I’m a huge fan of Gimlet and love their new Brooklyn-based podcast Startup.
Yet, as a female tech entrepreneur (I’m the founder and CEO of Stride, a tech startup that’s self funded that my team and I have grown to 60 people in 3 years while I’ve battled cancer and raised 2 kids), a mother, and a New Yorker, I take serious issue with Season 5, Episode 4 — Running a Family and a Business.
Read More
I was asked by a CEO recently, “How do I know if my product is ready to scale?” He thought he was ready to raise money and start growing the company, but he didn’t really know how to be sure.
Venture capital exists to invest in enterprises that have a huge opportunity but are also a big risk. Yet VC firms tend to actually be pretty conservative, relying on pattern recognition and social networks to make their decisions. This turns investor pitches into bizarre encounters where you have to help them see the huge risks in your business and how this risks can generate massive returns, but you also must convince them that you have all of that risk managed, so there’s no reason to be afraid. I’ve been turned down so many times by investors “until we’d taken the risk out of the business,” and every time, I’d sit in the car outside their office park thinking, “But don’t you exist specifically to make big bets?”
Read More
Here’s the thing about embracing failure. It sounds great in the abstract, but it’s often painful as an actual experience. Sometimes I’ll pose a question: “Who likes to fail?” And no matter how innovation-hungry or start-up ready the room I’m speaking to might be, I’ve never had anybody say yes. Until recently.
After raising his hand, a talented GE software engineer said that he’d actually developed an appetite for failure in his career — one that’s served him well. In his first few weeks with the company, this engineer dug his heels in and stuck with a favorite software tool he felt was best suited to the job at hand. But when it came down to the wire, his pet solution tanked. So he was forced to spend his weekend frantically creating a hybrid of his own work and what the rest of his department had been building. The resulting innovation ended up saving the day, and his job.
In the short run, failure was worth the gut-wrenching feeling that he was sure to get fired.
And that’s the other thing about embracing failure. It works best when we’ve put everything we can into our work. Failure, then, is like everything else: we get back what we put in.
To quote the software engineer: “If I didn’t fail, I wouldn’t have learned anything. And if I hadn’t had the courage to put everything I had in it, to fail fast, I would have been out of the job. I also learned that you can fail and learn if your leader trusts you.”
The last point, about failure from a leader’s perspective, is important. Failure from an individual perspective is one thing, but what are you supposed to say to your boss when it happens? And if you’re in a leadership role, how do you react when people come to you with bad news, or ask permission to try something that might fail?
For both team leaders and individuals, making failure useful starts with the right questions. Instead of “What went wrong?” you might ask “What did we learn?” Instead of prescribing a particular course of action, try giving teams a goal, with a vision of what good might look like, along with a broad set of parameters to work in. Then ask them how they plan to get their own their own — and hammer home that it’s okay for them to make some mistakes on the way. One leader I know says her role is “being present for the problem.” While finding it uncomfortable at first, she’s found that giving her team freedom to figure it out has resulted in more creativity.
“What’s your hypothesis?” is another one of my favorite go-to questions. That’s the essence of GE’s FastWorks approach. With FastWorks, you create an opportunity to test out a view of reality, and amend it every time you get new information. It’s an experimental mindset — and one that business isn’t always comfortable with. Conventional wisdom says we’re supposed to know all the answers all the time. Nope, that’s a state of mind that’s sure to lead to a dead-end.
When I get asked “What’s your biggest failure?” I often hesitate. Not because I haven’t failed, but because I do it so often. To be honest, when it comes to defining the way that failure is woven in to my work, I don’t even know where to start. I even feel that the question comes with the pressure to have the perfect failure, the one that meshes perfectly with whatever discussion I’m in, or even crystallizes the evolution of my entire career.
