Brad Feld

Category: Entrepreneurship

Fail Harder

Jun 10, 2008

A reader (thanks Austin) sent me two great failure links today.  The first is from BoingBoing and is titled J.K. Rowling on the power of failureIt’s an excellent short segment from her excellent Harvard Commencement Address titled The Fringe Benefits of Failure, and the Importance of Imagination.

The next is a sign made entirely out of push pins that says "Fail Harder".

I spent the afternoon at TechStars meeting with five of the ten teams.  They are all dynamite, although some of them will fail at their current incarnation.  Just remember – fail hard, fast, and then get up and try again. 


If you are an entrepreneur, I expect you’ve shouted this (or at least thought it ) sometime during your time on this planet.  My partner, and ex-lawyer, Jason Mendelson has a fantastic rant up titled Why Start-up Lawyers Frustrate MeHe provides a detailed look on his two gripes: pricing and execution.

While "some of my best friends are lawyers", I couldn’t agree more with Jason’s post.  I’m looking forward to Jason’s equivalent of "fucking accountants" post which is hopefully coming soon.


Yes – I’m back from vacation.  But you probably figured that out already.  The next six weeks are pretty intense ones for me in my annual rhythm of things – I love the time period of memorial day weekend through July 4th.

A few weeks ago I was interviewed by Reena Jadhav on Vator.tv on how to get funding.

Other than my excessive hand gestures, it’s a good look inside my brain about how I think early stage entrepreneurs should think about funding, especially first time entrepreneurs.


Great, inspiring video on failure.

(thanks Scott).


I just finished reading Bounce!: Failure, Resiliency, and Confidence to Achieve Your Next Great Success by Barry Moltz.  I think Barry was originally introduced to me by Matt McCall, one of my co-investors in FeedBurner and a Chicagoan like Barry.

There are very few good business books about failure.  Most of the ones I’ve encountered in the past use failure as an early part of the "rags to riches" process of the classic Horatio Alger parable.  Dull.

Barry takes a different approach – he uses failure as a theme throughout the book and describes it as an integral part of a long term business experience.  Just like the cliche "you haven’t really been in business until you’ve been sued", I think the cliche "you haven’t really become an entrepreneur until you’ve failed at least one" applies.  Barry does a good job of weaving a variety of individual stories (including his) around his philosophy and theorizing.

Like most business books, it is about 50% too long.  Long ago I concluded that "editors" believe the hardcover business book needs to be around 200 pages.  As a reader, I think there should be a 100 page limit – that would force the writer (and editor) to get to the point and be less redundant.  While this doesn’t detract from the book too much, there are a few sections that are skimmers.

If you are an entrepreneur – especially one early in your career – this is a very worthwhile book to read. 

On the failure theme, Andrew Hyde has a post up titled Startups Fail that includes news about a handful of recent Boulder failures: Nau, Organica and Falling Fruit.  Andrew reminds us that failure is an integral part of entrepreneurship.


I was in a meeting with one of our new portfolio companies today.  In response to a non-obvious question, the CEO said "I don’t know is the answer to your question."  I fell in love with this CEO all over again and was reminded of Josh Kopelman’s magnificent post in March titled I Don’t Know …

Another great line from the meeting was "The only useful things to come out of marketing budgets in early stage companies are stickers and t-shirts."  That was – of course – from me.


Rejection isn’t failure.  I’ve been back from vacation for five days (including the weekend) and I’ve send out around 100 50 (if felt like 100, but I went back and counted and it was slightly more than 50) rejection emails to deals that came into my inbox while I was on vacation.  It’s part of my job – and I try to always at least give a little context as to why something isn’t interesting to me.  But 50 in five days (really 10 days including the vacation) starts to be a little discouraging. 

I remembered a great email from a close friend recently in response to one of my previous posts on rejecting plans.  My friend is a writer and has completed several as yet unpublished books.  Following is her riff on rejection.

"Your post made me smile a little because it could so easily have been a post by a literary agent. One big parallel is that literary agents are inundated with people wanting their services (probably a lot more than you are – believe it or not!). A good agent, and there are a lot of them, receive an average of 1,000 unsolicited query letters a month. Surely, some get much more. These queries are equivalent to the pitches or emails you get. Like you, agents often won’t take on more than 6-8 new clients a year – if that. So, there are a lot of people (like me!) 🙂 who receive a lot of rejections. It doesn’t necessarily mean the product is "bad", but as you say… if it doesn’t fit with the agent is working on, interested in, thinks the industry/market can carry at this particular time, it’s a "ding" a.k.a. "rejection." I’ve received hundreds of rejections that are postcards or sometimes, literally, a thin two inch strip of paper that has clearly been copied until it’s almost unreadable saying something like: "Thank you for your submission. Due to the number of submissions, we cannot reply specifically to everyone, but your writing is not right for us. The publishing industry is a very subjective one, and you should not take this to mean that it might not be right for someone else. Best of luck." -"blah blah agent name here" Sometimes, not too infrequently, if an agent allows electronic submissions, their website indicates: "we’ll only reply if we’re interested." That always seemed a little rude to me, that they couldn’t even find the time to send a form email. But, it is what it is… sometimes you’ve just gotta let these things go.

