 minutes, no, six.He never budges. So, it's>> 5 minutes, he's like>> eight.Although sometimes he does that, too.>> I I would Do you Do you want a binky?And he goes, "Five binkies.">> [laughter]>> And you go, "Uh I don't know if we havefive." And he's all, "10 binkies.">> He's like, "Whatever you need, I'll getit if you go

00:31:53to sleep.">> Yeah. Yeah, please sleep.>> Yeah. Yeah, we need we need this fortoddlers. I would I would I wouldsubscribe.>> Miss Rachel's the closest thing we got.>> Yeah.Okay, so coming back to thiscompensation number. So, you touched onthis a bit and I think this is animportant part of your advice is whenthe number question comes up, who shouldspeak first? What should your approachbe if they ask you this question of howmuch do you want to make?>> Yeah, there's there's a decent amount ofnuance in this, too. So, one thing youshould realize is thatespecially earlier in your career,they're going to push on this harder.And that indicates that the personasking is really more looking for a acommoditized or a price sensitive hire,right? That can be okay. Right? There'snothing wrong with with sharing yournumber and getting a deal that thatmoves the needle early in your careerand even middle of your career. Thatchanges the higher up the ladder you go.And this is one of the reasons I want toshare this is that what got you herewon't get you there.Right? So, things start changing as youmature in your career. And so, whenyou're working with a top recruiter,they don't ask you about comp.They won't. The problem is toprecruiters only reach out to you whenyou're very well knownand they don't reach out to you veryoften.

00:33:08So, if you it's very difficult tooptimize for inbound attention thehigher up you go unless you become verypopular.Right? And then what happens is youshare less information because peoplecome to you in a different capacity.Right? So, nine times out of 10, arecruiter reaching out to you is goingto ask that number.Right?One time out of 10, they're going tojust focus on the value creation. Thoseare the ones you want to focus on thebest possible. But, it could beconfusing because so often you get adifferent side of the story, more of thecommodity type stuff. So,typically I'd recommend you answer,right? I don't talk about compensationuntil we're ready to make an offer. Itsounds like we're pretty far away there.I'd love the opportunity to learn moreabout the team, understand where thevalue comes inand proceed kind of down that path tomake sure we're a good fit. Is thatgoing to be a problem?And then typically they'll say, "Yeah,it is going to be a problem. I just needto know a number." Right? Now,I mean this is what it is veryuncomfortable to do this back and forthand to say no. Especially Americans havea hard time saying no. I have noticedthat other cultures can be more directand just say, "No, I'm not going to doit." Right? So, be it. Right? So,culturally there's a lot of differencesin how this conversation happens.And so, they say, "Look,

00:34:24we wewe need a number from you." You mightsay, "Look, I'm uncomfortable doing thatright now cuz I don't understand thescope of the role. Can you help meunderstand what you had in mind?Right? The reason I learned this isI used to be a marketing manager making$12 an hour in downtown San Franciscofor series A companies. Not knowing that$12 an hour wasn't a lot of money. Ijust didn't know any better. But then Ilooked at marketing managers and I sawthat they made 60 grand a year and I wassuddenly got offended at how littlemoney I was making.Right? Then I got promoted to directorin that period and was making $14 anhour. Good for me. Right? And then I sawthat marketing directors were making110,000 at the time. So when a recruitercalled me, I pulled that. I didn't wantto tell him I was making $14 an hour.They'd be like, who is this kid? He'snot very good. That's fake title.And instead I said, "What did you havein mind?" And they said, "Oh, we'relooking at 110 to 130." And I'd say,"Oh, I'm on the upper end of that now."And so I went from $14 an hour to$120,000 a year in a single month asingle jump.Just like that. That changed my life.One negotiation. It's one of the reasonsI'm so passionate about that. I hatedthe marketing work for what it's worth.But I thought like if I made a lot ofmoney, it would make that pain go awayof not liking my job. Turns out that wasa fool's errand, but that's a story foranother time.>> Do things in your experience

00:35:39ever fallapart when you try to do that? Becausethat is a scary thing to push back on.Just like, no, I'm not going to tell younumber and you're giving us advice onhow to say it in a nice way. And thenjust like, what did you have in mind?The fear is like, okay, they're going tohate me and they're going to be like,oh, this is not worth it. We're going tomove on. Has that ever happened? Whatare the odds that that might happen?>> A couple things about power. Right? So,if you have the ability to say no, youhave infinite power.Right?The nuance changes whenwhen you don't have a job and you needto pay your mortgage, you might answerthat differently because you want some.Right? Now, this isn't to shame somebodywho's feeling that way. Right? If you'reout of work for 6 weeks in SanFrancisco, you're homeless. Right?That's just the reality of thesituation. So if I got to say a numberto get a job,I I that's fine. Right? But understandthat once you're employed and somebody'sasking you and your needs are alreadygetting met, why do you need to getpushed around?Right? This is one reason that it'seasier to find a job when you have ajob. Now, I think this is a myth forwhat it's worth, but this is easierbecause naturally your needs are gettingmet financially to a degree.So, naturally you negotiate moreconfident.When you're out of work and you have theuncomfort of being out of work 6 months,12 months, 18 months,

00:36:54you have an identity tied to a chiefproduct officer role or VP of productlike that's your identity in ourcountry. We don't ask who you are andabout your kids. We say, "What do you dofor a living?"And when you are stripped of that title,it's uncomfortable. And we want thatpain to end.And so, we give in to these demandsbecause it's an authoritative figure andwe want that pain to go away.If we have the finances and the luxuryof being able to say no, we increase ourpower.If we have the ability to push back andpractice these difficult conversations,you will increase your power and you'llyou'll land at a higher rate because ofit. So, can it get frustrating?Absolutely. But if somebody disrespectsyou through that process, doesn't thatgive you an indication of who thecompany's working with?Right? Now again, I might accept thatbecause I need the money. I understand.Right? But it's very telling howsomebody's going to treat you dependingon very simple pushbacks. And onebehavioral psychology hack hereis we give someone a a positivereputation that they want to withholdwhether they deserve it or not.So,in this instance, you'd say therecruiter,"I want to thank you for being anadvocate for me and for respectingthat I won't share compensation figuresright now.I appreciate

00:38:10that."And then they are trapped. They have tosay, "No, I don't respect you. I have todo this."Or they have to say,"You're right. Like that makes sense.Let me move you forward or not. Right?Another option,you don't necessarily know if you're thebest solution for that fit or not.And so we're obviously very ingrainedwhen a recruiter reaches out to you andthey say, "Look, we're going to pay120 and you make 150." And you're like,"Oh, I'm not interested. That's not evenclose."I would recommend continuing thatprocess anyway to see as practice whatyou can negotiate. You can always say nolater. Right? Just because having thatpractice is going to make you hundredsof thousands if not millions more inyour career.Alternatively, if you feel bad about,"Oh, I wasted their time because I wastoo much for what they needed." Makerecommendations for them.So when the offer comes in and you saidit was a senior PM role and what yourealized is the JD and all of the workthat you did is actually a directorrole, but they're not going to pay for adirector role, right? How often doesthat happen?You get to say, "Look, you know, thisrole isn't in alignment with where we'reheaded, right? Would you like me to makean introduction to somebody that's abetter fit?"So you still get to help them. Youremove yourself.And then sometimes

00:39:25they say, "No,actually we do want the role to be moresenior. We're going to extend for you."Like my first VP role came out ofturning down a content manager positionfor 70,000. And 6 months later I landeda VP for a quarter million.Like that was my my first realm into VP.The initial offer was for contentmanager.So it came three, four levels up thefood chain. That was a long negotiation,but these things can happen if you don'tsay no too quickly.>> Along these lines, I want to touch on itfeels like maybe the coreuh approach you take, kind of the coreof your philosophy, which is to kind ofbreak out of this idea of some benchmarkfor a specific role and insteadmake it very clear to the company,"Here's the pain I will solve for youthat is really important to you andhere's why it's worth paying you thismuch more because it's such a bigproblem for you." Talk about just thatmindset.>> So, this really comes down to havingcuriosity and showing curiosity aboutthe actual problem. Because usually ifI'm speaking to a room of 400 people,right? Which I I'll occasionally do withsome communities. I'll ask them, "Who isactually doing the job that's on theirjob description?"Nobody will raise their hand. It's notlike you have your job description rightthere and that's what you do, right?

