155 Kudos


MVP: The Features Are Silent

Designing products is an extremely difficult process, filled with diversions and pitfalls that you almost never can anticipate.  As of late, there has been tremendous focus on the notion of the “minimally viable product” – the simplest essence of your vision which fundamentally solves a specific type of customer’s needs.  I’m a big proponent of the concept of the MVP, though more often than not, the theory outperforms the practice.

Most often, when thinking in terms of our MVP, we think in terms of the features we plan to offer.  We first develop an unsorted list of ideas that we thing would be “killer” and through a variety of steps and tumbles whittle this list down to something more manageable, more approachable.  But maybe that’s completely the wrong way to handle things.  Maybe that just leads us to a set of features, tightly coupled together but not necessarily of value on their own.  If you take a survey of the MVPs you’ve seen, how true does that ring for you?

So what’s a product if not a compilation of the features.  Isn’t that the secret to the 2+2=awesome formula?  From my experience, a product is comprised of a number of “other” features, very distant from just the software that powers them.  Here’s a few of those:

  • Acute understanding of the customer and their current problems
  • Acute understanding of the means through which a customer derives value and earns a return
  • Outstanding user experience that minimizes the friction in a process – that’s not necessarily fewer steps, just less confusing ones
  • Excellent copy that speaks the language of the customer
  • Well-thought out and tested onboarding experience that drives customer success

Now I know we’re all building those concepts into our MVP, right?  Hell, I wish I could say we’ve done that, but I’d would totally be making it up.  The challenge is that our urges to get something out there, to satisfy that most anxious of first customers, often can lead us to take shortcuts.  There’s nothing wrong with shortcuts, so long as they’re recognized as business debt that has to eventually be paid in full.

So what’s a bootstrapped startup to do?  Do you really have to wait for all of these things to be in place?  Of course not!  You’re a hunter, you use what you have at your disposal.  It’s completely within your reach to spend some time on ALL of these items without making the deep dive into the abyss.  If these bits aren’t there, it’s hard to learn what’s not working – must be present to be measured, regardless of your measurement technique.

The sign of a true craftsmen is that you can never see the seams in their work.  You should expect nothing less of your MVP.


30 Kudos


Avoid the Failure to Launch

Often times, we’re challenged that we’re not building something “great enough” for the world – squandering our natural abilities for a fast dollar.  Ilya Lichtenstein recently made the case:

In technology, long term thinking is impossible, because everything changes so fast, and the pace of change is quickening. The rules are changing too fast. Nobody knows when a sudden shift in technology will open up new markets and business models.

All we can do as entrepreneurs is take it step by step, and adapt quickly when we sense the market shifting.

“The value of short term thinking”, Iilya Lichtenstein

As someone who’s started many things and even launched a few of them, it pains me that anyone would diminish just how much time, energy, sweat and tears it takes to put anything out at all.  There’s nothing simple about it.  In fact, and this is common wisdom in startup circles, you should carry some shame for your first version.  Some would tell you if it’s not a piece of shit, you’re waiting too long.

I’m not in the camp that you should put just about anything out – but I am ever a champion to make sure you get something out there.

For most entrepreneurs, optimizations and the pursuit of perfection are convenient excuses not to launch.

I’ve done this so many times, I can’t even justify telling anyone else not to do it – but I will.  It takes desperation (the kind that comes from writing your last check) or a swift kick in the ass from someone who’s tired of hearing how good your shit will be — maybe it’s both.  Dig down deep and do what’s expedient – you have to earn the next swing at the bat.

There’s no guarantee you’ll get another at bat so you really have no reason to not get out there.  There’s no way to know what tomorrow will hold, who might swerve into your lane, or who might decide your cheese looks extra tasty.  All you can do is launch – the best enough thing, as fast as possible.  Trust me, you’ll feel so much better and it all will start over again.


21 Kudos


Stretch Your Legs, Meet The World

One of the things that first drew me to Lean Startup thinking was the focus on breaking the habit of locking yourself in a room and coding till your eyes are burning.  The whole notion of “getting out of the building” really has tremendous value.

Earlier today, I was preparing some comments for someone who posed the question: “What have you learned about managing a technological business that you would pass on to the next generation?” My response was simple:

While technology powers more and more of our businesses these days, it’s also a convenient crutch that we can often hide behind in the place of understanding.

Technology is almost always just a small part of the process of building a business.  Perhaps more important than anything is learning how to build and foster productive relationships with people: your co-workers, your customers, and your evangelists (both at work and at home).

