Rebuilding and Learning from Failure with Steven Plappert

How one founder rebuilt reputation and business after public failure


Do you have what it takes to start all over again?

In this episode, we’re joined by Steven Plappert, the resilient entrepreneur behind Forecastr and former co-founder of FantasyHub. Steven opens up about the emotional rollercoaster of launching startups, the invaluable lessons learned from his humiliating public failure, and the role relationships played in his ability to bounce back and find success.

Join us as we explore his journey, the power of building a strong community, and the importance of maintaining balance and boundaries amid the chaos of entrepreneurship. 

Key Takeaways:

  • People and Relationships are the Foundation of Success: Building a business isn't just about the numbers—it's about the people. Cultivating strong relationships with co-founders, team members, and investors is crucial to your success. 
  • Resilience in the Face of Failure: Entrepreneurs often face setbacks, but it's how you rise from these challenges that define your journey. Steven's story of bouncing back from the public failure of Fantasy Hub to founding Forecastr underscores the importance of resilience.
  • Balance and Boundaries Fuel Leadership: Scaling a business requires intense focus, but establishing balance is essential to sustain that momentum. Steven's approach to recharging—like hiking and mountaineering—is a reminder for how crucial activities outside of work are.


00:00 Third-generation entrepreneur and family legacy

05:24 Shared experience of failed startups

09:06 Legal sports betting and financial trouble

12:37 Death threats and business failure

15:50 Starting Forecastr in the mountains

23:40 Forecastr's success

34:32 Co-founder relationship: highs, lows, pros, cons

37:18 Challenges of starting a tech company

44:35 Prioritizing personal relationships


Riding two rollercoasters: work and personal with Devin Bramhall


Rebuilding and Learning from Failure with Steven Plappert


How Lee Rubin pivoted and built a Top 10 Fastest-Growing Tech Company


The Impact of Aligning Your Company with Your Values with Michael King


From Trouble to Triumph: Lessons in Resilience with Tiffany Sauder


Embracing Imperfection with Nick Smarrelli


Scaling to 500 and Stepping Down with Mark Caswell

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