Thursday, February 25, 2010

CTO Founders / Cofounders

I just got done reading a post by Roger Ehrenberg Advice for CTO Founders: Don't Let Business Kill the Business where he suggests that CTO Founders should not move too early in finding a business cofounder:

Too often, however, I have found CTO / Founders paired with business people who not only don't add value, but frequently detract from the value of the business. And from my perspective as an engaged seed stage venture investor, this makes them unfundable. This is not only sad but incredibly frustrating, because it is so easy to see how a great technology can be developed and commercialized if only - if only the CTO hadn't been impulsive and insecure and brought on a business partner too early in the game.

So why do inexperienced (as entrepreneurs), ultra-skilled CTOs fall into the trap of engaging a business partner too early? Fear? Lack of confidence? Camaraderie? Perhaps all of the above.

Knowing a lot of CTO founders, I can tell you that Roger is fairly accurate in his assessment of the desire of CTOs to find the right cofounder to be the business side.  And it’s not just inexperienced CTOs.  And I would add to his list that part of it might be time available to help product definition, pursue market opportunities, early sales, raise funds, etc.

Mark Suster has similar advice in Hiring at a Startup? Know Thy Weaknesses is:

I recommend that you start a company by yourself and own 100% of it.  Once it’s set up I recommend bringing in a co-founder and giving them 10-30% of the company depending upon when you bring them in.  I advocate treating them like a co-founder in every way except when they join and how much equity they get.

Mark Suster defines founder vs. cofounder a bit more in Most Common Early Start-up Mistakes.

It’s interesting to read this as it seems to go against a bit of what you read out there such as Venture Hacks - How to pick a co-founder and TechCrunch - Finding Your Co-Founders.  I wonder if this is a shift?

I’m not sure that the good, rational reasons for waiting on finding cofounders is going to overcome the emotions of wanting a cofounder.

Tuesday, February 2, 2010

Part-Time Startup CTO?

I love blog conversations.  Based on my posts Startup CTO or Developer and Acting CTO, Chris O’Meara wrote an interesting post Startup CTO: Could It Work?

Chris starts with a description of the person that pretty much every startup is looking for:

Their primary characteristics are deep technical skills and a hacker mentality. They tend to have the knack for architecture. They tend to be capable planners when it comes to issues like performance and security. They tend to have the programming background to lead competent people by example and dig in and prove it where necessary. They tend to know where to find good help in terms of employees and consultants. They tend to know the operations side of a software business well enough to be the one overseeing deploys, crafting the infrastructure plans, and monitoring the health of the product. They tend to be plugged in to tech news sources to be aware of trends and understand how those trends could impact the business. They tend to understand the product management side of the product well enough to guide the technology in a complementary way.

I think that's the person you need. Common sense says you'd do your best to hire or otherwise permanently engage that lead developer. If you think that's person you need, the question becomes "what else do you expect a CTO to contribute?"

Of course, that’s a rare combination.  It’s especially rare to find individuals who are going to be strong in a) business, b) operations, c) sourcing/managing talent, d) development.  When you start the description with deep technical skills and a hacker mentality, that’s almost inversely related to the others.  Still, you can get lucky and find someone strong in several of these areas.  You also can build a team that has complementary interests and skill sets which is more common.  But often that first individual is the real challenge.  And in my experience, it’s pretty rare to get someone with interest and skills in all of the above.

Even with this almost mythical person is there a possible Founder Developer Gap?  Chris says:

Surely there are some business and technology strategy problems you're going to need help with that your lead developer can't help you answer.

I tend to agree, and often I feel like it’s a matter of interest, focus and experience rather than talent.  If you’ve found that rock star person being described by Chris, they are off the charts in terms of intelligence.  They can likely close a lot of the Founder Developer Gap.  But, I’ve seen a lot of cases where a rock star lead developer didn’t close the gap because they didn’t think to ask the questions, they didn’t have experience with the questions, and it wasn’t their focus.  They were hired to build stuff.

Chris then tells us:

In thinking about this problem I asked around a fair amount and couldn't find any solid answers to the question "where have you seen someone in the role of CTO for a startup do a great job?"  My colleagues and I interact with startups a fair amount because we're consultants. Many of us have done freelance work in the past, often for startups. We each pointed to key technical leaders that drove the development and operations parts of the businesses. A few had the title CTO but they all fit the technical rock star and hacker profile.

The main thought that gives me pause is that of earned authority. It's about leading by example. Depending on how much face time the consulting CTO has with the team, it could be extremely difficult for a consulting CTO to effect change. The consultant's advice would have to be filtered through the leaders in the trenches. Yourself and your lead dev, along with your other key leaders like product and sales managers, would need to listen, internalize and execute the strategy. I doubt a consulting CTO would have the privilege and honor of earning your team's respect directly. That generally comes from running the business together.

I think the two points go closely together.  Chris is pointing to a gap that can exist between business-oriented CTOs and development teams.  It’s much like the Founder Developer Gap, but down a level.  I’ve seen lots of cases of this.  A CTO that focuses only on business questions, but who doesn’t have a technical understanding so that the development team lacks respect and questions them.  This can definitely be a disaster.  Anyone hiring a CTO needs to know that the person is still technical.  But that doesn’t necessarily mean hands-on developer technical. 

That may be where Chris and I differ.  Can a CTO who is not ready to get their hands dirty in code help guide a technical team?  The answer is yes and it happens all the time.  I’m surprised that Chris couldn’t find examples of it.  I would guess that half of the CTOs in the LA CTO Forum fit that and are A players.   They know what the developers are doing.  They can help guide and navigate key technical questions.  But they are not going to jump in and code, even though they probably could.

The other aspect of what Chris raises is whether a part time CTO is going to have any real impact.  And certainly there are all sorts of ways for a part time CTO to be engaged.  In fact, it often changes as a startup goes through phases.  There will be key points when decisions need to be made and a deeper engagement is needed.  Then there will be hardcore development periods when the developers need to be heads down and the CTO is less important except possibly to avoid distractions for the team. 

Chris is right to question the amount of face time the CTO has with the team.  There are engagements where the CTO is primarily a consultant to the Founder/CEO and is providing advice/guidance, but doesn’t directly engage.  However, the most valuable engagements are when the CTO takes responsibility and engages.  They should jointly own the results of the development team with the team and the lead developer(s).  And certainly the CTO needs to have/earn the team’s respect.  But I’m surprised that Chris “doubts” that would happen.  Sure it can.  And it can be a function of the development team.  And, if you are bringing in the CTO because of a pre-existing Founder Developer Gap, then the challenges are bigger than when you had a CTO from the start.  Still, great CTO/lead developer working relationships happen all the time.  Maybe I’m missing Chris’ point on this.

One closing thought … Having been personally brought into a LOT of startups with all sorts of leads, developers, CTOs, CxOs, boards, etc., I can say that each one is going to be different.  The challenges, gaps, process problems, etc. are going to be different.  The motivations, skills of the people are different.  A good CTO (full-time or part-time) will be able to navigate that.