Phin Barnes, partner at First Round Capital: I have failed a lot in my life. I failed to get into business school the first time around. I failed to build a unicorn startup. I suffered through terrible investor relationships and a disastrous co-founder partnership. But none of these shortcomings has made me a failure. In fact, I think I have been really lucky. I owe tremendous thanks to mentors and friends who pushed me to take the time to study my role in each setback instead of speeding ahead to the next thing. It’s never easy, but through the painful exploration of each failure, I’ve learned how to approach each of the big bangs in my life as a scientist — not as a creationist. Here’s what I mean … Read More »

Michael Skok, investor: When was the last time you heard of innovation without experimentation? Or experimentation without failure? As it turns out, without failure we wouldn’t have post-it notes, pacemakers or penicillin. Failure is not just an inevitable part of innovation – it’s an essential part of the breakage we need to make breakthroughs in the many problems that challenge our increasingly overpopulated, resource constrained, socio-economically challenged world. All these problems are actually huge opportunities for budding entrepreneurs, but we’ll never address them without taking risks and unburdening ourselves from the fear of failure. Instead, we need to learn to use failure intelligently so it doesn’t become absolute. … Read More »

Derek Lidow, entrepreneurship professor at Princeton University: To be a good leader and get your employees aligned with your vision and willing to meet your high expectations, you must be someone they feel will bring them success. The dichotomy arises because entrepreneurs also must be very selfish people who want the world to change and do it their way. That selfishness is what drives them to do the hard things required to change the world. Initially, people who decide to work for a startup find that selfishness appealing and reassuring — they’re confident that the entrepreneur will do whatever is necessary to make the startup successful. But when they find that leader impervious to advice, demanding and arbitrary, the initial glow soon fades. … Read More »

John Mascari, co-founder of Bundle Organics: Looking back, our failure was moving too quickly with the first manufacturer that was willing to take on our business after so many others had said “no.” As the relationship ramped up and we started to see red flags, we tended to say we could work through the frustrations. Ultimately, it was the lack of cultural and value alignment that prompted us to part ways. It was clear that had we looked closer at these issues from the outset, we would have moved on immediately and saved significant time and resources. What we learned is that a good partner should not only help you create a better product but should also reduce unnecessary frustration — leaving more time for you to focus on your core business of connecting with customers and selling. … Read More »

David Drake, chairman of The Soho Loft: I have failed hundreds of times with startups. From coupon cutting to club promoting, from restaurant services to technology companies, from venture-capital funds to hedge funds, you name it and I can tell you where I failed. But I have not stopped trying. In fact, I use the failures I’ve faced in the past 30 years to help me succeed today. Aside from investing in startups, I founded the Soho Loft Media Group, which is engaged in and runs more than 200 financial conferences annually. Running that business is a lot easier thanks to the lessons I’ve learned from past failures. Here’s some advice I’ve picked up along the way. … Read More »

David Ciccarelli, founder and CEO of Voices.com: The temptation for entrepreneurs to risk everything is so prevalent because that’s what is often celebrated. But is risking it all always the right choice? You may have heard it said that an ounce of prevention is worth a pound of cure. Smart entrepreneurs do not simply take risks — they take calculated risks. No one enjoys failing, but failure at times is arguably of the best teachers you could ever have. The next time something doesn’t work out or you’re between a rock and a hard place, remember that you are not alone and that others have faced the same challenges you face now. Any obstacle, shortcoming or setback, if perceived in the right light, becomes part of your story and an experience that you can build on. … Read More »

Sean Bisceglia, founder of Scout Exchange: By the time I was 40, I had started up and sold three companies: a technology-marketing agency, a marketing and creative staffing agency and a resume sourcing technology business. What I can tell you from personal experience is, when you lose all your money and your investors’ cash, you don’t feel much like bragging about it. The biggest lesson that I hope you don’t have to learn the hard way: know when to pull the plug. The idea of quitting was foreign to me, as it is to most entrepreneurs. There’s your own ego and pride, not to mention the guilt that is shellacked to you like glue when you think of letting down your investors, family and employees. … Read More »

RYAN HOLMES: Having said that, there’s a right way to fail and a wrong way. The wrong way is the old lipstick-on-a-pig approach. Something goes wrong — very wrong — but instead of owning up to that and learning from it, the team involved spins the disaster into a win. They give each other a few pats on the back, quickly sweep the project under the rug and never again speak of the months of wasted time, funds and manpower. To me that’s real failure: not acknowledging mistakes when they do happen and not learning from them. Failing the right way, on the other hand, can be good for business. It starts with accountability, not spin, and soul searching, not finger pointing. What went wrong? What can we salvage? Is there an upside? How can we prevent the same thing from happening again? When companies have a culture where it’s OK to acknowledge failure and ask these questions, everyone benefits. … Read More »

MAYNARD WEBB: When things go wrong, I am always looking to see whether or not the founders own the outcome and the mistakes that led to the outcomes, and I appreciate and give credit to people who are self-aware and learn from their errors. At the same time, it’s important to be a bit wary as some people may approach this as lip-service rather than feeling it viscerally. Two years ago, I wrote a piece on how to fail with grace and dignity, which included my seven tips from how to know when to let go to how to treat customers. I believe that founders must learn from their mistakes. As the philosopher George Santayana famously said, “Those who cannot remember the past are condemned to repeat it.” And just as important as owning your errors is being able to look forward. After all, it’s hard to run as fast as possible when you are looking at what’s behind you. Looking ahead is always the only way to advance. … Read More »

Mark Siegel, Managing Director at Menlo Ventures: In an interesting coincidence, we’re nearing the 20^th anniversary of the historic Netscape IPO (Aug. 9, 1995) that launched the dot.com boom. I worked at Netscape from the company’s first year through the IPO, joining Menlo Ventures in 1996. So I’m one of those Silicon Valley veterans who has been in the game through a couple of booms and busts, including the crash driven by the 2008 Great Recession. That experience doesn’t give me a special crystal ball into where the current tech boom is headed, but it has sharpened my pattern recognition skills. I’m seeing many compelling reasons to believe that this time is indeed different, albeit I’ve also recognized a few familiar signs of past mistakes, and thus reasons for caution. … Read More »