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Startup Equity 101 vs 5 01 13
1. Startup Equity 101 Primer
for Founders and Employees
May 1, 2013
by Jamie Lee
@jieunjamie
with Ekaterina Mouratova, PLLC
www.mouratovalawfirm.com
Thursday, May 2, 13
2. Disclaimer
Hi! I’m not an accountant or a lawyer.
The information contained herein and ensuing discussion
should NOT be considered tax or legal advice.
The information is intended to help you get familiarized with
general concepts in startup finance, which may or may not
apply to your situation.
Thank you!
Jamie Lee
@jieunjamie
jieunjamie.com
Thursday, May 2, 13
3. Startup Equity: More ART than SCIENCE
but still need to ASK questions
Thursday, May 2, 13
4. Before joining a startup, ask
•Is this the right team and company for my success?
•What is my percentage of ownership?
•What is total company capitalization?
•How long is my vesting schedule?
•What are tax implications?
•What is the estimated valuation at exit?
•What do I need to do when I leave?
Startup Equity: More ART than SCIENCE
but still need to ASK questions
Thursday, May 2, 13
5. Before joining a startup, ask
•Is this the right team and company for my success?
•What is my percentage of ownership?
•What is total company capitalization?
•How long is my vesting schedule?
•What are tax implications?
•What is the estimated valuation at exit?
•What do I need to do when I leave?
Startup Equity: More ART than SCIENCE
but still need to ASK questions
If you’re a founder or employee,
•Research market rate salary and equity comp
•Read the partnership and employment agreements
•Negotiate like a business person
•Consult a lawyer or tax accountant (devil’s in the details)
•Exercise your options early
•Make 83b election ASAP for restricted stock grants
Thursday, May 2, 13
6. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Thursday, May 2, 13
7. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Thursday, May 2, 13
8. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Thursday, May 2, 13
9. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Thursday, May 2, 13
10. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Thursday, May 2, 13
11. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Your startup is like your baby.
But let’s face it, most of us won’t work
at the next Facebook or Google.
Thursday, May 2, 13
12. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Your startup is like your baby.
But let’s face it, most of us won’t work
at the next Facebook or Google.
Thursday, May 2, 13
13. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Your startup is like your baby.
But let’s face it, most of us won’t work
at the next Facebook or Google.
Thursday, May 2, 13
14. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Your startup is like your baby.
But let’s face it, most of us won’t work
at the next Facebook or Google.
Brave souls featured in
Read Write’s “8 Real-
World Stories Of Why
Startups Fail”
Failure is like a badge of
honor, and a great
teacher. Financially
speaking, it means no
return.
Thursday, May 2, 13
15. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Your startup is like your baby.
But let’s face it, most of us won’t work
at the next Facebook or Google.
Brave souls featured in
Read Write’s “8 Real-
World Stories Of Why
Startups Fail”
Failure is like a badge of
honor, and a great
teacher. Financially
speaking, it means no
return.
Thursday, May 2, 13
16. High
(1)
High Return
Low Risk
(2)
High Return
High Risk
Low
(3)
Low Return
Low Risk
(4)
Low Return
High Risk
Low High
risk
return
Startup Equity: Think like an investor
Consider the risk profile of your investment.
Your startup is like your baby.
But let’s face it, most of us won’t work
at the next Facebook or Google.
Brave souls featured in
Read Write’s “8 Real-
World Stories Of Why
Startups Fail”
Failure is like a badge of
honor, and a great
teacher. Financially
speaking, it means no
return.
Yup, that’s
me.
Thursday, May 2, 13
19. Startup Equity: Owning a piece of the pie
Let’s say your startup is like
a pizza pie you and your
team make from scratch.
Individual slices are owned
by different people, but the
team’s goal is to grow the
pie as a whole.
As more people get
involved and invest, your
slice may get skinnier, and
the pie bigger.This is called
dilution.
Thursday, May 2, 13
20. Startup Equity: Owning a piece of the pie
Let’s say your startup is like
a pizza pie you and your
team make from scratch.
Individual slices are owned
by different people, but the
team’s goal is to grow the
pie as a whole.
As more people get
involved and invest, your
slice may get skinnier, and
the pie bigger.This is called
dilution.
“Employee ownership is
such an important part of
startup culture. It reinforces
that everyone is on the
team, everyone is sharing in
the gains, and everyone is a
shareholder.”
- Fred Wilson,AVC.com
Thursday, May 2, 13
21. Startup Equity: Owning a piece of the pie
Let’s say your startup is like
a pizza pie you and your
team make from scratch.
