Silicon Valley veteran Bill Wesemann knows sexy. With over 30 years experience, Bill has done it all, from selling computing services in the pre-PC era, through running worldwide sales working for Steve Jobs at NeXT and an IPO at Genesys, to angel investing and advising today. Below, Bill shares his insights on how delivering and selling enterprise software has come full circle, as well as a surprising story about the darker days at NeXT.

How did you get started in technology?
“In 1981, I was a pitcher in the San Diego Padres organization in need of surgery.  (By the way, the lifestyle of a minor league baseball player is similar to working for a startup.  You sleep when and where you can, and if you win that night’s poker game, you upgrade to the buses’ spacious overhead luggage bin.) Waiting in the doctor’s office for my surgical consult, l picked up a copy of Forbes with an article that changed the course of my life. It featured the Top 20 information services companies, among which were several big players selling computing capability directly to end users, including Tymshare.  I decided on the spot that was my next step and before too long I’d landed the job I wanted in sales.”

What has changed since the sexy pre-PC era?
“What I find really interesting is what was sexy at the start of my career in the early 80s has come full circle.  What made Tymshare and its competitors so revolutionary was that the buyer was the end-user and didn’t have to be hardcore programmers to use our service.

Just prior to corporate adoption of the PC, Tymshare offered “fourth-generation” software that allowed analysts to quickly develop applications and empower the end user.  In addition to owning the X.25 packet network called Tymnet, Tymshare also had early versions of email for which we charged $0.25 for every 1K characters.  Can you imagine that cost structure today? Needless to say, with an uncapped pay-as-you-use model, the bills got very big, very fast. As companies struggled to contain costs and set standards, a new regime run by the freshly-created Director of MIS, emerged.  With increased PC adoption, early versions of fixed-price packaged software, and solutions moved in-house, the model unraveled. In 1984, Tymshare was sold to aerospace manufacturer, McDonnell Douglas.

Fast-forward 30 years, and with the advent of SaaS, cloud technologies, social, and mobile, and the end users are once again discovering their own solutions. With today’s multi-tenant SaaS architecture, the ability to deliver cloud services anywhere to any device, and cost-effective per seat or pay as you go pricing has taken the enterprise software industry by storm. As vendors like Salesforce.com have shown, it is more cost-effective, scalable, and flexible to use on-demand could-based software.  So we have come full circle, only this time the economics favor cloud-based applications.”

What’s sexy today?
“I think the rise of angel investors in the past decade has been very good for enterprise all around. Early stage investors can not only participate in advance of seed rounds, but can contribute more than money. Not only can I share domain expertise, but I am also a partner and true fan of the business and the founders.  While the interests of traditional VC models and what is best for the business can sometimes be at odds, angels can be more patient and understanding of the ups and downs inherent to an early-stage company. Because we can become personally involved with the business, I believe this trend will continue to have a huge impact on the success of a startup.”

You know this post wouldn’t be complete without a Steve Jobs story, right?
“Well, I figured.  Let me quickly back up to the time just before I went to work for NeXT and set the stage for a classic Steve story.

When Windows 3.0 put a GUI on enterprise applications, people could actually use them – talk about sexy for the enterprise!  Before applications were natively built with a GUI (think PeopleSoft in the late 80s), we sold tools to augment mainframe applications with a Windows or OS/2 GUI. I sold one of those companies, Viewpoint Systems, to KnowledgeWare, a computer-aided software engineering (CASE) company whose CEO was none other than hall of fame quarterback Fran Tarkenton.  When I joined NeXT, I went from working with a CEO who knew everything about sports and nothing about software to a CEO who knew everything about software and could care less about sports. Talk about 180-degree change!

I mention CASE because it sets the stage for a classic Steve Jobs sales call story.  You see, NeXT sold enterprise application development software, so he actually had to go on sales calls.  This particular meeting was a big one with the US Postmaster General. There we are in a room in Washington DC, 20 guys in suits and the two of us (Steve clad in his classic uniform, of course).  Their very first question was, “Steve, can you tell me what you think of CASE?”  I cringed, and a full 30 seconds of silence passed.  Steve then pretends he’s going to sneeze and says into his hand as loud as he can, “It’s bull shit”. I cannot describe the stunned looked on their faces. Another 30 seconds of awkward silence passes and I say, “Next question?”  I’ve got so many of these great stories, but we’ll save them for a future post.”

What did you learn working for Steve Jobs that applies to entrepreneurs today?
“I will say the time I worked with Steve at NeXT were tough times for him. Some had started to write him off and he was struggling to find himself.   Even through the darkest days, the only time I ever saw him really down was when he briefly decided to give up the user experience and adopt the Windows GUI over the beautiful object-oriented interface we’d developed at NeXT.  Obviously he ultimately didn’t have to do it, but he almost conceded.  It was his spirit and relentless drive that never allowed him to give up.

I believe that those that were fortunate enough to work for Steve at any point in time are the better for it. I have had the privilege of working for many great companies, but I look back at those days as the best of my career.  We worked every day with a singular goal of doing something unique and contributing to something special.  It may sound trite, but that type of culture and unwavering dedication makes financial rewards secondary.   We got up everyday to hit a grand slam.  We weren’t satisfied with a base hit and we never gave up.   I think this is an important lesson for any entrepreneur that faces the fire, you’ve got to double down on faith and push forward.”

About Bill 

Bill Wesemann is a Silicon Valley veteran with over three decades of experience in enterprise software. He began his career in technology in the early 80s selling computing services in the pre-PC era with several successful exits. In the 90s, he ran worldwide sales for NeXT, led sales at Genesys, which went public 1997, and was then CEO of NextPage.  For the past decade, he been an angel investor, advisor, and on the Board of Directors LivePerson (LPSN).