In hind site it’s really too bad that these interviews didn’t come with any equity exchange because our third interview was with now CEO of Groupon, Andrew Mason. Andrew shared his ideas for his startup ThePoint.com, which transformed from an idea to bring people together for collective action, to a company focused on bringing people together for collective purchase, Groupon.com. Both brilliant ideas but the latter turned out to be incredibly profitable.

In the interview Andrew talks a bit about how ThePoint secured their first funding and how and where the team worked. It’s always fascinating to see the origins of startups and I’m super happy for Andrews incredible successes over the last couple of years.

Also, please excuse the amateur nature of the intro. We were Gary V inspired and really excited about ActionsTalk :)

Day 1: Wheaton – St. Louis

Day 2: St. Louis, MO – Denver, CO

Day 3: Denver, CO – Salt Lake City, UT

Day 4: Salt Lake City, UT – Lake Tahoe/Truckee, CA

Day 5: Lake Tahoe/Truckee, CA – San Francisco, CA

We started  our day 2 journey bright and early Saturday morning with Denver as our goal.  As we left St. Louis, it was hot and humid even at 7:30 so we were not too sad to leave but of course I insisted that we stop at a Starbucks for something to eat.  Since Ryan’s best hours are not before 9 a.m., I opted to drive the first leg of the route.  In case anyone is interested to know, the drive from St. Louis to Denver consists of ample farms and maybe even more “adult bookstores.”   I vowed to drive 6 hours and then switch but as we traveled through the repetitive flat lands, I found it hard to even think that I could make it more than two hours.  So of course I went back on my plan and changed the rules so that we would switch every time we needed to fill the tank.

Our first exit off the highway was outside of Topeka and it promised a McDonalds and ‘clean bathrooms’ at the gas station (I try to keep my standards attainable on roadtrips through the middle of nowhere).  As we pulled up to the gas station we didn’t even make it to see the ‘clean bathrooms’ because we got to witness Jerry Springer live while a man dirtier than most homeless people cussed out a woman with butterfly tattoos down her legs.  I was slightly scared but I continued to watch… I couldn’t resist.  After Jerry Springer Live, we opted to wait it out to grab lunch at a different stop.

Believe it or not, we stuck to the rules of switching drivers at every gas stop and kept to the plan so much so that we ended up going all the way to Boulder since we made great time.  We were really tempted to stop and see the worlds largest Prairie dog (which one small town promised to have) but since we didn’t give in to the temptation, we were able to go out to a sushi dinner downtown Boulder.  (Thanks @Micah for giving us the quick tour of the town!)

(our lovely Boulder, CO accommodations, the University Inn)

Tomorrow we will be making our way to Salt Lake City through Wyoming.  Woot! Woot!

We’re going to be blogging our road trip, so follow along to the excitement that is central Kansas, the delectable joy of gas station coffee & donuts, or the relief of arriving safely to Hayes Valley, SF, CA.

Here’s the game plan for the journey…

Day 1: Wheaton – St. Louis

Day 2: St. Louis, MO – Denver, CO

Day 3: Denver, CO – Salt Lake City, UT

Day 4: Salt Lake City, UT – Lake Tahoe/Truckee, CA

Day 5: Lake Tahoe/Truckee, CA – San Francisco, CA

Packing the remaining items from our apartment in Chicago, this beast stopped by to say farewell (see image left). As we were packing, I totally thought I heard a fire truck…turned out it was a tornado siren. When I asked Moll what we should do, she said, “normally we’d head to the basement, but let’s finish packing”. I was confident in my ignorance. We lived downtown Chicago for 4 years and never once have we heard a tornado siren. Isn’t it lovely that today of all days, as we pack the Pathfinder to the brim, an F1 tornado is spoted within miles of us?  We hoped this wouldn’t be an omen to the rest of this journey across the country.

The luck of the Irish returned when we saw a beautiful rainbow overhead just hours later.

As we spent our last couple of days in Wheaton with Molly’s folks, we were sad to leave the fam and our friends in Chicago, but excited for the trek west.

