Bold leaders are not only visionary—but they also act on their visions. When a golden opportunity arises, bold leadership embraces it. Perhaps, this is why Steven Anderson, also called “Steve”, has consistently ranked on the Forbes’ Midas List for 4 straight years. The award recognizes leaders who earn the most returns for entrepreneurs and investors. Thus, with Steven Anderson investing in more than 100 companies with over 30 successful exits, he’s an obvious choice. Indeed, Steven Anderson exhibits multiple facets of bold leadership that have made him one of today’s most successful investment figures.

A caricature or cartoon of Steven Anderson holding a magic wand on one hnad and a black top hat on the other with a unicorn popping out of it
Steven Anderson’s bold leadership sought to fill the need in venture capital. He took a risk and launched Baseline Ventures as a result.

Humble Beginnings, Humble Leadership

Few would have anticipated Steven Anderson to exhibit such bold leadership during his younger years. After his father abandoned the family when he was 5 years old, Steven Anderson found his own way. He worked an array of odd jobs to help support his mother and sister. And with the help of United Way’s Big Brothers mentoring program, he achieved entrance into the University of Washington. To say the least, Steven Anderson appreciated what it took to earn an opportunity.

Despite an initial goal to become an engineer, Steven Anderson’s path to bold leadership took a different direction. After trying to convince Starbuck’s top management of a new opportunity for sales, he was granted a store manager’s position. Within a short time, Steven Anderson became the general manager for the Seattle region. He then served in various management, marketing and investment analysis positions at eBay, Microsoft, and Kleiner Perkins Caufield Byers investments.

Each opportunity provided Steven Anderson with more insight and knowledge. Undoubtedly, his interactions with such talented individuals contributed greatly to the humility he continues to show in his leadership today.

A photo quote from Steven Anderson about his beginnings in venture capital and his bold leadership as the founder of Baseline Ventures
Steven “Steve” Anderson on his bold leadership in his pursuits with Baseline Ventures

“As a seed investor, I don’t what exists until I find it…for me, it’s all about networks … I spend time with entrepreneurs, I meet them mostly through other entrepreneurs.”  – Steven Anderson

Bold Leadership Challenging the Norms

Steven Anderson eventually wanted to take a shot at a cybersecurity idea for a startup business. However, when he went to find investors, he found that the investment resources he needed weren’t there. Angel investors usually invested amounts less than $25,000. On the other hand, venture capitalists tended to invest $1 million or more. The seed money Steven Anderson needed fell between these ranges, and such investors were impossible to find.

So, like any good entrepreneur, Steven Anderson’s bold leadership sought to fill the need. He took a risk and launched Baseline Ventures as a result.

With Baseline Ventures, Steven Anderson’s main struggle was trying to find startups with good ideas before they advanced. That meant networking and making time to meet with entrepreneurs. While other venture capital firms spent time meeting and negotiating office politics, Steven Anderson was out making deals. And this facet of his bold leadership paid off well. His first major success came with Parakey, which was purchased by Facebook. This was then followed by other successes like Instagram, Heroku, ExactTarget, and GoInstant. By pursuing this lone wolf strategy, Steven Anderson’s risk paid tremendous dividends—literally.

“I find it really hard to believe that any one person will have the perfect maniacal vision right from the start …. So that’s part of my assessment, hey, does this person have an opinion, based on a worldview that they’ve developed through listening, paying attention, and pondering.” Steven Anderson

Advancing Others’ Success Through Investor Confidence

Despite Steven Anderson’s lone wolf approach to running his own venture capital firm, he is hardly solo in his efforts. In fact, Steven Anderson is quite particular in how he manages his schedule each day. He consistently makes time for his startups to help them troubleshoot and solve specific obstacles and concerns. In fact, this is exactly how the founders of Instagram decided to pursue a different application strategy. With his vast experience as well as a degree from Stanford’s School of Business, Steven Anderson has much to offer.

A collage of logos of companies working with Steven Anderson, as the founder of Baseline Capital
While other venture capital firms spent time meeting and negotiating office politics, Steven Anderson was out making deals.

In addition to empowering others in their pursuits financially, Steven Anderson also supports others through tangible confidence. Unlike many venture capitalist investors, Steven Anderson’s bold leadership provides flexibility for success. By getting to know entrepreneurs and their business ideas up front, he chooses those he thinks are more likely to succeed. In fact, the companies he has had to dismiss has been around only a quarter of those supported. This number is a highly respectful statistic for the industry—thus, awarding him the ability to show greater confidence in others.

“Generally speaking, most of my investments are pre-product launch; they’re just an idea. So, getting product-market fit is the most important goal of the round. My goal as an investor is to make sure there’s enough financing to give companies time to do that, a year to 18 months.” Steven Anderson

Strong, Bold Leadership with Strong Character

As any startup likely knows, the venture capital world can be pretty cut-throat. Not uncommonly, investors can back out and leave a company hanging. This is not Steven Anderson’s version of bold leadership. As observed by some of his startups, getting Steven Anderson to say something bad about another person is highly improbable. Instead, he chooses to take the high road.

Also, forget about Steven Anderson having an ego. Not only does he expect to lose on occasion, but he also has no dream of Baseline Ventures becoming an institution.

For Steven Anderson, his dream is to simply provide people with great ideas a chance to excel. By filling a notable gap in venture capital funding, he offers hope to many startups that might otherwise never see success. In doing so, his bold leadership contributes to society’s progress one startup at a time.  Likewise, while Steven Anderson may be the man with the golden touch, his bold leadership offers immensely more. This is the power that Steven Anderson gives each entrepreneur who has the pleasure to work with him.

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