Author: Paul Orlando

If there was ever a situation in which ride sharing apps would be used, it was at LaGuardia Airport, 12:30am after the airport had been closed for a storm. When I arrived, delayed for several hours with many other flights, I found a taxi line that was like nothing I had ever seen. In fact, the line I first saw — already the longest line I’d ever seen — turned out to be only the first quarter of its entire length, the remainder hidden in a slow snake behind a large pillar.

I was tired after the long delayed flight but initially thought that the line was moving along nicely and I’d be home soon enough. On my walk out I’d already noted that there were none of the usual gypsy cab drivers running around offering their services — they had already all been snapped up. I was actually not alert enough at that hour to think of calling a private car myself, though I’m sure the wait would have been hours long if I had. Instead, I started to think about how I could get home faster than waiting out the entire line.

Fortunately for me, a guy two spots ahead started to wonder the same thing aloud. He was clearly not from New York and wondered why no groups were forming to speed the line up. His destination was nowhere near mine and on a normal day I wouldn’t have considered sharing a taxi, but I talked to him anyway and started to teach him about how to refer to NYC neighborhoods, a crucial skill at this time. We decided to help each other out.

This was when I realized that ride sharing services really have a tough slog. If no one was trying to use them on a night like this, or if the line was this long in spite of them, or if there was no one walking around promoting one of them and signing new customers up, there was clearly something wrong with the way they’re run. Or waiting behavior was so ingrained that they had to make a serious push to change it.

While a few people in line vocally complained, the vast majority accepted their fate with complacency, steadily plodding forward a few steps a minute, not even responding to my new, non-New Yorker friend’s inquires as he started to work the line about sharing a ride. Many people were traveling solo, back from business trips, coming home tired and after their delayed flights, unable to think about creatively fixing their wait time problem. Contrast that attitude with the planning for the MTA strike of 2005 where people shared rides in their own cars. They had time to plan. They were wide awake. And no one had iPhone apps back then.

What LaGuadia needed that night was a syndicator — someone to walk up and down the line, find out where peole were going and pair them up. Such roles don’t exist at LaGuardia. And it’s hard for individuals in the lines to do that themselves, especially when travleing solo. Will the guy behind you watch your bags and hold your spot? And anyway, after getting blank stares after asking 10 people (as my new friend did), who will continue to ask more? What drives that behavior? I don’t know if fear is the right word, but there’s a certain lack of willingness to break the unspoken rules about strangers forming groups to travel together.

To initiate the process you someone who doesn’t know any better, my new friend from Denver. To close the process, you also need someone on the receiving end who doesn’t know any better. After 10 minutes he found a woman hours ahead of us in line. And no surprise, she wasn’t from New York either. And you need the guy who enables them to communicate, which happened to be me (instructing my new Denver friend about how to refer to neighborhoods). She agreed to let us share her taxi. How many people followed our lead? Zero.

So an hour after getting in line I was on my way. Here’s how the economics of the trip broke down:
We paid for the woman’s taxi ride (which she hadn’t asked for, but I had no problem doing so). We dropped her off first, even though her stop was farther than either of ours. Next came the guy who was willing to work the line, a well-deserved break for him. He paid $30 at that point, probably about what he would have paid if he had gone solo, but still he saved hours of wait time. When I was dropped off last, even though my stop was closest I was happy. I had saved hours of waiting and paid $20, about what I would’ve paid had I waited and gone myself, but again saving hours in the process.

Everyone won, but unevenly. The process was messy, random, and required someone to break the rules. Thank God for that. What could the ride share services do to make sure no one ever has to go through that kind of wait again?

Is it possible to be too experienced to learn?

I think it is.

A historian told me about an example from US new recruits in WWII and how marksmanship ability varied among them. Supposedly, recruits from the US countryside performed worse than those from the city. This seems counter-intuitive. After all, men who grew up in the countryside were more likely to have experience using rifles to hunt. Those from the city were probably handling guns for the first time.

But here’s what is supposed to have happened. The more rifle-experienced countryside soldiers already had their established ways to shoot and resisted new training in the skill. Meanwhile, those who grew up in the city had little choice but to follow the instructor’s teaching in order to gain proficiency. They were more open to trying new techniques and being criticized for their novice skill level.

That’s sometimes what I see with businesspeople. It seems like more experienced people can sometimes be less open to trying new things or hearing information that counters their established way of working.

One very experienced individual I met last year came to me with an idea for a new financial product which would be sold to institutional investors. He wanted to go out and hire a mathematician and developer to construct an algorithm to describe the model he wanted to build. Never mind first going to talk to people in the financial services niche he wanted to target and figure out how purchasing decisions are made, or finding out if there was a market for the service, or looking at other options that were out there. He was fascinated by the potential of the product, not the people who would buy and use it.

