Startup Ignition Podcast

John & Tyler Richards
  • 5.0 (10)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Father and son team John and Tyler Richards — veteran entrepreneurs, venture investors, mentors, and educators — discuss all things entrepreneurship and venture capital.

  1. 2D AGO

    Dan Caffee: Sold Teem to WeWork for $100M, Startup Mistakes, Personal Family Tragedy

    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

    1h 32m

  2. FEB 5

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

    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

    1h 26m

  3. JAN 29

    Matt Stapleton: Turning Excel Sheets into $480M, SaaS Ideas, Strategy, Startups

    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

    1h 12m

  4. JAN 16

    Dave Bateman: How he kept 60% of a Unicorn, Entrata, Bootstrapping, Magic Mushrooms, Silver, Scaling

    In this episode of the Startup Ignition Podcast, Tyler and John sit down with Dave Bateman, the co-founder and former CEO of Entrata, one of Utah’s most successful SaaS unicorns. Dave shares his incredible journey from running a letter-delivery service for missionaries to bootstrapping a multi-billion dollar property management platform. They dive deep into his philosophy of "building it right" versus building it fast, how he taught himself to code to save the company, his unique strategy for scaling offshore teams, and the intense litigation battles that ultimately strengthened Entrata. Dave also opens up about his exit, health challenges, and the personal transformations that led him to prioritize life over business. (00:00:00) Build fast or build it right? (00:02:06) Introducing Dave Bateman and his background (00:04:07) Icebreakers: Silver, gold, and investment strategies (00:05:52) The trap of raising capital for ego vs. bootstrapping (00:10:24) The dangers of using AI to build the wrong product faster (00:11:00) Dave's early life in Montana and learning to hustle (00:15:21) The origin story of DearElder.com (00:20:34) Identifying the paper-ledger problem in property management (00:24:36) Why vertical SaaS solutions beat general software (00:28:37) Winning business competitions and early funding struggles (00:31:20) Throwing away code and fixing architectural debt (00:33:57) Taking over the codebase and solving database bottlenecks (00:38:07) How to actually make offshore development work (00:41:12) The power of transactional revenue combined with SaaS (00:43:11) Doubling revenue annually and avoiding dilution (00:47:42) The "divorce" lawsuit with Yardi Systems (00:49:42) Building a core accounting system from scratch (00:51:58) The 2018 psychedelic retreat that changed Dave’s perspective (00:53:20) Stepping down as CEO and the transition to Adam Edmonds (00:55:03) Controversy, COVID-19, and standing by convictions (00:59:55) Escaping the "more money" merry-go-round (01:01:19) Battling autoimmune disease and natural healing (01:02:08) Tax incentives in Puerto Rico and final advice 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/ #Entrata #SaaS #Bootstrapping #DaveBateman #PropertyTech #Entrepreneurship #StartupGrowth #SoftwareArchitecture #OffshoreDevelopment #VentureCapital #BusinessStrategy #MentalHealth #Biohacking #VerticalSaaS #UtahTech #StartupGrind #FounderStories #TechUnicorn #BusinessProcessAutomation #StartupIgnition

    1h 12m

  5. JAN 1

    Cydni Tetro: Disney R&D, Innovation, 3D Printing, Brandless, Startups, Coke, Tenacity, Women in Tech

