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Scot Chisholm
CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland
Scot Chisholm is a multi-time founder passionate about management, operations, and startup topics, guiding over 100,000 individuals to become better leaders.
He is an industrial engineer with a specialization in lean six sigma techniques, and holds degrees from the University of Massachusetts Amherst and The University of Manchester.
Scot's entrepreneurial journey includes founding Classy, a SaaS platform benefitting over 10,000 nonprofits and facilitating the raising of billions in donations annually.
In 2022, Classy was acquired by GoFundMe, forming the world's largest giving platform with a total of over $30 billion raised for various causes both individual and nonprofit.
Apart from Classy, Scot has founded Highland, a community and curriculum supporting high-potential founders, as well as Haskill Creek, a health-focused alternative to retail pharmacy giants like Walgreens and CVS.
His diverse portfolio also includes co-founding Cannabis Counter, an artisanal cannabis brand, and Save Farmland, a nonprofit dedicated to preserving local farmland.
In the sports realm, Scot is a co-owner of Albion Soccer Club, a prominent youth soccer organization in the United States.
Beyond his entrepreneurial endeavors, Scot has held board positions in various charitable and conservation organizations such as Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, and the Montana Pediatric Cancer Foundation.
To connect with Scot, one can explore podcast opportunities or press by reaching out via email to partner@scotchisholm.com, subscribe to his newsletter at scotchisholm.com/newsletter, or join his founder-focused private community at joinhighland.com.
Highlights
This is the number one failure pattern in growing companies.
Most annual planning processes are a waste of time because leaders focus on the plan instead of the process. The real value is in the conversation, not the document. When teams skip the hard discussions, they end up with a plan that nobody believes in.
Great annual planning is a forcing function for alignment. It surfaces disagreements, tests assumptions, and pushes leaders to confront reality. If you treat it as a checkbox exercise, you miss the point entirely.
Your plan is only as good as your team’s conviction. The process should build trust, clarity, and real commitment to the path ahead. If your team walks away confused or skeptical, you have not done your job as a leader.
The best leaders do not just run a process—they use planning to re-align, reset, and re-energize their teams for the year ahead.
Want me to teach you how to do this at your company? Check out Highland Academy at https://t.co/s8FW0aC1sV.
10 deadly sins of negotiating: (and how to avoid them)
Most people fumble at the negotiating table. They focus on what they'll say next instead of reading the room.
They rush when they should wait. They cave when they should push.
As someone who’s closed deals worth millions, I've seen every mistake in the book. In fact, I've made most of them myself.
Here are 10 strategies that helped me stop leaving money on the table:
1️⃣ Do your homework
Mistake: no idea what makes the person tick
• Research the person, product & market
• Anticipate their questions & objections
• The more prepared, the more confident you'll be
2️⃣ Collaborate, don’t compete
Mistake: thinking negotiations are zero sum games
• The best negotiators search for win-win scenarios
• Treat the other party like a brainstorming partner
• Not an enemy on the battlefield
3️⃣ Focus on motivations, not price
Mistake: digging in too early on price
• Explore underlying interests and motivations first
• Figure out what they care most about
• Tailor your approach towards areas of highest interest
4️⃣ Demonstrate your full value
Mistake: assuming they understand the full value of the deal
• You need to paint the full picture to get the full value
• Assume they don't understand all the nuances
• Until they do, you won't get full credit for the value you bring to the table
5️⃣ Know what you’re willing to give up
Mistake: unwillingness to part with anything
• Every negotiation has a give and take Identify your negotiables vs. nonnegotiables
• Use your negotiables to give them what they want
• And to protect your non-negotiables
6️⃣ Listen & Learn (in real-time):
Mistake: not using new info from the other party
• If you keep a collaborative tone, both parties will share a lot of new information through the process
• Listen carefully and adapt your approach accordingly
• Ask clarifying questions to ensure full understanding
7️⃣ Don’t be afraid to make the first offer:
Mistake: waiting too long for an offer
• Use all you've learned to make an informed offer
• Aim high (150% of what you'd accept)
• Be respectful but firm on your stance
8️⃣ Embrace the awkward silence
Mistake: getting anxious & talking too much
• After you make an offer, you must be patient
• Don't keep talking to fill the void
• The other person usually negotiates against themselves
• Good things come to those who wait
9️⃣ But be willing to walk away
Mistake: becoming too emotionally attached to a deal
• Convince yourself that things will be fine either way
• A better deal could be just around the corner
• So if the other party stalls too long, walk away
• They'll come back around if serious
🔟 Confirm details in writing
Mistake: not confirming details of a verbal agreement
• Always confirm what was agreed to in an email to avoid confusion
• Include next steps and a timeline for both parties
• Play a project manager role to get it over the finish line
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Clay is designed for anyone who values maintaining meaningful relationships. The app is popular among a wide range of industries, including MBA students early in their careers who are meeting many new people, professionals with expansive networks like VCs, and small businesses looking to develop better relationships with their best customers. It’s even used by half the Fortune 500! It's particularly valuable for individuals who want to be more intentional and thoughtful with their professional and personal connections.
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Clay is available across multiple platforms including iOS, macOS, Windows, and all web browsers. Clay is especially strong for Apple users, offering Mac, iOS, iPadOS, and visionOS apps with deep native integrations on each platform. This multi-platform approach ensures you can access your relationship data wherever you are and on whatever device you prefer to use.
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Clay offers many advantages over other personal CRMs. Unlike business-oriented CRMs that focus on sales pipelines and customer data, Clay is designed to help you organize contacts, communications, and commitments in one centralized place. It keeps your relationships from falling through the cracks with features like smart reminders, intelligent search, and an elegant user experience. Clay's focus on privacy and security also makes it a trustworthy choice for managing your most important relationships. Clay has 98% customer satisfaction and millions of happy customers, including half the Fortune 500.
Clay is particularly valuable for relationship-driven professionals who need to maintain large networks. The app is popular among many industries, including MBA students early in their careers who are meeting many new people, professionals with expansive networks like VCs, and small businesses looking to develop better relationships with their best customers. Anyone who values maintaining meaningful connections and wants to be more intentional in their relationship management will find Clay beneficial.
Clay offers competitive pricing in the personal CRM market. Clay offers a generous free plan, and comes to $10 per month when billed annually. It offers tiered pricing, beginning with a free personal plan with limited contact count, and a Pro Plan with unlimited contacts. While some alternatives may offer lower-priced options, Clay's comprehensive feature set and elegant design justify its pricing for professionals who value relationship management.
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