00:40:40There's always so much more that's notdocumented.Right? Now, when you're going into aposition you see a JD and like, "Yeah, Icould do all those things." But there'sso much more, right? This is anotherreason thatanchoring to a number too early istough. Because you anchor to, "Oh, thisis this is fair for a senior PM role."Right? This is fair. Then you go throughthe process of the interviewing,it's very clear that it's a directorrole. You're going to lead five people.They scoop another team under you. Oh,we're going to put a product-led growthmotion under you, too. There's an wholeengineering pod and there's this andthere's this. All of a sudden, that'scalled scope creep, right? So, theyscope creep the role. They talk abouthow they want a senior hire. They'reexcited about you. They get you excitedabout it. And then they then they giveyou the offer and it's actually 20%under the number that you originallyshared.And then you say, "Okay, well, thislooks like a director role. I want X."And they say, "But you said you onlywanted 140."Now they're using a number against youand it's very awkward to come back fromthat.And so, that's why we don't want toanchor too early. We want to understand.And so, this is one thing I wishespecially product engineers, designers,that side of the the the product stack,I would love for you to treat more ofthese like a sales conversation.Right? You are

00:41:55an enterprise solution, aconsulting solutionthat is several hundred thousand dollarsif not millions of dollars a year. Ifyou were to sell that product into anorganization, think enterprise B2B dealsand I know I'm getting a littlebuzzwordy here. Think take enterpriseB2B deal to Salesforce and you're goingto sell a million and a half dollarproduct. It would take you 18 months todevelop the relationships and close thatdeal.You have to developchampions in the organization. You haveto understand what value you can createfor each of those people so that theycan advocate for you.You don't come in and pitch them theprice right off the bat. You need tounderstand the value.So, through the process, it's adiscovery process.Why am I here?What gets you excited about me?Right? That's how we start aconversation. Too many interviews startwithyou know, tell me about yourself.Tell me about the stuff in the past. Ifyou're talking about your past, you'reon the back foot and you're losing thatconversation.You're the one revealing information.You're not getting anything.We instead want to have a conversationand say, "Look,some of the best interviews I've alwayshad felt a little bit more likeconsultations or brainstorming sessions.Are you open to having a chat like thattoday?"That's the first step.Typically, they say,

00:43:10"Yeah, that soundsway better than me trying to drill youwith questions." So, let me ask you,like, what are some of the things thatyou're excited about? I imagine, Lenny,you're excited to talk to me cuz I canhelp some of your audience negotiate.You've seen proof where dozens of yoursubscribers have made more money withthe article we wrote together. You'veeven seen that some of your guests,unknowingly,have been negotiated against with someof the work that I've done. Is thereanything that I missed? What's excitingto you? So, I want to clarify why I'm inthe room with you.Right? So, we do that as a PM. It soundslike Now, we move to labeling. It soundslikeyou have a challenge with this productline. It sounds like we need to move orship product faster. It sounds like AI'sbeen a problem and we need to shifttowardsnative AI.Is there anything that I missed?Right?Then they're revealing information. Youtake control of that conversation.And then we want to share, "What haveyou done about it?Like, how big of a problem is this inthe organization? This is basically aSWOT analysis.Like what are some of the things you'vedone well? What are some of the areasthat the team failed?What are some of the things we should bedoing that we're not?And what are some of the things weabsolutely shouldn't touch?So I want to add I want to ask all thesediscovery questions. They're like, "Ohlook, it's a

00:44:25it's a $10 million problemor we've we've gone through fivedifferent PMs in 6 months." And you'restarting to understand where the dirtylaundry in the company is.Then we get to sell the vacation.Right? Then we get to say, "Look,all right, so fast forward 6 months fromnow and we're working on this problemtogetherand we've solved the churn in theengineering departmentor in the design department or whatever.We've solved that and we've got twoproduct launches under our belt.When you head into that board meetingnext, how can we ensure that your headis held high?"So what I'm doing is I'm psychologicallywalking them to a position oflike a pain in the most position. I'veremoved the friction and the pain fromtheir shoulders and I forced them tovisualize a utopian situationand who is right next to them doingthat?I was.So when it comes to your competition,there is no competition. I'm the onlyperson who walked you into a vacationthat you want to be in looking forwardto your head held high in a boardmeeting that's usually stressful butinstead this time because you workedwith me, it's not stressful.Then all of a sudden when it comes tothe offer stage,there may be five other PMs but I canonly imagine working with Jacob. And sowhen I push back,

00:45:40the likelihood that Ibreak the rules is significantly higherthan if I hadn't done that.>> This is amazing. So trying to justsummarize what you're sharing here and Ithink it's important for people to alsoknow like you can do it in your ownwords. This is likely not somethingyou'll just be able to pop out and dolike this is something that takes timetodo well and it feels awkward probablyand that's why people work with you thatthey like probably role play in allthese things, but still like there'sthings people can pull out of this thatthey can do on their own.>> It could be tricky to understand whereyour value is, right? Cuz you're soclose to it. You just do this every day.And foryou know, product folks that only listento product folks andand are in the product ecosystem in yourbubble, Lenny,they're not seeing the impact onmarketing. They're not having thoseconversations necessarily. So it's soingrained in everything that you do thatyou could functionally be excellent, butin order to break these boundaries, youhave to be cross-functionallyunderstanding how it impacts others andthe motivations of others. That's whenthings really start to unlock. Andthat's where just understanding a littleperspective can be helpful in thatoutside influence there.>> I think this is important to justbriefly summarize your approach.So the idea here isfigure out in many ways what mattersmost to them,what problems

00:46:56do they have, what theysee in you just like understand thelandscape of where you could bring atons of value, help them see that likehere's the problem that I can help youwith, here's the problem that you havethat we need like here's the manyproblems that we can help you with. Andthen help them visualize you describe itas sell the vacation, help themvisualize, okay, now that this issolved, how is how how awesome wouldthat be?And part of there's like all thispsychological stuff you're throwing inthere just like how do you actually dothis?>> really make this concrete with a quickstory.>> do it.>> So,there's a very famous musicianwho was born the same year as me forthose super sleuths out therewho had a tour, a billion-dollar tour,and a documentary.And the director of said tour was a hotcommodity in Hollywood. Every agencywanted to sign this director. Thisdirector didn't want to just do moviedocumentaries, right? Wanted to startproducing actual movies. Like that's thedream, right?So, every agency wanted to sign this hotdirector who just did thisbillion-dollar deal withPeople already know who it is, right?And so, my client, the agent, asked me,like, we got to sign this. Like,

00:48:11itwould be stupid to go to any otheragency, right? We've done this, we'vedone that, we've represented JuliaRoberts and and Matt Damon and all thesethings. He's just naming name-dropping,right?Now, this is a actually a problembecause if we're leaning on logic andcredibility, we're losing. All right, weneed to sell the future and and own theemotion. And so,he she just asked me, how do we closethis deal?And to me, this was very simple. I said,if you already had the job, who wouldyou introduce him to?If you already had it, the deal'salready signed. So, put yourself in theposition that you're already doing thejob. That's why in interview process, ifyou treat it like you're consulting,you're doing a value exchange and you'reincreasing your value and you're askingthe right questions. If you feel likeyou're on the outside and you're havingto say, well, look, Lenny, I did thisand I did that. Did you see I have, youknow, 3 million words written? Like, whywouldn't you want to be the guest? Like,I don't care about what you've done, Icare about what you'll provide myaudience, right? So, in this deal, weget into the meeting, it's a big day,right? And I said,make the make the schedule theappointment already. Work with theassistant, schedule the appointment,right? With whoever it is it needs tobe. Needs to be a big-name person. So,we go into that interview andinevitably, the conversation goes, whyshould I sign your agency?

00:49:26And so, my client says, what are youdoing on Friday? I cleared a lunch withyourassistant.And he says, well, I guess I'm going tolunch. And she's like, great, I'll haveyou meet Steven.And he said, Steven who? And she said,Steven Spielberg.And then,some form after that, it was, where do Isign?Because the meeting was already set withSteven Spielberg. For somebody who wantsto get intofilm production, what better meeting tohave?Right? So, for the other agencies,they're like, "We're the greatest thing.Like, we've represented this directorthat did this media tour, and we didthat." They lost because we sold avacation and we made it a reality rightthen and there. And the value was clear.>> So, there's both this mindset shift of Iam I'm going to try to actually help youfigure out where I can be helpful andwhere the problems are, and then startactually thinking abouthow to fix this. And also, there's liketry to even do it. Sounds like you couldjust do it.>> can do it. So, one of the tricks of mybusiness islike I I can plant seeds with my clientsreally easily because I'm on the phonewith somebody and I'm understanding whothey need to connect with. And so,they might say, "Oh, I need, you know,I've been interested in getting to toGoogle or whatever." Let's say they'rein product. I say, "Oh,

00:50:41I I havesomebody in product at Google. Let memake a text for you real quick." AndI'll just do it while I'm on the phone.I'm just Just hold on a second. Hold on.And then what happens is they get thebeep.That's reciprocity. Like, I'm triggeringa reciprocity imbalance.And then I'm making another one forthem.So, I'll sometimes do two or threeintroductionsright then and there, and they see thevalue before I'm even off the phone.What I've also done is I've given threedifferent touch points where I can makesure that that person is followingthrough. I can get a 360° view of thatperson. I can ask one of those people toprompt them to close with me if I needto sell a deal.I'm getting a reciprocity imbalance. So,what I want to do is show that I havethe resources to support them, whetherthey sign a contract or not.And that's where we go. In In thisinstance, like if you want to role-playwith me for a second,something that would be really exciting.Like, Lenny, I want to understand what'sexciting to you.If today's podcast was the best podcast,the highest performing podcast that hadever happened, right? What would thatmean to you?And also, what did we do to make it sosuccessful? What are the comments thatpeople had to put down below? What arethe things they said to make you feellike my conversation with Jacob was thebest conversation I had all year? Whatwould that look

