November 16, 2020

Investor Day November 16, 2020

Forward-Looking Statements

Some of the information we provide in this presentation regarding our future expectations, plans, and prospects may constitute forward-looking statements. Actual results may differ materially from these forward- looking statements due to various important factors, including the risk factors discussed in our most recent 10- Q filed with the SEC. We assume no obligation to update these forward-looking statements, which speak only as of today.

Also, in this presentation, we will refer to certain non-GAAP financial measures. Reconciliations showing GAAP versus non-GAAP results are available in the appendix of this presentation, which is available on our website at www.microstrategy.com.

Michael Saylor Phong Le Tim Lang Hugh Owen Chairman and President and Chief Technology Officer Chief Marketing Officer Chief Executive Officer Chief Financial Officer

Introduction Phong Le, President and CFO

Company Vision Michael J. Saylor, Chairman and CEO

Product Update and Shift to Cloud Timothy Lang, CTO

Demand Generation and Productive Growth Hugh Owen, CMO

Finance and Growth Phong Le, President and CFO

Q & A

Intelligence Everywhere Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 4 Company Vision Michael J. Saylor, Chairman and CEO Any sufficiently advanced technology is indistinguishable from magic. - Arthur C. Clarke

1993 1999 2003 2008 2014 2017 2019 2020

Industry’s first World’s first First to release a BI reporting and MicroStrategy Enhanced Introduced SaaS relational OLAP web-based BI and fully integrated dashboard available available on cloud support of ML/AI; HyperIntelligence® HyperIintelligence interface personal intelligence reporting tool on iPhone introduced network Dossier® and Workstation

Company Customers Financials

MicroStrategy is the largest Diverse, blue chip customer Profitability at scale with $470mm+ independent publicly-traded base with 4,000+ customers revenue and ~80% gross margin business intelligence company with across 27 countries the leading enterprise analytics platform Repurchased 2.3M shares since High renewal rates with 2018 for $307M ~66% recurring revenue Top-rated product by Gartner for renewing at ~95% agile, centralized BI provisioning Use bitcoin as primary treasury reserve asset, purchasing additional bitcoin with excess ~2,050 employees including ~650 cash, subject to market conditions R&D department and business needs

Q3 2020 was one of the strongest growth and profitability quarters in last decade

Quickly pivoted to customer focus post-Covid in Q2 20 with free education, free upgrades, and on-demand services like Expert.now

Rebuilt go-to-market with virtual marketing events, revamped video-first website, video customer meetings, and remote consulting engagements. Resulted in increased reach, meetings, and productivity combined with decreased costs

Also rebuilding back-office functions to reduce costs while improving agility

Customers more focused on software that is modern, open, and enterprise scale vs. experimental, single- stack, departmental. Consistent with MicroStrategy focus and strengths

Customers also want flexibility and reduced costs, seeing more aggressive shift to data, including data warehouse and business intelligence in the Cloud

Now focusing our technology and go-to-market on moving customers to Enterprise Cloud and SaaS products

Putting our capital structure to work – focus on buying MSTR stock and bitcoin, both have appreciated since we announced strategy

Bitcoin is our primary treasury reserve asset, excess capital > $50M will be put into bitcoin, subject to market conditions and business needs

Consistent with our virtual wave strategies, and improved digital marketing: YouTube views, Twitter views, Website traffic all up

Expect additional upside and synergies over time with go-to-market, R&D, and ultimately company valuation

Michael J. Saylor Phong Le Timothy Lang Hugh Owen W. Ming Shao Chairman and CEO President and CFO SEVP and CTO Chief Marketing Officer SEVP and General Counsel 30+ years at MicroStrategy 5+ years at MicroStrategy 6+ years at MicroStrategy 20+ years at MicroStrategy 20+ years at MicroStrategy

Ponna Aurumugam Joty Paparello Paul Green Jeanine Montgomery Jeremy Price Chief Information Officer Chief HR Officer EVP, Worldwide Consulting Chief Accounting Officer Senior VP, FP&A 2+ years at MicroStrategy 18+ years at MicroStrategy 2+ years at MicroStrategy 4+ years at MicroStrategy 18+ years at MicroStrategy

Intelligence Everywhere Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 11 Product Update and Shift to Cloud Timothy Lang, Chief Technology Officer Modern Analytics Bring data to people, processes, and things

