Advice Line with Leah Solivan of Taskrabbit (September 2024)

TaskRabbit founder Leah Solivan joins Guy Raz on the HIBT Advice Line to help three founders with real growth challenges. Kate Pitner built Poppy Notes during the pandemic, turning her greeting card designs into a polished iOS app, but she struggles to be discovered in a crowded App Store. Sean Sarekli and his wife created My Love Your Love, a couples coaching app that teaches relationship skills before problems escalate, yet their biggest hurdle is acquiring pairs of committed users. Allan Ward developed Dynabuddy, a streaming platform where dinosaur characters teach kids band instruments, and he needs help recruiting early adopters who will stick with the curriculum. Leah draws on her experience building a two-sided marketplace to offer practical advice on trust, storytelling, and finding the right first customers.

Kate Pitner: Poppy Notes Visibility

Kate's app is well-designed, but App Store discoverability and Instagram noise are drowning her out. Leah recognizes the problem because TaskRabbit once faced the same trust-building gap. She advises Kate to lean into her 20-year design pedigree and the personal origin story behind Poppy Notes, because people connect with founders, not just features. Instead of chasing broad social media reach, Leah recommends targeting micro-communities—parents, event planners, nonprofit partners—where intentional communication already matters, and turning those early users into evangelists.

Sean Sarekli: My Love Your Love Couples Acquisition

Sean's app requires both partners to commit, which makes growth twice as hard. Leah reframes the constraint as an asset: shared commitment is the product's selling point, not its weakness. She suggests positioning My Love Your Love as a proactive relationship tool rather than a therapy replacement, and courting therapists and relationship educators as referral channels who can introduce couples in pairs. By embedding in professional networks, the Sareklis can acquire users in the natural unit they already operate in—couples.

Allan Ward: Dynabuddy Early Adopters

Dynabuddy's Trojan-horse concept—kids think they're watching fun dinosaur videos but are actually learning music—needs a gateway audience. Leah advises Allan to partner directly with music teachers and school districts, because educators are trusted gatekeepers who can introduce the platform to entire classrooms. She also suggests leaning into the social-impact angle in marketing, since parents and grandparents are more likely to try a service that donates access to Title 1 schools. The combination of curriculum rigor, character-driven engagement, and a clear mission gives Dynabuddy a differentiated story that will resonate once the right early-access channels are opened.

Final Thought

Whether it's greeting cards, couples coaching, or dinosaur music teachers, Leah's advice is consistent: early growth is less about hacking algorithms and more about finding the people who already believe in what you're building. The founders who win are the ones who tell a story that makes someone feel seen.