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?
Ideal VC Board Member: Five Essential Traits
If I had my pick of VC’s in my next round, I’d look for a “5 tool board member:” 1. Works at a top tier firm 2. Is a GP 3. Has relevant domain expertise 4. Has been an operator 5. Not an a-hole...
Five CEOs Master Vision, Code, Taste, Sales, Recruiting
What do @btaylor (Sierra), @matistanis (11Labs), @kareem (Clay), @parkerconrad (Rippling), @GabeStengel (Rogo), & @daraladje (Delphi) all have in common? They are 5 tool CEO's: (1) Vision, (2) Code, Taste (3), Sell (4), & Recruit (5). Learn more on this...
Companies Shift Gravity: From Employees to Customers, Acquisition to Delight
I think all companies have two centers of gravity 1. Focused on investors, customers, or employees 2. Focused on acquiring or delighting customers HubSpot moved (1) from employees to customers over time. We moved (2) from acquiring to delighting over...
Old CEO Playbook Broken; New Strategies Unveiled
Ye olde CEO playbook I used in building @HubSpot is broken. From Jensen Huang’s 60 direct reports to the way Elon runs his empire to Brian Chesky’s founder mode – it's a reboot. This new playbook is something I’m very curious...
From Starter to Scaler: Evolving Sales Leadership Stages
In the startup to scaleup journey, I often see 3 phases of sales leaders: Starter - A leader who can hire a few reps and close some deals. High Riz. Closer. Not analytical. Solver - A leader who can figure out the profile of...
Startups Advance in Small Leaps, Not Silver Bullets
Startups are 1 step back, 2 steps forward, 1 step back, 2 steps forward, etc. From the outside, HubSpot might seem like a smooth up-and-to-the-right story. It belies what actually goes on inside. The best way I’d describe HubSpot is two...
Leadership Improves When You Stop Pretending to Know Everything
For a very long time as CEO of HubSpot, I thought I was supposed to have all the answers. Life got easier for everyone (especially me) when I got over that.
Scale Smart: Hire Slow, Promote Internally, Balance Talent
A lot of startups get stuck in the mud between 200 and 2000 employees. Here are my tips: 1. Ye old "hire slow and fire fast" is still true. 2. Push off the director layer as long as you can....
From Seats to Credits: Next Bubble's Lingering Hangover
There was a “seats” hangover after the 2021 bubble There will be a “credits” hangover after the 2025 bubble
Customer Sales Feel Better than Investor Pitches
Selling to customers is so much nicer than selling to investors.
Build Friendships with Competitor CEOs for Founder Success
I always tried to keep a good relationship with the CEOs of HubSpot’s competitors, like Salesforce, Zendesk, Marketo, Eloqua, Mailchimp, etc. It served us well. I recommend founders do the same.
Take Acquisition Offers Seriously—High Valuations Favor Selling
Dear Founders, If you have acquisition interest from a bigger co, take it very seriously. If you don’t sell, that bigger co will buy your competitor or build. Not great for you. Also, valuations are sky high right now,...
SF Tech Firms Adopt New Ideas Far Easier than Others
Getting tech companies in San Francisco to try your new thing is A LOT easier than convincing the other 99% of companies out there.
Hyper-Growth Inevitably Triggers Churn, Then Sustainable Second Act
I predict this cycle for a lot of the hyper-growers: 1. Hyper-growth 2. Massive churn crisis 3. Fix churn crisis 4. Growth 5. 2nd Act
Outcome‑Based Pricing Unlikely to Go Mainstream
I was really excited about the outcome based pricing model à la what Sierra, Fin, etc are doing, but the more I look into it, the more I think it won’t become the norm. Too hard to apply in...
Prioritize Delighted Customers over Hype Growth Curves
Dear Hyper-growth founders, Legendary companies are built on the backs of their delighted customers, not on the backs of their buzz/curves/demos. Don't fall in love with your hockey stick curves...fall in love with your customers. Love, Brian.
Transparent Prep and Dialogue: CEO Board Meeting Essentials
Board meeting tips for CEO's of private companies: 1. Be transparent -- it builds trust. Board members can tell if you are spinning them. Save the sales pitch for the sales prospect. 2. Prep time -- Either send...