That itself is risky enough. But, he also had no interest in experimenting first before going out to do the development — which would initially easily cost $50K. It’s not that $50K is a large or small amount of money, it’s that I think he could have learned more by spending a fraction of that buying lunch for his target users and getting to know them.

I’m not against spending money, I’m just against being closed to learning.

A lot has been said about MBA programs’ lack of preparation for entrepreneurial work. I’m even going as far as to say that these programs can unintentionally mislead students by rewarding the wrong things. (I’m allowed to make these comments because I have an MBA and ran a startup.)

Here are a few examples from MBA students I interacted with recently and how I thought they were misled.

Misled into requiring a grand vision to be interesting. 
One student I met during a business plan competition had a grand vision for a new fashion company based on cool designs and incorporating the idea of giving a piece of clothing away to someone in a developing country for every piece purchased. Millions of people would bond and communicate through this social exchange.

When I asked the founder what she thought she needed to do first she responded “I need to find a CTO.” Confused, I wondered why a CTO was needed so early for a new fashion company. The response floored me: “because our website will have to be really sophisticated in order to match people around the world in the clothing gifting and communications game.” And no, there was no previous experience working in the fashion industry.

I started to flip out. Calming myself down and asking some more questions about whether she had made any pieces to show potential buyers. No. How about just showing them designs? No… And now you want to hire a CTO? Yes, and also start production. Have you worked in the fashion industry before or can you produce the clothes yourself? No, we’re going to outsource that….

Still bewildered, I suggested this. Go home now and set up an online store. Put a few of your designs up and see if you can get a few people to try to buy them. If yes, then you may be on to something and can decide if you want to continue. If no, then at least you save yourself from spending tens of thousands of dollars too soon. Forget about the social entrepreneurship angle until you figure out if you even have a desirable product.

But the response came back. Well, I can’t do that because setting up an e-commerce store takes a lot of time and also, won’t I destroy my brand if people can’t really buy the things I post?

Serenely, I said this. Spend two hours tonight setting up a Shopify account with your designs and writing the copy. It won’t take you more than that. As for destroying your non-existent brand, use a different name if you want. But do this today so you can have the experience of trying to sell a piece of clothing.

I wonder what happened to her.

Misled into thinking of 5-year projections as fact.
I talked to a team of students working on an education service. They of course had a 5-year plan showing their growth.

“Where do these numbers come from,” I asked?
“These are industry projections for online education.”
“But you haven’t even had one person use your new service. Will these projections hold true for you?”
“According to everything that’s known about this market, yes.”
“But, you don’t know anything about the market yet. You haven’t even spoken to a single user. Why should these industry numbers, which are just forecasts by the way, apply to your service?”
“Well, we kind of need to show this growth in order to make a case for funding.”

Thank you for the honesty. Now the healing can begin.

I heard an entrepreneur talk about getting questions on where the numbers for his 5-year projections came from and then asking the VC about his own experience running a company.

“Where do my numbers come from… When you ran a company did you have your own projections you showed investors?”
“Of course.”
“Well, my numbers come from the same place yours came from.”

Misled into thinking that you don’t need to talk to real people and can buy success.
One MBA was working on a game that let people play finance games.

His plan: outsource all development (already priced out at $60K), sell it to corporate clients, get a ton of students to sign up and use it.

My counter plan: Do no development yet, put together a basic version of this game now that you can run manually, get 20 classmates to try it out and talk to them and look at the results. Then decide if you want to start to talk to potential corporate subscribers.

His resistance: I can’t do any of that without first developing the full game. And there’s no way I can get 20 people to do this.

My thought: There’s money to be made as a developer, designer or “focus group” leader preying on the market of MBAs spending their student loan money.

Then again, I’m critical because I have a high standard for MBAs. The problems above are not that unique to their background — I see that behavior in a lot of places. I just hope for better from the students and their programs.

When we were starting out in my last startup, even before we had heard of customer development, we had a method for learning from users. It wasn’t great but it was better than what a lot of startups were doing.

• This was the first time I truly used Customer Development to build something.
• Generated revenue (a little, anyway) almost immediately
• Got me talking to new people immediately
• Led me to abandon my initial thoughts about running this course

Also, I was asked to speak at an event next week. I’m going to try to condense part of what I talk about at Startups Unplugged and my own experiences. The talk is called “Customer Development: the methodology everyone loves to talk about.”

Looking forward to it.