@Gregory's Motivatr

Belief

I’ve come across a few stories recently about the importance of belief for entrepreneurs. What struck me most about all of the stories is that belief is both an essential companion and a fickle friend to anyone on an uncharted journey.

You can’t accomplish anything without belief, yet belief won’t always be there for you. Like a fair-weather friend, belief might abandon you precisely when you need it most. So what do you do?

Ben Huh, the founder of Cheezeburger, wrote a powerful post about his bout with depression and worse titled When Death Feels Like A Good Option. He recovered by, as he put it, leaving the room:

It wasn’t for several months that death no longer became an option, but leaving that room and dealing with reality was the best antidote to a make-belief world where life just wasn’t worth it. When I was fantasizing about death as the panacea, the harshness of reality actually helped — it presented me with problems that I could actually solve… 9 years after I left that room, I would call Brad Feld to invest $30 million in my odd-ball company… For those of you who struggle with this, I’d encourage you to keep walking out that door everyday.

Spencer Fry just posted Startups: Stress and Depression advocating having a cofounder as a way to share the burden:

I use to think that after having co-founded two successful startups I wouldn’t need a co-founder for my next one. I was wrong. You can be the most seasoned operator, but at the end of the day you need another shoulder to lean on… Without a co-founder to share the emotional side of running the startup, then, you’re left to bottle things up inside yourself. That’s not healthy and will negatively affect you as a person, which in turn will carry over to negatively affect your startup. You’ll take your stress out on your employees, the product, your loved ones, and your friends, all because you didn’t have a co-founder who could relate 100% with you about what’s going on. Don’t do this alone. 

Marten Mickos, the former CEO of MySQL, gave a Stanford talk emphasizing the need to have others who believe in you, because sometimes you’ll stop believing in yourself. For Mickos that believer was overtime his mother, mentor, investors and even subordinates:

What I’ve learned only in recent years was that I reflected over the fact that thirdly you must always have somebody who believes in you. And you must have somebody who believes in you more than you do, more than you can believe in yourself, because a human being wakes up every morning asking him or her herself, am I useful? Am I needed on this planet? Am I okay, am I doing okay? And we have this nagging doubt, self doubt that follows us throughout life. And when we are in a startup business or in the entrepreneurial world, we will face challenges, challenges that seem insurmountable, really bad situations. And then you have this double whammy that just when it is bad, it also feels bad. And you’re sitting there as the entrepreneur and realizing that you don’t really trust yourself. You are not sure you can make it through the day. You’re not sure you can solve the problem or the challenge you have. So, you have those moments of self doubt just when you cannot afford them. And that’s the moment where you need somebody else who believes in you and who reminds you that you are capable and who reminds you that you are a wonderful entrepreneur

I’d love to hear more people share their stories.

The newspaper with only good news

Newspapers cover the planes that crash, but never the planes that land safely.

Of course the crash is news and the safe landing isn’t, but what a skewed view of the world it leaves us with. Bruce Schneier gave an interesting Ted Talk on how this way of understanding the world leads to a dangerous disconnect between perceived risks and real risks — we worry about a plane crash rather taking precautions to drive more safely on the way to the airport.

I often wondered, what if there were a newspaper with only common, mostly good news. Coverage of all the babies born rather than babies kidnapped, of planes that landed safely rather than ones that crashed, and of people who died peacefully after a full life rather than in horrible accidents. It would be an awfully boring paper and go out of business, but what a statement it would make.

Now we pretty much have that in Facebook, Twitter and the like. For the most part, people only post good news about themselves: vacations, promotions, new relationships, babies, parties, and even safe landings.

Facebook is publishing that impossible newspaper of mostly good news. And they’re making a load of money doing it.

However, this rush of good news isn’t all good news.

As Caterina Fake says, it exploits our basic human anxiety of FOMO (fear of missing out). We share our news of fun parties, successes, and vacations, rather than times of boredom, self-doubt and drudgery. How can one’s real life to live up to the imagined lives of others as informed by their Facebook timeline?

In another Ted Talk, Eli Pariser warns that we’re all in “filter bubbles” that rob us of a common front page experience. Pariser quotes a prescient though depressing observation by Mark Zuckerberg, “A squirrel dying in front of your house may be more relevant to your interests right now than people dying in Africa.”

Five lightweight tools essential for managing contacts

I have always lived my life by making lists: lists of people to call, lists of ideas, lists of companies to set up, lists of people who can make things happen. Each day I work through these lists, and that sequence of calls propels me forward.

- Richard Branson

We all know that our relationships and contacts are one of the most important assets we have, yet how much care do we really give to nurturing and keeping track of them?

