Unfair Edge with Chase McCaskill

Chase McCaskill

5.0 (1)
Entrepreneurship
Weekly

Conversations with founders to give you an unfair edge in building your startup!

11/03/2025

Sheel Mohnot's Advice to Founders from 3 Exits and Fundraising $450M

Sheel Mohnot, Co-Founder of Better Tomorrow Ventures, shares lessons from building and selling startups to raising a $450M fintech fund, revealing how he evaluates founders, runs focused fundraising rounds, and sees today’s pre-seed to Series A landscape evolving. What you’ll learn: How to make the leap from consultant to founderHow to run a focused fundraising processMilestones that actually matter to investorsWhat VCs expect at Series A — ARR, valuation, and tractionThe founder traits that winWhen you should raise Linkedin: https://www.linkedin.com/in/smohnot/ Twitter: https://x.com/pitdesi Better Tomorrow Ventures: https://www.btv.vc/ Chapters 02:15 - Leaving Consulting to Start FeeFighters 06:45 - Selling to Groupon & The Groupon Mafia 12:40 - Founding Innovative Auctions & Building Again 14:00 - Creating (and Exiting) The Pitch Podcast 20:45 - How Sheel Started Angel Investing 22:50 - Founding Better Tomorrow Ventures with Jake Gibson 27:30 - Lessons from Raising Fund I & Building LP Relationships 34:40 - The 2025 Pre-Seed & Seed Market: What Founders Should Know 40:00 - Seed-Strapping, Runway & Raising to Series A 46:20 - Series A Reality Check: Higher Revenue Expectations 48:20 - What Makes Founders Stand Out to BTV 49:55 - Being Truly “Founder-Friendly” 53:25 - Where the Next Big Fintech Ideas Might Emerge 56:15 - Parting Advice for Founders Fundraising in 2025
07/28/2025

Seed to Series A: Fundraising in 2025 (Peter Walker, Head of Insights @ Carta)

Seed & Series A fundraising in 2025 is a different game. Carta’s Head of Insights, Peter Walker, unpacks valuations, revenue expectations, dilution math, and why an AI-native story is now table-stakes for early-stage founders. What you’ll learn: Why it's harder than ever to raise at Seed.How much ARR you actually need before Series A.Why AI-native positioning is non-negotiable for 2025 fundraising.Solo-founder vs. co-founder data, and what VCs really thinkHow to manage your runwayWhere to build your startupPeter’s content strategy and GTM engine. Linkedin: linkedin.com/in/peterjameswalker Twitter: x.com/PeterJ_Walker Carta: carta.com 00:00 - Intro & Career Path 03:24 - Data-Driven Brand Building 10:40 - LinkedIn Growth Playbook 12:29 - Seed Valuation Trends 18:48 - Series A Revenue Expectations 32:29 - Dilution & Funding Choices 46:47 - Solo Founders & Bootstrapping 54:33 - Where To Build Your Startup 1:05:45 - Final Takeaways for Founders
07/28/2025

$9M at 17: Why He Quit College for Y Combinator!

Discover startup founder tips from Calvin Chen, founder of Fetchr (Y Combinator startup), on Unfair Edge! Learn how to start a company with practical entrepreneurship advice from a founder who sold his first startup for $9M in high school and dropped out of USC to join Y Combinator. In this episode, Calvin shares founder stories, including his journey from Rent-a-Fit to Kopia to Fetchr, revealing startup growth strategies, how to raise venture capital, and how to find a co-founder, among other things! Key Takeaways from this Episode:1. How Calvin pivoted multiple startups to find the right idea2. Strategies for acquiring early users through non-scalable tactics3. The importance of ruthless focus and user-centric decisions4. Tips for applying to Y Combinator and navigating co-founder dynamicsSubscribe for weekly startup founder stories and entrepreneurship advice!Calvin Chen: https://x.com/CalvinnChennFetchr: https://www.fetchr.so/Chapters:00:00 - Welcome & Calvin Chen intro00:45 - Building & exiting a business for $9M (in high school)04:32 - Launching Rent-a-Fit while at USC06:40 - How to recognize if your company has long-term potential or just short-term success08:44 - Pre-seed hustle: Raising from friends & family and running a startup from your dorm12:33 - Why less capital can be an advantage14:42 - How to balance starting a company while also in college; knowing when to shut it down or go all in18:34 - How Calvin pivoted from investment banking to join Y-Combinator, and how he got selected22:39 - Tips for applying to YC23:53 - Peeling back the “orange” curtain; an inside-look at YC30:43 - Pivoting to Kopia36:56 - Learnings from pivoting; how continuous action produces compounding effects42:00 - How to find the right co-founder (or whether you need a co-founder at all)44:59 - Practical strategies for acquiring users; “do things that don’t scale”50:50 - Why ruthless focus separates the winners and losers; prioritizing the right marketing channels56:06 - Deep user obsession: personal calls, delivery runs & feedback loops59:17 - Parting advice for early founders
07/07/2025

How Agree.com Landed 30,000 Users in 6 Months, Marty Ringlein (Co-founder, Agree.com & Co-founder/GP, Adventure Fund)

Marty Ringlein is the co-founder of Agree.com, a free e-signature-plus-payments platform that has attracted 30 000 users in just six months, where he drives product, brand, and growth strategy. Before Agree, he sold his design agency, Nclud, to Twitter, becoming the company’s First Design manager, and later led global R&D at Eventbrite (after selling his second startup). He also co-founded Adventure Fund and has invested in breakout companies such as Brex, Stripe, and SpaceX, among many others. I hope you enjoy the show! Marty Ringlein: ⁠⁠⁠⁠https://x.com/martymadrid⁠⁠⁠⁠ Agree: ⁠⁠⁠⁠Agree.com⁠⁠⁠⁠ 00:00 - Welcome & Marty Ringlein intro 03:26 - Agree.com’s 30k user milestone & seed raise 06:22 - Using design to build trust and familiarity 12:29 - Product-led growth: turning early users into champions 16:32 - Navigating switching costs 22:41 - Shipping an MVP, and when to add new features 32:11 - “Villain brands” & bold market positioning tactics 38:06 - Why a five-letter “.com” boosts credibility and CTR 46:39 - Agent Engine Optimization (AEO), ranking in ChatGPT 53:12 - Built-in virality through product-led growth 57:37 - Driving user growth through Product Hunt & Beehiiv 1:03:00 - Relationship-driven fundraising: closing $3M in 3 weeks 1:06:22 - Key takeaways & closing remarks

4 Episodes

Conversations with founders to give you an unfair edge in building your startup!

Creator

Chase McCaskill
Years Active

2025
Episodes

4
Rating

Clean
Copyright

© Chase McCaskill
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Unfair Edge with Chase McCaskill