Category: Business

The MBA Is Dead! (Long Live the MBA!)

(A huge thanks to my friend and the founder and CEO of Andie –  Melanie Travis who prompted me to finally write up my thoughts on this topic and was nice enough to let me guest post. – this something I have been only talking to people about over the years, and excited to share publicly below.)

I talk to a lot of folks at interesting crossroads in their careers and many times the topic of getting an MBA comes up.  I have formed a pretty strong opinion on this after being the host to many top tier MBA programs doing a “trek” to NYC to visit companies (thanks for visiting Foursquare!), interviewing many MBA candidates (pre, mid, and post), and from hiring folks (pre, mid, post) for both full time, part time, and internship roles. As with many topics since I have had this conversation with groups and strangers, I wanted to share my thoughts publicly to clarify and learn from others on this topic.


Let me start off by saying that I don’t have an MBA. I thought about it after college but never found that it made any sense to me. I also spent some years at USV, and Fred Wilson calls that time a practical MBA, and I tend to agree – he says

“I like to think of this two year stint as the USV MBA. We don’t issue diplomas but we pay salaries instead of charging tuition. You learn similar things but the cases are real time, not after the fact. And I would assert with a fair amount of pride that a USV Analyst stint on your resume is worth as much as a top tier MBA, maybe more. And the alumni network, while small, is fantastic.”

Given that caveat, I didn’t come to the decision lightly.  I spent a lot of time speaking to folks who went through various programs, some who loved them and some not.  I spoke to those looking to change careers and how programs helped them.  I spoke to many VC partners (most with MBAs) and got their opinions and advice.  I also have Phin Barnes of FRC to thank for getting me in touch with a Columbia MBA professor who took the time to chat with me about going through their program. When all my research was done, I formed my thesis, and started to share it around (including following the advice myself).  My last caveat is that I tend to spend time with people with a high risk tolerance that tend to be entrepreneurs.

My thesis is as follows: You should go and get an MBA if you do not have two out these three things:

  1. A Network (people)
  2. A Direction (career/life)
  3. A Business Education

If you have all 3, don’t go. If you have 2 out of 3 don’t go. If you have 1 out of 3 it might make sense to go.

My rationale is that you will be $180K (now more? Originally from 2010) in debt, out of the operating job market for 2 years, and still need to find something afterwards.

However, if you are searching for 2 out of these 3 I would encourage you to weigh the pros and cons and potentially go to get your MBA. It has to make sense for what you want to do – or better yet, what is NEXT after your MBA.

A few examples will help explain this further;

A Network:

Having a group of people that you can start a business with, find your first customers, simply enjoy being around, and can build your career with all contribute to your network. Some folks find that after college they go into roles that surround them with people they don’t like (or want to be like!) – and they want to “pivot” their careers.  Let me be the first to say that this is totally fine and I commend you for wanting to make a change.  I have seen this happen with folks in fine fields that are just not a fit for them such as finance, banking, medicine, law, etc…

The people you connect with during an MBA program can be instrumental in what you do next.  In fact many of the founders I know met their co-founders while in a program or in the surrounding companies and internships they were involved in.

A Direction:

Knowing what you want to do when you grow up is hard.  Everybody seems to ask this question, yet nobody really seems to have the answer.  Knowing that you want to go down the road of entrepreneurship is great – but then you have to learn the skills either on the job or in a structured program.  Going through the new entrepreneurship tracks at top tier programs is a great way to find this direction (or discover it’s NOT for you!).  While similar to the above roles that I have seem people come out of, some folks just don’t know what they want to do next and this 2 year program can give you the space you need to explore. Again, this is a high cost way to figure it out but nonetheless it can help.

A Business Education

I have met folks who want to start a business, but perhaps didn’t get the education necessary or have the business skills to do so.  Perhaps they studied something else in school, went for other reasons, or don’t have the business background they need.  This is a great reason to complete and “finish” your education and learn about these parts of business. Some good examples of this are folks that study different topics in school, or think they are going down a different path (spoiler alert: that is perfectly fine to change your mind later!).

While others still want to learn about the business side of the world + grow their network to find the right people to work with.  They know they want to work in a sector, start a co, join a startup, etc.. but not sure how to get that done.  They have a great business education but need a network and a direction = potentially go!

