The Worst Startup Advice Ever with Scot Chisholm | TFJP 90

Is ‘Fail Fast’ the worst advice for startups?
In this episode of The Founders Journey Podcast, Greg Moran, Peter Dean, and Scot Chisholm (founder of Classy) dive deep into the myths surrounding popular startup advice like “fail fast” and “find a bigger market.” Scott shares hard-earned lessons from Classy’s journey, including the importance of aligning with the right investors, avoiding premature scaling, and building a sustainable business.

:bulb: What You’ll Learn:
- Why “fail fast” often leads to bad pivots
- How to align with investors who share your values
- The dangers of scaling too quickly
- Lessons from Classy’s path to becoming a unicorn
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:alarm_clock: Timestamps:0:00 - Introduction: Failing Fast Misunderstood
0:23 - What Pivoting Really Means
0:43 - Welcome to Founders Journey Podcast
0:57 - Reunion with Peter Dean
1:12 - Introducing Scott Chisholm, Founder of Classy
2:28 - Scott’s Journey: Classy’s Origins and Growth
4:00 - Challenges in Nonprofit Technology Adoption
6:00 - Private Equity Challenges and Lessons Learned
8:00 - Culture Shift and Boardroom Conflicts
10:33 - Rescuing the Company from Investor Issues
14:13 - Importance of Value Alignment with Investors
15:10 - Building Relationships with the Right Partners
17:00 - Worst Advice in Startups: Failing Fast Critiqued
20:48 - Why Founders Should Avoid Constant Pivoting
23:07 - Business with Friends: A Debate
26:15 - Focus on Core Markets First
29:00 - Shiny Object Syndrome in Hiring Experienced Executives
34:00 - Raising Capital: The Right Approach
38:10 - Transitioning from Bootstrapping to Spending Methodically
42:50 - Balancing Frugality with Scaling
46:00 - How to Reach and Work with Scott Chisholm
47:25 - Closing Remarks and Future Advice
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Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/

website link of the guest -  scotchisholm.com
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