What happens when business success collides with the demands of family life? Rob Long, the serial entrepreneur behind River City Roll, Bar West, and the Surf dating app, doesn't hold back in this refreshingly candid conversation about the real costs of building multiple successful ventures.
Rob shares the moment his heart broke when his four-year-old daughter said, "Daddy, I don't want you to go to practice" as he left to coach lacrosse – a passion project that rejuvenates him mentally but comes with personal sacrifice. This tension between professional drive and family connection becomes a throughline in our discussion, offering a window into the constant trade-offs entrepreneurs navigate daily.
The conversation takes a fascinating turn when Rob reveals how golf has become both his personal therapy and secret business weapon. "I've raised a lot of money on golf courses," he explains, describing how the sport creates rare opportunities for authentic connection in our hyper-connected yet increasingly isolated business world. His advice to young entrepreneurs? "Pick up golf – it's a cheat code." He shares stories of CEOs who wouldn't give him 30 minutes by phone but eagerly accepted invitations to play a round, giving him five uninterrupted hours of their time.
Perhaps most thought-provoking is Rob's intentional approach to social media and personal branding. Unlike many entrepreneurs who build personal platforms alongside their businesses, he maintains a deliberately low profile online. "The internet is a mean place," he reflects, sharing a telling story about how he once publicly invited online critics to meet him in person to discuss their concerns – and not a single person showed up.
Whether you're building a business, raising a family, or simply trying to find balance in a chaotic world, Rob's perspective offers valuable insight on defining success on your own terms and remembering what truly matters beyond the balance sheet.
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