Attached is my pitch deck for this deal: 30% Premium offered to PINS shareholders for this 1:1 all stock deal. PINS shareholders get 12% of the combined company. 60% EPS-non-GAAP earnings year-3 accretion to PYPL. Synergies come from bringing PayPal merchants to Pinterest to significantly improve ad coverage, using PayPal user data to improve Pinterest's ad relevance, Pinterest merchants defaulting to PayPal for their customers, new ad formats, and significantly more GMV and TPV as a result of these improvements. No significant regulatory opposition expected. PayPal would need to set-up a Chinese-Wall and prohibit Pinterest from using PayPal consumer data to attract consumers to Pinterest. PayPal needs to maintain its merchant independence.

1. +

2. Pinterest + PayPal: The Potential for a Home Run
2
Pros
1) 60% Accretive to Earnings at Year-3 on Revenue Synergies
We imagine a 30% premium ($21.75/sh) for a value of $15B and a deal
structure of a 1:1 stock exchange with PINS shareholders getting 12% of the
combined entity.
2) Massive Self-Reinforcing and Flywheel Benefits
The primary synergies are using PayPal user purchase behavior to improve
Pinterest's ad relevancy, using PayPal merchant information to sell Pinterest's
solutions to these merchants, and to drive PayPal payment volume from the
incremental GMV growth produced by these synergies.
3) Highly Consistent with PYPL's Corp and Business Dev Strategy
4) Massively Improves Pinterest's Ad Relevancy and Targeting; All of
its Stakeholders Benefit
5) Significantly Improves Pinterest's Ability to Recruit New
Advertisers and Expand Internationally
6) Allows Pinterest to Mitigate the Risks from Restrictions on
Cookies, Pixels, and other User Tracking
Chrome, Safari, etc are phasing-out 3rd party cookies and other audience
tracking techniques. Cookies is how Pinterest determines relevancy. Thus far,
PINS has not communicated a strategy to offset these restrictions. However,
7) No Significant Regulatory Concerns are Envisioned
The businesses currently have no overlap and play different roles. Given that
they synergies from the combination generally drive benefits to advertisers,
merchants, and consumers, there seems little reason for regulatory opposition.
Moreover, the deal strengthens a competitor to Google and Amazon.
All rights reserved, Inflection Capital Management, LLC
Cons
1) Large Deal for PayPal. Management Needs the Willingness to
Give it Thorough Consideration and Due Diligencep1
2) Pinterest's Founders (Ben Silbermann and Evan Sharp) Need to
be Willing to Embrace the Greater Good and Support the Deal
Class B shares hold 99.2% of the voting power and 57% (377M/660M) of the
economics. In prior circumstances, this control would have demanded that
PayPal only make an Invited Offer. However, post WeWork, we are suspicious
that any founder shareholder rights and voting control holds sway in the Court of
the Public. Thus, PayPal should be likely to prevail in a Hostile Bid as well.
While the Founders and Board may view this as an unattractive price to sell
given it IPO price of $19. Circumstances have materially changed. Moreover,
PINS shareholders are getting PYPL shares and so they fully participate in the
synergies from the combined entity.
3) Concerns May Arise from PayPal's Marketplace Partners and
Facebook / Instagram
Pinterest is a marketing tool and not a marketplace. Marketplaces themselves
use Pinterest to attract customers and sales. Instagram's concerns are probably
not addressable. However, it will not be able to find a way of punishing PayPal
through its PayPal merchants. Moreover, Instagram may find a way to partner
with PayPal and other payment solutions to drive the coverage and conversion
benefits that we highlight in this report.
No this isn't eBay again. eBay is a marketplace where the transaction is
completed on its marketplace. Pinterest is a source for inspiration and demand
generation; sales leads are completed on the advertiser's own landing page
under its own terms. Yes, PayPal would be using the data received from
shopper behavior on eBay, Shopify, and other marketplaces to influence ad
placement on Pinterest, but not the placements of ads on other marketplaces.
This merger would need to forbid the use of PayPal data for driving users to
Pinterest. Doing so would undermine PayPal as an agnostic payment's provider.
Behavior remedies are typically less than ideal.
4) Depth and Duration of C19 Recession is Big Unknown

