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Sam Stoddard: TurboTax for Immigration, YC, VC, Exits

Sam Stoddard: TurboTax for Immigration, YC, VC, Exits

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 In this episode of the Startup Ignition Podcast, we sit down with Sam Stoddard, the co-founder and CEO of Simple Citizen—a platform often described as "TurboTax for immigration." Sam shares his journey from an accounting student at BYU to navigating the complex US immigration system for his wife, which sparked the idea for his startup. We dive into his unique path of raising venture capital before joining Y Combinator, the crisis that almost sank the company during their YC batch, and the eventual acquisition of Simple Citizen by the world's largest immigration law firm.


(00:00:00) Introduction and the power of student entrepreneurship

(00:04:07) Sam Stoddard’s bio: Building the "TurboTax for immigration"

(00:07:32) Icebreaker: Equity vs. salary and night owls vs. early birds

(00:12:12) Debating the leadership styles of Elon Musk, Jeff Bezos, and Bill Gates

(00:21:42) Growing up in Portland as the youngest of eight adopted siblings

(00:28:37) Lessons learned serving a mission in Seoul, South Korea

(00:35:45) Interning at Money Desktop (MX) under Ryan Caldwell

(00:40:05) The "Lightbulb Moment": Navigating the green card process

(00:46:27) The $500 lawyer meeting that validated the business idea

(00:49:42) Winning $250k in non-dilutive capital through startup competitions

(00:53:20) Building the MVP and finding a technical co-founder

(00:56:03) Finding the first customer and the viral loop of immigration

(00:59:55) Pricing mistakes: Charging $250 vs. thousands for a lawyer

(01:01:53) Applying to Y Combinator after already raising a seed round

(01:06:52) The immense value of the YC alumni network

(01:08:47) Managing valuation conflicts between VCs and Y Combinator

(01:11:00) Moving to Mountain View and ignoring investors to focus on product

(01:14:18) How a Google Ads ban almost killed the company—and the angel who saved it

(01:18:05) Pivoting from B2C to B2B and winning enterprise contracts

(01:20:00) The acquisition by Fragomen and the decision to sell

(01:23:04) Sam’s #1 piece of advice: Revenue is the only thing that makes it real

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#SimpleCitizen
#ImmigrationTech
#YCombinator
#StartupJourney
#VentureCapital
#StudentEntrepreneur
#BYU
#LegalTech
#ExitStrategy
#FounderStories
#SiliconSlopes
#BusinessAcquisition
#RevenueGrowth
#Fragomen
#TechStartup
#Entrepreneurship
#StartupAdvice
#ProductMarketFit
#AngelInvesting
#StartupIgnition
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