Recently, I wrote a post titled After Your First Big Success, What’s Next? The comment thread was powerful and fascinating, as was the direct email feedback I got, including the following note:
“I think it would be interesting to hear your perspective on how an entrepreneur should approach “what’s next” after coming off a failed business. How should one manage their own emotions and their own perspectives post failure? It’s easy to play the blame game and it’s easy to be extremely hard on ourselves. There has to be constructive ways to move forward rather than destructive ways that could lead to lack of confidence, or depression.”
Having failed at a lot of things, I’m completely comfortable tackling this. But let me establish my bonafides first. My first company, Martingale Software, failed (we returned $7,000 of the $10,000 we raised.) My second company, DataVision Technologies failed. I didn’t have success until my third company, Feld Technologies. While my first angel investment was a success, I resigned as the chairman after the VCs came in and left the board after the CEO was replaced. In the late 1990s, what looked like my biggest success at the time, went public, peaked at an almost $3 billion market cap, and then went bankrupt three years after the IPO. And the second VC fund I was part of, which raised $660 million in 1999, was a complete disaster.
As the cliche goes, I learned a lot from these failures.
I’ve had many more. I remember firing my first employee, which I viewed as a failure on my part, not hers. I remember the first CEO I fired and staying up all night prior to doing it because I was so nervous and miserable about the decision I’d made to back him. I remember the first company I funded as a VC that failed and struggling to figure out how to shut it down after everyone else fled from the scene. I remember the first time someone threatened to sue me for doing a bad job for them (they didn’t.) I remember the first time I was sued for something I didn’t do (I eventually won.) I can keep going, but you get the idea.
What’s next is simple. It’s whatever you do next. In some cases this will be easy – you’ll already be on to the next thing before the previous thing you were working on failed. In many cases it won’t be easy – you’ll be wallowing in the quicksand of the failure well after the other bodies have been sucked below the surface.
How you deal with your own emotions, and perspectives, is an entirely different matter.
I love the approach of Jeremy Bloom, the CEO of Integrate (we are investors) who I have immense respect and adoration for. In 2006 at the Winter Olympics, he was the best freestyle mogul skier in the world. On his last run, he was expected to take gold. Halfway down he missed a turn and placed sixth. As Jeremy told me, he gave himself 24 hours to be angry, depressed, upset, furious, frustrated, confused, and despondent. I imagine him in his room in the Olympic Village systematically destroying all the furniture. One minute after 24 hours, he was on to the next thing, with the failure solidly in his rear view mirror.
Now, 24 hours is a short amount of time. I’ve often carried my failures around for longer, but never much longer than a couple of days. I separate how I feel from failure from how I feel about life and what I’m doing. Interestingly, for me, failure isn’t the thing that gets me depressed, it’s boredom combined with exhaustion. But that took me a long time to figure out.
I’ve found that talking to people about my failures is helpful. Rather than hold them inside, I talk to Amy (my beloved) about them. I talk to my partners about them. I talk to my close friends about them. I don’t ignore the failure or try to bottle it up somewhere. Rather, I set it free, as quickly as I can.
In our book Do More Faster, we have a chapter on the the wonderful story of the failure of EventVue. After it failed, some of Rob and Josh’s friends from the Boulder Startup Community had a wake for EventVue. We celebrated its life, buried it, and moved on. I loved this idea and have done it a few other times for failed companies. It’s important to remember that even in death you can celebrate the wonderful things that happened during life.
But ultimately, you have to know yourself. There is no right answer or magic salve for getting past failure. If you are going to be an entrepreneur, you are going to experience it a lot. It’s just part of the gig. Start by understanding that, and asking yourself what you are really afraid of. And, after you fail at something, let yourself experience whatever you want to experience, remembering that it’s just another small part of the journey through life. And then go on to whatever is next, in whatever time you are ready for it.
As exits have been flowing nicely again the past few years, many of the entrepreneurs I work with have experienced their first big exit. I refer to this moment as when you find that you have life changing money in your bank account, which I like to call “fuck you money.” You now can do whatever you want with the rest of your life.
I was on a walk with an entrepreneur recently who was wrestling with this when we ran into another entrepreneur I had backed who had an exit a while ago and had wrestled with the question of “what’s next.” We chatted briefly and then he hopped on his bike and continued his ride.
Later in the day, I got the following magnificent note in my inbox from my bike-riding successful friend.
I was thinking about the ‘what’s next’ conversation. I’m sure you’ve seen everything and are all over it, but in my more limited experience, for some people it’s harder than the what’s first conversation (i.e. should I start a company or not?).
I find, unfortunately, that a reasonable percentage of people chase their tail endlessly looking for the next big win, but they can never catch it because they have no idea what they are chasing. Their life spirals inward as they get more unsure of themselves, more frustrated, more unhappy.
