My Learnings from The Book of Joy

This past summer a good friend of mine bought me a copy of “The Book of Joy.”  In the last year I’d been getting into meditation/spirituality, and his wife had loved it.

While the book isn’t very long, it did take me a long time to read it for the simple reason that there is SO MUCH wisdom sprinkled throughout.   For those that don’t know, this book is basically a summary of a week of conversation between the Dalai Lama and Desmond Tutu.  It outlines many of their core philosophies.

There are a ton of great tidbits in this book for anyone with an open mind, and I highly suggest you go buy it if you’re at all curious.

I knew it’d be a worthwhile exercise for my own self to codify some (I can’t stress ‘some’ enough – this book is full of interesting and useful wisdom) of the key lessons that I took away, and thought “why not write them up on that blog I never post to!”

So, here are a few of the lessons I took away:

  • “The purpose of life is to find happiness” – The Dalai Lama says this in the opening part of the week, and I completely agree.  Of course, finding and pursuing happiness are quite different and will lead to divergent outcomes.  As is mentioned later in the book, happiness is a byproduct of generosity, compassion, self love, and a host of other worthy pursuits.  Pursuing it directly usually ends in distraction and a focus on things like fast cars or big boats.
  • Compassion = Happiness – Do you ever have one of those days where you strike up a genuine conversation with a stranger, or get to help out someone in need?  As the book says “If you develop a strong sense of concern for the well-being of others, this will make you happy in the morning, even before coffee.”  This is very true, and you can lean test it by smiling and saying hello to each person you meet with today – I guarantee you’ll notice the change in yourself.  Of course, you can supercharge your effort through generosity.
  • A grateful mind breeds happiness – Having a bad day?  Think of something you’re truly grateful for and focus on it.  Maybe it’s as trivial as how warm your coffee is, or maybe it’s something as important as your health.  Focusing on things we’re grateful for is transformative, and a worthwhile daily practice.
  • We’re all people – This is very related to the compassion point, but I wanted to write down a key consideration made throughout the book around the negative side of personal interactions.  Ever have a boss that is horrible, or have a run in with a bully?  Realistically, these people are critical because they see the world as critical, or aggressive because they are fragile.  Forgiveness and empathy, even to people who “don’t deserve it” leads to happiness.  Side note: I’ll admit it, I can hold grudges…but letting them go feels so much better than ruminating (with the exception of when I’m trying to beat a 3 mile time and need some extra adrenaline for that final push).
  • Stress and hardship are just a part of life – According to the book, stress is actually key to our development in utero (disclaimer:  I’m no doctor).  We can all agree that it’d be crazy not to recognize the amazing role that hardship and failure play in the evolution of us as individuals.  So, try to see the bright side of your next challenge, and realize that every human on earth has to go through something similar in their lives (easier said that done!).  Apparently, the first noble truth of Buddhism is that life is full of suffering.  If you need some extra inspiration here, I highly recommend Viktor Frankel’s Man’s Search for Meaning.
  • It ain’t all fluff  – A lot of the above sounds like something a non analytical thinker would believe in, or what you may simply learn at Kindergarten (and what’s wrong with that???).  However, nothing could be further from the truth.  Following the teachings laid out in this book will actually make you happier, allow you to think clearer, and live a more “productive” life.  Beyond my own experience,  you can see that these teachings align with how humans came to be through the evolution of our species.  For example, building meaningful relationships with others is a sure fire way to be happy, which makes sense as that’s how we used to (and still do) get stuff done in society.  In fact, the book is sprinkled with actual scientific studies that detail things like lowered hypertension in people who gave away money…just in case you’re a skeptic and need some data along with the wise words 🙂

One fun thought experiment is to think about the various things future generations will know as truth that we can’t see right now.  For example, we now look back at history and think “how could they not know smoking was bad for them?” or “how could anyone not see the CDO market was a house of cards that posed a major systemic risk to the economy?”  Meditation is a great way to think more clearly about the question of what we just aren’t understanding now…and, perhaps its future adoption will be another answer to this thought experiment.

The Morality of Personal Branding

For the majority of my life, I’ve been mediocre at best when it comes to marketing myself.  This is true in the business and personal realms.  In fact, there was a time when I took pride in being mostly steak with very little sizzle.

