shadow.vc

So Immature: A Digital Transformation Maturity Model

Last week I was talking to a friend about digital transformation in the construction and real estate space. We agreed that the market is…

We are a reflection of our Limited Partners

Yesterday, I had a typical day for a seed-stage venture capitalist. 6 calls with our incubator company CEOs, 1 call with an investment that we are trying to get over the goal line, and 2 calls with corporate venture capitalists. Then a myriad of meetings…

A Startup Survival Guide to Tough Times

I remember the day in 2008 when my bank called me and asked for a meeting. I was running a startup that was gaining incredible traction — until 2008, that is. My startup was focused on the construction industry. The bank gave me notice on our line of credit…

Breaking News: Venture Capital is broken.

Venture capital is broken. It’s broken because fund managers don’t understand what it takes to succeed. They likely entered VC because it was trendy and they saw big money in tech, but they don’t know how to dig in and execute on the work.

Innovation has been killing the planet.

The planet is on fire. Literally. Australia is in the middle of a particularly devastating bushfire season. I’m not here to debate climate change or how bad it is or isn’t; what I want to focus on is waste. If we don’t consume it in the first place, then we…

Employee, Contractor or Consultant. How to hire the best fit.

I’ve built a dozen companies in my career, and I know that human resources decisions can be complicated. In my early businesses, I used contractors because payroll was a pain. It wasn’t just the tax burden; it was that…

The truth. A machine will take your job.

AI is overused and applied incorrectly 90% of the time, but it’s still real. And it’s here now. We’ll start to see real AI solutions hit the market in the next two decades. Artificial intelligence isn’t new — it’s just that we’ve reached a point in time where…

On being an investor.

I’ve been a full-time investor for the last three years. I do some paid speaking and advisory work here and there, but I make my living generating returns for myself and my co-investors. It is hard — very hard, actually — but it’s also the most fun I’ve ever had. It barely feels like work…

How former Yankee Mark Teixeira became the new voice for real estate placemaking

Mark Teixeira spent 14 years as a professional baseball player, including a season with the Atlanta Braves and nine with the New York Yankees. In that time, he won a World Series, became a…