At Berkeley, judging at panel for Berkeley’s Mobile Startup Challenge

Fun stuff!

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3.5 screens & loving it

Lenovo T410 / Windows 7, across 3 monitors, plus an Ipad

Got my #geek on

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awesome game, great win

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Let’s go Steelers!!!

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took boys shopping today. very pleased that they seemed to enjoy REI as much as gamestop.

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Thru the looking glass: Fund-Raising Lessons

Handling QA in investor pitches

Udemy’s Gagan Biyani wrote a super useful, practical guide on fund-raising lessons learned.  Gagan is a great Silicon Valley startup CEO: he’s tireless, he’s persistent, he’s nice, and he’s adaptive.  All that comes through in his post.  Give it a read here

He set an example that I wanted to follow on slightly with some of my own lessons learned and lessons borrowed.  I’ve gained the opportunity to participate in the fund-raising process from a few angles. As an entrepreneur, I’ve raised money for my own company, Moonshoot.   I’m also at times a venture capitalist/investor at BlueRun Ventures, so I see things from the other side of the table too.  

I’m putting together a series of posts, which aim to share these learnings.  I’m going to start this series with one of the most important –and under-discussed – elements of the fund-raising process: answering questions.  

“Say it once.  Say it well.  Don’t say it again.”

I attribute this quote to one of my best friends, Nils Gilman.  An intellectual historian, published author, and polymath, Nils is a fountain of knowledge, thinking and ideas.  He can also flat out turn out well-written text at a factory pace—it’s crazy.  He uses the above adage, in coaching me on writing.  I apply it to what we say, specifically when answering questions in a pitch. 

Why questions matter

Most fund-raising posts will focus on pitch decks, meeting etiquette, etc.  All that stuff is useful.  In my experience though, a key skill for any founding team is how to answer questions.  Investors want to ask questions to probe more deeply and to see how you respond.   In addition to getting us information we want, asking questions provides a different lens into the thinking and quality of the founding team.  How you answer questions conveys a great deal about you, your team,  your credibility, your command of data, etc.   You may not win by answering questions well; you risk a lot by answering poorly.

Where to Start

As answering question is more improvisational, it tends to get less attention than preparing a pitch, getting the deck in shape, etc..  Don’t ignore questions though—spend time thinking about how you want to answer questions.  Nothing is more painful than presenting a great pitch, only to feel as though you gooned a few key questions and lost your credibility in front of a potential investor. 

I recommend Jerry Weissman’s book, In the Line of Fire: How to Handle Tough Questions.  Jerry is a friend, mentor and teacher.  He’s one of the very best in presentation training and skills.  His thinking and exercises on Q&A (and among presentation planning) are among the best.  Get his book here.

I also recommend writing down the top 10 questions you expect.  Figure out how you want to answer them, and answer them that way.  As you go through pitching, write down the questions you’re getting, along with the answers you provide at the time.  Assess whether there are better answers you could have provided, and add that to your repertoire.  Evolve this so that as you do this more, you’re ready.    

My Observations

Few founding teams handle questions extremely well.  Many struggle with basics—hearing the question asked and answering.  For example, if an investor asks you if you’ve raised previous money, a simple “yes, we’ve raised $80K in friends and family” is a fine answer.  Instead, often there’s some whole discussion of who gave you money, when all it came in, why you took it, etc.   TMI.  Understand the question being asked, and answer it.  Remember the adage:

Say it once.  Say it well.  Don’t say it again.

Focus on this, and you’ll be in good shape. 

As you are focusing on this, I’ll add the two most common breakdowns I see in founders answering questions during a pitch.  Though different, they’re related.  Here are the two most common problems I see in answering questions in a pitch:

Answering about the unknowns

Founders are dealing with big unknowns.  Known unknowns and unknown unknowns.  As someone assessing whether I’d invest, I know you’re dealing with unknowns.  Its generally fine to say, “I don’t know, and here’s my plan to learn/figure out.”  So long as this is credible, that’s fine. 

There are two cases where that does not work.  First, you say you don’t know, when I think you reasonably should.  For example, this summer I spoke to a mobile location-based platform company seeking investment.  The exec with whom I spoke hadn’t heard of FourSquare.  This was unacceptable, as this person should have known of them—something he should have been able to figure out. 

The second is where you dress up the “I don’t know,” in a bunch of bullshit.  I have sympathy for this mistake.  As a founder, we want to know everything on the business.  We don’t want to feel like we don’t know an answer to a question.  We may even have some decent hypotheses.  But if you don’t know, you don’t know.  Just say, “I don’t know yet.  I plan to figure that out this way.”  BS is pretty easy to identify and its hard to watch.  I understand the temptation, but avoid. 

