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Robert Maynard’s Essential Venture 
Capital Terms
Preferred stock - a class of 
ownership that has rights not 
ascribed to common shares. Usually 
a liquidation preference or a 
participating preference, voting 
preference or dilution preference. 
(terms defined below) Do not, 
under any circumstances, give a 
dilution preference.
parre passu - latin for “we all get 
what the other gets.” ( I take some 
literary license here). IOW, if one 
class of stock is going to get diluted, 
everyone is getting diluted at the 
same rate. Insist on this in any deal 
you make.
Liquidation preference - if the company 
sells, the stock with a liquidation 
preference gets all their money back 
before the remaining proceeds are split. 
Sometimes they get more than their 
money back. For instance, a 1X 
liquidation preference gets the amount 
they put in back first. A 2X gets twice 
the amount and so on. This is usually a 
big deal only if the company does not 
perform well.
Participating Preferred - a clause on 
Preferred Stock that allows the holder to 
be paid back his money, or some 
multiple thereof, when the company is 
sold. For instance, a 3X participating 
preferred share would get three times 
what he put in before common 
shareholders get paid. Participation 
usually falls off in the event of an IPO. I 
would never give more than 1X 
Participation.
Observation rights - The right for an 
investor to sit in on all board meetings 
and exec committee meetings without 
actually being on the board. Many VC’s 
are taking positions like this instead of 
board seats in order to mitigate liability. 
You can often counter a request for a 
board seat with observation rights. Say 
he wants two board seats out of five. 
Counter one with one observer. They’ll 
usually take that.
Vesting - award of ownership or 
options over a period of time. Set it 
in months rather than years. Thus, a 
three year option would vest 1/36th 
per month.
Reverse vesting - When the founders are 
stripped of their ownership rights of some 
amount of their founding stock (usually half) 
at the inception of the A round and they have 
to re-earn it over the vesting period. Do not 
make these options, make sure they remain 
as stock and that you control the voting rights 
even though they’re not vested. Don’t be 
offended or frightened off by this. It is a 
standard golden handcuff to ensure that the 
main guys they are investing in stay the 
course.
pre-money valuation - the 
enterprise value of the company 
without the investment. Let’s say 
$8mm.
post-money valuation - the 
enterprise value plus the amount of 
the investment. If you get $2mm in 
investment and your pre-money 
valuation is $8mm, then your post-money 
is $10mm.
tranches (pronounced “traunches”) a 
staging of the investment dollars subject 
to hitting specific performance goals. 
Do not, for any reason, do this. If it’s a 
deal point, walk away. This is a great 
way to get screwed. They’ll make it 
sound so reasonable, but it’s just a 
recipe for disaster because nothing goes 
according to plan, so they can always 
renegotiate the terms of the deal when 
you run out of cash. (Many do).
Option Pool - usually the investor will want to set aside 25% 
of the equity of the company in an option pool to be split by 
employees. I use a different bonus structure for my guys that 
is very well received and much less expensive for the owners. 
Basically, they get a dollar-for-dollar bonus on every dollar 
they were ever paid during their tenure six months after a 
change in control. They must be continuously employed and 
be employed on the payment date. I find that rank and file 
love this because it gives them a hard number to look to. If 
you pay them market rates (I always do) then this is a fair 
distribution in return for the work they had to do as a 
startup. It is MUCH cheaper for the owners/founders, is 
much less distracting from a management perspective and 
serves as a poison pill for someone who wants to buy you 
cheap. I save equity awards for C-Suite execs and Directors.
Strike Price - the amount paid for a share of 
stock when an option is exercised. The value 
of the compensation is the market value - 
strike price. Always make the strike price the 
same as the last round of financing or more. 
There is no need to provide cheap options 
anymore. Indeed, accounting for cheap 
options is a nightmare. If you're bringing 
someone on after the first investment is 
made, price the option at whatever the 
investor paid for his shares.
