The Parallel Entrepreneur

I get asked “what are you up to lately?” a lot by other entrepreneurs. It’s one of our universal “safe” conversation topics: unlikely to be controversial; likely to be interesting.

Nowadays, I usually refer to Billfold as my default answer. (And that’s usually followed by an explanation that we’re not a mobile payments company.) But up until this year, my answer was often more complex. I was a parallel entrepreneur: I was actively working on several companies and projects at the same time. And it was a pretty sizable list:

• CEO at Billfold
• Entreprenuer in Residence (EIR) at ATDC
• Co-owner of Ignition Alley
• Design Manager at Army of Bees
• Landlord for my two homes
• Occasional weekend DJ at Nonsense and Death From Below

That doesn’t include my various side projects (both entrepreneurial and personal), or the fact I was engaged this summer and have a wedding to plan. And most of it wasn’t providing me any income. For most entrepreneurs that would be completely insane. And maybe it was insane for me too, but we’ll get to that later.

Operating in Parallel

How does one become a parallel entrepreneur in a way that doesn’t make you want to pull your hair out? It’s a matter of scale: big ideas are bad; small ideas are good. I’ll probably go into this more in another post, but suffice to say, small ideas mean you can be more nimble with your customer discovery and product development. Big ideas take up too much time, especially in the case of a single founder. You want small ideas so you can context switch quickly and efficiently.

This nimble-ness allows one to maintain an on/off cycle with each of their ideas. Most of the time when you consider running a startup, it’s assumed you’ll be “on” all the time. 16 hour days talking with customers, building product, reading bug reports, keeping an eye on competition, etc. But small ideas compress a lot of this in a tighter loop, which is where you can be too nimble. Iterating too fast is a bad thing. You need a statistically significant amount of data to ensure your changes are actually having the impact they appear to be having. For instance, your fancy new landing page launches and you see a double-digit percentage increase in conversions. Excellent! But that traffic is coming mostly from a targeted Google Group you posted in. How is it going to perform when your visitors are coming in from AdWords or other traffic sources? You won’t know until a few days from now when your ad campaigns have brought in enough traffic to measure against. You’ve reached an “off” state. This is the parallel entrepreneur’s time to shine.

While idea #1 is gathering data, it’s the perfect opportunity to start developing idea #2. Or #3. Or #8. As a repertoire of ideas starts to build up, certain efficiencies can be achieved. Customer discovery sessions can apply to multiple ideas at once and the kind of serendipitous discoveries that occur during these sessions can increase. And while certain ideas may be “off” at any point, you are personally “on” almost all the time. Productivity will likely be at its maximum.

Keeping it in Check

And now you’re firing on all cylinders. You’ve got a collection of ideas, each progressing towards a successful result. You’ve learned some cool ways to have ideas #2 and #4 interact, and they may even combine into one product. You learned something cool about idea #1 while doing a discovery session for idea #3. Maybe you’ve even got one or two of these ideas bringing in some money. This is all good stuff.

But it’s not all going to be sunshine and rainbows. If your customer discovery sessions are being done properly, you’re going to shut down some ideas early on that either don’t have a market wanting them or are too infeasible to accomplish. But what about the ideas that limp along and just won’t die? These “zombie” ideas can drain the life out of you. The lean methodology of “fail fast” applies very directly to this kind of situation. You should have a pipeline of ideas ready to go once you have sufficient time to commit to it. And as a result, the loss of an anemic idea shouldn’t be significant, will happen often, and will be an easy decision to make. It can be revitalizing to have something new to work on, and that can be what sustains productivity and enthusiasm.

David Cummings wrote a daily post about running “zombie companies” (which actually inspired this writing) that comes from the perspective of the serial entrepreneur. While his definition of a zombie differs from my own, the core sentiment is the same. Successful parallel entrepreneurship is based around effective time management and constant change. If you’re not able to drop dead weight easily, you may be headed towards crushing failure. Don’t be afraid to move on.

The Path to Success

Where is this all headed? There are a few different directions, all of which depend on your definition of success. No single one is the “right” way to handle the situation, and there can be a myriad of external factors that affect your decision.

The most obvious result is switching back to serial entrepreneurship. One idea becomes the obvious breadwinner and takes on a life of it’s own. It begins to push out the other ideas and demands attention of its own. This may happen after a short stint as a parallel entrepreneur, and it’s OK to throw some things at the wall and see what sticks. Handling the dismissal of your other ideas gracefully can either mean shutting down those projects completely or passing them on to others. I would not recommend keeping them running on the side (which is in line with David’s view), as the distraction is not worth it. You’re switching to running a single company, so other distractions can be disastrous. Either sell them off to someone that will take good care of them, or shut them down completely. If you’re willing to shed weak ideas as a proper parallel entrepreneur, this should be easy.

Another path to success is to simply find the right mix of ideas that generate revenue and are sustainable in the long term. This makes you into a “sweat investor”, whereby you are investing time and effort into these companies to turn a profit, rather than just cash. To be honest, this kind of success is rare. Not because it is infeasible, but because it is often not sufficient for most people. Many entrepreneurs want to hit it big, so the threshold for a “weak” idea may be much more loosely defined. And the ideas that aren’t completely hitting it out of the park are discarded. But that kind of person is probably going to switch back to serial entrepreneurship anyways. But if running a sustainable enterprise among a portfolio of companies is sufficient for you, more power to you.

Lastly, you may find success in becoming an “idea factory” of sorts. That is, you often germinate simple ideas into larger companies and then sell them off when they reach a sufficient enough maturity to run on their own. I have seen a few individuals obtain this kind of success and it can be quite fulfilling. It does require a special kind of person that’s willing to separate out emotional attachment to their ideas for the sake of selling them off to others. One of the most common groups that unknowingly does this on a regular basis are small development shops. Particularly the ones that go beyond just simply being coding warehouses and work with their clients to ensure they’re building sustainable businesses. There are also some of my friends that contract specifically for the development of MVPs. Despite working at the very early stages of these companies, they have seen good success in moving from idea to idea very rapidly.

Why I Switched

But as I stated before, I was a parallel entrepreneur. For me, this path was interesting, engaging, and even rewarding at times. However, it ultimately was not sustainable for me. I took the path to success of switching back to serial entrepreneurship. I ended my time at ATDC in October. Ignition Alley will likely be going through some changes soon. I let my colleagues at Army of Bees take over my role there. I had my roommates move out of one of my houses and I’m planning on selling the other one soon. I simplified everything and moved off the parallel lifestyle. It’s worked out well for me and things are far less stressful in my life now.

Nonetheless, my own experiences aren’t a map for others. Take your own path however you see fit. Maybe it’s parallel, maybe it’s serial, maybe it’s something else entirely. I only know what has worked out for me so far. Perhaps it will change again in the future. I’m still figuring it all out (if one can even “figure out” life). I’ll let you know how it goes.