HyperIntelligence MicroStrategy Library™ Dossier

Insights automatically delivered to users Personalized analytics catalog Personalized dashboards

Planned for MicroStrategy 2021™ • Rich-text editor and grid formatting • Pattern matching in HyperIntelligence • New Mac and Windows app to consume dossiers quickly • New visualization gallery and formatting panel • Ability to share cards • Shared bookmarks • Microcharts in grid • QR code and Barcode support • 1:1 and group collaboration • Mobile-specific Dossier design • Extended Search in HyperIntelligence • Built-in HyperIntelligence to highlight in dossiers in • Vertical scrolling for dossiers • Create calculations in HyperIntelligence cards MicroStrategy app • Global filters • HyperIntelligence thresholds • Search for HyperIntelligence cards in MicroStrategy app Intelligence Everywhere Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 13 The MicroStrategy HyperIntelligence Product Suite Answers at your fingertips - whether you’re on the web, a mobile device, or your favorite app

HyperWeb™ HyperMobile™ HyperOffice™ Seamlessly inject intelligence Put intelligence in the palm of your Bring answers to your favorite directly onto words in the hand – by making cards available productivity tools with cards websites and web applications directly on a user’s mobile device. embedded directly into your emails, people use every day. documents, and spreadsheets.

Intelligence Everywhere Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 19 Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 20 MicroStrategy App with Global Search, Embedded HyperIntelligence

Federated Analytics Comprehensive set of SDKs Deploy without compromise Connectors that bring consistency and Embed, customize, and extend into Fully-featured, optimized for your governance to popular analytics tools applications and workflows platform of choice

What’s New this year

• Excel: Import data from dossiers, preserve report formatting. • Administration APIs • Schema object editors in Workstation • Data refresh on Tableau Server • Python SDK for Administration • Create and edit filter objects in Workstation • OOTB connector for PowerBI via a certified connector • Data Modeling APIs • Scripts stored as objects in the Metadata and accessed via Workstation • Performance improvements in connectors. • Embedded HyperIntelligence cards • One-click upgrade with backup on Azure • UX streamlining in Excel, Jupyter and RStudio connectors. • Expanded region support • Build a dossier based on another dossier (MSTR connector) Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 22 Intelligence Everywhere 22 MicroStrategy for Business Users – Excel 365

Intelligence Everywhere MicroStrategyCopyright Confidential © 2020 MicroStrategy – Incorporated.For Gartner All Rights Analyst Reserved. Use Only 23 MicroStrategy for Business Users Enhanced connectors for Power BI and Tableau

Trusted Data

Intelligence applications

Data Scientist

AI Enriched Data

Jupyter Notebook and RStudio Python and R libraries

• Low-code experience for connecting to MicroStrategy, • Programmatic access to MicroStrategy to query finding relevant data, and creating new datasets existing datasets and publish new ones • Reproducible analysis by providing underlying source code • Interoperable with ML platforms / products such as Databricks, DataRobot, Dataiku

from mstrio.dataset import Cube, Report, Dataset

my_cube = Cube(connection=conn, cube_id="...") df = my_cube.to_dataframe()

my_report = Report(connection=conn, report_id="...") df = my_report.to_dataframe()

ds = Dataset(connection=conn, name="Store Analysis") ds.add_table(name="Stores", data_frame=stores_df, update_policy="add") ds.add_table(name="Sales", data_frame=sales_df, update_policy="add" ds.create()

Single version of the truth Mitigate compliance risk Scale to many Bring data consistency and trust to Enable self-service while enforcing data Scale with high performance. users and applications with the protections under GDPR, HIPAA, and more. Distribute personalized analytics across Enterprise Semantic Graph™️. the organization.