However, I’ve slowly realized that building a personal brand has massive benefits in helping accomplish your goals.  I know people who are pretty much average in their talents who’ve been able to accomplish a lot simply because they were truly great at marketing themselves.

What is personal branding

Just to be clear, personal branding is any attempt to dress up your own accomplishments.  This can take the form of a highly manicured LinkedIn Profile, a personal blog (ahem), smart-sounding language you use to describe stuff, etc.

Why I hated personal branding

The reason I took pride in my lack of sizzle is because at my core, I think that  ideas, talents, etc should be evaluated in an objective and analytical manner that rewards that which is truly great.

I hate it when entrepreneurs spend days honing their pitch before raising capital.  Shouldn’t VCs simply be judging their business’s merits based on a frank conversation that answers the key questions in the most honest, and intellectually honest way?

There are a few million other examples: dating, sales, introducing yourself to a stranger.  These interactions can all be changed and framed in drastically different ways through the way someone “brands” themselves.

The reality – it matters

I mentioned a few people I know who’ve done well because of their personal branding.  Ok, so I won’t mention any names here, but there are smart people I know who’ve made >$10 million MOSTLY on the backs of their personal branding efforts, and average people who’ve made $>1 million.  Those are pretty conservative numbers.

Think about the person in your office who does a phenomenal job of making sure the boss knows when they did a good job, introduces themselves to the CEO to get on their radar, and gets promoted faster as a result.  Now, think about an entrepreneur who turns a personal mystique into a million dollar contract, despite their product.  Yup, this stuff matters A LOT.

What’s more – it takes a VERY long time for most people to figure out if the emperor is wearing any clothes or not.  Marketing of products is so ubiquitous for a reason, this is how companies effectively hack our brains into buying products.  The same can be done at a personal level.

The moral question

Ok, so who cares if your colleague gets promoted 6 months before they should?  We live in a capitalist society where you should get yours, within the realm of the law, right?

Sure, but where is the line?  At the extreme, “false advertising” here means that someone is a con artist who defrauds people of money.  One step below is the person (probably entrepreneur) who grossly over inflates their past accomplishments, relationships, etc to get economic benefit.  I’ve run into this a lot as I’ve started my own business, both watching others and from people overselling themselves in order to get equity in our company, or cash.  Fun times.

We all need to do our own diligence on the characters that we run into in life, but I’d also like to think that we are all good actors in the world that have empathy for others.

At the risk of getting very long winded, I believe that the personal branders out there need to make sure the image and narrative they’re putting forth are in line with reality, and not aspirational – or down right false!

It’s actually not all that bad!

Before you call me a hypocrite for having a personal blog ( I don’t even have a favicon, c’mon), professional LinkedIn headshot, etc…please let me state that my perspective has changed drastically since I started my career.

Beyond the most basic of “branding” (you should probably wear deodorant, brush your teeth, etc), it just plain makes sense to market oneself.  Realistically, we all use appearance, reputation, etc to evaluate people and figure out if we want to do business with them, or be their friend.  With that in mind, you should take the basic steps to put your best foot forward.

The important key is to remain authentic, and self aware.  A week back, I heard someone in my network talking about how they modeled their personal brand off of the “heel” character type in pro wrestling.  I actually admired that.  They aren’t pretending this is their true self (even if they are kind of pretending this is their true self).  And, they’d done this in a very intentional way in order to differentiate themselves in a market full of nice people.

From a personal standpoint, you’d be kind of crazy not to put in at least the baseline efforts.  Just please don’t exaggerate because then it makes the whole personal branding this feel really icky.

A “Get To” Perspective

You know those times in life when you have to do something you really don’t want to?  Maybe it’s some seemingly irrelevant analysis in excel, or a 5 hour drive with someone you’re not super fond of.

We all have lots of things in our lives that aren’t very fun.  And, in entrepreneurship, that is probably even more true.  Many times founders are the ones doing the grunt work up until the company hits a certain point.  This could mean doing data entry for a lead gen project, or washing the dishes someone left in the sink.  The glamorous lives of startups!

In fact, a lot of a founder’s day is stuff they have to do.  Write an eBook, send a newsletter, do a demo, follow up with all the people you met at the event last night, check in on an existing customer…the list goes on and on.  And, honestly, sometimes it’s super overwhelming.  Sometimes you’re thinking to yourself “there are so many things I HAVE TO DO!”

