In this brutally honest and deeply heartfelt episode of Rise to Run, host Alan welcomes longtime friend David Oltman for a no-holds-barred conversation about life’s highs, lows, and everything in between. David shares his journey growing up on a Minnesota hobby farm, facing a tough childhood, and learning financial survival skills at an early age. From flipping hay bales to losing jobs during the 2008 recession, his path wasn’t easy—but it was real. David opens up about losing some of the closest people in his life, including his brother, best friend, and mentor, and how those experiences shaped his perspective and purpose. Through laughter, military banter, and painful memories, he walks us through how those dark moments helped him build his own insurance agency and a life of meaning. The conversation dives deep into grief, grit, fatherhood, and the responsibility of being a leader both at home and in business. Whether you’re in a tough season or on the verge of a breakthrough, this episode is for you. David’s story is proof that it’s okay to not have it all figured out—just don’t stop moving forward. Press play. Because someone’s story might just be the thing that changes yours.