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Dream Job Diaries: A Day in the Life of a Recently Graduated Start-up Entrepeneur

The Dream Job Diaries is a new semi-regular feature that investigates the reality of various glamorous post-college paths. If you have a job or know of a job you would like to see profiled, send me an e-mail.

Update 10/8/08: I inexplicably reversed the names of Lance and Dana in the original version of the article. It has been fixed below.

9 AMWiggio Team

The world headquarters of Wiggio Inc. can be found on the first floor of a triplex, situated across from the fire station in a gentrifying North Cambridge neighborhood. At 9 AM, one Friday morning this past September, Dana Lampert arrived to start the new day. He had been at the office until 9 PM the night before. This was considered good. The two nights previous he had been there until 3 and 4:30 AM, respectively, coaxing along a tricky upload of their web site to new servers.

Dana is soon joined by Lance Polivy, his college friend and co-founder of the company. They begin their day by diving into the more than 100 product feedback messages that have gathered over the past 24 hours. The feedback concerns Wiggio’s flagship (and only) product: the website.

This site was launched by Lance and Dana the previous spring, while they were seniors at Cornell. The idea is simple: it makes organizing groups easier.

Here’s the pitch: with one web site, your group can setup shared calendars, construct polls, store files, and send mass text, e-mail, and even voice messages to members. Their primary market is student groups, though its potential audience is wider.

In this early start-up stage, Lance and Dana feel it’s important to respond personally to every piece of feedback. The process is tedious, but it helps keep the founders connected to the users. For a web start-up, users are everything. Without them, all you have is a fancy web site and a business plan.

10 AM

Dana retreats to his office for a conference call with another technology company. The firm wants to know more about Wiggio. These informational chats are typical for new companies: you never know what might shake loose.

10:30 AM

Dana rejoins Lance They crawl the web, searching for the e-mail addresses of student leaders. The addresses are painstakingly entered into a spreadsheet, where they’ll later be merged into a mailing list used to spread the word about Wiggio.

As Dana notes, a surprising amount of his time is dedicated to “copying addresses and doing mail merges.”

“That’s the thing about a start-up that makes it different from a regular job. If you don’t do it, no one else will.”

12 PM

Attention is turned to hunting down a bug that was reported this morning. It concerns the site’s polling feature. Lance and Dana join Rob, one of the company’s developers.

Rob, along with his brother Derek, are the two programmers that built Wiggio. Their office, which is adjacent to the room shared by Lance and Dana, defines the programmer cliche. A line of six flat screen monitors spans a long desk. The side wall is decorated with a collection of programming handbooks that Dana describes as causing “visiting coders to drool.” An obligatory 24 pack of Coke Zero sits on a nearby filing cabinet.

Rob and Derek are the sons of Bob Doyle, a technology visionary and serial entrepreneur who owns the building Wiggio calls home. His office is next to his sons. The walls there are lined with an eccentric collection of books. Next to a three-volume series on classical physics sits a manuscript on ergodicity in probabilistic structures and a slim title improbably titled: Entropy and Art.

When I later visit, Lance points out a poster of a primitive looking 1980’s-era portable computer — a puffed-up, tan-plastic calculator-style contraption with a phone cord sticking off the side.

“That’s the first blackberry,” Lance explains. “Bob invented it.”

Bob, more than anyone else, was responsible for the transition of Wiggio the idea into Wiggio Inc.. He was the first major investor, back when Lance and Dana were still developing the idea at Cornell. He gave them the office space they use. He provided his sons to program the site.

This afternoon, Bob’s son Derek helps Lance and Dana hunt down the alleged bug. The process, it turns out, is messy. Fixing bugs is easy. It’s finding them that’s hard.

“This basically reduces to pounding away at the site trying to get it break,” explains Dana.

Pound they do, eyes transfixed on the screen.

1:30 PM

Dana makes a run to the UPS store. He’s shipping a box of promotional postcards to a contact at Yale.

He admits he spends a lot of time at the UPS store and dealing with shipping in general. Earlier this week he spent a late night unpacking the postcards from the large box they arrived in, and then repacking them into small boxes to be sent to individuals. The cardboard detritus of this missions still litter the conference room.

For a high-tech entrepreneur, Dana spends a lot of time with a box cutter.

2:00 PM

Dana begins hunting through the user statistics for the Wiggio web site, pulling out some trends that he and Lance like to follow. There’s probably some way to automate the reporting of these metrics, but that’s just one more non-urgent item on a crowded to-do list.

