From the Outside Looking In: John Sheehan & Twilio

From the outside looking in is a dual-purpose interview series with former Minnesota tech entrepreneurs pursuing their startup companies elsewhere.  It’s great to see homegrown talent making it happen — but why not here and what can we learn from their perspectives?

Entrepreneur: John Sheehan

Hometown: Twin Cities, Minnesota

Current Venture: Twilio

Current Location: Broomfield, CO (between Denver & Boulder)

What has been your tech/startup experience in Minnesota?

I lived in the Twin Cities from 1981 until 2010, starting my first IT-related business in 1996 fixing computers, and eventually making web sites (including the first one ever for the City of Princeton). I started my second company in 2000 and went out of business in 2001. I then started RIM Systems in 2005 and I still run it in my spare time and it is self-sufficient.

Why did you leave and what are you currently pursuing?

I moved to Colorado for spousal career support, which happen to coincide with taking a new job at Twilio as a Developer Evangelist working with developers and startups. I’m fortunate enough to have a job that allows me to work remotely from anywhere along with traveling all over the country to meet with customers and attend events.

For RIM Systems, I’m currently in the early stages of building a new consumer web service which I hope to launch in some form later this year

How does your current startup environment perceive Minnesota in terms of tech talent and startups in general?

When people ask me where I moved from and I tell them “the Twin Cities,” their first question is usually, “What’s the startup scene there like?” To which I answer, “It’s young, but growing.” I hope one day it will have its own reputation like San Fran, Boulder, Seattle, Austin, etc. and people won’t even need to ask.

What’s are some of the cultural differences you’ve seen between the two markets (as it relates to early stage tech)?

People who have defected from Minnesota always talk about the cautious nature of people working there. They say that the regional culture favors security and stability over more interesting but risky work situations. I *hated* when people characterized Minnesotans this way before I moved.

But, the truth hurts: it’s true.

So many of the “best” tech jobs in the Twin Cities are in banking/finance/insurance/med tech/bioscience. They’re good jobs without question and they’re safe career choices (well, maybe not banks). It’s easy to explain to your aunt at Christmas that you work in IT at Target.

What is your opinion on the value of incubators/seed capital?

I think they’re immensely important. They give people who otherwise wouldn’t or couldn’t make the leap into a startup the chance to do so with a little bit of a safety net. Some people will argue that if you’re not willing to put your own money on the line for your idea, that it’s not worth doing. Not everything is so cut and dry though. What if you’re just out of college with no money? What if you have a family to support? Availability of seed capital allows you an opportunity to still get off the ground.

If a friend of yours from Minnesota said he/she was starting a tech company in Minnesota and wasn’t interested in moving, what advice would you give them?

There are always reasons not to start, so don’t let your current location or anything else stop you. If you’re determined to succeed, eventually you will. If you won’t relocate, know that you’re going to face some additional challenges. Finding good employees willing to take a risk with you is tough. The tax situation is suboptimal. There are fewer successful entrepreneurs to learn from, companies to partner with, and places to raise money from. All of those things can be overcome but you have to approach it like any other business decision. Can you justify the cost of operating your business in MN?

What would be one thing Minnesota could do, right now, to foster a stronger startup culture and to retain talent?

There isn’t one thing. There’s a chicken and egg problem. You need successful entrepreneurs willing to invest, but there are less successes with so few investors. The current VCs there are not likely to venture outside their comfort zones. I’m not sure how you fix either of those things to get some investment capital flowing, but I do believe that the rest will follow…

Anything else you would like to add?

If you’re sitting around wishing you were in Silicon Valley so you could get started, knock it off, grab your computer and get to work!

Previous posts in this series: Dave Fowler &


  • joesiewert

    Nice interview. I've been following Twilio for awhile now and it's nice to see the tie back to the Twin Cities.