The Tedium of Being a Founder

We glamorize the life of a founder--the big picture idea person who creates something big out of nothing.  They lead a team with vision and bold thinking, guiding a ship from the helm.


That certainly seems to be what people believe--because I can't tell you how many founders are surprised when they find out how much of the job is...  well...

Mind-numbingly tedious.  

So much of what you wind up doing as the founder of a company is dealing with a seemingly endless pile of boring crap.  You're pouring over legal documents, traffic analytics, hundreds of resumes, signing up for things, looking up available domain names, getting domains to propagate, hours and hours of e-mail.

I once had to categorize 65,000 job titles into categories of similar jobs that made some sense--because, you know, a managing director isn't the same as a funeral director.

Obviously, you need to have a great idea, but that's pretty much where my own skill as a founder ended.  I am a terrible executor of small administrative details and so not only was I surprised at how many there where, I felt like it emotionally dragged me down as well.  

Being in a startup was supposed to feel freeing relative to a corporate environment--but the lack of resources and bench support didn't make it feel very freeing.  

The key to getting over that is to get successful enough, early enough, to move things off of your plate.  When Steve Jobs decided that the iPhone needed to be this thin, the job of executing it fell to a team of folks that included a guy that just tests glass strength all the time.  Now there's a tedious job: Glass guy for the iPhone.  

Sometimes I wonder if the key to success isn't so much in the big vision, but in figuring out how to get rid of the four or five things you really don't want to get stuck doing.  


Disrupting the Screen: Backing Tinkergarten to Get Kids Out to Play


A little more than a year ago, I got a note from Brian Fitzgerald, a Product Manager I met while I was at First Round.  He was "taking time with family" to figure out what's next.  

Most people take that to mean that they'll stop spending as much time with their family and go on to work at another startup or be a founder themselves.   Brian, on the other hand, doubled down on family and decided to work on the side project he started with his wife Meg.  

Brian and Meg are parents of three little girls.    They spent a lot of time thinking about who they would like their kids to grow up to be, which made them look back to their own childhoods.  What they realized was that the best memories they had as kids were spent outdoors.  They thought about ways they could make sure that their children would spend a lot of quality time getting out of the house.

What isn't surprising is that their plans for getting the kids outside became Tinkergarten, a distributed network of leaders providing outdoor learning experiences.  You see, Meg is a career educator, so play is never just play.  Play is an opportunity to learn and discover.  Brian, as a product manager, spent his whole career thinking about how to solve customer needs in a scalable way.  So as friends started bringing their kids to the play sessions that Brian and Meg created for their kids, it was inevitable that the conversation turned to creating a scalable model for it.

I give a lot of talks and always say "If you have a thing and you're not sure if your thing can be a thing, come talk to me."  That's exactly where Brian and Meg were when we first met.  Meg was very pregnant and they hadn't really done much work on a business model.  I introduced them to the founders of Zumba, chloe + isabel, and Zogsports--all companies that depended on creating scalable in person experiences, especially around training.  

If you ask me what companies in my portfolio have the biggest potential, Tinkergarten pops into my head.  I learned a lot about distributed models through my prior investment in chloe + isabel, and saw the potential of outdoor experiences as a business through Brooklyn's own Tough Mudder.   I fully believe that they are at the beginning of building a national and even global brand--the Boys and Girls Scouts of the next generation.  Plus, it's a great opportunity for additional income and is a positive addition to every community.  

I'm also excited to work with great co-investors like John Katzman, founder of Princeton Review who knows a thing or two about distributed edtech businesses, Mike Walsh from Structure, and Don Katz the founder of Audible.

One of my investors asked Meg what happens to Tinkergarten in the winter.

Her response? 

"We put coats on the kids." 

Here's to going out to play--in the mud, the snow, and sure, when it's sunny out too.

My Investment in Hungryroot: A Tasty Lesson in Products vs. Services

Brooklyn Bridge Ventures recently joined Lerer Hippeau Ventures, Crosslink Capital, and KarpReilly in Hungryroot's $2mm seed round.  The NYC based company makes ready-to-cook meals comprised of 100% organic, fresh-cut vegetable noodles paired with all-natural chef-designed sauces, toppings and optional pre-roasted proteins--and they're delicious.  The food has become a staple of my diet, which wasn't the case after trying various food delivery services out on the market. 

I took this pic and then I ate the food.  Mmm....zucchini pesto.

