It is common knowledge that it’s unwise to fight Russia in the winter. As such, I have been trying to convince my programmers in Ukraine (and Romania) to move to Cabarete. The setting and quality of life are extraordinary in Cabarete. Besides, I would much rather fly to Cabarete for in person meetings and have everyone on New York’s time zone, rather than have to deal with a 7 hour time difference and flying 11 hours on Ukrainian Airlines several times a year.

To help sway them, I decided to build a really contemporary office center whose design is inspired by WeWork and Neuehouse, but adapted for the Caribbean and integrated in nature. The idea is not only to house the developers for my projects, but also to offer great co-working space in Cabarete open to all entrepreneurs around the world. Living in Cabarete can cost as little as $1500 per month with everything included. This is a great combination for entrepreneurs who are short on cash and want to be close to New York for potential meetings with investors and clients.

The project is called Silicon Cabarete and is part of a playground I am building at La Boca.

Sadly things in the offline world don’t move nearly as fast as in the online world. I bought the land two years ago and am still impatiently waiting for the permits. As entrepreneurs we know that we don’t start with the final product, but rather build an MVP (minimum viable product) and launch an alpha, then beta product. I decided to do the same here and to already start the process of moving programmers here in more a humble setting.

Quite appropriately, I transformed the garage at Embocca where I am staying in Cabarete into a small open space. I already had 8 team members come visit for a few weeks.

The bottom floor in the picture below is said “garage”.

The team seems to have had a great time and we were the most productive we’ve ever been.

I suppose the view from the office did not hurt.

Various locations became fun work spaces with Bagheera clearly becoming a productive member of the team.

We got to know each other better over meals and poker.

Hopefully many will opt to move and that this is the beginning of a trend!

Sometimes you just bet on people. I mostly invest in consumer facing startups, especially marketplaces. However, in July 2006, my good friend Auren Hoffman introduced me to Tod Sacerdoti who was CEO of POSTroller, a video ad company (which became Brighroll in November 2006).

I have to admit I did not know much about the video advertising market and had limited expertise in ad tech. It was obvious that video advertising was eventually going to be big, but I was not sure what the best way to tackle the market was.

Fundamentally, I really loved Tod. He was super sharp, passionate, confident, very honest about the status of the company and their market. It was clear to me that he had the grit and tenacity to stick it out and figure out how to make it. I just had to back him!

Over the years, as we interacted in more personal and intellectual settings (e.g.; he hosted a dialoging session I attended on “”How do you live forever?”), I have only gotten to appreciate what a smart standup guy he is, on top of being a passionate entrepreneur.

I was fortunate to have liquidity at the time (coming on the back of the sale of Zingy) which led me to make a bigger bet than I usually do. I ended up investing $100k at $4 million pre back in August 2006. Based on the public information it looks like Yahoo bought the company for $640 million, which post-fundraising dilution should turn into more or less a 60x return for me, my most successful exit to date!

Thanks Tod, you rock!