[Dave Heal's] Observations & Reports

The Best Worst First Date

[Cross-posted to Medium]

You’re definitely going on the first date. I know this is America and you don’t have to do anything you don’t want, but we’re assuming for the purposes of this Einsteinian thought experiment that you are definitely going on the first date.

That being true, what is the worst place you could be invited on a first date that would not foreclose the possibility of a second? Keep in mind that the suggested activity could be anything. So you may get invited for coffee. Or you may get invited for dinner. Or a trip to an art museum. An art museum! That sounds nice, doesn’t it?

But maybe that art museum is full of Che Guevara pop art and your date goes to the gift shop to buy a poster *on the way in.* Would Starbucks be good enough? I’ve heard from veteran daters that it is. What if it’s one of those understocked Starbuckses that is attached to a grocery store? How about Wendy’s? Maybe you, like me, enjoy few things more than a well-timed Frosty, and your date goes to the Wendy’s near campus so often that he (or she!) knows when the fresh batch of fries is coming out and, well, any date that includes “fresh batch of fries” by definition gets a second date.

This is the discussion some friends and I had for approximately 30 minutes while watching the Super Bowl. The loose consensus of our collection of mixed-gender 30-somethings seemed to be “Olive Garden,” and while I think there are places worse than the Olive Garden that would get a second date, I couldn’t convince the group. Yes, my time at the University of Michigan Law School was a total waste.

I also think “Olive Garden” can’t possibly be the answer because of its unusual ironic appeal for most suburban-raised millennials. The unlimited salad and breadsticks feel like cheating, even if the breadsticks are butter-drenched packing peanuts molded to resemble a tiny baguette. There have to be worse chain restaurants that would get you a second date. For me, if all activities are up for discussion, then almost any full meal is going to get a chance at a second date. But I also drove across Michigan to speed-eat a 5 lb. hamburger covered in sour cream and nacho cheese during a minor league baseball game, so…

When the alternative is a short coffee because someone swiped right at midnight after a night of drinking and is just trying to get this over with, a full meal feels like a real commitment, one more likely to get a proposal than a mere second date. But maybe I’m easy to please.

What do you think? What’s the worst place for a first date that would still get you to drag yourself across the second date threshold ?

“Nobody Else Can Make This Shit”: Alex Blumberg & StartUp Podcast Ep. 1

Episode #1 – How Not to Pitch a Billionaire

“So here’s the thing: nobody else can make this shit.”

That’s venture capitalist—”VC,” for those of you in the biz—Chris Sacca, adorable verbal tics and all, assuming the role of Alex Blumberg, aspiring podcast network mogul and venture capital supplicant.

“Our plan is to spend down our meager savings, go into debt and hope it works out. I have a lot of anxiety. Nazanin has a lot of anxiety.”

That’s Alex Blumberg, the ageless voice you remember from Planet Money and This American Life, as he heads down the familiar founder’s road of quitting his job in order to build his own company.

You’re literally hearing all of this because not only is he building a startup podcasting company, but he’s also making a podcast called “StartUp” about building a startup podcast company. Startup.

So here’s the thing: This podcast is one of the best things going if you’re interested in VC-funded startups. Unlike a lot of other post-hoc startup founding advice peddled around the web, Alex is recording this podcast as it happens. Sure, it’s still a professionally edited, mediated work. But his raw material hasn’t attenuated and been filtered through years of additional experiences and agendas. He doesn’t seem to be doing the standard faux-confessional Industry Man thing of trying to appear transparent while carefully tailoring his image to preserve the idea that he is ultimately a competent, fundable entrepreneur. He’s also showing his work, in the form of audio recorded as he goes about the business of building a company for the first time. Actually, this is Blumberg’s first full-time job.

We hear him in a pitch meeting with Chris Sacca. In his apartment with his wife, where he’s laughed at for suggesting a company name that comes from the Esperanto for “ear.” He comes across like the biggest naif ever to ask an investor for money. He overenunciates the words “pitch deck” and “angel investor” like he’s reading aloud from a foreign language text. He gives one of the worst elevator pitches you’ve ever heard. At one point Sacca interrupts him, takes a few notes, and then spits back an unpolished but much much better version of the pitch Blumberg could be giving.

If you’ve been around this world at all, you know that Blumberg is actually no worse than most entrepreneurs out there when they’re getting started. You just never *really* get to experience them at their worst. You only get to read about it 5 years after they’ve sold their company or failed and moved on to another experience and sat down to cobble together dubious memories of how everything really played out. If you like podcasts or entrepreneurship or have a fetish for reedy-voiced guys named Blumberg, do yourself a favor and starting listening.

In the first episode, we learn a few lessons:

1. Do your homework on potential investors. A Little Light Googling goes a long way.

2. How easy it is to lose yourself by trying to impersonate the person you think you should be. Alex is clearly passionate about his business but thinks his investors want to hear him recite a bunch of MBA buzzwords instead of speaking from the heart about what he believes the big business opportunity is and why he’s the one to do it.

