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At the executive level, that high up. You don’t get paid in salary. You get paid in equity. Your negotiations should be around equity and its valuations. You sh

At the executive level, that high up. You don’t get paid in salary. You get paid in equity. Your negotiations should be around equity and its valuations. You should be arguing for compensation packages of “if I grow x by y. You give me Z in equity.” I am not an executive. I am cashing out over 500k in equity, and a yearly salary of 250k+ per year as an independent contributor. Last year my income cleared 400k. Your focus on salary; and not on VALUE, negotiations, equity, vesting, growth, and goals are what’s holding you back. Once you hit that, then you need to change how you use money. Such as negotiating that equity be deposited in a self-directed IRA to sell it, and invest it with little tax penalty. At 200k in most areas of the United States you could have paid off a house in a year. If you’ve made 200k a year for 10 years; banking 50k of that in an index fund would have paid big dividends. Let alone using 50k on a construction loan to build a multi family house. Then rent that out providing affordable housing to folks. Or even, just pledging your equity as collateral to get the loan. You’re not a wage slave. But you’re acting like you are one. Stop, you have access to more resources than the probably 5% of America. Use those tools, change your mindset, get a proper accountant, and do some personal planning and growth.

gsibble 4y ago
I live in San Francisco man. Houses cost $1.5-4 million. Do you have any idea how expensive it is to live here? Maybe that's what's missing from the context.
- digi59404 4y ago
  Absolutely. In 2012 I lived in Antioch/Pittsburg and made 13$/Hour. I live in TN now and own an entire mountain for a fraction of that cost. Yet, I can be in Downtown SF in 6 hours. Even if I was in SF. That doesn’t mean you have to live on the peninsula. And yes; I fully understand the opportunity cost of not being in the heart of SF. My point here isn’t to be a dick of judgemental. Even if my tone may be that way. It’s to explain that I think you’re missing the bigger picture here and you’re missing some information. Your equity should be worth way more. Even if the cash value is low, equity can be leveraged in funny ways to provide value that’s not monetary. I don’t think I’ve met a CTO/CFO that has a compensation plan that is north of 250k in salary. Yet, I was behind a CFO a few years back who literally bought a house in France with equity. When you hit the levels and roles you’ve held. When you hit 200k+ income. The entire game changes. There’s a point from around 0-80k/year where the rules are one way. From 80-200k where the rules are another way. 200k+ the game is entirely different. I’ve been through each stage and had to learn it. At 200k+ as an executive. You have way more tools at your disposal than you would at IC sub 200k levels. I sat at a bar two weeks ago with a CTO who made south of 200k/year. Who just bought his third house that was north of a million dollars, this became his spring house in Hilton Head SC. The value of money is not always in dollar amounts. From this post and some of your comments here that seems like what you’re focused on. It may not be, but I really encourage you to explore this topic more. You may be the best fucking CTO in SF. But if you can’t articulate, negotiate, and get what your real value is, in a structured deal. You’re just going to be leaving money at the table. As CTO you wield immense power, with the org, and the board. Your position guarantees you a seat at the table with an audience. Use it to your advantage to get the value you deserve, and use it to make sure they know that the toxic culture they perpetuate will cause a loss in value of the company.
  - gsibble 4y ago
    I tried. As I said in another comment, as Chief Software Architect at one company, I built them a bank and added $800 million to their valuation. I asked for more salary and equity and was denied both over the course of 6 months. So I quit. You know what happened? The product failed. They lost all their customers. And they had to scrap it, hire a team of 15, start from scratch, and do a down round where they lost $600 million in valuation. All because they wouldn't give me a raise and more equity. I'VE TRIED!!!!!!!!! I've tried so many times! I've begged and pleaded! I've shown my worth! And every company I leave quickly goes out of business because they don't realize how critical I am. And no one will give me the cash or equity I deserve. So you were saying?
