A version of this article previously appeared Forbes. Long before author Stephen King sold over 350 million books, he was a budding entrepreneur. In order to pay his college tuition, young Stephen created a sole proprietor startup with a very entrepreneurial pricing structure. Leveraging his core competency, Stephen cranked out term papers for his fellow students. Papers that resulted in an “A” grade earned him $20, “B” papers cost his customers $10. There was no charge for “C” level papers. The most enterprising aspect of King’s business model was his promise to pay his customers $20 for any paper that didn’t earn at least a C grade. According to King, “I made sure I would never have to pay, because I couldn’t afford it.”
A version of this article previously appeared in Forbes. It was a decade ago that I led the sale of Expertcity (creator of GoToMeeting) to Citrix. During the early 2000’s, my team grew the company to one of the largest SaaS businesses of its day, with sales of $70 million. In November of 2015, Citrix announced that it will spin out the “GoTo” Division, of which GoToMeeting remains the flagship product, as a standalone public company. At approximately $600 million in recurring, annual revenue, the new GoTo Company will rank as one of the largest pure SaaS companies on the planet.
A version of this article previously appeared Forbes. One of the reasons I know way more about online sales taxes than I ever thought I would is due to Rincon Venture Partners’ investment in TaxJar, one of the leaders in this emerging space. Taxes may not be fun, but I am proud to be affiliated with a company that takes much of the pain out of the process. January is coming up and you know what that means. Did you immediately think “a relaxing post-Q4 break?” Hopefully you’ll get plenty of rest during the Holidays because soon after the New Year starts, online retailers must begin contemplating sales tax deadlines.
A version of this article previously appeared Forbes. When I learned that one of my former UC Santa Barbara students scored a $1 million investment from the Shark Tank judges, I reached out to see what insights he might be able to share with his fellow entrepreneurs. Whether you love or loath the show, his responses might surprise you. Jeff Overall, Founder and CEO of PolarPro, was successful because he properly balanced the show’s need to entertain its audience, while delivering a professional pitch of his solid business. The entertainment factor was his exaggerated, surfer bro delivery which charmed the judges, but didn’t distract them from the underlying fundamentals of the business. I recently caught up with Jeff and he candidly shared his thoughts regarding his Shark Tank experience and whether or not he felt the return on his efforts were worthwhile. You can check out his Shark Tank pitch HERE (go to the last segment of the video and be ready to watch an annoying onslaught of commercials).
Photo courtesy of Santa Barbara Independent’s recent Techtopia Issue A version of this article previously appeared in Forbes. Serial entrepreneurs agree that it is best to communicate with investors on an eighth grade level. To illustrate this point, former DoubleClick Founder and current CEO of Graphiq Kevin O’Connor often begins his talks to entrepreneurial students by asking the following question. Select the real software product from this list. A. Assimilated, zero-administration, standard database-queuing schema B. Open-architected, workforce-neutral, productivity assimilator C. Modularly reduced Graphical User Interface heuristic D. Profit-focused, fault-tolerant encoding interface
A version of this article previously appeared in Forbes. Who makes more money, entrepreneurs or venture capitalists? I recently came across an interesting Quora response from a friend and one of my favorite co-investors, Jason Lemkin.
A version of this article previously appeared on Forbes. There are a number of reasons why Rincon Venture Partners passed on Twilio’s Seed Round. In retrospect, our decision was both perfectly rational and completely lame. VC's love to talk about their successes. However, they seldom acknowledge their mistakes. Exceptions exist, such as the highly self-aware Paige Craig, who recently described how he missed out becoming Airbnb's first investor. Yet most VC's bury their failures under six feet of denial. Twilio has now raised around $235 million, including a July 2015 round totaling $130 million. This latest round valued the company in excess of a billion dollars, entering them into the overly-hyped Unicorn Club.
Brian Epstein, the Beatles’ Manager, was tenacious and ambitious, but he was musically inept. Brian was instrumental in establishing the Beatles’ career, but he had no input on the band’s production of music. In the same way, investors can be immensely additive to an entrepreneur’s journey, as long as they know the limits of their ability to help. Effective startup investors guide management’s decision process, but ultimately they support the team’s decisions. If the investors repeatedly disagree with management, they should either disavow themselves from the startup (which is typically difficult for a venture capital firm to do) or make appropriate replacements to the management team. However, they should never attempt to run a company from the sidelines.
A version of this article previously appeared on the Wall Street Journal. As crazy as it sounds, surfing has made me a better investor. The sport involves a surprising amount of downtime between sets. During the many hours I have stood in anticipation of the next wave (as noted in You’re Never To Old To Learn To Surf, I’m an old guy on a standup paddle board), I have come to realize that surfing and investing share a number of surprising corollaries.
A version of this article previously appeared in Forbes. On a micro level, you can do your part to fix tech's gender problem by recruiting people with diverse backgrounds and place them in a company culture that rewards those who challenge the status quo. Like all important social movements, the change begins with you.