I just recently returned from a week away.  In many ways, this is a grueling thing to work through considering our daily commitments, the work that needs to be done with my co-workers, and the deluge of tasks that come up minute by minute in a startup.

On the other hand, I walked away with a lot of really amazing new things from simply going outside:

  • Reconnected with some folks I hadn’t seen in a while
  • Got a few leads on great potential hires
  • Introduced dozens of new people to our platform
  • Dispensed some hopefully useful advice to up and coming founders
  • Learned in person about the challenges our customers are facing in their daily operations

If you can get just a small amount of that done, it’s likely time well spent.  If you can get more, then all the better.

Having the audacity to speak out loud is easy for most of us founders. Stomaching the courage to take direct fire is the challenge for us all.


36 Kudos


For Startups, Honest is the New Smart

When I first started blogging in 2003, the most compelling thing about the entire medium was that it was honest – no bullshit.  There was just a smaller community back then and a lot of the folks knew each other.  That was when I had the chance to first meet and befriend Dave McClure.  I remember first sitting down with a group for Dim Sum at Canton Seafood after a Blogger Con at CNET’s offices.

I remember this today as I was reading a great post from Dave that reminded me of something happening beneath all the bullshit.

I felt lucky I didn’t get fired during my time there, and as I left I felt relief that no one had figured out I was kind of a lame duck who didn’t know where I was going – Dave McClure

Dave’s doing his thing, telling it like it is.  The truth is we’re all filled with uncertainty and doubt at almost every step we take.  There’s hundreds of questions and every choice is agonizing.  I think Dave has developed such a diverse following because 1) he knows his shit 2) he doesn’t bullshit.  We all love hearing the truth, so long as it’s not about ourselves.

The very old saying, “The truth will set you free” is now an axiom of startup life.  Everything from Lean Startup to Startup Post Mortems espouse the value of the truth in the things we do — or at least more truth than we’re traditionally used to.  It’s hard to believe that we’re not more honest all the time, but considering that most of us have to make fairy tales from nightmares, it doesn’t surprise me in the least.  The great lie of entrepreneurship is you tend to hide from the truth until it’s not scary.

So with this new form of honesty comes a new form of intelligence.  It’s opinionated, yet informed.  It’s making us ask new, more interesting questions.  It’s challenging us to build better businesses and to maximize our efforts.  It’s making us tell the truth, when lies use to suffice.



14 Kudos


Ignore This Post: Thoughts on Giving Advice

I’ve been helping, or attempting to help, other entrepreneurs for more time than I can remember.  For the most part, it’s a rewarding experience and I hope has proven to be useful for most of the folks I’ve had a chance to meet.  That said, advice from a third party is never going to be as useful as the critical analysis you can do on your own.I’

Recently, I came across a post from Dalton Caldwell that really put a finger on this:

Beware of black-and-white thinkers. Beware of people that present very simple narratives as the explanation of incredibly complex events. Don’t take anything you read too literally. Be comfortable with the fact that much of what you feel will be squishy and complicated. Realize that everyone feels this way, it’s just that some work harder than others to cover it up. – Dalton Caldwell

As I’ve noted in previous posts, there’s no map that can magically guide you where you want to go.  There’s also no mystical fairy pointing you in the right direction.  All advice is made up of the sum of experiences (fears, anxieties, successes) your advisor has had as well as the lessons learned in the process.

I plan on expanding on this in the future, however, here’s the quick summary of my model for startup advice.

Step 1. Understand as you understand

I like to have a startup tell me what they do in their own words.  I will try and interrupt as often as possible during this explanation to take themout of the pitch and get them to talk on their feet.

Step 2. Re-state their idea

It’s most useful to make sure that we are on the same page.  Re-stating their concepts helps make sure that we are on the same page and quickly sorts out any misunderstandings I might have.  It also lets them know whatever bias I might have in my thinking.

Step 3. Brainstorm!

I love to find out what problem they are most worried about and try to brainstorm as many different solutions to the problem as possible.  Most of this advice will have been covered by the smart, dedicated entrepreneur.  If anything new is raised, it’s worth drilling down a bit more.  Sometimes it’s something simple and was missed since they’re neck deep trying to move forward.  Sometimes, though, it’s based on some experience I may have previously have so I try and unload whatever insights or anecdotes I have.

Step 4: Throw down the Gauntlet

As a point of order, I will almost always throw down a challenge for any entrepreneur I meet.  If we’re in agreement on something, then I’ll set a challenging but not impossible goal for our next meeting.  If we’re in disagreement, which is where I actually prefer we be, it’s a challenge to their convictions.  When that happens, as I’ve experienced many times on my own, it forces everyone to go back and think about why they believe something and to seek out the proof that it’s either right or wrong.


