5 Secrets of SERIAL Entrepreneurship

Serial Entrepreneurship Definition: Running 2 or more startups at the same time. Some definitions involve creating startups in succession, but for the purposes of this discussion, let’s limit the term to the simultaneous management of 2 or more startups. 

A number of the startup founders I’ve been helping recently have told me that apart from the current startups they are involved in, they suddenly have an idea for another one. Then they begin telling me about the other idea.

What I’ve consistently said was:

STOP! Concentrate on your first, startup concept first – presumably your best and biggest idea. Anything else is a distraction.

Of course, all this time, I’ve been waiting for someone to say,

Heeeeeey, wait a minute, you’re not practicing what you preach! You’re involved in a number of startups!

Guilty as charged. Serial entrepreneurship is a path you can take a long look at.

Just take heed of the following items:

1) Initial success begets success.

I started my second company, Searchlight, a full 5 years after my first company, STORM, was founded. It was only after STORM’s success that I had the confidence to try forming another firm. And even then, I studied the Searchlight market for almost a year before plunging in. I applied everything I learned from STORM in my experience in Searchlight – starting ultra-lean, having a clear focus, getting good people. In other words, I NEVER would have succeeded in Searchlight and the newer firms had I not initially succeeded with STORM.

I started Searchlight as an experienced entrepreneur – and that made all the difference.

2) You have to accept that the time you spend in one startup is the exact time you rob in the other.

Time is a zero-sum game. Your startups need as much time as it could from you – your full attention. If you have two or more, then it is quite obvious that ALL the startups in question would not be as successful as it would have been had you given it your full attention.

This is a reality I live with. How big could STORM be if I dedicated my full-time and effort to it? Searchlight? Stream Engine? I would never know.

3) If you insist on going serial, it helps greatly to have startups in related fields.

STORM is an HR services firm. The biggest reason I thought about putting up Searchlight is because our own clients were bugging us to do executive search. Like STORM, Searchlight is an HR services firm. So in running the two firms, there is a lot of dovetailing which happens. For example, the target market for both firms are the same. Almost ALL of Searchlight’s initial clients came from the STORM network. The numerous efficiencies created in having related firms mitigate the effects of item no. 2 a bit.

The next firms I was involved with were services firms as well. It is only very recently that I am finding myself involved with products, but even then, these would be technology-related products – an arena I am pretty familiar with.

4) It HAS to be in your DNA

Like with any career decision, you have to look deep within what you really like to do. What I have discovered about myself is that I find it difficult to focus – I need to be involved with different things at the same time. Another thing that I have discovered about myself is that I absolutely love the challenge of the startup process – putting together the RIGHT people with the RIGHT ideas, and then going to war with my team in the trenches. And I guess I like the risk involved – the whole David vs Goliath thing. It’s a bit masochistic, but I do love it, the challenge of it, the excitement of building things.

5) My biggest serial secret is simple – Paolo De la Fuente, Maan Pamintuan, and Gino Caparas

Paolo, Maan, and Gino, help me run STORM, Searchlight, and Stream Engine, respectively. That’s the secret, that’s how I manage to be involved with these startups and have time for my other endeavors, like Juan Great Leap, Bizkitchen, and even more startups.

The secret is finding great people.

Have you guys read Gladwell’s Outliers? Remember his criteria about being “gifted” or being an “expert” in your field? Gladwell challenges the notion that giftedness is genetic, and cites that gifted people simply spend the requisite number of hours honing their craft. 10,000 hours, to be precise. I was just calculating – I’ve spent MORE than 10,000 hours in recruitment. That was a blessing, in retrospect.

I may not have 100% batting average, but this learned skill certainly helps me in being more efficient in finding great people I can build things with. You have to be able to love networking,  building relationships, and envisioning how people would do in specific roles.

The corollary to this secret? Once you FIND a great partner, you have to be very willing to SHARE equity/ownership/control. This might be easier said than done for some people.

The control aspect is pretty tricky. When building a company from the ground up, the experience you garner is that you control everything, precisely because you manage everything. In choosing to be involved with different things however, you HAVE to cede control at some point.