I’ve tried a bunch of heavyweight tools such as Gist and Salesforce (which we use as a company), but I’ve found the lightweight tools have made a much bigger difference for me. Here are the four tools I’ve found essential:

Gmail (obviously)

This seems almost too obvious to mention, but I still come across plenty of people who aren’t using Gmail. And some of them aren’t even forced use to use something else by their company.

It’s a tremendous competitive disadvantage to not be able to search and pull up years of past correspondence in a matter of seconds. I remember from my days of using Outlooks/Exchange that it was almost impossible to search and would even take a few seconds to process sending or filing an email. 

Almost more useful than Gmail itself is Gmail’s ecosystem, which all the tools below use. So if you’re at a big company, find a way to use Gmail by hook or crook. 

WriteThat.Name

We all know how it goes: You connect with someone you want to build a relationship with, so you spend 5 minutes copying and pasting parts of their email signature into the right fields in your contacts manager (first name, last name, phone number, title, zip code, etc.). Enter WriteThat.Name, which automatically goes through the email signature of people who email you and adds their info to your Google Contacts. Its user interface is minimal, its graphic design is ugly, but it just works.

WriteThat.Name costs $3 per month after the first month, and if you get someone else to sign up then you get a free month. Speaking of which if you click the link in this blog post I get a free month.

Rapportive

Rapportive gives you a view of the latest social activity of anyone you’re receiving an email from or sending an email to. This information is essential. If it’s someone you don’t know well (i.e. Who is this asshole?), you can get a sense of who they are with one click access to their LinkedIn, Facebook and Twitter profiles. Even if you know the person well, it’s helpful to see their latest tweets right in Gmail to know if they’re on vacation, just back from the dentist or recently got a promotion. 

Boomerang: Send Later

Boomerang solves two very different problems in one package, so I decided to cover them separately. 

An entrepreneur might write emails at 3am and want them to send at 9am to appear professional, and the corporate ladder climber might write an email at 9pm and want it sent at 3am to appear a workaholic. Outlook solved this problem over a decade ago by allowing users to schedule email. It’s a feature so basic you think Google won’t even launch the Gmail beta without it, but they still haven’t added it. Boomerang gives you this simple but powerful functionality. 

Boomerang: Reminders

Often times we send emails that we know we should follow up on if we don’t get a response but never do because we forget. Boomerang will return an email to your inbox if no one responds to it within a given period of time. Simple, but knowing the importance of persistence and following up could change your career and maybe your life.

The first Facebook POTUS

I’ve been wanting to write about this for a while and Sam’s Facebook Timeline feature reminded me to finally do it.

In about a decade or so, we’ll have our first Facebook President of the United States. I’m not talking about a president like Barak Obama who’s increasingly embraced social media. I’m talking about a president who’s been using Facebook since at least college, before she ever thought she’d even enter politics. 

In 1992, presidential candidate Bill Clinton admitted to trying marijuana. I don’t think Clinton did this out of a sense of duty to tell the truth to the American people, but rather to earn the trust of his fellow baby boomers. No baby boomer would believe someone who grew up in the 60’s didn’t do it. (Or they at least couldn’t relate to someone who didn’t.) George W. Bush, Al Gore, John Kerry and Barak Obama followed suit by admitting to smoking weed.

Facebook is my generation’s marijuana.

In college we’ve all been tagged in drunken photos, posted pompous status messages and friended slackers. We probably poked people we shouldn’t have too. Pretty soon, every presidential candidate will have all of these undignified moments in their Facebook Timeline. If they don’t, we won’t trust them.

The great shakeup

Despite all the joking about it, I found yesterday’s earthquake quite humbling. How many New Yorkers woke up yesterday worried about the stock market or their jobs, or totally consumed with some due project, never expecting an earthquake. As innocuous as it was, who knows what could have happened had it been only a magnitude or two larger. We were helpless during the shake.

I write this not to cause fear, but as a reminder of how arrogant it is to assume we know enough about the future to even know what to worry about or be excited about. 

The very fact that humans exists, if you believe in evolution, is a mathematical wonder. Yet we’re still fragile, able to survive only as long as fortune continues to smile upon us. 

Today I’m going to spend a couple extra minutes enjoying the taste of my coffee and the beautiful New York City weather. I hope you do too.

Two phrases every startup should adopt

The term for a mob boss “godfather” was invented by Mario Puzo for his book of that same name. After Francis Ford Coppola turned The Godfather into a hit movie, the mafia actually adopted that term for their bosses. 

