Our team had an invigorating meeting on Friday with Howard Diamond, and I use invigorating in the purest sense of the term. Howard is a bundle of energy and a fountain of ideas & information - and he immediately engaged our team. In fact, I quickly surveyed the room mid-meeting and found us all in similar postures: leaning over the table in rapt attention.
Howard is also a money guy. He excels at making sucky companies succeed. In fact, Howard usually gets handed the most unprofitable, crappy, failing companies and somehow he turns them around. He’s been the CEO of at least three companies, the first of which, under his leadership, doubled in 6 years, to become a $1.2 billion, profitable company. It was acquired by Level 3 Communications. He is now Chairman of the Board for Rendezvous Entertainment and an active mentor in the Techstars program.
Howard grasped the nuts & bolts of our company going into the meeting, as he had already met with Nathan and heard the elevator pitch. After asking a few questions regarding the functionality of our main tools and how we plan to help travelers, Howard declared, “Travel’s a pain in the ass!” The simplicity and force of that comment stuck with us as he opened up the floor for a full-on discussion.
Howard is a huge proponent for us doing something that will a) help make travel easier, and b) help a segment of the population feel like they’re being taken care of. He pointed out that nobody is taken care of anymore with regard to award travel. Everybody (regardless of your status) has to follow the same monotonous and time consuming routine of keeping track of their awards (somehow) and contacting each airline, hotel, or other party to figure out how and when to redeem them. It IS a pain in the ass!
Howard suggested we focus on answering three simple questions for each frequent flyer as soon as they land on our site:
1. What are the problems you are going to solve for me?
2. What do I have to do to make it work?
3. How will you make this process easy for me?
It didn’t take much consideration for us to conclude that these were, indeed, the exact questions we need to answer for our users when they land on our site. What’s more, I think these questions can be used by almost every company in Techstars as a guiding principle on their site. It comes down to addressing what problem you are going to solve for your users, how you will do it, and how easy it’s going to be for them. You need to make sure they know this as soon as they come to your home page.
Howard was also in support of our continued focus on the value of the data we’re accumulating from our users. We will know a lot about them –including where they’re going, how they’re getting there, where they want to go, and ideally, when. We also have an effective way to get them to provide additional information (i.e., bribe with miles) and a seasoned sales team to sell those services to industry behemoths (by sales team, I mean me). It isn’t always easy defending this as a major monetization strategy but Howard got it. Howard got pretty much everything. Perhaps that’s why he saves all those businesses. Thanks for a great meeting, Howard!