    In this episode of the Startup Ignition Podcast, Tyler and John are joined by Cydni Tetro, a serial entrepreneur, tech executive, and absolute legend in the Utah tech scene. Cydni takes us through her remarkable career journey, from balancing a computer science degree while hex editing networks at Novell, to leading innovation at Disney Imagineering’s Blue Sky Group. She shares fascinating stories about creating immersive customer experiences, founding and selling companies like 3D Plus Me and ForgeDX, and her time leading Brandless. We also discuss the importance of tenacity over talent, the risks of building on third-party platforms, and her impact as the founder of the Women Tech Council. (00:00:00) Introduction and welcoming Cydni Tetro (00:02:06) Cydni’s bio: CS grad, Disney Imagineer, and serial entrepreneur (00:04:07) Icebreaker: Rapid fire "This or That" (00:05:52) The risk/reward equation of Equity vs. Salary (00:10:24) In-person vs. Zoom: Reading the room and building relationships (00:11:00) Why tenacity beats talent in founders (00:15:21) Cydni’s origin story: Novell and the power of a technical background (00:20:34) Moving to startups: The NextPage years (00:24:36) How a technical degree gets you a seat at the decision-making table (00:28:37) Family Link, the Facebook API, and the dangers of platform dependency (00:31:20) The "Utah Tech Web" and connections to VidAngel and Angel Studios (00:33:57) Joining Disney Imagineering: Innovation with no constraints (00:38:07) Creating the "Glow with the Show" Mickey ears for Cars Land (00:41:12) Disney’s ecosystem: Steamboat Ventures and internal innovation (00:43:11) Leaving the Mouse to capture the upside: Founding 3D Plus Me (00:47:42) How 3D Plus Me turned fans into Iron Man action figures (00:49:42) The tech behind full-color 3D printing and scaling with Hasbro (00:51:58) Selling 3D Plus Me and founding ForgeDX (00:53:20) The origin and economic impact of the Women Tech Council (00:55:03) ForgeDX: Visualizing digital transformation for Fortune 500s (00:59:55) Brandless: Strategies behind the consolidation and acquisition model (01:01:19) The economic shifts of 2021 and their impact on CPG (01:02:08) Digital transformation and AI at Swire Coca-Cola (01:06:52) The current state of women in entrepreneurship and funding (01:12:47) Final advice: Leave every place better than you found it 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/ #CydniTetro #DisneyImagineering #WomenInTech #StartupIgnition #UtahTech #SerialEntrepreneur #ProductManagement #CustomerExperience #Brandless #3DPrinting #Innovation #VentureCapital #Novell #TechLeadership #Storytelling #WomenTechCouncil #AngelInvesting #StartupAdvice #Tenacity #DigitalTransformation

    1h 19m

  6. 12/18/2025

    John & Tyler go over the Carta Q3 Pre-Seed Analysis, Early Stage Trends, VC, SaaS

    In this episode of the Startup Ignition Podcast, Tyler and John Richards break down the latest data from Carta’s Q3 2025 State of Pre-Seed report. They analyze the current venture landscape, discussing why funding has seen a seasonal decline, the bifurcation of round sizes into "tiny" and "monster" deals, and why capital efficiency is becoming the new standard. The duo also plays a "fill in the blank" icebreaker covering pitch deck mistakes and founder superpowers, and they debate whether AI has dethroned SaaS as the king of investment sectors. (00:00:00) The "Unicorn Whirlpool" and the dangers of raising too much too early (00:01:06) Welcome to the show: A cold December in Utah (00:02:06) Icebreaker: The fastest way to lose a $500k pre-seed round (00:03:26) Icebreaker: A founder's true superpower is understanding the customer (00:04:07) Icebreaker: A pitch deck is not complete without a Go-to-Market strategy (00:07:23) Icebreaker: The one slide we would ban from pitch decks forever (00:10:42) Icebreaker: When do we know a founder is going to be successful? (00:14:48) Decoding the Data: Carta’s Q3 2025 State of Pre-Seed Report (00:17:14) Data Insight: Pre-seed funding declined by cash raised and deal count (00:19:25) Data Insight: The "Barbell Market" (Tiny rounds vs. Monster rounds) (00:27:04) Data Insight: How many checks does it really take to fill a round? (00:28:41) A warning against taking small checks from non-accredited investors (00:31:54) Data Insight: The absolute dominance of SAFEs over convertible notes (00:36:46) Data Insight: Geography still matters (The West Coast dominates) (00:41:28) Data Insight: SaaS is still King (and the Gartner Hype Cycle) (00:47:25) Why John and Tyler stick to Pre-Seed investing despite the risks (00:50:21) Summary: Capital is concentrated, disciplined, and tethered to traction 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 #PreSeed #VentureCapital #CartaData #Fundraising #SaaS #AngelInvesting #FounderAdvice #CapitalEfficiency #SafeAgreements #StartupFunding #UnicornWhirlpool #PitchDeck #BusinessStrategy #Entrepreneurship #StartupTrends #GoToMarket #InvestorTips #SiliconSlopes #UtahStartups

    53 min

  7. 12/11/2025

    Ryan Westwood: Slow Down to Speed Up, His $250M Exit to Infosys, Buying 7 Competitors, Scaling