I think this state of uncertainty and self doubt causes more depression, divorce and addiction for some people than starting and running a company. Especially if they’ve never felt failure before. Now they fail all the time and they can’t figure it out.
I think it’s mostly because they never find passion again, or they look for it in the wrong places. There are a million things they can do in the world, but the spend most of their time looking for the next great technology company that sells a better widget, but doesn’t necessarily change their life in any meaningful way.
They have grand opportunity because they are unbound to do something they truly love. If you love mentoring, mentor, if you love the environment, help it. If you love children, teach them. If you love your family, share with them. Give back to everyone who gave to you on the path to success, and then give more broadly to everyone who seems deserving.
To me, that’s the real grand victory.
Totally brilliant. And so simple.
I had my first exit when I sold my first company (Feld Technologies) at age 28. After the dust settled and I had sold all the stock I’d received, I’d made somewhere between $1m and $2m after tax. When Amy and I talked about “what’s next” when I was 29.5 (about the time I finished working for the company that bought mine) one of the options for consideration was to retire and move to Homer, Alaska. I was making plenty of money consulting and, while I was investing much of the money I made from the sale into new companies as an angel investor, the idea of living in Homer was attractive. We figured we could easily live for the rest of our life on consulting income and what we’d managed to save, even if none of the angel investments I was making turned into anything. When one of them was acquired a few months later and we had another $1m after tax, we realized that we could easily live on $40k / year of cash in Homer, which would last us about 25 years if we made no other income.
We were deeply in the “should we just call it quits and go live a different life conversation.” But at almost 30, I just didn’t feel done, and in many ways I felt that I was just at the beginning of a new journey (which turned out to be true.) So we packed up, moved from Boston to Boulder, and decided to build a life in Colorado, while I continued to invest. This was 1995 and the path from there has been powerful and dramatic. By 1999 I had to ponder “what’s next” again after a number of my angel investments returned more money to me than I ever thought I’d have, and then again in 2002 after getting massively crushed by the collapse of the Internet bubble and losing even more money on paper than I expected I’d make cumulatively in my lifetime.
I’ve been through the “what’s next” discussion with Amy several times, including in 2004 when I doubled down on Mobius Venture Capital (instead of packing it up and calling it quits), in 2006 when we decided to start Techstars and Foundry Group, and again in 2013 after spending six months being extremely depressed.
Each time, I’m adjusted how I spend my life in the way my friend talks about in his final paragraph:
They have grand opportunity because they are unbound to do something they truly love. If you love mentoring, mentor, if you love the environment, help it. If you love children, teach them. If you love your family, share with them. Give back to everyone who gave to you on the path to success, and then give more broadly to everyone who seems deserving.
If you’ve recently had some success, as you go into the weekend, take some time out to ponder how you are you thinking about this. And share if you have any insights!
If you are an founder or employee of a public company, repeat after me:
This is one of my favorite Jeff Bezos quotes.
It’s easily to get bummed out when your stock price drops. I believe the emotions follow the +1/-5 rule. Each time it goes up, you get one unit of happiness. Each time it goes down, you get -5 units of happiness.
Think about that for a second. If you look at the stock price every day the market is open, you’ll look at it about 250 times a year. Let’s assume that your stock is higher at the end of the year, but that on 125 days it goes up, and 125 days it goes down. You’ll have +125 happiness for the up days and -625 happiness for the down days. Even though your stock price is higher at the end of the year, you’ll have -500 happiness points.
Now, in the above case, if you only look at your stock at the end of each month, you’ll have 6 up days and 6 down days. That’s +6 – 30 = -24 happiness points. Still unhappy, but less so.
If you look at the stock only one time at the end of the year, you’ll have +1 happiness points.
Lesson: Don’t look at your stock price. Run your business. Work in your business. Do amazing things. Build value. Derive your happiness from the amazing things you are doing for your customers, the great people you work with, and the mission that you are on. Oh – and all the great things in the rest of your life outside of work.
Remember: You are not your stock price.
There will be a lot of books written about the story of Twitter. As far as I know, there have now been two, but there are probably 71 more coming out soon.
Biz Stone’s new book, Things a Little Bird Told Me: Confessions of the Creative Mind is outstanding.
I’ve read two really awesome books in the past month that combine first person startup accounts with personal philosophy and advice. Biz’s is the second. Ben Horowitz’s book The Hard Thing About Hard Things is the other.
Ok – enough effusiveness. There is a simple reason these two books are outstanding. They both mix the author’s direct and very relevant experience with their personal philosophy and lessons learned from the experience. While moments of Ben’s book are dramatic, Biz tells the story of Twitter in an understated way. He’s fun and playful while covering enough of what happened so you have a feel for it. But it’s not overwrought with drama.
