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Well to be fair, what I listed in the original post are all of his negative traits. Nothing is ever purely black or white after all.
His positive traits:
1. As bad as he is to people he considers somehow beneath him, he is very good to people he considers high quality. He treats his co-founders extremely well and is very good to his family. At the age of 30, he was already a multi-millionaire and buys lavish gifts for those close to him. His closest friends all love him to death (even though they all recognize how ridiculous he can be).
2. He has an exceptional talent in bringing on other talented people. As a matter of fact, the big reason I'm considering taking the job is not because of him but because of his two co-founders: his exceptionally talented Biz Dev guy and his MIT-educated CTO who does a fantastic job running a 40-man engineering/design team. With these two on board, it makes life so easy for the rest of the team. In addition, he has great connections with SV and LA moneymen and just a month or two ago, he used these connections to help a Hollywood celebrity out with some debt issues. He is actually quite good at what he does...which I don't know how to explain precisely...
3. He would give me his last dollar even if he was starving. I truly do believe this. But if he saw a starving kid on the street and had all the money in the world? Wouldn't even give him a dime. I think this sums him up better than any other way to describe him...very good to people he cares about and a complete dick to those he doesn't.
Yes, when push comes to shove, he is going to expect me to perform. That's the same at any company. He will be more manipulative and pushy about it. That's something I'll already know going into this.
you've been given plenty of advice and the decision is up to you at this point. It sounds like you've made up your mind and you're just looking for validation that you're making the right decision. We can't really give you that - most on here have said what the pitfalls could be but no one can see the future.
I wouldn't do it. When I was younger I was at a similar place (different circumstances and not the same method of behavior of people but comparable). It was a mistake. This will be your life and my very strong guess is that you won't like your life much. That was my experience and I left.
I'd do something else and remain friends with the guy and keep as good connections as I could. A mentor type thing maybe and keep the door open for the future. But like I said, I wouldn't do it. My guess though is that you will. The best way to handle things like this is to be who you know you are and if you have a good and close relationship with this guy, then be ok telling him when he's out of line. He knows when he's out of line anyway so it won't be a surprise to him and I'm sure he'll like hearing it. Like if you are at a restaurant and he's a dbag to the wait staff, ask him why he's a dbag to them or tell him that he is. It'll make him happy, believe me. And, he'll respect you (I would guess). People like that like others who aren't afraid to tell them that they are aholes and know they need others around who are strong and can snap them out of their BS and emotional outbursts. Point #2 BTW is not unusual or bad IMO - it's business and how to win contracts. Many orgs have a "win the contract, then figure out how to do the work or deliver on time" method. It's shady and that's how your life will feel if you sign on - shady and uncomfortable. And you'll feel that way when you're not at work too and for a while after you leave (which you will).
I have an incredible offer from a startup that would double my salary and give me a sizeable chunk of equity
He tells a lot of half-truths. They're not always full-out lies. To him, it's a necessary strategy in today's hyper-competitive business environment. The ends (getting the business) justify the means.
Having a lot of equity hanging on this person is very dangerous. Do whatever you want, but people like this will turn on you in a heartbeat. Nobody is their friend when it comes to getting what they want.
The psychotic "I'll have everyone fired" stuff is more childish than anything. That's not good either.
I have an incredible offer from a startup that would double my salary and give me a sizeable chunk of equity, which is extraordinary for someone like me who doesn't have any experience in tech startups. It came purely from connections I've made over the past year, primarily the CEO who really likes me and considers me "family."
My only hesitation is that he has a very aggressive personality and does a lot of things that I find bothersome at a personal level. Professionally, he is extremely good at what he does. I feel like I could learn so much by just watching him in action. However, he has no off-switch when he's not working and this is what makes him hard to be around. I guess the very traits that make him so successful at running companies are the very traits that make him a nightmare outside of work. For instance,
1. He has very little patience. He's always going off on waiters at restaurants for forgetting a minute detail of his order ("3 lemons? I asked for 4, you moron. You have literally one job and you can't even do it right? One phone call and I could have you replaced.") It's very uncomfortable to be around him when he does this, which happens several times a day.