3. Investors don’t give a shit that you have the right answers to most of their questions. But they want you to have *an* answer.

4. Everybody you meet during your current job is somebody you might want to call at your next job. Alex met Chris while reporting for Planet Money and got this coveted opportunity at least in part b/c he didn’t screw that up. So don’t get drunk at the conference and fall asleep under your booth.

 

Don Dodge interviews Jennifer Reuting of DocRun

I hadn’t heard of Jennifer, but this interview impressed me. She’s really sharp and has already had success building a number of businesses in an unsexy industry. She talks about how she got into the SMB doc/incorp business as a young girl with MyLLC, challenges as a solo founder, and how her current company is different from LegalZoom.

If reading is more your thing, she also did an interview with Andrew Warner from Mixergy.com, which you can listen to or read the transcript from here.

Micah Baldwin wants you to break the bullshit curse

Forgive me if this post is a bit pedantic, but it’s not clear to me that Micah has identified precisely where the aforementioned bullshit is housed or how much of it there is. Of course, his general advice against bullshitting yourself and others is sound. But that in itself is not terribly instructive. And some of the situations that presumably gave rise to Micah’s post aren’t actually the kind of thing I’m guessing he would identify as bullshit upon further reflection.

The post starts out:

How are you?

In your head, how did you respond? Did you automatically blurt out “fine”?

My freshman English teacher, Mrs. Carter, once told me that answering the question “How are you?” with anything other than “I’m fine” was a waste of breath.

People don’t really care how you are.

It’s the same with honesty. People don’t want honesty.

Not to get all liberal arts here, but humans are complicated. One of the things that separates us from the blue-green algae, other than the extreme delight we take in captioned pictures of misbehaving cats, is our complex language. And Micah’s lead-in here is an example of one of those manifestations of linguistic nuance that cranky people adduce as evidence of rudeness or selfishness but which are actually just people being people. We make some noises with our mouths and they may sound like other noises, but there are all sorts of other cues we use to figure out whether someone is asking how we are or whether they are essentially saying “Hello.”

The latter use is what is known as “phatic.” Wikipedia, as always, has the authoritative example:

Similarly, the question “how are you?” is usually an automatic component of a social encounter. Although there are times when “how are you?” is asked in a sincere, concerned manner and does in fact anticipate a detailed response regarding the respondent’s present state, this needs to be pragmatically inferred from context and intonation.

So, no, the fact that you say how are you and someone says they’re fine is not sufficient evidence of a bullshit artist at work. Likewise if you ask somebody about their startup and they say “we’re killing it.” Now, that is a dumb thing to say because it has become a meaningless cliche in the startup world. You should probably maim that person. But if you are an investor in or advisor to that startup and that is the beginning and end of their response to your inquiry about how they’re doing, then that startup’s problem is not bullshit but simple interpersonal communication. And that might cause you to second-guess your investment in those people.

I guess if you’re a real hardliner about maximizing every breath you take on this planet, then you may have issues with the entire enterprise of phatic communication. But that strikes me as a different point altogether and also a battle not worth fighting. Don’t be that person who spends their life trying to convince people that we should say we drive on a driveway and park on a parkway.

The post continues:

“How’s it going with your company?”

“We’re killing it.”

Shut up.

I’ve taken to answering that question with “It’s interesting.”

Blank stares and fear that I am eliciting a response flow over faces.

“It’s interesting” is a more honest answer, I guess. But if that person’s intention was not to get into a long conversation—or any conversation—about the health of your company, then that may come across as needlessly aggressive or weird, especially if there’s no elaboration. This kind of communication may look like a question, but it is often our way of marking the beginning of an interaction by eliciting a short and mostly meaningless response. A way of establishing that the other person is listening to you and not still trying to commit to memory the lyrics of Big Rock Candy Mountain.

The more important point is that the people asking this question are not necessarily being insincere. Their blank stares are likely not because they don’t care about you or your company. People who want to have an actual, in-depth conversation will usually, if they’re at all proficient in the interpersonal arts, communicate as much to you.

Micah goes on to suggest that these kinds of answers (“We’re killing it!”) reflect self-deception, and that this contagion of bullshit goes on to infect a person’s relationships. Relationships with friends, family, investors and others who deserve more than a phatic “How are you?”

He ends the post with a call to action:

I challenge you to take a day and care. I dare you to listen actively and when you ask someone “How are you,” that you demand a deeply truthful answer.

When your employees, investors and friends ask about your business that you tell them truthfully whats going well, and areas you need help. It’s amazing. People, especially friends, by default, want to be helpful. It’s a gift to provide them the ability to participate in your happiness.