We started the trip to STL for our friend, Whitney’s wedding with plenty of time to spare. Moll planned ahead to make sure she had an outfit for the wedding and some how in the chaos, I only set aside a suit and dress shirt. I was without shoes, a belt or a tie so Nordstrom Rack was a must.

Although we found the Rack & I got some awesome new kicks, it somehow added about an hour to the trip. This would later come back to haunt us.

The wedding was scheduled to kick off at 6pm and at 5:00p it became apparent that we were cutting it VERY close. We realized that we were not going to be able to stop off at the hotel first and a car change was required. We chinese fire-drilled on the highway so that Moll could begin her prep & I took the wheel. She was looking great and ready to roll but as we pulled up the the church at 5:58 I was still in a t-shirt & shorts. I quickly tossed on the suit and new kicks in somebody’s front lawn and we ran into the wedding, disheveled, but ready for the party.

All turned out alright and the wedding was great. Stage 1 of our five day trip across the country was relatively smooth and when we woke up this morning at the hotel the scooter was still safely hitched to the back of my Pathfinder. Day 1 was solid. The next day would be our longest. STL – Denver & 12 very full hours of driving…

To be continued…

The image above contains some of the most interesting data a business could have on an individual. This is heat map of my foursquare checkin’s in San Francisco. It’s powerful data, and it’s only static. Here in lies the info to make assumptions & predictions about my behavior that will changes services I use and businesses I interact with drastically. As a location drivin transportation company it is data like this that will allow us to fundamentally disrupt our market.

This information did not exist even 12 months ago. The services that now collect this data with decent contextual awareness are just recently being enabled by the right devices & the right changes in user behavior. The checkin is a beautiful thing & not just for the foursquare’s and Yelp’s of the world; it’s services like ours that may stand to benefit the most. Here are a few areas that I get most excited about when contemplating how to apply this data to make your life easier and our business stronger…

Marketing

Think about how accurate user location data changes the marketing game. If presumably I checkin to 50% of the venues that I visit on a daily basis, this map does a pretty good job of showing someone where not to advertise if they’re trying to reach me. It’s clear where I spend my time, and it’s clear where I don’t. Now I know not everyone uses these social location services but when this data gets aggregated across a particular demographic or user population you get very targeted results on how to reach that customer group offline.

When applying context (which I discuss next) in these marketing channels you can almost tell what a person will be doing, where they’re doing it, and when. The advertising dollars saved are enough to get excited.

Context

The next factor of awesomeness that this particular map doesn’t yet capture is a sense of contextual awareness. How easily, with foursquare’s new categorical breakdown of venues, could you tell me where are the bars I’m going to, where are the business meetings I’m attending, where are the houses that I’m hangin’ at, etc. What is context:

• time
• activity type
• social

These contextual filters provide yet a deeper layer of understanding to the consumers behavior. Each layer of context that is added to this map the more powerful it will become. The opt-in checkin that foursquare has created is brilliant because it enable someone to feel very comfortable with sharing tons of data. Which in turn allows services to create more value for those users.

What we’re excited about is tying checkins together and realizing that certain combinations of checkin types require different types of transportation and different experiences. By understanding context around checkins we can understand how best to serve our users and be efficiently available for them, when they want us, without them having to tell us ahead of time. For example, you’re at your favorite sushi restaurant with your significant other, we think you’ll likely head to the movie theatre and we’re happy and ready to take you there :)

Logistics Optimization

With an understanding of where our users spend time, and when during the day those transitions occur, we have the ability to offer an incredibly efficient and simple service. As MG at TechCrunch said this week in a post about social location features; the check-out feature or the designation that you’re actually leaving a venue, will likely come very soon. Great! This makes it even easier for us to offer service at the exact times, in the exact locations, that users may want.

With our Uber fleet that is growing quickly, it’s quite possible that we can use information like this that is either publicly available or shared by our users for this specific purpose, to never have to wait for a cab again. With a single click we may know what type of service you would want depending on the context of the venue your checking into & out of.

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The opportunities for this type of contextually filtered data to influence location driven services like ours it unreal. I’m so excited for things like background processing in iOS4, and check-out features from our beloved check-in apps. The real time monitoring of this data is really where it’s at and the better the technology gets and the more transparent the user behaviors become, the smoother overall experience we’ll be able to offer.