2. He tells a lot of half-truths. They're not always full-out lies. It's just enough to make most of us uncomfortable. For example, his strategy in closing a deal a month or so ago was to promise to deliver a product faster than the competitors and for less money. His entire team told him it wouldn't be possible to finish that early or do it for that cheap. He barely listened to them. He told me, however, that a few months after the client signed the contract, he would then tell them that the product required more time or more money, at which point the client would be better off sticking with him instead of starting all over again with a different company. To me, this comes off as disingenuous. To him, it's a necessary strategy in today's hyper-competitive business environment. The ends (getting the business) justify the means.
3. He is extremely pushy, emotionally manipulative, and feels absolutely justified in everything he does.
BUT, he treats me like gold. He trusts me with very intimate details about his life and all the various things going on in his private life...things he hadn't and wouldn't even tell his co-founders whom he has known for 10+ years. Plus, I've already learned so much about business and life in general from watching him operate. His pushiness has gotten us access to some very exclusive events and social circles where we hobnobbed with the 1%, which I have never been a part of before in my life. He called up an airline recently and threatened to have every customer service agent fired if they didn't immediately refund me AND upgrade my flight to first class because my flight was delayed a few hours and I missed my connection (I've become very careful in what I tell him now...) And on top of all that, the company itself is flourishing and I would be in a great position financially.
Am I just being stupid to even debate this? I'm getting the offer of a lifetime with a person who goes out of his way to look out for me and I'm having major moral hangups.
OMG you have found the office Dilbert works in!!
Actually if (After you listed the positives of this guy) you might try it for a year....
I have an incredible offer from a startup that would double my salary and give me a sizeable chunk of equity, which is extraordinary for someone like me who doesn't have any experience in tech startups. It came purely from connections I've made over the past year, primarily the CEO who really likes me and considers me "family."
My only hesitation is that he has a very aggressive personality and does a lot of things that I find bothersome at a personal level. Professionally, he is extremely good at what he does. I feel like I could learn so much by just watching him in action. However, he has no off-switch when he's not working and this is what makes him hard to be around. I guess the very traits that make him so successful at running companies are the very traits that make him a nightmare outside of work. For instance,
1. He has very little patience. He's always going off on waiters at restaurants for forgetting a minute detail of his order ("3 lemons? I asked for 4, you moron. You have literally one job and you can't even do it right? One phone call and I could have you replaced.") It's very uncomfortable to be around him when he does this, which happens several times a day.
2. He tells a lot of half-truths. They're not always full-out lies. It's just enough to make most of us uncomfortable. For example, his strategy in closing a deal a month or so ago was to promise to deliver a product faster than the competitors and for less money. His entire team told him it wouldn't be possible to finish that early or do it for that cheap. He barely listened to them. He told me, however, that a few months after the client signed the contract, he would then tell them that the product required more time or more money, at which point the client would be better off sticking with him instead of starting all over again with a different company. To me, this comes off as disingenuous. To him, it's a necessary strategy in today's hyper-competitive business environment. The ends (getting the business) justify the means.
3. He is extremely pushy, emotionally manipulative, and feels absolutely justified in everything he does.
BUT, he treats me like gold. He trusts me with very intimate details about his life and all the various things going on in his private life...things he hadn't and wouldn't even tell his co-founders whom he has known for 10+ years. Plus, I've already learned so much about business and life in general from watching him operate. His pushiness has gotten us access to some very exclusive events and social circles where we hobnobbed with the 1%, which I have never been a part of before in my life. He called up an airline recently and threatened to have every customer service agent fired if they didn't immediately refund me AND upgrade my flight to first class because my flight was delayed a few hours and I missed my connection (I've become very careful in what I tell him now...) And on top of all that, the company itself is flourishing and I would be in a great position financially.
Am I just being stupid to even debate this? I'm getting the offer of a lifetime with a person who goes out of his way to look out for me and I'm having major moral hangups.
Uh---this isn't Donald Trump,is it? Oh wait, you said "startup..."
1. He has very little patience. He's always going off on waiters at restaurants for forgetting a minute detail of his order ("3 lemons? I asked for 4, you moron. You have literally one job and you can't even do it right? One phone call and I could have you replaced.") It's very uncomfortable to be around him when he does this, which happens several times a day.
I learned long ago that you never ever insult the waiter. Instant karma awaits.
It depends on your savings and own financial situation. We had a guy leave from an admin assistant job to go be a Director of Marketing at some start up. Four months into it the company failed and shut down. Now he is unemployed, and trust me, the guy doesn't have a ton of options. MBA from no name school with no skills, it's not going to inspire confidence when people see he is 40 and he's only really been an admin assistant his entire life.