A “Get to” Attitude

If I was smart, the title of this article would be “the one change that will make you so much happier at work.”  I really think with a slight change in perception, things get a bit more fun and exciting.

Instead of a “I have to do this” mentality, you should be adopting an “I get to” do this attitude!  You don’t HAVE to do that excel analysis, you GET to do it and are now more facile with excel, gained insights into whether or not it’s worth it to do the analysis, got to challenge yourself a bit (even if it’s just to see how fast you can do it), etc.

Adopting a grateful mindset is a proven way to be more happy.  If you don’t think this is true, I challenge you to spend 2 full minutes right now thinking about the things you are grateful for and really think about them.  Even if it’s as simple as “I’m so grateful for a warm cup of coffee” or “I love how this pair of sweatpants feels” it will make you happier almost instantly.

The Sports Analogy

I remember watching an interview with Charlie Rose and Gary Player a while back.  Gary is an incredible golfer and Charlie asked him why he was so good.  Gary responded that he enjoys the challenge of being in a bad situation.

This means that when Gary hits his ball into a bunker, his attitude is not “damnit, now I have to figure out how to get this ball out of the bunker and not overshoot the green or else I’m going to lose this tournament!”  No, his attitude is something more like “Ok, now I get to challenge myself.  I get to figure out this problem, and get better at figuring out these sorts of problems from here on out.”

Startup Life

Obviously, this “get to” attitude is tough to internalize.  This is especially true if you’re working 100 hours a week as a resident, or an ibanker, or whatever.  It’s also tough as an entrepreneur who’s focused so closely on building a company while not straying too close to the sun.

However, I think it’s an awesome way to get over the nature of work – which is that a lot of it kind of sucks and no one wants to really do the hard things.  But that right there is a reason to do them – you’re doing the things no one else wants to do, and therefore are gaining an advantage on your competition.  Or, maybe your rational is that you get to provide for your family, or get to gain a new skill, or get to live in the first world where we have so many advantages.

Whatever you do with your days – whether it’s golf or entrepreneurship – try out a “get to” attitude, especially when you find yourself overwhelmed with what you have to do.  I hope it brings you more satisfaction and happiness in whatever it is you’re pursuing.

As a disclaimer, someone in my travels framed this “get to” attitude for me – it’s how they try to live their life.  I totally forget who and in what context, but they deserve any credit for this idea which has stayed in my brain ever since.

Videos on Working in Venture Capital Pre-MBA

I made these videos a few years ago about my experience working in a pre-MBA role in VC at Bessemer.  They were originally hosted on  But, since that site doesn’t exist anymore, I wanted to post them here as I get 2-3 emails a month from random people asking “where are those VC videos?!”

I haven’t viewed them recently out of embarrassment :).  But, I’m hoping that people will find them useful and so am happy to have them still exist on the internets, enjoy!

Parsing Advice as an Entrepreneur

Understanding what’s true and what’s not in startup land is one of the most difficult challenges that I’ve dealt with as an entrepreneur. I’m not saying there is a lot of purposely false information being disseminated. More, I’m saying that a lot of advice, stories, etc that you hear are just wrong.

In fact, your better advisors will tell you that “90% of what I say is wrong, and it’s your job to understand the 10% that is relevant and should be acted upon.” Of course, your BEST advisors will tell you things that are 80% true as they understand you and your business. That makes your job a lot easier.

It takes a village

It’s very true that without the help of those in your business community, your company simply won’t get off the ground. Some help comes in the form of early customers willing to take a risk. Other help is in the form of capital from angels. And, much of this help is in the form of advice and connections from leaders in the community – or someone who just happens to know something specialized and useful.

One of the things that makes Silicon Valley an amazingly fertile place to start a company is that it has these groups of people in spades. And, they’re willing to help.

However, while advice can be helpful, there is so much bad advice out there! And, it truly is your job as an entrepreneur to figure out what is right (as best you can).

Here is some of my advice (hehe) on how to parse this information, and warning signs to look out for.

Incentives matter

As Charlie Munger likes to point out, personal incentives matter, a lot. If someone has an equity stake in your business, they may be pushing you to go big or go home, even if it’s too early to pour gas on the fire. If someone owns a blog/conference/whatever they may want you to advertise there. Be careful if they’re getting money out of that, even if it seems like a good idea and you trust the person.

