Being Contrarian is the Fun Part: Interview with Early-Stage Venture Investor and Co-Founder of Gutter Capital, James Gettinger

Being Contrarian is the Fun Part: Interview with Early-Stage Venture Investor and Co-Founder of Gutter Capital, James Gettinger

Daily Fantasy Sports, or DFS for short, is an accelerated version of traditional fantasy sports where participants draft a roster of real-world athletes and compete against other players based on those athletes’ actual statistical performance in games. Unlike season-long leagues, DFS contests typically last just a single day or a single week. Needless to say, the odds are not in your favor. By most estimates, only a small fraction of DFS players, somewhere in the low single digits, are consistent, long-term winners. Early-stage venture investor and co-founder of Gutter Capital [https://www.guttercapital.com], James Gettinger, belongs to that rarefied air. James ran a profitable business in professional poker and later DFS for nearly a decade. A few of his career highlights include winning the DraftKings World Fantasy Football Championship in 2017 and finishing as runner-up at the DraftKings World Fantasy Basketball Championship in 2019. Professional players like James work tirelessly to create an edge, the term for a mathematical advantage you hold over the bookmaker or your competitors. Having an edge means the true probability of your bet winning is higher than the implied probability suggested by the odds or the betting line. Make no mistake, it takes a lot more than luck to do that sustainably. James developed proprietary software programs, engaged in advanced analytical modeling, and spent countless hours studying and learning to manage his own psychology to successfully beat the odds. James would go on to invest his winnings into a series of angel investments with his partner, Dan Teran, the founder of Managed by Q, which was acquired by WeWork in 2019. Eventually, the two used their track record to start the New York-based early-stage venture firm Gutter Capital [https://www.gutter.cc/] in 2021. Five years later, they’ve raised three funds and pioneered an innovative accelerator model called Elbow Grease [https://www.elbowgrease.gutter.cc/], where Dan and James look to partner with founders from their very earliest days across a multi-decade journey. On their website Dan and James write, “We built Gutter Capital to back exceptional founders tackling the world’s toughest problems. We focus on issues of affordability, economic mobility, and sustainability, the ones that if we do not solve now, we are sunk.” This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit 90percentmental.substack.com [https://90percentmental.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Ignore the Noise. One Shot at a Time: Interview with Deep Value Investor John Davenport

When you think about investing, you probably think about picking stocks, conducting diligence, and running financial analysis. What’s less obvious is the heavy mental and emotional component that investing requires. Today I’m excited to dive deeper into the psychology of investing with public markets-focused, deep value and event-driven investor John Davenport. John is the founder of Davenport Fund Management, a boutique investment partnership that invests his own money alongside a select group of limited partners. As a deep value investor, John looks for stocks that are temporarily out of favor and trading at a substantial discount relative to their intrinsic value, meaning companies whose assets or cash flow are worth substantially more than the market currently says they’re worth. That gap is what protects the downside. The upside comes from pairing that discount with an event-driven catalyst: meaning some change that will force the market to care, thereby generating an increase in the stock price. It all sounds pretty good, but as John knows executing on the strategy is anything but simple. What he would tell you is that the hardest part isn’t necessarily finding the opportunities, it’s staying in them, and holding stocks that may be out of favor for months, even years, while simultaneously resisting the urge to invest in the hot parts of the market that keep climbing. Warren Buffett’s late partner the investor Charlie Munger once put it this way: “If you can’t stomach 50% declines in your investment, you will get the mediocre returns you deserve.” So yeah, easier said than done. Over the course of our conversation, John and I spoke about: * What deep value investing actually means, and why today’s market, dominated by indexation and the AI trade, has made it both a brutal and an opportunity-rich environment * How John has learned to manage the psychological side of deep value investing * Why it’s important to get away from your desk * Learning to trust gut feel as unconscious pattern recognition and the cost of ignoring it * The mental models he’s carried from competitive golf into the markets This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit 90percentmental.substack.com [https://90percentmental.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

