Why the patient money in enterprise software creates the most extraordinary wealth
Everyone knows B2B software scales beautifully—recurring revenue, sticky customers, predictable growth. Even in the age of AI. But here’s what most investors miss: if you stick with these companies for decades, through IPO and beyond, the returns become absolutely astronomical.
We’re not just talking about pre-IPO venture returns. Even investors who bought shares on IPO day and held for the long haul have seen gains that dwarf every other asset class. The patient capital that believed in enterprise software’s compounding power has been rewarded with returns so extreme they redefine what’s possible in public markets.
The numbers are staggering: 9,000%+ gains that turned IPO investors into generational wealth creators. These B2B founders didn’t just build great companies—they engineered some of the most lucrative long-term investments in modern history.
These are their stories.
The Complete Split-Adjusted Leaderboard: The Real Returns
Splunk acquired by Cisco in 2024 for $157/share, but founder was CEO at IPO. Oracle founded pre-SaaS but performance so outstanding, adding as our bonus. Wow Larry!
The Mind-Blowing Reality
- Founder Dominance: 8 out of 10 top performers (80%) had founder CEOs at IPO.
- The Million-Dollar Club: The top 3 companies alone turned $30,000 into over $2.1 million.
- Oracle Off the Charts: Larry Ellison’s 39-year wealth creation story sits in its own stratosphere.
Source: SaaStr.ai. All prices split-adjusted and current as of June 2025.
The Elite Ten: Returns That Redefined Possible
1. Salesforce: +9,296% (Marc Benioff – Founder)
IPO Date: June 2004 | Split-Adjusted IPO Price: $2.75 | Current: $258
The numbers are so staggering they require a double-take. After accounting for Salesforce’s 4-for-1 stock split in 2013, Marc Benioff’s cloud computing revolution delivered returns that approach 100x.
Benioff didn’t just create a company—he created an entire industry. When Salesforce went public in 2004, cloud software was still a radical concept. His vision of “No Software” seemed almost absurd to enterprise buyers accustomed to on-premise installations.
What Made It Legendary:
- Category Creation: Literally invented cloud software for enterprises
- Platform Vision: Built the AppExchange ecosystem that became a $4B+ marketplace
- Relentless Innovation: Never stopped evolving from CRM to AI to complete customer platform
- 20-Year Execution: Sustained hypergrowth for two decades as a public company
$10,000 invested at IPO would be worth $939,636 today.
2. Shopify: +6,159% (Tobias Lütke – Founder)
IPO Date: May 2015 | Split-Adjusted IPO Price: $1.70 | Current: $106
Tobias Lütke started Shopify because he couldn’t find good e-commerce software for his snowboard business. What began as personal frustration became one of the greatest wealth creation machines ever built.
After Shopify’s 10-for-1 split in 2022, what looked like strong returns became absolutely extraordinary. The technical founder’s platform approach proved prescient as e-commerce exploded from niche to mainstream.
What Made It Extraordinary:
- Perfect Timing: Caught the e-commerce wave through pandemic acceleration
- Platform Strategy: Built an ecosystem where millions of merchants could thrive
- Developer-First: Created APIs and tools that developers actually wanted to use
- SMB Democracy: Made professional e-commerce accessible to any entrepreneur
$10,000 invested at IPO would be worth $625,941 today.
3. ServiceNow: +5,605% (Frank Slootman – Non-Founder)
IPO Date: June 2012 | IPO Price: $18 | Current: $1,027
The lone non-founder exception that proves the rule. Frank Slootman’s execution on IT service management created a category-defining platform that enterprises couldn’t live without. ServiceNow’s returns demonstrate that while founder leadership usually wins, exceptional professional CEOs can occasionally deliver legendary results.
Slootman’s track record (he also led Snowflake and Data Domain to successful exits) shows that experienced software executives with deep category expertise can create massive value.
$10,000 invested at IPO would be worth $570,478 today.
4. HubSpot: +2,078% (Brian Halligan – Founder)
IPO Date: October 2014 | IPO Price: $25 | Current: $544
Brian Halligan and Dharmesh Shah didn’t just build marketing software—they created an entire movement. “Inbound marketing” became a philosophy, a methodology, and eventually a complete customer platform that redefined how businesses attract and retain customers.
