Dharmesh Shah


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How The Business of Software Conference Changed My Life

By Dharmesh Shah on October 14, 2013

tl;dr:  If you work in the business of software the one must-attend event is the Business of Software (Boston, Oct 28th  –  30th 2013)

Note from Dharmesh:  This is a guest post from Patrick Foley.  I normally don't post articles that promote an event — but Business of Software is not a normal event.  It's the ONLY conference that I've spoken at 5 years in a row (an am speaking again this year).  It's the only conference for which I stay at a hotel in Boston (5 miles from where I live) just so I can hang out with the people attending the conference as much as possible.  It's that good. You should attend.  (Note: I am not affiliated with the organizers, my selfish reason for convincing you to go is so I can meet more awesome people).business of software

ABSTRACT: If you’re not satisfied with some aspect of your career, go to a great conference like Business of Software. The best conferences can dramatically alter your perspective and ultimately change you.

Four years ago, I attended my first Business of Software conference. Back then, I was a technical evangelist for Microsoft, and since my customers were other software companies, I thought I knew all I needed to know about this “business of software.”

Obviously, I was wrong. For three days I listened to amazing speakers like Jason Cohen (founder, WPEngine) explain how the different personal goals of founders have an enormous impact on their business actions – meaning you should pay more attention to advice from founders with similar personal goals. I was inspired to hear Peldi Guillizoni (founder, Balsamiq) explain how he built his business – and how his journey actually started while working for a big company (hey, just like me!). I was shocked to hear Joel Spolsky’s very intimate description of how funding really works. I learned measurement concepts from Dharmesh Shah (founder, HubSpot) that I didn’t even know were knowable. I was genuinely moved by the stories from these founders and all the other brilliant speakers. And that was just the first year for me (more great speaker videos from 2010, 2011 and 2012).

At a great conference, the attendees are as important as the speakers. Many of the people I’ve met at Business of Software have become my friends and advisors. One became my cofounder in my first effort at a building a software company (a story for another day). There’s a bond that develops among Business of Software attendees that’s hard to describe. Part of it is that the speakers are highly engaged attendees themselves – something you don’t see often – this is their community, their tribe, and the speakers clearly look forward to being a part of the event from both sides of the stage.

There was something about attending that conference in person that shook me to my core and sparked a passion for learning how software companies really work and what makes them successful (spoiler alert: it’s freaking hard). Yes, I already worked for one, but Microsoft is HUGE – I was a deckhand on a battleship. Although I was working with other software companies, I was ultimately selling to them … you don’t learn how things really work in that situation. I even had a podcast that allowed me to speak with some brilliant founders … but it took being in a room with all these people at once to change me. BoS changed me. (I wrote about that special year and even have a manic podcast episode describing it.)

Great conferences like Business of Software aren’t cheap, but they’re a great investment. Microsoft paid my way to a couple of conferences a year – that’s a HUGE perk of working for an established company! If you work for a company that has multiple layers of management, then they probably have a conference budget already. Use it! I attended Business of Software on Microsoft’s dime in 2010 and 2011. Last year, I took vacation time and paid my own way, because I was preparing to leave my job.

This year took me in another direction. When it became clear that my product company wasn’t going to work, it was still time to leave Microsoft, so I reluctantly returned to consulting. I was a consultant for 14 years before joining Microsoft, and I’m pretty good at it – but I still felt defeated. Sometimes you just gotta lick your wounds, recover, and figure out a new path. I figured I’d build up my financial resources for a few years as a consultant and then try again to build a software company.

But then a crazy thing happened … a few weeks ago, a couple of friends that I met at Business of Software contacted me about a job. They have a small, very successful software company, and they think I could help with their next stage of growth. WOW! I didn’t see that coming. I’ll have my hands in all parts of the business, improving anything I can and learning everything I can. It’s not a startup (they’ve already found product/market fit), but it’s actually a better fit for me at this point in my life, because it provides greater financial stability, and it will allow me to experience how a successful company operates. A while back, I asked Jason Cohen for life/career advice, and this was exactly the sort of situation he said I should be looking for. It’s PERFECT.

I’m sure you can guess the call-to-action of this post by now … sign up for Business of Software and GO. It just might change your life. The best work I did for Microsoft stemmed from Business of Software. Then it inspired me to leave Microsoft and pursue work that I like even better. And now my dream job FOUND ME because I went to Business of Software.

My new company and I haven’t actually finalized my role or my start date yet … we’re going to formalize things in 2 weeks at Business of Software … I hope to see you there! It’s going to sell out, so you need to jump online and order your ticket now. My understanding is that it’s going to be several hundred dollars more expensive next week (if you can get in at all). If you’re on the fence about going, feel free to contact me (pf@patrickfoley.com) to talk about it.

Topics: guest Event
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2 Mental Exercises For Battling "It Won't Work" Syndrome

By Dharmesh Shah on September 20, 2013

Every company has ideas that come up (sometimes frequently).  And, based on the stage of the startup and the degree to which the idea is unconventional, there are always good, rational reasons why the given idea can't possibly work.  There are also bad, irrational reasons too.  The problem is, it's hard to tell the difference.bad idea

Here are some of common reasons why something won't work:

1) We've debated this several times before and have decided it wouldn't work.

2) We've tried this before, it didn't work.

3) Doesn't really fit our sales model.

4) It's not appropriate for our industry.

5) It might work for tiny/small/large/huge companies, but we sell to tiny/small/large/huge companies, and it won't work for them.

6) Our investors/board would never agree to it.

7) It might work, but we can't afford the risk that it won't.  (Note: When someone says “it might work…but…” they're almost always thinking: It won't work)

8) Our team/plan/pitch-deck is not really setup for that.

9) We could try it, but it's a distraction.  (Note: This often means “I've already decided it's not going to work, but I can tell I need to convince you we shouldn't try it…”)

There are many, many more reasons why any given idea won't work, but the above are a sufficient sample for this article. Oh, and by the way, I have at various points in time made all of these very same arguments myself (“I have met the enemy” and all that)

2 Mental Exercises To Try

Now, here are a couple of mental exercises to try when you or you or your team is stuck.

Exercise #1: What if I told you that it's working really, really well for XYZ Company?  How do you think they made it work?

The idea here is to assume the idea is good and has worked for a company very similar to yours.  Then, ask yourself (or your team):  Now that we know it worked for them, what do we think they did to make it work? 

What this does is mentally nudge you to think about how to work through whatever the obvious limitations to the idea already are.

Example: I know that nobody in our industry uses a freemium model because the infrastructure/support costs are just too high.  But, we just learned that XYZ Company is launching a free version.  What do we think they did to make it work?

Exercise #2: What if we had the proverbial gun held to our heads and we had to do [x]?

The idea here is to assume/accept that the decision to implement the idea has already been made — presumably by some higher authority.  Now, assuming that, what would you do to make the best of it?

Example: Our major investors just told us that before they can agree to funding our next round, we need to build an inside sales team.  They think inside sales teams are the bomb.  We can't afford not to listen to them — what do we do to make the best of the situation?  If we had to build an inside sales team, how would we go about doing it?

Note:  In neither case am I suggesting that you mislead your team (or yourself, in case you're like me and have conversations with yourself late at night).  These are meant to be mental exercises, just to help drive discussion and analysis.  Though I'll confess, there is a small part of me that wonders what would happen if one did make the hypothetical seem real (at least for a short period of time).

What do you think?  Any mental tricks or tactics you've used (or thought of using) to help break-through conventional thinking?

Topics: strategy
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