3. Explaining Pinterest
Pinterest is a unique platform as it plays all along the sales funnel vs. Facebook which sits in the
middle, expanding out from there, and Google which distinctly occupies the end of the sales funnel.
PayPal would allow Pinterest to uniquely extend itself down to the end of the sales funnel (the
purchase) while not compromising Pinterest's user experience and purpose (we argue that it
would enhance the experience) and without compromising PayPal's other marketplace and
merchant relationships.
3

4. Explaining Pinterest: Ad Units
4All rights reserved, Inflection Capital Management, LLC
Targeting:
 Interests
 Keyword
 Audience
Goals
 Standard: view ad
 Watch video
 Shopping (views, engagement, click-throughs,
purchase)
 App installs
Promoted Pins appear in the home feed and search results just like a
regular Pin except that they’re boosted and targeted to deliver way more
reach. After a Pinner shares it, the “Promoted” label goes away and
subsequent repins are considered earned media. In other words, the
advertiser gets added exposure for "free". When a user taps or clicks your
ad, they’re taken directly to your landing page.

5. Explaining Pinterest Ad Units: "Shop The Look"
5All rights reserved, Inflection Capital Management, LLC
Pinterest user
taps/clicks on Shop The
Look and they are
bounced to the
advertiser's landing
page

6. Explaining Pinterest Ad Units: "Shop The Look"
6All rights reserved, Inflection Capital Management, LLC
This Merchant
Doesn't Use
PayPal., i.e
Cross-Sale
Opportunity
This Merchant
Already uses
PayPal.

7. Coverage:
 No idea as to why I’m being shown ads from Purple and Manscaped; never visited either website. Thus, 2 of the 5 ads are totally random in nature
and irrelevant. Why Pinterest is using page-1 inventory to display irrelevant ad inventory is a puzzle. We suspect that this is because the lack
sufficient relevant inventory due to a lack of advertising campaigns.
Pinterest uses personalization cookies, pixels, and SDKs. (Pixels deliver information or behaviors to a server. Cookies store that information in a
user’s browser so the server can read it again later. For mobile, a publisher can use an SDK to serve ads in an app on the smartphone.
 We suspect that Pinterest does not have a robust set of 1st party data to inform its sales teams doing merchant recruitment. Using PayPal's buyer
and merchant data would allow Pinterest the insights for a highly targeted and effective advertiser recruitment campaign.
 Should a Pinner register onto the site with its PayPal credentials, their PayPal purchase history could be used to display more relevant adds to
Pinners. More relevant adds, leads to higher conversions, which draws in more advertisers.
Pinterest Deficit:
7
Allrightsreserved,InflectionCapitalManagement,LLC
1) www.facebook.com/iq/insights-to-go/6m-there-are-more-than-6-million-active-advertisers-on-facebook
 Only 1.3m Advertisers vs. Over 7M on Facebook.com1
 Only $1.1B in Revenue (2019) vs. $20B for Instagram2

8. Sign up with PayPal*
Why with PayPal
* No need to enter your personal info with
merchants and for shipping details.
* PayPal Protection for purchases.
* Your history allows for more relevant
inspiration on Pinterest and less spam.
* $50 in PayPal points for doing so
Mock-up of Pinterest Log in  While Pinterest users may be wary of sharing their PayPal identity
with Pinterest, honesty and shared benefits should be able to win
many users over to self-register.
 PayPal and Pinterest should also be able to create audience panels
so inform and enhance its ad targeting and improve upon
relevancy. PayPal conversions and behavior purchase tracking will
also greatly enhance ad relevancy. Net-net, there are significant
virtuous cycle and flywheel benefits to be had.