    - digi59404 4y ago
      My friend, just because you have the skills and ability. Does not mean you have the tools and opportunity. Just because you think you have the skills, doesn’t mean you do. Operating at that level is less about your technical skills and more about your soft skills. Take this thread for example. You’re getting defensive. I can understand why here. But if you get defensive like this in front of senior leadership. You’re going to lose credibility and trust from them. When you bring them a technical solution that works. They will ignore it because of that. They will also in their minds see less value in your skills. You can be the best software architect in the world. But if you don’t have the soft skills. You won’t be respected as anything other than a replaceable IC.
      - gsibble 4y ago
        Please don't misinterpret my online comments as how I act in real life, lol. I'm very professional. I get fantastic, absolutely stellar performance reviews at every company. At the bank, they were required to put one negative thing on the performance review. You know what the CTO wrote? "Miscapitalized ID in 'cardID' variable name". That was the worst thing they could come up with about my performance. And they still denied me any pay or equity raise. And it cost them $600 million.
- plint 4y ago
  In your area. Ask the people who provide the most basic and fundamental services around you how they get by. The cashier at the supermarket. The waiter at your restaurant. The pizza delivery guy. I promise you, one, they are not anywhere close to making 200k. And I'm sure plenty of them have kids, family they need to provide for. I comprehend the issue in terms of degrees of freedom. How free, how autonomous are you compared to the cashier at the supermarket? Choose your dimensions. Choice of work, choice of shelter, choice of food. Maslow's hierarchy of needs. Try your best to objectively evaluate your freedom in the dimensions that matter to you. Then compare to your chosen reference worker/s. Cashier, delivery guy, warehouse worker, office worker, etc. To claim that you are a wage slave is to claim that you have even less freedom than the rest of us. So analyze it carefully. And if you do reach the conclusion that the guy working the checkouts has more freedom than you, the logical conclusion is for you to quit your 4 hours a week, 200k job and become a checkout worker, no? Well, I'm sure you'll have no interviewing problems there.
- deleted 4y ago
  [deleted]
gsibble 4y ago
And wait, how are you being paid in equity without a cash out event? Is every company you're working for a success? None of what you are saying makes any sense. And of course I asked for more equity. They denied that too.
- digi59404 4y ago
  You don’t ask for more equity. You make them give it to you by providing so much value that if they even hint that you’ll leave. They’ll double the offer. I interviewed with a company last month who when I stepped away from the offer table. They almost doubled their equity offer. Even at a low valuation it would have been north of 500k. The power of equity is not in its cash value my friend. Equity is a huge stick, and how you use it matters. For example; you can do a forward contract on your equity to delay taxes, and get a cash out without selling the equity. How you structure that deal helps and can be advantageous. You can use equity as collateral for loans. IE using equity to buy a house in SF for 10-20% down with a huge balloon payment at the end. Backed by equity. In which you then sell the house before the balloon payment hits, you keep the equity, and you also earn equity from the sale of the house. You can do construction loans backed by equity on new homes. Then sell them for profit. You can do the same with multi-family homes, providing affordable living conditions for folks while taking a chunk off the top. I really suggest you sit down with an accountant specializing in these things. From your blog you’ve dealt with funds and fundraising. You may understand it from inside a business. You need to understand it from the side of a sales rep or rich individual.
  - gsibble 4y ago
    I did leave. They lost hundreds of millions in valuation in a down round. Companies rarely understood the value I brought to them. You clearly do not understand.
    - digi59404 4y ago
      My friend, and I say this without trying to be judgemental or rude.. If no one in the room understands the value you bring to the table. The problem does not lie with them. It lies with your ability to communicate and sell that value.