The founder-CEOs proved that category creation plus excellent execution can generate massive returns, building a complete customer platform from their original marketing automation roots.
What Made the Difference:
- Methodology + Software: Created inbound marketing as a discipline, then built tools to execute it
- Content Strategy: Used their own platform to become thought leaders in their space
- Platform Integration: Connected marketing, sales, and service in one unified system
- Freemium Model: Lowered barriers to entry while building massive user base
$10,000 invested at IPO would be worth $217,784 today.
5. Zscaler: +1,744% (Jay Chaudhry – Founder)
IPO Date: March 2018 | IPO Price: $16 | Current: $295
Jay Chaudhry’s cloud security vision proved that even “boring” cybersecurity could generate extraordinary returns. By building security architecture for the cloud era, Zscaler became essential infrastructure for the remote work revolution.
Chaudhry had already founded and sold multiple security companies before Zscaler, giving him unique insights into what enterprises really needed for cloud security.
What Made It Special:
- Cloud-Native Architecture: Built security for cloud-first enterprises
- Zero Trust Model: Pioneered the security framework that became industry standard
- Remote Work Enabler: Perfect positioning for the distributed workforce shift
- Founder Experience: Chaudhry’s previous exits gave him credibility and vision
$10,000 invested at IPO would be worth $184,375 today.
6. CrowdStrike: +1,327% (George Kurtz – Founder)
IPO Date: June 2019 | IPO Price: $34 | Current: $485
George Kurtz had already built and sold a cybersecurity company (Foundstone to McAfee) when he founded CrowdStrike. His experience taught him that traditional antivirus was dead—the future belonged to cloud-native, AI-powered endpoint protection.
Despite going public right before market volatility, CrowdStrike’s founder-led vision of cybersecurity has proven remarkably resilient, reaching new all-time highs in 2025.
What Made It Different:
- AI-First Approach: Used machine learning when others relied on signature-based detection
- Cloud-Native Platform: Built for the cloud era from day one
- Incident Response: Combined prevention with expert threat hunting services
- Founder Credibility: Kurtz’s previous exit validated his cybersecurity expertise
$10,000 invested at IPO would be worth $142,647 today.
7. Veeva Systems: +1,311% (Peter Gassner – Founder)
IPO Date: October 2013 | IPO Price: $20 | Current: $282
Peter Gassner proves that boring can be beautiful. Veeva focuses exclusively on life sciences—not the sexiest market—but Gassner’s deep industry expertise and technical background created an unassailable moat in pharmaceutical software.
By staying laser-focused on one vertical and building incredibly deep domain expertise, Veeva achieved something rare: sustained 20%+ growth for over a decade as a public company.
What Made It Work:
- Vertical Focus: Went deep in life sciences rather than broad across industries
- Industry Expertise: Gassner’s background gave him unique insights into pharma needs
- Salesforce Platform: Built on proven infrastructure, focused on industry-specific value
- Regulatory Advantage: Deep compliance knowledge created massive switching costs
$10,000 invested at IPO would be worth $141,080 today.
8. Atlassian: +924% (Mike Cannon-Brookes – Founder)
IPO Date: December 2015 | IPO Price: $21 | Current: $215
Mike Cannon-Brookes and Scott Farquhar built Atlassian with a contrarian philosophy: focus on developers first, grow through product excellence rather than sales teams, and stay far away from traditional enterprise sales tactics.
Their developer-first approach with tools like Jira and Confluence created sticky, viral adoption within engineering teams that eventually spread throughout entire enterprises.
What Made It Different:
- Developer-First: Built tools that developers actually wanted to use
- Bottom-Up Adoption: Let great products sell themselves rather than top-down enterprise sales
- Platform Ecosystem: Created a marketplace for third-party apps and integrations
- Global Vision: Built a remote-first company before it was fashionable
$10,000 invested at IPO would be worth $102,400 today.
