How Not to Let the Crazy In

A friend of mine is starting a huge new project.  She told me that 2015 is going to be the craziest year she's ever had.

I suggested to her that it will certainly be the busiest, but that she didn't have to let the crazy in.

We throw around the word "crazy" but in all seriousness, mental health is something that doesn't get much discussion in the startup world.  There seems to be a blog post, book or boot camp for just about everything you could hope to learn as an entrepreneur, but no one really seems to focus on how to mentally survive entrepreneurship.

It bothers me that we just take stress as a given.  Why does fundraising have to be stressful?  You know the possible outcomes.  You're either going to make it or you're not.  You know what happens when you don't.  You could go out of business.  You won't die.  You're not likely to become homeless.

Disappointing for sure, but does it need to twist your head into such knots that you get physically sick over it?

I can't say I stress out about anything.  That's not so say that I don't care about things.  I do care--deeply.  I just don't get into the habit of experiencing anxiety or mentally locking up in the middle of the most uncertain or difficult times. 

That's the key--it's a habit.  I fully believe that habits and training can meaningfully impact your physical experience.  They say that entrepreneurship is a marathon, not a sprint, but it feels like few people marathon train for it.  If they did, they'd be a lot more focused on enduring--being able to last the daily wear and tear--than going as hard as they can all the time.  That includes mentally.  The more mental defenses and best practices you built up, the easier it will be to survive the journey over the long haul.

Here are a few things that have helped me:

1) Take care of your physical self. 

Your brain lives in your body.

It's been proven that exercise, eating well, and getting sleep improves your mental state.  It's simply something you have to make time for--and if you're not, you're doing a disservice to your investors, your employees and your company.  It improves your ability to deal with stress.  When you're feeling good, it takes a lot more to bring you down--so start out each day with a natural physical high as a barrier to stress.

2) Consider the worst case scenarios and have a plan for them.

I was talking to an entrepreneur yesterday who was very confident that two huge enterprise customers would come through in the first quarter--and so the small add-on round they were doing now would be more than enough to see them through.  I asked what happened if they didn't come through--or just got delayed.

Life doesn't always happen they way you plan it--and knowing what your options would be in the worst of all cases ahead of time helps you deal with them better.  Don't push it off because you don't want to think about it, because at the moment that it's happening to you, you're going to feel so stressed out about it that you'll be less able to deal with it.

3) Always try to do your best work, but know and accept your limits.

I try to walk away from every situation knowing that I did my best work.  If that wasn't good enough, I have a clear conscience.  Maybe I just wasn't good enough then.  I'm not perfect.  It's alright. 

Nine times out of ten, it feels like bad situations are the result of something you did half assed that wound up going off the rails.  It's something a little more time and effort upfront could have saved you a lot of headache later.  Compound that with pangs of regret, where you feel like this is something that was your doing or you came up short and the whole thing is going to hang over you bigtime.  Doing stuff right the first time and walking off knowing you gave your full effort (which does not mean bloodshed or giving up your firstborn--reasonable effort) is the best way to go.

4) Try to think as linearly as possible.

Things seem to happen all at once, and if you have eight thoughts in your head, you're simply not going to be able to deal with them all.  We convince ourselves that we are multitaskers, but we're really not.  Try and focus on one thing at a time, do what you can, and then put it away.  Move on completely to the next thing.  If you're doing this thing now but focused on what you have to do tomorrow and then next day, you're going to get stressed out.

5) Don't accept other people's timelines as your own. 

You can only go so fast for so long.  You have natural output limitations.  Other people rarely consider that when they ask for stuff and set deadlines.  In fact, they rarely consider anything.  Most times, I find the expectations that other people have around time are arbitrary.  They don't *really* need that thing right now--and if you gave it to them tomorrow, the world will go on.

Don't be afraid to say, "It's not going to happen by that time.  Here's when I can have it for you." 

There's really no way to argue against that. If you draw lines and say no, they're just going to have to figure out an alternative and accept. 

6) Be extremely protective of your time.

The best schedulers can fit a lot of things in.  Stop in to your event?  Sure.  I can make that!  Meet so and so?  Yeah, if I come into the city early, we can do an early breakfast.  It's tempting to fit all the people, opportunities and events in.

The problem is that it leaves little time for yourself--and for other more appealing activities.  If you don't build in some flexibility, you'll wind up finding out about more appealing ways to spend your time, and then you'll really get stressed about needing to move things, miss things, or reneg on commitments.  Don't try to say yes to everything.  Know your priorities and make time your most stingy investment.

7) Get an assistant. 

There is no reason anyone should have to deal with the insanity of back and forth scheduling, signing up for stuff, filling out forms, ordering supplies, paying things off, etc etc.  Free yourself up from as much administrative overhead as possible because it's not what makes you happy and you'll need that time for other things--like taking care of yourself. 