I have an incredible offer from a startup that would double my salary and give me a sizeable chunk of equity, which is extraordinary for someone like me who doesn't have any experience in tech startups. It came purely from connections I've made over the past year, primarily the CEO who really likes me and considers me "family."
My only hesitation is that he has a very aggressive personality and does a lot of things that I find bothersome at a personal level. Professionally, he is extremely good at what he does. I feel like I could learn so much by just watching him in action. However, he has no off-switch when he's not working and this is what makes him hard to be around. I guess the very traits that make him so successful at running companies are the very traits that make him a nightmare outside of work. For instance,
1. He has very little patience. He's always going off on waiters at restaurants for forgetting a minute detail of his order ("3 lemons? I asked for 4, you moron. You have literally one job and you can't even do it right? One phone call and I could have you replaced.") It's very uncomfortable to be around him when he does this, which happens several times a day.
2. He tells a lot of half-truths. They're not always full-out lies. It's just enough to make most of us uncomfortable. For example, his strategy in closing a deal a month or so ago was to promise to deliver a product faster than the competitors and for less money. His entire team told him it wouldn't be possible to finish that early or do it for that cheap. He barely listened to them. He told me, however, that a few months after the client signed the contract, he would then tell them that the product required more time or more money, at which point the client would be better off sticking with him instead of starting all over again with a different company. To me, this comes off as disingenuous. To him, it's a necessary strategy in today's hyper-competitive business environment. The ends (getting the business) justify the means.
3. He is extremely pushy, emotionally manipulative, and feels absolutely justified in everything he does.
BUT, he treats me like gold. He trusts me with very intimate details about his life and all the various things going on in his private life...things he hadn't and wouldn't even tell his co-founders whom he has known for 10+ years. Plus, I've already learned so much about business and life in general from watching him operate. His pushiness has gotten us access to some very exclusive events and social circles where we hobnobbed with the 1%, which I have never been a part of before in my life. He called up an airline recently and threatened to have every customer service agent fired if they didn't immediately refund me AND upgrade my flight to first class because my flight was delayed a few hours and I missed my connection (I've become very careful in what I tell him now...) And on top of all that, the company itself is flourishing and I would be in a great position financially.
Am I just being stupid to even debate this? I'm getting the offer of a lifetime with a person who goes out of his way to look out for me and I'm having major moral hangups.
Every part of what you have written is exploding with the suggestion that this man is a narcissist. I shall elaborate.
He bullies: service workers and anybody else in his way. That isn't random abuse, that is by design. He does so to boost his ego.
He lies: half-truths are still lies. He's just telling the truth sometimes and lying behind it. That's called lying. Your instinct and intuition already confirms that he is a liar.
He flirts: he is treating you nicely so you can be his friend. God knows how many others he has left behind him. You'll be no exception.
He feels absolutely justified: He, I expect, will not accept critique. He is "always right" and will send scorn if you try to put through your lowly point of view. If it's someone else with more status, then he may suddenly bend.
He treats you like gold: And others like crap, clearly. Intimate things you should have no access to. But why would anyone respectful do that? And why should you believe that he's even telling the truth about these people, about money, anything? Would you really be in a better financial situation? As far as he's concerned, he has chalked you up as a best buddy for life. How long til he starts asking for a little cash his way, just for "investment purposes" during a "bad time"? Then more and more? And then suddenly it all falls flat on its face and he's sorry, but so long.
So if you take this job, feel free to be bullied, exploited, and manipulated. This is no startup, it's a trap from beginning to end. And if he really considers you family - ask what happened to his last one. But the promise of wealth and the crushing of others, including any critical response, is a dead giveaway. Get the hell out of there.
Does this firm have venture investors? Check VC websites.
Just guessing now... VC firms expect 1/3-1/2 of the firms they throw money at will fail even after vetting the business plan and executives. Those that do survive are more often purchased by other corporations (essentially buying the R&D) than taken public. Don't get glassy eyed, employees except for key founders, don't get a bouquet in a buy-out.
Has this executive developed other venture businesses? Check his resume just as you would if you were to hire HIM.
The executive you are describing has some of the personality traits of Steve Jobs and Travis Kalanick. Let me assure you that many of their early employees did not end up with big paychecks or a hunk of stock.
IF the firm has significant venture capital interest and you have an exit plan if the relationship turns bad then go for it, otherwise pass on this opportunity.
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