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Bottlenotes: Silicon Valley Internet Start-Up Meets Wine Industry in Chicago

Business students in all the top MBA programs experience what’s called the herd mentality during recruiting season. And although many fantasize about risking it all to become the next great entrepreneur, in the end most still head to corporate America for a safer job and a guaranteed pay check.  But every now and then there are exceptions. Mavericks that lead with energy and idealism. Leaders optimistic that with passion and hard work, they can build their own empires.  And I have the great pleasure of knowing one of them. And just this past Friday, I spent the evening at Chicago’s Museum of Contemporary of Art (MCA) with leading entrepreneur Alyssa Rapp at an event put on by her internet start-up company Bottlenotes.

Meeting up with Alyssa at the Chicago MCA wasn’t by happenstance. In fact, I first met Alyssa in 2006, when I lived in Palo Alto after graduating from Stanford.  As a fresh, young graduate looking for new and exciting opportunities, I had the dual goal of not only working full-time at a start-up consulting firm but also rolling up my sleeves at a real start-up.  So I sent a few emails and made a few calls, and I eventually found myself working with Alyssa in the evenings and on weekends, when I wasn’t in the office. And not only did I gain have exciting and interesting experiences working at a internet start-up, but being the Anthropologist I am, I also paid attention to the things Alyssa did and tried uncovering the skills it takes to be an entrepreneurial CEO.

And after doing similar research on other entrepreneurs over the years, I’ve found that to be truly great, entrepreneurs usually have a unique combination of skills – passion and creativity, an ability to take risks, the capacity to make decisions quickly, and also an ability to balance competing priorities, especially in the early stages.  These are all traits that aren’t necessarily typical for JDs or MBAs. In law school, JDs are taught to identify risks and mitigate them. They’re also taught to analyze issues from both sides before making decisions and to focus intensely rather than juggle multiple tasks. On the other hand, MBAs are taught to be a bit more decisive. But because in business school quantitative skills are king, MBAs tend to rely on supporting data rather than creative thinking or intuition. Harvard Business School likes to say that it trains students to get in the habit of making decisions.

But in my view, being an entrepreneur is a bit more nuanced than both of those. Not only must they perform analysis and assess risks but they also have to do it real time, so they are better positioned to identify and seize opportunities immediately when the market changes.  That also means they have to be fearless and quick to act, not always out of “habit” but often times using intuition or gut feel. So entrepreneurs tend to have a higher tolerance for uncertainty and an uncanny ability to focus on the details while always honing in on the bigger picture. A herculean set of tasks by all measures.

And it looks like a lot of these traits have paid off for Alyssa. And last night the good people of Chicago got a glimpse as the MCA was jam-packed withwell over 800 people, a number which would have been significantly higher if the event hadn’t sold out due to the MCA’s capacity.  It was great to see Alyssa again and to see how successful her company is becoming. It was also great to see a Kellogg alum and Bottlenotes COO who I’ve gotten to know over the past few months, not to mention meeting dozens of new people at the event. I even ran into a good friend of mine from undergrad and into a Northwestern JD-MBA from the class of 2008.

In the end, I’m glad Alyssa was bold and decided to be an exception after graduating from Stanford Business School.  And as a result, today she’s building a business that provides a unique product, delivers a highly customized service, and perhaps most importantly that brings thousands of people together from across the US to share enriching and memorable experiences.  Bravo Alyssa and bravo Bottlenotes!

I hope that all my readers take a second to check out her company.  Click here to learn more about Bottlenotes. And if you’re up for a bit more reading, click here for an online interview by Start-up Stories, and here for a podcast interview on iinovate.com.

Thanks for reading everyone!

Tags: Business School, Conference, Kellogg, Law School, Networking

Day Two of Latino Legacy Weekend

Passion. Storytelling. Leadership. Those are a few of the adjectives that were brought up today when the panels, guests, and speakers talked about changing the game for latino professionals in America today. And they quickly caught everyone’s attention, not only to keep us engaged in the panels today but also to help Latino Legacy Weekend pull off its second act this weekend.

Just minutes ago, we finished our second and final full day here for Latino Legacy Weekend. And as I suggested above, the event was very well executed. Similar to yesterday, the panels were exciting, engaging, and full of great and highly accomplished speakers. Unlike yesterday, though, the panels today were more panel-like, where they were more interactive and also left a more time for Q&A after the presentations, which I personally enjoyed.

