Introduction

In the summer of 2015, I had a bit of an out-of-body experience. Three different inquiries came to me because of my experience building and running M Squared Consulting, a company I started in 1988 and sold in 2005, and for which I served as a board member until 2014. M Squared was an innovator in its day, being one of the first companies in the nation to match independent expertise to client project needs. We were in the Gig Economy before that ever became a term of art. Having been out of the company for two years, I was intrigued when I received this series of calls in the space of two months.

One overture came from a venture capitalist interested in building a marketplace platform for professional women who had left the workforce for family reasons. The platform would find them gigs, train them in the newest workplace tools, and provide a working mother forum. Another was from a private equity firm that wanted to create a marketplace platform for on-demand energy industry workers in eastern Africa. Staffing the oil fields was tough, so creating a qualified buffer of potential workers could smooth production issues. The final notion was from a pair of successful entrepreneurs in the technology space who were developing a marketplace platform for entry level professional hires that would eliminate the need for human oversight in the recruiting process. Like the common application in the college application process, this artificially intelligent front end would identify the best applicant for junior management-level hires.

All three of these ventures shared the “marketplace platform” element. At least one, the recruiting site, was being viewed as a major disruption to the current environment. The other two were viewed as an opportunity to target an underserved segment of a large marketplace. Perhaps most importantly, all three were technology plays being launched by technologists. The fact that these platforms were being created for human capital was not relevant to the enterprise. Even more simply, the services being developed were being built by guys who had never operated—nor funded—a service business, not even software as a service.

Given that a hallmark of my company was the high-touch service we provided our clients in the structuring of virtual consulting engagements, my focus in each of these discussions was around the human element of the process. I brought up questions about the nature of the interactions with the female consultants, oil field workers, and recruits, challenging why they would affiliate with the sites. I wondered why companies would patronize the service and discovered that sales models for the demand side hadn’t really been considered. One venture capitalist responded to my question about securing gigs quite cavalierly, saying, “We will just get all of the open job recs from Google.” I didn’t have the heart to tell him the consulting marketplace doesn’t work that way.

Nonetheless, we discussed revenue models, intellectual property issues, contractual considerations, and privacy implications. The brainstorming was incredibly fun and made me appreciate that the Gig Economy world I had once known was evolving even further.

Those discussions prompted me to reconsider this on-demand consulting marketplace in which I had operated for so long. Marketplace platforms were being built at a rapid pace, but could their algorithms really displace strategic judgment? In my experience, one reason clients used an intermediary was to eliminate the noise that was coming from so many automated feeds and online resumes. Having M Squared say, “You should really talk to Mary, Harry, and Chris, and this is why” was a relief for so many overworked and stressed managers. Could a great algorithm really provide a similar level of comfort and thereby eliminate the humans in the process? If we really drive all business innovation through our people, isn’t there some value to the people working the process by which we secure them? The very notion raises other questions, such as, as marketplaces proliferate, what would the consultants do: join all platforms or hedge their bets with the few that they like the best?

Additionally, I live in San Francisco, the home of the Uber mothership and its feisty competitor Lyft. A consequence of this is the never-ending stream of stories about the drive-sharing marketplace platforms and the ways these firms chose to treat their human partners, their drivers. All the discussions about whether Uber drivers should be employees or contractors seemed to drown out other segments of the Gig Economy. Stories about my old world, the high-end consultants and their experiences in the Gig Economy, seemed to be getting lost.

With that in mind, I decided to revisit the book I had written in 2001, A New Brand of Expertise. It focused on high-end independent consultants and the marketplace for their services. Beyond explaining what was then a new phenomenon, it offered guidance for companies that wanted to avail themselves of these services and best practices for the consultants pursuing the independent path. Although many of the business reasons for deploying on demand expertise have not changed, the landscape has. Due to this, the ways high-end gig workers need to establish their competency, market, and contract for services has changed. Similarly, companies can now access this expertise through many channels, so the internal vetting process becomes all the more important.

Moreover, companies must organize differently now to effectively deploy these gig workers. More importantly, they must empower their workforce in new ways, because not only are they engaging gig workers, they are preparing their own employees to become the gig workers of the future.

I was excited to revisit the subject, in part because I was no longer a player in the marketplace. Even though I was very even-handed with A New Brand of Expertise, it was still a promotional vehicle for my company, M Squared. Now, as the saying goes, I don’t have a dog in the race, so my observations on the companies, business models, and industry developments can be far more candid. By extension, more people in the field were willing to speak to me because I was perceived to be independent.

And speak they did. To better understand these new dimensions of the Gig Economy world, I needed, in the words of Harry Truman, to learn the history I did not know. To do so, I interviewed a hearty cross-section of CEOs, COOs, and CTOs of new digital platform companies. I learned about new platforms that targeted highly specialized expertise, like cyber security experts or big data scientists. I spoke with specialty consulting firms that had narrowly defined talent offerings like social media influencers or experienced interim managers. I met with entrepreneurs developing adjacent systems to help companies better deploy consultants and manage the contractual and payment aspects of a workforce comprised of independent contractors as well as contract employees. Conversely, I met with entrepreneurs developing platforms to enable consultants to access and purchase the types of insurance coverages and retirement programs they will need in the new world of work. Finally, I met with pundits in the field to get their sense of where we stood in this movement, at the crest or in the trenches, to better understand the future world of work.