So a few weeks ago Zappos sent me a couple books for free :) …

Then on the flight back from SF last week, where/when I do most of my reading, I wrapped up ‘Delivering Happiness‘ by Tony Hsieh of @Zappos. I got the books as a part of their blogger out reach campaign. As far as I know it’s worked really well. I’ve seen a ton of posts around the interwebs today…

In short the book made me really happy, seriously. It was a cool mix of personal stories from Tony’s young entrepreneurial endeavors, all the way up to the sale (or marriage as he calls it) of Zappos to Amazon for $1.2B. His accomplishments are freakin amazing… let’s do some quick math…

He started a company called LinkExchange in 1997-ish and solid it after 2.5 years for $260 million dollars. Then he joined Zappos in 2000 and sold it to Amazon for $1.2B 10 years later. This means that each year he’s with a company, over his career he’s added $100 million / year of value to those companies.

Show me another entrepreneur with that track record!

The book starts out with Tony’s first venture, a worm farm. And in his pursuits for profit he learns he must have a passion for his work in order to succeed. Then with Zappos, a truly brilliant company, he’s realized that a purpose must back that passion in order to create LONG TERM sustainability. The book details the 10-Core-Values of Zappos’ culture and provides indepth letters from employees about how that culture and the Core values have impacted their lives and experiences at Zappos.

Tony is a brilliant entrepreneur and someone I really look forward to meeting someday soon.

Thanks Tony & Zappos for the books! I’ll surely be passing them along.

Quick background on the last 10 years of my life…

At the end of high school in 2001 I wanted to stay in Southern CA and attend USC. I didn’t get in. That turned out to be the best thing that would happen to me. I headed out to the midwest to go to Miami OH & had the time of my life. I partied my ass off, learned the basics of business, and specifically Economics, but more than anything, I learned TONS about myself. I learned what I needed to do to be personally successful and feel fulfilled. Then at the very end of college I met someone “more awesomer” than anyone else, @mollstar.

Because of Moll, I decided to move back out to Chicago after a short stint at home and see if the relationship would work. It did and 5 yrs later we married, and it’s awesome. Now for the purpose of this post, the start of the next chapter.

We’re moving to San Francisco

At the end of June, Molly and I are packing up and heading west. It is a move that I always knew would come, but a huge change none the less. We couldn’t be more excited to blaze a path of our own and quite frankly pull ourselves out of a very comfortable situation in Chicago to a brand new life with new friends, jobs, and experiences. But that’s what I love so much about life, the ability to put yourself in new situations and have new experiences with new people. That’s the gold.

The toughest part for both of us will be moving away from Molly’s family who are beyond amazing. They have not become ‘in-laws’ but truly my family that will be painful to leave. The excitement of being on our own is just one side of the coin. The proximity to such an amazing support system will be tough to go without.

But, both professionally and personally this is a step in the right direction. You all have followed our progress with UberCab and the exciting ride (no pun intended) it has become. We’re breaking ground on a space that is ripe for disruption and yearning for innovation. It’s ready for people like us who may not know the market as well as others, but that naivety may be our strongest asset to our ability to change how things work.

The startup community in SF is particularly exciting. The opportunity to meet, literally every week, with some of the smartest business and technical minds on the planet is not something I’ll take for granted. Through my Uber relationships and the many startup meetups in the Valley, my opportunity to learn from the SF startup community is almost unbelievable. Not to mention the guys I’m going to have an opportunity to work along side. The team we’re building at UberCab is already shaping up to be of extremely high caliber and the quality and experience of our advisors & board may be second to none.

I probably don’t need to even speak to this next topic, but I’m pretty damn stoked to leave the winters. I’ve been through now 9 full winters in the midwest and the ability to hang my snow coat up and away is a welcomed change. Next time I pull that coat out will be for a vacation back to our cabin in WI or a weekend trip to Tahoe…which both sound pretty nice.