I took this pic and then I ate the food.  Mmm....zucchini pesto.

Services like Blue Apron and Plated don't sell you food.  They sell a service.  What you're paying for is for someone to help you cook--to do the recipe ideation, the shopping, the prep and the delivery close to when you're ready to cook a meal.  At the end of it, you're doing the cooking.

That works well if you cook on a regular and consistent basis, but that wasn't something I needed help with.  I'm half Italian and when I cook, I don't need any help.  I'm a great shopper and I can make a meal out of anything when I have the time.  These weren't services that I needed, nor did they fit into my busy, unpredictable lifestyle.  

What I need, and what I believe a lot of people need, is a product they can have available to them anytime and make in an instant when they don't have the time to cook, or just don't want to.  

Newfound appreciation for rutabaga.

Newfound appreciation for rutabaga.

Hungryroot meals have a 10 day shelf life.  So if you don't have any by Friday, no worries.  You can have them next week.  They do this through vertical integration and special packaging--and that's where the technical innovation comes in.  By the time you get your food, you've gotten it days in advance of when you'd get your food if you were ordering from a service that preps it for you, enabling it to last longer in your fridge.  To find another product with the same flexibility, for most people that means a frozen dinner or a can of soup--not exactly fresh and not exactly healthy.  

Hungryroot is going after that category--the packaged food category, with a product that takes about 7 minutes from package to mouth.  All you need is a pan and some olive oil.  Most people wouldn't describe that as cooking any more than they would warming up a can of soup.  

Because I always want them around, I order it on a subscription much like I order paper towels or soap on subscription via Amazon.  Just because something appears at your door regularly doesn't make it a service.  

I'm excited to be working with such great co-investors--and I'm hugely excited to finally be working with Ben McKean.  I first met Ben on January 29th, 2011 at an SLP mentoring session.  He was working on Village Vines, which became Savored.  We stayed in touch and reconnected around a blog post that I wrote in 2012 on falling in love with the problem and not getting attached to the solution.  Ben has a unique insight into the food space and that's why Hungryroot is resonating with so many customers--because he understands the problem.  

Getting to this deal early and being able to put down a fair term sheet was a function of the Brooklyn Bridge Ventures strategy of going deep in the NYC community and making super long term investments in relationship building over time.  

What the heck does a VC do all week anyway?

I have no idea.

I just know what I do--and what I saw partners at other firms I've worked at do.

That's one thing you have to realize about venture capital.  Every single firm is different.  How a partner at a firm spends their time is a function of the number of deals they do, the stage of the company, and their own personal style.  

As a single GP (a firm with one investment decision making professional), I get asked a lot of questions about how I manage my time considering the number of investments I make.  

So, I decided to actually take a look at past data and construct some average days and weekends to figure out where all the time went.  I'm going to go more in depth in future posts, but here's a little bit about what I came up with.

First off, here's what a normal four week period looks like for me:

I seem to lead a colorful life.

I seem to lead a colorful life.

There's some weirdness around seasonality.  I don't kayak in the winter, nor do I do long bike rides.  Actually, I don't do as many of these bike rides as I put down here.  It's more aspirational.  Running races and kayaking usually gets in the way.

And yes, I take every other Monday off.  I realized that I judge a lot of hackathons, pitch competitions and other various things on the weekends, and felt like I was losing at least 2 out of my 8 weekend days--so I gave myself back those days.  I usual get random chores done, or find that one friend who also has weird working hours.  

And here are the big takeaways I came up with:

I don't have a lot of dead time, mostly because I really really like what I do... so instead of watching TV, or doing not much of anything, I'm usually doing something.

There's a ton of times when I'm doing several things at once.  For example, adding in "softball" as something different than "friends" is silly because I've been on the same softball team for 10 years.  By now, we've got couples in and around the team, team babies, and we hangout when we're not playing softball, too.   Softball is also networking, though, because we have some entrepreneurs, another investor, and a left-handed female infielder who works at a venture bank and turns a double play as well as anyone in the league.

E-mail is networking, deal work, due diligence.  It's ever present and always on.  

One thing you won't find is a half day partner meeting--because I don't have partners.  There's a huge time advantage to being able to make decisions without scheduling your partners to come see a deal over multiple meetings.

In case you're curious what the deal funnel means for my time, I did that, too:

Seeing an opportunity could mean an e-mail, a calendar request, a pitch at a demo day, a news item, a LinkedIn position change--really anything that makes me conscious that a new startup might exist.

