tl;dr: Earlier this week, I launched a new, A.I. focused newsletter on agent.ai.   Why Another Newsletter? I've been digging into A.I. for a while now, and I just wanted a convenient mechanism to share things I've learned in the hopes that it'll help Connect Dots both for me and for you. Also, I've never created a newsletter before, and was curious to learn more about how they work and try out one of the newsletter platforms.  I started on Substack, but ended up moving to Beehiiv -- primarily because Beehiiv has an API and Substack doesn't.  Some day, if this is successful ..read more

The following is a guest post by Arjun Moorthy, founder of The Factual. Arjun and I have known each other for a long time, originally when he was a member of the HubSpot leadership team.  He's one of the smartest people that have come through the halls of HubSpot. -Dharmesh Startups are hard. 90% fail, 10% within the first year itself. If you’re a startup founder you already know these statistics and yet you are irrationally proceeding forward. Bravo! I did the same thing six years ago and having just successfully sold my company I’ve learned a few hard lessons that I’ll share below in th ..read more

The following is based on a blog post I wrote 11 years ago. It markedly improved my life, so I decided to create a v2. You can access this post by visiting SorryMustPass.org.  Greetings, Thanks for reaching out about your startup, project or offer to introduce me to someone awesome.  Sorry, but I must pass.  During the last two years of the pandemic, I've taken stock of my life -- and my schedule, and have decided to make some changes in the hopes of creating more harmony and joy. One of my biggest weaknesses in life is that I too often say yes. I'm passionate about startups. I ..read more

Last weekend, just for fun, I hacked together a simple web application called FirstWord. Not exactly sure how to describe it, but it's kind of a trainer to make you a better Wordle player. It grades your first word guess (hence the name FirstWord). So, it's kind of a "word grader". Wait, what's Wordle you ask? Well, it's all the rage. A simple word game where you have to guess a word in 6 tries, as the game gives you clues about your prior guesses.  In any case, I built the app in a couple of hours on a Saturday, launched it on a Sunday. In the ensuing 7 days, it took off.  Over 200 ..read more

In the early days of HubSpot, I somewhat accidentally ended up discovering a new approach to freemium that wasn't really freemium. Here's a short (1 minute 15 second) video clip on what I found that worked brilliantly for HubSpot and helped us drive spectacular early reach ..read more

I was recently on The Hustle's "My First Million" podcast with Sam Parr and Shaan Puri. I'm a fan of the show, so it was a lot of fun to be on as a guest. One quick apology before we jump in: I try not to be too braggy -- but I balance that with transparency and openness. Sam and Shaan asked me several questions about what it's like to be a billionaire, and I answered them openly and truthfully.  (They did warn me beforehand and gave me the option not to answer). And, The Hustle team decided that having "billionaire" in the title of the episode will attract more viewers -- so here we are ..read more

15 years ago today, on June 9, 2006, HubSpot was “officially” started. I say “officially”, because unofficially, I had been noodling on the idea of HubSpot for a couple of years with my co-founder, Brian Halligan while we were both classmates in grad school. I picked the June 9th date, because that’s the official date that I graduated and was no longer a student. (Brian graduated a year ahead of me, and I was still working on my thesis). I don’t have a lot of photos from the early years, because as it turns out, neither one of us are big “photo people”. But, here’s one of us celebrating HubSpo ..read more

  I’ve decided I’m going to invest $1 million in BitClout the blockchain-based, crypto-currency powered social network that is all the rage (at least within some circles). If you don’t know what BitClout is, I think my earlier post “What’s BitClout?” is a decent overview. OK, back to that million dollar thing. To be clear, I’m not buying shares in BitClout (the company). I have it on really good faith that one can’t really do that, and nobody has done that. Instead of investing in the traditional sense, I’m going to do a combination of the following: Invest in startups/projec ..read more

I’ve been thinking about, talking about and working on culture for at least a decade. (Not counting the 15 years I spent being mostly clueless about culture in my first startup). I've spent hundreds of hours working with the HubSPot team to create the HubSpot Culture Code deck. It has been invaluable for us as we've scaled from a 2 founder startup to a 4,000+ person scale-up with a market cap in excess of $22 billion. Here it is... Of all the lessons and insights learned from all that tinkering, this is my biggest epiphany: Culture is a product and your people are its customers. Said diffe ..read more

First off, just to be clear, I’ve never been a sales person.  I’ve never even played a sales person on TV.  All the points below have been pulled from startup sales teams that I think work pretty well (including the team at CRM software company, HubSpot). Building Startup Sales Teams 1.  Don’t hire sales people too early.  In the early days, the founders should be able to sell (and should be selling). Yes, yes, I know. You're an engineer/designer/whatever. You've never sold anything. Doesn't fit your personality. But here you are. I hate to tell you this, but your life as ..read more