What’s New This Year

• Script objects in metadata and Workstation • OpenID Connect platform-wide support • Memory-mapped files result in performance and sizing improvements • Metric editor in Workstation • Optimized queries for Google Big Query. • Administrative REST APIs for automation • Create filters in Workstation • Snowflake and Teradata connectors out of the box. • Application settings management in Workstation • Fact editor in Workstation • SAP oData support for S4/HANA and BW4/HANA • Import/Export environment settings in Workstation • Attribute editor in Workstation • Remote support via improved diagnostics and Expert.Now • Warehouse catalog in Workstation

Scalability Performance Gateway Optimizations • Publish 2x larger cubes and host 2x • Intelligence Server on Windows 10% • SAP S4/HANA Data Import Gateway up to more data on existing hardware with faster across the board 3x faster than commercially available drivers no degradation to user experience by leveraging fast local storage • 30% faster project schema cube publishing • SAP HANA up to 5x faster in multi-source and live report execution across all workflows gateways with attribute lookup caching • 30% faster Google BigQuery time • 20% faster cube incremental refreshes transformations with single-step replace • SQL Function Push-down: • 3x faster string-based Derived Attribute • DateTime (all Diamond Gateways) and Derived Metric evaluation • Percentile (all Diamond and Platinum Gateways)

• 10x increased cache scalability with 1M+ cache entries per server

Optimized for the Cloud Modern Simple New Cloud Object Storage gateways: OAuth authentication New OOTB Drivers: • Amazon AWS S3 • OAuth support for Snowflake and Google • Snowflake, Teradata, SAP HANA • Microsoft Azure Data Lake Storage BigQuery Connectivity Wizard • with • Google Cloud Storage Service Azure AD SSO Snowflake • TLS configuration for all Diamond and Supported File Formats: New gateways: Platinum gateways • • Parquet SAP S/4HANA, BW/4HANA • UX enhancements: • Avro Yellowbrick, IBM IAS • Salesforce, Google BigQuery • ORC New certifications: • Excel, Jupyter Notebook, RStudio • Spark JSON • Oracle 19c / 20c, Oracle Autonomous Data Warehouse Seamless support for partitioned files • Teradata 17, Db2 11.5, PostgreSQL 12 Scalable Apache Spark-based architecture: • Cloud Data Platform 7.1 (Hive, Impala) • MongoDB 4.x • Early adopter validation: imported 1B rows of partitioned Parquet data in <2h into 90GB cube

Reinvent the Customer Experience Expand to New Audiences

Invent Turn-key departmental offerings HyperIntelligence, Open Semantic Graph Hyper.Now. Intel.Now

Consumer User Experience Simple pricing Dossier. Library. Collaboration. Geospatial $10/user/month

Modernize Tooling Workstation. Platform Analytics + Digital marketing strategy Targeted at digital personas Open Platform AWS. Azure. Automated Upgrade. REST. Containerization

(without disruption)

Reduce Adoption Friction Deepen Capabilities Simplify Administration • Free 90 Day Trial • Derived metrics in HyperIntelligence cards • Enterprise security with OpenID Connect

• Launch an environment in four clicks • Use local data (Excel, CSV, Dropbox, • Automatic upgrades including client Google Drive, etc) to build cards software • Seamlessly download Workstation and immediately Web, Mobile, Office connectors with • Automatically provided adoption analytics connectivity pre-established • Hyper SDK allows cards to function on shows who is using your cards web pages without the plugin • OIDC single sign-on with MicroStrategy • Improved environment management for Resource Center • Replace dataset on cards to allow the MicroStrategy platform administrators in same card to be used on different Workstation including usage statistics • Workstation only shows functionality personal or corporate datasets and health status related to HyperIntelligence to simplify usage • Color thresholds for cards based on metric conditions (HyperVision) • Invite new users and assign roles through email

Consumer-grade experiences Embrace and augment popular tools Trusted answers with for every role and popular devices and technologies sub-second response at enterprise scale

• All new MicroStrategy app for viewing content • Embed HyperIntelligence with HyperSDK • Authentication with OpenID Connect (OIDC) • Search and share HyperIntelligence Cards • Python SDK for platform automation • Use Workstation to create and manage filters and Dec 2020 Dec

– schema objects including facts and tables • Author infographic-style dossiers with vertical • Cloud-object file connectors (S3, ADLS2, GCP) scrolling, rich text, responsive design for mobile • Monitor subscriptions, user connections, database • Optimized Snowflake and Teradata gateways devices, and more connections, and cubes from Workstation • One-click backup and upgrade in Azure • Direct messaging and group collaboration • View and apply changes to application and server-level • Performance enhancements for Federated Analytics configuration parameters from Workstation • Personalized organization of Library content integrations