Individual slices are owned
by different people, but the
team’s goal is to grow the
pie as a whole.
As more people get
involved and invest, your
slice may get skinnier, and
the pie bigger.This is called
dilution.
Founders**
55% Investors*
25%
Employee Pool
20%
*Hypothetical situation where investors
have bought a quarter of the pie.
**If you own 51% and more of a
company, you own controlling interest.
“Employee ownership is
such an important part of
startup culture. It reinforces
that everyone is on the
team, everyone is sharing in
the gains, and everyone is a
shareholder.”
- Fred Wilson,AVC.com
Thursday, May 2, 13
22. Dilution is part of life
Each new issuance of stocks results in dilution of existing shareholders
Dilution is inevitable part of company growth.
Pre-dilution
1% ownership
100,000 shares
Total shares outstanding:
10M shares, $1/share
$100,000
Slice of a small pie
Series A funding
2M shares issued
at $3/share
Total $ raised:
$6M .8333% ownership
100,000 shares
Total shares outstanding:
12M shares, $3/share
$300,000
Skinnier slice of a bigger pie
Post-dilution
Thursday, May 2, 13
23. Employee Stock Ownership
Typically, total non-founder employee equity
pool tends to fall between 10% - 20%.
Title
Of
Total Shares
CEO 5.00 - 10.00%
C-level Executives 1.00 - 3.00%
VP, Directors 0.50 - 2.00%
Managers 0.25 - 1.00%
Board Directors 0.50%
Total capitalization = Total number of shares
issued by a company, including stocks and options
Capitalization table = Spreadsheet that keeps
track of who owns what kind of ownership.
Considered private and sensitive information
Thursday, May 2, 13
24. Set you expectations right
$ Cash Comp
Equity Comp
At a smaller, younger, startup with less funding
$ Cash Comp
Equity Comp
At a bigger, more established company after several rounds of fundraising
Thursday, May 2, 13
25. Startup Equity: Understand the Pecking Order
Shareholders
Board of Directors
CEO
•Board of Directors is legally bound to serve
in the best interest of shareholders.This
responsibility is called Fiduciary Duty.
•Board of Directors sets general company policy
and appoints, compensates, reviews and fires the
CEO.
•The lead investor in a round of funding usually
gets a Board seat.
•CEO manages the company “at the pleasure
of the Board.”
Thursday, May 2, 13
26. Startup Equity: Common vs. Preferred
Who
gets them?
What
kind of rights?
When
are they issued?
Why
are they issued?
How
about IPO?
Founders, employees, some board
members
Outside investors such asVCs
At incorporation and at the discretion
of the Board of Directors
When investors buy company shares.
They usually pay a premium over
Common for Preferred. Named Series
A, B, C, D, etc.
To retain and motivate employees,
in lieu of cash bonus, aka “Sweat Equity”
To raise capital for company growth, etc.
aka “Cash Equity”
To attend shareholder meetings
Can include board seat, Preference,
or the right to get paid before
common, right of first refusal, anti-
dilution rights, right to convert to
Common
Equal footing as Preferred Shares Preferred rights go away
Thursday, May 2, 13
27. 1. Founders and founding members receive
common shares. Special vesting schedule applies.
2. Restricted stocks are issued to employees at
early stage companies while the value of stock is
relatively low.
3. Stock options are the most common form of
employee equity.
You may have heard of the ESOP – Employee Stock
Option Plan and ISOP –Incentive Stock Option
Plan
Types of Common Equity
Apple Computer, Inc.
Incorporated on Jan 3,1977
Stock value: $0
Thursday, May 2, 13
28. Restricted Stock
What you
get
Stock granted as a form of compensation with restrictions.
Nitty Gritty
Often the restriction is continued employment during period of time, upon
which the shares vest. Or the restriction can be performance based.
Legal & Tax
Fine Print
Under the 83(b) IRS code, you can recognize “income” upon granting of stock.
Income is difference between FMV and stock price, which are typically the
same. Meaning no income is recognized. Must be sent to IRS within 30 days
from day of purchase or grant of shares.
Thursday, May 2, 13
29. Vesting Schedule
4 year vesting with 1 year cliff is common.
1 year cliff means you don’t vest during
the 1st year. If you leave during this period,
you leave with no equity.
Unvested equity may be repurchased by the
company and returned to the employee
pool.
Idea is to avoid a “hit and run” situation and
to retain talented employees.
Oops
27.1%
+1 mo.
