Why I left HubSpot to do nuCloud full-time

Why I left HubSpot to do nuCloud full-time

I.eduGuru and nuCloud blogs also.  If you look at the timeline you will see that my last blog post here was July 28th, 2011!  I promise I’m going to fix that.

One of the reasons for my lack of blogging was I spent the last five months at HubSpot learning sales.  I say learning sales instead of “doing” sales because it was absolutely a learning experience for me.  The psychology of sales is something that everyone should learn.  Sales is one of those skills, like customer service and people management, that are invaluable no matter what profession you are in.  Sales is also an all-consuming beast that has kept me so focused on it that I haven’t been a good blogger, fiance, son, or friend.

Most of you might not even know that I quit HubSpot about a month ago or that I moved back to South Carolina.  That’s right, I’m no longer a HubSpotter, just a shareholder, but I’m now the full time CEO at nuCloud.  I haven’t been the typical extremely open and transparent Kyle because I wanted to enjoy the holiday break and it is simply taking me a little time to ramp back up again.

So let me tell you the story.

The Lessons Learned and Advice to Other Entrepreneurs

As far back as high school, I knew that one day I wanted to be my own boss and run my own business.  Where some people say they want to be a doctor, a lawyer or whatever else I wanted to be a business owner.  The challenge is getting to the point where you are comfortable enough to take the risk of doing your own thing.

I believe it is something like 75% of restaurants fail in their first year.  That is only one type of business and one you would think the model is fairly straightforward to get right.  It still fails at an incredibly high rate though.  What I’ve learned about business owners and entrepreneurs in general is that they aren’t necessarily smarter or wiser than other people.  They simply have more balls and are not afraid to take a risk.  No matter how you cut it, attempting to forge a new business is a leap of faith.  The reason that certain people attempt it in the first place is because the reward for getting it right can be pretty huge!

Way back in 2008 when I first started nuCloud I remember asking myself if I was ready to try and start a software company.  nuCloud has been a “nights and weekends” passion for over three years now as we have slowly and safely been building the business.  The big debate when I took the job in Boston to go work for HubSpot was “Do I know enough to run my own business, or is there a lot that I need to learn by working at and growing another company first?”

Looking back, moving to Boston and spending the last three years at HubSpot was definitely the right decision.  You don’t know what you don’t know until you have lived through learning it.  When I first started working at HubSpot remotely there were maybe 30 employees and when I moved up in January 2009 there were about 50 people.  By the time I left last month there were over 300 employees.  It was crazy growth and a real experience watching from the inside as the company scaled and tried to keep everything moving forward.  I was given amazing opportunities to learn in my time there.  My jobs included consulting, management, product and sales.  I was definitely better at some than others but to be a CEO/business owner you are one of the few people who needs to be a jack of all trades.  The more you fundamentally understand the various roles people at your company will do the better you will be able to support them and manage them properly.  For this reason I really believe the idea behind the show Undercover Boss is brilliant!

My words of wisdom to anyone else thinking about starting their own business.

  • Always be learning
  • Be fearless and not afraid of failure or you will never make the jump and always wonder what if
  • Be willing to put yourself in an awkward position if you think there is something to learn from it
  • Build an incredible network of friends and family for support

When To Move, Not If To Move Back

By the beginning of December I was to the point where I felt like I had learned a good bit about sales but will be the first to admit that I wasn’t a great salesperson yet.  The truth is I also learned that my integrity would never have allowed me to be an A+ sales person because there were certain steps my code of ethics will never allow me to take.  No matter how you look at it sales is a dirty business, and you have to be willing to do certain things and sleep with those actions to truly be an overachiever.  The crazy, for better or worse, thing about it is that the world doesn’t move without sales.

I had learned everything that I felt I needed to learn from HubSpot.  Heather and I are getting married at the end of April so that is just around the corner and we will want to be closer to family.  My nephew is two years old and beginning to speak and I want to be a part of his life.   My father’s brain cancer won’t get any better and every day I’m away is another day that I’ll regret one day if I’m not there.  My best friend Skip is 14, which is old for a dog, and I don’t want him to have to endure another Boston winter.  nuCloud actually had quite a good 2011 and my brother had been working full time on it for five months already.  Deep down inside I’m a country boy who would much rather run around in the woods than tour a big city.  There were so many compelling reasons to go home that it was always a question of when not if.

I asked Heather in early December, “What are we waiting for”?  The decision came pretty quickly for the two of us at that point.

The Big Move

December 16th was my last day at HubSpot and on January 4th we got into the car and moved.  It was the end of an adventure.  Everyone should move far away from home at some point in their life for the experience.  For us three years was enough.

I can’t even tell you how exciting it is to finally be doing my dream job.  It has taken a lot of work and more learning than you can imaginge to get to this point.  Although I’ve been on this path for over a decade I’ve really just begun the journey.  In the beginning I had no idea what the business would do and the amazing idea for nuCloud kind of fell into our laps.  You have to be ready to go on the journey if you want to see where it leads though.

nuCloud has the typical startup/small business problems, but they are all problems that I’m ready to handle.  They are also all MY problems and for a problem solver like myself I wouldn’t want it any other way.  The nuCloud corporate office is setup in my brother’s basement on a couple of folding tables and I love every minute of it!

Who needs an interactive campus map for their website!?  I know this great company that will get you setup with one and really take care of you for a great deal!

Image Credit: Sunrise by CoreBurn


  1. dennis miller
    Jan 17, 2012

    Congratulations, Kyle. Great post, and I totally agree with everything you said. Best of luck with nuCloud. I know you’ll do well.

  2. Chris H
    Jan 17, 2012

    Kyle, keep chasing that dream. It was great getting to work with you during our mutual time at HubSpot.

    Best of luck to you and Heather, nuCloud, Skip, and everyone else.

  3. Tim Jacquet
    Jan 17, 2012

    Great story. I would like to interview you on my blog radio show. Call me at 214-224-0995 or email me you contact info. Thanks!

  4. Tim Jacquet
    Jan 17, 2012

    Great story. I would like to interview you for my blog radio show. Please email me contact info at tjacquet@applecapitalgroup.com

  5. Jen Poole
    Jan 17, 2012

    KJ..you’ll always be one of the greats in my book – I think you’re a very special and captivating person. I’m sorry I didn’t see you and Heather before you went home – life is crazy with work and family. Hope to see you when I come down for work. All my best!

  6. Kyle James
    Jan 18, 2012

    Thanks for the encouragement everyone!

    @Tim – I just followed up with you in an email.

  7. Mike Volpe - CMO @ HubSpot
    Jan 20, 2012

    Best of luck in the new venture and thank you for all of your contributions at HubSpot.

    While sad to see you leave, we’re very happy have you join the group of HubSpot Alumni who have started their own company – we think that is a very good thing for the entrepreneurial community.

    Good luck!

  8. Would love you to come to the next HubSpot Alumni event and present your progress on nuCloud. …I want you to be a big piece of the HubSpot mafia (a la the PayPal mafia).

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