Rule 144 shares - You have to hold this stock for a 
year (if the company is public) before you can trade 
it. This is especially important in the case of options 
in that you will be taxed for the value of the 
compensation at the time you exercise the options, 
but you will not be able to trade for a year. This 
means that you come out of pocket to buy the stock 
and pay the taxes a year before you get the money 
from the sale of the shares, all the while taking the 
market risk on the appreciation of the shares. This 
is a hidden poison pill that makes options almost 
impossible for normal people to take advantage of. 
A good VC would never try this, but an unscrupulous 
investor or acquirer might.
Rule 8A - the filing that makes 
options tradeable immediately so 
that you can exercise your option 
and sell it on the same day. Insist 
that there is a clause in any vested 
options you give that force an 8A 
filing at some trip point, usually six 
months after an IPO.
Exercise date - the amount of time you have 
to buy your vested options before they are 
retrieved by the company should you leave 
before a liquidity event. Remember that, 
unless you’re public, these options will be 
treated as rule 144 stock until the stock is 
registered and publicly traded. This is a very 
important component of comp plans. Even if 
you vest, if you can’t afford to exercise and 
pay taxes, you lose the vested options if you 
leave.
Due diligence - They will look up 
your ass and out your eyes. Don’t 
get offended when they ask the 
same question 15 times. They're 
not stupid (usually), they're just 
trying to see if you've thought 
through all sides.
Cap Table - the list of who owns what in 
the company, how much they paid, 
when they paid, what they paid with 
(cash or services) their tax id #s, contact 
info including phone, email and hard 
address as well as any vesting schedule. 
Once this is published after a funding, it 
is almost impossible to change. Make 
sure it's right from day one and that it is 
kept completely up to date.
Deferred compensation - if you have been 
taking a smaller than market (or no) salary 
(this should be true of any of the execs at 
seed stage) make sure you record the full 
market salary as an expense and setup a 
liability account called deferred comp for that 
amount that is not paid in cash. This account 
would be paid on closing of the round (or 
some negotiation about it). It’s a good way to 
get your market rate even though you haven’t 
been taking it the whole time.
Board meetings - do not agree to any more than 
four formal meetings a year. Otherwise, you will be 
spending your days doing decks for the board rather 
than running the business. However, communicate 
with your board at least every month in writing with 
financials, waterfall reports, good bad and ugly 
developments. Remember to always communicate 
bad news early and loudly. No one expects you to 
be perfect and anyone on your board should be 
experienced enough to understand the rough times. 
Indeed, they are there to help you through them, 
not to whip you when they happen.
Accredited investor: Someone who has earned $200k per year for the 
past two years if single, $300k per year for two years if married or has 
$1mm in net investible assets excluding their home. (There are other 
requirements for things like trusts, corporations, etc. Your lawyer can 
help you with these) You want to ensure that all of your investors are 
accredited for two reasons: first and foremost: you should never take a 
dollar from someone who can’t afford to lose it. Chances are you’re 
going to fail. When people can’t lose the money and don’t understand 
the risk, they get very upset, file lawsuits, make noise on social media 
and just generally try to ruin your reputation. Don’t ever take money 
from people who can’t afford it. Stress in your presentations that the 
money is completely at risk. I liken it to putting it all on Red 00 in 
roulette. You’re either going to win big or lose it all. The second reason 
is for regulatory purposes. Different states have different rules for 
registering if your investor pool is not entirely accredited. The rules are 
basically the same as being public. No startup can afford that type of 
regulatory cost.
Term Sheet: This is the non-binding 
agreement that the VC will give you if 
he's ready to proceed to making a deal. 
It outlines the basic terms (wow, what a 
circular definition) of the deal. Get the 
term sheet right, but don't over-complicate 
it. It should be produced on 
one sheet of paper. Remember that it's 
non-binding, so you don't have to get 
crazy with legal language.