Lastly, to our friends. We’re going to miss each of you dearly. As Moll & I moved from Miami to Chicago it was the most natural extension of college. In fact when we first got here it basically was college, except we got paid for it. Then as we (believe it or not) matured, we found out that we are actually making legit contributions to the world. I couldn’t be more proud as I look around at each of my friends and what they’re now accomplishing personally and professionally. Somehow I feel that I chose some of the best people back in college and those guys (and gals) have become the creme of the crop. Got lucky I guess. Please know that even though we’re sort of far away, we’ll always work hard to stay close, stay in touch and keep what we started back at Miami very strong.

This request came from Ad.ly, the in stream advertising company that is run and was started by a friend of mine Sean Rad. Sean was funded last year by a very well respected VC, Mark Suster of GRP. What I really like about what Sean is building is his focus on “streams” and not only Twitter. Obviously, Twitter is the webs strongest stream today, but many services are going to the stream model & this will be a huge opportunity.

This is the email that I received, a request to tweet this appropriately called out (Ad) for a total of $4.23. So, as a starving entrepreneur I decided to get my $4 bucks.

I clicked ‘Approve’ shortly after I got the email and this was the result…

For $4 bucks, I’d say it was totally worth the tweet. I do think it would be a pretty shady practice if that little “(Ad)” was not included in the tweet however.

Maybe the most interesting realization after the tweet was to see my friends/followers respond to the tweet. I had about 2 people tweet me to call me out for selling out my stream, 1 person who thought my account was jeopardized or hacked and then friends just curious about my tweeting ads. Friendly concern.

So, would I tweet more ads in the future? Possibly. I can tell you that I’ve turned a couple other tweet requests down, so I won’t be tweeting just anything (my stream is respected, I love you guys) so I’ll keep it pretty clean. However, I’m not apposed if I’ve used the services that are included in the sponsored tweets.

Twitters Solution

Twitter is executing a similar behavior by promoting tweets within Twitter searches. I’m still skeptical about how much people actually use Twitter to search, but like anything the search behavior on Twitter, will grow. Twitter posted on their blog this answer to the question about promoted tweets.

Q: What are you launching? What are Promoted Tweets?
A: We are launching the first phase of our Promoted Tweets platform with a handful of innovative advertising partners that include Best Buy, Bravo, Red Bull, Sony Pictures, Starbucks, and Virgin America—with more to come. Promoted Tweets are ordinary Tweets that businesses and organizations want to highlight to a wider group of users.

What this means is that when someone searches for “coffee”, Starbucks will have a tweet (like the one above) that regardless of timing of that tweet it will stay at the top of that search. The kicker here is that the Starbucks tweet will NOT be to the side like a Google ad, these tweets will be “in stream”, just like Ad.ly.

I do think, for the record, that there is plenty of space for third party in stream advertising regardless of Twitters entrance to the space.

Our goal for all UberCab users, called clients, is for you to feel like a baller every time you use UberCab. We want you to not only arrive at your destination safely, simply, and efficiently, but we want you to arrive in STYLE.

UberCab clients typically use their iPhone application (also works via SMS) to request a black car limo service within a matter of minutes.

As an UberCab client you’ll get:

• one click iPhone requests
• location based dispatch
• on demand limo service
• in app billing – no cash needed

For Drivers

Drivers working with UberCab are able to turn down time into profit. Simply, we’ll keep you busy and making money.

UberCab operates as a lead generation service for limo companies. By using our iPhone application drivers become available for client requests that are designed to come from clients closest to you.

As an UberCab driver you’ll get:

• immediate ride requests
• never worry about billing
• direct client communication
• a supplement to your existing business

For Partners

There are huge benefits to being an UberCab partner. These are the companies that have multiple cars in their fleet and want to join/partner with UberCab with multiple cars.

When you have multiple cars driving on the UberCab platform you’ll receive actionable analytics about your cars and the trips they’re taking. Better analytics and visibility means better management and more profit!

As an UberCab partner you’ll get:

• real time fleet analytics
• detailed trip logs
• direct customer feedback on ALL trips
• simple billing solutions for fleets

For more information on UberCab or the UberCab team check out our About page, or follow us on Twitter and our blog. Our app will be in the iPhone app store VERY soon too, so keep an eye out!

