Thoughts on doing a startup (6 months in)


When I left my previous employer after 21 years, I felt conflicted.  On one hand, I had found a group of investors that were willing to invest in me despite the fact that products were still a long ways off.  It was gratifying to know they were investing in the person as much as the ideas.  My already unhealthily-over-sized ego was at an all time high.  In addition, the CEO understood why I wanted to try the startup life, and was supportive — it felt good that I had the option to leave on great terms.

On the other hand, the company was entering an interesting period in its trajectory with a brand new platform driving it forward.  As CTO, I had what was unquestionably one of the best jobs in the company, surrounded by super-talented people, with nearly boundless resources.  This was 21 years of my life — it kind of felt like leaving unfinished business behind.  However, I had hit the glass ceiling,  there was no where else to go, no new challenge to strive for.  The CEO was very frank in telling me he just didn’t believe I had the skills to lead a large team or run a division.  I didn’t agree (surprise).  So I could either stay, and be very comfortable for 42 more years, or I could take a shot at doing my own thing.  Driven partly by ego and partly by adrenaline, I took the plunge.

Everyone says doing a startup alone is hard – and they’re right

So I charged ahead, and founded Electric Plum, LLC.  I was armed with a lot of good ideas, technical experience, plenty of funding and a few years of runway ahead.  It was (and is) invigorating and exciting.  The thing I underestimated was how much I had thrived on interacting with other like-minded folks on a daily basis.  I came to realize just how catalytic that force is in the creative process for me.  As I drove ahead on the technology platform front, the satisfaction was muted, and doubt crept in.  I spent almost every night in those early days staring at the ceiling, not getting a lot of sleep.   Why did I leave?  What if it fails?  I still have three more kids to put through college!  Was my selfishness going to affect my family?  I knew these were all common emotions one goes through in that situation, but I didn’t realize just how debilitating they could be.  A draft email to the CEO groveling (begging) for him to take me back sat in my outbox, beckoning me to hit send daily.

Turning point

A few months in, I sent an update to my investors on where we were at with various product ideas.  I had also been getting an increasing number of offers to do consulting and contract work, and I was not sure what to do.  I explained to my investors that the work wasn’t “strategic” and asked what they thought.  One of the investors sent a pretty insightful note.  This particular investor played a key role in building a major company, and I respect him greatly.  I’m paraphrasing a bit, but basically he said, “Sean” (yes he spelled my name wrong – maybe to get my attention!) early on with our company we were charging ahead, building a product for our target market when an opportunity came to build something for a hardware store.  We jumped at the opportunity.  We knew we could do it, maybe on our own time, and we also knew it would generate revenue.  Revenue that would keep the company moving forward.  I think anything that can extend the life of the Plum should be considered.”  Of course he also made a quip that it would also extend the time before I came knocking asking for more money.  In his inimitable way  he pointed me in the right direction.  That was the turning point.  As I began meeting with people, exploring these opportunities that important catalyst was back.  Even though the opportunities were not specifically related to what I wanted to build at Electric Plum, they sparked me creatively (and how many startups actually end up doing exactly what they set out to do anyway?).  The doubt faded, momentum was the antidote.  I recognized that something as simple as a good lunch meeting had immensely positive effects.

The next 6 months

There is no super amazing rags to riches conclusion to this post, but I can say that I no longer stare at the ceiling every night, and I have deleted the “Please take me back!” email that festered in my outbox.  Things are moving forward. Leveraging some existing platform technology, I carved out a piece and  we released our first product.   It has turned out to be a bit of a phenomenon, downloaded by hundreds of developers every day, and used by thousands daily.  It was small enough where I felt releasing it free to position the Plum strategically was a better strategy than charging for it.  That seems to be paying off as it is opening all kinds of doors for the company.  It didn’t hurt when one of Microsoft’s top technical evangelists tweeted about it leading to thousands of downloads in just a few hours.

Six months in, and I feel like I have learned 10 years worth of stuff about doing this and about myself.  We’re still a long way from super success, but I can at least taste it, and that is a pretty motivating force.

Next time I’ll post something less melodramatic and about technology!



Hi folks.  As we grow Electric Plum, I have been yearning to have a space where I can discuss some topics in more than 140 characters.  So I’d like to officially welcome you to this space.  I expect we’ll post a healthy combination of Electric Plum-specific information, general tech industry content, and super geeky stuff.

In addition, you can follow me on twitter @LiquidSullivan.

Thanks for visiting.

Shaun Sullivan
Electric Plum, LLC