00:51:56like to you?>> Like I immediately love this question asayou know, like it sounds to people likethis is manipulative and like it couldcome across as that as an externalobserver, but to me I'm like this isexactly what I want to achieve and Ilove that you're thinking about thisthat I want you to be focused on thisand I would do a lot to help make thishappen. UhI guess to answer your question, I wouldjust love it to be uh very concretetactical advice that people can use tohelp negotiate their comp.And they spread this with all theirfriends that are like this is the bestthing you've ever heard around comp.>> And one of the things that we can do isthat we plant what you want someone tosay in that conversation as well. Sowhen I'm talking to these executives andI'm making the introductions, sometimesI'll ask or an introductions come to me,I'll be curious like when you go backand you share with a friend, what areyou going to say about me? Are you goingto say Jacob was really helpful? Or areyou going to say that Jacob was anRight? I'm curious. And sometimes I justmake a complete reframe so there's noother option.Right? Well, I'm obviously not going tosay you're an so I'm going tosay you're the great thing that I wantyou to say. I'm controlling thenarrative I want them to perpetuate. Soin this instance, and maybe some of yourreaders are going like this guy's atotal manipulative jerk, right? I willsay I hope that you use this for goodand not evil,

00:53:11but this is just the waypower works, right?I would hope that in the comment sectionyou say Lenny, this was such arefreshing and energeticpodcast. Like this is what we want moreof. This is exciting. We've done a lotof stuff in AI, this was very cool anddifferent, right? So I'm I'm suggestingif you felt that way, share somethinglike that below, right? Too many YouTubevideos are like oh like and subscribeand that's all they do, right? Whichdoes trigger action. It's a very simplething. But when it comes to navigatingyour net worth and negotiating forpower, these executives at the topcontrol what every other person issaying.Naturally, they know when somebody'stalking about them when they're not inthe room, and they've not only knowabout it, but they know what they saidabout them. Similar to when somebody'slike, "Oh, Lenny, we're going to doreference checks on you."What's the first thing you do? You callall those references and you say, "Whatare you going to say about me?"Right? Ideally, you can control that tosome capacity and improve the likelihoodof you moving forward. So, we already dothis.We just have to integrate it into someeveryday conversations and you couldbetter control outcomes.It's the same interview process. Whenyou go back to your committee,are you going to say,

00:54:27"Jacob solved XYZ and we're excited.Like, slam dunk. Let's move forward."And I like really quick, like, "Slamdunk."Right? Easy to remember.Or are you going to say there's a couplegaps here in some of the competitorsthat we have or some of the competitionseems more fulfilling.And I want to ask for that feedbackwhile I'm still on the call with you. Idon't want to wait for an email to say,"I'm sorry, you're not a fit." And thenyou ask for feedback and you don't getany. I have to do it while we're live inperson because you can't deny me in thatmoment without it being awkward.So, what are you going to say? Is this aslam dunk?What's one thing I should have askedthat I didn't? What are some areas thatthe other candidates excelled that youwish I showed more of?I want to understand where those gapsare so I have an opportunity to addressthem. And then,if I didn't make the mark, I'd say, "I'dlove to have a conversation with younext Thursday to talk through that inmore detail. Thank you for bringing thatto my attention."And you close the next conversation.You don't give up, necessarily.You know, that was another monologue,butthat was a that was a little bit insidethe mind of how I think about thesethings.>> No, this is so awesome. So, you know, ifyou think about a hiring manager havingsomeone like like, I don't knowI don't I don't Let's imagine I'minterviewing for a role. If I come tothem if and

00:55:42say, "Here's the problem.I'm going to solve churn for you. I'mgoing to fix your onboarding flow. I'mgoing to figure out how to level up yourdesign experience cuz I know that theseare big challenges for you right now."Like if I was the hiring manager, I'd belike, "Holy this is awesome. Thisis I just need someone to come in andsolve these problems for me. This is>> And you better deliver. Right? And youAnd that's the other thing. It'sIt sounds like if this guy can't deliver>> Mhm.>> it's not going to happen. If this galcan't deliver, that's frustrating.Right? I'm not suggestinggo so far outside of your comfort zonethat you feel like you can't do it.Right? Because that reputation willhaunt you. Right? You have to reallyunderstand. And I would also add thatI wouldn't be so sure that I'm going tofix the onboarding flow.I wouldn't be so sure that I'm not sosure that youknow that's the problem yet.The longer we can drag out the hiringprocess>> And this sounds like pulling teeth,especially when you're unemployed. Like,I just want the pain to be over. I'masking you to slow it down.The more you slow down the processthe more you fight back about themanufactured urgency of us needing toget into that role sooner, the moreinformation you're going to understandabout that company and how you couldreally help.Right? So, you could say, you know,Lenny, I hear that you want to fix the

00:56:57onboarding flow.I hear that. I hear this. But, it soundslike that product might be deprecatedanyway in this wave of AI. Is that apossibility?What I don't want to do is prioritizesomething that the team's going to cut.Right? That's going to hurt the P&L. Orwhatever.Now, I can only ask that question if Itruly ask the right questions tounderstand.Right? So, you may come in This is thesame concept as never be so sure of yourworth that you wouldn't accept more.You're so sure of the job descriptionthat they need these three things thatyou don't even try to ask the questionsto understand what the deeper problemis. And this going back also to whyfounders might be frustrated with mytalk track, I'm not asking for you totake your pie and give them a biggerslice. I'm asking for you to work withsomebody to expand the pie so everybodygets bigger slices. That's the that'sthe plan. And if you train yourcandidates and you're more revealing andif their performance is tied to it,naturally they need to ask morequestions to understand how to make ittrue.That's what we want. That's keepingcompanies up into the right.>> I like that you went there around don'tover promise because it's easy to saywe're going to solve all your pain foryou. I'm going to I'm going to be thebest in the world.>> promise. You under promise, overdeliver. Always. Under promise, overdeliver.

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00:59:02>> There's this balance of being confidentin your abilities to achieve somethingbig and solve problems, and then there'sthis other piece of just don't overpromise.Is there anything you help people do tohelp feel more confident about they willactually be a huge asset to this companyand they're worth all this extra money?How do you Is it like a pep talk? How doyou help people?>> Yeah,part of my hat I was hype man hat,right? You got to be a man to a degree,and I work with some of the mostprivileged and successful people in theworld. Right? It's not that hard to say,"Look at your life, and look at yourchoices. Most of the things you've donehave been good." Right? At leastfinancially. Right? We could debateabout the ethics of the companies theywork for and those things. Right? Now,most of the decisions that you've madein your career have made you a top tenthof a percentile of the earners on theplanet.Don't tell me you're not confident.If you can't hold that. Another thingthat I dois that I put it I I reframe everythingin a language they understand. So, ifI'm working with a sales leader,the job search process is an enterprisesales process. Like, if you understandenterprise sales, you understand how todo this. You just don't know how to doit for yourself. If you're in marketing,you should know about positioning andmarket research. That's the same thingas going into a job market andunderstanding what to do. You understand

01:00:17that an inbound lead is much easier toclose than an outbound lead. If you'rein product and you're orchestrating aPRD, right? It's the same thing. You'reunderstanding the users' demands. You'recreating for those demands. You're optlike you're developing the right flow.You're making the design as simple aspossible. You're eliminating friction.That's a term I use a lot, which I knowproduct leaders will use also. We wantto eliminate friction. Right? How doesthat look in your job search? Well, whatdoes the customer want? Who's yourbuyer? The buyer is the hiring manager.Maybe it's the chief product officer.Maybe it's the CEO. What do they careabout?When you're doing it for a company, youknow which customers to interview. Youknow how to do that. Well, you need tointerview lots of CEOs. You need tointerview lots of sales people who aretrying to solve this growth problem orlots of AI side. And again, it's notjust product. Right? So, you're nowinterviewing your customers. You'reunderstanding their needs. Now, you'redesigning solutions for their needs.Now, how do you make it as frictionlessas possible so it's a no-brainer andthey go through your user flow as easyas possible?So, for product folks, instead ofthinking, "Wow, this stuff sounds likeMachiavellian manipulation and it soundslike a power trip and it sounds likesomething I could never do because I'mnot Maybe I'm not as gregarious andmaybe I'm not

01:01:33a 6'3" tall white dude inCalifornia who's got that sales personaand he's got that extraversion. I'm notthat. Don't Don't be me.Don't be Jacob Light. Be you, yourauthentic you,and apply it to what you already know.You know how to do this in product.Design it for your career.And you remember the early days ofwriting PRDs and how rough it was?Remember how rough it was to go back tothe engineering team and just little bylittle get product sprints out where theproduct is just moving a little bit at atime. Remember how hard that was? Theearly days of managing your career likethis will feel like that, too.But you also know that if you're 10years in your career, this stuff becomessecond nature.Right? So, I want to reframe to theexperiences that you already know andthat will develop confidence.>> I like this framing you're referencinghere for product people of this idealike you're basically trying to positionyourself the way you'd position aproduct kind of the value prop of thebasically as a product team, you'retrying to sell people on here's why thisproduct is worth paying money for. Andin this and you do that by understandingyou do your research, you understandtheir pain points, you understand how toposition it so that you make it clearthis will solve your pain point.Essentially, that's what you'redescribing from when you're

01:02:48interviewingis think about it that same way.>> The part I don't want to gloss over ismaking it frictionless.Right? So,interviewing is a skill on both sides.Most people don't know how to interviewvery well. It's tell me about yourself.Like, tell me about this product youbuilt. Tell me about that, how thatlooked. You don't get anywhere talkingabout the past.Like you you might build credibility andand all that great.You don't start solving problems in thatprocess. So, they're like, "Okay, well,I saw that." Now, you're going to go onto the next person. They're going to dothe same crap.Right? Same thing, same thing, samething. So, you repeat your story adnauseam and you never learn anything andyou never grow.So, how do we make this frictionless?Well, I want to make it cognitivelyeasier for you to have a conversationwith me by leading.That's why I had that framework I wastalking about earlier. Like, why am Ihere?What are the problems you have? Isuspect it's this. What have you doneabout it? What would it look like if wesolved it? Now, I'm taking so much ofthe pressure off of you. I'm controllingthe narrative and I'm collecting moreinformation while revealing none aboutmy comp expectations. And what I'mfocused on is creating as much value aspossible.Now, there are situations wherecompanies don't have the budget, right?Like, this isn't a miracle drug kind ofthing. But I'm making it frictionlessto at least get to the part where theywant you.