9. Benefits to Pinners for Using PayPal
9All rights reserved, Inflection Capital Management, LLC
Buyer Advantage #1:
No need to enter payment info, address, and personal information
Buyer Advantage #2:
PayPal buyer protections enforced
Buyer Advantage #3:
Earning PayPal buyer points and Honey Science discounts
Buyer Advantage #4:
Seamless currency conversion for cross-border purchases

10. +
Revenue Synergies

11. Drive sales
Chose from a selection of advertising
products, including Pinterest, to bring
consumers to your store front that are
seeking inspiration from your products,
curation, and merchandising.
Learn about our customer acquisition and
advertising solutions
Pinterest-Side Synergies
Product Mock-up
Lift: Ads informed by shopper's purchase
history are 4X more likely to be clicked upon
and 8X more likely to convert to a sale.***
PayPal uses its direct sales and self-serve
capabilities to cross-sell PayPal merchant
accounts on using Pinterest for advertising.
PayPal's merchant data should inform which
merchants can benefit from using Pinterest
that are not using Pinterest, or that could
benefit from using Pinterest more. Thus, the
cross-sale targeting would have a rich set of
data which would allow for quick penetration.
1) Advertiser Coverage Improvements 2021 2022 2023 2024
PayPal Merchant Accounts (million) 29 33 38 44
Incremental Penetration of PayPal Merchants 7.5% 10.0% 11.3% 12.5%
Incremental Merchants Cross-Sold onto Pinterest 2 3 4 6
Ad Revenue Per Sold PayPal Merchant $600 $800 $1,200 $1,400
Revenue $1,309 $2,677 $5,195 $7,744
EBITDA (60% incremental) $786 $1,606 $3,117 $4,646
Note: FaceBook advertisers spent $8K per year on average globally in '18. This equates to $14K in 2024 in nominal terms

12. Pinterest-Side Synergies
 Unfortunately, we have found no authoritative work, or data on benchmarking Pinterest's ad relevancy versus other platforms, i.e. how
much is left to optimize. However, acidotically we can observe that its targeting is far inferior to Google's, Amazon's, general ad
servers that rely on cookies, etc. We know the factors that drove Google to be The King of Relevancy: massive searcher frequency,
massive SEO/SEM investments by advertisers, substantial A:B product testing, and new products like Gmail and Travel which
improved Google's targeting.
 Consequently, the "Improvement from..." row shown below is only a WAGs. Whether the potential improvement is 20%, 50%, or 200%
remains to be determined. That said, we use these Improvements and compound them with the other lifts.
 We know from PayPal's statistics* that PayPal use lifts conversion by up to 89%*. A lot of Pinterest advertisers use PayPal, some don't.
We do not know the mix and our rough sampling suggests the 75% of Pinterest advertisers use PayPal as a choice of payment.
 Assuming that the remaining 25% adopt PayPal and that as a consequence these 25% experience at least a 60% improvement in
conversion, then through auction-based pricing dynamics, a portion of the improvement should work its way back to Pinterest though
increased advertising volume and pricing, i.e. that advertisers increase ad spend until the marginal cost = marginal profit contribution.
* https://www.braintreepayments.com/blog/a-new-study-shows-paypal-helps-improve-checkout-conversion/
2) Relevancy Improvements on CTR 2021 2022 2023 2024
Pre-acq PINS Revenue + New Coverage $2,541 $4,909 $8,827 $12,976
PINS Ad Mix from Consumer Goods 75% 75% 75% 75%
Relevent Ad Revenue $1,906 $3,682 $6,620 $9,732
Improvements from Using Buyer Behavior 20% 30% 40% 50%
Revenue Lift $381 $1,104 $2,648 $4,866
EBITDA (60% incremental) $229 $663 $1,589 $2,920
3) Conversion Improvements (Click to Conversion)
Pre-acquistion PINS Revenue $1,232 $2,232 $3,632 $5,232
PINS Ad Mix from Consumer Goods 75% 75% 75% 75%
De Novo Non-PayPal Usage 25% 25% 25% 25%
Relevent Ad Revenue $231 $419 $681 $981
Lift to Conversion for Seller & Rev Flow to PINS 60% 60% 60% 60%
Revenue Lift $139 $251 $409 $589
EBITDA (60% incremental) $83 $151 $245 $353