Sometimes it pays for life to imitate art (what is good art if not one step ahead of real life?). There are two movie phrases from the last year that every startup should adopt. 

“Wired in”

In The Social Network, whenever someone tries to talk to a programmer working with headphones on, Sean Parker (as played by Justin Timberlake) discourages disturbing the person by yelling “He’s wired in!”.

As any technical or creative professional knows, there’s work to be done that requires complete focus. Even a short interruption can cause a major setback. Yet in the open offices of most startups, it’s very tempting just to go over to a programmer and start asking her questions as they arise. How’s one to know if someone’s in the middle of working on complex code or just reading Hacker News?

Programmers are placed in an awful position. If they’re interrupted from programming they either have to be rude and say “Don’t talk to me now, I’m in the middle of something” or lose a disproportionate amount of productivity. 

For all its inaccuracies, The Social Network highlights an elegant solution used by many programmers — putting on headphones — and coins a perfect term for it — “wired in”. A good programmer is wired in in more ways than one while working.

“Inception”

I thought Inception was a pretty good film but I absolutely love the premise behind it. In the movie a group of criminal specialists have figured out how to literally get into people’s dreams and steal secrets from them, but no one has yet planted a new idea in someone else’s mind. Inception is the ultimate challenge, and the protagonist played by Leonardo DiCaprio spends most of the movie trying to do it.

An entrepreneur must perform inception on dozens, or sometimes millions, of people. We currently call this “pitching,” which implies that your goal is to effectively communicate your idea. But no one wants to work on, fund or buy something because it’s someone else’s idea that they should do so. A pitch meeting really exists to cause the other person to have the idea they should do something. 

Inception is often needed on a wider scale too. Twitter caused millions of people to have the idea that they should post short public status messages. Steve Jobs gave millions of people the idea that they needed a device that put design ahead of features to play music on the go.

We need our vocabulary to evolve and flourish along with our technology. If we all spent more time wired in rather than being interrupted, and more time performing inception rather than pitching, we could be much more effective.

Autopsy of the private meeting

The private meeting was pronounced dead last night, approximately 7:39pm est. The autopsy report showed some signs of struggle. There are several suspects, but none have been apprehended yet.

It all began when Michael Arrington wrote an entertaining post about a meeting he wasn’t invited to of about a dozen unnamed early stage investors. Allegedly these well known angels are colluding to set terms for future deals with startups. 

This accusation unsurprisingly set off a wave of controversy over what the topic of the meeting was, but what I’ve found most interesting is the ability to piece together who’s at a private meeting using social media. A thread started on Quora that now lists everyone who’s thought to have been there along with sources. Business Insider pointed out that one of the angels tweeted he was there and then deleted his tweet “to try to cover his tracks”.

This story really uncovers that it will be almost impossible to have a meeting that only invitees know about in the future. Someone will unintentionally spill the beans using Twitter, fourSquare, Tungle.Me or Plancast. And even if they don’t, they may be tagged by any friend they run into on the way using Facebook Places.

Last December I predicted the end of lying. I’m adding private meetings to my list of things that the next generation will never experience.

Bringing the ruckus to TV

It seems obvious that people should check in to TV shows/books/movies/etc just like they do places on Foursquare, yet so many smart people have tried in well-financed efforts (Hot Potato, Get Glue, Miso, TV.com, TV Guide and Philo) and no one’s seen an exciting level of traction.

While checking in to media makes sense to me intellectually, I’m starting to question if people will actually do it. The competition is just to tweet or FB status update about a television show. And that’s a great experience. I can’t make it though an episode of Curb Your Enthusiasm without commiserating over Larry’s antics with fellow fans by following #curb.

Foursquare had a really creative answer to the location problem — Foursquare brought the ruckus to location. I don’t feel anyone’s brought the same level of original thinking to the second screen experience for TV as Foursquare did for location — most are just attempting to literally be the “Foursquare of TV”.

I wonder if there’s some entirely different way to help people communicate around TV shows and other media that we haven’t thought of yet. It’s time for the internet to bring the ruckus to TV.

Obituary: the bookcase

A well-stocked bookcase has been the most romantic sign of intellect for centuries, yet little is known about its origins. The bookcase likely got its start thousands of years ago, but only came into high demand after the invention of movable type in 1040 and the printing press in 1440.

It’s clear now with devices like the Kindle and the iPad that the bookcase is going the way of the LP. It will be a slow death, with paper enthusiasts holding on for decades. While the LP lived for less than 50 years before it started to be dwarfed by newer technologies, the book and bookcase had an extraordinary life.

The bookcase served three main purposes to us humans: to show status, store knowledge and help people express themselves.