MicroStrategy 2021 MicroStrategy 2021 • Shared bookmarks and automatic updates • Containerized deployment ™ • Reusable templates for corporate branded analytics • Acceleration of OEM and Embedding • Design subscriptions with branded templates content with device-specific layouts • New APIs for schema and application objects • Unify administration and modeling tools on Workstation • Modernized transactions with actions and triggers • Distribute content to SharePoint, OneDrive, S3, and other • Augmented PII masking and data lineage • Threshold-based alerting cloud storage platforms • Automated content testing to enable agile upgrades • Augmented insight discovery • Augment data lineage apps with the Semantic Graph • Optimized deployments for AWS, Azure, and GCP • Parameterized scenario analysis • Productivity bots for Slack and Teams • Authentication through API keys • Personalization and white-labeling • Modernized content embedding SDKs Updates /Updates 2022 MicroStrategy

HyperIntelligence Cloud Embedded

• Most rapidly adopted solution in the • COVID is acting as a catalyst, driving IT • Technology partners are choosing history of MicroStrategy organizations to re-evaluate and plot a MicroStrategy because of our modern, more aggressive shift to Cloud open, independent, enterprise-grade • Provides instant, zero-click access to platform data within existing productivity tools • Market adoption of cloud data warehouse driving improved business results at an offerings is providing a natural • Platform works at scale and can accelerated pace conversation for the future of business support complex technical and intelligence solutions business needs

Intelligence Everywhere Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 34 Demand Generation / Productive Growth Hugh Owen, Chief Marketing Officer Generate Demand and Accelerate Growth

1 Exploit Analytics Market and Cloud Growth

2 Publish High Quality Sharable Content

3 Accelerate Website Traffic

4 Exhibit Products via Video-first Website

5 Integrate Support, Education, Community, and Product

6 Create Registrations via Free Trials

7 Convert Trials by Delivering Value and Removing Barriers

8 Drive Productivity with Digital Go-to-Market

9 Increase Customer Value via Expansion, SaaS, and Cloud

BI Market Growth (Constant Currency) 2019-2024 Revenue ($M) with Growth (%)

FY 19 FY 20 FY 21 FY 22 FY 23 FY 24

Source: IDC, Worldwide End-User Query, Reporting, and Analysis Software Forecast Update, 2020–2024, #US46880220

Customer Successes Stories Practical Advice and Expertise Real-world stories on how organizations solve problems and overcome MicroStrategy Experts sharing valuable and practical information to challenges using MicroStrategy’s products and services. help prospects and customers be successful, fast.

Advertising: Hyper for Teams Advertising: Hyper for Lines of Business Video-first placement via YouTube and Google targeted at Video-first placement via YouTube and Google targeted at LOB senior analysts with intent to try or previous interest. prospects searching for solutions and with intent to try.

Start a Demo the Class Product

Apply for Trial the a Job Product

Hyper.Now / Intel.Now 90 Day Free Trial Architect Pass / Expert.Now 30 Day Free Trial

Start Trial Start Trial

Connect data Take Courses

Build Cards Use Expert.Now

Share Cards Upgrade Trial

Upgrade Trial

Hyper.Now Intel.Now Every application, instantly smarter and faster. Modern BI for every user, on popular devices. Create, view, share, and embed cards. Create, view, share, and embed dossiers. HyperIntelligence for Web, Mobile, and Office. MicroStrategy for Web, Mobile, and Desktop.

2021 November 2020.

$10 user / month $10 user / month Credit Card or Invoice Credit Card or Invoice

Virtual Conference Then Now Product Keynotes

In-person events Digital events (more events, 8+more Channels reach) of Shows

Driving Flying Hoteling Zooming (lower costs, no waiting)Customer Stories

Wet signatures Electronic signatures (speedPartner close Solutionsprocess)

Hyper Solutions Lengthy upgrades Immediate upgrades (stability, performance) 2021 Education Courses On site delivery Remote delivery (global staffing, no waiting) 1:1 Tech Talks In-person World Virtual World (10,000s attendees) Workshops

Free to Attend

From To

Experimental Enterprise Grade (security, trust, economies of scale)

Teams Departmental (unify, certify, material impact)

Departmental Company-wide (break siloes, single version of truth)

On-prem Cloud (reduce costs, increase impact)

Private Cloud SaaS (reduce costs, increase impact)

