What I learned during a 30-year career as an
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What I learned during a 30-year career as an entrepreneur

by Deb SchwarzFebruary 11th, 2019
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<strong>What I learned during a 30-year career as an entrepreneur</strong>

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What I learned during a 30-year career as an entrepreneur

My journey as an entrepreneur has been an odyssey I’m stepping away from after 30 years. Entrepreneurs tend to hover between calculated risks and foolhardiness with a greater degree of comfort than most people. During three decades of running a business, I’ve learned as much from failure as success. Failure is often the better teacher. As I look back on founding a company, here are my “birthing” lessons; they’ll apply to new and emerging companies alike.

Look before you leap, but leap

In my company’s early years figuring out how to make payroll was often the cause of many a sleepless night. Later as that worry subsided, I personally guaranteed millions of dollars in order to afford the costs of bringing on a big, new client or to acquire a business. My friends and family shuddered at the risks I took, but I did it because I believed I would succeed. I didn’t always succeed, but I did often enough that I felt validated in my decisions and outcomes.

Good ideas can die and become better ideas

Much to my consternation, I saw ideas work brilliantly for one client but not others. For example, my team developed a digital platform to provide an aerospace company with a rights-management service. The service managed a treasure trove of images the client could, for instance, monetize for advertising, marketing and more. The platform works beautifully, and I assumed other clients would want it, too. But I was wrong. So my team revamped the service as a virtual-research platform to deliver on-demand research and intelligence for clients; it’s one of our fastest-growing services.

I also found that clients presented great opportunities I wasn’t looking for. For example, after helping a news network streamline its research library, they asked my company to do the same for their massive video and film library. Other customers followed, and I even acquired a company to support the new line of business. I learned the sales process isn’t linear. Listening to a client but also what a client doesn’t say (i.e., the between-the-lines stuff) is critical to finding the opening and leveraging an opportunity.

Be thoughtful about whom you trust

When my company began to really grow, things happened in a fast, furious way. For instance, hiring others to do administrative (i.e., non-billable) roles was a must, but I often put expediency ahead of thoughtfulness. My interview questions were all over the place. If I liked the person and they made good eye contact or had a great handshake and came with a good-enough resume, I often hired them. Sometimes hiring like this worked like a charm!. But when it failed, it was either a disappointment or a disaster. I suffered through embezzlement that almost shut down the company because I put someone I liked (and trusted) into a fiscal role he was not qualified for. I had another key employee who, after a bout of heavy drinking, never came back to work leaving me to carry on solo at an important investor meeting. I learned that trust was to be earned not to be “sensed” from a good vibe. My business launched as a staffing company, but it took a while and some costly mistakes, before I turned my staffing expertise on myself.

You have many bosses

Some friends have told me they envy me for being my own boss. But every client I’ve had has been a boss. Managing these client relationships means holding on when strong allies leave; weathering new corporate mandates; persevering through client mergers and acquisitions and carefully maintaining personal capital. There were many times I longed for a job with responsibilities that ended with the work day.

Live to work, or work to live?

My friend ran her own business, quite successfully for a time. I valued her advice, and she made a profound impact on how I conducted my business. But we differed strongly on one point: I love working; she saw work as a means to an end. That worked while her business was growing. But a downturn in her industry put an unfortunate halt to all of that. It would be disingenuous for me to say the financial rewards of having a healthy business are unimportant. Running my company has been my raison d’etre and passion. New projects and clients excite me. My friend and I were at opposite ends of the spectrum in our attitudes on this one.

Timing is everything

Being a pioneer has it advantages but can also mean your offering is ignored, even feared. I took a comparatively staid profession (i.e., librarianship) and turned into an outsourced services business. Many of my peers saw this as betraying a profession; they feared I would diminish the librarian’s role. Thirty years ago, I had to fight a public-relations battle to convince others to accept my business model. I pivoted many times and adjusted my business plan to anticipate changing conditions. Today outsourcing a wide array of tasks, functions and even departments to outside experts is a common, accepted business practice. Lawyers, accountants, actuaries and others outsource their work. To win, I played the long game. And that’s still a good play for today’s entrepreneurs.

Plough ahead in spite of the terrain

I ran a services business in an industry primarily populated by female professionals. And although procurement departments and government agencies always ticked off the box indicating my firm was a woman-owned business, it never won me any work. If I had run an engineering, manufacturing or construction firm — typically male-dominated industries — maybe my gender would’ve worked to my advantage, maybe not. Like most women, I received patronizing comments and even some degree of sexism. I fired my first accountant when — after looking over my company’s then faltering finances — he suggested I should consider marrying again, preferably a man with money. According to my one-time accountant, my “little business” was going nowhere.

I ploughed ahead and shrugged off those and other comments in the years ahead. Maybe I did that because I’m a female Baby Boomer with a higher tolerance for patriarchy, or maybe it’s my personality. Reaching my goals was most important. That said, patriarchy, ageism and sexism are real; how an entrepreneur deals with these things depends on the severity of the situation and the entrepreneur’s personality and circumstances.

Entrepreneurship isn’t all about money, but money matters

Working at something I’ve loved and had some success doing is rewarding, some would say priceless. But I didn’t do it for free. I’ve been lucky to work hard at something and go beyond supporting myself to become financially comfortable. It took a long time and patience to get there. Many business success stories feature serial entrepreneurs who get millions (or hundreds of millions) in venture capital or other investments, sell their startup and move on to the next big thing. I started my company in 1986, spent nearly 30 years growing it and sold my majority stake to a private equity firm in 2015. To paraphrase John Lennon, life happened while I was working and growing my company.

Parting thought

I remember my failures more than my successes, but not with bitterness. I remember what came after the failure: Deconstructing the failure and going over why it happened. Applying what I learned is how wisdom and experience triumphed over blind optimism. It’s a lesson any entrepreneur will understand.


Deborah Schwarz founded Library Associates Companies (LAC), a boutique temporary staffing company for law firms in southern California, in 1986. The business has grown into LAC Group, an organization with multiple divisions and offices in the United States and the United Kingdom.