Make Your Company Data AI‑Ready Today
No matter what kind of company you are...start making your internal company data legible to AI. Today. As a founder, you are essentially building two versions of your company: the one humans work in and the digital twin that AI agents navigate to do the heavy lifting for you.
Ramp’s Playbook Helps Pre‑2024 Companies AI‑Pill Their Org
I've noticed "most" companies founded in 2022 are quite different in how they organize/build than the ones founded in 2024. If you were founded pre-2024, Ramp built a really thoughtful playbook on how to get your whole org ai pilled.
Getting Lost in Claude AI Distracts From Work
Anyone else "falling" behind their day-job duties b/c they have "fallen" deep down the Cluade rabbit hole?
Relentless Hiring Standards Preserve Culture and Excellence
🚨🚨NEW EPISODE DROP Sally Kornbluth, President of MIT🚨🚨 "If you take a lick of the lollipop of mediocrity, you will suck forever." I love this. She was talking about how MIT sustains excellence after 150+ years. And it applies to founders and CEOs...
Near‑perfect Agents Demand Exponentially More Development Time
Building a 90% complete agent: x time Building a 99% complete agent: 10x time Building a 100% complete agent: 100x time Does this sound right or am I doing something wrong?
Start in Silicon Valley, Scale in Secondary Talent Hubs
I think Silicon Valley is a gr8 place to start a company, but a tricky place to scale a company. The talent is very expensive and hard to keep around when the inevitable bumps come. I'd pick a 2nd city...
Jack Dorsey Plans Near‑Zero Hierarchy, 6,000 Direct
So @jack wants ~6,000 employees reporting directly to him in the new version of the company. Layers between CEO and any employee in the company: ~5 today → 2-3 this year → basically zero https://t.co/nWtEzM6td6
Future Workplaces Will Become Flatter, Faster,
What is going to change: 1. Org structures (flat to round) 2. Compensation structures (steeper) 3. Hiring pace (slower) 4. Hiring profile (experience to taste) 5. Decision makers (the system) 6. Pace (faster) 7. Planning cycles (short) 8. Focus (less) 9. Paranoia (up) 10. AI leverage (indiv to org) Tweet below...
Continuous Reinvention Is Essential for Future Relevance
"I can't imagine doing anything bigger than rebuilding our company as an intelligence, or more correct, given where everything is trending. It feels like I have to constantly build .... and constantly learn from whatever we're putting out there ......
Middle Managers Struggle as Companies Embrace Dorsey‑Mode Flatness
The folks in the middle of the org chart whose main function is "carrying context" are in a tricky spot in world where folks start adapting something appraoching "Dorsey mode" a la Block, Coinbase, Ramp, etc. Good article by @buccocapital on...
Time for a New AI‑Age Management Playbook
"All of us read and follow Andy Grove's 'High Output Management.' Its time for a new playbook built for managing in the ai age." - @wadefoster, Zapier #DorseyMode
Treat Every Interaction as a Mentor, Not Just One
Best mindset shift I’ve heard: Stop hunting for one mentor. Make every single encounter your mentor. https://t.co/odrbPVa0uF
Reprogramming Mindsets: The Core Trait for Founders, Operators, Hires
The single most important quality in a founder, a strong operator, and a hire: the ability to reprogram their mind and assumptions. https://t.co/q2Md2PWkj6
Turn Everyday Tools Into AI Insights for 3x Company Clarity
A lot of founders have pinged me to ask what steps they would need to take to pull of what @jack has done restructuring @blocks this way. He answers it spot on 👇 "look at all the tools you're using. Look...
AI Turns Companies Into Self‑Intelligent Organizations
NEW EPISODE: @jack & @roelofbotha unpack @blocks 40% staff cut and rebuilding the entire company as a mini-AGI. This isn’t “use AI to make people more productive.” It’s making the company itself the intelligence. If you’re a founder or operator wondering what...
Running Companies in the AI Era: Insights with Jack
Tomorrow on Long Strange Trip: I get to talk to @jack on how to run companies in the AI era, joined by @roelofbotha https://t.co/p8eKRUDYWA
Blueprint for Building AI‑Native Companies in 2026
I got a chance to interview Jack Dorsey for the Long Strange Trip pod about his new article (in comments) on how to build a modern ai native company in 2026. I took some of his ideas and mixed them with...