Day 1 1st year 2nd year 3rd year 4th year
0% 25% 50% 75% 100%
0 2,500
2,710
5,000 7,500 10,000
Vested
Shares
Generally, option strike price will not change throughout vesting schedule.
Thursday, May 2, 13
34. $0
$25
$50
$75
$100
2013 2014 2015 2016
Company XYZ Share Price
FMV Cost to EE
100 shrs granted to EE at FMV of
$1.00 with 4 year vest. EE files
83B Election recognizing income
of $1 (FMV) - $1 (shr price) = $0
(83B is beautiful)
Thursday, May 2, 13
35. $0
$25
$50
$75
$100
2013 2014 2015 2016
Company XYZ Share Price
FMV Cost to EE
100 shrs granted to EE at FMV of
$1.00 with 4 year vest. EE files
83B Election recognizing income
of $1 (FMV) - $1 (shr price) = $0
At end of 1 year anniversary,
25 shares vested to EE.
FMV rose to $5/shr.
($5 - $1) x 25 shares = $100
Don’t owe taxes until you sell.
(83B is beautiful)
Thursday, May 2, 13
36. $0
$25
$50
$75
$100
2013 2014 2015 2016
Company XYZ Share Price
FMV Cost to EE
100 shrs granted to EE at FMV of
$1.00 with 4 year vest. EE files
83B Election recognizing income
of $1 (FMV) - $1 (shr price) = $0
At end of 1 year anniversary,
25 shares vested to EE.
FMV rose to $5/shr.
($5 - $1) x 25 shares = $100
Don’t owe taxes until you sell.
After 2 years, 50 shares vested to EE.
FMV rose to $25/shr.
($25 - $1) x 50 shares = $1,200 value.
Don’t owe taxes until you sell.
(83B is beautiful)
Thursday, May 2, 13
37. Stock Options
What you
get
Right to buy stock at strike price.You exercise your option when you buy stock.
Nitty
Gritty
Board of directors sets the strike price based on fair market value (FMV) of common
stock decided by a 409aValuation.“At the money” means that FMV is equal to strike
price (and not liable for taxes).
Legal &
Tax Fine
Print
Once you exercise your option, you are liable for tax on the gain, or difference
between FMV and strike price, as ordinary income*. Capital gains from stock held
longer than one year is taxable as long term capital gains. Most companies require
option holders to exercise within 90 days of termination.You may be able to
negotiate a “cashless exercise” or cash bonus to cover the exercise price.
*unless the option is Incentive Stock Option
Thursday, May 2, 13
38. Incentive Stock Option
Incentive stock options (ISOs), are a type of employee stock option that can
be granted only to employees and confer a U.S. tax benefit.
The tax benefit is that on exercise the individual does not have to pay
ordinary income tax (nor employment taxes) on the difference between the
exercise price and the fair market value of the shares issued (however, the
holder may have to pay U.S. alternative minimum tax instead).
Instead, if the shares are held for 1 year from the date of exercise and 2 years
from the date of grant, then the profit (if any) made on sale of the shares is
taxed as long-term capital gain. Long-term capital gain is taxed in the U.S. at
lower rates than ordinary income.*
*straight out of Wikipedia
Thursday, May 2, 13
41. $0
$15
$30
$45
$60
$75
$90
2013 2014 2015 2016 2017 2018
Company ABC Share Price and Options
FMV ESOP ISO
100 options granted to EE at FMV of
$10.00 with 4 year vest. Strike price is
equal to FMV at time of grant, $10.This is
called “At the Money”
Thursday, May 2, 13
42. $0
$15
$30
$45
$60
$75
$90
2013 2014 2015 2016 2017 2018
Company ABC Share Price and Options
FMV ESOP ISO
100 options granted to EE at FMV of
$10.00 with 4 year vest. Strike price is
equal to FMV at time of grant, $10.This is
called “At the Money”
25 options vested to EE. She can buy 25
shares at $10 and realizes gain: (FMV $25 -
Strike price $10) X 25 shares = $375
This gain will be taxed. If she sells those
shares, she will be taxed again for the gain.
Thursday, May 2, 13
43. $0
$15
$30
$45
$60
$75
$90
2013 2014 2015 2016 2017 2018
Company ABC Share Price and Options
FMV ESOP ISO
100 options granted to EE at FMV of
$10.00 with 4 year vest. Strike price is
equal to FMV at time of grant, $10.This is
called “At the Money”
25 options vested to EE. She can buy 25
shares at $10 and realizes gain: (FMV $25 -
Strike price $10) X 25 shares = $375
This gain will be taxed. If she sells those
shares, she will be taxed again for the gain.