I think Micah’s right that people often preach but actually abhor honesty. Most people are afraid of being exposed as a fraud. That their companies are houses of cards, that they are less smart or fearless or whatever than they’d like other people to believe. And many of us will engage in pathological amounts of self-deception in order to avoid confronting even the notion that we might be less than we portray ourselves to be.

All of this is a problem in the startup world as well. Because it’s inhabited by humans. And Micah’s right to call attention to the need for honesty and sincerity and a willingness to listen to one’s friends and peers. But if his diagnosis of the problem is correct, and I suspect it is, the symptoms are not to be located in these routine moments of small talk but in the unwillingness to follow that up, at some point, with real substance.

 

Smanker: The Social Media Douchebag Gets His Politically Correct Wings

Francisco Dao of 50Kings, writing over at Pando Daily, is trying to make fetchsmanker” happen. That’s short for “social media wanker.” If you live in an area of dense tech startup activity or are a sentient human of employable age, you likely know That Person.

The column makes a valiant attempt to carve out some real estate for his coinage in between “smang it” and “smerd*” in the Gideons Portmanteau Dictionary. But ultimately his Foxworthy-style questionnaire falls short of the comprehensive test that we need for wider adoption. As the unacknowledged hero behind an unsuccessful, decade-long effort to bring back “Opposite Day,” I know well the Sisyphean task he has set for himself.

*Small nerd, e.g., “What up, smerds!”

Francisco, if you’re out there, consider this blog post my offer to help. If catastrophic but edifying failure is also a badge of honor in meme proliferation circles, I am your man. I can also contribute my small but enthusiastic reserve army, the Opposite Day Brigade (ODB). They’ll turn the t-shirts inside out, I promise.

On to his list:

  1. If you put your Klout score on your resume, you might be a smanker.
  2. If you think having a Tumblr page automatically qualifies you for a press pass, you might be a smanker.
  3. If you really believe the economy runs on “thank you’s” and not money, you might be a smanker.
  4. If you’re socially inept in real life, but popular on Twitter, you might be a smanker.
  5. If you think Mubarak was overthrown by Facebook and not by the blood of Egyptian revolutionaries, you might be a smanker.
  6. If your idea of an awesome vacation is going to 140 Conference, you might be a smanker.
  7. If you think “Liking” the Facebook page of a charity makes you an activist, you might be a smanker.
  8. If you’ve ever thought you could survive on Klout perks and social media schwag, you might be a smanker.
  9. If you claim to be an entrepreneur but six months in your “company” is still just a landing page, you might be a smanker.
  10.  If you’ve ever given the advice “be authentic and engage in the conversation,” you might be a smanker.

This is a fine list, as far as it goes. But I have some quibbles. Mainly that a few of the ten are strawmen and are also not quite at the level of hilarity required to warrant inclusion. As David Foster Wallace proved in his non-fiction, if your made-up observations are either LOL-inducing or plausibly true, your audience will forgive you.

Re: #2, I don’t know of anybody who feels that merely having a Tumblr entitles them to a press pass. And I am a much bigger loser than Francisco and so keep the company of people who, if this was a possible thing to feel, would be inclined to. Now, if your Tumblr is on the level of Bon Iverotica or Annals of Online Dating, I see no reason why our Founding Fathers wouldn’t have wanted to give you the freedoms and benefits that come with the designation of “press.” Hell, I’d likely rather hear questions from the person behind Kim Jong Il Looking At Things than most of the White House Press Corps.

#4 is rather harsh on the socially inept. Plenty of delightful, smart folks are better in writing than they are in person. That shouldn’t get them branded as a wanker, or even the final 5 letters of the word wanker.

#5 seems to imply that there are people out there who envision Facebook as a giant 800 million person-Transformer. I get up every morning hoping to meet this kind of big dreamer, but I haven’t. If anybody knows of a Colorado-based meetup for these high-octane imagineers, let me know.

And Francisco, let’s also workshop “smanker” a bit. I have some suggestions for punchier Portamanteaus that might really blow this whole thing open. What do you think of “smoser” (pron.: /’smuzər/ (IPA), SMOO-zer)? Or how about “smassclown”?

Finally, in the interest of being constructive, here are a few off-the-cuff additions I would make to the original list:

1.) If you earnestly use the hashtag “#startuplife,” you might be a smanker.

2.) If your total number of tweets is less than 2x the number of times you’ve retweeted the pithy startup wisdom from Aaron Levie and Shervin Pishevar, you might be a smanker.

3.) If you enthusiastically post and endorse every single infographic that you see, you might be a smanker.

4.) If you don’t currently have a job and don’t actually have any experience doing much of anything besides tweeting in your undies but maintain that you are looking for a job in social media, you might be the textbook definition of a smanker.

5.) If you love George Takei and it’s not because of Star Trek, you might be a smanker.

6.) If, on any social media profile, you self-apply any or all of the following labels (guru, maven, visionary, intellectual, rock star, thinker), you might be a smanker.