Biz Mafia : Where Business Gets Made

EP 16: Blazing the Venture Capital Trail in Regenerative Food & Agriculture with Investor Pete Oberle

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In a world where the focus is shifting towards sustainability and responsible investing, a burning question arises: Is regenerative agriculture the future of sustainable investing?


In this episode of the BizMafia podcast, we sit down with Pete Oberle, the co-founder and managing director of Trailhead Capital. Trailhead Capital is a mission-driven early stage venture capital firm dedicated to generating outstanding financial, societal, and ecological returns by supporting entrepreneurs who are building the regenerative future of food and agriculture. 


Pete's tale is one of fervor and resolve. Hailing from a bulge bracket financial and private equity background, he found his true calling in venture capital, driven by a deep-seated ambition to enhance human well-being and confront the imminent challenges posed in the regenerative food and agriculture space. Pete generously shares his insights on the economic gains and technological strides that are propelling this sector forward.


Don't pass up on this chance to broaden your horizons. Tune in, stay engaged, and let's embark on this journey together.

What We Discuss
  • [00:33] - Meet Pete Oberle
  • [13:21] - Pete's transition from private equity to venture capital 
  • [17:39] - Evaluating financial potential in the regenerative agriculture space
  • [20:14] - Consumer sophistication and supply chain issues  
  • [22:25] - Early-stage investing challenges  
  • [23:35] - Filtering investment opportunities  
  • [24:21] - Criteria for evaluating founders 
  • [27:29] - Evaluating company progress  
  • [29:33] - Strategic planning and involvement  
  • [32:58] - Role of board members  
  • [42:09] - Valuation and founder position  
  • [45:13] - Early-stage VC in the capital stack  
  • [45:26] - The capital needs of the space  
  • [46:32] - Funding considerations and future plans  
  • [50:41] - Personal and professional transitions  
  • [54:11] - Mitigating risk in making career changes  


    • Notable Quotes
    • [48:35] - “We're trying to thread the needle between concessionary and market-driven returns, and ‘Big Ag’ versus regenerative purists. It's important that we're absolutely pursuing market-driven returns.” - Pete Oberle 


    • [49:43] - “We try to be bridge builders, essential to the overall ecosystem. ‘Big Ag’ is not going anywhere, and they are trying to improve operations. They just need to be clearly educated and presented with profitable opportunities.” - Pete Oberle 


    • [54:11] “What's holding so many of us back from making changes? It's fear that what we're doing may seem crazy or questionable, but with the resources out there, the risk of making a change is incredibly mitigated.” - Pete Oberle


    Our Guest

    Peter Oberle is a seasoned professional in venture capital and strategic leadership. Currently, he holds the role of Managing Partner at Trailhead Capital, spearheading investment strategies in Colorado. With a background in finance from the University of Pennsylvania and a BA from Dartmouth College, Peter brings a wealth of expertise to his board positions at FoodMaven and Clean Crop Technologies, driving innovation in sustainable solutions.


    Resources and Links
    • Trailhead Capital Website: https://www.trailheadcap.com/


    • Connect with Pete Oberle on LinkedIn: https://www.linkedin.com/in/pete-oberle-5593849a/


    • BizMafia Website: https://www.bizmafia.net
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      • Connect with Pat Linden on LinkedIn: https://www.linkedin.com/in/pat-linden
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        Biz Mafia : Where Business Gets MadeBy Bryan Taylor and Pat Linden