Instead, Biz focuses on highlighting critical moments, and key experiences that he had, which help the reader understand the path of a remarkable company. I’ve heard most of the stories before, although a few were new to me. Biz drills into the essence of what matters and not the noise surrounding it. As a result, I felt like I could really process the experience and understand the lessons he learned, rather than be distracted by stuff around the edges.
While I don’t know Biz, I immediately related to him. He drew me in. He’s a guy I’d like to hang out with. Someone I’d like to know, who I’d be happy to go into battle with, or just have a long playful dinner. Basically, he’s real.
If you are an entrepreneur, or a student of entrepreneurship, Things a Little Bird Told Me: Confessions of the Creative Mind is another must-read on my list.
If you haven’t yet bought Ben Horowitz’s book The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers, go get it right now. It’s one of the best books you’ll ever read on entrepreneurship and being a CEO.
If you are a CEO, read this book.
If you aspire to be a CEO read this book.
If you are on a management team and want to understand what a CEO goes through, read this book.
If you are interested in entrepreneurship and want to understand it better, read this book.
On Friday, I spent the entire day with about 50 of the CEOs of companies we are investors in. Rand Fishkin of Moz put together a full day Foundry Group CEO Summit. It used a format Rand has used before. We broke up into five different groups and has sessions on about ten total topics throughout the day. The groups were fluid – people were organized by category (alpha and beta) but then went to the topic they were interested in. There was a moderator for each session – the first five minutes was each CEO putting up one “top of mind” issue in the topic, and the then balance of the session (75 minutes) was the entire group spending between 5 and 15 minutes on each topic.
It was awesome. We finished with a fun dinner at Pizzeria Locale. I drove home with my mind buzzing and arrived around 8pm to see Amy laying on the couch reading a book. So I grabbed my iPad and looked to see what was new on it.
I’d pre-ordered Ben’s book so it was in slot number one. It felt fitting to start reading it.
At 10:30 I was finished with it. The Hard Thing About Hard Things was the perfect way to cap off a day with the CEOs of the companies we invest in.
Trust me on this one. Go buy The Hard Thing About Hard Things right now.
Ben – thanks for writing this and putting 100% of your heart into it.
I had a wonderful time interviewing Larry Gold last night at Entrepreneurs Unplugged. Larry is a special guy and someone I learn from every time I’m with him. Among the many great stories he told, including a doozy about the time he was a sophomore at Yale, he had a powerful one about how entrepreneurs assess potential outcomes. It resulted in a fun version of entrepreneurial math.
Envision a scenario where you there are 10 separate things you need to do to have a successful outcome. Each one has a 90% probability of success. What’s the probability that you will achieve a successful outcome?
I struggled with 6.041: Probabilistic Systems Analysis and Applied Probability (the probability course I took as an undergraduate) – it was one of those courses where I felt like I was a week behind for the entire semester. I did better in 15.075: Statistical Thinking and Data Analysis – maybe I was a little older, it was a little easier than 6.041, or I was more interested because I liked the professor better. If you are having trouble with a quick answer, both courses are available to you on MIT OpenCourseWare.
Back to the question. If you guessed around 35% you are correct. It’s actually 34.87%, which is (.9)^10. Now, by using the word separate, I’m implying 10 independent events, but this is the nuanced joy of theory versus practice.
Larry pointed out with glee that regardless, entrepreneurs believe when they start down the path of doing these 10 things there will be a successful outcome. Hence entrepreneurs math is (.9)^10 = 1.
Whether you agree with the math or not, it’s a great anecdote. So many things that we try as entrepreneurs and investors fail. We never make an investment thinking “this isn’t going to work”; we always invest thinking “this will work.” I don’t know any entrepreneurs who started their business thinking “this will fail” or even “this only has a 35% chance of working out.”
This shit is hard. And it’s low probability. Even if you have an ultimately successful outcome, many of the things you are going to try along the way are going to fail. But to do them, you’ve got to believe they are going to work. You’ve got to enter into the illusion that (.9)^10 = 1.
Techstars is rolling out a short video program with some of the entrepreneurs and mentors favorite quotes. I recorded a few of them recently – my first one is up.
I’m a huge Battlestar Galactica fan and think Commander William Adama has amazing leadership lessons for any entrepreneur. If you don’t know what “rolling the hard six” is, it’s a classic example of a high risk / high reward scenario. Per Urban Dictionary:
“Rolling a hard six has a probability of about 3% whereas rolling six by any other combination has about a 14% chance. A hard six pays 7 to 1 whereas a regular six pays only 7 to 6”
I’m not a craps player, but I love the metaphor. As an entrepreneur, you often have to combine luck with the right call at the right time. You can make the right call and be unlucky, or you can make the wrong call and be lucky. But when you find yourself in a jam, you often need to make the right call AND be lucky.