2:30 PM

An investor calls. He wants to discuss how the Wiggio team can deploy better analytics, and how this might produce real benefits. Dana spends a while brainstorming the different user behaviors that might be most important to monitor. They have to weigh the complexity of giving another task to Rob and Derek versus the insight it might provide.

This proves to be a core problem for start-up entrepreneurs. Everything is useful. Everything takes time. How do you decide what to do?

Imagine making those decisions two dozens time a day. Imagine that the wrong decisions could mean you’re broke and out of a job. Welcome to the world of Lance and Dana.

4 PM

I show up for a tour of the office. Chatting with Lance and Dana, I tease out the following origin story:

In the fall of 2007, Lance and Dana were taking an entrepreneurship class at the Cornell. Their final project was to pitch a business idea to a panel of venture capitalists and professors. Wiggio was what they came up with.

“We gave our pitch to the panel, and they said ‘you’d be crazy not to do this,'” recalls Lance “We had heard from the other teams in the class that the panel had been harsh, so this was a big deal.”

Not long after the presentation, Dana’s dad put the his son in touch with Bob Doyle. “Bob got excited,” Dana recalls. “He said that him and his team [i.e., Rob and Derek] could get this up and running in like six months.”

Development started in January. A prototype was launched in April. The next month, when graduation arrived, Lance and Dana committed to making the company their full time job.

Here’s what struck me about their story:

(1) Wiggio is very good idea. To test out the first prototype, last April, Lance and Dana sent the address to a group of their friends. By May they had 1200 users.

This is phenomenal growth. It turns out that student group software is incredibly viral. If you join a group that is using Wiggio and you like it — which most users seem to — you’re going to convince the other groups you’ve joined to do the same. The effect then spreads to these new members, who convert their other groups, and so on.

(2) Even though Wiggio is a very good idea, it was still very hard to get funding. After Bob’s initial investment — about a fourth of what they needed to fund their first year of operation — Lance and Dana thought the rest of the money would follow easily. Business professors loved the idea. Investors loved the idea. The site was built. It had been proven. Raising cash should be no problem.

But it was.

It took four months for the rest of the funding to come through. Lance and Dana moved to Massachussets in June, but it wasn’t until just recently — earlier in September — that they received their first paycheck. Practically speak this means three things:

  1. They were living off of their savings accounts the entire summer with no guarantee that they would ever see any money for their efforts.
  2. Dana had to commute from his parent’s home, a thirty minute drive, to save money.
  3. As Lance puts it: “we ate lots of peanut butter sandwiches.” This sounds like a line, but they mean it. They were authentically pleased that now, with funding finally in hand, they could afford to eat lunch at the working class pizza joint down the street.

5 PM

Lance’s dad arrives from upstate New York for a visit. “I’m glad Lance is in a stable job, like a start-up, instead of going into something risky, like banking,” he jokes.

This premise, it turns out, is true. Both Dana and Lance had high-end job offers when they stumbled across the Wiggio idea. Lance turned his down. Dana’s management consulting gig, however, has just been deferred.

I ask why he’s holding onto his job offer if he’s committed to Wiggio? He says something official about the consulting firm being happy about the experience he is gaining.

Lance shifts uncomfortably.

5:30 PM

As I prepare to leave, I ask Dana what he would tell students who are interested in following a similar “glamorous” path, such as launching their own business.

“It’s not glamorous,” he replies. “I was up the other night until 4 AM trying to record a video, and the audio kept failing. That’s not glamorous.”

“There’s a lot of responsibility. More than a regular job. You have to push yourself.”

I ask him what makes this path worthwhile.

“It’s liberating to set your own schedule. To be your own boss.”

He then retires to his office to continue hunting down e-mail addresses for their student leader campaign. After that, a development meeting. Then, if all goes well, a short night’s sleep before a new day begins.

(The photo above contains, from left to right: Derek, Dana, Lance, and Rob.)

4 thoughts on “Dream Job Diaries: A Day in the Life of a Recently Graduated Start-up Entrepeneur”

  1. You might want to look at some other WP theme, the narrow column for main text is a waste of screen space on large screen (22+)

  2. @AC,

    for me it is easier to read, because you can cover many words at a glance as a rapid reader. If the lines are long, reading becomes slower.
    some people may be able to cover two lines at one glance with this format.

  3. Its really inspiring to hear of students and grad’s
    thinking and living outside of the box, creating their own maps and
    not treading the well trodden path and instead creating their own
    destiny. Thanks for the blog.


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