Overview & analysis of the market from Pre-Seed, to Seed, Later Stage Seed / Seed Extension, Series, A, B, C, D to the private IPO phenomenon - understanding trends - which are crowded, overpriced, underpriced and key risk points Why investing now is more attractive than ever before What industries, sectors, company stage and geographies are best for you  Convertible notes - key points and the meaning beyond the moving parts Priced equity rounds - key points and the meaning beyond the moving parts Valuation concepts on pricing valuations when investing, exiting and risk tied to perceived exit multiples Portfolio construction strategies for angels and VCs - how to allocate your capital  Best practices for sourcing deal flow and conducting due diligence  Tactics to get into oversubscribed deals Strategies for continuing to invest in portfolio companies a 2nd, 3rd, 4th, 5th time, etc Best practices for post investment information rights, governance, adding value and Different options to invest ranging from Angel List, to other investor platforms, angel groups, demo days, accelerators, VC funds, SPVs, tax breaks for UK, EU and Israeli taxy payers Different options to get liquidity on the secondary market before definitive liquidity event for startup / how to sell some stock before the final exit

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GENERAL
SOLICITATION
LEGAL DISCLAIMER
2
Under no circumstances should any material in this presentation be used or considered
as an offer to sell or a solicitation of any offer to buy an interest in any individual
company or investment fund managed by Georgetown Angels (Rubicon Venture Capital
LLC and Georgetown Angels Fund I DBA Rubicon Venture Capital). Any such offer or
solicitation will be separately made only by means of the Confidential Private Offering
Memorandum relating to the particular fund to persons who, among other
requirements, meet certain qualifications under federal securities laws and generally are
sophisticated in financial matters, such that they are capable of evaluating the merits
and risks of prospective investments. Copyright © 2014 All rights Reserved Georgetown
Angels & Rubicon Venture Capital.
This Confidential Investor Presentation has been prepared for discussion purposes only.
It is being delivered on a confidential basis to specified parties solely to assist them in
deciding whether to proceed with their investigation of Rubicon Venture Capital (the
“Company”). This Investor Presentation does not purport to contain all of the
information that may be required or relevant to a recipient’s evaluation of the Company.
The distribution and use by each recipient of the information contained herein and any
other information provided may not be distributed, reproduced or used without the
express consent of the Company or for any purpose other than the evaluation of the
Company.
Neither the Company or any of its affiliates or representatives makes any
representation, warranty or guaranty of any kind, express or implied, as to the accuracy,
completeness or reasonableness of the information contained herein or any other
written or oral communication transmitted or made available to the recipient. The
Company and its affiliates and representatives expressly disclaim any and all liability
based on or arising from, in whole or in part, such information, errors therein or
omissions therefrom.
This Investor Presentation includes forward-looking statements and projections
provided by the Company. Such projections and forward-looking statements reflect
various assumptions of management concerning the future performance of the
Company, and are subject to significant business, economic and competitive
uncertainties and contingencies, which are beyond the control of the Company. Actual
results may materially vary from anticipated results. No representations or warranties
are made as to the accuracy or reasonableness of such assumptions or the projections or
forward-looking statements based thereon. Only those representations and warranties
that are made in a definitive written agreement relating to a transaction, when and if
executed, and subject to any limitations and restrictions as may be specified in such
definitive agreement, shall have any legal effect. Each recipient should make an
independent assessment of the merits of pursuing a transaction and should consult its
own professional advisors.
The delivery of this Investor Presentation should not imply that there has been no
change in the business and affairs of the Company since the date of the Investor
Presentation. Neither the Company nor its affiliates or representatives undertakes any
obligation to update any of the information contained herein. The Company is free to
conduct the process for the transaction as it determines in its sole discretion (including
without limitation, ceasing to proceed with any transaction, terminating further
participation in the process by any party, and entering into an agreement with respect to
a transaction without prior notice to you or any other person) and any procedures
relating to such transaction may be changed at any time without prior notice to you or
any other person.