13. Pinterest-Side Synergies
 Facebook has seen substantial increases in its ad revenue due to new advertisers, micro-targeting, and new products. Pinterest has
also seen revenue growth from new products, products that are similarly seen on Facebook and Instagram. However, PayPal would
bring a new set of capabilities and resources to Pinterest to develop more new products and at a faster pace than would exist otherwise.
 Estimating what the benefit from the PayPal-inspiration on Pinterest's new products and the associated revenue is highly speculative in
their amounts, but not in the reasoning. To approximate what the amount may be, we estimate what the Retail GMV is from Pinterest-
inspired commerce (we assume that 6% of the GMV value is spent on Pinterest advertising). We then assume that Pinterest+PayPal can
develop new products that can increase Pinterest's take-rate of that by 50 bps (an 8% lift to advertising). Our gut-instinct tells us that
this estimate is far too low. However, we will keep this level of conservatism.
 40% of PayPal's TPV is international. After a merger, PayPal should easily be able to massively accelerate Pinterest's international
expansion through introducing it to PayPal's merchants and promoting it in its other ecosystems. The International Platform Expansion
revenue estimates shown below are simply a WAG. Additionally, we would expect this revenue to have much higher associated costs
given that it is footprint expansion. Consequently, we use a low 20% incremental margin.
4) New Ad Formats 2021 2022 2023 2024
Pre-acq PINS Revenue X 75% (i.e. Goods) $924 $1,674 $2,724 $3,924
Coverage Improvement Revenue $1,309 $2,677 $5,195 $7,744
Relevancy Improvement on CTR Revenue $381 $1,104 $2,648 $4,866
Total Affected Revenue $2,614 $5,455 $10,567 $16,534
on estimated Retail GMV of... $43,574 $90,920 $176,109 $275,560
Take-rate improvement of 0.5% yields Revenue of $218 $455 $881 $1,378
Revenue $218 $455 $881 $1,378
EBITDA (50% incremental) $109 $227 $440 $689
5) International Platform Expansion
US business expanded globally $125 $250 $500 $1,000
EBITDA (20% incremental) $50 $100 $200

14. PayPal-Side Synergies
 The PayPal affected revenue for Pinterest is predicated upon a volume lift of business (i.e. GMV) for Pinterest's merchant advertisers.
That incremental volume also equates to incremental payments, and payment volume.
 We assume that PayPal is used 75% of the time with this GMV, which then becomes PayPal's payment volume (i.e. TPV).
 This PayPal synergy benefit from Pinterest is the ecosystem-reinforcing dynamic that PayPal uses in evaluating mergers and selecting
targets. Consequently, it is this strategic benefit that likely makes Pinterest such a compelling candidate to PayPal's management.
6) Merchant Services 2021 2022 2023 2024
Pre-acq PINS Revenue X 75% (i.e. Goods) $924 $1,674 $2,724 $3,924
Assumed 50% used PayPal previously, lifted to 75% $231 $419 $681 $981
Revenue from..
Coverage Improvements $1,309 $2,677 $5,195 $7,744
Relevancy Improvements $381 $1,104 $2,648 $4,866
Conversion Improvements $139 $251 $409 $589
New Ad Formats $218 $455 $881 $1,378
Total Affected Revenue $2,278 $4,905 $9,813 $15,557
Estimated Associated GMV (1 over 6% of Revenue) $37,966 $81,757 $163,544 $259,284
PayPal TPV Lift (75% of GMV) $28,474 $61,318 $122,658 $194,463
PayPal Transaction Revenue (2.4% take-rate) $683 $1,472 $2,944 $4,667
EBITDA (35% incremental) $239 $515 $1,030 $1,633

