Posts from musings

the investment life.

VC-Stock-ImageI don’t know if I have come in to my own as an investor or somethings just piss me off but it could easily be a combination of the two.

I am always learning in this business.  I have certainly learned that nothing is standard when it comes to investing. A few things happened recently that I truly learned on.
I have a thesis which is that I want to own 1% of the company from the very beginning which based on that amount I like to put in I pretty much have to put money into the very first round.  Not an idea but a real live product that I get excited about and an entrepreneur I believe can grow the beginnings of something into something larger.  That means hiring a team, raising money, thinking out of the weeds, making tough decisions and being completely out of their mind focused on success.
I always get a side letter that insures that I can continue to invest to keep my pro-rata share at every capital infusion until I choose to opt out.  At one point I have too much exposure (probably around the Series B) and then I choose to pass.  Then I look at the amount I have in the company not as a percentage but as a dollar amount that will hopefully have a multiple exit.  It is purely a head switch.
So here is how I screwed up.  I forgot to get a side letter with a company I invested in.  At the beginning I wasn’t on top of this but I finally figured it out.  I think that I was in between figuring out the side letter thing and this company might have been the last one without it.  Alas because one of the things I have noticed is in SF they like to raise notes over notes over notes.  What that means is when they finally do get their Series A and the note converts into stock what you believe you own is not what you own.  Needless to say I was pissed, I had a pissy fit and then I blamed myself.  Lesson learned.
Move forward on to other things that piss me off.  There are a few investors out there, not angels but funds that I refer to as micro-funds that love to get some sweet deal that is better than everyone else in the round because they can write a larger check.  It is that or they demand some kind of advisor shares on top of their investment.  Everyones money is the same in each round as far as I am concerned.  Some investors are more active others and some are completely passive but that money helps the entrepreneurs get to the next stage of their business.  The good news is that in my side letter I negate getting screwed by the micro-VC who comes in with their better terms than everyone else in the seed round.
So returning to reality after being off the grid for a full on month has been quite a whirlwind.  Perhaps while I was gone I found my voice but maybe it is just the last 9 years of investing and seeing some really not great stuff out there that I just do not like and I just help not holding back my anger.

Being Authentic

imagesA group of amazing people who I have had the pleasure of meeting through the investing world came up with this great idea of doing founders breakfasts.  As small as the start-up tech community is many of the founders do not know each other.  The concept behind this breakfast is to get a group of founders we each know (rarely is there any cross-over) get together and discuss what is top of mind in regards to the trials and tribulations of growing a company.

The breakfast this past week one of the men brought up something that I have never heard uttered out of a mans mouth.  He said he is hiring people that are better engineers than him, better at many more things than him and his fear is that he will be discovered out that he essentially knows nothing.  It was amazing.
Women, for whatever reason, tend to have this inner voice saying to think there are days when they feel like someone will realize that they are totally faking it.  They know nothing.  It was seriously refreshing to hear a guy come out and say that.
Then the conversation turned into creating a culture in your company.  It was really interesting to listen to each entrepreneurs transparency, leadership and expectations with their team.  It was really interesting to hear what works for one might not necessarily work for the other.
What I believe this all comes down to is the importance of being authentic. Everyone does it differently.  There is no right or wrong way of how you build the culture in your company.  Company culture is essentially an extension of the entrepreneur who started the company.  I think the key is being authentic.  Be true to who you are because it will come across to your team.  When you are not authentic that comes across too.  Be yourself because it is a helluva lot easier than pretending to be something that you aren’t.  Also…on a side note, I have thought for years I be would found out that I have been totally faking it.

Generational differences

imgres-1When Elvis came around and kids went gaga their parents freaked.  When the Beatles came to town and kids went bananas their parents freaked.  The generational differences between the youth and the older adults seems so vast and almost comical looking back at it.  It appears that this generation of parents and adults are much more connected to the youth.  There is a blurred line of parenting vs a friendship which is a whole other blog post.  Yet as technology has encroached on our life through social media the lines appear to be more divided than you think.