Beyond interviews, I also became a participant in the new Gig Economy. (Or, should I say, more of a participant, as by definition I am an “Occasional Independent,” with some regular gigs and two paid board roles, as I will discuss more in Chapter 2.) I joined all of the digital platforms for which I was qualified and a few for which I probably was not, to get a sense of their process and communication with their community. I was deeply intrigued to see how many might produce gigs for me. Of the nine platforms I joined, three suggested opportunities for me. In only one case was the situation relevant to my background, which is an interesting data point, but just that: one point. As I explain in Chapter 5, you need to work the platforms for them to yield results, and after a while writing this book got in the way of that work.

I also became a client, using digital platforms to secure expertise for programming my personal website and market research services to capture data on different players in this new world of work. The programming project became somewhat of a nightmare, as I went through three different workers on two continents before I found one that could do the project as I intended. As that project finally progressed, the errors of the prior providers meant much more work was needed. I was not thrilled by that outcome, and neither was my new programmer, Phil, although it turned out to be a more lucrative gig for him. Being a client on the platform was instructive, at times surprising, and frequently frustrating, but helped to inform my perspective on the state of the art today.

As an aside, I even thought about becoming an Uber driver, but because I drive a Jaguar convertible, usually top down, that did not seem like a viable option.

Along the way, as I talked to friends and colleagues about the book, I became aware of a very important fact. Many people were clueless about the variety of business models in this new marketplace of talent. CEOs of companies that could really use a marketplace for big data geeks, for example, had no idea that such a site existed. The West Coast manager of a major consulting firm when we discussed some of my findings was relieved that someone was finally going to make sense of this new world of work. “I can only try,” I replied.

The result is a book that I hope will provide insight into a very timely subject. In some ways, perhaps it is too timely. My first book, A New Brand of Expertise, had no chapter notes, and this book averages 10 per chapter. That is because every week, if not every day, new information was coming out about the Gig Economy. I started my research in January 2016. Since I began, there have been four books discussing elements of the phenomenon and 3 major industry studies, most notably the first comprehensive report on the topic by the McKinsey Global Institute. There were also five industry studies, including the annual State of Independence in America report from MBO Partners, a report that is well respected as a consistent source of data on the field, and a new study by the industry association, Staffing Industry Analysts, called Measuring the Gig Economy. At times I felt that I was drowning in data, so I did my best to make sense of it. This was no easy task, as all of the studies had their own methodologies, underlying assumptions, and associated results. I tried to glean the salient facts, the ones that could best educate my readers on the inner workings of the Gig Economy.

What I have put together is a well-researched but not academic perspective on how and why the new world of work, the Gig Economy, operates and grows. Thriving in the Gig Economy will hone in on the most important aspects of these trends and the implications for individuals and businesses. It will explain the digital talent marketplaces and how they fit into the talent landscape, outlining their features and cost structures.

Although not a how-to manual, Thriving in the Gig Economy will hopefully provide a clear explanation of how the participants in the Gig Economy, from workers to client companies to service providers, can succeed in the new marketplace. It begins with a definition of the Gig Economy to ensure that we are all on the same page (pardon the pun). From there, it discusses the people in the Gig Economy, their numbers, demographics, and motivations. A natural counterpart to that is why and how companies use these free agents, something workers need to understand to thrive. The book then compares traditional intermediaries and digital talent platforms, explaining how they differ and how individuals can best use these tools to their advantage. The book dives deep into personal branding including a broad discussion of building a digital voice. Although perhaps less interesting to many but just as important is the explanation of the legal issues surrounding this work mode as well as practical tips for managing your practice. The intent is to provide a framework for the reader to create his or her own mental model for how to thrive in the new world of work.

The structure of Thriving in the Gig Economy is designed to ensure that the reader gets real “take home” value from reading the book. Chapters on sales strategies, pricing, contract provisions, and creating the optimal independent work environment are designed to provide real assistance to existing gig workers as well as those who may be contemplating the idea. Similarly, I offer guidance on running a successful practice, provide a listing of popular freelancer apps, discuss ways to procure benefits, and offer insights into creating community as an independent worker. Each chapter concludes with a “Key Takeaways” section to underscore for the readers the points they need to understand in order to thrive.

And even though the discipline is constantly evolving, I had to offer some thoughts about what the future could hold. The short story is the trend will only continue and build, so the future looks bright. Nonetheless, there are many legal, regulatory, and societal issues that result from this growth that will need to be addressed in the years ahead. As is often said about Wayne Gretzky, he was a great hockey player because he anticipated where the puck would be. Hopefully my readers will become even more successful participants in the Gig Economy by anticipating the changes the future could bring.

It has been an adventure developing the content for this book. I have learned so much in the process of its development. I look forward to sharing it on the pages to come.