15. Total Synergies & Accretion in a Home-Run Scenario
*
 We sum-up the synergies and add them to the pre-synergy PYPL+PINS model. Additionally, we take 75% of the EBITDA from the
synergies and PINS-pre-acquisition and put that into buybacks.
 As shown below the earnings Accretion in a home run scenario is massive. (See Appendix-Slide XX for the pre-synergy roll-up.)
 Given that accretion, the potential impact is also significant, using a 25X the foreword multiple on pro-forma EPS would yield over a
$247/sh stock price by year-end 2023, or a 25% CAGR from current levels**.
* Goodwill and other amortizations are excluded from NI and EPS. ** $106/sh on 4.13.20
Total Synergies 2021 2022 2023 2024
Revenue $2,118 $4,399 $8,639 $13,412
EBITDA $1,337 $2,984 $6,081 $9,752
PYPL + PINS Home Run
Revenue $27,950 $35,731 $45,871 $56,744
Y/Y Change % 28% 28% 24%
EBITDA $7,910 $11,498 $16,460 $22,211
EBITDA Margin % 28.3% 32.2% 35.9% 39.1%
Y/Y Change % 45% 43% 35%
D&A $896 $1,000 $1,160 $1,320
Other Income/Interest $280 $280 $280 $280
Pretax Income $7,294 $10,778 $15,580 $21,171
Tax Expense $1,240 $1,832 $2,649 $3,599
Tax Rate % 17.0% 17.0% 17.0% 17.0%
Adj Net Income $6,054 $8,946 $12,931 $17,572
Shares Outstanding 1,330 1,327 1,322 1,315
Buyback $2,717 $4,431 $7,466 $11,171
Price $145 $205 $290 $370
Shares Reduced 19 22 26 30
Shares Issued via SBC 12 12 12 12
EPS $4.55 $6.74 $9.78 $13.36
% Accretion/Dilution 33% 64% 95%
25X P/E $114 $169 $245 $334

16. 16
1) PayPal is a platform building story though acquisitions:
Eleven acquisitions since 2014, including Honey Science ($4B) last November and iZettle ($2.2B) in 2018. Honey Science is the
test case for PayPal Holdings, Inc (PYPL) to see if it can significantly leverage an acquired business to extend it into the PayPal
merchant base. Moreover, the visibility into the offers on Pinterest would allow PYPL to leverage the offers shown on Honey
Science. (We have not modeled these synergies.) Similarly, PYPL can market Pinterest's ad units to iZettle merchants, further
creating synergies between its assets and putting more momentum onto its flywheel.
All of these acquisitions are about acquiring new and tangential capabilities (along with their customer bases) to reinforce an
ecosystem and flywheel with PayPal as the axis. PYPL's medium-term strategic goal is to have over 1B consumers on the platform
and for these users to engage with it every day. Pinners are a highly engage user base. At 88M average monthly users in the US
and 247M oversees, even assuming that 75% of these have a PayPal account, the remaining 25%, or 88m would make a sizeable
contribution to this 1B objective.
2) PYPL sees itself as a >20% EPS growth story:
Management has been totally transparent that it will use M&A to drive to meet or exceed these targets. PYPL is not an ROIC story.
PYPL's medium-term guidance is 17-18% revenue growth and 20% PF EPS growth over a 3-5 year period. PINS makes this
happen despite the C19 recession. PYPL's other initiatives such as Uber have been significantly undermined by C19. Cross-border
and emerging markets (Brazil and India) are now significantly depressed.
All rights reserved, Inflection Capital Management, LLC
Observations on PayPal Holdings, Inc.