Now that it’s possible to order any book with a few clicks of a mouse for a bargain price, a private library of books doesn’t show much status in life. The knowledge contained in dozens of bookcases can fit on a Kindle, if it’s not already searchable on the internet for free.

Yet there’s no replacement yet for the expression one can make with a bookcase. Showing off what books you read tells the world your interests, politics, philosophy and even religion. It’s acceptable for any houseguest to peruse your bookcase and even yank out a few books, while snooping around your Kindle or iPad at length would be intrusive.

To combat the risk of being too sentimental as we humans often do at sad times like these, it’s worth remembering that the bookcase as a form of self expression has always been paradoxical. Too many people left books they hadn’t read or didn’t like on their bookcase. If a book was really good, you’d have sequestered it to your bedside or insisted that a friend take it to read rather than greedily stockpiling it on your shelf. The best books didn’t last long on a bookcase. But the bookcase’s flaws are besides the point, it’s the best we had and we will miss it. 

While remembering what a good and long life the bookcase had, we can do it no higher honor than to invent its successor. Innovative purveyors of electronic books such as Amazon and Apple have not made it easy to promulgate the library of books we’ve read. If you want to get to know someone, you can view their last 20 tweets in an instant, but you might need to hack into their account to know their longterm reading habits. Moreover, borrowing an ebook out of its device is impossible. 

We won’t find a replacement for the bookcase at Ikea, but I think that the bookcase would have appreciated this irony. We’ll need to use our minds to devise a new way to showcase our intellect.

Photo credit: Writer’s Retreat by Gianni Botsford

Call Me Ted

I just finished reading my first book on my Kindle, Ted Turner’s autobiography Call Me Ted. This is one of the best business autobiographies I’ve read. Ted’s honest in describing his triumphs and mistakes. Most strikingly, he includes stories written by ex-business partners, former employees and even ex-wives that occasionally contradict Ted’s own memories. 

As someone who was just a child during the rise of cable, it’s easy to forget that cable guys like Ted Turner were much like us internet entrepreneurs in their day. 

The constants are taking risks in “crazy” ideas that prove obvious in the long term, being audacious, staying a step ahead of changes in the market, shamelessly promoting your product and being good to your word. There are also some big differences between cable and web entrepreneurship: Ted had to put tremendous effort into financing and gaining distribution for his new ventures.

Incidentally, I’m loving the Kindle experience for two reasons. The Kindle truly puts the book in the cloud; I alternated between the Kindle device at home and Kindle for iPhone on the subway and it synced what page I was on seamlessly. It also makes it very easy to highlight parts of the book and download them as a text file. I’m stealing an idea from my friend Derek Sivers and posting my highlights for my sake and yours (all said by Ted unless prefaced otherwise):

Read More

“Are you crazy? The fall will probably kill you.”

After Butch Cassidy and the Sundance Kid rob a railroad company one too many times, a team of experienced lawmen are commissioned to hunt them down. Butch and Sundance are cornered and outnumbered on a ledge (at least in the movie), with seemingly two bleak options: “fight or give [up]”.

Suddenly, Butch (Paul Newman) has a great idea: jump off the ledge hundreds of feet into the rapids of unknown depth. The following conversation ensues as he tries to convince his partner Sundance (Robert Redford) who seems set on the idea of shooting it out: 

Butch Cassidy: Alright. I’ll jump first. 
Sundance Kid: No. 
Butch Cassidy: Then you jump first. 
Sundance Kid: No, I said. 
Butch Cassidy: What’s the matter with you? 
Sundance Kid: I can’t swim. 
Butch Cassidy: Are you crazy? The fall will probably kill you. 

And they jump.

This should be familiar conversation to any entrepreneur.

At the very start of something new, there are an endless number of questions to consider anticipating the product is a success: Will you have the capacity and scalability to keep your service up with demand? Will your product be able to make a profit and be defensible from competitors? Are you violating any patents? How will you deal with people who want to use your system to spam? Will future innovations disrupt your hypothetical business model? What’s the exit strategy to provide liquidity to investors and shareholders? Can you swim?

But none of that matters if the market doesn’t want what you’re making. You’re unlikely to drown in success because the fall will probably kill you. Think about the swim, but focus on the jump.

Email: the social network of last resort?

I have two old friends who email all their friends in one BCCed mass an update of their lives about once a month on average. One works for a large consumer packaged goods company and the other is a deployed Marine. They don’t know each other well, and I doubt they’re on or even aware of each other’s list.