No-look: This is a term of time 
when you agree not to shop your 
deal to any other VC's. For the most 
part, this is a bad idea, especially if 
you are not cash-flowing. Under no 
circumstance give this away without 
getting something in return 
(expedited diligence, breakup fee if 
they don't fund, more elastic terms, 
higher valuation, something).
Seed Round: This is the tranche of money 
you raise, usually from yourself or friends and 
family, that is used to get a working product 
put together and get a little traction in the 
marketplace. You usually have to get to 
something like $50-100k per month in 
revenues on your seed round with a good 
growth trajectory in order to attract a good 
VC. Consider this the proof-of-concept stage. 
This is by far the hardest money to raise. 
Treat every dollar as if it were worth $100.
Series A Round: This is the tranche where you get your first 
one or two good VC's. It's usually priced at about 20% - 25% 
of the overall company (meaning, you get $2.5mm and they 
get 25% or whatever the ratio ends up being). With this 
money, you should be able to prove out that there is a viable 
market for your product and that you have the ability to 
penetrate it. I personally believe that you should have a 
viable business when you run out of A money. That is, if you 
had to, you could turn off the growth engine and have a 
business that cash flows. It's growth that costs money. If 
you're not able to raise another round of financing, you'd 
better be able to stop growing and live on what you've killed. 
The big lesson here is treat every dollar as if it's worth ten. 
Do NOT get crazy with hiring at this point, especially 
administrative types.
Series B Round: This is the tranche where 
you turn on full afterburner. You've proven 
the market exists and that your product is 
accepted. You've proven that you have the 
team that can exploit the market. Series B is 
where you lay on the staff to make it a big 
business. You should have an operating 
business when this money runs out, including 
financing the growth engine. Typically, VC's 
will get 15% of the company for a B round 
and the amount can be as high as $200mm. 
Whatever it is, it will be a big number, usually 
8-10X of your A round.
Series C and beyond: These rounds are saved so 
that you have a big business that is ready to go 
public or be bought for big dollars. Your executive 
team is well established. You may want to use some 
of this money to go into new products or buy 
another company. Whatever it is, be careful taking 
this money. If you're a hot company, everyone will 
want to give it to you, but it's easy to get over-diluted. 
It's also easy to let the success go to your 
head. Don't be afraid to cash out a bit if you take a 
C round. Meaning, sell a bit of your stock to the 
investor so that you're diversifying and put some 
cash in your pocket. They might give you a bit of 
grief for it at first, but it's not an unusual use of 
proceeds for a later round.

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Robert Maynard's Essential Venture Capital Terms

  • 1. Robert Maynard’s Essential Venture Capital Terms
  • 2. Preferred stock - a class of ownership that has rights not ascribed to common shares. Usually a liquidation preference or a participating preference, voting preference or dilution preference. (terms defined below) Do not, under any circumstances, give a dilution preference.
  • 3. parre passu - latin for “we all get what the other gets.” ( I take some literary license here). IOW, if one class of stock is going to get diluted, everyone is getting diluted at the same rate. Insist on this in any deal you make.
  • 4. Liquidation preference - if the company sells, the stock with a liquidation preference gets all their money back before the remaining proceeds are split. Sometimes they get more than their money back. For instance, a 1X liquidation preference gets the amount they put in back first. A 2X gets twice the amount and so on. This is usually a big deal only if the company does not perform well.
  • 5. Participating Preferred - a clause on Preferred Stock that allows the holder to be paid back his money, or some multiple thereof, when the company is sold. For instance, a 3X participating preferred share would get three times what he put in before common shareholders get paid. Participation usually falls off in the event of an IPO. I would never give more than 1X Participation.
  • 6. Observation rights - The right for an investor to sit in on all board meetings and exec committee meetings without actually being on the board. Many VC’s are taking positions like this instead of board seats in order to mitigate liability. You can often counter a request for a board seat with observation rights. Say he wants two board seats out of five. Counter one with one observer. They’ll usually take that.
  • 7. Vesting - award of ownership or options over a period of time. Set it in months rather than years. Thus, a three year option would vest 1/36th per month.