1 Exploit Analytics Market and Cloud Growth

2 Generate and Publish High Quality Sharable Content

3 Capture Attention And Drive Traffic to Website

4 Exhibit Our Products and Services Via Video-first Website

5 Integrate Support, Education, Community, and Product

6 Create Registrations Via Free Trials

7 Convert Trials by Delivering Value and Removing Barriers

8 Drive Productivity With Digital Go-to-Market

9 Increase Customer Value Via Expansion, SaaS, and Cloud

1 Largest independent publicly-traded BI company, leading enterprise analytics platform

2 Diversified blue-chip customer base with ~95% renewal rates

3 Healthy revenue profile: 65%+ recurring, 90%+ gross margin in license and support

4 Strong growth drivers → highlighted by cloud transition

5 Significant cost structure optimization, with additional near-term opportunity

6 History of cash flow generation

7 Meaningful balance sheet with bitcoin upside

8 Executing on plan – Q3 2020 was best quarter in decade

9 Valuation upside with revenue, EBITDA, and digital asset growth

Intelligence Everywhere Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 48 1. We are the Top BI Company with the Top Product Top-rated by Gartner Leader on the Forrester Wave Product of service scores for Agile, centralized BI The Forrester Wave™: Enterprise BI Platforms (Client- provisioning managed)–Q3 2019 MicroStrategy 4.34 HQ: Tysons Corner, VA MicroStrategy NASDAQ: MSTR TIBCO Software 4.11 Challengers Contenders Strong performers Leaders www.microstrategy.com Stronger 3.97 Salesforce Current offering TIBCO 3.79 MicroStrategy Birst Software 1989 30 years #1 SAS 3.78 Sisense Founded CEO Tenure Product Tableau 3.60 Yellowlin . ThoughtSpot Software SAS Qlik Tableau 3.59 Information Builders Birst

ClearStory Data 3.58 IBM ThoughtSpot . 4,000+ 39 27 Microsoft Sisense 3.55 Customers Cities Countries OpenText Oracle 3.44

Logi Analytics 3.40

9 35 3 Microsoft 3.40

Support Field Service Development Qlik 3.39 Centers Centers Centers Domo 3.38 Weaker Current Information Builders 3.38 offering Weaker Stronger Innovator and industry leader in web, IBM 3.07 Strategy Strategy mobile and cloud-based analytics Looker 3.01

SAP 2.91

Amazon Web Services 2.26 (Amazon Quick Sight)

Source: Gartner (Critical Capabilities for Analytics and Business Intelligence Platforms, March 2020), Forrester (The Forrester Wave™️: Enterprise BI Platforms, July 2019)

Recurring Revenue Distribution by Industry* Other 7% Apparel 2% 11% 9% Top account recurring revenue as Top 10 accounts recurring Technology % of total revenue as % of total 9%

Banking Retail 17% 22 yrs $3M+ 11% Average lifetime of top Average ARR of top 15 customers 15 customers Pharmaceuticals Communications/Media 4% 8% Manufacturing 4% Consulting > 700 ~95% Insurance 5% Customers spend Renewal rates Government $100K+/yr 10% Grocery 8% 8%

*based on top 100 accounts by revenue

Goals MicroStrategy Products Benefits

• Shift from financial center ✓ Consistent reporting across 5,000+ manager corkboard reporting to financial centers real-time financial center results HyperIntelligence and forecast ✓ More time to analyze and make • Single source of truth, single set decisions of dashboards and reports ✓ Ability for district managers to • Modernize financial centers, distribute data reports to teams upskill employees Dossier ✓ Improved decision-making ability for Challenges district managers, driving improved results • Team required full POC to demonstrate next-gen analytics, Enterprise tight integration and partnership Semantic Graph with hardware vendor • Consulting resources utilized to speed time-to-market

Goals MicroStrategy Products Benefits

• Provide comprehensive data ✓ Enhanced mobile product, fully analytics / visualizations with a integrated with handheld mobile simple interface Mobile device/scanner scanning SKUs • Fully enable all store users with real time SKU information – ✓ Easier maintenance and improved inventory, sales, performance security compared to building in-house alternative • Rapid deployment with scalability SDK ✓ Increased productivity, supervision, and support Challenges ✓ Empowered 20,000+ store managers, • Simple to use application, intuitive UI, and department heads with inventory, performance at scale product sales and store KPIs Dashboards • Rapid roll-out, iterations, and changes utilizing MicroStrategy consultants