In the first panel about political activism, we had a highly accomplished list of legal and political heavyweights, who chimed in on things like passion, leadership and accountability. The topic of storytelling also came up, and a Chicago Super Lawyer, Christine Martini, discussed the importance of a compelling message and telling a good story, especially for someone who may want to take on a political leadership role. In another panel, the speakers talked about the role of Latinos in society today. A current BCG consultant mentioned that it’s not enough to lead by example today, and that we all have to go beyond our comfort zones. They also talked about mobility and sharing information.

I personally liked the panel on children and youth, where we had a highly diverse panel, including a health service professional and DMD, as well as a couple of professors, including one from Stanford who discussed a 15  year test about high school graduation rates. My favorite panel, though, might have been the one on media in a panel later in the day, namely because media is one of my biggest interests, given I maintain my website and contribute to a few others. In some ways, the media panel did a good job summing up the weekend, as they gave a lot of ideas about being vocal and sharing information, learning how to mobilize a campaign, reaching out to more people, and building connections with other leaders in the community. And they talked about all of this in the context of working together as a team, using the example of becoming a “chorus of voices.”

In the end, my experiences at the conference reinforced my belief that teamwork is absolutely critical.  That a team working together can accomplish more than the sum of its parts and that to achieve our highest potential it’s critical that we leverage everyone’s diverse skills and talents to achieve common objectives.  So I’m glad that everyone’s still fired up about the great weekend. I hope that we’ll all stay in touch after the event. And after chatting with a few of my new friends, it sounds like everyone plans to collaborate together on some of the world’s most important issues in the future.

Thanks for reading everyone. And stay tuned for LLW 2011.

Tags: Conference, Diversity, Leadership

Day One of Latino Legacy Weekend

Many people have good ideas, but few are willing to put themselves on the line for them. Often times they’re afraid of rejection or they fear the hard work it takes to achieve success. And other times, they’re simply afraid of failure, especially when other people are watching.  On the other hand, there are also leaders who create extraordinary results because they are deeply passionate about their cause. These leaders work tirelessly to bring others together and connect them with their mission and to steer their organizations to new heights.  And that passion was not only evident, but also contagious on the first day of Latino Legacy Weekend.

Despite long exhausting travel schedules and work schedules, not to mention sentiments during the current economic crisis, a sense of excitement filled the room from the very first minute at Latino Legacy Weekend. Leaders from every industry filled the room – law, business, finance, public policy, politics, academia, government, and education. It was good to see so many like-minded people together with the mission of “transforming power of ideas and building bridges across professions, ideologies, and regions.” And that certainly happened today across a series of panels, speeches, and collaborative discussions.

In one panel, professionals from California, Texas, and New York talked about challenges in the education space. In another, a Northwestern Professor collaborated with an employee from Goldman Sachs and another professional from Municipal government to talk about immigration. This was especially compelling considering we were at a Latino Conference, and considering that I am originally from Arizona, where immigration is the big issue of the day.

I was on the Business and Finance panel, which came next. Ironically this session was lot less technical than some of the others, despite being the finance section.  One former BCG consultant talked about how important it is to following your passion, while a fellow Stanford grad that I met there talked about finance and public policy. As for me, I gave my pitch about why it’s so important to share information not only with each other but also with the next generation behind us. At the last minutes, I decided to divert quite a bit from the presentation I prepared, not only because my prepared one was a bit long but also because I wanted to talk more from my gut and discuss a topic that I’m passionate about. And in the end, a few of the participants told me that they liked my talk, so I’m glad I decided to change things up.

We also had a panel on Politics and on Corporate America, both of which went well. The common theme between these two is that we need more Latino Leadership in these areas – at the executive level, the board level, and high level political roles. As part of that we talked about the low number of CEOs and about the prospects of a Latino president in America’s future. But we also discussed how that transition will not be easy, and we talked about leadership strategies that we need to keep in mind as we navigate the business and political spheres.

In my view, that’s because public issues are inherently ambiguous. Leaders must weigh tangible issues against intangible principles, account for diverse views and beliefs in the community, anticipate skepticism from just about everyone, and balance all of that to eventually take a stand.  Leadership is less about command and control than it is about bringing people together and building consensus. To do that, leaders must not only understand the complex issues but they must also have a compelling message.

And in the end, day one of the conference was filled with compelling messages and was inspiring. And the night was also fun. We had dinner at Star of Siam, a Thai restaurant in Chicago, and after that had a fun night out.  I look forward to day two of the conference.

Stay tuned !

Tags: Conference, Diversity, Leadership