So while I agree with Dalton that black and white advice requires caution and consideration, I tend to prefer the negatives – they force me to learn.



15 Kudos


A Day In The Life

There’s been an interesting series of posts lately that provide a glimpse into the daily routines of every day folks.  Most recently, I came across  “A Day in the Life of a CEO” by Ryan Carson, and entrepreneur I both respect and admire.

I think these small windows help people who might glamorize any particular lifestyle get a reality check.  They also serve to highlight just how dysfunctional we can all be :)

So here’s my typical day (Monday – Friday)

Wake up, check for fires, then immediately go for my 2-3 mile run and workout

Coffee for me and the wife (she won’t drink it for another couple hours)

5:45am – 7:30am
Review code commits, review closed tickets from Asana, check in with remote teams

7:30am – 7:45am
Shower and get ready to head out

7:45am – 8:30am
Reading and usually some writing (like this!) – I highly recommend ByWord.

8:30am – 8:45am
Walk to the office (~1m)

8:45am – 9:30am
Reading various news from Techcrunch, Techmeme, DailyJS, Hacker News

9:30am – 10:00am
Morning Standup with SF Team

10:00am – 12:30pm
Product planning, preparing tasks for team

12:30pm – 12:45pm
Lunch at my desk, light reading

12:45pm – 4:00pm
Switching gears between customer support, account management, product development and design

4:00pm – 4:15pm
Coffee Break

4:15pm – 6:00pm
More of the same

6:00pm – 8:00pm
Networking events – I try and do one or two of these a week to meet new folks and potentially recruit

8:00pm – 10:00pm
Decompress in front of the TV with laptop on the lap

10:00pm – 11:00pm
Collect notes for Evening Standup – we have 6 team members in India/Ukraine/Macedonia/Turkey

11:00pm – 12:00am
Evening Standup

12:00am – 12:45am
Pass out or catch up on some news

This is a pretty hectic pace and definitely one of the biggest challenges that comes from having both local and remote teams.  It does force a certain amount of discipline, which is good overall.

On Health

I’ve started running only this year.  I’m motivated to get down to a 21 minute 5K so that keeps me going.  I prefer running early in the morning before there’s any traffic to be seen.  I track my running with RunKeeper.

Walking is another important part of my day and I try and walk at least 2 miles a day.  I track all my non-workout activity with the Nike+ Fuel Band.

On Sleep

I’ve never been one to sleep much.  I can be fairly functional with 4 hours, but prefer 5-6.  If I sleep 7-8 hours, I will basically be tired most of the day – it completely throws off my rhythm.  I don’t need an alarm in general, but I set one anyway and usually will shut it off before it rings.

I do enjoy what I do so most of my day is enjoyable, interspersed with intense moments of anxiety, of course.

On Weekends

I’m much more likely to take time off on the  weekend now – the pace is too hectic otherwise.  As I’ve said before, though, there’s not much choice most of the time.  I’ll usually take Saturday off and into Sunday morning but will be back to work on Sunday.

If my wife is doing her own thing, then I’ll usually fill that time with a movie or work.



49 Kudos


Founders Never Sleep

TL;DR As a founder, your natural inclination is to be singularly focused on your startup.  While this is great for as long as possible, balancing your life can help you achieve even greater success.

Back in the Day

I’ve fortunate enough to have taken a short vacation this week with my wife and family. For a long time, vacation was a completely foreign concept to me. When you’re driven to succeed and haunted by the specter of time, it feels impossible to let go.

When I first started out as an entrepreneur, I had no idea what I was doing (I’d argue that may not be that different today). We rented our first office on 14th Street and used up almost all of the money we had on our deposit and first month’s rent. It was awesome.

Those times were really something. Eventually we did run out of money and we all lived in the office – switching between a variety of stations, be it the mini conference room, the back corner, and often right there in our chairs. It was sheer stubbornness that me pt us there – we wanted to do it on our own.

It took me 4 years of sleeping in corners and showering at the gym before I actually got an apartment again – it’s hard getting a lease when you have no steady income (different post). I didn’t quite know what to do with myself once I had an apartment – sometimes I would just work too late and revert to my old habit.

Focus Your Efforts

The problem back then was I was running two businesses. During the day, I would consult for a variety of companies in order to fund my own ideas and team. After my 10 hours with a client, I would shuttle back to my hard-working team and we would toil away through the night.

This, in my opinion, is a bad habit to form.

You see, startups are like fire. They need oxygen to fuel them. You can’t build a roaring fire by blowing a little air over it once a day. You can’t succeed when every day you return to find someone’s stomped out your camp while you were sleeping.

