Years ago I attempted to raise money for my first company, Flowtown, with my co-founder Ethan. You know what we did? We cold emailed investors.  We figured “We have a startup, they invest in startups... so surely they want to hear from us”, and hoped our confidence would cut through the noise. It didn’t work. Obviously. They didn’t even bother to reply. So we hunted for advice and came across Naval from AngelList.  Everything he said about fundraising just… clicked.

Health is wealth. It’s a mantra I repeat to myself a dozen times a day anytime my brain wants to slack off on training, or reach for those nachos. It’s also a belief I share with many of my entrepreneurial friends, like David Hauser. I first met David (co-founder GrassHopper.com / Chargify.com and many others) 10 years ago when I cold emailed him for an interview on my blog (recorded with a Flipcam :). Since then we’ve spent a lot

In my career, I’ve hired dozens of salespeople… and I made some big mistakes when I did. Expensive mistakes. In my 20s I hired a guy and paid him $80k salary and all he did was talk about how he was going to close big deals… without ever doing it! For a whole year, this guy promised me the world and delivered absolutely zero value. And I actually paid him for it! Compare that to now: Last week I hired

How do you get invited to spend a week at Richard Branson’s house in Switzerland? Or for guys like Mark Cuban and Travis Kalanick (founder of Uber) to happily invest in your company? Or to get invited to travel to 8 European cities on a private jet? These all happened to me... and I believe it’s a natural result of one thing I did right: Investing In Relationships. I began figuring this out in my mid-twenties and WOW did it

You're a cash-starved startup owner. You go hard after one of your big enterprise clients and they pay for a whole year of your service in advance… Just like this, without any additional questions or arrangements. This is what happened to Vivek Sharma back in the day, when his now $50+ mil ARR company MovableInk was struggling to score its first few corporate clients.  But this idea to ask for a 12-MONTH ADVANCE PAYMENT didn't come out of nowhere. 

Imagine you're 27, you've read 100 business books and just want to move on to the next step in your career… what do you do? Well, when I was 27, I was lucky enough to participate in a 3-year CEO program with my brother. He spent $35K on a coaching program because he was determined to invest in his development as an entrepreneur. And the best part, I got to join him as his +1!

Imagine this… Your SaaS company lands a massive account almost right out of the gates. They start using it. They have feedback… lots of it… almost too much of it. Your team takes it as gospel. Jotting it all down - committing on the spot - holding meetings about those new feature requests -- making plans to push them forward. Before you know it, they’re pretty much writing your entire roadmap for you. “All good” you say. They are, after

My first two companies FAILED hard. Sure, there were many factors at play. But when I take a sec to assess where things really went off the rails, it all came down to this… I had the wrong people on board. And it’s no criticism to them. As a founder (especially in the early stages), you’re ENTIRELY responsible for making sure that you have the right personnel for each position. Where most founders go wrong is that they hire by

I’ll never forget this one employee I had just hired at clarity.fm His first few hours went super smooth. But then at exactly 4:59pm… the guy BOLTED. Laptop packed. Door shut. Making a beeline straight to the front door. My jaw literally dropped. Here was this guy I had just hired… someone who was still getting onboarded to our team, our clients, and our company…

In over 20 years in business, I’ve never met a single founder who hasn’t had to fire at least one employee. While the thought may create knots in your stomach, letting an employee go is actually a super valuable skill with further reaching implications than you might think. Because done wrong, It could crush team morale, compromise data, and even cost you valuable customer accounts. Breaking up isn’t fun… but it’s a skill that as a founder you need to