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Leadership insights from co-founder of Yesmail

"Leading IT," a new WTN column by Geoff Bastow, will dissect topics that intersect with the region's information technology community, including: entrepreneurship in IT, insights from the area's leading IT CEOs and CTOs, and technology trends that are driving real business value and attracting capital.

Milwaukee, Wis. - At the dawn of the dot-com era and through its explosive, manic growth to its peak in March of 2000, Kenosha entrepreneur John Weiss was on center stage. He and his partners guided an Internet start-up to an IPO and eventual sale for more than $700 million in less than five years.

He's at it again, driving solid growth of another Internet-based company, but this time under the more practical business model that replaced the wildness of the dot-com era. His success in both worlds is testimony to the enduring nature of his leadership skills, and to his entrepreneurial agility.

The Internet world was unknown to most people when, in 1995, Weiss was convinced by a couple of weekend windsurfing acquaintances to leave his job as a sales engineer for a Kenosha manufacturer to join a Chicago start-up that would develop web sites and an Internet directory.

The company found success developing web sites for marketing and advertising firms, but soon was hearing from clients that traffic on those sites was low. Weiss and his business partners had the answer to that problem with the development of their directory technology, which was operated under the Starting Point name. To make it work, however, they needed a way to pull people to the directory - and do it quickly.
In that fast and furious world, they came up with a strategy of increasing traffic to their Starting Point directory: Companies that submitted web sites to the directory were asked if they wanted information about other sites with similar topics included with their own information.

The strategy worked. By 1997, Starting Point rose to become one of the top 10 most visited sites on the web, but something more important was happening.

The company was at the forefront of something that would become huge: opt-in, permission-based e-mail marketing - relevant today as a best practice in e-mail marketing etiquette. Rebranded as, the business saw tremendous success based on its ability to use technology to manage its database of millions of e-mail addresses, and to track how people with those addresses were responding to offers.'s rapid ascension led to a $37 million public offering in the fall of 1999, yet bigger things were on the horizon. Within six months, Weiss and his three business partners sold to CMGI, Inc. for more than $700 million, with Weiss staying on through the fall of 2000.

Even after accounting for stock sale "lock-outs" during the NASDAQ's post-bubble drubbing, Weiss pocketed millions - enough to design and build a home overlooking Lake Michigan in hometown Kenosha and to invest in other technology companies. ("What could I do at 39 - retire?" he said.)

One of those investments was in Scribe, LLC, an online company that had been formed to offer transcription of physician dictations. Weiss was leery about getting into the healthcare world, but he had already successfully transitioned from manufacturing to web-based business. And he'd be among friends; chief operating officer Mark Boyce had formed an investment group that included Ken Wruk, another former yesmail principal. Not only did Weiss invest, he and Boyce decided take an active role and lead the executive team.

Today, Scribe has more than 5,000 client users throughout the U.S.

With the Starting Point to to Scribe journey as a backdrop, I recently interviewed Weiss at his Kenosha home, seeking insight into his leadership approach - an approach that transcended the heady days of dot-com yesmail to today's steady, disciplined approach driving Scribe's success as a technology healthcare leader.

Below are excerpts of his thoughts on people, culture, leadership, and strategy:


• "Surround yourself with the most talented people you can, even if you may end up working for them; leaders are not intimidated by this, but most people are. You need to be able to check your ego at the door."

• "We look for team players that bring in complementary skills and experiences. Even though I led sales, I brought in a high-level sales executive with skills from taking two companies through an IPO. We brought in his experiences to fast-track the way to get there - we learned as much from his previous mistakes as his successes."

• "While not ignoring people on the team, you must spend time with the producers, not trying to micromanage underperformers to success."

• "Employees need to be on board with passion and have a purpose. A Friday afternoon team party is nice, but what gets people motivated on Monday morning? Pay can't make up for it. People need to be part of something."

• "The best way to lead people is to empower them and make them feel they are part of something bigger; if you lose that, sell the company."

• "Engender ownership by courting input from your staff. I don't tell our people what to do; I ask them what we should do."

• "A business really has two customers: its clients and its employees. If you take care of your employees, they will take care of your clients."


• "I like to challenge the status quo. When someone said to me, "We've always done it that way," I told him, "How can we say we have always done it that way, when we have only been in business for three years?"

• "You need to have some discipline and structure even in an innovative and entrepreneurial environment. When the team is made up of 'A' players, they look for weaknesses to exploit. As an example, I am very structured when having team meetings. We start at 8:00 sharp. More than once I started a meeting by myself to make the point. Meetings should always follow an agenda so they stay focused."

Leadership & strategy

• Know your business landscape. "We had to throw discipline out the window in the `90s. We had revenues, customers, profits, but others were getting the funding. In the post-crash business world, it's back to serving customers, growing the business, and making money."

• "Despite past successes, keep your learning hat on."

• "Make a lot of mistakes quickly and then don't make the same mistakes."

While the dot-com era has passed, and been documented to the point of cliché, high-growth opportunities in technology abound. Capitalizing on those opportunities and maximizing their potential requires a unique, agile leadership style.

John Weiss exemplifies the agile leader. Agile leaders anticipate market and strategic shifts. They're not just comfortable with change, they're agents of change. They quickly abandon an existing business model or practice before it gets stale to make way for new and better ideas.

Improvisation is second nature to such leaders. They can find inspiration anywhere, but look first to expose flaws in the bright light of the market, rather than further develop the idea internally.

They exude confidence, but have not crossed the line into egotism.

Those characteristics and behaviors allow them and the organizations they create to not just survive, but thrive in arenas where others stumble or fear to tread. And with perseverance and some occasional good fortune, the companies they captain receive the ultimate reward - a robust market of customers clamoring for their products and services.

Geoff Bastow is an entrepreneur, software and business architect, private equity investor and CEO of Thin Air Software. He has founded or co-founded four technology companies in Wisconsin, in both bootstrapped and venture-backed environments. He can be reached at


Sandy Swartzberg responded 8 years ago: #1

Great column. The combination of great people and a great idea cannot be beat.

Attorney Sandy Swartzberg

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