Bill Hobbs

May 27, 2015

Bill Hobbs and I met at Norwood, a stately brick-red townhouse on West 14th Street. Norwood turned out to be the perfect setting for a conversation about writing, entrepreneurship, and the refusal to give up when the going gets tough. Bill, who’s a writer, businessman, publisher and ex-actor, knows how to balance business with creativity, and how to make a living blending the two together. “Independent people are really the new economy,” he says. “I think you can make money and survive and enjoy your life now without relying on ten people at the top of an industry to do it for you. Just do a little extra work.”


How would you characterize what you do?

I do a bit of creative and a bit of business. I’m comfortable doing both. I advise tech startups, so I work with some of these growth-stage companies. I help them understand how to take the vision that they have and create a strategy around how to achieve it. I sometimes help them as they go through execution phase to make sure things stay on track, to know that they’re building the type of company that they intended. On the creative side, I love to write, and I’ve written three books, two business books, and a children’s book that’s not sold yet. So I’m in the midst of learning the children’s book market, and trying to meet people that may share an interest in this particular subject, which is helping animals. It’s a book that’s a cute, fun book, but it also has a message of helping animals—i.e., instead of going to the pet store and buying a puppy, think about adopting one.


Are you a person who goes into these projects with the intention of selling them so that you can support yourself, or are you thinking Pulitzer prizes and literary awards?

I kind of fell into writing. I started out in the business world doing sales, and then got into turnarounds for businesses within the Fortune 500.


I’m a layperson. Can you define what a turnaround is?

If a business is struggling in some way, I come in and I say, look, you’ve got a framework, let’s look at what’s working and let’s look at what’s not working, and then let’s figure out a strategy to get you back on track, to get you profitable, to grow your business.


So you build rather than destroy?

Yes. That’s a good characterization. I love to build stuff, hence the writing. So the writing kind of came out of that. I had just taken over another business that needed some help. I had a sales team, and the team had people on it with varying levels of experience and ability. I thought, I’d love to give them something that’s short and to the point so that they can really get on the same page, and then I can work with them to help them grow as individual professionals. But there needed to be a base level of understanding. So I started putting together this little 15 page guidebook. And somewhere along the way it got to 80 pages. It just poured out of my head. I don’t consider myself a writer—I mean, I make money writing, but my education was in economics, not writing. I have worked on writing a novel, and I wrote a cool story. It’s much harder, because you don’t have the same framework as non-fiction.


Writing fiction feels a bit like the Wild West—when I was a fiction writer I couldn’t make things happen. I didn’t know how to move the action forward.

One of my favorite writers is Michael Lewis. I love Liar’s Poker because he told a story, and he really created these characters that you started to care about. I love the fact that he is telling us a story about his life on Wall Street, which was kind of absurd. Here’s this 26, 27-year-old advising people on their financial futures.


That’s how I felt about teaching. I was 27, and the whole time I was thinking to myself, “I can’t believe someone is actually allowing me to teach college.” Sometimes you get jobs where you think, “This is impossible. And unwise for my employer.”

And I think that was his point. So I ended up writing this thing, and a friend of mine had written a couple of books. We used to chat, and one day I said, “Oh that’s so cool that you’ve written a book.” And he knew what I was working on, and he said, “This is your book.” And I said, “I don’t really want to do a book.” And he said, “Well, you’ve pretty much done a book.” And I said, “I keep thinking about all of these stories of when I was completely incompetent, just starting out in business, and the things that got me there, and that’s kind of what’s driving this.” And he said, “Well, why don’t you throw some of your stories in there?” So I did. Some of it is based on truth, and some of it is anecdotal stuff that has happened. I put that book in front of a couple of big publishers, and they both loved it. And then I found an agent, a major agent, and she loved it. And I thought, “Oh, wow, I guess I could do this writing thing. Cool.” And the agent said to me, “This book reads like a novel. It’s amazing. I want to keep turning the pages.” So we ended up doing a contract. Then I found out about the book world.


Ah, yes. The cold, hard terrible truth about the book world.

My agent said, “Bill, I’m not putting this in front of anybody until you’ve built your platform.” I had conversation with one of the acquisitions editors as well, and she said, “I love your book, but you need to be speaking three times a week. Nobody’s ever heard of you. People don’t just walk into a bookstore and see a book on a shelf and buy it.” Theoretically the publishing company could have made it happen, but that’s not the way the business works anymore, unless you’re a celebrity. I had to look at it objectively. I was at a point where I’d been doing this Fortune 500 big business for so long, and I never intended to be doing it as long as I had. I suggested to one of the acquisitions editors that we just do a contract. I said, “I will quit my job, and I will tour.” She said, “That’s great Bill, but that’s not how it works. You actually do it the other way. You show us that you can make money, and then we invest in you.” But I was at a point where I wanted to change, so I set up all these talks at colleges and universities. I went to talk about general business things to start to build my platform. While I was there, students started asking me, “What should we do before we graduate to make us more marketable to companies?”


What happened next?

My current book that’s actually making money right now came out of those talks with the college students. They kept asking me all these questions. I started writing down the things they wanted answers to, and I paired that with my experience as an employer, hiring people and helping people to say, wow this person’s amazing, they have all of this great experience, they have a great background for what I’m looking for. So I tried to put all of that together in a short, easy-to-read, utilitarian text that these students could have. So it’s based on the concept of you figuring out how to brand yourself. Personal branding is not a new thing, but doing it takes you actually saying to yourself, yes, I’m going to do this. I’m going to think about my brand. And that means asking yourself questions like: what are the things I could do to round out this picture of myself so to do whatever it is I want to do? The idea was to give these students a framework. It doesn’t say you should do this or do that, it says: Think about this. I wrote it for career changers or people who were new to the job market, because the concepts are global. Universities liked it, and they started buying it. Wash U came to me and said that they wanted to make it required reading. But to go back to the original story about looking for a publisher for my first book, I realized that if I was going to build my own platform, there was no point in having a publisher aside from the initial investment. So I started my own publishing company, La Plata Press.


What’s the biggest challenge you face in your work?

The challenge for me is to figure out whether or not a venture is producing enough money to be worth doing. Should it be that way? Whatever. For me it’s that way. I didn’t feel I was a writer until I started making money on my books. The hardest thing is to believe that the reason you originally started a project is enough to drive to you to a point where you get to the other side.


What do you do to maintain the faith that you’re actually going to get to where you want to go?

  1. Realize that it can be successful or not successful and that some of the factors are on me, but some of them are on the audience.
  2. Analyze the hell out of what I’m doing. For my second book, I looked at every single book that was out there. I looked at what other books didn’t have, why other books didn’t reach the audience the way they should.
  3. Don’t give up. Sometimes you don’t feel like moving forward. Sometimes you feel like giving up. But for me what pushes me through is that I can’t give up. I just don’t have that option. When I do a project I have enough people around me who are emotionally involved that I’m not willing to accept that something is a failure. It’s just not going to happen.
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