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Startup lessons from Ben Silbermann, Founder and CEO of Pinterest August 30, 2012

Posted by johnvrionis in 2012, hiring, management, start-up, Summer Program.
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As a part of our Summer Fellowship Program, we bring in influential speakers from around the valley each week to share their insights, lessons learned and tips with our teams.  The program has now been in place for six years, so with recent fellowship classes I have been fortunate to pull from our list of alumni when curating the speaker list. One of those alumni, Pinterest CEO Ben Silbermann, was generous enough to join us this past week for lunch with our fellows and alumni from past years.

During lunch, Ben shared details of his background and thoughtfully explained the journey of how he came to be CEO of one of the hottest startups in the consumer internet space.  He also shared a number of insights and lessons which I think we can all learn from:

Hire Great People, regardless of if you have a defined role for them:  Ben shared that one of the things he is thankful he did in the early days was to hire people that he thought were great people even before he knew exactly what their role would be. Great people, he explained, can add value in various roles and often provide key solutions to problems that arise throughout your lifecycle.

Learn from No:  Whether you are seeking funding, making offers to potential employees or trying to build partnerships, as a startup you are going to hear the word no a lot.  What makes Ben a great entrepreneur is that he recognizes that most of the time, people are saying no for a good reason.  He had the patience, self-awareness and intellectual honesty to evaluate the situation and make the necessary changes.  Whatever the reason for No, Ben stressed the importance of using it as opportunity to learn and to correct so that you are moving your company into a position where you can start getting some yeses.

Decide what will make you happy and commit 100% to doing it:  One of the things Ben said he learned early on was that while being an entrepreneur meant that he had control over what he was building and doing, it also meant that he lost control over a number of things like a steady paycheck or the resources of a large organization.  But, ultimately, the tradeoff was worth it for him to keep going.  His advice to the group may seem simple and obvious, but it can be hard to follow!  He was convincing – you have to find what makes you happy, because ultimately, that is the person you have to answer to first.  Building a startup is really hard, but if you are doing something you love or building a product you are passionate about, it is one of life’s greatest rewards.

Foster your co-founder relationships:  Like any relationship, you are going to have some ups and downs as founders so it’s important to foster a good, highly communicative relationship with your co-founder(s) so that you can make it through those rocky days. Again, it may seem fairly straightforward, but it is one of those things that requires consistent attention and can make all the difference.

Recognize what you don’t know and tackle it head on: This was less of a tip and more of an anecdote that Ben shared, but one that I thought was worth mentioning.  Every weekend, he reads a different business book in an effort to hone his business, marketing or technical skills.  Having a ready appetite to learn and grow as a person and a leader is no doubt a part of Pinterest’s secret sauce and something I encourage any entrepreneur to foster throughout their careers.

It was tremendous to have so many alumni back at Lightspeed and thanks again Ben for your time and thoughts.

If you found this post useful, follow me @jvrionis or Lightspeed at @lightspeedvp on Twitter.

People who feel guilty over mistakes make better leaders April 18, 2012

Posted by jeremyliew in leadership, management.
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Just read an interesting article about some research coming out of the Stanford Business School that suggests that feelings of guilt may signal leadership potential. Some excerpts below, but I’d urge you to click through and read the whole thing – it is pretty short.

When we think of a typical leader, most of us picture a person who’s sociable and upbeat. But new research puts a wrinkle in that stereotype, revealing an unexpected sign of leadership potential: the tendency to feel guilty. “Guilt-prone people tend to carry a strong sense of responsibility to others, and that responsibility makes other people see them as leaders,” says Becky Schaumberg, a doctoral candidate in organizational behavior who conducted the research with Francis Flynn, the Paul E. Holden Professor of Organizational Behavior…

Schaumberg first began investigating a possible link between guilt and leadership when she noticed that driven, hard-working people often mentioned guilt as a motivator. “You don’t usually think of guilt and leadership together, but we started thinking that people would want individuals who feel responsible to be their leaders.”…

There are many ways of responding to mistakes or other problems, Schaumberg says, including blaming others and blaming yourself. But the most constructive response, and the one people seem to recognize as a sign of leadership, is to feel guilty enough to want to fix the problem. “When thinking about what traits are important for leaders to possess, there tends to be a focus on what people do well. But we know that people make mistakes and mess up, and it’s important to look at how people respond to those mistakes because that’s a clue to who they are.”