My approach may not work for all but it has served me well.  Personally, I built up a great network and knew what I wanted to do – direction (work with/in/around startups), however didn’t have the business education but thought I got some pretty great exposure to real life case studies while at Union Square Ventures = Don’t go!

Today I have a great hybrid role between investing and operating at Expa. It’s a great place that combines two things I love, and overlaps nicely with where I want to be spending my time.

Ultimately this has provided a helpful framework for many folks to make a decision and potentially save a lot of time and money.  I would love to hear from those who have chosen the path of an MBA and those who have not.


Turning coffee into Bitcoin

I few months ago I had to lower my coffee consumption and was struggling to find the best way to “force” myself to do so. Nothing major prompted the change, but wanted a catalyst to really stop. I have been following Bitcoin and other cryptocurrency for awhile, and thought I would use this as a way to get more. In looking at all my options I figured out a way to turn coffee into Bitcoin…sort of.

To really motivate myself I figured I would lower my costs by stopping purchasing coffee every day (easy!) but then divert funds into purchasing Bitcoin dollar cost averaging into the currency (hard!). This prompted me to start looking for a recurring purchase into a cryptocurrency that was liquid and growing and quickly settled on BTC. They say that using Bitcoin is key to its success and by purchase more and forcing a use case, I can help the overall ecosystem better. Having more will create usage, which will create value in the network, which will drive more use and hopefully the ecosystem as a whole.

Enter Coinbase (they have a referral program!) which is a great solution for setting up a reoccurring payment buy in platform. Below is what I setup to

The trick to dollar cost averaging into more Bitcoin was setting up a simple reoccurring transaction every week. This would prevent me from making a few coffee purchases (let’s be honest — about 1 in some places in NYC) and built my BTC balance. While not the most economical approach, Coinbase has their fee structure, it has really worked. I have been doing this for the past 6–9 months and it has worked well. Inadvertently I have lowered my spending habits too, being in less stores and coffee shops which evens out the fees a bit.

The question of course is where to store things, and I may wait for another post for that. In the interim BTC/USD has been trending in the right direction — although technically I shouldn’t care as I am now better equipped to weather a downturn.

While I am not quite there yet, I was partly inspired by my friend Steve

I think it is entirely possible that the value generated from purchases will yield a result, I think it’s far more likely that I will spend it first thus helping the ecosystem as a whole.

I have always been a tinkerer, and to really understand something you need to use it — this project has given me a great solution to coffee consumption and a BTC balance to spend on things.

Putting out the biggest fires

I am usually a very regimented person, and crave process and structure. Some would even say too black and white, as I need to allow for some grey areas and unknowns. I agree with this feedback and take it to heart. It wasn’t until I started to build the inside sales team at Foursquare that I really saw it as a something to work on and something to watch out for that I realized its importance. To help with this I use an expression that I first heard from my former colleague and friend Dave Greenberger, now head of sales at Splash, which is; “put out the biggest fires”.

Dave came onboard to help manage the inside sales team we were building at Foursquare and there was a lot to do.  During his interview process he brought up his methodology to handling things like; recruiting, hiring, churn, customer service, technology woes, everything really…
At first I was taken back as it went against my need to prepare and plan, but I knew my approach also wasn’t working. I went with my gut that this was the right approach – and seeing it in action it was.
Putting out the biggest fires has become a startup mantra for me because it goes well beyond inside sales. It is a more tactical version of the cliche of building a startup “it’s like jumping off a cliff and building a plane on the way down” This phrase  is almost too glamorous and non-genuine as it doesn’t get at the heart of the matter. It doesn’t capture the actual day to day maneuvering that is necessary.
Putting out the largest fires is embracing the fact that there are fires in the first place. Everything is not perfect, and that is perfectly fine.  It is probably half the reason most people join a new startup in the first place.  Any attempt to sweep problems under the rug and hide from them isn’t a good approach, and this gets them out in the open.
You can’t prevent all the turmoil, but you can influence how you deal with it. This was WHEN someone comes with an issue (not if) you can process and fix vs waste time and energy on WHY. Doing a Post Mortem and placing blame are not helpful in the moment. They can help after, but if you are only focused on the end and the potential bad outcomes, you are not adequately preparing for reality. Things happen. Stuff will break. Fires will burn. By taking on the “put out the biggest fires” you are stating that you know things will go wrong but you are willing to do something about it.
So thanks Dave for making this part of my startup strategy book. As I work with teams and companies more and more this advice comes up, and writing it all down gives me a chance to reference it in the future and check myself with folks who have opposing views. Let me know if you have seen this work, or have a different approach.