2 years in, management decide to incentivize
the EE with Incentive Stock Options. Similar 4
year vest.At this time, FMV is $53, so strike
price of ISO set to $53.
Thursday, May 2, 13
44. $0
$15
$30
$45
$60
$75
$90
2013 2014 2015 2016 2017 2018
Company ABC Share Price and Options
FMV ESOP ISO
100 options granted to EE at FMV of
$10.00 with 4 year vest. Strike price is
equal to FMV at time of grant, $10.This is
called “At the Money”
25 options vested to EE. She can buy 25
shares at $10 and realizes gain: (FMV $25 -
Strike price $10) X 25 shares = $375
This gain will be taxed. If she sells those
shares, she will be taxed again for the gain.
2 years in, management decide to incentivize
the EE with Incentive Stock Options. Similar 4
year vest.At this time, FMV is $53, so strike
price of ISO set to $53.
When FMV falls under strike
price, it’s called “under water”
Thursday, May 2, 13
45. Startup Equity RECAP: More ART than
SCIENCE but still need to ASK and do the
MATH
Thursday, May 2, 13
46. Startup Equity RECAP: More ART than
SCIENCE but still need to ASK and do the
MATH
Before joining a startup, ask
•Is this the right team and company for my success?
•What is my percentage of ownership?
➡ # shares you own / total shares issued
•How long is my vesting schedule?
➡ 4 years with 1 year cliff is standard
•What are tax implications?
➡Restricted stock: make 83B elections
➡Option holders: liable for capital gains at
exercise and when sold
•What is total company capitalization?
•What is the estimated valuation at exit?
•What do I need to do when I leave?
If you’re a founder or prospective
employee,
•Research market rate salary and equity comp
➡See appendices for references
•Read the partnership and employment agreements
•Negotiate like a business person
•Consult a lawyer or tax accountant
Thursday, May 2, 13
47. Startup Equity: More ART than SCIENCE
but still need to do the MATH
1) Ownership = # Shares Granted toYou
Total Capitalization
Formulas Example
1) 1% = 0.1M Shares Granted
10M Total Shares Outstanding
2) Dilution Factor =
(#Your Future Shares + Future Investor Shares)
Total Cap. + #Your Future + Future Investor Shares
2) 0.17% = (0.05M +2M)
(10M+0.1M+2M)
1% - 0.17% = 0.83% New Ownership
3)Your Payday at Exit* =
(Your Ownership X Company Exit Price)
– (Total Exercise Price)
3) $99K* =
(0.83% X $30M) - ($150K)
*Assuming $1 strike price,
BEFORE taxes, very rough est.
Thursday, May 2, 13
48. Sources
- Andy Payne, Startup Equity for Employees: http://www.payne.org/index.php/Startup_Equity_For_Employees
- Brad Feld, Blog archive on Term Sheets:
http://www.feld.com/wp/archives/2005/08/term-sheet-series-wrap-up.html
- Chris Dixon, The One Number You Should Know About Your Equity http://cdixon.org/2009/08/27/the-one-number-
you-should-know-about-your-equity-grant/
- Fred Wilson, MBA Monday Series on Equity: http://www.avc.com/a_vc/2010/09/employee-equity.html
http://www.avc.com/a_vc/2008/11/restricted-stoc.html
- How Stuff Works, Stock Options:
http://money.howstuffworks.com/personal-finance/financial-planning/stock-options1.htm
- Infochachkie, What The Heck Are My Startup Stock Options Worth?! Seven Questions You Should Ask Before Joining
A Startup: http://infochachkie.com/options/
- Paul Graham, Equity Equation: http://paulgraham.com/equity.html
- Pop History of DIg, Apple Rising: 1976 - 1985: http://www.pophistorydig.com/?tag=apple-computer-ipo
- Startup Company Lawyer, What is an 83b Election?
http://www.startupcompanylawyer.com/2008/02/15/what-is-an-83b-election/
- Wealthfront, Manage Your Tech Career: https://blog.wealthfront.com/startup-employee-equity-compensation/
- Wealthfront, The 12 Crucial Questions About Stock Options: https://blog.wealthfront.com/stock-options-package-
valuation/
- Wikipedia, Restricted Stock: http://en.wikipedia.org/wiki/Restricted_stock
Thank you!
