Host Tiffany Rosenbaum sits down with Stephen Fox, the founder of Upkeep Media, a remote-first marketing agency that grew from a one-man operation into an industry quiet giant serving some of the biggest names in property management—all while Stephen intentionally keeps the company lean, profitable, and 100% bootstrapped. In a warm and unguarded conversation, Stephen traces his path from burnout in corporate real estate to betting everything on content, community, and relationships over paid ads and aggressive scaling.
He opens up about designing a business that gives him time for family and adventure instead of endless hustle, why he still answers customer support tickets himself, the counterintuitive growth strategies that doubled revenue without doubling headcount, and how saying "no" more often than "yes" became his greatest competitive advantage. If you've ever wanted to build something successful that doesn't slowly destroy the rest of your life, Stephen's story is proof that slower, smaller, and more intentional can quietly outperform the loud race everyone else is running.
Connect with Tiffany on Instagram at @TiffanyMRosenbaum to share your thoughts on this empowering discussion!