01:04:03That's the first step. Theyhave to want you for you to have anyleverage.Right? Then even in the interviewprocesses, I might say, "Hey Lenny, youknow, I suspect the next person I talkto from your ecosystem is MarcAndreessen. Right? Can you give me someadvice on how I should work with Marc?I want you to coach me on how to dealwith Marc."That's going to make it morefrictionless, right? Now, I also want toput you in a position to be a coachbecause coaches want their players tosucceed.So, if I'm having you coach me,psychologically, you're going to go talkto Marc and you're going to say, "HeyMarc, you're going to have to talk toJacob for all these reasons, right?"Then when I talk to Marc,I get to say, "You know, Lenny sharedthat I should talk about X Y Z thing.Are those Is that really what you careabout?"I'm making it frictionless across theprocess and I'm closing the next part ofthe conversation regardless of whetheryou wanted me to introduce me to thoseother people or not.So, you might say, let's say you'reinterviewing for product role,I suspect you want me to talk to thehead of engineering.I suspect you want me to talk to Clay,the VP of marketing. And I suspect youwant me to talk to Catherine, the VP ofsales. Right?What would you like me to say them?What's the message you want me to share?And they may not have had them in theinterview process in the cycle,

01:05:18but I'mputting them in the cycle.Like I'm making it easier for you toknow who to introduce me to next. Andthen I'll even go as far as saying, "I'mnot available again until Thursday.What's the chance that time works?"So, I'm building scarcity about my time.I can meet with this VP then, but I'mmaking myself stickier in theorganization. I'm getting more knowledgeabout what people need.Right? So, this is similar to selling anenterprise deal. You're buildingchampionsin the organization that love you, andthey're all coaching you on how to coachyou like to work with each other.So, you're getting the inside scoop onhow to navigate that. That's how youbecome hyper valuable. You need tocreate that leverage if you want to takethat standard 20% we talked about andmake it 40 or more.That's why it starts much sooner.Because if you're not doing that, if youcome to me and you're like, "Jacob, Ihave an offer." I can get you maybe 40.Right? If you come to me sooner, I mighthave elevated that initial offer 40without you knowing it, and then wemoved it even further.Right? So, it's a big process that weneed to be mindful of.>> So, it seems like a big part of yourprocess and advice is to flip it flipthe interview as much as you can toextract information so that you canbuild a case of how you will solve theirpain.Say you're

01:06:34like an IC product managerinterviewing at Meta.What are the odds you can kind of flipthese conversations or take a big chunkof that talkfrom them asking you, you know, theirstandard questions to you asking themwhat problem what are the biggestproblems, what would be awesome if Icame in, like all that stuff you sharedabout to extract to build this caselater?>> One of the things I found frustratingabout IC roles is they're not oftenrewarded as well as leadership roles,which is frustrating becausethere are a lot of very talented ICs.Now, I have seen specifically with Meta,I actually interviewed for a Meta ICmanager role like an i9, it was like 1.2million a year. They were specificallyhiring former CEOs and I found that tobe interesting. They hired 150 growthPMs at this i9 level and they wererewarding them very well.I don't think it changes.I think that whether you're a leader ofpeople or you're a leader of process,you're still a leader. And the reason Ipropose taking ownership of theconversation isn't to besteamrolling or talking over people oror completely, like I'm not saying dothis devoid of context. You don't justblow out and like talk over somebody andramble, right? Which I'm one to talk,apparently. But uhyou go into this conversation and youeven flow with them.Right? But you The reason I want

01:07:49you totake ownership is cuz I can't controlwho you're going to get on the otherside of the line.I can't control the mood they're in. Ican't control their motivations. I can'tSo, as a coach, I can't control how theyshow up,but you can control how you show up.And we can work to navigate and then youstart to get someI guess uh nuanced skills where you readbody language and you feel comfortablesaying, "You know, Lenny, I saw thatthat maybe wasn't the right thing tosay. Can you tell me more about that?"Then you start getting confidence and Isay assertiveness, not aggressiveness.There's a difference.And so, that comes across as confidence.And so, I don't think there's adifference between being an IC and beinga leader in terms of how you approachthis. But I have noticed a difference inthe pay and that can be frustrating. So,that means that if I were working withmore IC folks, I would ask questionslike"It sounds like, you know, independentcontributor roles are very valuable atMeta. Can you share a little bit abouthow they're valued compared to leaderson the team?"I might ask a question like that.Because again, they can't say we valueyou less.I've given them a reputation where theyhave to say we value you.Thenyou get your

01:09:04offer, you check levels oryou check some of these benchmarksbecause we all do, right? We look, wewant to know, right? Maybe we call up acouple friends that are similar level.Then you can use objective criteriaagainst them. You're like, you know, youmentioned that you valued ICs as much asleaders.Right? And I just got curious, so I dida little digging and it it looks likethis this is like about 30% under what aleader would make. Is that Is thatnormal?Right? I appreciate you being anadvocate for me and I'm pushing back.Can you help me understand if we canlift this to bemore equitable?Right? I'm using information I gatheredfor them and I'm not just beating themup with it. I'm just saying like yousaidwe treat this fairly. Prove it.Or prove to me that you lied.>> And this And this works is what you'resaying cuz that like if I was the hiringmanager, I'd be like, "No, I'm sorry,that's just not how it is.">> I mean, in in many cases it can be,right? ButI'm trying to I'm trying to open up anemotional conversation more so thanlogic and credibility cuz you lose. Youwill always lose the logical andcredible argument against a company.There's information asymmetry here. Metanegotiates thousands of times a day. Younegotiate four or five times in yourcareer. That's it. Right? Thousands oftimes a day. Recruiters, thousands oftimes a day. You are at such adisadvantage. This should

01:10:19also give youconfidence to negotiate in the firstplace. You are at such a disadvantage.Right? I just wrote an article onuh the game of Werewolfas an exampleabout how important information is. So,the game of Werewolf is pretty simple.Say there's 12 people sitting in a room.Two, three of them are werewolves,right? They draw a card at random. Threepeople, two people, whatever. They gettheir card and they know they'rewerewolves.There's a day and night scene and thewerewolves get to reveal themselves toeach other. So, they say, "Oh, you're awerewolf?" Yeah, okay. We're werewolves.Right? Then they go round by round andthey politic to vote somebody off of thetable.Right?Only two two three people understand,right? When the werewolves reach paritywith the villagers, the werewolves win.Right?In even alike a six to one or a five to onesituation, werewolves win 60 70% of thetime.It shows the power of information. Theyunderstand everyone else is clueless.They know who's dangerous, they knowwho's not. And that's just a that's aoutnumbered situation. Now, thesecompanies have significant leverage overyou.They know what people make, they knowwhat others make, they know what they'llaccept, they know their budgets, theyknow how to change their budgets.And what I find interesting, especiallywith executives, they push

01:11:34back on thisprocess. And I'm not going to lie, it'sa much easier for executives to do thisthan it is for middle managers or lower.So, if you are hiring manager Lenny andyou put your director head on, like it'seasy to deny somebody like that becauseit's a little bit easier to find anotherproduct manager. A little bit, right? Ifwe do our job to differentiate, thenwe're doing better there.But,executives that are afraid to push back,like your job is to make these rules.You know who to influence to changethem.You understand how the P&L works. That'swhat you do for a living. And you'retelling me there's no flexibility?You built it. Humans built this.This is not concrete authority.This can be influenced.Why not try?>> Let's try to summarize maybe the topfivetactical tips that you've shared. Ifwe're just to kind of go through inbullet points, just things people shouldkeep in mind when they're trying tonegotiate. Like one that comes to mindis don't speak don't show the numberfirst. Try to get them to share numberfirst. Is that is that right?>> Yeah, you also have to know how torespond if they share the number first.I'd rather no numbers be discussed ifyou're open tojust waiting it out and saying, "So."Important pieces So, the first one isyou never be so

01:12:49sure of your worth thatyou wouldn't accept more. That's I thinkChris Voss quotes that quite frequent.Uh the other one is never split thedifference and I have a I have a goodstory about that. So, just becausesomebody says, you know,you started 100, they you say 200, theycome in at 150,that's lazy, right?One one brief example of this, I had auh chief revenue officerandthey were paid $350,000 base salary,350,000bonus. So, 700,000 cash potential eachyear.Uh so, that's called on-target earnings.They'll make 700. When we negotiatedtheir severance,we said we wanted 6 months on-targetearnings. It was all agreed, right? Thepaperwork comes back and it says 6months base salary,not on-target earnings.So,that means6 months of base salary is like 187.5,right? So, they cut his severance inhalf by doing that. Now, his responsewas I'll just tell the CEO, like let'sup that 90 and it'll be down 90. He wasgoing to split the difference like 260or something whatever the math out to.And I said instead, simply ask,was that a mistake?Right? You know, we had discussedon-target earnings, that wasintentional, was that a mistake?

