Today, I spoke to Randy Haykin, who teaches New Venture Finance and  Innovation/Creativity at the Haas School of Business, UC Berkeley, while working hands-on with portfolio companies of his venture fund outlookventures.com and his angel investment group, and he was Yahoo!’s original VP Sales and Marketing. In this interview, Randy talks about entrepreneurship, how he built Yahoo!’s brand, how entrepreneurs can develop their own brands, and much more.

You’ve been investing in early-stage startups for the past 15 years and now teach Innovation and Entrepreneurship at UC Berkeley’s Haas School– in your opinion what makes one entrepreneur more successful or innovative over another?  What’s at the core of the successful ones?

The class has been an amazing experience for me and the students – we’ve had authors and guest speakers (founders/leaders) from Google, Netflix, Pixar, Tesla Motors, Electronic Arts, Reply, LesConcierges, and many repeat entrepreneurs.  I posted a great overview of the class details at: http://bit.ly/axNzUO .  Last year, I also wrote a post on the things that seem to set the successful entrepreneurs apart from others at: http://bit.ly/9DTBEK . One major key I’ve noticed has to do with FAILURE. The best entrepreneurs seem to (a) encourage people to take risks, (b) allow room for failure, even celebrate it if it is a learning experience, and (c) pick themselves up and get going soon after a major set-back/failure.  There are, of course, plenty of other things we’ve noticed. I’m interested in writing a book someday on this topic.

You were the original VP Marketing & Sales at Yahoo – was Yahoo a brand when you started there? What did you and the team do to turn it into such a recognizable icon over time?

Yahoo had just been chosen as the company & URL name about 2 months before I started at Yahoo as VP Sales/Marketing. In essence, we started at “Me 1.0” – the early focus was on Jerry Yang and Dave Filo, the youthful founders of Yahoo – who essentially had two very good things going for them – an understanding of the Internet enabling technology (Dave) and what emerging Internet consumers wanted (Jerry).  I crafted a strategy to bring their story to the world.  We worked with Newsweek, Time, Rolling Stones, Wired, Fortune, People and many others to craft an image of their “Stanford school roots” and they emerged as representatives of the Internet Age.  Back then we didn’t have social media to help spread the word, so I  partnered with key players like Reuters, Softbank, Microsoft and Netscape to get early distribution and attention.   We hit the wave early and took it into the shore.

We also leveraged an ideal URL and word “Yahoo” – as you may know, YAHOO was initial conceived as an acronym (Yet Another Hierarchical Officious Oracle) and originally came about during a dormitory discussion with Dave, Jerry and their friends at Stanford.  But once the company was funded and was beginning to get millions of hits per week, we realized we had a very unique word to work with and turn into a full-fledged brand.  First, the word has universal appeal globally – a nice advantage that allowed us to brand Yahoo into Japan and Europe quite early.  Second, the idea of “yahoo” meaning “I’ve found it” or “eureka” seemed to fit.  Graphic Designer @daveshen was the original creator of the yahoo logo and colors – which 17 years later still survive (purple, blue, yellow).

Do all entrepreneurs have to have well-known brands or develop them?

Let’s first look at the entrepreneur HIM or HERSELF as the brand. I’d say the answer is “Yes”.  The entrepreneur needs to develop a “persona” around their talents, skills, tract-record, relationships and even thoughts (if they are the expressive type).  For example, when I am investing in early-stage companies the first thing I do after meeting an entrepreneur is search LinkedIn, and Google to find articles on the person or his/her past projects and companies. If they’ve branded themselves well as a person, it’s easy to find information (in fact they are probably CONTROLLING that information if they’re smart about it) and it paints a picture to me as an investor as to whether or not this is a person I’d like to work with.

From a company perspective, I think the answer to this question really depends upon the growth stage that the company is in,  the marketspace and target customer that the entrepreneur’s company focuses on, and even the company’s business model.  Take a market that is highly competitive – I’d argue that early branding is crucial because you only get a certain number of impressions with your buyer or consumer and you are being compared with others. In a marketspace that is less competitive, you can take your time building brand one customer at a time. Another example, a B2B company that white-labels its products has less reason to worry about its external brand – it is mostly about relationships.  The salesforce substitutes for a recognizable brand.  A consumer marketplace requires a more visible brand.  Both B2B and B2C ultimately need a brand, but I’d argue that the B2B player can afford to wait until puberty to push on this front.

Will an entrepreneur have a better chance at getting venture capital if they’re well known?