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andrew@rubicon.vc
Twitter: @RomansVentures
www.linkedin.com/in/romans
• Very active venture capitalist in Silicon Valley & New York – Rubicon Venture
Capital – roughly 1 new investment per month – unique value add platform for startups
VC-backed Entrepreneur - The Global TeleExchange (The GTX), a $50M venture-backed
telecom VoIP venture…Raised $27m from Lucent Technologies + $20m VC
• VC investment banker / advisor - Georgetown Venture Partners & Georgetown
Angels
• Founder of The Founders Club (42 VCs on the advisory board)
• Author and frequent venture capital speaker on CNBC & msnbc
• Fluent in English, German & French, conversant Slovak – lived 15 years in Europe
• BA University of Vermont, Duke University, FU Berlin, MBA in Finance from
Georgetown University on scholarship
ANDREW ROMANS, RUBICON VENTURE CAPITAL

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TRANSLATED INTO CHINESE & RUSSIAN

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• Overview & analysis of the market from Pre-Seed, to Seed, Later Stage Seed / Seed
Extension, Series, A, B, C, D to the private IPO phenomenon - understanding trends -
which are crowded, overpriced, underpriced and key risk points
• Why investing now is more attractive than ever before
• What industries, sectors, company stage and geographies are best for you
• Convertible notes - key points and the meaning beyond the moving parts
PROGRAM FOR THE DAY 1/3

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• Priced equity rounds - key points and the meaning beyond the moving parts
• Valuation concepts on pricing valuations when investing, exiting and risk tied to
perceived exit multiples
• Portfolio construction strategies for angels and VCs - how to allocate your capital
• Best practices for sourcing deal flow and conducting due diligence
• Tactics to get into oversubscribed deals
PROGRAM FOR THE DAY 2 / 3

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• Strategies for continuing to invest in portfolio companies a 2nd, 3rd, 4th, 5th time, etc
• Best practices for post investment information rights, governance, adding value and
Different options to invest ranging from Angel List, to other investor platforms, angel
groups, demo days, accelerators, VC funds, SPVs, tax breaks for UK, EU and Israeli taxy
payers
• Different options to get liquidity on the secondary market before definitive liquidity
event for startup / how to sell some stock before the final exit
PROGRAM FOR THE DAY 3/ 3

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Secondaries
THE PROCESS OF STARTUP FINANCINGS
Founders,
Friends, Family,
Credit Cards &
Customer Revs
Pre-Seed
Seed
(Demo Day
Context)
Seed
Extension /
Later Stage
Seed
Series A Series B
Series C Series D
Pre-IPO /
Mezzanine

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DIFFERENT STA GES OF INVESTING
Pre-Seed
Demo
Day Seed
Later
Stage
Seed
Series A Series B
Pre-IPO
Growth &
Secondaries
Smart, but a lot of
work / needs a
machine
Crowded easy to access
over priced
Less easy to access
slightly over priced
Difficult to access
optimal risk / reward
Difficult to access
optimal risk / reward
Crowded difficult to access
over priced w/protection

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TECH VC MORE ATTRACTIVE NOW THAN EVER BEFORE
• 5.6x more Internet users now than in 2000. Women who make more than
50% of consumer purchase decisions are online (fixed and mobile).
• Broadband connections are 120x faster. 1995 56k modems > today 6.7 Mbps
average US Internet connection.
• People are mobile connected everywhere all the time. Personal, location
aware, at point of purchase. 138m US smartphone users, up 18.8% since 2012.
99m US tablet users, up 42.3% since 2012.
• Everyone socially connected driving viral growth rates. Facebook 1bn
active monthly users. Twitter 288m. LinkedIn 200m. YouTube 4bn+ hours of
video watched by 1bn+ monthly users.

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TECH VC MORE ATTRACTIVE NOW THAN EVER BEFORE
• Everyone has credit cards with single click to purchase. Apple ecosystem
$25bn up from zero in 2008
• Amount of LP money addressing series A & B down. Most so-called VC dollars
are investing in growth not VC. Amount of actual committed VC capital is far
less now than in 1998 and today’s system should require more to be right-
sized
• Amount of money investing in Seed increasing. Number of startups being
created is increasing brings more funded deal flow to A & B rounds where Rubicon is
focused
• VC is the best place to position for a shift in the economy or correction of
possible bubble. Pre-Seed, Seed, Growth and PE will be hit hard compared to early stage
VC

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1999 VS 2 014 – WE ARE NOT IN A BUBBLE
1999 2014
US tech funding $ $71bn $48bn
Funding as % US Tech GDP 10.8% 2.6%
S&P IT index forward P/E 39.0x 16.1x
Global Internet Population 0.4bn people 3bn people
US e-commerce revenues $12bn $304bn
Number of IPOs 371 53
Median time to IPO 4 years 11 years
Source: Andreessen Horowitz
70% of VC dollars are actual private IPO expansion capital / Not enough VC cash in system

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SECTORS, STAGE & GEOGRAPHIES BEST FOR YOU?
Internet & Software
Consumer
Enterprise
Hardware
Cleantech
Medtech
Biotech
GEOGRAPHY
SECTOR FOCUS
STAGESeed
Later
Stage

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THE DIFFERENT PROCESSES OF A VC’S JOB
Plan Fund /
unique
positioning
Recruit
team
Source
deals
Vet deals
and Due
Diligence
Seduce the
CEO &
other VCs
Complete
investment
Collect info to
make future
investment
decisions
Add value to
investment &
improve your
reputation
Impact the
exit
Collect info
& report to
LPs / Events
Build VC
brand and
recruit more
team
Raise next
fund
Where do you fit or what makes you interesting enough to start a fund?

