UVF-C Venture Profile: an Interview with Todd Benson

By Jake Conklin, University Venture Fund-Crossroad, Intern

What did you think you would do when you were in college?

At the University of Kansas, Todd majored in business administration and accounting, aspiring to attend law school after graduation. In his coursework, he found himself fascinated with finance and marketing classes, which look at the bigger picture rather than specific legal details. While exploring potential careers in law, Todd realized that he was much more passionate about the high-level strategic side of business. So he decided to pursue a Master of Business Administration, which he completed at Harvard University in 1991.

What brought you to venture or entrepreneurship?

Todd began his career in finance, working in Fixed Income Capital Markets at Salomon Brothers, an experience that he described was vaguely similar to that described in Michael Lewis’ book “Liar’s Poker.” After attending Harvard for his MBA, he returned to Salomon Brothers, working in investment banking across media and communications. He and a colleague convinced Salomon to restart a private equity business, co investing in leveraged buyouts and forming a mezzanine debt business.

After Citigroup was forced to divest non-core businesses post the Global Financial Crisis and Citigroup Private Equity was sold to StepStone, Todd began his “third act” professionally, forming Herington LLC (named after the small town in Kansas where he was born) where he began investing, advising and serving on boards. The first company where he got involved was L2 which benchmarked the digital competence of brands which had been founded by Professor Scott Galloway who has gone on to develop some renown as an author and podcaster. Reflecting on key lessons, Todd emphasized the importance of cultivating “serendipity” and putting yourself in positions to succeed by working with talented people.

Who was instrumental or inspiring to you at the beginning of your entrepreneurial journey?

Looking for his “third act” later in his career, Todd was invited by Scott Galloway, an accomplished entrepreneur who he had met via board service during his time at Citi, to join the board of L2. Galloway’s intellect, leadership skills, generosity and entertaining personality led Benson to join the company. Scott is a professor at NYU, New York Times Best Seller, and is the host of “The Prof G Pod” along with co-host of “Pivot” with Kara Swisher.

What is the most significant or challenging thing you manage in your business daily?

Todd believes that success in business more often than not comes down to people issues and the ability to communicate effectively. After honing these skills early in his career, he later focused on learning to ask the right questions to deeply understand both problems and opportunities. He often thinks about second-order impacts — for example, the significant demand for Nvidia chips due to the rise in AI or the effect on the startup ecosystem from rising interest rates. Now, Todd has the challenge of competing in an ever-changing Venture Capital industry.

Do you have any advice for a new entrepreneur or for someone who aspires to be in venture?

Todd believes that more important than one’s network, is their reputation. Building a reputation as someone who adds value to others, and keeping that reputation, is extremely important. Be a consistent net exporter of intellectual insights, favors for others, and positive energy — and it can pay dividends down the line. Always know what the world sees in you by answering the simple question; “why does my phone ring?” For students who inspire to be in venture, Todd says the math of why you should invest in a company should be able to be done on a napkin.

Todd emphasizes the importance of learning how to think, articulate communication, strong reasoning, and choosing your friends aspirationally.

What books, podcasts, or blogs do you recommend people interested in entrepreneurship or venture capital listen to or read and/or what do you regularly tune into?

Todd recommends Michael Porter’s “Porter’s Five Forces,” for its strategic decision making framework. He also suggests Michael Lewis’ “Liar’s Poker” for an entertaining insight into the “wolves that raised him” along with Morgan Housel’s “The Psychology of Money” and “Same as Ever.” For podcasts, he points to “Invest Like the Best” with Patrick O’Shaughnessy, “Freakonomics Radio” with Stephen Dubner and “The Prof G Pod” with Scott Galloway.