8) Reverse engineer the life you want to live.

Sometimes, it seems our goals are always "Do the next bigger thing."  It's all about more, faster, next--just this continual, upward climb.  When does it stop?  When can you look around and say, "This is what I actually want."

This happens a ton in the venture capital world where bigger always seems better--but maybe it's not.  If you picture the business and life that would satisfy you, does it require having 300 employees and raising a ton of money to get there?   What else is really important to you?

There's a scene in Wall Street where Charlie Sheen says he wants to make a lot of money so he can motorcycle across China.  The reality is, you hardly need any money to do that.  Realize that many of your dreams and goals are a lot closer at hand than you think--and if you aim for them versus the hamster wheel of bigger, better, faster, stronger, you might actually get to enjoy them sooner.

9) Let other people in.

No one expects you to be perfect.  Have a consistent dialogue about what you're feeling with people you trust who care about you.  They can often provide helpful perspective--and, if nothing else, the exercise of just talking things out yourself can do you a lot of good.

10) Get rid of the people and relationships that drain you.

Some people improve your life, others drag it down.  Addition by subtraction when it comes to your social circle can be a very powerful thing.  There isn't any single person who can be so impactful on your life that you absolutely must have them around, despite the fact that they are emotionally draining and stress inducing.  Move on.  Find some other way to get there without them. 

Congrats to Backupify! A Great Exit Story for the First Company I Ever Backed

Today, Backupify announced that it is getting purchased by Datto.  It's a solid exit to a company that has lots of revs, is growing, and together will form a very formidable player in the data backup space--one that can definitely be a public company in the next couple of years.  

I'm super proud of Rob, Ben and the whole Backupify team--and this is particularly special for me because Backupify was the first investment I ever made as a VC, and the first board I ever sat on.  

In fact, my history with Rob and Backupify goes back almost ten years, well before the idea of cloud backup was ever a glimmer in anyone's eye.

I started reading a great blog called Business Pundit in 2004.  It was written by a guy about my age down in Louisville, Kentucky.  A former engineer, Rob was a great writer and a thoughtful student of management.  I don't remember when I started talking to Rob, but I know it was before February of 2005, because I found "" in the contacts I ported over when I left GM and went to USV.  

We used to chat a fair amount via our respective blogs about management and entrepreneurship.  He was an interesting guy and I watched him throughout a bunch of interesting projects, like a complete open source business where all the employees got to make the decisions.  

I didn't actually get to meet him in person until SXSW in 2007.  That was the year Twitter took off.  

I took this picture of Rob, Michael Galpert, and Danny Wen of Harvest.  Even then, Rob was an optimizer, trying to map the best routes around Austin.  

I liked meeting Rob so much that when I drove across the country that summer, I made it a point to go visit him.  

We stayed in touch and I got to know a bunch of the Louisville startup and creative crew, like Todd Earwood, Matt Winn, and Ashley Cecil.  

Rob messed around with some local video thing in 2008, which everyone but Rob thought was a pretty terrible idea.  Later that year, I sent a tweet that inspired a company that initially only Rob thought was a pretty terrible idea:

Still, he got his guys in the Ukraine to code something up.  On January 6th, just 9 days later, I got an e-mail from Rob:

"Flickr backup is now working.  We will integrate the design and be live for testing end of next week. I will keep you posted."

And keep me posted he did.  "Lifestream Backup" became Backupify and the service started gaining traction--just as the company that I started was losing traction.  Right around the time that Rob finally got convinced that Backupify was a good idea and needed some more resources, I wound up on the doorstep of First Round.  Less than 100 days into joining FRC after winding down my startup, I offered my friend Rob the first term sheet I ever sent out--to lead the seed round of the company I accidentally inspired with a Tweet.

We got the round done with some great names around the table--Jason Calacanis, Chris Sacca, and General Catalyst.  I joined the board and I was assuming everything would always be up and to the right, because that's the way success happens, right?

Well, it turned out the company was probably too early to the market--and while that gave them a lot of time to create the best technology, customer traction wasn't happening nearly as fast as we were spending money on AWS.  

Fundraising for the Series A looked like it was going to be difficult--and that's when Rich Levendov from Avalon Ventures stepped in.  He met Rob at a conference, took a liking to him and saw the same vision on where the space was going.  He took a long term view and jumped in with a check.  He was also there for the company in a big way during what would have otherwise been some bleak follow on rounds.  I thank Rich and his team, as well as David Orfao from GC for their support of my good friend long after I left First Round.  