Don’t believe the hype

Once in a while you get connected to someone who’s a real startup luminary. They sold their last company for a lot of money, or work at some big VC fund. Many times these people have insane degrees, and you’ve read about them in the latest Forbes list of XX under XX.

Be careful. Just because someone has the right credential, doesn’t mean that they understand your space, your tactics, the problems you’re dealing with right now, or the way you want to build a company. Besides, most people who have large personal brands got that way by working on them, not necessarily by doing anything impressive.

People learn the wrong lessons

Many times entrepreneurs or VCs share the tactic that they believe helped their last company get off the ground and relate it to your business. They know this is a proven method that works, and so you should do it too (I’m totally guilty of telling everyone I know to go to bschool, btw).

The problem is that what worked for a B2C business 3 years ago doesn’t work for a B2B business today, or even a B2C business. It COULD, but be very weary of people who tell you to do what they did simply because that’s what they know. Pick apart why this time may be different, and try to have an intellectual conversation with them.


Many people who give advice just like to give advice for their own sense of self worth. I have a running joke with my co-founder about this one guy who always says he’ll do me a favor and make time on his calendar for us. He never does, and we really don’t want the time anyways. He simply wants to give advice for the sake of being heard, which is another problem with personal brand builder types.

This is the type of person who won’t listen to you, and who’ll just talk about themselves for an hour and then expect a thank you for wasting your time.

You’re always wrong and you’re always right

In these conversations, you’ll get told you’re wrong and right by different impressive people for the same conclusion or tactic. That’s part of the problem here. This advice stuff is all just another datapoint in your way forward.

My advice: trust your gut, and don’t be afraid to go against the grain. If someone says you’re wrong, understand why. Same with someone who thinks you’re right. Are they really hearing you? Do they understand the details of what you’re saying? What assumptions are they making and what information are they missing?

For example, I might tell someone I’m going to use inside sales to sell my product. Some people don’t know what inside sales means, some people will remember a blog post they read where you have to have a certain ACV to do inside sales, and some will build out a strategy in their head around what their inside sales strategy for your company would look like. All three of these people will tell you “you’re right” or “you’re wrong” based on what’s in their head. Figure out what they’re thinking, why, if you can add more to the big picture, and get more useful data.

You can learn from the wrong people too

It’s worth noting that you can learn A LOT from wrong people. First off, if you tell 5 people what you’re doing and no one gets it – then you’re doing a terrible job explaining it.

On the other hand, you may find out that your go to market is a bit cutting edge and no one intuitively understands it simply because you’re doing something other people haven’t thought of. That’s a valuable learning too.

Vetting the people you trust

What I like to do to understand whether I should listen to someone is to logically deconstruct what they’ve said. Are there gaps? Are they willing to get into the details of what they’re saying to understand if they’re right/wrong? Are they saying things that are simply logically inconsistent?

For example, one “luminary” told us how our company is just way too early for him as an investor. Then he went on to brag about this one investment he made that just signed up their first enterprise deal, for $15k. Ok, so we have way more revenue than this company you’re proud of, and we’re too early? That doesn’t make any sense. Of course, I have a high risk of taking something like this personally and so have to be aware of that in my judgment of him as well.

Bottom line: Make sure people you get advice from aren’t ego driven, have aligned incentives, know stuff you don’t, and that you feel on are the same page as you are.

Ok, my video has stopped encoding which means it’s time for me to get back to work. If you have thoughts on this, please leave them in the comments. I’d love to learn from others in this area as there are clearly no black and white ways to operate, but it’s so very important to have a semblance of a framework for this.

One trick to get to inbox zero: respond to cold emails

In this post, I want to share a secret that perhaps many people who’ve never been in a sales role don’t know.

You know all those emails you get to your work account from people you don’t know? They’re from sales people – usually a Business Development Representative, Account Executive, or whatever. They got your email from some database, or because you listed it on a website 3 years ago and it’s still easily findable from a quick Google search.

They think you want/need their product. And, they’re pretty interested in talking to you about it. In fact, most modern sales organizations have a 10+ touch cadence when reaching out to a prospect. This is a combo of emails, calls, voicemails, and social touches.

