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Startup Ignition Podcast

Startup Ignition Podcast

By: John & Tyler Richards
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 Father and son team John and Tyler Richards — veteran entrepreneurs, venture investors, mentors, and educators — discuss all things entrepreneurship and venture capital.Startup Ignition Academy, Inc. Economics Leadership Management Management & Leadership
Episodes
  • Dan Caffee: Sold Teem to WeWork for $100M, Startup Mistakes, Personal Family Tragedy

    Dan Caffee: Sold Teem to WeWork for $100M, Startup Mistakes, Personal Family Tragedy
    Feb 12 2026
    In this episode of the Startup Ignition Podcast, Tyler and John sit down with Dan Caffee, a veteran entrepreneur, investor, and the current CEO of Voiso. Dan shares his incredible journey through the Utah tech scene, from his early days bootstrapping companies to the massive success of Teem, a conference room scheduling platform he sold to WeWork for over $100 million in an all-cash deal. Beyond the business wins, Dan challenges the "startup as a baby" mentality, discusses the importance of solving problems for industrial sectors rather than just other "tech bros," and opens up in a deeply moving segment about the tragic loss of his wife, Elise, offering profound insights on grief, resilience, and the vital importance of living life without delay.


    (00:00:00) Teaser: Selling to WeWork and the reality of loss

    (00:02:06) Introduction to Dan Caffey: The Swiss Army Knife of startups

    (00:05:14) Founder’s Firsts: The worst pitch that still got funded

    (00:08:22) The first "Oh Crap" moment: Layoffs and near-bankruptcy

    (00:10:24) Validation: Discovering Twitter was using their side project

    (00:13:33) Learning the hard lesson of firing a friend too late

    (00:23:09) Dan’s origin story: From industrial recycling to tech

    (00:29:01) Driver Careers and the pivot to Neutron Interactive

    (00:35:44) The birth of Teem: Turning a skunkworks project into a company

    (00:37:46) The Entice Labs story: Failure, acquisition, and meeting John

    (00:47:42) The Entrepreneur’s Dilemma: Why your company is not your baby

    (00:52:51) Handing over the CEO reins to co-founder Sean Ritchie

    (00:57:12) Monetization strategies: From free downloads to SaaS

    (01:00:27) The Exit: Selling Teem to WeWork for $100M all cash

    (01:06:42) Starting Voiso: Why tech ignores the industrial sector

    (01:14:59) Addressing tragedy: The accident in Mexico and losing Elise

    (01:19:05) The most important lesson: "Don't wait" to live your life

    (01:23:25) Choosing resilience: Taking the family trip to Egypt

    (01:29:49) Dan’s final advice: It always comes down to the people

    Learn more about us:
    https://startupignition.com/links

    Apply to be a guest on the pod:
    https://startup-ignition-podcast.paperform.co/

    Follow John & Tyler:
    https://x.com/trich_
    https://www.linkedin.com/in/johnrichards/

    Subscribe on YouTube:
    https://www.youtube.com/@StartupIgnition

    Follow on X:
    https://x.com/startupignition

    Follow on Instagram:
    https://www.instagram.com/startupignition/

    Follow on TikTok:
    https://www.tiktok.com/@startupignition

    Follow on LinkedIn:
    https://www.linkedin.com/school/6458758/admin/dashboard/

    Follow on Facebook:
    https://www.facebook.com/startupignition/

    #StartupIgnition
    #DanCaffey
    #Teem
    #WeWorkExit
    #Entrepreneurship
    #Voiso
    #IndustrialTech
    #GriefAndResilience
    #StartupFunding
    #Bootstrapping
    #TechFounders
    #BusinessStrategy
    #UtahTech
    #Leadership
    #AngelInvesting
    #FounderAdvice
    #MentalHealth
    #FamilyFirst
    #SaaS
    #ExitStrategy
    Show More Show Less
    1 hr and 32 mins
  • Sam Stoddard: TurboTax for Immigration, YC, VC, Exits

    Sam Stoddard: TurboTax for Immigration, YC, VC, Exits
    Feb 5 2026
    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

    Learn more about us:
    https://startupignition.com/links

    Apply to be a guest on the pod:
    https://startup-ignition-podcast.paperform.co/