I'm excited for the company's next steps.  In his note to users, Rob talked of a good future for their combined effort:

"In most acquisitions, technology gets neglected, falls behind, or worse, gets shut down. None of that will happen here. Datto is an R&D company at heart, and the plan is to double the size of the Backupify engineering team, and accelerate our vision of supporting all your cloud apps. We are working toward a joint vision of building the world’s only comprehensive data protection platform, to protect all of your business data, no matter where it lives, and available in seconds when things go awry, to keep your business running."

I'm proud of the whole team at Backupify and have been really impressed with Rob's ability to grow and learn as an entrepreneur over time.  

Plus, I'm glad he sold now, so maybe he can jump in as an investor in my next fund just like Wiley Cerilli did after he sold Singleplatform.  Maybe I should be writing that into my term sheets from now on:  "If this crazy thing works, you have to invest in the next fund after you exit."  

Ten Good Reasons to Take Venture Capital Money

Following up on my post from Monday that rang like "reasons not to take VC money" here are some reasons you should:

1) You really like the investor and believe they can add more value than you give up in equity.

2) You are growing, and if you don't raise, you won't be able to build the infrastructure required not to come apart at the seams.  

3) You have the team in place or identified to build the product, you've done your homework by talking to customers that it is, in fact, the right product, and you're the best person to lead the effort, but you can't fund the build of the product yourself.  

4) You've identified the best team, and while they're asking for reasonable startup salaries, you can't afford to hire them quite yet.

5) You've figured out how to get a sales funnel going, the flywheel is turning, you've got positive ROI on incremental salespeople or customer acquisition dollars and now you want to put gas on the fire.

6) You're on your way to building a network effect, you know how you'll likely make money because you've spoken to lots of potential sources of revenue, but can't monetize without critical mass.

7) You're making a ton of money at the company level, but haven't really ever made any money yourself personally.  Might be time to let someone you want to work with buy your equity.  

8) You're doing something disruptive that is going to have some regulatory or other kinds of hurdles that require human hours of changing the playing field. 

9) You're doing something physical in the real world that just requires a certain amount of capital overhead.

10) You're doing actual science and R&D to build something that doesn't exist yet, but could have a huge outcome.  


Ten Realities of Taking Venture Capital Money

If you take venture capital money...

1) You increase the chances that you may not be CEO of your own company one day--and that also might be the best thing for its long term success.  

2) You are signing up to sell the company one day--to another company or to the public market, but definitely to someone.  

3) You will almost certainly take more venture capital money after that.  

4) You will almost certainly go cashflow negative, increasing the risk that your company will fail.

5) You now have the responsibility to report the progress of the company to others--and to consider their opinions and feedback.

6) You have prioritized growth and your company will be bigger next year than it is now.

7) Some of the people working for and with you now will not be suitable for a growth phase and will have to leave.

8) There are smaller exit opportunities you will not be able to take because your capital structure makes them financially unattractive.

9) You will own less and less of your company over time as you take on additional investment.

10) You will face more competition as venture investment signals that what you're doing may be attractive.

Because the Domain Makes it Really Real

Three years ago today, I grabbed the domain name  

It's kind of a funny answer to "When did you start Brooklyn Bridge Ventures?"

What might be a more relevant date is May 22nd, 2007.  That's the day I sat down for lunch at Coffee Shop with Henry Blodget, just six days after Silicon Alley Insider launched.  Henry told me that I should start a fund--me, a 27 year old former VC analyst turned product manager with no MBA at a startup that wasn't really headed in any particular direction.  It's probably the first time I'd really ever had the thought of starting my own fund.  

So thanks for playing Inception, Henry. 

I guess it's true what they say.  It's easy to be right about market predictions eventually.  It's just really hard to predict timing.  

The stories we tell ourselves about how things get started are often much more linear than they actually happened.  Who had what idea when?  When did you actually commit to something?

Getting a domain name...  I guess that's about as good a demarcation line as any, but that's never really the full story.

So when did I really start Brooklyn Bridge Ventures?

Well, I was born in 1979.

My godfather got me IBM stock right after that, so that's how I knew that a stock market and investing existed.

My dad brought home an IBM PS/2 in 1987.

I got an internship on the buy side at the GM pension fund in high school--in 1997.

I started a business newspaper in 1998 in college covering the stock market and the economy.

I got my first job in venture--at GM--in February 2001.

I tried to write a book for college kids in 2002-2003, couldn't get it published, so I started blogging in February of 2004.

I met Brad and Fred in the Summer of 2004, agreeing to join them later that year--my first job at a fund.

I started a company, failed at it, and joined First Round in 2009 to help them open up their NYC office.  In the middle of that whole thing, I wrote a blog post about Foursquare that a lot of people noticed.

After my two year stint was up, I bought a domain name.

Yeah, so, somewhere in there.

Chances are, your story of starting something is already happening but you don't even realize it.