gsibble 4y ago

I live in San Francisco man. Houses cost $1.5-4 million. Do you have any idea how expensive it is to live here? Maybe that's what's missing from the context.

digi59404 4y ago
Absolutely. In 2012 I lived in Antioch/Pittsburg and made 13$/Hour. I live in TN now and own an entire mountain for a fraction of that cost. Yet, I can be in Downtown SF in 6 hours. Even if I was in SF. That doesn’t mean you have to live on the peninsula. And yes; I fully understand the opportunity cost of not being in the heart of SF. My point here isn’t to be a dick of judgemental. Even if my tone may be that way. It’s to explain that I think you’re missing the bigger picture here and you’re missing some information. Your equity should be worth way more. Even if the cash value is low, equity can be leveraged in funny ways to provide value that’s not monetary. I don’t think I’ve met a CTO/CFO that has a compensation plan that is north of 250k in salary. Yet, I was behind a CFO a few years back who literally bought a house in France with equity. When you hit the levels and roles you’ve held. When you hit 200k+ income. The entire game changes. There’s a point from around 0-80k/year where the rules are one way. From 80-200k where the rules are another way. 200k+ the game is entirely different. I’ve been through each stage and had to learn it. At 200k+ as an executive. You have way more tools at your disposal than you would at IC sub 200k levels. I sat at a bar two weeks ago with a CTO who made south of 200k/year. Who just bought his third house that was north of a million dollars, this became his spring house in Hilton Head SC. The value of money is not always in dollar amounts. From this post and some of your comments here that seems like what you’re focused on. It may not be, but I really encourage you to explore this topic more. You may be the best fucking CTO in SF. But if you can’t articulate, negotiate, and get what your real value is, in a structured deal. You’re just going to be leaving money at the table. As CTO you wield immense power, with the org, and the board. Your position guarantees you a seat at the table with an audience. Use it to your advantage to get the value you deserve, and use it to make sure they know that the toxic culture they perpetuate will cause a loss in value of the company.
- gsibble 4y ago
  I tried. As I said in another comment, as Chief Software Architect at one company, I built them a bank and added $800 million to their valuation. I asked for more salary and equity and was denied both over the course of 6 months. So I quit. You know what happened? The product failed. They lost all their customers. And they had to scrap it, hire a team of 15, start from scratch, and do a down round where they lost $600 million in valuation. All because they wouldn't give me a raise and more equity. I'VE TRIED!!!!!!!!! I've tried so many times! I've begged and pleaded! I've shown my worth! And every company I leave quickly goes out of business because they don't realize how critical I am. And no one will give me the cash or equity I deserve. So you were saying?
  - digi59404 4y ago
    My friend, just because you have the skills and ability. Does not mean you have the tools and opportunity. Just because you think you have the skills, doesn’t mean you do. Operating at that level is less about your technical skills and more about your soft skills. Take this thread for example. You’re getting defensive. I can understand why here. But if you get defensive like this in front of senior leadership. You’re going to lose credibility and trust from them. When you bring them a technical solution that works. They will ignore it because of that. They will also in their minds see less value in your skills. You can be the best software architect in the world. But if you don’t have the soft skills. You won’t be respected as anything other than a replaceable IC.
    - gsibble 4y ago
      Please don't misinterpret my online comments as how I act in real life, lol. I'm very professional. I get fantastic, absolutely stellar performance reviews at every company. At the bank, they were required to put one negative thing on the performance review. You know what the CTO wrote? "Miscapitalized ID in 'cardID' variable name". That was the worst thing they could come up with about my performance. And they still denied me any pay or equity raise. And it cost them $600 million.
plint 4y ago
In your area. Ask the people who provide the most basic and fundamental services around you how they get by. The cashier at the supermarket. The waiter at your restaurant. The pizza delivery guy. I promise you, one, they are not anywhere close to making 200k. And I'm sure plenty of them have kids, family they need to provide for. I comprehend the issue in terms of degrees of freedom. How free, how autonomous are you compared to the cashier at the supermarket? Choose your dimensions. Choice of work, choice of shelter, choice of food. Maslow's hierarchy of needs. Try your best to objectively evaluate your freedom in the dimensions that matter to you. Then compare to your chosen reference worker/s. Cashier, delivery guy, warehouse worker, office worker, etc. To claim that you are a wage slave is to claim that you have even less freedom than the rest of us. So analyze it carefully. And if you do reach the conclusion that the guy working the checkouts has more freedom than you, the logical conclusion is for you to quit your 4 hours a week, 200k job and become a checkout worker, no? Well, I'm sure you'll have no interviewing problems there.
deleted 4y ago
[deleted]

gsibble 4y ago

And wait, how are you being paid in equity without a cash out event? Is every company you're working for a success? None of what you are saying makes any sense. And of course I asked for more equity. They denied that too.

digi59404 4y ago
You don’t ask for more equity. You make them give it to you by providing so much value that if they even hint that you’ll leave. They’ll double the offer. I interviewed with a company last month who when I stepped away from the offer table. They almost doubled their equity offer. Even at a low valuation it would have been north of 500k. The power of equity is not in its cash value my friend. Equity is a huge stick, and how you use it matters. For example; you can do a forward contract on your equity to delay taxes, and get a cash out without selling the equity. How you structure that deal helps and can be advantageous. You can use equity as collateral for loans. IE using equity to buy a house in SF for 10-20% down with a huge balloon payment at the end. Backed by equity. In which you then sell the house before the balloon payment hits, you keep the equity, and you also earn equity from the sale of the house. You can do construction loans backed by equity on new homes. Then sell them for profit. You can do the same with multi-family homes, providing affordable living conditions for folks while taking a chunk off the top. I really suggest you sit down with an accountant specializing in these things. From your blog you’ve dealt with funds and fundraising. You may understand it from inside a business. You need to understand it from the side of a sales rep or rich individual.
- gsibble 4y ago
  I did leave. They lost hundreds of millions in valuation in a down round. Companies rarely understood the value I brought to them. You clearly do not understand.
  - digi59404 4y ago
    My friend, and I say this without trying to be judgemental or rude.. If no one in the room understands the value you bring to the table. The problem does not lie with them. It lies with your ability to communicate and sell that value.