Inside Guideline's mission to modernize 401(k)s | Building from first principles, finding strategic edges, and rewiring retirement | Kevin Busque (Co-founder and CEO)

Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures. After launching Guideline to address those problems head-on, the company has seen remarkable growth, hitting $120 million in ARR by June 2024. In this conversation, Kevin shares pivotal moments that shaped Guideline’s trajectory, including a strategic partnership with Gusto. He also explains how his “Do the hard thing first” mindset helped the team build an industry-leading platform and disrupt an entrenched market. – Referenced: ADP: https://www.adp.com/ Aydin Senkut: https://www.linkedin.com/in/aydins/ CalSavers: https://www.calsavers.com/ DoorDash: https://www.doordash.com/ Fidelity: https://www.fidelity.com/ Guideline: https://www.guideline.com/ Gusto: https://gusto.com/ Intuit: https://www.intuit.com/ Jeremy Caballero: https://www.linkedin.com/in/jeremycaballero/ John Zimmer: https://www.linkedin.com/in/johnzimmer11/ Josh Reeves: https://www.linkedin.com/in/joshuareeves/ Mike Nelson: https://www.linkedin.com/in/mnelsonio/ Leah Solivan: https://www.linkedin.com/in/leahsolivan/ Paychex: https://www.paychex.com/ Plaid: https://plaid.com/ Taskrabbit: https://www.taskrabbit.com/ Tomer London: https://www.linkedin.com/in/tomerlondon/ – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevinbusque/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Teaser: “I don’t believe in stealth mode” (02:51) Inspiration behind Guideline (07:56) Lessons from a year’s research before Guideline (10:44) Identifying market pull for Guideline (14:28) What Kevin learnt before shipping their first product (19:10) How Guideline set their fees up (27:51) The surprising range of Guideline’s early customers (31:48) Kevin’s insights from the Gusto integration (39:48) Guideline’s first year (44:44) Working with Plaid as Guideline’s first customer (53:28) Guideline’s auto-enrollment feature (57:53) Lucky 8: Kevin’s unexpected pricing strategy (62:04) Franchise opportunities (64:49) Kevin’s reflections on Taskrabbit (71:36) Will Guideline ever go multi-product? (72:37) Kevin’s take on product-market fit (73:30) Guideline’s compounding advantage (78:51) The challenges faced by introverted leaders