So, if you don’t respond to this person’s first email, they’re going to reach out to you another 10 times over the next few weeks.

If you’re like most people, you’ll “ignore” these emails. “Ignore” typically means read the email briefly, try to remember what it was about, remember it relates to a product and person you’ve never heard of, and then delete it. That process takes around 90 seconds. So, for each sales person reaching out to you, you are going to spend 900 seconds fending them off. That’s 15 mins of your life (and probably a whole lot more!)

Aren’t they jerks for emailing me out of the blue?!

If I hadn’t cold emailed a few thousand (or more) people in my life, I’d probably think sales people were jerks – and not worth the time of day. But, they aren’t. For worse, the b2b vendor/customer market is just inefficient, and cold outreach is unfortunately one of the best mechanisms our economy has for matching the right company with the right product.

These people aren’t calling you to be a jerk, and they aren’t calling you to scam you either. 90% of sales people are selling something that is worthwhile (sorry other 10%). It may not be worthwhile to you, but it very well could be (PS they are reaching out to you specifically for a reason, they’ve done SOME level of research, as their time is valuable too).  It’s suboptimal at best to turn these people away without taking 60 seconds to triage their request.

A better solution

Here’s what you should actually do: read the email, think through whether or not this product/service is relevant to your business, and reply to the sales person with the appropriate response. Here are some reply examples:

  • “This is something we’ve been thinking about, I’m free next Wednesday morning, shoot me an invite.”
  • “Let’s jump on the phone for 10 mins so I can understand what your product is a bit more, do you have time now?”
  • “This isn’t relevant for us because {reason}, but could be in 3 months, shoot me a note then.”
  • “This isn’t going to be relevant to me because {reason}, but good luck.”

Congratulations, you just saved yourself the next 10+ follow ups and your inbox is all that much closer to zero messages (not to mention your voicemail, Inmails, Twitter mentions, etc).

A really bad response is: “No thanks.” This piques the good sales person’s interest and they want to find out why, especially if they’ve done some discovery beforehand and think that you are actually a good fit.

Here’s the other reason to respond to the initial email

I find that many people get slightly arrogant when they are being chased. It happens to junior VCs when seasoned entrepreneurs want to get time with them. It happens in the world of dating. And, it definitely happens to people who have vendors chasing them.

Here’s my advice: get over yourself!

If you allow yourself to get arrogant, you’ll miss opportunities. You won’t see the person who’s chasing you who is actually super relevant to what you’re doing, and could add value to your business. You’re going to dismiss them with your chin up, and then lose money by not buying their solution.

How do I know this? Because I see it happen all the time in the world of HR. I see it when I talk to HR folks about what ATS/HRIS/etc they are going with, and I see it when I talk to people about our product who I’ve been chasing for months but by chance meet at a networking event and they say “this is what we’ve been searching for!”

To recap

When you get a cold email, read it, and triage it. Respond to it in the proper manner so you are taken out of the standard outreach cadence and can learn more if appropriate.  Congrats, just just saved 15 mins, and perhaps are going to learn more about a useful product/service.

Some thoughts on valuing SaaS companies

When I worked in venture capital, I was lucky enough to have the opportunity to invest in some really great companies during their early rounds.  Now some of those companies are going public, and I find myself spending some time thinking about when to sell my stock in these companies.

I don’t think anyone has truly figured out the formula to value these companies.  There just aren’t enough examples of SaaS companies that have reached maturity and shown us what they really look like in the long term.  Salesforce still grows at 23% annually and trades at over 100x EBITDA!

Nonetheless, I thought it’d be an honest exercise for me to write some thoughts down and then review them in a few years.

I think that growth should be the number one factor in considering SaaS valuations (when I say valuation, I mean how much is the company worth on a revenue/gross profit/EBITDA/FCF multiple basis).  If a company can grow at 50% for 3 years, it’s topline will be nearly 3.4x higher!  That’s powerful.

If you’re a real SaaS company, this means you have 80+% gross margins and should start seeing nearly 40 cents/dollar of new revenue start to fall down to operating cash flows.  Assuming the company that grows at 50% annually was cash flow breakeven, that means your operating cash flow in three years is more than your current revenues.