01:14:05Hesaid, "Oh, yeah, must have been. Let mejust tell the attorneys to fix it. Feelfree to redline it."So, he almost lost 90 grand justsplitting the difference if not more,right?And then turns out 12 months later hegot fired and then he was able to recoup$350,000 over 6 months. So, littlethings like trying to split thedifferenceuh too early can be painful. So, thatwastwo points, I think. I know you know,this is parts I'm bad at. Trying to geta list of five.>> is great.>> Patience is more important. Like thingsneed to slow down. Haste equals risk.Theslower you go, the more opportunity youhave to collect information so that youcan build a compelling case, right?That's important. UhI am a a big believer in Aristotle andhis principles of rhetoric and ethos,pathos, logos. And so I've mentioned alittle bit of this in their more commontone of uh logic, credibility, andemotion.Uh timing is another one that we don'toften talk about. Kairos is important.But too many executives lean oncredibility and logic because we'retrying to do that. We don't showemotion. We don't show the authenticside of ourselves in corporate. I thinkoften times cuz we're working soullessjobs that we don't believe in and we'rejust trying to make do and survive forour families. I think there's a greater

01:15:20need there.The emotional side is where a lot ofdeals get unfair.So if we understand how to tap intothat,I want to say Chris Voss I keepmentioning Chris Voss, but he I think hecalls like tactical empathy, right?Which does That sounds moreMachiavellian than anything I've eversaid, right? But understanding thosemotivations and understanding how toplay on that can be important.Right? So when we talk aboutgiving people a positive reputation,we're playing into some emotions here.So if I'm a female negotiating withanother female, I might say, "You know,I appreciate that you've always been anadvocate for women and you support oneanother. Like that's something I respectabout you."Right? And then their comp comes inlower than a man's comp,you can call them out on that and say,"If you were in my shoes, what would youdo?"That's one of my favorite lines. If youwere in my shoes, like go backwards 5years in your career, that's where I'mat right now. If you were in my shoes,what would you ask for?I love that when negotiations stallalso, right? Like you know what'spossible here. You know what levers wehave. It sounds like we're capped outhere.If you were in my shoes, what else wouldyou explore?And you start to go that route as well.Um the other piece is this is acollaboration, not a confrontation.

01:16:35So if I could give visual advice, oftentimes This is Oh wait, it's also couldbe difficult in a Zoom. Like you and Iare kind of face-to-face.Like we have this problem between us,right? That's an adversarial position. Iwant you to physically pretend thatyou're in the same roomand I walk to to your office and I putmy arm around you, if you're comfortablewith it, and I'm instead of us arguingover something, we're whiteboarding asolution together.I want collaboration andthat's how we break down walls andbarriers because you're sharinginformation, I'm sharing information,those types of things.TheI think that was four, maybe it wasfive.Another one ismake it about we, not about me.Right? So, another severanceconversationuh with a chief marketing officer. Thisis a hundred and two hundredmillion-dollar private company coupleyears ago.So, she comes in,she gets offered $340,000 base salary,30% bonus, equity, right? We tried topush on all that and the CEO said,"Look, one of the things I pride myselfinis that everyone here has $340,000 base,30%, and the same equity package.Everyone on the executive leadership.

01:17:50Right? Now, she was getting pulled froma hot company,which is risky cuz she was safe there.She actually was getting a raise comingto this company. So, we didn't need topush on more money. What we went for wasseverance protections.Right? And so, we asked, like,standard is about six months, maybe plusuh another month for every year served.And the CEO is like, "Oh, we've neverdone that before."And so, instead of it being like you'renegotiating the terms of your divorcebefore you get married, that's what'sawkward here. We said, "Well, given thatwe've had a problem with talent beingpoached, you going elsewhere, and wejust did a big riff,wouldn't it make us look good toproactively give everyone on theexecutive leadership team six months toshow that they're safe and committed tothe company?"And then we fed that idea to the CEO sothe CEO could look like the hero.More importantly, when my client cameinto that company, she looked like aherobecause everyone's like, "That's thewoman that negotiated us all severanceprotections."Right?So we made the company we used thecompany's equitable policies to do that.Now I will say that's not common.Right? So the folk folks are like, "Ben,that's fantastical." That may nothappen. Like especially with privateequity, it usually doesn't. Right? Thereare There are ways that

01:19:06we want toappeal to a humanity more so if we can.UmBonus point. I know I'm monologuing alot.Don't be afraid to get creative. Likecreativity is interesting and one timewe got someone a G Wagon andafter being like maxed out on comp Ilike this story cuz it's so out of thisworld. Not you're not going to get a GWagon. I promise you it is likely notgoing to happen. But we had the CEO whohad two offers that were both 2.4million and they were stalled. I know,first world problem, right? Like tinyviolin. 2.4 million a year this CEOdeal. And she told me and this wasjust a joke. Like it this wasn't someMachiavellian plan. She was like, "Look,I don't know which to choose. They'reboth maxed out." And I was trying to saywhich one would you like more. Shewasn't giving me anything. Right?They're both fine, whatever. LikeAnd I said, "Well, I don't know. Whatkind of car do you like?"Right?And uhshe She's like, "Oh, I love Mercedes."Right? And I was like, "Tell them that."But jokingly cuz they they inevitablycame to look, "What's it going to taketo hire you?" And she's like, "I don'tknow. Likeoh, maybe a company car." And they said,"Well, what kind do you like?" And thenshe said, "Mercedes." And they're like,"Done. What model?"And then she's

01:20:21like, "Oh, G Wagon." Andwhat happened was all the budgets werecapped.But it was a company write-offto have a 6,000 lb vehicle. So it there$350,000 car added to her contractthat was a company write-off thatreduced the tax expense.So, like that's not going to happen. Idon't suggest people go ask for GWagons, but the fact iswe came to a stall point and we found asolution for that.>> I love these stories.Uh another tip to share just that I wantto double down on is don't is don'tnegotiate over an email.Make it in person as if possible orvideo call, right?>> Yeah, absolutely. Just you have to bemore comfortable understanding the bodylanguage and the tone. You're picking upthese things that you can't control whensomebody opens their phone.Like the worst thing is they're on theirway to pick up their kids at school andthey open your email and it just doesn'tsit right with them and they're intraffic. Like you can't control whethersomeone's going to do that. Or like Isaid earlier, being busy at the airport,rushed through security. Or they justgot off a call with somebody that'sfrustrated. But if I hop into a videocall and I can see that you're visiblyfrustrated, like if for whatever reasonyou look like your toddler kept you upall night, I'd say, "Hey Lenny, wouldyou like to reschedule

01:21:36to a time thatfeels more comfortable for you?"Right? So, that we can get the most outof our time together. Like that is ablessing, right? You couldn't do thatover email.>> Say things actually do fall apart. Saythey just pushed you hard and they'rejust like"Mm, okay. We're going to move on withanother candidate." Or they make you anoffer and they just they rescinded orthey promise something and they don'tdeliver. How do you approach when thingsgo sideways?>> Couple Couple elements to that story.One, the the not delivering piece isthat's more common. Rescinded offers, Ihave never had a client with a rescindedoffer.The What I will get is a no. This is thetop, take it or leave it. Right? Fine.They go they get a ultimatum. Fine. Ihave, however, helped somebody. Theyweren't a client. See also a CMO.And sheshe was offered an $800,000 contracttotal cash-wise andit was rescinded. And so I I took thiscase on pro bono. I got a phone call. Iwas like, I I just want to see how thisplays out, right? And she was in tears.She lost this deal. She Turns out shehad a career coach who said, "You needto negotiate like a white man."Like that was her advice. Like you needto be aggressive, you need to do this,

01:22:51you need to do that. Like you need tonegotiate for your worth, which youknow, I understand the appeal of that aslike if I would understand like a womanthat wants to negotiate like a man andget hers, I respect that, right? In thissituation, the context that was missingis that she was negotiating with otherwomen.So she was negotiating with this femaleCEO and the three other females on theexecutive leadership team and theyrescinded the offer because it soundedlike she was a bad cultural fit.Because she was acting like a man. Likeshe wasn't being her authentic self. Shewas acting in this persona that shewasn't comfortable with. And to behonest, she said to me, "I wasn'tcomfortable with that advice, but I didit anyway becausewomen should stand up for each other. Weshould push, right?" And I commended herfor that. And so what we did was I said,"Look,call the CEO, explain what happened.Share that, you know,obviouslyit's important that women take care ofeach other, right? And it's clear to methat you have. There's that positivereputation, right? I got to be honestwith you. I hired a coachto try to understand what to do becausein the past I failed. In the past Ihaven't been my best advocate. In thepast I've done less.I suspect you know what that's