If you read the whole article, you’ll see how it talks about the specific experiments and research that she did to come up with this finding, and also about how guilt (as distinct from shame) is a better predictor of leadership than how extroverted you are.

This reminded me of Carol Dweck’s book, Mindset:

Dweck explains why it’s not just our abilities and talent that bring us success–but whether we approach them with a fixed or growth mindset. She makes clear why praising intelligence and ability doesn’t foster self-esteem and lead to accomplishment, but may actually jeopardize success. With the right mindset, we can motivate our kids and help them to raise their grades, as well as reach our own goals–personal and professional. Dweck reveals what all great parents, teachers, CEOs, and athletes already know: how a simple idea about the brain can create a love of learning and a resilience that is the basis of great accomplishment in every area.

The takeaway is similar. Dweck says that people who have a growth mindset regards abilities and actions as changeable, and think that through more work they can improve. So they embrace learning through failure, and when something goes wrong, they keep working to make it right, to learn.  People with a fixed mindset regard ability as innate, and so avoid situations that could lead to failure.

Schaumberg comes to a similar conclusion from a different direction. She says that people who feel “guilty” feel guilt about an event or action, and work to make it right, whereas people who feel “shame” feel it about themselves, and remove themselves from the opportunity.

Whichever way you come at it, others recognize when someone works to make things better, and they look to those people for leadership.

How to do a layoff January 26, 2009

Posted by jeremyliew in HR, layoffs, management.

It’s never easy to do a layoff. If you have to do it, Professor Bob Sutton from Stanford business schools gives good advice via Wired (oddly not on their website, but in their print edition). I’ve repeated the advice below with my annotations italicized.

Predictability: (If it is clear that cuts will happen) Warn your staff exactly when cuts will happen. Secrecy breeds stress.

Understanding: Humans always want to know why. Give reasonable justification for termination. (Note that with layoffs personal performance is not a factor – layoffs are to do with positions being eliminated. Explain why the company cannot afford to keep the position.)

Empowerment: Let them have some control over their exit. A package with options – say, a choice between extended health coverage or cash up front – reduces anxiety.

Compassion: A little humanity goes a long way. This can include things like having surviving staff out of the office so that affected employees can pack up their desks without people watching them.

What other advice do readers have

How Kosmix employs enterprise 2.0; a guide for other startups July 22, 2008

Posted by jeremyliew in blogs, communication, email, enterprise 2.0, enterprise infrastructure, IM, management, start-up, startup, startups, wiki.
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Anand Rajaraman, co-founder of Lightspeed portfolio company Kosmix, posts about how to stop email overload and break silos using wikis, blogs, and IM.

We hit the email wall at my company Kosmix recently. When we were less than 30 people, managing by email worked reasonably well. The team was small enough that everyone knew what everyone else was doing. Frequent hallway conversations reinforced relationships. However, once we crossed the 30-person mark, we noticed problems creeping in. We started hearing complaints of email overload and too many meetings. And despite the email overload and too many meetings, people still felt that there was a communication problem and a lack of visibility across teams and projects. We were straining the limits of email as the sole communications mechanism.

We knew something had to be done. But what? Sri Subramaniam, our head of engineering, proposed a bold restructuring of our internal communications. He led an effort that resulted in us relying less on email and more on wikis, blogs, and instant messaging. Here’s how we use these technologies everyday in running our business.

* Blogs for Status Reports
* The Wiki for Persistent Information
* Instant Messaging for Spontaneous Discussions

The effects of the communication restructuring have been immediate and very visible. They include a lot less email and almost none on weekends; better communication among people; and 360 degree visibility for every member of the Kosmix team. After we instituted these changes, everyone on the team feels more productive, more knowledgeable about the company, has more spare time to spend on things outside of work.

Anand goes into detail as to how blogs, wikis and IM are used by all employees, and how this has streamlined the communications in the company. I highly recommend reading the whole thing.

Post mortems on two failed startups from their founders July 19, 2008

Posted by jeremyliew in Entrepreneur, failure, management, start-up, startup, startups.