No two companies are the same.  The top factors that would effect valuation are how scalable growth is (sales/marketing channels and economics), how long growth can go for (market size, competition), churn (and how it contributes to growth), and margin profile (gross and net), barriers to entry (that will protect current revenues and make sure new competition doesn’t chip into existing growth prospects)…there are some other things pretty important too, like management’s incentive system.

I think what a lot of investors have figured out is that if a company keeps growing, you can pay through the nose (relative to what most companies trade at) and still make a nice IRR.  I agree that growth is the most important aspect of valuation, and that most of the other factors are basically contributors to growth.  Even in these heady times of crazy valuations, I’d say that a lot of the public companies are undervalued!   The other main factor here is the margin profile.  If you can’t ever be profitable, then forget it.  And, in the case SaaS companies, it’s more like you have to be VERY profitable.

I don’t have time to look up various rules on making stock predictions for companies you own.  So, I’ll leave you with this very basic spreadsheet (SaaS valuations thoughts) that should illustrate that growth is key in valuation and how I think various companies should be valued (although I guess the numbers in blue are very much up to interpretation in most companies).  Enjoy.

How to do well at your first industry conference as an entrepreneur

Last week I went to my first conference as an entrepreneur – HRTech, in Las Vegas.  I went in with little understanding of what to expect at a 10,000 person expo full of vendors, customers, investors, and others.  Nor did I really know how to best use my time.

We had a booth in the “startup pavillon” which was regrettably on the outskirts of the conference, but had decent traffic since it was close to the bathroom.  It was only large enough for 1-2 people to stand at, but was cheap :).

Here are a few of the things I learned for people who will one day attend their first conference as an entrepreneur/salesperson.

1) Make notes on cards, you aren’t going to remember.

When you talk to someone, especially a potential customer, you’re thinking “there’s no way I’ll ever forget this conversation!”  Luckily I still wrote down notes on ever single business card I got, and sent myself a quick email for those contacts I couldn’t get business cards from.  You will NOT remember 80% of conversations after you recover from your red eye back home.  This makes for most customized email follow ups post conference.

2) Get sleep before/during/after.

Lack of sleep and cognitive functioning are highly related, same with energy levels.  Why would someone trust/remeber you if you can’t articulate what you’re selling?  Don’t think going out until 2 am is a good idea just because it’s Vegas.  Get some rest and make the most of your time, as well as the money you spent getting there.

3) Do pushups/burpees/situps/squats (in your hotel room).

The endorphins released during exercise will make you feel happier during the conference which makes you a better sales person.  They’ll also increase your cognitive functioning.  See #2 above.

4) No one will visit your booth.

Unfortunately, the only people who want to come to your booth are the intellectually curious (and generally not relevant), or people trying to sell you.  That means you have to be aggressive in getting people to your booth.  The following tips help you do that.

5) Smile, hold something social proofy, and don’t be desperate.

If you smile and say “hi” some people will smile back, or at least nod.  If you hold something like a cup of coffee or a nice shiny pen, this communicates you’re legit in some small way.  And, if you can control your voice to sound full of confidence (which you will be anyways because you’re crushing demos left and right), they may even turn and look at you.

5A) Wear casual clothing.

Don’t feel like you need to rock a suit or a blazer simply because it’s a professional conference.  It’s preferred to wear something more casual to make yourself approachable.  Trust me, I A/B tested it.

6) Ask qualifying questions.

Just like in sales, you don’t want to spend lots of time with people who aren’t relevant to your goals.  Ask something like “Are you in employee benefits?”  If no, then “have a great conference” and you both feel good.  If yes, then “Great, I’d love to show you my product.”  It’d be weird if they just walked away after agreeing it’s relevant, right?

7) Discover.

You wouldn’t have the same conversation with a prospect vs a competitor vs a collaborator vs an investor right?  Ask them what their role is.  Try to figure out if you can use jargon, or if you’ll have to explain the various pieces of your product in more simple terms.  Craft your conversation accordingly.

8) Get sick swag.

Get something cool.  We almost bought pens, thank god my co-founder thought of these credit card sized bottle openers instead.  Much less likely to be thrown away.

9) Stay cheap.

This is especially true for startups.  Have your friends take you to free parties.  Make sure the cabs don’t charge extra for using credit cards (they charge $3 extra in Vegas, what’s up with that???).  Stay off the strip in a reasonable hotel…you’re just sleeping there.