AI Threatens Middle Managers' Dilbert‑Style Survival Tactics
In the AI era, the middle manager is in trouble. @ouraring CEO Tom talks about the "Dilbert problem": a middle manager whose only ambition is to make their own life manageable. https://t.co/DADwDcfqIP
AI Proficiency Will Split Employees Across All Levels
I think we’ll see more of this as the “deeply ai powered” employees separate from the “barely ai powered” employees regardless of level. https://t.co/FyDLvokYaf
Massachusetts Boosts Startup Scaling with New Initiatives
A pretty rough article came out today re the Massachusetts economy (see in reply). While I agree with a lot of the problems, a lot of the builders in Massachusetts are working very hard to make it not just...
From Founder to CEO: Walsh’s Playbook for Scaling
What Jack Dorsey learned from Bill Walsh (49er’s legend) about going from startup founder to scaleup ceo.
Earn Your Stripes Monthly: Subscription Drives Hardware Success
The power of a subscription model is that you gotta earn your stripes with your customers every month. @ouraring CEO, Tom Hale, on what it takes to be the most competitive hardware company in the world https://t.co/E8lqpCZuPZ
Cultural Clash Fuels Innovation, Says Oura CEO
🚨 NEW EPISODE DROP 🚨 CEO of Oura Ring You can't force two cultures into one monoculture 🇫🇮 +🇺🇸 Tom Hale has half his @ouraring team in Finland, half in the US. Two very different worlds. His take: let them stay different. The...
AI‑First Refounding Shapes Tomorrow’s Decacorn Leaders
Refounding a company in this era, from AI first principles, when you’re not the original founder is the story that will define this next generation of decacorns 🔥 The future belongs to the bold. Buckle up.
Design the Process, Deliver the Outcome—Team Synergy
"Your job is process design, my job is outcome delivery" This might be my favorite single clip of the podcast to date: https://t.co/4yuIDESVAT
Entrepreneurship: Painful, Lonely, Not for the Cool‑Factor Dreamers
Most successful entrepreneurs you talk to, if they're being honest, would say something along the lines of, "If I knew everything I know now, I would not have done it." The kind of people who decide they want to be founders...
Choose Uniqueness Over Repetition in Podcast Interviews
Dear listeners of my Long Strange Trip pod, Sometimes I have folks on that doing the pod circuit. Should I (1) assume my ceo deep dive is unique and not worry about it OR (2) not spend time filming folks...
Great Customer Service Never Goes Out of Style
Chewy case at my class today. Great customer service will never go out of fashion. https://t.co/snpd1g5zpl
Brand Power and AEO Replace Dead Referral Channels
Referrals are dead. Google isn't sending many visitors via blue links and social networks are walled gardens. What does this mean for your startup? 1. Brands matter more than ever -- you're larger competitors have advantage here. ...
Compress Sales Leadership Phases to Accelerate Scaleup Growth
I see 3 phases of sales leadership hires in scaleups: 1st - Get first customers and get first sales reps. 2nd - Figure out the process to get customers and sales reps. 3rd - Scale the process to get customers and sales reps. You...
Great Founders Avoid Over‑deferring to Senior Hires
New episode of Long Strange Trip with @bhorowitz of @a16z is now live. The first time I pitched Ben for @HubSpot, he passed on us. It stung. So naturally, it’s the first thing I brought up with him in this convo. He’s...
Klaviyo Founders Pledge $6M to Keep Boston Entrepreneurs Local
Klaviyo cofounders Ed Hallen and Andrew Bialecki are donating $6 mil to MIT aimed at keeping more entrepreneurs in the Boston area instead of decamping to California. This is one of several great initiatives designed to make Boston a fertile...
Prep Early, Focus Collaboration, Bring Hard Problems
First board meeting? Tips: 1. Send the board deck (or memo) 48 hours before. 2. Assume board members have read it, so you don't have go through everything they've already processed. 3. Bring your hardest problems and debates explicitly...