    Follow John & Tyler:
    https://x.com/trich_
    https://www.linkedin.com/in/johnrichards/

    Subscribe on YouTube:
    https://www.youtube.com/@StartupIgnition

    Follow on X:
    https://x.com/startupignition

    Follow on Instagram:
    https://www.instagram.com/startupignition/

    Follow on TikTok:
    https://www.tiktok.com/@startupignition

    Follow on LinkedIn:
    https://www.linkedin.com/school/6458758/admin/dashboard/

    Follow on Facebook:
    https://www.facebook.com/startupignition/

    #SimpleCitizen
    #ImmigrationTech
    #YCombinator
    #StartupJourney
    #VentureCapital
    #StudentEntrepreneur
    #BYU
    #LegalTech
    #ExitStrategy
    #FounderStories
    #SiliconSlopes
    #BusinessAcquisition
    #RevenueGrowth
    #Fragomen
    #TechStartup
    #Entrepreneurship
    #StartupAdvice
    #ProductMarketFit
    #AngelInvesting
    #StartupIgnition
    Show More Show Less
    1 hr and 26 mins
  • Matt Stapleton: Turning Excel Sheets into $480M, SaaS Ideas, Strategy, Startups

    Matt Stapleton: Turning Excel Sheets into $480M, SaaS Ideas, Strategy, Startups
    Jan 29 2026
    In this episode of the Startup Ignition Podcast, we sit down with Matt Stapleton, a multi-time founder who recently exited Spiff to Salesforce for nearly $480 million. Matt shares his journey from "dialing for dollars" as a commission-only rep to building and exiting two successful FinTech companies: Capshare and Spiff. We dive deep into the importance of clean cap tables (including a horror story about 16 classes of preferred stock), why the best SaaS ideas are often hidden in manual Excel spreadsheets, and the strategic nuance of taking investment from corporate venture arms. Matt closes the episode with his "2% rule" for productivity that helped him navigate the path from idea to nine-figure exit.


    (00:00:00) Introduction and Matt Stapleton’s bio

    (00:04:35) Icebreaker: The real reason founders love AI

    (00:07:51) Horror Story: The cap table with 16 classes of preferred stock

    (00:12:10) Why bad cap table management is securities fraud

    (00:16:23) The key to getting acquired: Beginning with the end in mind

    (00:19:00) Matt’s background: From finance major to cold calling

    (00:30:17) How "dialing for dollars" changed Matt’s career trajectory

    (00:34:50) Founding Capshare and competing with Carta

    (00:46:17) The first exit: Selling Capshare to Solium/Morgan Stanley

    (00:51:28) The genesis of Spiff: Replacing spreadsheets with SaaS

    (00:56:48) Why public companies still run critical processes on Excel

    (01:01:20) Public vs. Private exits: Valuation multiples and liquidity

    (01:05:43) Strategy: Taking investment from Salesforce before the acquisition

    (01:08:50) Final Tip: The "2% Rule" and doing the hard things

    Learn more about us:
    https://startupignition.com/links

    Apply to be a guest on the pod:
    https://startup-ignition-podcast.paperform.co/

    Follow John & Tyler:
    https://x.com/trich_
    https://www.linkedin.com/in/johnrichards/

    Subscribe on YouTube:
    https://www.youtube.com/@StartupIgnition

    Follow on X:
    https://x.com/startupignition

    Follow on Instagram:
    https://www.instagram.com/startupignition/

    Follow on TikTok:
    https://www.tiktok.com/@startupignition

    Follow on LinkedIn:
    https://www.linkedin.com/school/6458758/admin/dashboard/

    Follow on Facebook:
    https://www.facebook.com/startupignition/

    #SaaS
    #FinTech
    #StartupExit
    #Salesforce
    #Spiff
    #CapTable
    #Entrepreneurship
    #VentureCapital
    #Founders
    #BusinessPodcast
    #ExitStrategy
    #StartupAdvice
    #CorporateDev
    #SalesCommission
    #TechStartups
    #AngelInvesting
    #StartupIgnition
    #UtahTech
    #BootstrapToExit
    #SaaSFounders
    Show More Show Less
    1 hr and 12 mins
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