10) Enjoy yourself.

There is a lot to feel overwhelmed by.  But, make sure to take time out to enjoy the experience of your first conference.  Make new friends.  See cool technology.  And have a beer.

The Admissions’ Mistake

The first class I had freshman year at NYU was 8 AM on the 4th floor of Bobst Library, right on the south side of Washington Square Park.  I remember it was a strangely cold, overcast September day.

I was incredibly nervous, and really unsure what to expect.  This was especially true considering the class was called “Writing the essay” and I wasn’t a very strong english student in high school.  As it turns out, I did ok in the class.  But, what really stood out to me was the advice my professor gave on that first morning.

She was 4-5 years out of Harvard.  And, she said that on her first day of college, the Dean had said “there will be a point during your first year here that you feel like you’re an idiot, everyone around you is so much smarter, and that YOU WERE THE ADMISSIONS’ MISTAKE!  Fear not, as this is definitely not the case.  Everyone feels like this at some point, and you’re going to be just fine.”  By the way, I am totally paraphrasing what I think was said, as I was hearing this second hand.

It’s going to happen to you.  When you’re a freshman, or start grad school, or are at your first job, or start a company, or (presumably) start a family…you’ll always have a point where you think you’re in over your head – you’re the admissions’ mistake!  But, you’re not.  You’re just having a bad afternoon, or week, or month.  And you’ll recover, look back, and say “wow, I was actually not half bad.”

I’m posting this because it’s been a pretty powerful lesson for me to keep in mind, especially when the going gets tough.  What made it powerful for me was that this was said to kids at HARVARD!  Everyone at the #1 school in the world was feeling insecure and stupid.  Imagine that??  If it was happening to them, then this is clearly an illogical feeling and I don’t have to pay it much mind :).  I hope you’ll interpret this with the same lesson.

Don’t be nice to startups

These days, chances are you or someone you know is starting a company. And, whether you’re hacking on a side project, scheming with a friend, or actually working full time, the number one thing founders are after is feedback (after venture capital dollars, revenue, a CTO… you get the idea).

With that in mind, I wanted to give some advice to friends of founders, early customers, and anyone else who’s giving feedback to startups.

Simply put: don’t be nice when they ask what you think of their product.

It’s human nature to want to support your friend, or another professional who’s put time and effort into a company. This usually results in sugar coating your feedback. Don’t.

Don’t think “oh, well they’re putting their heart and soul into this thing, so I want to support them.” If you tell a company their product is “pretty good,” “interesting,” “innovative” or sugarcoat it in any way, you are doing them a disservice.

If you think “well, I don’t want to be a jerk, and I know starting a company is really hard,” then don’t be a jerk – just be honest. Startup founders are rejected on an hourly basis most days, your additional rejection bounces off the armor just like all the rest. But, a truly honest answer to any product is hard to come by and very very useful because it is so rare.

So, the next time you’re doing a survey for your pre-product friend, tell her what you really think of her idea and vision. When it comes to feedback, the only wrong answer is the inauthentic/unthoughtful one. It’s a founder’s job to parse all the info that comes in and you’re just one input – so don’t worry about being ‘wrong.’ This same advice goes for early customers, users, etc.

Mid-post disclaimer: my favorite character/investor on Shark Tank is Mr. Wonderful. My favorite judge on American Idol was Simon Cowell (not that I’d ever watch that trash). They may be a bit tough, but at least you know where they stand (and you can calibrate how you interpret their feedback as you know they are a bit tough). In light of this, maybe not everyone wants this sort of brutal, Bridgewateresque feedback.

But you don’t have to be brutal, just be honest. Maybe once in a while that means being brutal, and so be brutal. And maybe sometimes it means swiping your credit card, or using the service, then do that too ☺. And, if it’s something in between, do some soul searching to try and figure out why you are on the fence.

Ask yourself, ‘what would make me stop what I’m doing and use this right now?’ Be a method actor for a moment, breathe deeply, and articulate what you’d need to be a user/customer. Don’t list random features you can think of that might be useful in some future scenario. Think RIGHT NOW what do YOU NEED in order to USE/PAY FOR THE PRODUCT. That will be the nicest thing you could possible do for a startup.

PS please feel free to reference this article when giving me harsh (but honest) feedback.