"I Know How the Story Ends:" Interview with Paytient Founder & CEO, Brian Whorley

For over a decade, Brian Whorley worked at a non-profit, community-owned 400-bed hospital in Columbia, Missouri and loved every minute. In reflecting on his time there and the needs he witnessed within our healthcare system, Brian says, “I felt a great deal of pride being a very small part of a place full of really talented, mission-driven people who provided great care during life’s most uncertain moments. The challenge is to satisfy a near infinite need with finite resources — how our country figures that out is consequential.” Fortunately, lightning struck one afternoon as Brian rode his bike along the Missouri River. He returned home with the idea to help expand access and affordability at lower cost; an idea that would lead to the founding of Paytient [https://www.paytient.com/]. The company was first to market with a triple-sided product, the Paytient app, that 1) allows employers to pay less for lower cost health plans, 2) enables employees to more easily pay for care at time of service (without interest or fees), and 3) help providers to cure uncompensated care and receive payment in full at the time of service. Since founding the company in 2018, he has been walking toward a single North Star: not just helping people pay for care but to help people & health plans pay less for that care. Today, Paytient works with nearly six thousand employers, insurers, and providers, serves over 26 million members, and has raised more than a hundred million dollars in capital. What drew me to this conversation wasn’t the scale of what Brian has built — it was how he thinks about building it. We got into what it means to operate from a place of deep conviction when most of the world can’t see what you see yet, how Brian feeds his soul and his spirituality so he can show up as his best self, the tension of transitioning from founder to CEO, how he’s learning to release control, and why he believes the worry-driven voices in our heads are almost never the ones worth listening to. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit 90percentmental.substack.com [https://90percentmental.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Intensity is the Strategy: Interview with GreenPal CEO, Bryan Clayton

Bryan Clayton spent years building one of the largest landscaping companies in the state of Tennessee. He grew Peachtree from a small operation into a company with over 150 employees and 8 figures in annual revenue before selling the business in 2013. While he initially thought he'd take time off, Bryan found himself drawn back to operating. Only this time he didn't start in an industry he already knew. Instead, he became a tech entrepreneur and started GreenPal [https://www.yourgreenpal.com/], a platform that connects homeowners with local lawn care professionals, with two of his best friends. The journey was anything but easy. He and his cofounders ended up having to rebuild the first product from scratch while simultaneously teaching themselves to code. It would take three years to expand beyond Nashville into a second market. Today, over 10 years later, GreenPal is a nationwide platform that has celebrated over 5 million transactions. Over the course of our conversation, Bryan and I spoke about what he’s learned across his 20+ year entrepreneurial journey. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit 90percentmental.substack.com [https://90percentmental.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

What You Focus on is What You Feel: Interview with Former Professional Athlete, Entrepreneur, and Beam Cofounder, Matt Lombardi

Matt Lombardi played college hockey at Boston College before going on to play professionally for two years before injuries forced him into an early retirement. As he navigated life after sport, Matt searched for something that would challenge him mentally the way competitive sports had challenged him physically. He found his answer in entrepreneurship. In 2018, Matt started Beam [https://shopbeam.com/] with another former BC athlete and former professional baseball player, Kevin Moran. Their mission was to create a brand with science-backed wellness products that enabled their customers to feel and perform at their best. Eight years later, Beam has grown to a team of over 30 and expanded that mission into product categories that include sleep, hormone balance, gut health, creatine, and pediatrician-formulated supplements for growing kids. Over the course of our conversation, Matt and I spoke about * Why one of the best things leaders can do is ask questions * The role of quirky sayings in creating Beam’s culture of debate * Why he’s focusing on learning to calm himself down rather than amp himself up * The role of process and execution in avoiding worrying too much about the competition * Why Matt believes that the philosophy behind the saying “what you focus on is what you feel” is so foundational to creating strong mental performance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit 90percentmental.substack.com [https://90percentmental.substack.com?utm_medium=podcast&utm_campaign=CTA_1]