    In this episode of the Startup Ignition Podcast, we sit down with Ryan Westwood, a prolific entrepreneur and investor who recently scaled Simplus from zero to 600 employees and sold it to Infosys for $250 million. Ryan shares his incredible journey from weeding gardens to earn his first pair of Air Maxes to executing a massive "roll-up" strategy in the Salesforce ecosystem. We dive deep into the mechanics of acquiring companies to increase valuation multiples, the importance of "slowing down to speed up," and how he is applying his playbook to his newest venture, Fullcast. Ryan also opens up about family philanthropy, the discipline of meditation, and the relentless mindset required to win. (00:00:00) Introduction to Ryan Westwood and his $250M exit (00:02:06) Reading Ryan’s bio: Entrepreneur, Investor, and Philanthropist (00:04:07) Startup Mad Libs: "Venture Capital is your enemy" (00:05:52) The biggest startup killer: Premature scaling (00:10:24) Ryan’s 4 rules for investing in a company (00:11:00) Angel investing and focusing on building Fullcast (00:15:21) Earning Nikes at age 11: The reward of hard work (00:20:34) Shifting from tech to revenue generation (00:24:36) Living on $1450/month to save capital for the first startup (00:28:37) The origins of Simplus and identifying the CPQ opportunity (00:31:20) Finding a niche in Salesforce customization (00:33:57) The "Roll-up" Strategy: Acquiring 7 competitors in 3 years (00:38:07) The current state of Private Equity and finding buyers (00:41:12) Using a mix of debt, equity, and cash for acquisitions (00:43:11) The paranoia of closing a deal during the onset of COVID (00:47:42) Using a Series C "Blocker" to negotiate a higher price (00:49:42) Why Ryan left Infosys despite a $150M EBITDA year (00:51:58) Drafting off the Salesforce brand and staying differentiated (00:53:20) "Jab, Jab, Right Hook": Giving value before asking for the sale (00:55:03) Networking and the power of being a good person (00:59:55) The Fullcast story: Buying a company to fix sales operations (01:01:19) Rolling equity and doubling down on the new venture (01:02:08) Growing Fullcast valuation to $125M in seven quarters 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/ #RyanWestwood #Simplus #Fullcast #ExitStrategy #Salesforce #Acquisitions #StartupFunding #RevenueGrowth #EntrepreneurMindset #Philanthropy #Meditation #BusinessStrategy #VentureCapital #RollUpStrategy #SaaS #AngelInvesting #Leadership #StartupIgnition #JohnRichards #TylerRichards

    1h 10m

  8. 12/04/2025

    Paul Ahlstrom: The Origins of Nail It Then Scale It, Market Timing, Utah VC, AI

    In this episode of the Startup Ignition Podcast, we sit down with Paul Ahlstrom, a serial entrepreneur, investor, and one of the key architects of the Utah venture capital ecosystem. Paul shares his incredible journey from early failures—including a software bug that wiped out his first business overnight—to founding vSpring Capital and helping transform Utah into a tech powerhouse. He also discusses his pioneering work building the VC infrastructure in Mexico, the personal struggles that led to co-authoring the foundational book Nail It Then Scale It, and his predictions for the future of the "autonomous economy" and agentic AI. (00:00:00) The software bug that killed a business overnight (00:04:36) Icebreaker: Playing "Pivot or Persevere" with startup scenarios (00:09:16) Why big competitors validating your market is a good thing (00:16:04) Paul’s early hustle: From pool cleaning to 80s dance clubs (00:22:04) The Folio years and the founding of Knowlix (00:26:40) Escaping the Dot Com crash: The "Shoeshine Boy" indicator (00:29:31) Founding vSpring Capital: Bringing oxygen to Utah startups (00:35:41) The lack of capital in the early Utah ecosystem (00:39:53) Expanding to Latin America and building Mexico’s VC laws (00:47:50) The emotional origin story of Nail It Then Scale It (00:50:38) Collaborating with Nathan Furr and the Lean Startup connection (00:53:20) How a "victim of the internet" article led to the book's methodology (00:59:07) The #1 cause of startup failure vs. the #1 indicator of success (01:00:05) Understanding "Why Now?" and market timing (01:03:26) The future of tech: The Agentic Economy and AI saturation (01:05:49) How modern tools allow rapid iteration and validation 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/ #PaulAhlstrom #VentureCapital #NailItThenScaleIt #StartupAdvice #UtahTech #vSpringCapital #PivotOrPersevere #MarketTiming #AgenticAI #Entrepreneurship #StartupIgnition #LeanStartup #ProductMarketFit #TechHistory #BusinessStrategy #StartupFunding #MexicoVC #StartupMistakes #FounderStories #FutureOfWork

    1h 9m
See All (43)

Ratings & Reviews

5
out of 5
10 Ratings

About

Father and son team John and Tyler Richards — veteran entrepreneurs, venture investors, mentors, and educators — discuss all things entrepreneurship and venture capital.

Information

  • Creator
    John & Tyler Richards
  • Years Active
    2025 - 2026
  • Episodes
    43
  • Rating
    Clean
  • Copyright
    © Startup Ignition Academy, Inc.
  • Show Website
    Startup Ignition Podcast

You Might Also Like