  • 8. Reverse vesting - When the founders are stripped of their ownership rights of some amount of their founding stock (usually half) at the inception of the A round and they have to re-earn it over the vesting period. Do not make these options, make sure they remain as stock and that you control the voting rights even though they’re not vested. Don’t be offended or frightened off by this. It is a standard golden handcuff to ensure that the main guys they are investing in stay the course.
  • 9. pre-money valuation - the enterprise value of the company without the investment. Let’s say $8mm.
  • 10. post-money valuation - the enterprise value plus the amount of the investment. If you get $2mm in investment and your pre-money valuation is $8mm, then your post-money is $10mm.
  • 11. tranches (pronounced “traunches”) a staging of the investment dollars subject to hitting specific performance goals. Do not, for any reason, do this. If it’s a deal point, walk away. This is a great way to get screwed. They’ll make it sound so reasonable, but it’s just a recipe for disaster because nothing goes according to plan, so they can always renegotiate the terms of the deal when you run out of cash. (Many do).
  • 12. Option Pool - usually the investor will want to set aside 25% of the equity of the company in an option pool to be split by employees. I use a different bonus structure for my guys that is very well received and much less expensive for the owners. Basically, they get a dollar-for-dollar bonus on every dollar they were ever paid during their tenure six months after a change in control. They must be continuously employed and be employed on the payment date. I find that rank and file love this because it gives them a hard number to look to. If you pay them market rates (I always do) then this is a fair distribution in return for the work they had to do as a startup. It is MUCH cheaper for the owners/founders, is much less distracting from a management perspective and serves as a poison pill for someone who wants to buy you cheap. I save equity awards for C-Suite execs and Directors.
  • 13. Strike Price - the amount paid for a share of stock when an option is exercised. The value of the compensation is the market value - strike price. Always make the strike price the same as the last round of financing or more. There is no need to provide cheap options anymore. Indeed, accounting for cheap options is a nightmare. If you're bringing someone on after the first investment is made, price the option at whatever the investor paid for his shares.
  • 14. Rule 144 shares - You have to hold this stock for a year (if the company is public) before you can trade it. This is especially important in the case of options in that you will be taxed for the value of the compensation at the time you exercise the options, but you will not be able to trade for a year. This means that you come out of pocket to buy the stock and pay the taxes a year before you get the money from the sale of the shares, all the while taking the market risk on the appreciation of the shares. This is a hidden poison pill that makes options almost impossible for normal people to take advantage of. A good VC would never try this, but an unscrupulous investor or acquirer might.
  • 15. Rule 8A - the filing that makes options tradeable immediately so that you can exercise your option and sell it on the same day. Insist that there is a clause in any vested options you give that force an 8A filing at some trip point, usually six months after an IPO.
  • 16. Exercise date - the amount of time you have to buy your vested options before they are retrieved by the company should you leave before a liquidity event. Remember that, unless you’re public, these options will be treated as rule 144 stock until the stock is registered and publicly traded. This is a very important component of comp plans. Even if you vest, if you can’t afford to exercise and pay taxes, you lose the vested options if you leave.
  • 17. Due diligence - They will look up your ass and out your eyes. Don’t get offended when they ask the same question 15 times. They're not stupid (usually), they're just trying to see if you've thought through all sides.
  • 18. Cap Table - the list of who owns what in the company, how much they paid, when they paid, what they paid with (cash or services) their tax id #s, contact info including phone, email and hard address as well as any vesting schedule. Once this is published after a funding, it is almost impossible to change. Make sure it's right from day one and that it is kept completely up to date.
  • 19. Deferred compensation - if you have been taking a smaller than market (or no) salary (this should be true of any of the execs at seed stage) make sure you record the full market salary as an expense and setup a liability account called deferred comp for that amount that is not paid in cash. This account would be paid on closing of the round (or some negotiation about it). It’s a good way to get your market rate even though you haven’t been taking it the whole time.
