The Untold Truth: Controversy Marketing, Founder Burnout, and Selling for $MM - Misfit Founders Ep 4

Misfit Founders

In this episode, I engage in a conversation with Chris Cooke, the founder of Old Street Solutions. Chris and I draw parallels and distinctions in our paths from founding to selling businesses, revealing unique approaches to entrepreneurship.
Our discussion dives into Chris's remarkable trajectory—embarking from entrepreneurial ventures in Thailand, transitioning into a proficient salesman, embarking on a journey of launching a B2B product startup, and ultimately orchestrating a multi-million-dollar transaction. Despite the financial success, Chris candidly shares his sense of disorientation after this significant achievement.
Furthermore, we delve into Chris's unconventional marketing methodologies, including his employment of a Hip Hop video for hiring talent and bold tactics of challenging competitors. These thought-provoking strategies take centre stage as we dissect their controversial aspects and impact on his business journey.
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#founder-burnout #contreversialmarketing #sellingstartup #misfitfounders #startupchallenges
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Chapters

1. Entrepreneurship, Marketing, and Building Businesses (00:00:00)

2. Entrepreneurship, Failure, and Growth (00:14:51)

3. Co-Founders and Balancing Creativity in Entrepreneurship (00:24:04)

4. Impact of Hip Hop Video (00:36:49)

5. Considerations for Selling a Business (00:46:50)

6. Collaboration Between Technical and Non-Technical Roles (00:59:59)

7. Navigating Post-Exit Identity and Future Plans (01:08:06)

8. Exploring Reasons for Non-Collaboration (01:15:44)

9. Finding Mentors and Support for Growth (01:25:20)

10. Finding Passion and Success in Life (01:32:39)