Intelligence Everywhere Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 52 2. Leading Global Cybersecurity Company Provides Deep Real- Time Insights to Customers by Embedding MicroStrategy

Goals MicroStrategy Products Benefits

• Provide customers with near real-time ✓ Superior build vs. buy decision, visibility into firewall utilization, enabling allows software company troubleshooting of critical network and Open APIs resources to focus on their areas security issues of expertise • Visualize large volumes of customers’ data from various sources in a cloud portal ✓ Easy-to-use solution for end user, fully white-labeled and embedded

Challenges Real-time Analytics ✓ Accessed by ~500 internal users focused on customer support as • Integrate many sources of data, scale well as thousands of external without compromising performance tenant users • Customized visualizations ✓ Rapid solution deployment • Provide near-real time insights with large Cloud enabled the company to capitalize data volumes on increased customer demand • Rapid growth company needed staff due to the virtual office augmentation for development environment

Revenue by Type ($M) Gross Margin by Revenue Type

98% 97% 94% 93% 92% $115 $93 $88 $87 $87 95% 94% 93% 90% 91% $83 $89 $84 $77 $77 $30 82% $31 $32 $29 $32 81% 80% 79% 80%

58% 58% $285 $289 $296 $292 $287 54% 48% 50%

FY 16 FY 17 FY 18 FY 19FY 20 TTM* FY 16 FY 17 FY 18 FY 19 FY 20 TTM* Support Subscription Other Services Product License Product License Support Subscription Total Gross Margin

65%+ of revenue is recurring (TTM) 78% of revenue at 90%+ Gross Margin (TTM)

*FY 20 TTM is based on Q4 19 through Q3 20 actual results

HyperIntelligence Cloud Embedded

License purchase shift Customer migrations New SAAS Improved from on-prem to Cloud from on-prem to Cloud offerings: Hyper.now subscription billings and Intel.now Current Subscription Billings ($M) • Purchasing shift from on- • Convert existing on-premise • Hyper.Now premise to Cloud in customers to Cloud (Hyperintelligence) launched $11.0 customers and prospects Nov 16, 2020 $9.9 • 30-60% revenue uplift, 30-60% $9.3 $9.4 • ~50% revenue upfront, gross margin uplift • Intel.Now (Business $8.0 recognized ratably, 3-year • > 10% customer shift in 2021 Intelligence) to launch in break even 2021 $6.9 • > 5% revenue shift in 2021 • 100% incremental revenue, $5.3 upside in 2H 2021 and beyond • Excellent land and expand opportunity

Q1 19 Q2 19 Q3 19 Q4 19 Q1 20 Q2 20 Q3 20

* Please refer to the Appendix for a reconciliation of subscription services revenues to current subscription billings

Illustrative New Cloud vs. On-prem Comparison Financials Cloud Growth Factors • Multiple drivers impacting shift to BI in cloud: 1) macro factors including work Cumulative Revenue ($M) $2.4 from home, focus on cost reduction, 2) prevalence of DW in cloud, 3) greater cloud adoption in large enterprises $1.8 $1.8 • MicroStrategy Cloud Enterprise solution is at parity with on-prem, AWS, and $1.6 Azure, and working on container strategy $1.4 $1.2 $1.2

$0.6 Cloud Growth Financials • Subscription revenue typically ~50% less than perpetual in year 1; with breakeven point after year 3 Year 1 Year 2 Year 3 Year 4 • Example comparison of revenue streams: • On-prem: $1M perpetual license, $200K recurring product support Perpetual Cloud • $600K recurring subscription revenue (includes license + support + hosting)

Cloud Conversion Factors Illustrative Comparison Financials ($M)

