Reality of Angel Investing – Gotham Gal

Joanne Wilson, a famous angel investor, who also just happens to write a blog called “The Gotham Gal,” recently told us about an investor who wanted his money back.

“The note had come due awhile ago and he was expecting his cash back with the interest. Spoiler Alert…that is never going to happen.

“I have often espoused that importance of legal documents from the get go of building a business. I am not a fan of the SAFE documents or notes in general because they are nothing but a piece of paper with zero work done and lessons to learn. Going through the education of understanding a document and the responsibility of taking cash from others is worth every cent especially from the get-go. Notes and SAFE documents cost very little to produce so I get it for a first round but that is the one and only time to have them. 

“Founders take capital with the hope that the money they raise will give them the ability to grow their businesses, their hopes and dreams, their ideas. Investors participate because they too believe that there is an opportunity to support a founder financially that benefits their pocketbook but also benefits their desire to help others build. 

“Many early stage angels should not be putting cash out there unless they understand that the chances of every seeing that capital again is low. I have seen investors write to a founder (what this particular investor did) and ask for money back with interest. The business is still alive but struggling so where does he believe the cash is? Then I have seen investors see how the company is growing and they expect a return when it is time to put money back into the company not take it out. I have told founders just to tell those investors to read their documents because they are not getting their cash back now unless some secondary buyer wants to buy them out.

“Certainly when the company gets into their Series C and onward there is opportunity to sell for the first set of investors, as there should be. Secondary markets should be bigger than they are. But if you are investing with the hope that you will get your capital back in a few years or a note with interest regardless of the companies standing, then you should NOT be investing in early stage businesses. Remember whatever you put in has a bigger potential of not coming out.”

Click here to see Joanne’s column.

Are We Being Recorded ? 

Joanne Wilson

I just read a blog post written by Joanne Wilson, an angel investor, blogger, and co-founder of the Womens Entrepreneur Festival at Gotham Gal Ventures. 

Joanne is married to Fred Wilson of Union Square Ventures. Together, they are two of the biggest investors in the tech business. When they  give their opinion about technology trends and applications, I listen. 

Joanne just wrote about her experience with Siri and Alexa.  “Having Siri or Alexa overhearing everything in the privacy of my home and somehow knowing who else is around with their phones and then using that data to push information at me and them is something that I am absolutely not comfortable with. Those big ears might make life easier and perhaps a bit entertaining but 24/7 input is not ok. I am unplugging all of these devices immediately.”

Read more about what she has to say here


My Facebook Feed

If You Can’t Stand To See Your Child Unhappy, You Are In The Wrong Business

Joanne Wilson

I want to share a post by another blogger who focuses on food, books, and music even though I’ve have seen her lately write about women, travel, and parenting. Her name is Joanne Wilson and she is the Gotham Gal. Joanne is also an angel investor in a number of start-ups and every member of her family is a blogger, her husband Fred and children Jessica, Emily and Josh.

I was amazed by a post she did last week spotlighting a New York Times story about “parenting.” I feel Joanne was able to capture the essence of the article so well that she really made me examine my own skills, not that I needed Joanne to do that for me. I have always asked myself if I spent too much time at work and not enough time fawning over my daughter. I have to admit that I would not have changed a thing but I do get a little self-conscious when I see friends inserting themselves into every inch of their adult children’s lives. I kind of want to do the same thing but I have a very strong force that stops me, my daughter.

I truly recommend that every Digidame reader reads this story and share’s it with friends. You don’t have to have children to appreciate the message of Gotham Gal’s post. You can spot yourself or a friend very quickly. Thank you Joanne. Well said!

Click here to read Joanne’s blog

Working Virtually From The Adriatic


Here I go. The countdown has begun. In just four days I will be traveling to Croatia, Slovenia, and Montenegro with Eliot and friends Ruth and Howard Greenberg. We planned this trip months ago. Little did I know that in addition to keeping up with my PR work for HWH, I would have a daily blog post to write.


I think this is my 43rd post. As I mentioned before, writing is the easiest part of this endeavor. Researching the facts, finding related links and photos, proofing, and finally posting, is very tedious. Maybe it’s quick and easy for others, but everything takes me a little longer. 


I am not looking for sympathy. I am looking for suggestions. I want to  post every day, but the rigorous schedule of touring with a group is not going to leave me a lot of time.

However, I am determined to post every 24 hours because that’s what serious bloggers do. I am enamored of Joanne Wilson, the Gotham Gal, because she  manages to post everyday no matter where she is. Wife to Fred, the super VC, mother of three and an investor herself, she writes a blog about  women entrepreneurs, food, and art.  Every morning when I wake up, Joanne’s blog is waiting for me in my email box. I am waiting for her to slip, then I can too. 

Joanne Wilson

Even though we don’t leave until Wednesday, I am all packed. At least everything is laid out on the dining room table. I learned a long time ago when we started traveling around the world not to wait until the last minute to get my things together. You can’t combine work and play without being totally organized. I have done this so many times before, but this time it seems totally overwhelming. I must get through this. I have made lists, My lists have lists. “Don’t forget iPhone, IPad, iPod, chargers, netbook, iPhone tripod, Bluetooth earpiece, Fitbit, Fitbit charger, spiral notebooks, and pens. I have to check time differences and wireless capabilities at each hotel we are staying at, My worse fear is traveling without wifi.

I can’t stand not being connected. I remember when we traveled on the Oceania Cruise Line’s Nautica to Southeast Asia six years ago, We rented a Satellite telephone so I could call the office every day. We would have to stand on the upper deck, face the sun, and tilt the phone in such a way that the call would go through. The cost of that extravagance was over a $1000. Today, I just download an app called Line2 so I can call home free wherever wireless is available.  

Working remotely from anywhere in the world now is possible, No more excuses. Maybe that is what scares me the most.