the ups and downs of investing

Images-1The ups about investing is that I really believe that we are in the midst of change when it comes to everything; education, data collection, ecommerce, transportation, urban planning, etc.  It is the real long tail of the Internet.  We are connected globally.  WIth all the investments taking place in new start-ups and entrepreneurs we are also putting money to work in a changing global economy.  That is a very good thing. 

The downs are the companies that don't succeed.  The other down is that many investors who put a lot of money to work treat a lot of their investments like a crap shoot.  Perhaps it is the maternal instinct in me but it upsets me.  Intellectually I understand that funds or even angels who invest in many businesses know the odds of success for each one.  Some of their investments might hit it out of the park while others only get on first base and others just strike out.  The down is that the care and desire to make sure each is as successful is not consistent among investors. 

I'm seeing those downs right now.  I really do try and help each of the companies that I invest in as much as possible.  I am unique in that I have the ability to heavily curate what I invest in.  I can choose when to invest or not to although there are a few others like me which I really like working with.  I happen to be in a deal now that can really use some guidance from some of the more seasoned investors in the group but the truth is they don't have the time to spend on that company because the investment that they made in it in regards to their entire portfolio is minimal.  I get it but it frustrates me.  I am an equality opportunity investor but I can afford to be with my time.

We will see many of the companies that have been funded over the past year move to stage 2 while we will see many others fail.  Perhaps it is just me but I really want to make sure everyone that I work with succeeds at some level.  To me, it is the out come that I strive for. 

Comments (Archived):

  1. kirklove

    A) You want a return on your investment (duh) though the thing that impresses me most about you is B) You give a genuine shit about the people you invest in. That speaks volumes and will go a long way to making A) much more of a reality. That’s smart investing.

    1. Gotham Gal

      i hope so!

  2. Lisa Mogull

    Investment comes in many forms. I’ll take seasoned advice over silent partners with cash any day. The people who have given us advice are, in their own way, our investors. The feedback and advice can be worth as much or more than cash and you don’t have to give away the farm. Figuring out how to bootstrap will make us more valuable in the long run.I agree with Kirklove — smart investors give a shit and I have to imagine they have much better returns. No doubt your work in the community has resulted in both Karmic and financial returns.

    1. falicon


  3. Abdallah Al-Hakim

    I think your genuine interest in the your investments and the people behind them is what will drive other promising entrepreneurs towards you. It is a good reputation to have.

  4. John Best

    There’s investing financially, and there’s investing yourself (to a degree) in a business. Following up on, and working hard for the people you work with shows a nuturing approach and genuine empathy.

    1. Gotham Gal

      its my maternal instincts at work.

  5. falicon

    I love this line of thinking!Since I’m starting to talk to a few people about investing in, one of the things I’ve been doing lately is keeping a list of who I would want as an investor and what I would look for/ask from that investor beyond money (ie. I want them to understand the ‘why’ of why I want them in the deal, and I want to understand the appropriate level I can rely on them for in that role).I think one of the key things for me to do well at this stage is set and communicate clear expectations on both sides (including, if they invest, how much time and energy they hope/expect to spend on my updates/asks/etc. over the next year or two)…Hopefully with this approach I won’t have anyone involved that brings only money to the deal…I guess time will tell how it goes (if it goes at all of course) 😉

    1. Gotham Gal

      I’m in one investment where the entrepreneur was very methodical about who came in on the investment. It was impressive. Obviously he had the product and cred to do it but still I liked how he went about it

      1. falicon

        That ‘product and cred’ bit is def. key…I guess this experience will reveal if I have enough of it yet or not…BTW – are you allowed/comfortable sharing which investment it was?

        1. Gotham Gal

          Rather not

          1. falicon


      2. Dale Allyn

        As Kevin ( @falicon:disqus ) knows (from reading my blog post about our team declining investment recently) we’ve been very selective about our investor as well. It’s not easy, but when you’ve been through a bit of business experience such things become integral to one’s approach. It should be a mutually protective and nurturing relationship.

  6. ellen

    I read Brad Feld’s new book upon your recommendation and I get it now. If you don’t have advisors who have time for you because you are a tiny part of their venture deals, then there is a problem.Having someone like you, GG, adds a great benefit to each investment dollar.

    1. Gotham Gal

      you got it. i love that you read it.

  7. PopCosmo

    I love your investment policy, and also agree with the other comments that it will drive quality companies your way to seek investments from you. Those who are open to seeking advice and input are confident enough in their plan to know that experienced suggestions can help propel a company to the next level. It’s amazing that you can share such valuable commodities as time and experience! Lucky companies who have you as an investor!