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Boulder CTO December Lunch with Tim Wolters

The Boulder CTO Lunch meets once a month with a guest speaker and covers topics and questions that startup CTOs should find interesting. This month, the group had Tim Wolters from Collective Intellect come lead the discussion. Tim is a serial entrepreneur currently working on using artificial intelligence and semantic analysis to extract knowledge from unstructured text found in social media. Collective Intellect’s customers use this analysis to inform and measure the effectiveness of their PR and marketing strategy.

Tim is considering working on a book, a startup survival guide for CTOs. Some of his ideas for the book helped lead our discussion during our meeting. I will try to present my notes under topic headings that Tim mentioned, but since this was a open free formed discussion, I am sure I couldn’t capture everything and not all my notes are completely accurate.

The Idea
People should keep a journal of ideas. Tim keeps a journal which he updates, tags, and adds ideas. On any idea, keep track of what is near term, what resources are needed, what is the cost, and what does the related market look like. (I highly recommend this! Ben and I keep a wiki, which has grown to be an incredibly useful resource and was the initial starting point for our last two companies)

Ideas should have an “Aha!” factor that makes you wonder why someone else isn’t already doing it (or some emotional appeal that makes lives better).

During the first few years of a startup you can’t work on all the ideas that come to mind, that is why it is best to keep a journal, just add little notes to the idea to keep them in the back burner.

Talk to others about ideas and perhaps have a group move on an idea and lay the groundwork while leading as an adviser.

Don’t be worried about people taking ideas. After starting a few companies you know how hard it is to really bring something to market.

What about brainstorming for ideas with a group?
Brainstorming groups have never worked for Tim, it just hasn’t worked out. If you have the right people around the table (people that can make things happen), it could work, but Tim hasn’t seen it.

Ideas depend a lot on timing in the marketplace. If the market is moving slow you can slowly look at an idea. If the market it really moving fast you need to spin it up quick and get a lot of people working on it to really make a move on the idea.

Look over your ideas once in awhile and see what still really interest you.

The Role
As a CTO, you paint a landscape of the product and market.

There are two kinds of CTOs: tactical and visionary. Tactical CTOs are internally focused, manages the team, makes the day-to-day tactics so the product gets out there. The visionary CTO sees where the product could go in the market place, signs early deals and customers, looks for features that lead towards or away from markets/competitors/partnerships. The visionary isn’t working on architecture but the market landscape, what partners will benefit the product or get it out sooner.

CTO should be thinking about things such as the three hardest problems that the company faces, so they know what will also be affecting their competitors.

People who liked architectural purity but learned it isn’t as import at winning at the business end up making great CTOs.

CTOs need to stay involved with customers to make decisions about the project innovation and development. Stay active on sales calls, talk with sales people, read all the RFPs.

Becoming the CTO vs VP of engineering?
Are you good at managing or not? VP of engineering is a managing role. If not, divide off the management as soon as possible (in his case that wasn’t possible until the company was about 20 people).

Good sales people leverage a CTO as a company evangelist. If you are a CTO you have to be comfortable with presenting and publicity. You will be at conferences, sales calls, giving presentations, and fund raising. If you aren’t comfortable with these things, get comfortable with it.

time spent:

  • 10% guiding research
  • 30% Sales
  • 30% Partnerships
  • 30% Biz Dev Dealings

After some startups, successes, and expanding your network things like getting a team, funding, and getting a startup off the ground are much easier the next time.

It will take 3 to 5 times longer than you think to get a project going if you are an unknown entrepreneur with no reputation.

Don’t solve the big unsolvable problems first, the first time start with smaller problems and develop a reputation while solving them. Angels and VCs aren’t funding research efforts, don’t just chase after big impossible goals.

After a company is bought, it makes sense to make the purchaser successful. It builds on your reputation.

Become a big fish in a small pond and then move to a bigger pond.

Putting together the team
The ideal size for an engineering team is 6-8 people, bigger teams have difficulties maintaining the right amount of communication.

For hiring, Tim personally sits down with the key hires, and if it is research he does interviews with applicants as well.

The Traps and Pitfalls of Startup Companies
3 things that companies get stuck on that can kill the company.

  • Problem with getting over enamored with their original idea, startups must be able to adapt
  • Getting enamored with the research technology, for technology’s sake
  • Getting emotionally tied to architecturally purity. Working on layers of abstraction on abstraction to avoid some possible future problem.

Other things that kill companies (which are kind of like a marriage)

  • Not the right chemistry
  • Bad culture or losing company culture
  • Employees need some sense of allegiance. If they don’t have it cut them immediately
  • Lacks a culture of adaptability
  • Not thinking about how to quickly get to the market and solve problems

Continual code death march. Sometimes companies go on code marches to get something to the marketplace. This can’t be done many nights or it will start taking a toll on other aspects of your life. Strive for balance.

During a startup, you continually are hitting false summits, you think that if you could just get that contact, solve that roadblock, pass this milestone, or make this key hire then everything will fall into place. While these are important as milestones and you should celebrate them you are not done. Or rather, it typically doesn’t get any easier. What it does is takes more risk out allowing you to go solve bigger/other problems.

When founders or others in a company argue, which they need to do sometimes, don’t do it in front of everyone. Discuss disputes offline, reach agreement and present a unified front to the company.

Thanks so much to Tim for sharing some of his thoughts with our group. I will leave you with a final question and quote. Someone once asked why Tim likes to start companies?
“I like to pick where I work and who I work with.”

Written by DanM

December 11, 2008 at 9:50 am