On Tour with Steve Case


Supporting entrepreneurs with capital outside of Silicon Valley, NYC and Boston, Steve Case brought his “Rise of the Rest” tour to Florida and Puerto Rico.  We hosted him in Orlando and I was with him in Puerto Rico.

Steve Case, founder of AOL, took his 8th “Rise of the Rest” Tour to Florida and Puerto Rico, engaging 3,500 business, civic and political leaders towards his vision of increasing investment in startups across America. His motivation is the reality that 75% of venture capital is invested in California, New York and Massachusetts; leaving 25% for the rest of the country. Imagine if capital found twice as many investments outside the “big 3” VC markets- think jobs, wealth creation and growing economies. Towards this end, Mr. Case has secured additional investment from many of America’s most successful entrepreneurs and he has built a dynamic team to “do their part” and bring capital and a spotlight to cities across the U.S.

In joining this tour for 2 stops (as a co-host in Orlando and as a guest in San Juan, PR) I observed 5 salient lessons worth sharing.

1. “There is no future in rebuilding the past.” A message for us all from the Foundation for Puerto Rico, an organization that has been central to the Hurricane Maria response and recovery effort. In many cases, a devastating crisis brings many opportunities and they have adopted this mantra, which I fully embrace. Annie Mayol Del Valle, their president and ceo, shared that an employee of the foundation came up with the mantra in the middle of a strategy session immediately after the category 4 hurricane devastated the island.

2. Idea + People + Execution wrapped in a compelling story = success. Mr. Case brings such clarity to startups and is so engaged in each of their stories. Listening to him give advice, this formula is an embodiment to the saying “simplicity is the ultimate sophistication.”

3. The “Rise of the Rest” is our best economic strategy. Economic data suggests that scaling startups create the net new jobs in America. Large companies grow and shrink (i.e. Amazon grows and Sears enters bankruptcy), creating a stable base of jobs. On the other end of the spectrum, small businesses account for a lot of jobs, but go in and out of business, also accounting for consistency instead of net growth. As a country, if we can create a boomerang effect, where talent and capital finds it way out of the “big 3 VC markets” and back into cities across America, we can all rise together.

4. The “third wave” requires startups to develop partnerships to thrive. As Mr. Case describes in his book, the first wave was building the tech software, hardware and systems. The second wave, was building apps and tools based on this new infrastructure. And, the third wave is an entirely new set of ideas that leverage artificial intelligence, VR/AR, machine learning and the internet of everything. To accomplish success in the “third wave,” companies need to be good at building partnerships to establish sales channels, work with government and engage other businesses to bring products and services to the market. Nearly every company we saw on tour was an example of this.

5. Make sure to tell your story. In a crowded market, to people with short attention spans, resonating with an authentic and compelling story will separate the truly successful startups. Throughout the day, the play “Hamilton” became a relatable theme, and particularly the message of telling your story. We traveled with Jose Andres, who has also had an incredible impact on the island and is appropriately revered for his unlimited passion for helping the people of Puerto Rico. Ideally, Miranda, Andres and Case can inspire confidence that Puerto Rico can also “rise.”

Maybe you were also on tour or have read Mr. Case’s book, The Third Wave. I’d love to hear what really resonated with you.