Out of those, I take about 150 new pitches a year--about 3 a week.  I think that's probably less than most early stage VCs take, but I think I've gotten pretty good at being decisive about what I'm *not* likely to invest in.

I can't think of any company where I made a mistake by not taking the meeting where I think if I had, I would have done the deal.  

Still, despite that harsh filter, roughly 80% of the meetings are pretty automatic turndowns, and I usually do it right there in the meeting.

Of the 30 or so I actually do some extended work on post the pitch, I'll probably wind up doing a little less than a third of those investments--or roughly 9 per year.

In two-thirds of those investments I'm in enough of a lead position where I'm acting as a board member, officially or otherwise.  

When you take into consideration how long I stay in that role (anywhere from 12-18 months) and the mortality rate of the companies, I usually have about 8 of those at any given time.  That also means that about 25-30 of my companies are alive at any given time, but on a steady state basis, I've handed off the bulk of that oversight work to larger investors down the line on the majority of them.

Back to the non-deal part of this, there's a serious advantage to being bald and able to wear a t-shirt and jeans to work.  I probably spend less time in front of a mirror than anyone I know.  

And if I wasn't spending so much time taking care of my physical self, I wouldn't be able to work and live the way I do.  I probably should have started with that.  Your body is the platform by which you build everything else on.

So how much time does all this actually equate to?  I took a stab at that, too, and suggest you do the same.  It's an interesting exercise.  There are weird parts, like board meetings being an hour a day.  They don't work that way--they're much more lumpy.  I try to stagger them to be one on Wednesday, one on Thursday.  That's the nice thing about leading most of these deals.  The board schedules revolve around you when you're the only one that actually asks for regular meetings.

Also, a note on sleep.  I'm a better sleeper than most people I know.  They say you're supposed to get 8 hours, but my time in bed is probably about 99% actual sleep.  I think a lot of people are awake for big parts of that 8 hours.  I don't really wake up at all, according to my Fitbit, usually falling asleep within minutes.  I feel great right up until the point when I'm ready for bed, too--so I feel like I've figured out what really works for me and try hard not to get less than that.  

Oh and you know what else I don't do.  I don't drink alcohol.  It's not a moral thing or any kind of problem.  It's just not something I'm interested in.  (I also seem to be very sensitive to the taste of it, too, so maybe it's kind of cheating.)  That means not a lot of time penciled in for hangovers or slowness the next day.

Here's what I came up with on actual times:

The nice thing about being a bike commuter is that carting myself around from meeting to meeting when I'm outside the office is also exercise.

And, try as I may, I couldn't figure out a way to get more than 24 hours in a day, no matter what formulas I used in the spreadsheet.  

The Quality You Never Hear Pitched When People Want in to Venture Capital

In my effort to rewrite the deck for my next fund, I've been spending a lot of time reflecting on what it is that I try to do.

A lot of people can say they work hard, or work smart, but that doesn't leave me off where I think I'm setting my goals.  I've been trying to figure out if there's any differentiation in how I do my job versus how other people might assume it gets done.

So I asked a few founders that I've worked with and they mentioned a word that struck me--because I've never heard any of the hordes of people in my inbox asking for internships, VC job recommendations and advice, etc. mention about themselves.


People always tell me how smart they are or how much experience they have--or why they have a passion for startups.  No one ever tells me how generous they are, or shows it. 

I went through eight years of Jesuit education, both at Regis High School and Fordham University--and one of the tenets they tried to convey was to be "Men and Women for Others".  

That's largely how I think about my job.  I think of venture capital as a service business.  

How can I leverage what I know to help people?

How can I leverage who I know to help people?

How can I spend more time being helpful and less time focused on the internal overhead of running a big firm?

At the end of the day, every chance I have to improve--to be of more use to the people I back, to build better relationships with other investors, I find that I can really just boil it down to one question:

How can I be more generous?  

It really does drive how I work.  

If I need to fill an open position for an iOS developer, I don't go around asking people for recommendations.  I ask, "What could I do for iOS developers so that a bunch of them show up in a place and I can create an opportunity for this company to get in front of them?"

If I want dealflow from other VCs, my first thought is, "How can I send more dealflow over to others?"  

Thinking about how you can offer more is a great way to be a better investor, and it gives people a reason to want to work with you over and above a check that clears.