Next after next

One of my favorite interview questions is “what is next for you after this role?” Or put another way “what is next after next?”


I added it to my list of go-to questions for almost every role as it gives me insight and information into a candidate beyond anything else I have asked before.

Accepting that most folks are not going to join your company and retire after 40 years is a healthy way to have the rapid career change conversation that is a sticking point for so many. Embracing that someone is not going to stick around forever is a good thing. The hope is they are going to be around and give you their all for 2-4 year(this is a good outcome in my book). Anything longer and their role will probably change anyway. Anything shorter and there is some other issue.

Hearing from candidates about what is next is also just plain interesting. Some folks talk about what they “really” want to be doing and I have heard things such as; run product, start my own company, be an investor, go to grad school, write a book, become a professional singer, run a sales team, pivot their career and start over, break into startups, go to grad school the list goes on and on. Some folks are about finding a stepping stone role. Some people want stability. In the words of Mark Suster some folks want to learn and others earn – and this is great advice.  I like to get at the root of where they are coming from from asking this question. Giving them a platform to talk about their own story arc and where it’s going is a refreshing way to get at what motivates them.

If you end up hiring the candidate, this is a great thing to discuss in 1:1s and reviews (not every time but as a macro goal). Questions like; are you learning what you want to learn towards your next gig? Is the work you have challenging you to get to your next role? Do you have the skills you need today to do this next level job? Knowing where someone wants to get to later on (what is actually next) can be a way of actually gut checking the answers to these questions.  Sure, someone needs to know how to do their job within your org. but if they are acquiring skills that can help them in their career they will do a better job and be more invested in the results.  These results are going to be what they talk about in interviews, put on their CV and LinkedIn, and reference later on.  If you can connect the goals of the individual with the macro goals of your company you can ensure you have someone that is truly dedicated to mastering their job.

It’s also not about leaving a company or job. I have spoken to lots of candidates who divulge that they actually want to be in a different department or role within the company and they see this as a way in. For small companies I see this as more of an issue, but larger co’s I have no issue. People also talk about role models in the current company wishing to aspire to be like them (or be them if/when they leave).  Having this conversation early can ensure you don’t end up in a bad place during a review period.

So next time you go into an interview ask “what’s next after next?” and let me know how it goes.

It’s the questions not the answers

Slack recently had an outage, which happens to every company, and people noticed on Twitter – wow what a reaction!

I was reminded a lesson I learned from Brad Burnham while I was at Union Square Ventures; it’s the questions and conversations that are important, not the answers. 

This came about from Brad as my colleague Andrew Parker and I were arguing over whether or not we should be checking in to a place on Foursquare.  We had gotten takeout/delivery (I can’t remember which). Following the “rules” you should check into places that you go (hey, this was before Swarm ok?). However we definitely purchased something from the restaurant, so didn’t that warrant letting them know? There were clear benefits; sharing on Twitter/Facebook, letting the business know, training the Foursquare system. There were also plenty of challenges; the location services may count this check in as “cheating” given we were so far away, we weren’t technically “there” if someone came looking (this happened a lot in the early days).

The list for both sides goes on. I think this is where Brad jumped in and stated that it didn’t really matter who was right or wrong – he was much more interested that the discussion was taking place. He said that many times it’s not about having clear rules for digital games, but rather the constructs make people think, and question – the discussion is the most important.

This brings me back to Slack; watching the reaction of people was fascinating. It didn’t matter if it was an outage, a hack, an AWS problem (I don’t even know if they are on Amazon) but rather that people noticed. Being in the zeitgeist vs having hype are two totally different things. This downtime brought companies to their knees, and people couldn’t work without it. That’s the most important thing to notice. I am sure we will get an explanation and post mortem, but people will still be using Slack. It reminds me also of the Twitter outages of the early days – only now there is a place to complain! (On Twitter – how meta)

As I look at companies both through my operator and investor lens, this discussion is the strongest signal to Slack dominance and usage across organizations and companies.   

