• How Much Paternity Leave to Take as a Founder? My wife & I are expecting our first—a girl—in under 2 weeks!!! Figuring out how much paternity leave to take as a founder of a fast-growing startup has been challenging for me, and I wanted to share my thought process in case it's helpful to you.
  • Boston Vs. NYC, 20 Months Later An update from Dan Primack's excellent 2014 post on how Boston is doing compared to NYC.
  • Don't Read Too Much Into Emails I believe strongly in not reading things like tone & emotion into email, and I also believe that if you avoid reading too much “between the lines” in emails you will be significantly more effective in life in general (because, hint hint, this applies to more than email).
  • Inside the Boston Tech Re-awakening: A Founder's View Boston's tech star has fallen, overshadowed not just by SF, but also by NY, SoCal, and even Austin. We're last generation's tech hub. The magic of the DECs and Lotuses (both exited before some of our employees were born...) and the other companies on the 128 beltway is over. You have to leave Boston and move to SF to create a great company. After all, Facebook is worth more than all tech founded in Boston since 2000! That, yeah, maybe we have biotech and some robots but that's it. Bullshit. By any measure Boston is still a top-tier tech hub. I believe we're experiencing a new renaissance, and the future in Boston tech looks brighter than ever.
  • Why You Need TSA Precheck The time it will take you to read this? Less than I spend in security for any flight in America.
  • How to Demo Your SaaS Product I love giving demos. I originally wrote this guide on how to give a strong product demo to help scale up our sales team, and I'm sharing a trimmed down version here to help the next batch of SaaS startups get up and running faster.
  • Retailers: Stop Chasing Shiny Technologies and Focus on Products & Experience Technology has become the preoccupation of a sagging retail sector, evidenced by the National Retail Federation’s Big Show last month in New York. But focusing on tech trends is the wrong thing to do to succeed in today's retail environment.
  • WHY to Say No More Often Saying no is like dieting; we all want to do it, but few pull it off. Through careful self-examination, I've found powerful reasons to say no that motivate me to NO all the time, and I'd like to share them with you all!
  • Heroism Doesn't Scale - Some Advice on Effective Delegation When you take on too much, your work suffers, and your life suffers. This post describes some ways to delegate things you're working on - up, down, laterally, and out - to enable you to be both more successful and more happy at the same time.
  • Resilience, Not Adversity, is What Makes an Entrepreneur There's an unhealthy belief in the startup world that adversity makes for a great entrepreneur. I don't agree with this belief. Instead, I think it's the positive things - the love and support and mentorship - in one's life that are far more important in making one successful.
  • "Family Friendly" Only Starts With Maternity/Paternity Leave, It Doesn't End There I work with a lot of parents (and have one on the way myself!), and from the outside looking in, building a family is controlled chaos. Every day is Anything-Can-Happen Day. Companies need to recognize this. Life doesn't just return to normal after maternity/paternity leave; the challenge has only just begun. A truly family-friendly environment has to be flexible enough to work with the every day emergencies that happen for decades.
  • Forget Programmatic Commerce; Assortment is Still King There are many ways for retailers to differentiate based on assortment which are really interesting, and I want to explore a few here.
  • Doctor Wife, Startup Husband: Making it Work This post is dedicated to all those founders out there hustling to make it work without sacrificing the rest of their lives to do so. I never had the luxury of going all-in, because when I co-founded Salsify I was married to a Doctor in Residency in the Harvard system (yes, I'm bragging, because she's ridiculously impressive), had a mortgage, and generally had more “life baggage” than 22 year-olds have.
  • Having Success with Code Bootcamps: A Guide for Employees and Bootcamp Grads We've created a program that we're quite proud of to hire, train, and grow bootcamp graduates, and want to share it with other startups to help us all grow the next generation of programmers and entrepreneurs.