Thursday, May 2, 13
50. Appendix A: LLC v. C Corp
Type of
Entity
Limited Liability Company (LLC) C Corporation S Corporation
Ownership
Unlimited members. Members
own “units.”
500 shareholders if private. No
limit on shareholders if public.
Up to 35 shareholders, one class
of stock allowed.
Liability
Members not liable for company
debts.
Shareholders not liable for
company debts.
Shareholders not liable
Taxes
No entity tax; profits and losses
are passed on to members.
“Double taxation” Company is
taxed as an entity. Shareholders
are also taxed.
“Double taxation” Company is
taxed as an entity. Shareholders
are also taxed.
Management
Designated in Operating
Agreement. May be managed by
Member or Manager.
Managed overall by Board of
Directors. Officers manage day to
day.
Managed overall by Board of
Directors. Officers manage day to
day.
Thursday, May 2, 13
51. Appendix A: LLC v. C Corp
Type of
Entity
Limited Liability Company (LLC) C Corporation S Corporation
Ownership
Unlimited members. Members
own “units.”
500 shareholders if private. No
limit on shareholders if public.
Up to 35 shareholders, one class
of stock allowed.
Liability
Members not liable for company
debts.
Shareholders not liable for
company debts.
Shareholders not liable
Taxes
No entity tax; profits and losses
are passed on to members.
“Double taxation” Company is
taxed as an entity. Shareholders
are also taxed.
“Double taxation” Company is
taxed as an entity. Shareholders
are also taxed.
Management
Designated in Operating
Agreement. May be managed by
Member or Manager.
Managed overall by Board of
Directors. Officers manage day to
day.
Managed overall by Board of
Directors. Officers manage day to
day.
Thursday, May 2, 13
52. Appendix A: LLC v. C Corp
Type of
Entity
Limited Liability Company (LLC) C Corporation S Corporation
Ownership
Unlimited members. Members
own “units.”
500 shareholders if private. No
limit on shareholders if public.
Up to 35 shareholders, one class
of stock allowed.
Liability
Members not liable for company
debts.
Shareholders not liable for
company debts.
Shareholders not liable
Taxes
No entity tax; profits and losses
are passed on to members.
“Double taxation” Company is
taxed as an entity. Shareholders
are also taxed.
“Double taxation” Company is
taxed as an entity. Shareholders
are also taxed.
Management
Designated in Operating
Agreement. May be managed by
Member or Manager.
Managed overall by Board of
Directors. Officers manage day to
day.
Managed overall by Board of
Directors. Officers manage day to
day.
Thursday, May 2, 13
53. Appendix A: LLC v. C Corp
Type of
Entity
Limited Liability Company (LLC) C Corporation S Corporation
Ownership
Unlimited members. Members
own “units.”
500 shareholders if private. No
limit on shareholders if public.
Up to 35 shareholders, one class
of stock allowed.
Liability
Members not liable for company
debts.
Shareholders not liable for
company debts.
Shareholders not liable
Taxes
No entity tax; profits and losses
are passed on to members.
“Double taxation” Company is
taxed as an entity. Shareholders
are also taxed.
“Double taxation” Company is
taxed as an entity. Shareholders
are also taxed.
Management
Designated in Operating
Agreement. May be managed by
Member or Manager.
Managed overall by Board of
Directors. Officers manage day to
day.
Managed overall by Board of
Directors. Officers manage day to
day.
Thursday, May 2, 13
54. ACME, LLC
Annual net profit: $100M
No corp tax
Appendix B: LLC Tax Passthrough
•Members taxed for ACME’s profit (or loss) proportionately
•Members receive K1 tax form (and tax assistance from entity,
depending on terms of agreement)
A:10%
$10M
B:10%
$10M
C:80%
$80M
Tax Liability Tax Liability
Thursday, May 2, 13
55. ACME, Inc.
Annual profit: $100M
Corp tax: $35M
Net profit: $65M
dividends paid out to shareholders
(taxed on individual level)
Appendix C: C Corp “Double Taxation”
•Both ACME, Inc. and shareholders taxed
•No tax assistance from entity to shareholders
dividends dividends
Thursday, May 2, 13
56. Appendix D: Recommended Online Resources
• Check out Anonymous Startup Salaries, Stock Options and Equity on Ackwire.com
• Check out Fred Wilson’s Cap Table Template on Google Docs
Thursday, May 2, 13
57. Appendix E: Recommended Online Resources
• Check out Patrick McKenzie’s Salary Negotiation: Make More Money, Be More
• Check out David Weekly’s An Intro to Stock Options
Thursday, May 2, 13