SaaS Titans Flee to OpenAI, Fueling Enterprise Surge
OpenAI just hired ServiceNow 's CMO Colin Fleming. When people who built the SaaS playbook start leaving, pay attention👇 Fleming spent 13 years at Salesforce . 2 years at ServiceNow. Forbes ranked him among the top 10 most influential CMOs last year. In 2026, he just left... and he's not alone. The pattern is hard to ignore: • Slack 's CEO is now OpenAI's CRO • Salesforce leaders have moved to OpenAI • ServiceNow's CCO joined Anthropic last year • Palantir Technologies 's forward-deployed operators left too They are not researchers. They spent careers selling 7-figure complex software to the world's biggest companies. And they all chose to leave. The companies they walked away from tell their own story: > ServiceNow lost 50% its market value in 12 months > Salesforce down 32% in 2026 Meanwhile, OpenAI is at $25B in annualized revenue. Enterprise is already 40% of that and growing. This isn't a research story anymore. It's a sales story. The SaaS players built the playbook for the enterprise. They know the exact buying decisions of that level. When those same people start moving to AI labs instead, it stops being a coincidence. Enterprise budgets follow talent. And the talent has already picked a side. --- Today, I run these 2 private communities that might help you: → SaasRise : for founders scaling from $1M to $100M → GrowthRise: for B2B Sales and Marketing leaders Also see our upcoming AI coding bootcamp (link in comments).
Launch Fast, Target a Niche, and Price Right.
As a first-time SaaS founder, strictly avoid these: - build for everyone instead of someone specific - price at $9/mo out of fear - wait 6 months to launch because it's "not ready" - build for enterprise while bootstrapped -...
A Cruise Panic Attack Revealed My Workaholic Crisis
I almost jumped off a cruise ship during the worst panic attack of my life... That night made me who I am today. It was April 2011... the first-ever Summit Series cruise for entrepreneurs. I had just met my heroes:...
Selective Onboarding and Ultra‑low Pricing Fuel AI Startup’s $165M Growth
Sierra went from $0 to $165M in 26 months 🤯 The playbook behind the AI agent half of Fortune 500 is using👇 Bret Taylor left Salesforce as co-CEO the same week ChatGPT launched. He wanted to build startups again. A...
Accelerate SaaS Development 5‑10× with AI Bootcamp
Registration is now open for the SaasRise AI Coding Bootcamp — June 22 to 25. Anybody can vibe code. But few companies have figured out how to properly roll out agentic engineering across their whole R&D organization with proper QA,...
Evidence‑Driven AI Turned Slack Bot Into $450M Business
2022: Started as a Slack bot. 2026: Hit $450M ARR in 3.5 years. Here's Perplexity 's $20B+ growth story👇 Aravind Srinivas (ex-OpenAI) with Denis Yarats, Johnny Ho, and Andy Konwinski were frustrated by Google's endless list of links. Their vision:...
Choose Joy Now: Build What Truly Inspires You
1998: Started a website design agency at 14. 2002: Started iContact from a dorm room. 2008: Built one of America's fastest-growing software companies. 2010: Overweight. Burnt out. 2011: Had a 10-hour panic attack. 2012: Sold iContact for $169M at 27....
Niche Banking Solution Scales to $250M ARR
2021: Building credit cards for sneaker resellers 2026: Hitting $250M ARR in 5 years Here's Slash 's $1.4B wild growth story👇 Victor Cardenas, a Venezuelan immigrant, dropped out of Stanford at 19. Kevin Bai left Waterloo the same year. They...
AI‑Native Enterprise Spending Soars, Redefining SaaS Landscape
Every week I publish a roundup of the biggest SaaS deals, funding rounds, and insights shaping the industry. This week the signal is impossible to ignore. AI-native enterprise spending grew 94% year over year in Q1 2026. Traditional per-seat SaaS...
Escaping Karoshi: My 20s Overwork Wake‑Up Call
Karoshi is the Japanese term for “death by overwork.” In my 20s, I was headed towards it…
Work Less, Achieve More: My 20‑Hour Week Transformation
Karoshi is the Japanese term for “death by overwork.” In my 20s, I was headed towards it... For most of my early years, I just pushed harder. Emails, decisions, problem-solving... every single day. It felt productive. The result was far...
CEO's ChatGPT Gamble to Dodge $250M Deal Backfires
This $8 billion company's CEO used ChatGPT to escape $250M in an acquisition deal. Here's how it blew up in his face:
CEO's ChatGPT Gamble Costs $250M Acquisition
This $8 billion company's CEO used ChatGPT to escape $250M in an acquisition deal. Here's how it blew up in his face:
CEO’s AI‑driven Takeover Backfires, Court Restores Indie Control
This $8 billion company's CEO used ChatGPT to escape $250M in an acquisition deal. Here's how it blew up in his face: Krafton is the South Korean giant behind PUBG. In 2021, they acquired Unknown Worlds Entertainment... a small indie...
Missing
My goal was $1M in revenue by age 21 but I missed it by 18 days. It still led to a $169M exit. Here's the story👇 At 16, I was making $4k a year building websites in Bradenton, Florida. I...