A Bad Investor is Worse Than No Investor episode artwork

EPISODE · Sep 16, 2025 · 31 MIN

A Bad Investor is Worse Than No Investor

from We Live to Build

Every founder needs to hear this: A Bad Investor is Worse Than No Investor. Before you start chasing venture capital, you must understand the risks. In this interview, M&A expert Scott Kelly explains why bootstrapped founders of seven, eight, and even nine-figure brands often love their lives, while many VC-backed founders are miserably stressed. We break down the cautionary tale of FanDuel, whose founders got "little or nothing" after raising hundreds of millions, versus MailChimp, whose founders kept 98% of the proceeds from their exit after bootstrapping. This is a must-watch for any entrepreneur deciding how to fund their business. Check out the company: https://blackdogvp.com----------------------------------------------------------------------------------------------------------------------------📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------▶ Get my eBook free - https://welivetobuild.com/network-----------------------------------📈 WORK WITH ME-----------------------------------▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call▶ Startup Fundraising: https://welivetobuild.com/fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------👀 CONNECT WITH SEAN---------------------------------------------▶ LinkedIn: https://linkedin.com/in/seanweisbrot▶ Inquiries: [email protected]🕒 CHAPTERS---------------------------00:00 - The Art of Finding the Right Partner03:29 - The #1 Thing Founders Must Do Before Starting06:27 - The VC Trap: Chasing Fundraising vs. Building a Business08:13 - Quantity vs. Quality of Life: A Founder's Choice11:04 - The Warning: MailChimp (Bootstrap) vs. FanDuel (VC)13:40 - M&A is Sexy, But It's an Art16:48 - The Dirty Secret of VC Due Diligence21:49 - Why a Bad Investor is Worse Than No Investor25:12 - Why I Love Bootstrapped Founders28:01 - Start With The End in MindLeave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

Every founder needs to hear this: A Bad Investor is Worse Than No Investor. Before you start chasing venture capital, you must understand the risks. In this interview, M&A expert Scott Kelly explains why bootstrapped founders of seven, eight, and even nine-figure brands often love their lives, while many VC-backed founders are miserably stressed. We break down the cautionary tale of FanDuel, whose founders got "little or nothing" after raising hundreds of millions, versus MailChimp, whose founders kept 98% of the proceeds from their exit after bootstrapping. This is a must-watch for any entrepreneur deciding how to fund their business. Check out the company: https://blackdogvp.com----------------------------------------------------------------------------------------------------------------------------📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------▶ Get my eBook free - https://welivetobuild.com/network-----------------------------------📈 WORK WITH ME-----------------------------------▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call▶ Startup Fundraising: https://welivetobuild.com/fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------👀 CONNECT WITH SEAN---------------------------------------------▶ LinkedIn: https://linkedin.com/in/seanweisbrot▶ Inquiries: [email protected]🕒 CHAPTERS---------------------------00:00 - The Art of Finding the Right Partner03:29 - The #1 Thing Founders Must Do Before Starting06:27 - The VC Trap: Chasing Fundraising vs. Building a Business08:13 - Quantity vs. Quality of Life: A Founder's Choice11:04 - The Warning: MailChimp (Bootstrap) vs. FanDuel (VC)13:40 - M&A is Sexy, But It's an Art16:48 - The Dirty Secret of VC Due Diligence21:49 - Why a Bad Investor is Worse Than No Investor25:12 - Why I Love Bootstrapped Founders28:01 - Start With The End in MindLeave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

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A Bad Investor is Worse Than No Investor

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This episode was published on September 16, 2025.

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Every founder needs to hear this: A Bad Investor is Worse Than No Investor. Before you start chasing venture capital, you must understand the risks. In this interview, M&A expert Scott Kelly explains why bootstrapped founders of seven, eight, and...

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