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• Why convertible note vs a priced round?
• Cap or discount rate to the next priced round – lower of the
two
• Discount rate - 10% to 30% - 20% is the norm – uncapped
notes?
• Interest rate – 4% to 8% - 5% or 6% is the norm
• Conversion feature – what happens if NewCo is sold prior to
a priced round. 1x, 2x, 3x or cap
• Maturity date or SAFE note – 12, 18 or 24 months
• What’s behind the moving parts?
• Pricing for success
CONVERTIBLE NOTES

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• Pre-money valuation = $10m (classic example)
• Size of financing round = $5m (classic example)
• Post money Valuation + 15m (pre + round)
• % to new investors = round / post (small number / big number = 33% in this example.
Modern times investors get less – in-your-head-math pre is 2x size of round on 33% deal)
• % dilution to insiders (1-% to new investors)
• Target 10x upside for early / 4x upside for later stage
• Liquidation prefs, pro rata rights, information rights, governance
• Get a 1x liquidation pref or walk otherwise founders & existing investors are not confident
• No pro rata and we walk away at Rubicon
• If we don’t have good close working chemistry with CEO we walk away
PRICED ROUNDS

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LIQUIDATION PREFS STRUCTURING
• Seed stage investors should get a 2x liquidation preference and
win in acqui-hire exits (McClure is one of few that pulls this off –
very smart, but hard to get)
• All other investors should get 1x liquidation prefs
• Newest investors investing at high valuations may get 1x senior
liquidation pref, or 1.2x or higher to justify high valuations
• Use liquidation prefs in concert with valuations and secondaries
• Buying founder shares without liquidation prefs is dangerous
and should be priced accordingly – structured deals such as
investor makes 1.5x and then splits with seller
• Only use law firms active in the local market place and use
standard terms

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• Most VCs have some kind of focus on stage, sector and geography and often strategy is driven by
investors in the fund
• Timeless elements in the investor decision making equation…
• Team is number 1 – MANAGEMENT, MANGEMENT, MANGEMENT!!!!!!!!!!!!!!!!!!!
• Market is number 2 and don’t invest unless you have 1 and 2 – IT’S GOT TO BE BIG to cover fees
and risky losses
• Team must be a fit to take on the market – subject matter experts born to disrupt that market
• Product - VC is typically product centric. Technology must be a miracle to drive growth and keep
out competitors. Never be seduced by a product with bad management and no clear market
• Traction – in a horse race if your horse is in the lead and you drop rocket fuel funding…
• Investor value add – @Rubicon if we can’t add value we don’t invest
• Take on a lazy incumbent – if one big fat lazy company has 80%+ of the market a new startup
can disrupt and take a slice and make a 100x for investors
WHY INVEST? WHAT’S MOST IMPORTANT?

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• 10x potential for early investments
• 4x potential for later stage investments
• 2x potential with 1x downside near zero risk protection via prefs for large amounts
• Get 1x senior liquidation pref for each investment / prefs and pre-money are
interchangeable
• Performance warrants – get paid if you are super value add
• Make sure each valuation is low enough that each next financing will be an up-round.
Down rounds kill founders, early and small investors
• Know the market and do some math. Sanity check your numbers and back your way into
a valuation to make sure the return is commensurate with the risk
• Can you afford to wait 3 or 7 years before the first exit? Who are you?
VALUATIONS & STAGE

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• What’s your total amount of capital to be invested over how
long a period of time?
• Startup and stage diversification
• Vintage diversification – investing at the top of a bubble curve
vs bottom of downturn
• How many investments will / can you make over a 3 year
period?
• What’s your average first check size, follow on check, reserve
amount?
• What stage can you muscle into?
PORTFOLIO CONSTRUCTION 1/2

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• Can you access more money next year, next, next, next year?
• VCs with 8 investments in the fund are crazy
• VCs investing in 15 over 5 years are crazy
• Pre-seed requires 100+ diversification
• Seed requires 30+
• Series A should have 20+
• Optionality concept: invest in 25 and throttle 50% of fund
capital into top 5 to 10 performers
• Later stage should target 10 to 25
PORTFOLIO CONSTRUCTION 2 /2