Many see the valuation and argue, I see the discussion and see value.

To build a network, first help a network

I was talking to a friend a couple of weeks ago who wanted to break into and meet people within a specific vertical of startup tech companies. His approach was to feign interest in their offering and take a pitch from a salesperson. The thinking being that although there was zero chance of him becoming a customer, he could get time with a rep, learn about the offering and “build a network”.  I told him this wasn’t a good use of his time, and certainly not a good use of their time. The founding premise of the interaction would tarnish the reason for getting together in the first place.networking

I then shared a lesson my mother taught me about friendship which is; “to have friends, you have to first be a friend”. My professional version of this is the title of this blog post; to build a network, you have to help a network. You see it’s less about getting on a persons calendar for coffee or a meeting and more about finding out what you can do to help them.

A lot of people reach out for “informational interviews” or to “pick your brain” on stuff and the value exchange is lopsided from the start.  I hear of many of my friends/colleagues/CEO’s who simply decline by not answering.  This doesn’t help either side as the people writing the emails just figure they have to send more, be more persistent, or add more people to the top of their funnel.  This is a mistake, and instead they should think about the what I call the coffee equation which is putting in more time/energy into the ask before asking for something in return. You should give more first if you ask someone to have coffee so they know the agenda and feel good about spending the time.

Going back to the macro point, many people want to build a strong network.  To do this first by helping others you will not only understand their pain and problems first, but be someone that the person doesn’t mind connecting with in the future – especially after knowing you understand their world view and potentially help solve some of their problems.

To build your network, first help a network.

Personal Finance Tracking Apps

I recently read the NYTimes writeup of a ton of personal finance tracking apps and wanted to share my own thoughts.PiggyBank

My conclusion is that there are a ton of apps out there, all take a ton of work, and none do the job quite right.

This is a big opportunity as these apps can look at your personal spending habits, see SKU level data, and piece together very interesting demographics about a person.  There are lots of advertising opportunities surrounding this data, up selling to other products, and of course managing the funds someone has.

Looking at my “Finance” apps folder it seems I use a hybrid combination today of Level, Mint, BillGuard, Venmo, PayPal, and SplitWise.  I also use all my proprietary card and account apps.  I have tried to put together a monthly budget ahead of time, as well as look back using some of the smarter filters in the services listed above and I still do not have a great view into the things I want to see.


Here are the areas that I think need the most work in personal finance:


I have a few side projects/businesses that generate revenue that make it seem like I am making more than I really am.  I keep everything separated out neatly for tax and accounting purposes, but the overlap causes confusion.  I have re-classified many transactions but it still causes some headaches.


My wife and I manage everything together, but transferring money between accounts and cards gets confusing.  Mint comes closest to solving the need for transparency here, but one large transfer can throw off the entire system.  I have not seen a great solution for couples to manager their personal finances to date.  I think most of the solutions are focussed on tracking your daily, weekly, and monthly dollars going in and out but not segmenting them up very well.


The budget feature in Mint just feels broken.  Each app throws out suggestions or calculations based on what it thinks will be left at the end of a month, but they are far from correct.  The most success I have had is self budgeting into a separate account each month towards a big purchase.


Tied to the entrepreneurship bit above, there is no good way to classify certain transactions.  An example would be a tax refund, a cash outlay for something or payments to a friend.  Venmo payments throw off any chance I have at budgeting correctly as it looks like I have income and losses galore when its really just a transaction towards a weekend trip or a dinner.  There must be a better way to classify something towards a life event vs. “Income”.

There are probably others, but given some recent discussions I have had I wanted to get these down.

What are you using to solve your budget issues and what systems are working?

“Where did my Google Drive Go?” – Trouble with Google UX

Sometime last year Google changed the way folks access the “apps” within Gmail and Google Apps for Business accounts.  My summary of the change; everything now takes two clicks instead of one.  The official response shows the feature, and the product forums tell us “…simpler design lets you focus on your in product experience but switch to other Google products when you need to.”

Here is the new design decision that has resulted in folks actually asking me what happened to Google Drive.