I think in certain markets that the entrepreneurs with better online reputations and “infamy” are in actuality more likely to be funded, as long as they are being praised on the Internet and have clearly been involved in many things.  I see several examples of today’s entrepreneurs who started as Internet bloggers and are now either powerful as entrepreneurs or as venture capitalists. For example: Om Malik.

However, the wide bulk of entrepreneurs have a reputation from the COMPANIES they’ve been part of in the past and the ROLE they’ve played – not so much their online persona.  Of course, in the consumer space, having a following, like the lucky guys at @joelcomm or @danschawbel or @tonyrobbins definitely helps in launching new opportunities because you can broadcast the newest ideas to a wide audience overnight…and some angel or VC is likely to see that broadcast.

What disadvantages do entrepreneurs have if they haven’t started a business before?

The biggest disadvantage, in my opinion, for an entrepreneur who hasn’t started a business before is lack of pattern recognition. Those of us who have done it several times begin to anticipate the outcomes of certain actions.  Knowing what is likely to happen saves time an unneeded learning/experimentation.  This is helpful when you are working with limited resources (funding or people) to prove yourself.

Of course, for some personality types (particularly those born with “chutzpah”), lack of experience could also be a PLUS. Sometimes not knowing what you don’t know means that you will attack problems without bias or take on serious challenges without realizing how insurmountable they may have been for others. One of the keys I’ve found to great entrepreneurs over the years is that they create an environment that is FEARLESS – in other words, they encourage experimentation and when failure occurs they say “that’s OK, you tried and you learned something…just be sure you don’t get him with the same failure a second time.”

You are doing something unusual with Twitter and Facebook that I’ve not seen before – called “The Gratitude 365” project – can you tell us a bit about that?

I was in the process of working on my New Years resolutions this year, when I realized that my top desire/goal for the year was FOCUS ON THE PRESENT …something that sounds simple, but is very hard to do on a regular basis!  I figured that if I could focus on the present, I’d be a more pleasant person to be around, would notice things that I could be thankful for, would be in a more positive “glass is half-full” mindframe.  So, on Jan 1, I sent out my first “Gratitude 365” (see: http://bit.ly/aR7DkT)  tweet and FB post.  I’ve since expanded it to include my website and LinkedIn as well, so pretty much friends and colleagues can see it on all my networks.

Each day since Jan 1st, I’ve posted one thing that I am GRATEFUL for, and an associated image with it (see: http://picasaweb.google.com/haykin/365DaysOfGratitude#) . Sometimes the image is a simple photo of an event or person that I’ve enjoyed. Sometimes it’s a bit of a project – using Photoshop, my Canon camera, items from others, etc.  It certainly is working, as I now find myself looking around nearly constantly for things to be grateful for. Also, I think this is building my personal brand up a bit, as I’ve gotten many responses from around the world about the project.

Why are you inside a lightbulb on your website (http://haykin.net/haykin_bio.html)? Is that your brand?

The lightbulb with the seedling inside (see http://haykin.net/) is my brand. I’m in the business of designing, assisting and launching ideas and companies.   I’m also in the business of growing young people (as a teacher, parent and life coach).  The symbol stands for the core of what I’m all about – IDEAS on one hand and GROWING THINGS on the other hand.  Think of the bulb as the “incubator” for ideas. The ideas start off as seedlings, I spend lots of time nurturing my projects, the projects are fed with plenty of nutrients and light, and then at some point they outgrow the lightbulb and we transplant them into a bigger pot.  I have a nickname around my home town: The Gardenator.  It’s a combination of “one who makes things grow” and “Schwartzenagger attention to completion” – that’s what you get when you turn a Harvard B-School grad into a gardener!

The version of the lighbulb with me inside is to poke fun at the brand.  You have to get INSIDE the brand to really appreciate it – so that’s what I’m doing in the lightbulb…don’t ask me how they got me into that bulb in order to take the photo…

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Randy Haykin is a serial entrepreneur, venture & “mentor” capitalist, educator, and artist based in Northern California.  He presently teaches New Venture Finance and  Innovation/Creativity at the Haas School of Business, UC Berkeley while working hands-on with portfolio companies of his venture fund outlookventures.com and his angel investment group haykin.net. Mr. Haykin is known for his expertise in Entrepreneurship, Creativity and Innovation which he blogs about at innovationsparks.com and he applies lessons from some of the world’s top entrepreneurs to his Board and investment work.  He began his career at Apple Computer and Paramount/Viacom and was Yahoo’s original VP Sales and Marketing.  He has also held director roles in a variety of consumer, b2b, enterprise and infrastructure companies.  He is a graduate of Brown University and The Harvard Business School.