From Survival to Significance: The 5 Stages of Success In Any Area of Your Life

You might not know my story yet, but... I’ve come a long, long way. I wasn’t born into success. I was a very troubled teenager, big-time. In and out of jail a few times. Rehab too. But I pulled myself out from some bad places, took responsibility for my life, taught myself to code, and started building software companies. I really struggled, until at 28 a US firm acquired my business and I found a real taste of success.

5 Steps to Having Your Newest Sales Rep Closing Deals Better & Faster

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

Editor vs. Author: 5 Strategic Leadership Skills Your Startup Needs For The Long Game

A few years back I had the privilege of hanging out with Jack Dorsey, the founder of Twitter and Square, while we were on a speaking tour in Canada. This guy is a machine. He’s running 2 x Billion dollar businesses with a combined employee count of over 5000… at the same time. So I figured a guy with a net worth of $5.7 Billion (yes… billion) might know a thing or two about leadership for scaling businesses. ...I was

[Escape Velocity] – Episode 8 – Nathan Barry at ConvertKit

Imagine this scenario... You’ve launched a great SaaS product and things are starting to look up… GREAT! Now you are doing marketing, sales, dealing with clients, upgrading the product, doing everything you can to stack up your MRR. The more you grow, the more you have to delegate and rely on your team members. There comes a point where you have to decide what kind of leader you are going to be. And let me tell you, that is one

[Escape Velocity] – Episode 7 – Darren Chait at Hugo

How do you deal with having a powerful new idea that inspires you to change the direction of your business? Many times on the journey  you will find yourself shifting priorities and jumping on new opportunities. That one meeting, conversation or feedback from a client makes you realize that there is a niche to be filled and you can take things to a whole new next level. Being flexible and creative is awesome, but it is not easy to get

7 Intuitive Ways to Think About Offering Employee Equity in Your SaaS Company

Imagine the following… You’re growing fast and you need to hire a new biz dev guy.  He’s convinced that he's going to add a lot of value to your company, and asked for 1% of your startup, so you give it to him. After a few months, you pivot the business and he’s no longer needed (plus he didn’t actually do anything while he was around). Next thing you know, you are just about to raise the first round of

[Escape Velocity] – Episode 5 – David Hauser at Grasshopper

What's the first thing you need to do when starting a business? (A lot of entrepreneurs get this part wrong.)  Now, I know... everything starts with "there's a problem that needs solving and I can solve it."  Then, if things go right, you reach a point where you have 25+ people... and all of a sudden, they're making decisions against the values your business stands behind - the core of the company.  Meaning, the first thing you should set in

Creating a Sticky Product: Five Phases of a World Class Product Development Process

A few weeks ago, I hosted a meetup with my SaaS Academy clients in Boston (including a private sit down with the Hubspot product team). Most of my clients are non-technical founders who noticed a gap in the marketplace and went all in to capitalize on the opportunity. And while product management tends to be a major blind spot for most non-technical founders, this group walked away armed with the best practices from some of the world’s top SaaS companies