Answering about the knowns. 

If founders talk too much about what they don’t know, they are also prone to talking to much in answering questions on details that they do know.  The problem here is lack of empathy.  Investors are flying at a different altitude than the founder.  Founders have everything invested in a company, and are very close to the businness.  Investors are much more removed—trying to assess in a brief conversation the viability of potentially investing  money in a venture.  An investor is flashing through in his/her mind whether the market, the team, and product could be a fit.  This mismatch leads to times where an investor can feel a pitching founder is just off on a tangent and “in the weeds” to a degree that they won’t be able to manage or lead a company.   

Sometimes an investor really is interested in getting down into the weeds, but that’s pretty rare.  As a founder, you should know whether the investor is asking for that detail—if yes, then go into weeds.  If not, hold back. 

I posit that when most potential investors ask a question, they want to see whether a founder can understand it quickly and credibly clarify the essence of what I’m asking.  Sounds easy; hard to do.  Most of us are so close to our specific worldview that its difficult to context switch and communicate at a more bubbled up level. 

For example, I spoke by phone with the CEO of an outstanding company this summer.  Very clearly, they’d built a better mousetrap.  The issue was, no question I asked, regardless of how basic, had less than an 8 minute answer.  This did damage.  I literally got spooked because the executive’s answers were too disjointed and long.

As I reflect on this, it could well be that these symptoms are related.  As founders, we want to hide the stuff we don’t know and expand the stuff we do.  The result is unsurprising.  For stuff we don’t know, we retreat and hem and haw and deflect.  For the stuff we do, we want to expound and show you in 10 different ways why we know this particular thing.  The problem is, both are exactly the wrong approach.  Which leads me back to the mantra I’m repeating…

Say it once.  Say it well.  Don’t say it again.

In conclusion, I’m kicking off my series on pitching observations with a (hopefully) useful primer on answering questions.  Think about this.  Write down key questions you expect and prepare answers.  Track the questions you get asked and how you answered them.  Be mindful of whether you’re more effective saying “I don’t know, but…” or answering what you do know. 

And good luck.  Happy hunting. 


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Pitch Advice from Jerry Bruckheimer

2010 has been a busy year for me.  We launched Moonshoot in Japan, and that’s going well.  I’ve done a few talks at the Founders Institute, some friends of mine and I built Smackdaddy for the IPhone, and I’ve begun helping out part-time at BlueRun Ventures.  All in all, a busy 3 quarters so far, which has led to a dearth of blogging.

To re-enter the blogosphere, I’m planning on spending several posts sharing learning I’ve had in the fund-raising process–both as an entrepreneur (by day) and as a vc (by night).   This first one is a story I’ve told analogue about 5 times in the past 2 weeks, so I figured I should probably post it to the blog and share it potentially more broadly.  It has to do with a key reality in pitches or startups that you need to think about when you are getting started or pitching.  Namely, is the business one that’s going to emotionally draw someone in?

My inspiration for this emotional connection is uber-producer Jerry Bruckheimer, whom Wikipedia credits with over 40 feature film productions.  His movies rock, I love them.  Years ago, I recall reading an interview of his, which I sadly can’t find, in which he was asked how he knew what was good or not good.  He graciously claimed that he had no idea what would catch on and be a hit and what wouldn’t.  What he did know, though was emotionally what connected with him–and he had some funny quote about how he felt a tingle in his chair when a movie really grabbed him.  This ‘a**-grab’ was the thing that told him whether the movie was good or not.  A totally emotional, non-scientific approach.

In the startup world, there is an element of this that’s important.  Sadly, this is sometimes overlooked.  VCs are looking for massive returns and low friction, etc.  Entrepreneurs are looking to make meaning or build something people want, etc., etc.  And while both of these points are useful to think about, at some point, you had better look at a business and be emotionally drawn to it.  At the end of the day, whether you are an investor of money (a VC) or an investor of time (a founder or employee), its important to contemplate whether you think the business has any emotional draw to you (or anyone else).

If you don’t feel the pull, that’s fine, the business may still be a monster, but I’d say stay away.  The work is too hard, the days too long, the competition too fierce for you to be ambivalent on the emotional draw of a business.

More often than I’d like to, I see businesses where teams have built a solution to a problem that does not grab me (or often, their founders) emotionally.  If you love your business, and I don’t, that’s fine–s*** happens, and that’s fine.  If you don’t love your business, trust that others will know.  In that scenario, why do that.  Let it go, don’t settle.  Find the business that gets your spine tingling and give your all to that.

Welcome back to blogging.

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