Eyes way up in the sky, feet firmly planted on the ground

One of the hardest things for me as a start-up CEO was striking the balance between “selling” the big vision while remaining maniacally focused on the details. Sometimes it seemed as though everyone wanted to hear a different story – customers, employees, candidates, investors (especially those on opposite coasts!). My partner Eric put it best when he said, “keep your eyes way up to the sky, and your feet firmly planted on the ground.”  My colleague Gaurav points out that most founders give the “big picture” vision to external parties but do much less so internally. Founders often forget that teams need to be reminded of the broad company vision to keep morale high and turnover low.

Eyes way up in the sky

The startup CEO has to capture the imagination. I have found that most start-up meetings require “up in the sky” messaging. Like the coming attraction to a movie, the entrepreneur should confidently state a bold (but believable) statement of the future. The vision should be a couple of years out, not one, but not ten. Every employee or prospective investor should leave a meeting able to articulate the vision of the company.

When it comes to customer presentations and tradeshows, the same rules apply with a slight tweak in messaging to reflect their market knowledge. At Brontes, we started sales pitches by saying “imagine a day when dentistry is digitized like music or photography.” Potential customers (dentists) would nod in agreement. It was a hard vision to deny and we would spend the rest of the pitch addressing why we’d be the ones to do it.

Feet firmly planted on the ground

The details support the overall vision. Once you’ve compelled the audience by describing a future state, the key is to convince that you have the plan and ability to get there.  Those of us that have started ventures know how hard it is and that most businesses are built brick by brick.

Early stage company CEOs have to shown deep comprehension and appreciation of the product and tech. CEOs should be conversant on what technology platform a given product is built on, aware of the development schedule (and how far ahead/behind the project is) and he/she must be able to demo the product. At Sample6, I spent time in the lab trying to learn how a competitive product worked. I spent time at customer sites. I’d come back with real-world anecdotes about why the product needed to be made easier to use or ideas on how to pitch it differently. Most importantly, the quickest way to lose credibility with an engineering team is to seem removed from details or unappreciative of the complexity of their work. This is heightened when times are tough.

The start-up CEO is both a general and field marshall. The challenge is balancing these two roles – internally and externally.

Handshake.com meets 2013

In 1998, I co-founded Handshake.com, a marketplace that connected buyers and sellers for all sorts of services – from carpet cleaners to auto repair shops. Since Handshake came and went with the go-go days of the late 90s, I’ve spent a lot of time thinking about the mechanics of such marketplaces. Today’s online service marketplaces have been generally more successful than our foray. Recently, I tried a few to help with the construction of Founder Collective’s new office at 27th St in NYC.

Original handshake team going live in Dec, 1999

Original handshake team going live in Dec, 1999

First, I used TheSweeten, a site that matches projects with contractors/architects.  I posted images of our current space and a crude mock-up of the build-out I envisioned. I received 3 bids from vetted contractors and ultimately selected one of them. We then needed furniture moved from our Cambridge office, so I hired a Taskrabbit to bring it to NYC. Once the build-out was complete, I used Handybook to schedule and coordinate a plumber to fix an old water purifier and a handyman to assemble IKEA furniture. And last and most importantly, we hosted our kick-off party with catering from Kitchensurfing (a portfolio company). These services aren’t yet one-click and done, but they have come a long way in making it easier to coordinate moves, construction, catering and transportation.

Last week, at an ERA event, I was asked to share my lessons learned about these types of marketplaces. Here’s what I said:

1)   Pick a vertical, not many – One of the mistakes we made at Handshake was that we offered every service we could find in the yellow pages. However, we spent way too much time and money marketing the idea of an online service marketplace. If you’re trying to create a national brand, it’s hard enough to get consumers to keep you in mind for a particular service, let alone many.

2)   Control the money flow Much of the frustration around hiring service providers stems from challenges making payments(many want cash or don’t accept credit cards), whether to pay a deposit, and how much to tip. Additionally, if the marketplace doesn’t hold the money, it is far too easy for the service provider and customer to work around the system, and avoid fees or commission. If the marketplace isn’t stepping into the money flow, it’s likely because it’s not creating enough value for both customer and supplier.

3)   Delight both customer and supplier (but hold each accountable). Uber (also a portfolio company) does a fantastic job of this. The app knows where I am and where the cars are. Its just two clicks to call a car, my credit card is on file and there’s no tipping. But I’m most impressed (and surprised) by the driver’s reactions. They love the fact that they can rate me (1 to 5 stars) … the customer!

For the full Handshake story, click here.