01:24:06like.Boom, shared identity, right? They allknow All women know this togethercollectively. This is a shared identitytribe thing, right?I made a mistakeand I I I disagreed with the advice, butI did it anyway cuz I had to toAnd they brought the offer back on thetable for her authenticity andtransparency.So, like that was the path that weit was two phone calls to come up withthat idea.She got that deal back on the table, isnow happily making 800,000 a year.Right? So, when things go south,approach it with honesty, integrity. Saylike, I made a mistake. Take ownership.Extreme ownership really helps here.That could probably be one of thosethose points. When you fail to live todeliver, take ownership of that. Takethat note. It may mean you're gettinglevel set a little bit in your career.That's okay. You're still growing.>> That is so I I love that approach ofjust like, okay, I hired this coach,they gave me bad advice. It was itactually>> feel good, too. I was like, shoot, Ihired me.>> [laughter]>> It's interesting how negotiation isdifferent if you're a man versus awoman. Do you take a different approachif it's a female client versus a maleand it's just like, here's you shouldapproach it this way or or depends onthe>> I take a different approach on everyperson.>> Yeah.>> So, whether you're a product

01:25:21leader or amarketing leader or a sales leader oryou're from San Francisco or you're fromDubai or you're from New York or you'refrom LA, likeor you're German or you're Everybody isdifferent culturally. So, male, female,like every little nuance is isimportant. If you're, you know, you'regay or you're black or you're There aredifferent challenges that everybody hasto overcome.Right? And I rememberthis was a powerful one. I was speakingto Chief. There was about 400 women inChief and I'm the I'm the white dudemansplaining to all these women aboutnegotiations. Like the scariest positionfor me to be in.And I remember there was thisAfrican-American galand she said, "Jacob, should we justnegotiate for 84% because that's whatwe're going to get anyway?"Right? Like that's defeatist. Like thatsucks to have that feeling. Right? Now,I don't know what that feels like. LikeI have I havedone fairly well for myself and I thereare some advantages that I had. But Isaid, "Look, like how many of you inhere are mothers?" Many of these womenraised their hands, right? "How many ofyou are mothers to daughters?"Right? Many of them raised their hands.I said, "Could you look your little girlin the eyes and say, 'Sweetheart, justget 80% out there'?"Just go after that and do that.

01:26:37Right?And it kind of like shocked the room alittle bit because I I can't compete onthat level, right? I don't know whatthat feels like. I can't do that. But Isaid, "Look, if we don't learn to growtogether,we're never going to solve thisproblem."So, what we're trying to do here, andthis is what I encourage all listenersto do,fight back. There's a big powerimbalance, right? They Here Here's thefounders coming again and again. Like,"Jacob, don't tell them to do that. Idon't want to revolt, right? Take careof them, right?"Push back because a rising tide raisesall ships.Right? If companies want to rely onprecedent,have the audacity to raise the precedentbecause the next people in line willwill do that.To the point about collaboration, thiswas actually with a one of your readersthat read the that first article we did.Um we made a lot of money on this deal.>> And they came to you to work with you?Oh, I love this.>> Yeah, so the this is fun.>> Mhm.>> But so, this is kind of like a privateequity hostile takeover situation. Andthis reader of yours was getting pushedout of the company.And if you try to go head-to-head withthe PE, you're going to lose, right?He had a great relationship with theCEO, 10-year relationship.And but the CEO wouldn't take any actionto support him,right? Until we made it about

01:27:53we. TheCEO had made comments that I'm probablygoing to get fired, too, right? So, whatwe did was we talked to the CEO and wesaid,"Whatever precedent you help me deliver,you're going to get two to three timesthat. So, we need to set this up."Right? So, then they were full on. Youhad the CEO and the CPOputting together a game plan to advocateagainst the private equity,right? To support that transition plan,we got a retention bonus and a severancebonus on the table because of that.Right? Cuz now the CEO is protected aswell, can point back to some precedent.Right? So, not everybody does it out ofthe goodness of their heart, not in acapitalist society, right? You have toshow themyour motivations here are important.Right? So, women negotiating, if youwant women after youto have an opportunity have theopportunities and better opportunitiesthan you have, you have to have the youhave to have the guts to do that. Andthat's very easy for me to say, I'm notin your shoes, but naturally we have tobe a rising tide. And there are folksthat aren't going to take thatchallenge, and that's okay, right? Let'sall push for those to help it make iteasier for everyone.>> I love this point you made about howthere's no one way to approach this. Theway I was originally thinking we do thischat is like a step-by-step guide tonegotiating. Here's what you do, 1 2 34,

01:29:08and this is how your comp goes wayup. And what you told me is that thatjust doesn't exist. There's so manyvariables, there's so many types ofcompanies, roles, seniority, people'sbackgrounds. Maybe speak to just like ifyou ever see someone telling you here'syour steps to negotiate comp, it's justit's probably not real.>> That was one of the things that was hardabout the article we wrote togetherwas that I have gains, right? It's ait's a process that I follow. It's not aconcrete step-by-step process, but oneof the reasons I'm so hesitant to gothis route is becausenegotiation comes off so complicated.It's so complicated and so academic.When you look at the books that werewritten, you have Well, Chris Voss haskind of popularized it lately, but it'slike imagine there's a gun to your headin an FBI situation, you're likeI don't have a gun to my head, I justhave dealing with my boss, and I want tounderstand how to do this. Or you readGetting to Yes, and it's like what whatyou need is a strong BATNA and a goodZOPA, and it's like very academic, andyou're in the moment trying to have aconversation and have empathy andlisten.But then you're like, what's my zone ofpossible agreement? What's my bestalternative to likethose things are all very true, but itcomes off intimidating.Right? Andwhen we

01:30:23when we try to focus so much onframeworks and and academic, we stoplistening.And that's one of the most importantparts is curiosity and empathy are thetwo things you need to have the most.Right? If you're reaching a block,why does that block exist?If you don't know the answer, youhaven't asked the right questions.Right? You don't necessarily know. It'san information imbalance that you have.And really what negotiation comes downto information and timing. That's whatcreates power.Right? Those are the three things.That's all you need to know. You have tohave the information.When we were talking about that game ofWerewolf,even when you're outnumbered five toone, if you have more information, theodds are you'll win.Right? So,I don't want it to be overlycomplicated. One of theI I guess I have to say it. So, I'mtrying to write a book this year. I'mgoing to write it, right? I'm going towrite it.>> It now must happen.>> Now it must happen. I know like I justkind of clenched up a little bit cuzlike I got I got to do it.>> It's still early in the year. You got somuch time.>> Oh, yeah, thanks. All right. I I'm aprolific writer. I'll get after that.But the book title is calledPredetermined.And I wanted it to be Predetermined likewith a question mark.Right? Because none of these outcomesare predetermined.No matter what

01:31:38situation you are in yourlife, how you were raised, it will itcould be more difficult for you, butit's not predetermined.And it'sit's one of the reasons I love this workis that I don't know what the outcomecan be.We don't know. You should never be sosure because then you start putting aceiling on your life.And one of one of my favorite things toask somebody,and they're like, "Oh, Jacob, I want todo this in 5 years."I say, "What would that look like if itwas done in one?What must be true?"I'm like, truncating that experiencejust to think through it. Notnecessarily that I'm asking them to rushthrough it or whatever.But I have clients that they'll have 10or 15 million dollars in the bank andthey'll be in their late 50s.And they're like, "Oh, I need 10 or 15more to retire."What?What do you mean you need 10 to 15?Like, if I had a million dollars, Iwould retire. Like, give me a break.Like, that seems like so much money tome. Why is that the case?Right?Umso, I like to challenge those thosenotions there, right?UmIt's an important thing to think about.Like, it's not as step-by-step as itneeds to be. Cuz sometimesanother one of my favorite questions,what would your life look like withless?Maybe a minimalist or stoic typephilosophy.One of these Hollywood deals we did,uh we had a director

01:32:53and a Marvelsuperhero that got in a spat on a bigfranchise. This is aestimated 500 million to billion-dollarfranchise opportunity.This A-list celebrityuh and their writeruhon this third installment of a moviedidn't like it.So, think celebrity kind of being aprima donna. I hate it. I don't like thedirection it's going. They're notwriting me right. Fire him.Right? Offended the original directorcuz they wrote the first twomovies and they were very successful,right? To build this franchise. So,pissed off, right?Next writer comes in. This is worse thanthe one before. Can we just hire backthe first one and get work through it,right? So, 6 months later, money,production delays, all that. Go back tothat original writer.And the agency's like,"We got to throw money at this guy."Like, to get him to say yes. Like,here's a million more dollars, right?Didn't do it. Like, a million dollarswasn't enough to mend this relationship.The important lesson here is it's notalways about money.That individual was making $10 million ayear. A 10% increase to have to go backto somebody they didn't like, notpowerful.Right? My suggestion was, can you askthe