But the truth is, there’s no one big failure that results in a transformative lesson that’s a prelude to an unblemished future. For most of us mere mortals, we’re in continual failing mode. Sometimes the failures are big, sometimes they are small. With the right mindset, one that’s as honest and fearless from the start, it’s easier to fail small, early and regularly, rather than waiting for the big dramatic explosion. It’s a daily process, and it doesn’t always feel great, but I’ve come to treasure it as a constant source of meaning and motivation. When I fail, I know I’m on the ropes but still in the game, which is the only place I ever want to be.
The small, daily grind of failing and learning is how we get better. And for some types of knowledge, it’s the only way to get them.
This week, I’ll be asking myself: How have I failed? What did I learn? How can I fail better next time? I’d love to hear your answers to these questions in the comments.
“A pound and a half of Land O’Lakes white American, sliced as thinly as you can.”
“But ma’am,” the deli clerk sighed, “they’ll all stick together.”
Read More
We sold L2, the firm I founded in 2010, today to Gartner (NYSE: IT). The transaction is, undeniably, a good / great thing for the employees and shareholders of L2 and should / will be a win for Gartner. Some thoughts four hours post-closing.
Deals are hard to get done. Really. Fucking. Hard. We had substantial interest from several suitors, yet closing the deal felt similar to landing an F-15, low on fuel, on an aircraft carrier, at night, in stormy seas. My job was to get the plane on the flat top (close the deal) while others kept the carrier (business) moving, and the plane kept getting waved off. Deal people (high-priced bankers, lawyers, private equity) are rich for a reason, as it takes skills, perseverance, and an iron stomach. I haven’t felt this stressed since the financial crisis. This was a better flavor of stress — fear of something great not happening — whereas the stress I felt in 2008 was just fear. But still, stress.
The elusive recipe need not be hidden in a vault or passed down from Nana to her next of kin. Here’s a tried-and-true recipe that was handed down generation to generation in Silicon Valley for 60-plus years. Yes, it’s a family secret, but I’ll share it with you now.
INGREDIENTS:
Back in December of 2011, I wrote a piece I called “The Internet Big Five,” in which I noted what seemed a significant trend: Apple, Microsoft, Google, Amazon, and Facebook were becoming the most important companies not only in the technology world, but in the world at large. At that point, Facebook had not yet gone public, but I thought it would be interesting to compare each of them by various metrics, including market cap (Facebook’s was private at the time, but widely reported). Here’s the original chart:
I called it “Draft 1” because I had a sense there was a franchise of sorts brewing. I had no idea. I started to chart out the various strengths and relative weaknesses of the Big Five, but work on NewCo shifted my focus for a spell.
Read More
At the first annual Shift Forum, we established a framework for a new kind of business conversation: The interwoven, tectonic shifts driven by both political and technological uncertainty have left capitalism at a crossroads, and we agreed to elevate our thinking beyond a single industry or subject area, focusing instead on the issues and challenges driving our society overall. The result was a fascinating dialog between innovative startups, established global corporations, non-profit leaders, and senior regulators and policy experts.
But where do we take the conversation from here?
Read More
Early in my tenure at Puppet, I had one of my employees, José, make laptop stickers. He said we already had some, and I said, yeah, but they suck. So he designed something different. I said nope, still not right. Finally, in frustration, he said, “You clearly know what you want, can you just tell me what it is?”
I expect many of you will recognize this problem. It is sometimes called “Bring Me a Rock”, which pretty well captures its absurdity. Becoming a better leader required I find a way past it.
Read More
Every founder understands the importance of culture in the long-term success of their company. Yet rather than valuing and supporting all employees, organizations like Uber still manage to build a toxic, poisonous one. How does this happen, and what can you as a founder do to prevent it?
We’re still in the early days of understanding how to build great culture. However, the barriers to doing so are surprisingly similar to another area where we’ve come leaps and bounds in the last decade: Creating great products. The similarities in their problems mean the tactics for solving them should be portable, too. In both cases, the barrier is essentially:
Read More