17. Appendix:

18. ICM LLC Estimates Dated 3/30/20
$ Millions Except EPS
PYPL-Stand Alone 2019 2020 2021 2022 2023 2024
Revenue $17,772 $19,994 $24,600 $29,100 $33,600 $38,100
Y/Y Change % 15% 13% 23% 18% 15% 13%
Adj-EBITDA $4,832 $4,998 $6,472 $7,912 $9,352 $10,792
EBITDA Margin % 27.2% 25.0% 26.3% 27.2% 27.8% 28.3%
Y/Y Change % 11% 3% 29% 22% 18% 15%
D&A $701 $753 $850 $950 $1,100 $1,250
Other Income/Interest $280 $280 $280 $280 $280 $280
Tax Expense ($750) ($769) ($1,003) ($1,231) ($1,451) ($1,670)
Tax Rate % 17.0% 17.0% 17.0% 17.0% 17.0% 17.0%
Adj-Net Income $3,661 $3,756 $4,899 $6,011 $7,082 $8,153
Shares Outstanding 1,188 1,188 1,188 1,188 1,188 1,188
Buyback $1,411 $1,129 $1,355 $1,625 $1,951 $2,341
Price $94 $113 $135 $163 $195 $234
Shares Reduced 15 10 10 10 10 10
Shares Issued via SBC 14 10 10 10 10 10
Adj-EPS $3.08 $3.16 $4.12 $5.06 $5.96 $6.86
Y/Y Change % 30% 23% 18% 15%
PINS-CY
Revenue $1,628 $732 $1,232 $2,232 $3,632 $5,232
Y/Y Change % 68% 81% 63% 44%
Adj-EBITDA $19 ($482) $101 $301 $726 $1,366
EBIT Margin % 1.2% 8.2% 13.5% 20.0% 26.1%
D&A $30 $40 $46 $50 $60 $70

19. PYPL+PINS pre-Synergies 2019 2020 2021 2022 2023 2024
Revenue $19,400 $20,726 $25,832 $31,332 $37,232 $43,332
EBITDA $4,851 $4,516 $6,573 $8,214 $10,079 $12,159
EBITDA Margin % 25.0% 21.8% 25.4% 26.2% 27.1% 28.1%
Y/Y Change % 46% 25% 23% 21%
D&A $731 $793 $896 $1,000 $1,160 $1,320
Other Income/Interest $280 $280 $280 $280 $280 $280
Pretax Income $4,400 $4,003 $5,957 $7,494 $9,199 $11,119
Tax Expense $748 $681 $1,013 $1,274 $1,564 $1,890
Tax Rate % 17.0% 17.0% 17.0% 17.0% 17.0% 17.0%
Adj Net Income $3,652 $3,323 $4,945 $6,220 $7,635 $9,229
Shares Outstanding 1,305 1,305 1,305 1,305 1,305
Buyback $1,452 $1,742 $2,091 $2,509 $3,011
Price $132 $158 $190 $228 $274
Shares Reduced 11 11 11 11 11
Adjusted EPS (non-GAAP) $2.55 $3.79 $4.77 $5.85 $7.07
% Accretion/Dilution (8%) (6%) (2%) 3%
Cost Synergies $0 $300 $300 $300 $300
Cost to Achieve $0 ($300) $0 $0 $0
New PYPL + PINS with Cost Synergies
EBITDA $4,516 $6,573 $8,514 $10,379 $12,459
Adj Net Income $3,323 $4,945 $6,469 $7,884 $9,478
Shares Outstanding 1,305 1,305 1,305 1,305 1,305
Adjusted EPS (non-GAAP) $2.55 $3.79 $4.96 $6.04 $7.26
% Accretion/Dilution (2%) 1% 6%

20. Pinterest Audience Claims:
20All rights reserved, Inflection Capital Management, LLC

21. 21

22. Pinterest Audience Claims:
22All rights reserved, Inflection Capital Management, LLC
 Pinterest reports 88M monthly active users which
generate $14 in ad revenue per MAU per year.
 Instagram has 500M monthly and 250 million daily
active users. BBG reported that Instagram generated
$20B in revenue during '19. Assuming that 50% of the
$20 is the US, then that's roughly $20/MAU/year.
 Facebook Blue at 244M generate $95/MAU/year
 ...