01:34:09actor, this A-list celebrity,to humble themselves and apologize?And that is what moved the deal acrossthe line. Actually came in andapologized for the behavior, it's notgoing to be like that. That's what gotthe deal back together, and the milliondollars was saved.So, it's not always about money. I use alot of money in the stories because it'skind of shock and awe. It's like, wow,like that's going to have big impact.Like, at the end of the day, if you'remaking $18 an hour and you negotiate to24, like such a material difference inyour life.That is so magical to maybe be able toafford gas for the first time. Right?And then I'm telling stories wherepeople haven't thought abouthow much gas costs ever, right? So, likethere are situations I remember that. Ijust 10 years ago, well, 12 years ago, Iwas homeless, like fighting through allthis stuff, and didn't know if I couldpay for gas. So, it's one of the reasonsI'm inspired to do that. Is that you canmake a material difference and itcompounds throughout your life, but it'snot always about money.>> I want to follow this Hollywood threadbefore we wrap up.Uh I love that you work with Hollywoodfolks, uhcelebrities, and also deck people, whichis most of the audience here.Is there another uh wild story from yourHollywood life uh that might be fun

01:35:24toshare?>> I think what's interesting aboutHollywood is thatit's so far-fetched.And you were talking about what happenswhen offers get rescinded, right? And Ibefore I was working in Hollywood, IwouldI would have tried to talk people intoasking for $20,000 more, right? Whichafter taxes is like eight, right? Andthen when you look at it, it's like $400a month or whatever that you're you'restruggling to maybe ask for 10,000grand, right? In Hollywood, like we didthis deal with I can't share who. A-listcelebrity.And the company saidwe want to pay her $5 million for thismovie. And the attorney came back, wewant $22 million. LikeLike talk about being aggressive.Right?And the production company is like, allright, how about 13?And this was in like a 2-day span. Sothey went from $5 million to $13 millionin 2 days.And the other they're like, well,instead of 22, how about 18, right? Likethey're moving $4 million chunks at atime. And we're over here on tech goinglike, oh, I wonder if I can get 10,000.Right? So like that's something that Ijust find absolutely

01:36:39wild. The biggerthe Like this is just like you want tomake money solve rich people problems,right? That's what happens, right? It'sit's just escalated. I can only imaginewhat a negotiation with like Elon Muskwould be like. They'll throw 100 millionat it. And you're like, oh my gosh. LikeI also found out thata million seconds is like 11 days.Have you ever heard this? A millionseconds is 11 days. Do you know how Doyou know how long a billion seconds is?>> Like probably hundreds of years.>> It's like 30. 30 years.>> 31 years. So between 11 days That's thediscrepancy between a million and abillion, right? And so these are justlike these things scale soexponentially.It's just that what you say and how younegotiate just kind of changes. So ifyou want to really increase your comp,you do have to move rooms.Right? You have to start networking andmaking connections with folks that cando that with you.>> Maybe as a last question just to getvery tactical. Somebody that maybe isabout to get an offer, got an offer,will get an offer in the near future.What's like what's the first thing theyshould do to help them increase theircomp? Is it just reply with is thereroom for more? What's like what shouldthey do when they get that email?>> Okay.You always give me these nuanced

01:37:55ones,huh? So, it'sThey get it from the recruiter or theyget>> Yeah, let's say the recruiter's it'sprobably where Yeah.>> Recruiter's going to again, they'reprobably going to have that 20% with aroom there.If you're okay with that, I might again,just say what's the chance we can we canbump like this is what I was lookingfor.Right? I would probably knowing that therecruiter is going to split thedifference, I would probably anchorhigher versus lower. There have beensome studies and I was reading some I'veread a lot of negotiation books. There'slike one from the 70s on thesenegotiation games and those whothose who anchored egregiously high won75% more than those who just try to bereasonable. Right? So, it's like look, Iwas hoping for 150,000 more. Sometimesyou get 70. Right? Sometimes you get 50.But if you ask for 50 more, you wouldhave got 15. Right? So,if you are going to re-anchor, just sayhey, I was kind of in the ballpark atthis.Again, with the nuance, you may havealready committed to a range before andit can be difficult to have thatconversation. Right? So, I might sayhey, after we've had the conversationswith hiring manager and and yada yada,it sounds like the scope of the role hasincreased. Are you open to revisitingthe comp structure on this? That'slikely how I would respond.

01:39:11If therecruiter says this is all we can do,and you have the audacity to do this, Imay send a text message or an email tothe hiring manager and say hey, we'realmost across the line. It sounds likewe had a sticking point.Are you open to have a conversation?That's who I want to close with. And Idon't want to put the recruiter down.You say it just sounds like we're at asticking point here and I'm reallylooking forward to working with you. Areyou open to chat real quick? I don'tneed to have a big laundry list of I'mgoing to do do for you and I'm going todo that. Like that will not work. AndI've noticed this in our back and forthin your emails. Like, you'll respondwith two words.That's all you need.Right? You don't often need more. So,like, the more confident you get, theshorter your communication gets.And sometimes it can be as simple astexting the hiring manager saying, "Opento chat."You don't give them any reason. It'sjust open to chat. And then you controlthe conversation from there.Hopefully that was tactical enough. Ifit's not, I do have a lot I have a lotof written scripts that are out therethat you can copy and paste, so youdon't have to just rip the transcriptdown from all of Lenny's videos. Right?I do have written scripts and guides forthis, and I have a free course on how todo this, too, that's on YouTube. So,it's not like you're uh if you need theactual

01:40:26specifics, there are a lot ofscenarios I've already kind of coveredyou can go to.>> Amazing. And we'll link to all that. AndI think it's I asked you what you werehoping to get out of this uh before westarted recording. And uh just to beclear, you're not looking for newclients. You're booked up. You're youThis is like you share all of this stuffout there. You have this free course.You have all these Substack posts. So,so that's what I love about you. It'snot like, you know, you're trying toIt's not like some deal deal leaf flowhere.>> My mission is to make what I've learnedfrom very successful people moreaccessible.Right? And if you put a pay band on allof that, you're not making itaccessible. Right? In myhourly fees are very high. Right? So,it's like I don't want to push for thatandfeel like I'm unobtainable. So, I wantto give away as much as I can.Andit's These things shouldn't be gatekept.They often are.But um yeah, I was mentioned a littlebit in the green room. I just I felt alittle powerless growing up. Um therewas like some little substance abuse andtrauma as as I was growing up, and Inever felt comfortable or safe. And so,when Ibecame a little older, I started tounderstand psychology a little bitdifferently because the same fear I'dhave as a child,I could see in the boardroom. I couldsee

01:41:41the same fight or flight mechanisms,but that was far less scary.Right? So, it's just money. Money's likeI'm not going to get hit. Right?Nobody's going to get hurt here. Right?So, I could start to see that and Icould see the body language and I canunderstand when somebody was in a tensemoment. And all I ever wanted to dobecause I I felt that from a little kidwas help that person feel safe.Right? Help them feel safe in thatmoment. And so, I've been obsessed overhow to solve that for my entire career.First for myself,and then what became natural for me isfor other people cuz I could see theirgrowth, and that's what became mostfulfilling.>> There's a whole other conversation wecould have about that whole part of your>> We got to be careful about that one.Yeah.>> All right.>> That one I might start crying on thatone.>> Okay, well, that makes good content.That could be part two. Jacob, you're>> comments. Like next time make Jacob cry,Lenny. Go for the kill. Go for the kill.>> I I hope not. I don't think my peoplewant that. We'll see. Oh my god.UmOkay, before we get to our very excitinglightning round, Jacob, is thereanything else you want to share,anything else you want to leavelisteners with?>> Just that if if you're going to take achance, take a chance on yourself.I'm sure a lot of these folks areparents or a lot of these people are areare parents

01:42:56and you want toyou want to be the best version ofyourself and show that your kids thatyou could survive anything. You're goingto you're going to get a couple bruisesalong the way. Right? Like these aregreat first world problems to try tofight for.Right? Like it's not it's not going toit's not going to take away your home.It's not itThe thing isyou're only going to make life betteraround you. Right? If your cupoverfloweth, right? You'll be able togive more to others.So, it's not about am I worth it? Isthat It's likeif you are a generous person naturally,you can be more generous if you havemore wealth.Right? If you're afraid of wealth, thisis something that really screwed me up.Like I used to despise wealth.I despised it.Right? And I don't know why. It was likemiss like I didn't trust people withmoney. I felt like they all had to bedirty or they all had to do somethingand to be faira lot of people dothings that are highly questionable andunethical, right? And we see that in theworld around us.But if you fear it and you don'tunderstand it you'll never have anopportunity to change it.And so you need to take some chances onyourself with this and if I hopefullythat's another piece just having theconfidence to go out and try even if youfail, you're failing forward, you'relearning. Right? And

