The IO Podcast: Investor + Operator

Sterling Snow and Tyler Hogge
  • 3.0 (2)
  • INVESTING
  • UPDATED MONTHLY

The Investor + Operator (IO) Podcast hosts the most candid, vulnerable conversations about building companies with the world’s best operators and investors.

  1. Why The Second Decade Is The Best For Startups — A convo w/ Spenser Skates, CEO Amplitude Analytics

    12/16/2025

    Why The Second Decade Is The Best For Startups — A convo w/ Spenser Skates, CEO Amplitude Analytics

    In today's episode, Tyler and Sterling sit down with Spenser Skates, Founder and CEO of Amplitude Analytics, the digital Analytics platform that helps thousand of businesses find ways to grow and improve. Spenser shares how he got his first investors, how to have the best relationships with VCs, his mindset around product and employees, and everything he's learned from over a decade growing his company, taking it public, and beyond! Chapters: (00:00:00) Intro (00:09:36) Why Eric Vishria from Benchmark is the top investor of this generation (00:17:05) How great investors actually help massively (00:25:45) how do you stay motivated during the second decade? (00:33:57) how does Spenser judge whether he's successful as a ceo? (00:40:16) why he's more vocal on x (00:45:00) who is his favorite operator? (00:47:25) recap -- Subscribe for more startup content! Check out Amplitude: https://amplitude.com/ This podcast was brought to you by PELION. Learn more about them here: https://pelionvc.com/

    52 min
  2. Ex Navy SEAL: When To Quit Vs Persevere In Business + How I Started A Successful Venture Firm!

    10/14/2025

    Ex Navy SEAL: When To Quit Vs Persevere In Business + How I Started A Successful Venture Firm!

    A question every startup founder has is, "When do I know when to keep going or throw in the towel?" Today, Tyler and Sterling sit down with ex Navy Seal and Olympian, Larsen Jensen, to talk about just that. Larsen is the founder of Harpoon Ventures, an investment firm focused on building companies that assist the armed forces. He is also the founder and CEO of Vector, a tech company focused on building products to assist the armed forces. Larsen talks about how he got into the Olympics, became a Navy Seal, and then started Harpoon, even when everyone thought he was crazy for going into military investing! He shares his lessons on perseverance, and what it takes to succeed. If you're a founder, you won't want to miss this! Chapters: (00:00:00) Intro (00:08:53) Becoming an Olympian (00:11:29) Meeting the President (00:15:34) Becoming a Navy SEAL (00:19:00) Survival Rates in BUD/S Training (00:22:28) How to know when to Quit (00:25:40) Navigating Startup Challenges (00:30:03) Why Larsen Started Harpoon Ventures (00:34:56) Government Sales Cycle Mentorship Program (00:37:48) Andreessen Horowitz (00:40:41) What Drives Larsen? —— Check out Harpoon Ventures: www.harpoon.vc This episode was brought to you by Pelion. Check them out here: pelionvp.com

    42 min
  3. Zero To $1 BILLION In Payments In Just One Year: How To Crush Product-Market-Fit w/ Joshua Silver

    09/30/2025

    Zero To $1 BILLION In Payments In Just One Year: How To Crush Product-Market-Fit w/ Joshua Silver

    Usually small startups fail when trying to take on big companies. Rainforest, however, is a different story. In the payments space dominated by Stripe and PayPal, founder Joshua Silver saw a gap no one was paying attention to. The result? Over $1 Billion in transactions in their first year! In this convo, Joshua explains how he found the opportunity, the steps he took to dominate it, and his mindset when it comes to nailing product-market-fit in a crowded space. Chapters: (00:00:00) Intro (00:00:56) Payment Processing's Role in SaaS Revenue (00:02:07) How Rainforest Succeeded So Quickly (00:05:42) Strategy For Breaking Into The Market (00:15:17) How They Beat The Competition (00:17:50) The 1 Metric To Focus On (00:21:49) The Best Thing He Did While Fundraising —— Subscribe for more startup content! Check out Rainforest: https://www.rainforestpay.com/ Check out PELION: https://pelionvp.com/

    28 min
  4. $500M Founder: Avoid These Critical Mistakes When Competing With Incumbents - A convo w/ Daniel Simon, Coast CEO

    09/16/2025

    $500M Founder: Avoid These Critical Mistakes When Competing With Incumbents - A convo w/ Daniel Simon, Coast CEO

    Are you a small startup trying to compete with the big dogs? Well then this episode is for you. Tyler and Sterling sit down with Daniel Simon, co-founder of Bread (sold for $500M) who is now working on his next big startup: Coast, a fuel card and payment platform for companies that manage large fleets of vehicles. Daniel breaks down his learnings from his time at Bread, what he's doing differently now at Coast, and the important lessons he's learned from building successful companies in niches that are already dominated by large incumbents. Subscribe to never miss an episode! Chapters: (00:00:00) Intro (00:02:09) Disrupting Fleet-Centric Financial Services (00:05:20) Different vs. Better when competing with Incumbents (00:10:14) Customer Feedback for Product Innovation (00:16:34) Finding Partners for Capital Acquisition (00:21:07) How to Fundraise Effectively (00:24:03) Attracting Investors (00:26:38) Iterative Product Development through Sales Feedback -- Check out Coast: coastpay.com This episode was brought to you by Pelion, a VC firm based in Utah. Learn more about them here: pelionvp.com

    34 min
  5. Kapital: The Future of Latin-American Banking With Mexico’s Best Startup

