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.

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Referenced:

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Where to find Kevin:

LinkedIn: https://www.linkedin.com/in/kevinbusque/

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Where to find Brett:

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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

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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

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