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?

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Check out Harpoon Ventures: www.harpoon.vc

This 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

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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.

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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

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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