• Existing customers moving to cloud to 1) reduce fixed costs, 2) Revenue Incremental Gross Margin upgrade software regularly and seamlessly, 3) upskill admins to $1.8 architects and developers $1.6 • One annual price includes software, support, infrastructure, $0.2 upgrades $1.4 $0.2 $0.2 • Add-ons include HyperIntelligence, managed admin services, $1.2 managed application services $0.2 $0.2 $1.0 $0.8 $0.6 Cloud Conversion Financials $1.0 $1.0 $1.0 $0.4 $0.9 • Converting customer from on-premise support to subscription cloud $0.2 results in 30-60% immediate uplift in revenue; 10-20% uplift each from licenses, support, hosting $- • Results in 30-60% uplift in gross margin Support Subscription Support Margin Subscription Revenue Revenue Margin • Customer breakeven point is in Year 1, with near immediate cost benefits Baseline Revenue Term Uplift Support Uplift Hosting Uplift

FY 18 FYFY 19 FY 20 Actual ($M) ActualFY ($M)19 Run Rate* ($M)

$79 $81 $74 $99 $107 $103

$202 $189 $144

*Run Rate = Q1-Q3 20 Actuals and Q3 20 as a proxy for Q4 20 Costs are non-GAAP G&A, R&D and S&M costs. Please refer to the Appendix for a reconciliation of certain Non-GAAP Operating Expenses.

35% Free Cash Flow (non-GAAP; $M) 28% 30%

25% 21% 20% 15% 15% $146 10% 10% $108 6% $74 5% 1% $29 $35 $4 0% FY 15 Actual FY 16 Actual FY 17 Actual FY 18 Actual FY 19 Actual FY 20 TTM*

Prioritize Invest for Prioritize profitability profitability growth and grow with MicroStrategy 2020

Executed company-wide restructuring in In Q2 17, announced a 3-year plan to reinvest for growth Shifted focus to optimization starting in 2H 19 2H 14 • Increased S&M spend by ~17% in FY 18 • Fully virtual model driving reduced T&E and marketing • Closed inefficient development centers and • Increased R&D headcount ~150 to ~750 in FY 19 • Rationalized R&D headcount from 750 to 666 satellite offices • Developed HyperIntelligence and MicroStrategy Cloud™️ • Virtual demand generation reaching more customers, • Streamlined business processes more quickly • Rebuilt the platform, modernized tooling

*FY 20 TTM is based on Q4 19 through Q3 20 actual results Please refer to the Appendix for a reconciliation of Non-GAAP FCF Intelligence Everywhere Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 60 7. Unique Balance Sheet Strategy Uses Bitcoin to Provide Asymmetric Upside and Energize New Investors

Bitcoin Value ($M) Treasury strategy • Invest up to $250M in share repurchases • Utilize bitcoin as primary treasury reserve asset • $50M needed to run day-to-day business $621

$425 $381 Bitcoin value

Cost Basis 9/30/20Book Value 9/30/20 Market Value 11/13/20 • Purchased ~38,250 bitcoins in Q3 20 for $425M (average price of $11,111 per bitcoin) • Book value of bitcoin was $381M at 9/30/20 (average price of $9,954 per bitcoin) Share Repurchase Value ($M) • Market Value of bitcoin at 11/13/20 ~$621M (average price of $16,239 per bitcoin)

Share repurchase • In Q3 20 repurchased 432,313 shares for $61M as part of Dutch auction tender offer $111 $123 (at price of $140 per share) $73 • In FY 20 repurchased 877,082 shares for $123M (average price of $140 per share) • Since Q4 18 repurchased 2.3M shares for ~$307M (average price of $135 per share) FY 18 FY 19 FY 20

Highest Q3 product license Highest Q3 total revenue Strong adoption of cloud revenue since 2016, up 56% since 2016, up 6% offering, 87% increase in year-over-year year-over-year subscription billings* year-over-year

Product Lic. Revenue ($M) Total Revenue ($M) Current Subscription Billings ($M)

$11.0 $30.1 $29.6 $133.5 $9.9 $127.4 $9.3 $9.4 $115.4 $117.7 $119.7 $111.4 $110.6 $8.0 $20.1 $6.9 $18.3 $19.0 $5.3 $14.8 $12.6

Q1 19 Q2 19 Q3 19 Q4 19 Q1 20 Q2 20 Q3 20 Q1 19 Q2 19 Q3 19 Q4 19 Q1 20 Q2 20 Q3 20 Q1 19 Q2 19 Q3 19 Q4 19 Q1 20 Q2 20 Q3 20

* Please refer to the Appendix for a reconciliation of subscription services revenues to current subscription billings.

