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.vcThis episode was brought to you by Pelion. Check them out here: pelionvp.com

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/

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.comThis episode was brought to you by Pelion, a VC firm based in Utah. Learn more about them here: pelionvp.com

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.comThis episode was brought to you by Pelion Venture Partners. You can learn more about them here: pelionvc.comIf you liked this episode, don't forget to like, share, and subscribe to the channel.

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.comThis episode of the IO Podcast was brought to you by Pelion Venture Partners. Learn more about Pelion here: https://pelionvp.com

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/

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/

How on earth do startup founders with zero experience in the security industry sell millions of dollars in contracts to police stations around the US?In this episode of Exceptional Startups, Garrett Langley, founder and CEO of Flock Safety, breaks down step-by-step 1) How they did it, 2) What process gave them the idea to go after crime, and 3), The biggest lessons he's learned during Flock Safety's rocket-like growth.Chapters:(00:00:00) Flock Safety's Impact on Crime Solving(00:11:05) Innovative Solutions for Crime Prevention(00:11:51) Community Safety Solutions through Innovative Technology(00:18:06) Daily Customer Engagement for Business Success(00:21:04) Strategic Management for Hardware-Enabled SaaS Businesses(00:24:48) Managing Costs for Hardware Startup Funding(00:32:48) Crime Reduction Revolution with Flock's Technology——Check out Flock Safety: https://www.flocksafety.com/Check out PELION: https://pelionvp.com/Subscribe for more!

With so many AI startups these days, how do you identify which will be home-runs and which will be flops?In this episode of the I/O Podcast, Tyler and Sterling sit down with Eric Vishria, a General Partner at the legendary Benchmark Capital, who uncovers their exact process for finding and funding some of the world's fastest-growing and most successful AI startups.Chapters:(00:07:28) Exponential Rise of AI Startups(00:10:21) Diverse Revenue Paths in AI Startups(00:14:10) LLM-enhanced Vertical AI Solutions for Industry(00:18:25) Tech Product Success through Market Awareness(00:20:05) Balancing Human Expertise with AI Automation(00:35:22) The Value of Venture Capital Partnerships(00:37:48) Founders' Partnerships in Early-Stage Investing(00:47:10) Key Questions: The Core of Investing Decisions(00:54:22) Supporting Founders in Venture Capital Industry———Learn more about Benchmark here: https://www.benchmark.com/This podcast was brought to you by Pelion Venture Partners. Have a great startup idea? Learn more about Pelion here: https://pelionvp.com/

How do you get paying customers...before you've even built your product? Time to find out!In this episode of Exceptional Startups, Tyler sits down with John Andrew Entwistle, Founder and CEO of Wander, the platform that's transforming the vacation-rental space.Tyler and John Andrew discuss waitlist tactics, how to solve the supply-and-demand problem for marketplace companies, and how to build a great employee culture.Chapters:(00:01:40) The Idea For A Efficient Vacation Rental Management Platform(00:05:42) The Business Growth Strategies at Wander(00:07:05) Solving The Supply Problem(00:11:53) Transition to Third-Party Inventory Strategy(00:20:17) Transaction vs. Subscription Revenue Models in Software(00:27:48) Visionary Hiring Culture at Wander(00:29:58) How Exceptional Service Elevates Wander's Customer ExperienceCheck out Wander: https://www.wander.com/Check out PELION: https://pelionvp.com/