    09/02/2025

    Kapital: The Future of Latin-American Banking With Mexico’s Best Startup

    If you need some motivation as an entrepreneur, then this is the podcast episode for you. In today's video Tyler and Sterling sit down with Rene Saul, the CEO and co-founder of Kapital, the $1.3 billion-dollar startup from Mexico City that is transforming the Latin-American banking space forever. Rene breaks down how they got started, the lessons and failures they've had along the way, and how he developed the resilience and energy that has allowed him to overcome all of the startups obstacles that have come their way. His energy is off the charts! Chapters: (00:00:00) Intro (00:05:06) How Past Ventures Shaped Kapital's Success (00:15:04) Mexico's Innovative Tech Center Transformation through SMBs (00:18:45) Running Marathons (00:22:24) Resilience and Perseverance in Business Success (00:27:34) Overcoming Setbacks: The Entrepreneurial Resilience Journey -- Check out Kapital: kapital.com This episode was brought to you by Pelion Venture Partners. You can learn more about them here: pelionvc.com If you liked this episode, don't forget to like, share, and subscribe to the channel.

    29 min
  6. Lessons From Building Utah's Next $10B Company — A convo w/ Adam Edmunds, CEO of Entrata

    08/12/2025

    Lessons From Building Utah's Next $10B Company — A convo w/ Adam Edmunds, CEO of Entrata

    If you haven't heard of Entrata yet, then you need to listen to this episode. Entrata is a sleeping giant of a company that has quietly been growing in the background...and is on track to be the biggest company to ever come out of Utah. In this episode, Tyler and Sterling sit down with their friend Adam Edmunds, CEO of Entrata, as he breaks down how he found the company, how fast it's growing, and the biggest lessons he's learned along the way. -- CHAPTERS: (00:00:00) Intro (00:05:53) Blackstone Investment + Tips For Fundraising (00:10:14) Cap Table Strategies (00:12:54) Why Adam Joined Entrata (00:15:25) Masterclass On Recruiting (00:27:30) Lessons From Running A 4,500 Person Company (00:33:21) Company Growth Vs Preserving Culture (00:37:27) What Drives Adam Personally -- Check out Entrata: www.entrata.com This episode of the IO Podcast was brought to you by Pelion Venture Partners. Learn more about Pelion here: https://pelionvp.com

    40 min
  7. Leading a $1B Revenue Startup AND $1.8B VC Firm – A convo w/ Arjun Sethi (Tribe Capital + Kraken)

    07/29/2025

    Leading a $1B Revenue Startup AND $1.8B VC Firm – A convo w/ Arjun Sethi (Tribe Capital + Kraken)

    Hands-down, Arjun is the most interesting man in venture capital. He thinks differently than everyone else, and as a result, his VC Firm, Tribe Capital, and his startup, Kraken, are completely unique. In this episode, he shares how he got started, and the exact tools he used to get where he is today... Check out Tribe Capital: https://tribecap.co/ Check out Kraken: https://www.kraken.com/ Subscribe to never miss an episode! -- Chapters: (00:00:00) Intro (00:00:56) Startup Incubation Model for High Returns (00:10:30) Passionate Projects: Impactful Progress for Humanity (00:13:49) Enhancing Product Market Fit with Frameworks (00:16:40) User Behavior Analysis for Product Success (00:18:28) Product Market Fit Analysis for Investors (00:27:49) Identifying Compelling Investment Trends in Emerging Markets (00:30:12) Enhancing Business Operations with Modern Tools (00:34:02) Tribe's Hands-On Incubator Approach (00:41:50) Crypto and Kraken (00:46:16) Data-Driven Transparency for Organizational Alignment (00:50:41) Enhancing Global Liquidity with Stablecoins (01:05:01) Balancing Innovation with Traditional Principles in Lifestyle ––– This podcast was brought to you by Pelion Venture Partners. Check them out here: https://pelionvp.com/

    1h 8m
  8. How The BEST Founders Go From Seed To Series A - a convo w/ Brett Berson of First Round

    07/15/2025

    How The BEST Founders Go From Seed To Series A - a convo w/ Brett Berson of First Round

    What are the questions founders and VC firms should be asking when raising a Series A? How will AI impact things? What are the common pitfalls for Seed-stage startups? In this episode, Tyler and Sterling sit down with Brett Berson of First Round Capital to answer all these questions and more. -- Chapters: (00:00:00) Intro (00:00:29) Future of Venture Capital in Software Development (00:10:24) "Ubiquitous Software Development: Changing Industry Dynamics" (00:14:03) Navigating Economic Shifts in B2B Software (00:16:35) Power Law Business Funding for Startups (00:20:15) Attracting Venture Capital Through Unique Expertise (00:22:31) Founders' High Regard for First Round (00:31:29) Foundational Support for Seed to Series A (00:35:24) Founders' Autonomy in Navigating Funding Rounds (00:39:19) Narrative-Driven Fundraising Strategy Development Process (00:47:54) Strategic Investor Relationship Building for Fundraising Success -- Check out First Round: https://www.firstround.com/ This podcast is brought to you by PELION: https://pelionvp.com/

    1h 2m
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About

The Investor + Operator (IO) Podcast hosts the most candid, vulnerable conversations about building companies with the world’s best operators and investors.

Information

  • Creator
    Sterling Snow and Tyler Hogge
  • Years Active
    2023 - 2025
  • Episodes
    31
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 Sterling Snow and Tyler Hogge
  • Show Website
    The IO Podcast: Investor + Operator