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IMPORTANCE OF DEAL FLOW & ABILITY TO CLOSE
• Deal flow is the life blood of a fund
• A fund with 3,000 high quality deals per year is better than a
fund with 1,000 high quality deals per year
• A fund with lots of bad deal flow is worthless
• Deal flow is not enough, investors must convince the
CEO, founders & other VCs that you add value not just
capital or stupid enough to over pay
• Must have ability to demonstrate what value you bring
beyond just cash

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• How can you see 100% of all the deals
• Big funnel, invest in small sub-set
• Blogs, Twitter, books, TV
• Produce and attend events
• Lots of public speaking
• How can you get other VCs to bring you deals?
SOURCING DEAL FLOW AND CONDUCTING DD

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• Strategy /brand to be unique
• Strategy /brand to source new deals
• Strategy /brand to close into the oversubscribed deal
• Strategy /brand to make all founders and VCs love you and
want to work with you
• Strategy /brand to raise more capital
WHAT’S YOUR BRAND?

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• Adding value
• Information rights
• Governance
• Continuing to invest in portfolio companies
• Accessing enough information to make future investment
decisions
POST INVESTMENT GAME

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• Angel List & other investor platforms
• Angel groups – hunt in packs
• Accelerators, demo days & pre-demo day investing
• Tax breaks for UK, EU and Israeli tax payers
• Special Purpose Vehicles (SPVs)
• Invest into VC fund, Fund of Funds or start a corporate VC
• Start your own fund & all of the above
DIFFERENT OPTIONS TO INVEST

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• How to get your money out after investing
• M&A trade sales
• IPO
• Secondary market for direct investment
• Secondary market for LP interest
• Investment pace and positioning for vintages
THE LADDER TO LIQUIDITY

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• 2% annual management fee
• 20% carry
• Dynamics around 2 & 20
• Stacking fees and diversification among vintages
• Positive dynamics of multiple funds at once
VENTURE CAPITAL REVENUE MODEL

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• Financial return
• Access to innovation
• Access to information in Silicon Valley, New York, London and
Israel
• Protection against becoming obsolete
• Leverage existing resources and capabilities
• Response to deferred IPO
• Personal goals
• Become a VC
WHAT ARE YOUR TOP OBJECTIVES AS AN INVESTOR

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RUBICON FUND THESIS
Our thesis: If we can’t add value we don’t invest
How we add value: Network of angel, corporates and
institutional investors across the US, Canada, Europe,
China and Japan
A new model of venture capital: Investors in Rubicon’s
fund may co-invest on a deal-by-deal basis
Sidecar funds pay part of their deal-by-deal carry / profit as
a distribution to the main fund. Better for startups, better
for investors, better for Rubicon: win-win-win

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INVESTMENT FOCUS
Geography: Silicon Valley & New York Offices, US-focus, may invest
globally but prefer Northern Europe (London, Stockholm, Berlin,
Amsterdam, Paris)
Sector focus: Software/internet companies and some hardware/software
Enterprise and Consumer
Stage:
• Raised a min of $1 million already
• Must see at least one other VC in the deal with us
• Current round provides 18 to 24 month runway
• Potential for 10x return
• Seeing significant traction—typically in terms of revenue growth but
also user growth and engagement
• Capital efficient businesses with potential to grow very quickly

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CO-INVESTMENT MODEL
VC Fund
Invests in later
stage seed
VC Fund
Invests in VC
Series A & B
Sidecar Invests
in Later Stage
Growth
LPs Co-
Invest with
the VC Fund
LPs Co-
Invest with
the Fund
LPs may
Invest
until Exit
Investors in our VC fund may co-invest with our fund from later stage
Seed, to Series A to very late stage pre-IPO rounds typically too late for
most VCs. Investors only co-invest in the deals they like
Angels, family offices & corporates deserve the same access to high
quality deals and terms as VCs, not just angel financings

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14 COMPANIES IN 16 MONTHS TARGETING 2 5
Superhuman
Labs

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RELATIONSHIPS: WHO WE INVEST WITH

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Masters of Corporate Venture Capital
Every corporate with $1bn revs should
launch a FoF and CVC
CVC should sit right next to Corp Dev and
Strategy
NEXT BOOK

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Do 2 favors for someone you meet tonight
It’s the magic dust
Make 2 intros for someone from tonight. Good karma will come back to you
Crossing the Rubicon
In the centuries since Julius Caesar led a Roman legion across the Rubicon
River, “crossing the Rubicon” has become synonymous with irrevocably
committing oneself to a bold and revolutionary course of action. At Rubicon
we’re committed to revolutionizing venture capital and building a lasting
venture capital franchise to last many generations.
Andrew@Rubicon.vc
QUESTIONS & DISCUSSION