2019 2020 2021 EV Long-Term Actual TTM* Projections Multiples** Opportunity

Revenue 2.4X >10% growth Negative Flat Growing Revenue multiple Revenue growth

Operating 15X >25% Income $9M $50M $60-90M EBITDA multiple EBITDA margin (non-GAAP) (non-GAAP) (non-GAAP)

*2020 TTM is based on Q4 19 through Q3 20 actual results - Please refer to the Appendix for a reconciliation of certain Non-GAAP Operating Income ** Hypothetical Enterprise Value multiple uses analyst consensus 2021 revenue of $485M and adjusted EBITDA of $78M, net cash as of 9/30/20 of $53M, Digital Asset market value $621M with bitcoin price 11/13/20 $16,239, MSTR market cap of $1.85B with MSTR stock price as of 11/13/20 of $192.27

1 Largest independent publicly-traded BI company, leading enterprise analytics platform

2 Diversified blue-chip customer base with ~95% renewal rates

3 Healthy revenue profile: 65%+ recurring, 90%+ gross margin in license and support

4 Strong growth drivers → highlighted by cloud transition

5 Significant cost structure optimization, with additional near-term opportunity

6 History of cash flow generation

7 Meaningful balance sheet with bitcoin upside

8 Executing on plan – Q3 2020 was best quarter in decade

9 Valuation upside with revenue, EBITDA, and digital asset growth

Reconciliation of GAAP to Non-GAAP Income (loss) from Operations FY 18 FY 19FY 20 TTM^ Revenue $498 $486 $483 Cost of Revenues $99 $100 $95 Operating Expenses $394 $387 $392 Income (loss) from Operations $4 $(1) $(4) Operating Margin % 1% 0% -1% Stock-Based Compensation $15 $10 $10 Digital asset impairment losses $0 $0 $44 Non-GAAP Income (loss) from Operations $19 $9 $50 Non-GAAP Operating Margin % 4% 2% 10%

Reconciliation of certain Non-GAAP Operating Expenses FY 18 FY 19 Q1 20 Q2 20 Q3 20 Q4 20 Run Rate* FY 20 Run Rate* GAAP: G&A Expense $86 $87 $21 $19 $20 $20 $80 R&D Expense $102 $109 $26 $26 $27 $27 $105 S&M Expense $206 $191 $40 $35 $35 $35 $145 Stock-Based Compensation G&A Expense $7 $5 $2 $1 $2 $2 $6 R&D Expense $3 $2 $1 $1 $1 $1 $2 S&M Expense $4 $2 $0 $0 $0 $0 $1 Non-GAAP: G&A Expense $79 $81 $19 $18 $18 $18 $74 R&D Expense $99 $107 $25 $25 $26 $26 $103 S&M Expense $202 $189 $39 $35 $35 $35 $144 ^FY 20 TTM is based on Q4 19 through Q3 20 actual results *Run Rate = Q1-Q3 20 Actuals and Q3 20 as a proxy for Q4 20 Intelligence Everywhere Copyright © 2020 MicroStrategy Incorporated. All Rights Reserved. 66 Investor Day Non-GAAP Reconciliations ($M)

Reconciliation of Subscription Services Revenues to Current Subscription Billings

Q3 18Q4 18Q1 19Q2 19Q3 19Q4 19Q1 20Q2 20Q3 20 Current deferred subscription services revenue $11.7$13.5$15.6$15.4$12.8$16.6$16.6$17.9$19.5 Subscription services revenues $7.2$7.1$7.1$7.1$7.9$7.3$8.0$8.0$8.3 Change in current deferred subscription services revenue (quarter) $(2.1)$1.8$2.1$(0.2)$(2.6)$3.7$0.0$1.4$1.6 Current Subscription Billings $5.1$8.9$9.3$6.9$5.3$11.0$8.0$9.4$9.9

Non-GAAP Free Cash Flow reconciliation

FY 15*FY 16FY 17FY 18FY 19 FY 20 TTM Net cash provided by operating activities $150$111$78$11$61$37 Purchases of property and equipment (investing activities) $(3)$(2)$(4)$(7)$(10)$(2) Gain from Domain Name Sale, net of tax $(22) Free Cash Flow (Non-GAAP) $146$108$74 $4$29$35 FCF Margin (Non-GAAP) 28%21%15% 1% 6%10%