Stamford Startup Weekend: Random Thoughts

I spent almost all of my waking hours this past weekend at the Stamford Innovation Center serving as a mentor during their Startup Weekend.  The concept was started by a non-profit in Seattle and last year, over 400 weekends were held in over 100 countries.  Here’s how they describe the idea:

Anyone is welcome to pitch their startup idea and receive feedback from their peers. Teams organically form around the top ideas (as determined by popular vote) and then it’s a 54 hour frenzy of business model creation, coding, designing, and market validation. The weekends culminate with presentations in front of local entrepreneurial leaders with another opportunity for critical feedback.

I’m guessing around 25 people presented Friday night, 10 ideas were selected for work over the weekend and four winners were selected Sunday night.  I’ve now done this a few time and after spending all this time with these entrepreneurs  budding entrepreneurs and entrepreneur wannabes, I walked away from the weekend with a variety of random observations.  I’m not going to so much opine on the idea presented — some were really great, some were pedestrian and some were just strange — but rather hopefully I’ll provide some insights to help the next roster of weekend participants. For me, I know it’s politically correct to talk about giving back to the community and mentoring the next generation but the truth of the matter is that no matter why you’re here, you’ll get more than you give.  I came away with new ideas, new energy and new friends.

If you’re wondering whether this is something you should do, my answer is an unequivocal and enthusiastic YES.  Seeing the progress in 54 hours from loosely formed idea to final presentation to the judges shows just how much you can get done in a short time when you focus.  Where else in a weekend can you get:

  • A team of people to help you build your company,
  • Test an idea with a diverse set of experts and fellow entrepreneurs,
  • Build a prototype or even start coding,
  • Iterate, pivot, change, enhance, improve, and improve some more,
  • Get a logo (from the wonderful father and son team of Alex and Ryan Virvo of the Gorilla Agency),
  • Find your calling (some people came not to present ideas but to find a team to work on), and
  • Make new friends.

While inspired by the Startup Weekend, the insights below are really relevant to everyone, startup to Fortune 10.  Herewith some observations:

  • Presentation skills matter.  Back in my Gartner days, we asked attendees to rate presenters on quality of presentation skills vs. quality of content.  With extremely rare exceptions, if you presented well, clients thought your ideas were great.  If you presented poorly, even using the exact same material, clients thought your ideas were poor.  It’s clearly not my issue but presenters throughout the weekend had problems with volume.  If I can’t even hear you, you’re already out of the running.  Don’t read your speech.  Unless you’re Presidential candidate good, reading is devoid of passion, spontaneity and confidence.  If you’re not confident in your message, I’m not going to be.  Almost as bad, don’t read your PowerPoint.  Your audience is capable of reading; complement your PowerPoint slides. But don’t put so many words on your PowerPoint slides that I’m reading the slide and not listening to you.  There are teams that I still don’t know what they do, not because they have complicated ideas but because, even with a microphone, I couldn’t hear their words.
  • Tell a story.  Entrepreneurs love talking about features and functions.  To the rest of the world, that’s dreadfully boring. Instead, imagine you’re a story teller.  What are the elements of a good story:  an antagonist, a protagonist, a problem and a solution. The good guy wins. Capture my attention with a problem before you go into a solution.  It’s not good if you’re trying to solve a problem no one has. I always adhere to a simple rule:  no matter how good you are, the audience is only going to take away three things from your presentation.  Make sure you’re always bridging back to those three points.  What’s the problem you’re solving, how big is that problem and what makes someone believe you’re the one who can solve that problem. And when it comes to Q&A, it sounds funny but don’t answer the question.  Understand the questioner’s real objective — to throw you off course — and use each and every question as an opportunity to bridge back to one of your key points.  Imagine that one of  your key points is “we’ve got a seasoned team.” Someone asks you “can’t Google put you out of business tomorrow?”  If you actually answer the question, your two choices are bad.  “Yes” isn’t actually awe-inspiring and if you believe “no,” you’re kidding yourself (and showing yourself as out of touch to the questioner).  Instead, what if you went “for a lot of people, that would be a real challenge but we’ve got a seasoned management team who has been through this before and we successfully navigated those waters with one IPO and two acquisitions.”  Notice, I never answered the question.  Instead, I bridged back to my talking point.  I spent some amount of teams trying to focus their pitches.  They were down in the weeds – way down in the weeds — and the challenge was to elevate features and functions to a story.
  • Listening skills. There’s an old maxim, “no one ever learned anything while their lips were moving.”  There are probably some ideas out there that are so good that they don’t need any further insights.  I’ve never heard any of them.  Instead, once someone understands your idea, stop convincing and start listening.  You want to encourage feedback, not challenge observations.  Sure, if someone has something way wrong, you should figure out how to address that issue (and how it is you led them to this wrong conclusion) but for the most part, there are credible alternative positions and you’ll be better if you intimately understand the objections of your target customers and partners, rather than trying to stifle and silence them.  I was in one three-person conversation and the entrepreneur spoke approximately 18 of the 20 minutes we “talked.” Not surprisingly, his project didn’t make it to the weekend round.  And if it had, you can get his would not have been one of the teams I sought out to help…if indeed he could have maintained the team through the weekend.  (Teams do suffer departures, defections to other teams and even occasionally they spawn other takes on the original business problem.)
  • Understand your business. The winning entry, ArtGoGo is not an art marketplace but rather an initiative that is aiming to ease the path to market of starting artists, better democratize the art acquisition process and address some real market inequities.  Do you realize that gallery commissions for many artists are 60% or more of the purchase price of the artwork?  The person in the $2,000 suit gets 60% of the selling price.  The person in the $30 jeans who spent three months actually making the art gets 40%.  Understanding your real business will help inform your business and open up natural extensions to your original idea.  Another winner, Secure Your Own Device, doesn’t offer security software.  Instead, they make it easy for you and your kids to remain safe from real threats. Some of this goes back to the storytelling point.  You’re not just a product or a service. Instead, you’re solving a real customer problem.  That’s the objective of your business.  The product or service is merely a vehicle for accomplishing that objective…and in the future, you may discover you have more ways to do that.  My favorite example of this is Hallmark greeting cards. Over five years ago, I had a meeting with them and they revealed that their market kept shrinking (duh!) and the average age of a card buyer kept going up (then around 62).  Following that trend line, their last customer will die some time in 2023.  I asked a simple question, or so we all thought.  “What business are you in?” Their (wrong) answer was “greeting cards.” I said “you’re actually in the gift conveyance or milestone celebration event.”  Hallmark’s revenue last year was right around $4 billion.  The total affiliate marketing industry last year was right around $4 billion.  Guess whose number is growing and whose is declining.  And how much bigger might that number have been if Hallmark had gotten behind it instead of leaving it to a series of companies most of you have never heard of. The fourth place winner of the Weekend was a team called CartWheel whose whole idea was to enable companies to collect a portion of the affiliate fees generated by employees who shop via their corporate networks.
  • Horse vs. Jockey. It’s an age-old issue:  in a competition like this (or when seeking a funding round), are people betting on the horse (your idea) or the jockey (you and your team).  No idea is so good that a bad team can’t screw it up. Yes, you want your idea to be as compelling as possible but if you’re not thinking about how you convince your audience (here, a judge, sometimes a VC, a potential customer, supplier or partner) that you’re someone I want to do business with/bet on, you haven’t completed the job.
  • Make Your Market Sound Big. I actually talked with one guy who said his total market size was $1 million (small) and that $800,000 of the market was already spoken for (saturated). I was waiting for the “here’s how, why and when the market’s going to grow” but it never came.  Needless to say, he didn’t make it to Saturday.  The ArtGoGo people started talking about how 90% of all artists basically sell nothing.  Not helping your case!  Instead, talk about how many people buy art (millions), the size of the high end market ($billions) and now I’m starting to see dollar signs.  Give people confidence you’re addressing a large market and that you understand the parameters of that market.  “My friend the starving artist thought this was a good idea” is not a market-validating input.
  • CompetitionAll too often people answer that one with “none.” This is not a good answer!  If no one else sees the opportunity you’re seeing, it’s possible that you’ve identified an untapped market.  It’s much more likely, however, that seven people have tried to do what you’re doing and have failed miserably and that there are three others who are doing exactly what you’re doing and you’d better relentlessly out-execute them.  You do have competition.  Even if it’s just inertia behind an existing approach.  Make sure you understand it. Related to this is the notion of the first-mover advantage. I’m still waiting for someone to give me a compelling example of that.  Microsoft was in tablets and smartphones before Apple.  How’s that working out?  More often it’s a first mover disadvantage. The fast follower can learn from your mistakes, better time the market and capitalize on your first move.  Competition is good. Show how you’ve learned from it and how you can win the competition.

If you’re a budding entrepreneur (of any age), a startup weekend is a great vehicle to take a fledgling idea from concept to concrete in a weekend.  So many of these things languish as “in my spare time” or “maybe next year” projects.  Most I’m sure never go anywhere.  Getting this much value and making this much progress in a single weekend is an incredible experience.  One of these days maybe I’ll propose an idea.  In the interim, being a mentor was a great experience.  I met some really interesting people, helped a few, learned a lot, had some fun and had some beer.  And best of all, when I went up afterwards to congratulate the winner, she asked me “could I hug you?” That’s better than any money I could have gotten over the weekend.  Sort of.