I generally am working as an acting CTO for about 3-4 start-ups or other companies at any one time. Most often I'm being brought in the early stage, Start-up or Expansion (as the company looks at new product lines). My focus in this post is on the Early and Start-up stages - expansion is more of a consulting, focused project role and it acts different. I was just talking with someone who asked me to define how that could work and what they meant. Great question.

This post is part of my series “ Startup Lessons ” Elephants, Deer and Rabbits – Some thoughts on start-up segmentation know that this advice won’t apply to every possible startup – but I think it applies to many. When you start your company the very first question you need to ask yourself is which Nearly all of the mistakes I made at my first company I fixed by the time of my second company.  This This is the only mistake I repeated twice and it is a mistake that I see many, many companies make.

This is part of my ongoing posts on  Startup Advice .  There are people who tell startups that they should hire the most senior people that they can find.  It is tempting because you not only see that they were VP Sales at 3 other startups but also that they have great access (according to their resume) to senior executives at companies you’re trying to target.  Only Hire A+ People Who Punch Above Their Weight Class I’m not one of those. 

know that this will sound like a random post topic for startup advice but I promise it’s relevant.  You When I started blogging I had an idea.  I I would take all of the one-on-one conversations that I have with entrepreneurs from the things I’ve learned and just write them up for anybody to read.  This File this under entrepreneurial advice I

This is part of my ongoing series Startup Advice .  Many startup companies hire advisory boards.  If you plan to set one up – no problem.  Advisory Board Problems : There are several problems that I have encountered myself and in my many discussions with CEO’s who have set up advisory boards. It’s very tempting.  It’s mostly done by first-time entrepreneurs who want to persuade (bribe?)

If you’re a startup and you don’t have a close relationship with a few law firms you’re really missing one of the most important relationships that any entrepreneur can have. When to get a lawyer - If you plan to be a venture or angel backed technology company (what I mostly write about) the best time to start meeting and getting to know lawyers is long before you ever start your company.  I recently read a post over on VentureHacks titled, “ Top Ten Reasons Entrepreneurs Hate Lawyers ” written by Scott Walker (who blogs on legal issues for entrepreneurs ). 

Francisco Dao came up with the idea of letting 10 companies that weren’t selected for Twiistup to do a presentation the night before to a group of people and let the audience pick one company to win the final slot at Twiistup.  I I’ll put up the video when they post it on their website. Many of them have their iPhones and laptops Most people suck at presenting to big groups.  It’s It’s a shame because the ability to nail these presentations at key conferences can be once-in-a-lifetime opportunities to influence journalists, business partners, potential

I’ve been having discussions with several people recently about the role of the CTO (Chief Technology Officer) in very early stage companies. In December 2007, I described how I commonly take on an Acting CTO Role in a Start-up . I used an image from Roger Smith that describes the varying roles of a CTO as the company matures. However, I’ve now begun questioning how and what an early-stage / startup CTO should Most often at the earliest point in the life of a startup, the dominant need is certainly to produce product to get something in the market, get funding, etc.

Tags: Pitching VCs Start-up Advice startup technology vc venture capita This is part of my ongoing series “Pitching a VC” – the outline is here. You’ve You’ve pitched several angels and VC’s.  Everybody seems to like you but nobody seems to be getting out their checkbooks. 

Many entrepreneurs make the mistake of thinking that funding is something you do in “funding season,” some mythical  2-month period when you’re ready with a great Powerpoint deck and you hit up all of the VC’s at the same time so that you can quickly raise money and get back to the job of building a business. Tell them about what you’re up to in your business, show them your product or prototype, tell them your strategy, talk about the deals you’re working on and seek feedback. This is part of my ongoing series “Pitching a VC” – the outline is here .