Screenshot 2014-01-19 10.09.31

If you dive into the feedback from users and customers its almost unanimous too; why would you change it to two clicks instead of one?  I have heard this from my team internally, and many other friends as well.  Folks have come to me asking “why did we remove the links?” as if it were a corporate decision.

Others gave up on using Drive because they could no longer find the link.  If a design decision yields lower usage of a product, I believe you should change it back.  Of course I do not have any data to backup my claim that usage is lower, but I know Google collects and analyzes such data.

Gmail is also making other changes to the previous default way things are handled.  Fred recently highlighted the changes with regard to attachments within gmail noting that the default to “open in drive” is now gone.  I also don’t love this change, but you can still preview the contents of the email by clicking the title.  This “lightbox” approach is not great for me as I am distracted by the email happenings going on behind the document.  Perhaps this is just a temporary moment in time between the old way and the new, but almost 6 mos. in I still want the old way back.

I use a lot of Google products.  I use Gmail personally, and Google Apps professionally, and pay for extra storage.  I only caveat with this information as I believe in the platform.  I want things to work better.  I am heavily invested in the network effects of Google.  As I have said before, once a behavior stream is happening its hard to change.

However all these negative changes make it a little easier to look at other tools and solutions instead of Google, whereas before I would not even entertain giving them a chance.



Some thoughts on Calendars and Meetings

A lot of companies are trying to “solve” calendars.

There are many startups that are building calendar apps, desktop apps, and combinations of the two.  Some even try to also manage your to-do list. Integrated features like knowing background information, lateness notifications, and notes on important details about people or places – all part of the race to “own” your calendar.

The goal of course is that you are weened off of the standard/default calendar that comes with your phone/tablet/computer/OS and you use their app instead. This of course is a great lock-in for the app makers for it increases the switching costs to another calendar or service.  If you are tied to the “extra” features of a calendar like to-dos, notes, cumulative info – it can be hard to switch to something else.

I believe a missing thing they should be going after is solving scheduling. Whether it be meetings, calls, reserving times that work, or anything else you need to do involving blocking time off in your schedule.  It has been said many times elsewhere, but the best way to see someones priorities is to look at their calendar.  Its almost like a to-do list with your time and some even say that if its not scheduled in your calendar its not important.  Blocked time in your calendar visually shows your priorities.

Most calendar apps miss showing the simplest thing for me – showing free time on a day view. The benefit of this for me is that I am constantly adding/removing meetings and things on the fly and need to know the windows of time I have available.  Either checking while on the phone, in a discussion, or in real time trying to reschedule something viewing the free time is critical.

I am using the Google calendar system of record and pushing that to my iOS view.  This does make things easier and in some ways it means that Google “owns” my calendar.  I have heard that this also means switching back to native Android would be that much easier.

Knowing that this free time view is crucial, I always look to see which apps provide it; either on the desktop or mobile. Perhaps it is just not as important to others but many simply do not have this view built in.  All shows you when things are booked, but not when you have time.

My workflow is always to open my email in the morning, open another tab with my calendar, then dual wield between the two all day. Through the rats nest of Google Calendar settings, I have figured out a way to manage and edit both my work and personal calendar – no small feat.  It means that I can view my personal and professional calendars together and still invite people in both worlds to events.  I have reached a point where if I do not put something on my calendar I may forget about it, so I try to put every meeting in it.

Calendar App Wishlist

  • Desktop app – Having a calendar open in another instance of Chrome is a pain.  Opening the two and switching between them all day seems like a waste, but without the free time view, I don’t see another way.
  • Mobile app – syncs flawlessly with work + personal and shows free time view
  • Background info – Rapportive style background on people.  Refresh does this today, but its background on the people and secondary to the Calendar itself, not a replacement
  • Simple sharing\editing granting permissions – As mentioned above Google allows this, but its a nightmare of settings and sharing functionality
  • Default meetings times = 30 minutes.  Simple enough request, but Google Calendars makes this fixed to 60 mins. (Ideally I would get to choose the time for the default meeting)
  • Weather/Foursquare Location/Distance to travel <–easy metadata to make any appointment that much easier
  • Future proofing; interior location monitor if I am not where I am supposed to be, notify someone automatically that I will be late, ping me if I am not moving towards my next meeting, sync up latest emails with that person into cal., oh and lasers

My calendar workflow for meetings

1. Setting up a meeting via email

The best add-on I have found for managing meeting requests without all the back and forth is Boomerang Calendar (free!).  It automatically lets you click times that are open (in 30 minute intervals!) and inserts them into an email to someone.  Its one of the biggest time savers possible, and avoids a ton of back and forth that usually happens with scheduling.  I wrote about appointment setting etiquette, but I respect the fact that everybody is different.  I get multiple “can you meet this week?” emails often and always follow my own rules to respond back with 3 times/3 dates.