Perhaps some people move forward and others don’t.  I do not know if it is about curiosity or it is just innate.  My Grandmother was still reading Vogue at 85 and paying attention to the latest fashions and buying them.  I have always been interested in the latest and greatest from fashion to food to home design to music to technology to trends.  Personally I think it keeps you young.

Yet there are many people I know who are still listening to the same music they listened to in college, that are wearing the same clothes, have pretty much the same haircut, etc.  There are others who are all over the latest stuff and because of that they can connect with the youth.  They are using social media, they understand the impact it has on their businesses and the world around them, they are paying attention to the culture and the shifts.

It is almost the start-up vs corporate America.  The big corporations, at least some of them, seem to have a disconnect but at some level realize that they do and are not sure how to move forward.  Someone told me a story about going to do a freelance job for a huge corporation around marketing and branding as they move forward into 2015.  They actually asked if they could help them get into the hip stuff.  It made me laugh because I know exactly what they mean.  They understand that there is a movement but they aren’t quite sure how to get on that band wagon.

It is almost a digital divide that is purely generational from the users and the non-users.  My guess is that back in the day some parents thought Elvis and the Beatles were awesome.  At least I hope so.

Women conversations

imgresMy friend and I were talking about women events and listservs and the conversations that take place on them this weekend.  Having just launched the Women’s Entrepreneur Festival applications for 2015 it was relevant to my personal reflections on the event each year.

I have been watching the conversations on the recently launched and have always been fascinated with the conversations that take place at the festival and listserv’s that I am on.  The topics are vast depending on the listserv.  I was expecting a lot more conversation around business and what I found is that those talks certainly take place but most of them are relegated to female fodder.  What I mean by that is anything from does anyone have a favorite cookware line to what is the right attire for a conference to best shopping sites to where to get a blow out in Chicago to how do I ask for a raise.

We are all looking for a connection to other women that we can talk about anything from where did you get those fantastic shoes to how do you get food in the fridge for your kids when you are in the middle of launching your start-up to damn I had a shitty day.  Finding those women who in the same space you are in your life is important or having women mentors who have been through it before.

I see it at the Festival because the ages span from 18-60+.  When you get a room of women together the conversations go everywhere and sometimes they are really taking a deep dive at your business and other times they are about the best place you just recently dined.

I guess I wonder if there were any listservs out there for men what kind of conversations would take place.  It probably would not be all business either but their fodder might be more relegated to sports, music or a good meal.  I am purely guessing here and perhaps being judgmental but I see those convos take place among the men I know.  They are generally not asking about where they got those amazing shoes.

Thinking of all of this at a birds eye view this is exactly why it is so important for companies to have an even balance of men and women in each area of the workplace because men and women both think differently, have different daily interests and are brains are just wired in a totally different way.  I just find it interesting.

PR or Marketing?

imagesPR and marketing is one of those expenses that get put on simmer on the back burner in start-ups.  There is always this lingering question about when is the time to spend on PR.  Do we need PR?  Perhaps we only need a marketing person who can help drive home the brand with social media and at the same time work on customer acquisition.  Both can make an impact but sometimes you need just one and others times you need both.

Marketing is a key component of most start-ups.  The role of marketing person is changing in start-ups.  They focus on the product that in turn connects with the customer.  The hope is that customer will then become a customer and that can be anything from buying the product to consuming the content on the site.  Essentially customer acquisition.  Marketing campaigns range from just making sure that there are tweets going out to Instagram posts or keeping up the Facebook page on a daily basis.  It can also be about paid ads on Facebook that drives traffic.  Using either paid media (paying for ads), shared media (social media posting) or earned media (bloggers and other third party sites that will drive traffic by writing about the company).

PR on the other hand is a component of marketing because one could say with our marketing how can we do any PR.  PR is about promoting the brand through a campaign.  It could be getting articles written about something specific that has happened.  PR pushes out the marketing efforts in a big blast.  One way communication.

Marketing is defined as: the action or business of promoting and selling products or services, including market research and advertising

PR is defined as: the practice of managing the spread of information between an individual or an organization and the public.

As the media landscape continues to evolve yet it is important to realize that marketing is to find your customers and determine a way to engage them.  PR is about being visible about what you are doing for potential customers that weren’t so easy to find.