01:44:12you're going tofind a style that works best for you.It's not that Jacob Orwig's style is thestyle that's awesome or Lenny's style isa style. You don't need to copy anyoneelse. You need to find that center thatthat works well for you and what you'recomfortable.>> That is beautiful.Uh I'm also realizing as we're talkingwe haven't mentioned AI once in thisconversation. It's like>> Which is incredible. I love that.>> Listeners the listeners are like ohthank goodness.>> Yeah, that's how I feel.>> goodness.>> Just once in a while.>> It's cuz I don't want AI to replace meLenny. I don't want it.>> IYeah, I like I don't even know.Anyway, we're getting toOkay, well>> you speechless. That's the job. If youget the podcast host speechless, you'redoing your job. That's great.>> Okay, well we did it. With that Jacob wehave reached our very exciting lightninground. I've got five questions for you.Are you ready?>> All right, I will I'll do the best Ican, yeah.>> Here we go. What are two or three booksyou find yourself recommending most toother people?>> Influence by Robert Cialdini.>> Sweet that's the one.>> That's the one. I mean I like HerbCohen's You Can Negotiate Anything. It'sa little dated. Uhlike old white dude in the 80s dated so

01:45:27be mindful it doesn't suit allaudiences, but it's what I like about itis they talk about like negotiatingdishwashers and stuff, not like going tomarket with meta versus Instagram andthe acquisition. Like it's notcomplicated. It's like here's an appleand here's an orange and here's theconcept of negotiation really spelledout simple.I did just do a podcast with John Lowryand he wrote a book called negotiationmade simple.And I remember reading it and I waspissed offbecause I'm like I wanted to write abook a couple years ago and then I readhis and said this like this is what Iwanted to write.So I was frustrated and then I was likeI'm going to reach out to him because Ihave a lot of respect for him. So I didhis podcast that'll be live soon, butyeah, that was negotiation made simple.It really breaks it downin an easy way and I think that could belike a bible.And then I like radical candor. I knowsome of your guests put that on. I'vemet Kim Scott, she's phenomenal. Likethatradical candor really gave me theconfidence to be assertive in the waysthat I never had been before. So my wifetaught me that. Kim Scott embraced it inthe corporate world and like those twopieces like really helped elevate mycareer.>> I think radical candor is the secondmost mentioned book on this podcastbehind high output management.>> Yeah, I have not read that.

01:46:43Admittedly I'm bad at consuming content.I'm not I I only create. I've got thisrule that you create 10 times morecontent than you consume. So I read likeone book a year and now apparently I'mgoing to write one book.Somaybe that'll be the new goal.>> That's a great that's a great framework.Okay, next question. Do you have afavorite recent movie or TV show you'vereally enjoyed?>> I've been really liking watching Luca.The Disney movie.>> [snorts]>> Having a toddler and a newborn I reallyjust watch cartoons now. So I I actuallyfor low stimulating things I really likeMinuscule.It's like a a YouTube short that's likeFrench made and it's like spiders andflies and like bugs. Justvery low stimulation hanging around. Um>> That soundsnot>> [laughter]>> not appealing, but uh>> No, that's why it's so good becauseyou're so over stimulated having kidsthat it's so mellow. You can be like,oh, I actually get to think a littlebit.You know, like>> Okay.>> You know, finding finding a littleboredom and creative. Like that's howyou get creative. If you're constantlyif it's like Cocomelon and PAW Patroland you're like you can hear the beatsin your

01:47:58head that you can't do that. I'mnot going to I'm not I can't do that tomy kids.>> Uh, favorite recent product you'vediscovered that you love.>> Claude CoWork.I mean, I>> Good one.>> I loveClaude CoWork. I'm sorry for mentioningAI, but like I really only use a handfulof products, souh, Claude CoWork is one of them and uh,MacroFactorfor macro tracking and uh, I got a Whoopthis last year and I've lost almost 50lb just paying attention to my Whoopstats and like trying to sleep andyou could tell I'm a pretty obsessiveguy, so data like still geeks me out alittle bit on that, but uh, those arethe three products that I would useevery day and and a little bit ofGemini, too. Those are the two in myopinion winning the race.>> Do you have a favorite life motto thatyou find yourself coming back to in workor in life?>> Always give more than you expect toreceive.>> It's like a golden rule plus plus.>> That's that's how networking works.You don't you don't network with someonetrying to take.You say, how can I help you?And that's athat's a principle from Cialdini, also,right? And uhuh, How to Win Friends and InfluencePeople,right?That's not why I do it. I'm just I'mjust suggesting

01:49:13that's also a area where you can readmore on that.>> Final question, uh you've you'restarting a foundation. A non-profit.>> Yeah, I'm I'm working for or I I'm onthe board of the Cody Dieruf Foundationand that's in Bozeman, Montana. And whatwe do is uh my son has cystic fibrosis.Yeah, and cystic fibrosis is a geneticcondition. I'll actually talk a littlebit more about it in Predeterminedbecause his life was {quote}predetermined. We were not reallyaccepting that. Um but in with ourfoundation, we help rural parts ofMontana get access tothe health care that they need.Yeah, and so theythey got me with this. So like we wehelped this family this this woman shehad three boys. This is a sad story, sobear with me.Soone of her boys, 29 years old, needed alung transplant. This is what cysticfibrosis does. So made it to 29 is good.The life expectancy used to be 7 to 10years old.So made it to 29, needed a lungtransplant. She couldn't afford it.And her son passed away. She had twoother boys with cystic fibrosis.And then so her 27-year-old son, 2 yearsyounger,needed a lung transplant. And sheactually found out that

01:50:28our agencyexisted in that that period. And wefunded the life flight to DenverChildren's Hospital to get thatlife-saving surgery and saved her son'slife.Andthat sounds like a great story. The partthat got me was that now the mom feelsall this guilt because she could havesaved her son's life if she knew weexisted.And that part like I was in tearsthinking about that. UmI didI have talked a little bit about myson's diagnosis. Like it's not definingour life, but my wife and I prayed aboutthis and it wasif it would happen to anyone, it shouldhappen to us because if as soon as thathappened, I I made a handful of phonecalls. II did all this networking to be selfishand build my career and do these thingsand in that give before you ask it toreceive philosophy I've always kind oflived by that undersell over deliver.And within 24 hours of his diagnosis Ihad a phone call from the chief medicalofficer of Denver Children's Hospital atStanford and I got a call from the FDAthat said don't worry the sun your son'smedication is getting lower to one yearold and the Trikafta is going from sixto two. So he may never experience asymptom in his lifebecause this is changed now.Solike I felt this is immense blessing

01:51:44andsupport through that. So that's thefoundation we we support these ruralareas that don't have access to thathealth care.And then I've also started conversationswith the Cystic Fibrosis Foundationwhichreally helped funding they helped fundthe life-saving medication that changesthe life expectancy from 7 to 70 yearsold. Like they are expected to have fulllives now. So that's something I'm verypassionate about.>> Incredible.Oh man, there's so many so many thistopics and directions we could have gonewith this.UhJacob>> I know I blew you out. I blew you out ofthe water man. Sorry. I yeah I monologuelike nobody's business.>> There's this I've had I've had worse.Um okay, working folks find you onlineif they want to reach out maybe followup on some of this stuff and how canlisteners be useful to you?>> Listeners can be useful just byadvocating for themselves.Rising tide forever. That's important.Uh I don'tI guess I don't really have socialmedia. I deleted LinkedIn. Uh the post Iwrote about that kind of went viral onSubstack. It's cool. I share I think Ishared that one with you. Uh I haveexecsinthesity.comwhich yes is a play on Sex in the City.It's kind of explaining some of thethings that uh people are afraid to talkabout.

01:53:00So execsinthesity is my Substack.And I write once a week on Thursdaymorning and I sharelittle thoughts on what's happening.Occasionally I'll share case studies onwhat clients have done. I'll shareplay-by-plays and the actual scripts.That's also where I have a free jobsearch course. It's about 8 hours that Ifilmed and I sold for like a grand andnow I just give it away for free.That's also available on the YouTube,which is Execs in the City.Which I have like 100 subscribers, sodon't expect a lot of content for me.I'm not I'm not pumping out videocontent all the time.Um and then there's a small paid tier ifsomebody wants to get discounts oncoaching. They also get access to JacobGPT. Well, it's another AI I mentioned.It's digitally trained on I think youhave one, too, right?>> Yeah, Lenny bot.>> my content. Lenny bot. Yeah, so it'sit's like aJacob bot, which is a minor Lenny bot.Right? Trained on my content. Yeah, andum then I do some additional casestudies for them. Uh and then my actualbusiness is thinkwarwith.com,uh which just tells you outcomes thatthat we've been able to deliver. So, uhI'm not going to ask you for Instagramor anything like that. Just real simple.Try to keep it at Substack only, really.>> Jacob, this was awesome. Thank you somuch for being here.>> Thank you, Lenny. I appreciate the timetoday and again

01:54:15I was real giddy aboutit and your motto was to have fun. I hada lot of fun today. Thank you.>> That's right. Here we go. People don'tsee this if they're waiting till the endof this podcast. I have this littlepocket I show all the guests that ourgoal is to have fun.Uh so, Easter egg. All right, Jacob,thank you so much. Bye, everyone.Thank you so much for listening. If youfound this valuable, you can subscribeto the show on Apple Podcasts, Spotify,or your favorite podcast app.Also, please consider giving us a ratingor leaving a review [music] as thatreally helps other listeners find thepodcast. You can find all past episodesor learn more about the show atlennyspodcast.com.See you in the next episode.