2. Logistics

Picking a time or place can be cumbersome, so I always throw out a dial in to the group.  I use TextExpander (paid but worth it) to have my info ready, and this way I always know my own dial info and code.  This way no matter where I am, I know I can dial into the meeting with the right info.  I used to use but have found the latency is just not worth the broken conversations.  Investing in a rock solid conference line is worth it.

Pro Tip: You can program in your own conference call info into favorites, program in pauses with “,”‘s and have it automatically dial you in, enter your passcode, as well as the admin code.  This probably saves me the most time each week next to Boomerang Cal.  To put it another way, I can click “Conference Line” and my phone will automatically deal with the prompts/codes/admin code for me and get me dialed in fast.

3. Locations

When meeting someone in person outside my office, its best to know/pick a spot nearby.  Perhaps its just a personal peeve, but going back and forth on a place is hardly worth 4 emails – I cut to the chase and offer up nearby coffee shop/diner/other.  I am clearly biased, but using Foursquare is honestly the best way to find a place that accommodates meetings.  Lots of people leave great tips at coffee shops letting me know whether its good or not.  Here is a great tip at Grey Dog in SOHO saying exactly what you want to find for a good location.

This post is a bit of a rant, but I am trying to get back into the drivers seat of writing more blog posts in 2014 🙂

Can’t find a mentor? Become one

In Sheryl Sandberg’s book Lean In she devotes a chapter to mentorship and how many people approach her at the end of a talk or conference asking her (without a prior relationship) to be their mentor.  She admits this is an awkward situation, and obviously cannot mentor all these individuals.  I have heard this happening to others and it’s not an easy situation. While I don’t have a good answer for those being asked, I think it’s important for those doing the asking to understand what they are after.

Looking for a mentor can sometimes be fruitless because most mentor and mentee relationships form organically and sometimes never get formalized. Many people point to their mentors as keys to their success, helping them navigate tough times so others try to emulate the same situation.  You can’t simply snap your fingers and find a mentor. It’s a relationship that has to be formed over time, through communication, questions, working together, and many other means.

However this does not mean that you can’t flip the tables and learn something about yourself along the way. If you are really on the hunt for advice, try finding someone who needs YOUR help.  Chances are that there is someone else, without your life experience, that could benefit from what you have done.

I believe anyone can apply their life lessons to someone else either in the same position or about to be in that position.  For example, a recent college grad may be looking for a mentor in the field they want to go into. They may find a hard time getting folks to return emails and calls and get discouraged. This is when they may think “without experience I am doomed!” When in reality they have plenty. Going back and talking to a new freshmen coming into college about their experience can be a way of reinforcing everything they themselves actually know. They can actually mentor someone else.  Being out of college even a year and applying to jobs is enough experience to speak to a graduating senior to give them perspective on what they are about to embark into.  This may not be a position everyone is in, but it serves as a good example I often use.

Another example is a current/recent MBA looking for a CEO/Founder mentor. This is a dream scenario I hear a lot. Instead of getting discouraged sending emails that go unanswered, they could spend time working with an entrepreneurship group honing the skills they learned getting an MBA.  Finding Meetups with like-minded people and putting your skills and expertise to work just takes a little effort.  You may not be paired up with the CEO of a thriving company, but you can surround yourself with people solving problems you are interested in.  This can often lead to a peer group that is ultimately more helpful.

The truth is that people need help and mentorship at all levels. It’s not about the job title of the person, it’s about genuinely helping people. It would be great if a big CEO would take you under their wing, but it’s not the only positive outcome.

Take action by helping someone else. Start small and answer a question or suggest a solution. Over time you might find yourself being a resource for that person.  I have found that being a mentor is a great experience and solidifies my own knowledge topics  while teaching someone else.

In the absence of finding a mentor, become one.