Typically I leave this Apple fan boy banter to others. To me the “found iPhone” saga is about as interesting as an afternoon of pontificating my navel. Yawn. It was dumb (legally) for GIZMODO to pay money for a lost/stolen device (although they definitely made back the $5k they paid for it). And Apple will always have problems with “the press” revealing their secrets, this isn’t the first or the last time that this will happen.

What’s more interesting to me is the shift from the Apple that we knew and loved…you know the trendy hipster guy that wears vans and t-shirts…to the Apple that attacks the very nerds that CRAVE their products so dearly (see gizmodo editor ejaculating over lost phone.) My thought is that this event was hugely beneficial to both parties. Obviously GIZMODO killed it with 8.6 million + hits on the release post, and Apple’s product will seemingly always kill it whether leaked early (new iphone) or kept relatively quiet until the release day (iPad).

What I’m most curious to see is something we presumably won’t know until looking back on these series of events, whether Apple’s shift from the startup friendly, open-ish platform, F’ the man mentality, towards the Microsoft-esk corporate persona will hurt their overall brand and thus their dominance on the very market they are fighting to control. There has been so much talk about this topic. One interesting perspective is from Jason Calacanis, a tech entrepreneur who is extremely opinionated about such topics. He writes…

Years and years after Microsoft’s antitrust headlines, Apple is now the anti-competitive monster that Jobs rallied us against in the infamous 1984 commercial. Steve Jobs is the oppressive man on the jumbotron and the Olympian carrying the hammer is the open-source movement…

…Steve Jobs is on the cusp of devolving from the visionary radical we all love to a sad, old hypocrite and control freak–a sellout of epic proportions.

Side note: I was 1 yrs old when that commercial first aired. I only know of it because of Youtube.

So with these events that have now proven that Apple is a control freak…

• forcing you to upgrade to a worse version of iTunes
• not letting any other mp3 device sync w/ iTunes
• cutting an exclusive iPhone deal with AT&T (which sucks)
• overly strict app store approval processes (I’m in this right now with UberCab…nightmare)
• closing off competitive apps
  • not allowing Google voice to have a native app
  • until very recently keeping Opera mini a great mobile browser out

…my guess is that in order to keep it’s dominance they will become the big corporate company they fought of in their early days, the corporate, closed, company that nobody wants them to become. The reality is, they may have to become that to keep their lead for a longer period of time. That’s the blessing and curse of huge growth and success in a capitalistic world. In order to keep their success they have to fight for it and that very fighting is what is killing them. It’s like a drowning child in a swimming pool. The very flailing to stay above water is what causes her to drown. Sad, but true.

For now I’ll continue to love and evangelize their products, just like the early Windows users did. I’m sure, eventually that will change.

This is as much of a post about sharing Evernote with you as it is an apology to Evernote for not giving you a chance until now. My mistake and my loss, learn from me and your gain. The simplest way to explain Evernote to those of you who don’t know is that it’s a database for you brain. If you have ADD (like me) it’s a must have tool! Evernote collects information in almost any format that you could ever want to throw at it, and it creates the ability to log, categorize, and store that info. Then, when you need to find something from a random though a few months back, you can search and the search is amazing! One crazy example of the technology is that you can write your name on a white board, take a picture of the whiteboard, then save that picture to Evernote and search for your name. Evernote will pick-up the text from the picture and make that text searchable…incredible!

For so long I had heard about people using Evernote for notes, picture search, and other menial tasks and I dismissed the service. I was actually using the Notes iPhone app and TextEdit saving files in this format, “4/22 notes”. That was dumb. Now that I use Evernote I can tag thoughts, search history and “appear” to the world that I have a great memory.

As a person with brutal ADD, this web service may become my most valuable. I’ve only been using it a week but I’m in love already.

Here’s a little tip on importing old notes into Evernote:

1. Download RTF/TXT Evernote importer

2. Install the application

3. From Evernote, make sure these preferences are selected.

4. File > Import … select all your files and your entire ‘Notes’ history is searchable, backupable, and awesome!

Let me know if you have any questions ryan [at] thedreaminaction [dot] com