CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Every week I tackle management, operations & startup topics that are helping 250,000+ people. Sign up free: www.scotchisholm.com

I also run a leadership accelerator that helps founders develop into top CEOs. Apply here: https://joinhighland.com/apply/

My backstory: 

🚀 Founder of Classy, SaaS for nonprofits raising billions per year

🎗️ Acquired by GoFundMe in ‘22 to create largest giving platform in the world

🌲 Investor in dozens of startups out of family fund, Tall Timbers Holding Co, (Ripple, FanDuel, Hubble, Casetext, etc.)

🏔️ Founder of Highland, leadership accelerator & community for founders

🏡 Co-founder of Haskill Creek, modernized & healthier version of a Walgreens or CVS 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland & food 

⚙️ Industrial engineer & lean six sigma nerd, UMass Amherst grad 

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation

It's been a wild ride. If you're interested in any of the above, please visit my website and reach out to me there. 

www.scotchisholm.com

Scot Chisholm

Hi, I’m Alejandro DeCastro. I graduated from Adelphi University with a degree in Neuroscience, and I’m passionate about making systems work smarter, faster, and better—whether in healthcare, business, or brand development.

Over the years, my path has evolved from hands-on roles in clinical operations and healthcare coordination to leadership in strategy, brand development, and digital innovation. This mix of analytical training and creative execution has shaped how I approach problems: I look for the structures that help people and organizations operate with clarity, efficiency, and purpose.

At Intivio Technologies, I’ve led cross-functional strategy and operations for an AI-driven branding and business development team, collaborating with creative, technical, and client-focused departments. Together, we’ve launched new service lines, built scalable frameworks, and enhanced how businesses connect with their audiences. These experiences have deepened my interest in integrating neuroscience, systems thinking, and business strategy to drive meaningful results.

My main goal is simple: to help people get what they need—care, service, or support—without unnecessary barriers. Whether through workflow design, branding strategy, or organizational development, I’m drawn to work that improves access, simplifies complexity, and creates tangible impact.

Looking ahead, I’m focused on expanding my work at the intersection of healthcare innovation, brand strategy, and operational intelligence—building systems that combine empathy with efficiency.
If you’re working on projects that make healthcare or business more effective, accessible, or forward-thinking, I’d love to connect and learn more about your work.

taplio

The Battle

Scot Chisholm

Alejandro Decastro

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