You’ve known me through this entire writing/publishing quest/process, and I have grown through it. After years and years of these rejections and hearing agents say that "it’s not personal," I actually "get" it. (This only happened a couple of years ago.) It really isn’t personal. Just as I am looking for an agent and publisher, these folks are truly looking, searching, and hoping for the next successful writer. They *want* to find something they love. They *want* to make that call to tell a writer that they’ve sold their book at auction… Unless I am incorrect, you are looking for "the next big thing" within your world, too. Something that will be successful for everyone, on many levels.

I know you asked "entrepreneurs" how they’ve felt, being passed on, I thought I’d chime in anyway, since I am quite familiar with this type of rejection, I believe. I think the perception varies depending on where the person is in life. Are they confident? Do they understand that it is, in fact, NOT personal? It took me years and years and years to understand that it’s not personal. 🙂 I tried to understand before, but didn’t. I’d cry sometimes, for sure, and feel sad and gloomy under the sheer weight of these rejections. Then, I started not allowing the "weight" of these rejections to be so big. Remember that I am still unagented and unpublished and still trying to get successfully over those hurdles. But, my reaction to these rejections now is "oh well. I’ll just keep going."

I have also learned to listen when I get feedback…or when someone likes my writing, but doesn’t think they can sell a particular book….they are telling me something. Sometimes I get explicit invitations to "please send us a query of anything else you write" and sometimes it is more subtle, but I am reminded that there are things for me to learn from these "rejections." I’m sure the same is true – sometimes at least – from people you decide not to go with.

Maybe you like the people, think they’re great, but if they had a different idea, you’d love to work with them. There are always possibilities to create something new."


As I sit here in the San Francisco International Airport (they announce that so proudly over the PA when they tell me that the thread condition is orange every few minutes) I’ve been pondering the unexpected Frontier Airlines bankruptcy.  My Frontier flight is now an hour late so I’ve had plenty of time to surf the web and try to figure out how / why this happened so suddenly.  I’m also almost brain dead from my 10 day trip so it’s hard to actually do anything productive at this point.

I’ve determined that the bankruptcy filing is simultaneously a smart survival move for Frontier and an example of the classic "unintended consequences" (which my dad also taught me result from "complicated mistakes.")  This one is a doozy.  I have no idea what the actual facts are, but the WSJ asserts that the Chapter 11 filing by Frontier was in response to their credit card processor (First Data) increasing they amount and length of time of their holdbacks for credit card receipts.

Let me get this straight. I’m a customer.  I charge a Frontier ticket on my credit card.  First Data processes it but now holds the money until they decide to release it to Frontier.  As a result, First Data effectively controls Frontier’s cash flow (since almost all customer purchases are made on credit cards.)  All right, I got it.

In one of the articles I read, it was stated that First Data increased the holdback percentage from 45% to 100% and the time duration until "the flight was taken."  That strikes me as completely unreasonable on First Data’s part – they now control the float from the moment of purchase until the moment of flight completion confirmation (which I expect is a non-trival reporting process for Frontier.)

Frontier’s response – "Dear First Data: Bullshit.  We are filing for Chapter 11 and invalidate your ability to change the holdback terms.  See you in bankruptcy court."

All the chatter I heard today while waiting for my plane was whether Frontier would be going out of business and whether our plane would arrive.  The fact that is was an hour late didn’t help.  Nor did the fact that the electronic scoreboard announcing the flight time was not working and the gate agent wrote all the info on a piece of paper taped to the wall.  Everyone at Frontier is keeping their chins up and saying "no problem – this is just a technicality."

Hopefully I’ll get home today.  As one of my twitter friends told me – "at least I’m not on American Airlines."


From Adam Smith at Square 1 Bank on how NOT to pitch your company to a VC.

The full segment is below.

There is a philosophy that "all you need to do is get tons of underpants traffic and good things will happen.  When that works, it’s a beautiful thing.  The key word – of course – is "when."  Phase 2 is a dangerous place.