Business & Tech
    Next Score View the next score


    Two ways you can attain workplace nirvana. Or something like it

    for 01kirsner -- Entering StartUpLand: An Essential Guide to Finding the Right Job (Oct 10) by former entrepreneur, VC and Harvard Business School professor, Jeff Bussgang
    “Entering StartUpLand” author Jeffrey Bussgang is general partner at Flybridge Capital Partners.

    Let’s talk about your ideal workplace scenario: Does it involve setting your own hours, and being able to work from a chaise lounge on the back deck? Or working intensely with a tight-knit group of colleagues to help a startup find success?

    Two books from Boston authors, both being published next week, lay out two possible paths for motivated workers of any age.

    “Reimagining Work,” from the co-founders of the Boston startup Catalant, describes the chaise lounge lifestyle: With the right skills, you can easily market yourself to clients around the world, set your own hours, and become a one-woman consulting colossus. “Entering StartUpLand,” by venture capitalist Jeffrey Bussgang, is a newbie’s guide to the realm of startup companies, intended for people whom Bussgang dubs “joiners,” the folks who sign on to help build the company after it has been founded.


    Bussgang is a former entrepreneur — and also a “joiner” — who has been through an initial public offering and now puts money into new ventures as part of the crew at Flybridge Capital Partners.

    Get Today's Headlines in your inbox:
    The day's top stories delivered every morning.
    Thank you for signing up! Sign up for more newsletters here

    “All of the books about entrepreneurship are focused on the founders — the one on the pedestal — and not the ones you need to make the company run,” Bussgang says. “And most people have no idea how to join a startup.”

    First, Bussgang advises, don’t imagine that lobbing in your CV via a website is going to get you much attention. Old-school networking is still powerful: going to events in the startup community, and getting to know people who can make warm introductions to their employers, or put in a good word when you do apply. And once you get the interview, you need to be knowledgeable about the company, its offerings, and its competitors.

    “Startups want you to come bearing gifts,” Bussgang says. “They want you to have studied their industry, and talk not just about the online marketing campaign you ran last year, but the campaign you could run for them. They want you to critique their campaigns and give them ideas.”

    Some of the roles that startups are trying to fill would be familiar to someone who began their career in the Eisenhower era, like sales and finance. But others, like “growth manager,” are of more recent vintage. (That role focuses on collecting data, analyzing it, and testing new initiatives that may fuel the company’s growth.)


    How do you figure out which startup might be the next Facebook, and which might be a pile of rubble in two years? Bussgang writes: “One way is to ask a handful of insiders. Find the top three venture capitalists, angels, startup lawyers, and headhunters in your target geographical market and ask them to name the three hottest companies that match the domain and stage you are interested in (and then the bonus follow-up question: Will you introduce me?)”

    But buying a ticket to “StartUpLand” shouldn’t be seen as a path to instant millionaire-dom. “You’ve got to do the thing you’re passionate about,” Bussgang says. “Startups are marathons and not sprints. You can’t be looking for the quick hit. There has to be intrinsic value to your time there, and not just financial value.” He notes that he has been an investor in plenty of startups whose shares didn’t wind up being worth a cent.

    For those who dream not of IPOs, but of meaningful work that can happen when and where you want it to, there’s “Reimagining Work,” written by the co-founders of Catalant, an online marketplace for freelance consulting services. (It was originally known as HourlyNerd, and its backers include billionaire Mark Cuban.)

    “Gallup has been studying workforce attitudes in the United States since 2012,” they write. “Its most recent ‘State of the American Workplace’ report revealed that 70 percent of people do not feel engaged at work. Only 13 percent feel proud to work where they do. One in four admit that they are ‘actively disengaged,’ which Gallup defined as being so emotionally disconnected from the workplace that they were acting out on their unhappiness.”

    Part of the reason for that dissatisfaction, argues co-author Rob Biederman, is that “jobs today are largely a remnant of the factory system. Everyone comes to the same place at the same time and does the same thing every day.”


    “The more you know about how poorly many big companies operate,” he adds, “the more you realize that that system may be on its last legs.” The authors propose an alternative to the 9-to-5 grind: “folks can make work fit into their lives, versus making their lives fit around their work,” in Biederman’s words.

    Being an “elite, on-demand” worker — a.k.a. a freelancer — isn’t for everyone, they admit. But it’s ideal for people who may prefer semi-retirement to full-retirement, are trying to balance work with parental responsibilities, or may live somewhere where there just isn’t a local market for their skills.

    But just like StartUpLand, an office on the back deck isn’t for everyone. Biederman says it is important to do an honest assessment: “Are you okay with — and ideally, energized by — a relatively more solitary day-to-day? Can you self-motivate?” His co-author, Pat Pettiti, says that a key to making the transition from full-time work to freelancing is “finding one or two initial customers, so that you can make the jump with confidence. Many freelancers start by contracting with their most recent employer, which can help both you and them with the transition.”

    “Reimagining Work” predicts that in the future, “more people are going to have a healthier relationship with the workplace,” that “work will be done better by people who are happy to be doing it.” Bussgang argues that “people who work at startups are categorically happier with their jobs and with their careers than people who don’t.”

    If you believe that “happy worker” is not, in fact, an oxymoron, one of these books may lead you to that nirvana.

    Scott Kirsner can be reached at Follow him on Twitter @ScottKirsner.