It takes time for companies to grow

300x210One of the things I have been thinking a lot about is the pace at which companies grow.   I am involved in companies at the very beginning.   Super early stage so there are few employees, revenue is just starting to get into gear, even the path to growth is not exactly secure.  On the other hand I do get to see companies that are very mature and the different issues that comes with getting a business to become huge.  There are so many components that have to work from the management, to the investors (board), to the leadership etc, etc.

Sometimes companies get to a place where we all know that they could become 75% bigger but for a slew of reasons they just can’t get there.  Becoming a multi-million dollar company is a long hard path.  There are a few here and there that just become success stories over night but they are few and far between.  We all read about them and unfortunately many of them seem to be the norm but they are so far from it.

I have watched more than a handful of companies that I am involved with start to grow.  The team is in place, the revenue model is working, the company grows month to month.  The next step is far from cruise control but more about constant pushing, prodding, molding and hitting the milestones.  It is very different from the anxieties of early stage growth.

Seeing the companies I have been working with start to move into this next stage of their business is insanely rewarding and exciting.  I couldn’t be happier for all of them.  My involvement will change as they grow up but that is a good thing.  New eyes, new money, new milestones.  These things take time and as always more time than you think.

The journey ends

eiffeltowerWe ended our month long trip in Paris by going to the top of the Peninsula Hotel.  The hotel went through a $575m renovation and has reopened its doors to quite the fanfare.  At the top there is a restaurant that resembles a glassed in jewel box.  Looming over the restaurant is the Eiffel Tower.   It is magnificent.  We just had drinks on the terrace where the ladies get white cashmere shawls for their shoulders if they get a little cold.  We sipped on our drinks, took in the views and reminisced about our last month of travel.

It has been an amazing journey on so many levels.  We spent 24/7 together for the past month and it was really great.  It reminded me of our cross country trip post-college and our honeymoon.  The wandering duo.  We are able to keep the Wilson company going regardless of where we are. We did not attend meetings, we did not do phone calls ( unless need be and there were a few of those ) but we both closed on several deals, did a few real estate transactions and kept up.  It is pretty amazing that you can basically do anything from anywhere just at a different pace.  The pace is what was important.

Some places we went to I can’t imagine ever returning to while others we will most definitely go back to such as Provence, the Bordeaux region and San Sebastian.  Some good hotels and some ok hotels.  I have wanted to build and open a hotel for years.  Trust me I know what would be the perfect hotel at this point down to how the robes are hung, how the soap is wrapped and how the coffee is made.

Getting back to reality will probably be as always where I just hit the ground running but there is no question that our heads have changed.  I can’t quite put my finger on it but it has.  Certainly being in an empty house with all the kids off in their own lives shifts everything yet that is just one component.  I am feeling really good about our stage of life and am so glad we took a month off to get there.

ollieWhen we returned the first thing I did was whip up about 20 dozen chocolate chip cookies and bake a brisket for 12 hours.  We were getting up the next morning for parents weekend and the day called for a picnic on the hill.  I prepared the picnic that night and the next morning.  Not only did we see Emily and Josh but Jessica was up there the day before and left Ollie for us to take home.  Jessica took Ollie for the past month.  That was huge.  We picked him up, had a picnic, saw the kids, drove back to the city, attempted to get back on NYC time, dealt with mail for the past month and made dinner to have Jessica over.

On one hand it seems like we never left but there is no doubt that we did.

A journey and the next chapter

urlI have been preparing for the empty nest chapter for the last 8 years.  Someone told me to look at my daily life and color code each of my activities.  I realized very quickly that a huge chunk of my time was devoted to the family.  That was fine for then but what would happen as each kid started to move out and begin their own life journey.  They would begin to rely on themselves not me and that huge chunk of time would become smaller and smaller until Josh went to college.  So I began a new journey for myself.  I had already been blogging and essentially leveraged that into angel investing, a conference (thanks to Nancy Hechinger) and a variety of side projects.  Fast forward 8 years and I have reinvented myself back into the business world in a way that works for me.  I have been fortunate enough to be able to do this on my own terms.