ServiceNow’s $100B Valuation Highlights Massive ITSM Market
Even after the SaaS dip, ServiceNow's market cap is north of $100mil "largely" for internal help desk. I've always been surprised how big the ITSM market is. Am I alone on that one?
Boardrooms Now Fear AI Rivals, Not Just Tech Giants
Every board room. 2015: What are we going to do if Microsoft or Google come into our space? 2025: What are we going to do if OpenAI or Anthropic come into our space?
Match Platforms, Prioritize Distribution Over Price in M&A
I recently sat down with @PaloAltoNtwks CEO @nikesharora on Long Strange Trip, and we spent a lot of time talking about M&A – from the buyer’s side. I mulled on that for awhile and came up with my (hopefully non-obvious)...
HubSpot Alumni Land Top Roles at Rising Companies
I'm happy to see some of the HubSpot alumni joining some very high potential companies, particularly: 1. Dannie Herzberg leaving Sequoia to be President of Baseten 2. Ryan Meadows leaving Klaviyo to be CRO at Lovable 3. Katie Burke getting...
AI Startups Need Blueprint for Perfect Pilot Conversions
The long pole in the tent for so many of these AI startups is getting great at selling and converting pilots. Someone should create some content on doing the "perfect pilot" for all of them to use.
Founder-CEO Traits that Attract Money, Talent, Customers
Here's the criteria I use to evaluate founder-CEOs: First principles Lovable Obsessive Chip on shoulder Knowledgable I do each of these on a scale of 1 to 10 after every pitch. Founders who rank high have money, talent, and customers "FLOCK" to them.
SaaS Survives; only AI‑adopters Stay Alive
I don't think SaaS is dead. I think SaaS companies that don't lean hard into AI are dead.
Building Great Products Is Hard: Bloat, Maintenance, Integration
@jasonlk Taste is hard (hello feature bloat) Maintaining is hard Legit integrations are hard
Comparing 1999 to Today: Key Differences Uncovered
Because I'm old and was around in 1999, people ask me the differences. Here's what I've got. What am I missing? https://t.co/BBkuxy3iXw
Customer Obsession Fuels Intuit’s Relentless Innovation
Everything I learned from interviewing Intuit's CEO. https://t.co/mPBJsX4VXB
Sasan’s Playbook: Scaling Partners, SMBs, and Culture
Sasan, the CEO of Intuit grew their market cap from $50billion to $180billion. Learnings on: 1. How to scale a 2nd channel w partners (90% of rev's) 2. Scaling the sh-t out of SMB 3. The downside of analytics in product...
Scaling Intuit: Lessons From a Non‑Founder CEO
My new episode of Long Strange Trip just dropped with Sasan Goodarzi , the brilliant CEO of Intuit who took it from $50billion to $180billion. Listen if you want to learn about: 1. What non-founder scaleup CEOs have in common....
Scaling Fast: Parker Conrad Keeps 4,000‑Person Rippling Agile
ALL of the CEOs I interviewed for Long Strange Trip complain about how their companies slow down and get less sh_t done as they scale. I felt this at HubSpot too back in the day. Learn how @Parkerconrad moves Rippling 4,000...
Scaleup Success: Key Lessons From Conrad and Halligan
Parker Conrad (Rippling) + Brian Halligan CEO (HubSpot) combined scaleup CEO Lessons. https://t.co/fsC08olygw
Key Lessons From Parker Conrad on Scaling Teams
Here MY TAKEAWAYS on the my interview with Parker Conrad of Rippling. There's a bunch of nuggets in here between what I learned at HubSpot and Parker learned at Rippling. Full interview in the comments.
From Fired to $17B: Turning Failure Into Fuel
“Startups are somewhere between completely impossible and very, very, very, very hard.” That's @parkerconrad, CEO of @Rippling, on the first episode of Long Strange Trip. Parker's got one hell of a story. Violently fired by David Sacks from Zenefits. Character assassinated in...
Will AI Agent Apps Match 80% SaaS Margins?
25 years ago, @Benioff set a terrific precedent for the SaaS industry w their 80% gross margins. I wonder where that will settle out at for the ai native agent/app companies. Guesses?