My imitation of Adama is pretty lame however.
Phin Barnes at First Round Capital just nails it today with his post To get the most out of your investors, turn them into rubber ducks.
Go read it – I’ll wait and will be here when you get back.
I love Rubber Duck Debugging. I use this approach when writing, which I call “Writing with Yoda.” I have a little Yoda figurine staring at me at all times and when I stall out I just talk to him for a little while and then get started again. He always looks serene and wise and I almost always get going after talking to him for a little while.
Phin describes five steps to turn your investors into rubber ducks:
These are similar to how to engage a great mentor, which we teach over and over again in Techstars – both to the entrepreneurs and the mentors. If you’ve ever done a Top of Mind Drill with me, you’ll recognize the Rubber Duck approach with one twist – storytelling.
I’m a storyteller. I learned this from my dad. It’s part of why I love to write – it’s a way for me to think out loud and figure stuff out while telling stories. So – my favorite Rubber Ducks are the ones who can also tell stories, at the right time.
The risk of a Rubber Duck only approach as a VC is that you become overly socratic. We all know the VC who just asks question after question after question. The questions are often good, and they drive you deeper into the problem, but at some point you need to take a break. You need a breath from answering more questions. You need an analogy to relate to.
This is when the Rubber Duck should tell a story.
At a board meeting recently, the CEO looked at me and said “just tell me the fucking answer.” So I did. And that works also. But not until the CEO wants that. Until then, be a Rubber Duck.
Remember – the CEO makes the decision, not the VC. Unless the CEO explicitly asks. And – if as a VC you don’t trust the CEO to make the decision, you have that discussion with the CEO right now. And if you are a CEO who’s VCs aren’t letting you make the decisions, buy them some Rubber Ducks.
“Passion is temporary. It doesn’t last long. Love is enduring. And that’s the important thing. If we all had love in our lives to the degree that we should, it would be much happier.”
— UCLA Anderson | John Wooden Global Leadership Award ceremony (May 21, 2009)
Last night I had dinner with my partners and our significant others. It was a wonderful evening with the three people I work most closely with, the people they love, and the most important person on the planet to me.
Earlier this year I had dinner with Jamey Sperans, one of our investors. Late into the night we talked about a variety of things at an outdoor restaurant in Philly under the heat lamps as a chilly spring night unfolded. Much of the conversation was personal, as in addition to being one of our largest investors, Jamey has become an incredibly close friend. I was struggling with my depression so we talked some about that, but that merely served as a launch point for a deeper conversation.
In that discussion, we talked about the concept of “Business Love.” For a long time, I’ve talked about “business intimacy” – it’s the relationship I try to develop with the entrepreneurs I fund and the people who I work with. It’s a level of emotional engagement that is much deeper than “friendship” or “respect”, is not easily developed, and can be quickly lost if one party isn’t interested in investing the energy or violates a fundamental principle such as trust or honesty.
Jamey and I agreed that “business love” was more profound and significant than “business intimacy.” We discussed the concept of business love in the context of Foundry Group with the unambiguous agreement that the four of us (Ryan, Seth, Jason, and I) have a “business love” relationship.
Once a month we have a full-day offsite. We try to keep our process to an absolute minimum, so we have lunch together on Monday’s and a once a month offsite. The rest of our interactions are continuous and real-time, including almost all of our investment decisions.
Yesterday’s offsite was a perfect example of business love. We spent the day sitting around Jason’s dining room table (the general location of our offsite), got calibrated on a few things that are new initiatives of ours including FG Angels, a new treat coming out next week from us, and a new project we are launching in January. We talked about a few deeper, long range things we want to get right, especially in the context of several of our very successful investments. And we argued about some stuff that we disagreed on in an effort to both understand the data and get aligned.
It was awesome and one of my favorite days of the month. When we split up around 3pm (we end when we are finished) I had a permagrin on my face. I walked home and spent a few hours grinding through email. I went to a meeting and then picked up Amy to head back to Jason’s for dinner. We had an amazing dinner as a group to end the day.
I woke up this morning thinking about business love. I remembered my conversation with Jamey. I recalled that Jo Tango had written a post on business love a while ago and went back and looked it up. I’m guessing that Jamey was the LP in the post that Jo is referring to, since the principles of business love, that Jo refers to, are exactly what we talked about.
The process of creating and building new companies from nothing is hard. It’s incredibly rewarding when it’s successful, but the process can be an excruciating, chaotic, and messy. There are moments of extreme stress. Failure is always lurking in the background. Working alongside people you truly love makes a huge difference, at least for me.