Monitor110 recently shut down after raising $20m over three rounds. One of the co-founders wrote a portmortem of Monitor110, highlighting 7 mistakes that the company made:

1. The lack of a single, “the buck stops here” leader until too late in the game
2. No separation between the technology organization and the product organization
3. Too much PR, too early
4. Too much money
5. Not close enough to the customer
6. Slow to adapt to market reality
7. Disagreement on strategy both within the Company and with the Board

(found via Brad Feld)

At the other end of the spectrum is a post mortem of a bootstrapped two person startup that shut down last month after building for 1.5 years but not raising any venture capital. This founder’s lessons learned are more tactical, but no less important:

1. If your idea starts with “We’re building a platform to…” and you don’t have a billion dollars in capital, find a new idea. Now.
2. It’s a marathon, but it’s a marathon made of sprints
3. Initial conditions matter. A lot.
4. Developing in a vacuum never works.
5. Beware the chicken and the egg.
6. Prototype any 3rd-party libraries that you’ll be depending upon, before you base your product on them.
7. If you’re doing anything other than building your project and getting users, it’s premature.
8. The product will take longer than you expect. Design for the long-term.
9. People have an incentive not to crush your dreams. Take everything they say with a grain of salt.
10. Know your limitations.

(found via Brian Green)

I would recommend entrepreneurs to read both posts.

“Those who cannot remember the past, are condemned to repeat it.” — George Santayana

Entrepreneurs who scale February 8, 2008

Posted by jeremyliew in Entrepreneur, management.

Furqan Nazeeri recently pointed to an old Harvard Business Review article by John Hamm that claims to explain why entrepreneurs don’t scale. Furqan summarizes:

…the traits that help an entrepreneur succeed in the early days actually work against them as the business grows. And worse yet, by the time the entrepreneur figures it out, they’ve either run their company into the ground or gotten themselves ejected by the board. The article gives some examples that will seem familiar to most of us.

The four traits are:

* Loyalty to team mates. A great trait while recruiting the early team, but as Hamm points out, “a potential liability when managing a large, complex organization.” Someone told me a few years ago that first time CEOs are quick to hire and slow to fire while seasoned CEOs are the opposite. There’s some truth to that.

* Task orientation. Getting things done is important in the early days, particularly when you are CEO and janitor at the same time. But as the company grows, it can lose its way without a focus on strategy and vision.

* Single mindedness. Think about how much stick-to-it-iveness is required in the early days but how that can turn into tunnel vision as the company grows.

* Working in isolation. Building a large organization is a team sport, however in the early days there may not be much of a team.

The article goes into much more detail about each trait. With respect to both John and Furqan, I deeply disagree with the premise that the successful traits in entrepreneurs turn into failure modes as their companies scale. Rather, I’d suggest that often good entrepreneurs turn into great CEOs as their companies grow. The traits listed above lead to failure modes at any stage of a company.

1. Founders need to be able to make hard decisions about when people are not working out. This is even more important in a small company than at a big company. There is no room for error in a small company. If someone isn’t pulling their weight, everyone knows about it. If poor performance is tolerated by the CEO and founders, it is demoralizing to the whole company. Founders need to be willing and able to let employees go when necessary.

2. Founders need to be able to focus. Sure, it is important that everyone rolls up their sleeves to get things done at a startup. But a startup is always resource constrained. A startup has to pick the small number of things that it can execute well on, and make sure that those are the things that move the needle for the company. Trying to do to much is a recipe for disaster at a startup, just as it is for a larger company.

3. Founders need to learn the whole business.
Perhaps in a systems company or an infrastructure company where there is real and deep technology to be built, founders can focus on the technology for a couple of years before surfacing again. But in the internet industry, where the technology is just one driver of success, and product, distribution, sales and marketing are also critical, a founder can’t focus on one area and ignore the others. As companies scale up they can afford to bring in experts, but early on the founders need to be able to address all the success factors for the company as there is no one else to pick up the slack.

4. Founders need to build a team. This is perhaps the most obvious failure model of all at any stage of an organization. There is a limit to how much any one person can do.

Many of the most successful companies that the partners at Lightspeed have funded have had founders that went “all the way”, including Jerry Kennelly of Riverbed, Mark Vadon of Blue Nile, Alain Rossmann of Phone.com (now part of Openwave), Jasvir Gill of Virsa (now part of SAP), Tom Riordan of QED (now part of PMC Sierra), Mike Turner of Waveset (now part of Sun) and Zaki Rakib of Terayon (now part of Motorola) to name just a few. Lightspeed believes in finding and funding entrepreneurs like these who have the capability to scale with their companies.