9. Splunk: +824% (Non-Founder at IPO)
IPO Date: April 2012 | IPO Price: $17 | Final Price: $157 (acquired)
Splunk represents both massive success and the ultimate exit. The machine data platform created an entirely new category of software, helping enterprises make sense of the exponential growth in log files and operational data.
While the founders had stepped back by IPO time, Splunk’s category-creating vision and execution delivered strong returns before Cisco acquired the company in 2024 for $28 billion.
$10,000 invested at IPO was worth $92,353 at acquisition.
10. Workday: +746% (Aneel Bhusri – Founder)
IPO Date: October 2012 | IPO Price: $28 | Current: $237
Aneel Bhusri and Dave Duffield (founder of PeopleSoft) created Workday to bring HR and finance applications into the cloud era. Their experience having built and sold PeopleSoft gave them unique insights into what enterprises needed next.
Workday proved that even traditional enterprise applications like HR could be reimagined for the cloud, creating a new generation of business software.
What Made It Successful:
- Founder Experience: Bhusri and Duffield had already built and sold PeopleSoft
- Cloud-First Vision: Reimagined HR and finance for the cloud era when others were still on-premise
- User Experience: Made enterprise software that people actually enjoyed using
- Integration Platform: Built a complete suite rather than point solutions
$10,000 invested at IPO would be worth $84,600 today.
And Oracle Is … Just Nuts
🚀 Oracle: +458,570% (Larry Ellison – Founder)
Larry Ellison’s Oracle deserves special recognition. Going public in 1986 at $15 per share (split-adjusted to $0.046 after 10 stock splits), Oracle has delivered returns that dwarf everything else on this list. A $10,000 investment in Oracle at IPO would be worth $45.86 million today.
Ellison’s 39-year wealth creation story represents one of the greatest fortunes ever built in software, proving that founder vision combined with relentless execution can create generational wealth on an almost incomprehensible scale.
The Common Threads: What Made These Founders Different
Category Creation Over Competition
Eight out of ten of our top performers created entirely new categories: cloud software (Salesforce), e-commerce platforms (Shopify), inbound marketing (HubSpot), cloud security (CrowdStrike, Zscaler), vertical clouds (Veeva), and developer-first collaboration (Atlassian). Being first in a new category beats being best in an old one.
Platform Thinking
Notice the pattern: Salesforce (AppExchange), Shopify (app store), HubSpot (integrations), CrowdStrike (security platform), Atlassian (marketplace). They all built ecosystems, not just products, creating network effects and switching costs.
Technical Depth + Market Vision
Every founder combined deep technical understanding with expansive market vision. They weren’t just building features—they were reimagining entire categories of software.
Long-Term Commitment
These founders didn’t flip their companies or step aside. They committed to decade-plus journeys, weathering downturns and staying focused on long-term value creation.
User/Developer Obsession
Whether through APIs, ease of use, or superior user experience, these founders prioritized the people actually using their software over traditional procurement processes.
The Portfolio That Changed Everything
A simple equal-weight investment of $10,000 across all 10 companies would have resulted in:
- Total Investment: $100,000
- Current Value: Approximately $2.4 million
- Total Return: +2,300%
But the concentration in the top performers tells the real story. Just the top 3 companies (Salesforce, Shopify, ServiceNow) turned $30,000 into over $2.1 million.
What This Means for Today’s Founders
These returns prove that B2B founder CEOs haven’t just created successful companies—they’ve created some of the greatest wealth creation vehicles in public market history.
The Patterns That Created 9,000%+ Returns:
- Category Creation: Salesforce created cloud software, Shopify democratized e-commerce
- Platform Thinking: Built ecosystems, not just products
- Long-Term Vision: Stayed CEO for decades, not quarters
- Technical Foundation: Deep understanding of what they were building
- Market Timing: Caught major technology transitions early
The Lesson for Today’s B2B Founders
The data shows that founder leadership + B2B software + long-term thinking can create returns that approach the mathematically impossible. Don’t give up the CEO chair. The greatest wealth creation stories in software belong to founders who stayed the course.
The bar is now 9,000%+. Who’s next?
All returns calculated using split-adjusted IPO prices and current June 2025 trading levels. Past performance does not guarantee future results. Data compiled by SaaStr.ai.