  • 20. Board meetings - do not agree to any more than four formal meetings a year. Otherwise, you will be spending your days doing decks for the board rather than running the business. However, communicate with your board at least every month in writing with financials, waterfall reports, good bad and ugly developments. Remember to always communicate bad news early and loudly. No one expects you to be perfect and anyone on your board should be experienced enough to understand the rough times. Indeed, they are there to help you through them, not to whip you when they happen.
  • 21. Accredited investor: Someone who has earned $200k per year for the past two years if single, $300k per year for two years if married or has $1mm in net investible assets excluding their home. (There are other requirements for things like trusts, corporations, etc. Your lawyer can help you with these) You want to ensure that all of your investors are accredited for two reasons: first and foremost: you should never take a dollar from someone who can’t afford to lose it. Chances are you’re going to fail. When people can’t lose the money and don’t understand the risk, they get very upset, file lawsuits, make noise on social media and just generally try to ruin your reputation. Don’t ever take money from people who can’t afford it. Stress in your presentations that the money is completely at risk. I liken it to putting it all on Red 00 in roulette. You’re either going to win big or lose it all. The second reason is for regulatory purposes. Different states have different rules for registering if your investor pool is not entirely accredited. The rules are basically the same as being public. No startup can afford that type of regulatory cost.
  • 22. Term Sheet: This is the non-binding agreement that the VC will give you if he's ready to proceed to making a deal. It outlines the basic terms (wow, what a circular definition) of the deal. Get the term sheet right, but don't over-complicate it. It should be produced on one sheet of paper. Remember that it's non-binding, so you don't have to get crazy with legal language.
  • 23. No-look: This is a term of time when you agree not to shop your deal to any other VC's. For the most part, this is a bad idea, especially if you are not cash-flowing. Under no circumstance give this away without getting something in return (expedited diligence, breakup fee if they don't fund, more elastic terms, higher valuation, something).
  • 24. Seed Round: This is the tranche of money you raise, usually from yourself or friends and family, that is used to get a working product put together and get a little traction in the marketplace. You usually have to get to something like $50-100k per month in revenues on your seed round with a good growth trajectory in order to attract a good VC. Consider this the proof-of-concept stage. This is by far the hardest money to raise. Treat every dollar as if it were worth $100.
  • 25. Series A Round: This is the tranche where you get your first one or two good VC's. It's usually priced at about 20% - 25% of the overall company (meaning, you get $2.5mm and they get 25% or whatever the ratio ends up being). With this money, you should be able to prove out that there is a viable market for your product and that you have the ability to penetrate it. I personally believe that you should have a viable business when you run out of A money. That is, if you had to, you could turn off the growth engine and have a business that cash flows. It's growth that costs money. If you're not able to raise another round of financing, you'd better be able to stop growing and live on what you've killed. The big lesson here is treat every dollar as if it's worth ten. Do NOT get crazy with hiring at this point, especially administrative types.
  • 26. Series B Round: This is the tranche where you turn on full afterburner. You've proven the market exists and that your product is accepted. You've proven that you have the team that can exploit the market. Series B is where you lay on the staff to make it a big business. You should have an operating business when this money runs out, including financing the growth engine. Typically, VC's will get 15% of the company for a B round and the amount can be as high as $200mm. Whatever it is, it will be a big number, usually 8-10X of your A round.
  • 27. Series C and beyond: These rounds are saved so that you have a big business that is ready to go public or be bought for big dollars. Your executive team is well established. You may want to use some of this money to go into new products or buy another company. Whatever it is, be careful taking this money. If you're a hot company, everyone will want to give it to you, but it's easy to get over-diluted. It's also easy to let the success go to your head. Don't be afraid to cash out a bit if you take a C round. Meaning, sell a bit of your stock to the investor so that you're diversifying and put some cash in your pocket. They might give you a bit of grief for it at first, but it's not an unusual use of proceeds for a later round.