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Secrets of Success: Tim Berry

We’ve launched Secrets of Success, a new weekly interview series here at’s Small Business Forum. I’ve asked some of the smartest, most innovative, most successful people I know to share their insights and success secrets.

Meet: Tim Berry. Tim has had a very busy career. He is the founder and chairman of Palo Alto Software and; the co-founder of Eugene Social, Apps37 and Borland International; and the author of books and software. Tim also teaches entrepreneurship, blogs at Planning Startups Stories and is an angel investor. Check out his website at His latest business undertaking is Eugene Social.

I’ve known Tim a long time, and his deeply thoughtful (and truthful) answers below are one reason he’s one of my all-time favorite entrepreneurs.

Rieva Lesonsky: What did you want to be when you grew up?

Tim Berry: I changed over time. I wanted to be a football player first, then a folk singer, then a poet—I still haven’t figured this out yet. Although, come to think of it, I’m not sure when exactly I grew up: Possibly not until I gave up [writing] novels, concentrated on being a journalist, and reluctantly took up business writing to up my income. Or maybe when it was when I decided, soon after that, that I actually liked business writing. And maybe when I gave up journalism in Mexico City and returned to the U.S. to get an MBA [which he did, at Stanford].

Lesonsky: Why did you start your own business?

Berry: Two things: First, I wanted to do the work I liked doing (forecasting, market research, planning) instead of supervising others as they did the things I liked doing. I was a VP at Creative Strategies International, in charge of what we then called personal computer software, with six people reporting to me. I’m a doer more than a manager.

Second, I wanted to earn more money than what anybody in his or her right mind would pay me as salary. I loved the work but wanted, if I worked nights and weekends, to earn more for my extra production. And I was married with four kids at the time, living in a 1,200-square-foot house with one bedroom shared by all four kids.

Lesonsky: Did you experience a pivotal moment on your way to success?

Berry: Yes: The successful launch of Business Plan Pro in 1995. I’d been stubbornly insisting, for years, on changing my high-end service business to a product business. I developed and sold business plan templates that were essentially failing in the market because the world didn’t understand templates as products. Finally, in 1994, in financial crisis, I bet the business on a stand-alone Windows application in which I controlled the whole relationship with the user, not just, as in templates, the financial formulas. My wife and I were deep in debt, but we bet everything we owned, and I found coding help willing to speculate on a percentage of future revenues, and a sales representative who understood retail packaging. Business Plan Pro changed everything. I haven’t focused seriously on consulting ever since. We achieved the goal of changing from selling hours to selling boxes (well, boxes back then; by 1999 it was boxes and downloads).

Lesonsky: What’s the best small business advice you ever gave and/or received?

Berry: Sadly, ironically, the best advice I give is not to listen too much to advice. The overabundance of entrepreneurship advice in the world suffers from the problems of survivor bias, copycatting and groupthink. What worked for whoever is giving the advice was then, in that market, that time, with those resources, and those strengths or weaknesses. Nothing generally applies. It’s all case-by-case.

However, I am grateful for good advice I got along the way. Most of it came from my wife, and doesn’t summarize well; it was steady advice over decades, a matter of instincts about people, conservatism about money, and encouragement when it really mattered. There is no underestimating how important to an entrepreneur is a spouse who says, “Do it. If you fail, we fail together. We’ll figure it out. Do it.” That’s what my wife said, more than once, at key moments.

I’m grateful for advice I got from a then-client of mine, still a good friend and lately a business partner, who told me to get over my do-it-yourself instincts and hire a professional graphic designer to do packaging and logo and such. It felt like a tax, at the time, because it added nothing to the value of the software. But it was critical. He was so right.

And maybe the best advice I gave was when a former student (I taught an entrepreneurship course at the local university, for years) asked me what to do about his spouse not believing in his business plan. I told him: “Trash the plan. It’s infinitely easier to develop a new business plan than to find a new wife.”

Lesonsky: What’s one “best practice” more entrepreneurs should be embracing?

Berry: I apologize for even answering this question after what I just said, which makes it pretty clear I don’t believe in best practices.

Still, ignoring the irony, I say more entrepreneurs should get over themselves and give the customers value. Don’t ever sell anything you wouldn’t buy.

And get over yourself and walk in the customers’ shoes. Nurture empathy. Product development and marketing are basically understanding what other people need, want, think and feel. The secret is empathy.

Lesonsky: Do you have a 2014 small business prediction?

Berry: Crowdbranding. There’s a steadily growing trend towards your brand being owned not by your marketing but by your customers. More and more, you aren’t what you say you are; you’re what somebody else says you are.

Lesonsky: Do you have a favorite book?

Berry: Lately, yes, Nancy Duarte’s book Resonate. Also the soon-to-be-released The Age of The Customer by Jim Blasingame.

Long term, over 30-plus years in business, the best business book I ever read, and one of the first I recommend, is Growing a Business by Paul Hawken. It was written in the 1980s but its core is as true today as it was then.

I should also mention The Art of the Start, Guy Kawasaki’s brilliant and inspirational book for startups. And Seth Godin’s All Marketers are Liars. And the Heath brothers’ Made to Stick. And Malcolm Gladwell’s Blink.

Whoops! Did you say “book,” as in singular?

Lesonsky: Is there a quote you find particularly inspiring?

Berry: Coincidentally, I just rewrote my favorite quote over the last weekend. The original is William Blake, from Proverbs of Hell:

Anything possible to be believed is an image of truth.

And my rewrite:

Truth is a believable story.

I hope that doesn’t come off as advocating believable lies as truth. It’s just that people seem to think that data is truth, and research numbers are truth, and I think real truth is most likely to live in a story. And I love the numbers, but to frame it, support it, temper it. The core is the story. And that’s as true for business as for life.

Want more advice to grow your business? Connect with on Facebook or Twitter.

Rieva Lesonsky

Rieva Lesonsky

Rieva Lesonsky is CEO of GrowBiz Media, a media and custom content company focusing on small business and entrepreneurship. Email Rieva at, follow her on Google+ and, and visit her website,, to get the scoop on business trends and sign up for Rieva’s free TrendCast reports.
Rieva Lesonsky

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