The fear of falling behind, of missing out is so tremendous. You sleep with one eye open all the time. No matter what else you are doing, you will find it harder and harder to turn the other part off – until you stop caring about either one.

Letting Go Is Hard

Fast forward to today. I’ve succeeded in getting to where I only run one business (well, close enough). I’ve again got a great team and we are working to succeed. But the beast is still there.

My vacation has been wonderful. Much to the dismay of my wife, though, it was probably more like a conference or business trip. Every day was bookended with team chats, fires to put out, and thoughts that needed communicating.

My startup is my child. That might sound ridiculous from the outside, but it is true. As any parent can attest, you never drop your little one off without worrying about how it’s doing. You learn over time that you don’t have to be manic all the time and your check-ins grow ever more intermittent – but you never stop.

Some day it will grow to the age when it can fend for itself. Until then, I’m still the reluctant dad unwilling to let go of the handlebars.

Looking Forward

My advice for anyone reading this is to try and get as singularly focused as quickly as possible so you can learn and react better than anyone else.  Learning early on how to leverage all of your assets (expertise, network, team) will help you stay ahead of the work curve.  Eventually, you’ll want to stay just as focused but evolve from the always-on model to the most-productive model which will free you to grow in new ways on all fronts.


5 Kudos


Failing for Fun and Profit

As a startup entreprenur who’s experience far more failure than success, this quote really rings true with me:

“And the fact is, one way or another, all ships take on water … and one way or another, practically all startups internally are disasters. And they just hide this from the outside world. — Janice Fraser

From the outside, you’ll always get the highlight reel from other entrepreneurs you chat with.  There will be a wide range of things which seem successful.  It’s only when you really get to know another founder that you can start to speak the honest truth with each other and lament all the things that are going wrong.  But even there, in the closest of friends, there’s always some posturing – what’s an entrepreneur to do ;)

Which leads me to the matter of failure as a tool for your own enterprise.  I’ll split that into a couple of simple buckets:

  • Failing for Fun
  • Failing for Profit

Failing for Fun is the process of doing something just for the hell of it.  There’s a curiosity that you want to explore, an itch you must scratch.  We purse these things all the time.  Their the stupid things like making something pixel perfect when what you have will do.  They’re experiments you do to test the edge cases, even though no one’s really asking about an edge case.

In short, there’s nothing wrong with Failing for Fun.  It’s the sort of energy you spend when you don’t learn anything, and that’s OK!

Failing for Profit, however, is a completely different beast.  It’s a process, it’s methodical and most importantly it’s a tool that moves you somewhere as opposed to anywhere.  In today’s Lean Startup world with a broad toolkit available to help us learn more and more by mesuring as often as possible, we have fewer and fewer reasons not to fail for profit.

Failing for Profit should always involve learning something new about your business, your customers, or yourself.  Ideally, you power through as much of this as possible.  It’s not the sort of thing that just happens, it takes planning and energy. It takes a great deal of honesty – something most of us don’t have the courage to face.

Time’s awasting, go fail yourself.


8 Kudos


The Enthusiasm Gap

Entrepreneurship is a ever-lasting sales pitch.  From the time to start until the day you call it quits, you’ll find yourself trying to coax someone down some path.  For most, it’s one of the most enjoyable parts of the journey, for others it’s the most frightening.

There are many kinds of “sales” made once you get going.  Here’s just a bunch of the ones I’ve personally experienced:

  • Pitching anyone who might be able to validate my idea
  • Pitching my spouse for the green light to pursue my vision
  • Pitching my co-founder to continue and/or change directions
  • Pitching investors to invest in the future we see
  • Pitching contractors and employees we are the future they should build

Oh, and at some point in time, you eventually have to:

  • Pitch new customers to convince them that their problems dissolve base on your solution
  • Pitch your customers that the next shiny object is just shiny
  • Pitch partners that you will make their business better

So yeah, there’s a lot of pitching.  But there’s a secret.

Most of us aren’t salespeople at all.  We’d do horrible if put out in the world and told that our survival depended on how well we could sell product x to customer y.

The secret is that we’re all passionate evangelists.  We don’t sell our startups nearly as much as we believe, often to our own detriment, so blindly in what we’re doing that we can’t exude enthusiasm for it.  It’s infectious and most people can’t resist that charm.

The real challenge, then, is not learning how to sell better (we can all benefit from that).  No, the real challenge is to make sure there are no gaps in our enthusiasm.

The last thing you want in your startup is to be chasing the shadow of the dream you once had.