Gotham Gal: Question of the week #20

Once you begin investing in companies you must continue to invest to grow your portfolio. I have actually been thinking alot about the question this week so it is a perfect time to answer it.

How many active investments do you like to have at a given moment in time? Because you like to take an active role, is there a limit to how many you can be active in at once?

I do have a few investments that I am not that active in for many reasons. Notice the word not which means I am still active at some level. Some don't need much help, others go in waves, others have moved into a different realm with other rounds of financing and some are not in my backyard.

I do not have a number in my head about how many investments I like to do in a year. I have the flexibility to do a deal when I just think it makes sense. I am definitely hitting a point where I am probably over-extended but I am also about to see many deals move to the next level of capital. My guess is that I will either take a board seat or be more of a consigliere to the entrepreneur instead of being involved as I have been.

There are times that I think I should just hang back for awhile but that never seems to happen. There are times when I know that I have hit the wall but it all seems to work itself out. So is there a limit? Probably but I have not figured out exactly what that limit is. Just when I think I hit a limit, I seem to pull something out of a hat. At one point the hat might be empty but it hasn't happen yet although I might just not know what an empty hat looks like.

companies I have invested in

more investments →

books of the moment

Peggy Riley: Amity & Sorrow: A Novel
A mother drives for days with her daughters and ends up in a random Oklahoma town after crashing the car. They come from a polygamous community where there were 50 wives. The mother had grown up knowing life outside that community. Over time, after leaving, she almost becomes deprogrammed. The realization of what she did to her daughters who no nothing outside the world they came from including how to read. Then there is the family that brought them in. It is a fascinating story. Well written. Worthy read.
Charles Graeber: The Good Nurse: A True Story of Medicine, Madness, and Murder
An amazing true story of a male nurse who was arrested in 2002. I actually remember the story as I followed it in the papers. This nurse was a serial killer who had probably murdered over 400 patients that were under his care. A seriously well researched book. Great read.
Meg Wolitzer: The Interestings: A Novel
Wolitzer writes about a group of camp friends who all come from different walks of life (some on scholarship) as their friendships continue through their mid-50s. At the beginning the story seems trite but as you continue to read there is a lot of be said. The story is sticking with me. She makes the case that everything that happens to you from your childhood makes an impact on who you become or don't become. Worthy read.
Elizabeth Strout: The Burgess Boys: A Novel
Strouts last book won a Pulitzer. She focuses on family issues. I enjoyed this book much more than Olive Ketteredge which I found utterly depressing. This book follows two brothers and a sister who live in the shadow of their fathers accidental death. Like most siblings, all have turned out very different yet they are connected. I did not love any of the characters, like her last book, yet as The Burgess Boys moves forward and memories are revealed, it is an interesting perspective on human character.
Tamara Shopsin: Mumbai New York Scranton: A Memoir
Great book. A witty spare inventive personal diary of Tamara journey from Indian to New York to Scranton. Really really enjoyed the book.
Michael Lavigne: The Wanting: A Novel
An incredible book that tells the human side of the many layered issues in the Middle East. From immigrating to Israel from Moscow, to being a victim of a suicide bomber yet surviving, to being pulled into an Israeli radical group. Each character is connected. Very layered well written book. Powerful
Alessandro Piol: Tech and the City: The Making of New York's Startup Community
A history of the Internet that I lived through. Great job of recording what happened.
Amity Gaige: Schroder: A Novel
Not sure how much I loved this book. A father loses his child in divorce and decides to kidnap his own daughter. He is not a stable person but he obviously loves his daughter. His own childhood has made him a disconnected human being. An interesting journey but not sure I'd recommend.
Ernest Hemingway: The Old Man and the Sea
Classic.
Janice Steinberg: The Tin Horse: A Novel
a good novel that not only tells the tale of another dysfunctional jewish family in the early 30's but interweaves pieces of los angeles history throughout the book.