Even though I was preparing I still always put family first.  When plans were being made over the past 8 years I still thought about making sure I was present until Josh flew from the nest.  This past week I started to get some inbound asks about events to speak at and even some asks for a drink.  I had a huge aha moment when I realized I could make any decision I wanted.  I did not have to be home in time to make dinner, I did not have to even come home until late at night.  I did not have to be present.  I could do a drink, I could get on a plane and speak somewhere if it worked into my schedule, I could go on a quick trip with a friend for four days and not give it a thought.  The only person I have to think about in regards to evening or weekend activities is Fred.  What a concept.

We are entering the next chapter of our lives.  No better way to mark that chapter with a journey.  To go on a trip where there are no rules or restrictions and we can literally be on the road with no responsibilities is what we plan on doing.   Fred and I will be going on a month long vacation through Italy, France, Spain and Portugal.  We are staying on the coasts.  The trip has been in the planning phases for quite some time.  We will be off the grid (as much as humanly possible).  I can’t imagine not answering emails particularly with the businesses that I am involved with but I certainly will not be as quick on the response as usual.  Anything new will be ignored (must be that way).  No board calls either.  I do plan on blogging about the trip because not only do I enjoy recording all of our travel journeys it is a reference guide for life although the kids say I shouldn’t blog at all.  We will see.

The next chapter is going to feel strange but it is the progression of life.  Seeing our kids fly from the nest and become their own individuals who can take care of themselves is insanely rewarding.  I am sure it will feel strange having an empty house but how could it not.  This journey is marking the beginnings of our next chapter.  Having a lot of feelings from bittersweet to excited to I can’t believe it but all and all it feels good and it feels right.


imgres-1Linked-in is brilliant.  You can keep your online resume up for the world to see.  You can link with new people and old people.  It is a smart business tool and my guess is it will get even better for different stages of people’s lives from college to volunteerism to retirement.  I would guess that the majority of people who read this blog have a Linked-in profile.

Facebook is a different model that is skewed towards your social life.  I understand them both and they are no doubt the foundation of our times.

Here is the thing.  I have a Facebook page but I never use it.  I have one to so I can see how companies we are involved with use the platform.  I have a Linked-in account for basically the same reasons.  I pretty much let anyone be my friend or connect to me.  As long as it does not flood my email box it is fine.  It doesn’t because I have set it up this way.

If you want to talk to me or reach out to me then email me.  I do not want to answer requests from Linked-in.  I am pretty public because I blog daily.  My email is on my site.  I answer those requests.  Once in a blue moon I will answer a Linked-in request but rarely.  I have taken to ignoring them.  If you really want to get in from of my eyeballs then email me directly.   Otherwise, you won’t be getting a response.   And one more thing…I love Twitter but sending me a direct message with a request won’t get a response either.

Seizing the moment

imgresAs we all begin to wind down the summer we all see our email boxes start to peter off, the social media begin to quiet down and the instagram photos scream vacation.

I have been thinking a lot about participation vs observation and the importance of the first vs the latter.  It seems to me that there has been an insane surge of observation and we are all begging for and needing a little more participation.  There are a lot of clues in trends that are happening that speak to that.

When I see families out for dinner and everyone is peering at their phones it upsets me.  When I go to a board meeting and people are on their phones more than they are participating in the conversation it angers me.  I know I will make notes to myself on my phone or look up something that is worthy to the meeting but I really do put the phone away.  It isn’t right.   Even when you go to a museum and people are just posting away and not truly enjoying the moment and the experience they are having.

I had a conversation with an editor at Eater about the importance of sitting down for a meal with friends and family.  I continue to think about it.  Why is it important to sit down and have that meal.  I think it comes down to seizing the moment.  Participating in conversation.  It could be about anything from books to movies to the meal you are having or the political landscape but those conversations are important.  People tend to look back at those times with fond memories.  I have yet to see anyone look back at a snap chat, an instagram or a blog post with fond memories.  It is the human connection and those human conversations that I find much more interesting and memorable than the screen of my phone.

Hoping to seize the moment often as the summer winds down.