The emails cover updates on their work and personal lives, including stories about their coworkers and daily battles — literal and figurative. The kind of stuff you’d tell any good friend on the phone, or maybe even a friend of a friend you met at a party. But because of their jobs, they can’t take the step many of us entrepreneurs have taken in being a little more public.

And to be fair, even those of us who blog and tweet need to hold back a lot of personal stuff and work details.

I appreciate the emails. It lets me keep up with their lives even if we go a while without a phone call or one-on-one email. And when we do talk we don’t have to catch up on all the details and can jump straight into meatier topics.

Both friends are on Facebook and one had a blog in the past. But if they distributed the updates on Facebook they’d have to be very careful about locking down the privacy, which is complicated. 

One of these friends told me email works particularly well because when she feels a friend is dropping off the map, she doesn’t have to unfriend them. She just removes them from the email list. And for all dropped friend knows, the emails stopped for everyone.

These regular mass emails to friends make a lot of sense when you think about it. It’s almost surprising that more people don’t do it. Yet I don’t do it myself.

I’m wondering if anyone else knows of people doing this, and if it’s actually a widespread human activity. If you have stories let me know.

My five minute rule for evaluating advice

A friend of mine who is starting her first company asked me for some advice over coffee on how to structure her angel round. She found an investor who said he wants to invest a significant sum, but they haven’t talked about the terms of the deal yet. The question most pressing on her mind was how to structure the deal: convertible debt or equity.

This friend has a great network. She told me she’d already asked for advice from several successful entrepreneurs and was confused because the advice was conflicting. Different advisors made impassioned arguments for each structure to her (which is no surprise since smart people disagree on this issue).

Resisting the urge to weigh in I just started asking more questions about: the company, her expectations in the fundraising process, the prior conversations with the prospective investor and how much money she thought it would take to get the business off the ground. 

It quickly became clear she didn’t really understand exactly how either device works or even how the legal process for closing a deal works. The very experienced people she talked to before me just spouted off advice (i.e. what worked for them) without asking questions or getting a basic understanding of her situation.

Instead of waxing philosophic on what an ideal angel deal is, I just explained what each structure really means and the logistics of closing a deal. It was a huge relief to her because she now understood the choice at hand, and I never told her what to do (aside from get a good startup lawyer!).

It made me think back on the precious good advice and the plentiful bad advice I’ve received since becoming an entrepreneur. 

The good advice usually came only after the advisor took the time, even if only a few minutes, to understand my situation.

The bad advice came quickly, sounded good at the time, but often turned out not to be relevant or appropriate. 

My only unconditional advice to you is not to take advice seriously if the advisor doesn’t spend at least five minutes understanding your situation first.

Some ideas need multiple headlines

I wrote a post on this blog about a week ago contrasting good and bad design, titled Kickstarting your marketing. It wasn’t a very descriptive or compelling headline, but it didn’t matter much for my blog. If you’re subscribed to my blog, you’ll probably (hopefully) give me the benefit of the doubt and read a least a few lines in to see if the post is worthwhile.

The title of every episode of Seinfeld had only one word or term in it. The reason: Seinfeld co-creator Larry David didn’t want the writers wasting time thinking up clever titles for shows.

I feel the same way about writing headlines for blog posts.

However, when syndicating out to new audiences, you need to have headlines that capture attention.

Business Insider picked up “Kickstarting your marketing” but changed the title to “Pitch The Benefits, Not The Features”. Not very exciting, but definitely descriptive and more appealing to their business audience.

I submitted the post to Hacker News with the title “Why Kickstarter’s design kicks ass (take note Diaspora)”, which caused a bit controversy in the comments but did get attention.

Philosopher entrepreneur

So that whole philosopher king thing Plato envisioned in The Republic never quite panned out, but I think us philosophers* might have found a calling in starting and running tech companies.

During breakfast this morning with fellow philosopher entrepreneur Bostjan Spetic of Zemanta, we discussed all the people with philosophy backgrounds running tech companies.

I thought I’d try to crowd source a full list by soliciting your thoughts in the comments or over Twitter.

List of philosopher entrepreneurs in alphabetical order (in progress):

• Fred Benenson, Kickstarter
• Patrick Byrne, Overstock
• Chris Dixon, Hunch
• Greg Galant, Sawhorse Media
• Damon Horowitz, Aardvark
• Andrew Kortina, Venmo
• William Lohse, Pivot Conference
• Ken Reisman, Tlists
• Amol Sarva, Peek
• Bostjan Spetic, Zemanta

I’ve also started a Twitter list of of philosopher entrepreneurs.

*It’s debatable if someone can still be a philosopher while fully engaged in a real profession. Even many of the philosophy professors I had probably wouldn’t qualify as philosophers.