Pivot Decisions That I Regret

Personal Experiences By Brad Magrath

🚀 In the journey of entrepreneurship, we make countless decisions daily, but only a few are truly critical to long-term success. Reflecting on my time as a founder, I recognize three pivotal decisions I regret, and I take full responsibility for these moments:

1️⃣ Founder Role: An early investor advised me to step back and let our partner and CEO take the lead. We were hitting our growth and scaling out of the park, heading into our Series B with real momentum. I stepped aside thinking it would empower the team, but it disrupted our dynamic and performance. My recommendation? For founding teams: clearly define and own your team’s ways of working. For investors: avoid rushing to professionalize until it’s the right time.
2️⃣ Fixed Cost Kryptonite: After our Series B, a trusted advisor warned that we had raised too much capital without discipline in our spending. We upscaled to fancy offices and hired aggressively ahead of the curve. This lack of tightness on long-term costs before revenue growth proved detrimental. Post-funding: Spend it in the field, and be aware of the risks of “bozo explosions” and fixed costs that can’t be turned off.
3️⃣ The Missed Exit: We once had the chance for a 10x exit after achieving $6M in trailing annual EBITDA. Without a clear exit strategy, we missed a valuable opportunity, believing too strongly in our billion-dollar vision. Having clarity on exits and stakeholders’ ambitions is critical as you scale.

Every business strives for high-quality decision-making and continuous improvement. In hindsight, we lacked three key elements in our decision-making, which I’ll explore in upcoming posts:
🔍 Clarity on our Decision-Making Framework
🤝 Effective Stakeholder Engagement
💬 High-Quality Alignment and Relationships
To all the founding teams out there: Keep doing hard things. Better and better.
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