Alejandro Dinsmore

Finding ways to live a better life through intentional work.

Founder (raised 2M in funding) | Early-stage Product Manager  (0-11M ARR) | Forbes 30u30 (not in jail)

Newsletter: https://alejandrodinsmore.substack.com/

Product Manager

Founding Product Manager - 1500% increase in Loan Volume in 2023. 

Working on B2C and B2B initiatives across the business.

Claude code’s first birthday event was a great time (well done Anthropic)!

If you work at a company that has fully adopted Claude code then you know it’s hard to understate the impact it’s having across all functions, not just engineering. 

It’s also made work a lot more fun. 

It lets me focus on the things that matter and handles a lot of the monotonous tasks, in way that is simple and addicting.

Hard to believe it’s only been out for a year. Can only imagine where things will be by claude code’s second birthday…

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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

Here's how to create an unstoppable strategy in 3 simple steps:

First, what is a strategy? Most leaders get this wrong. Strategy is not vision. Strategy is not goals. It's the bridge between the two. Strategy is your unique approach to achieve vision. It shapes your annual goals and daily execution. Vision leads to strategy, which leads to goals.

To create an unstoppable strategy, you need three things:

- Unique approach
- Measurable impact
- Target market

I call this "strategic AIM." A stupidly simple, crystal clear description of strategy that anyone can understand.

1. Approach
What's our unique approach to accomplishing the company's 3 to 5 year vision? Why will people choose us? How are we 10x better than the competition? What are 3 to 5 core bets, multi year initiatives, that we will pursue? Your unique approach creates differentiation at all levels.

2. Impact
What does success look like when we achieve our 3 to 5 year vision? How do we measure it and track along the way? Customer impact, financial impact, shareholder impact. Get crystal clear on what success looks like from day 1.

3. Market
Most leaders target anyone that will buy from them. This is the wrong approach. Instead define exactly who your target market is. Think of it like an archery target. Primary is the inner ring, secondary is the 2nd ring, tertiary is the 3rd ring. Dominate the first before prioritizing the second.

Your strategic AIM informs how you set pricing, packaging, and messaging. It also makes annual goal setting a lot easier. What are the company's top three annual priorities that advance our strategic AIM? Pay special attention to your multi year core bets. These help shape annual goals.

Revisit your strategic AIM at least annually. As your vision evolves, your strategic AIM should evolve. They're joined at the hip. You should always have a company wide strategic AIM, but you could also have one for different products or markets as you get bigger.

If you're a founder or operator and you enjoy my content, you should check out Highland Academy: https://lnkd.in/eAVA5ekz

Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland, Just, Haskill Creek

How to create an unstoppable strategy in 3 simple steps:

In 2017 I was called to my lead investor’s office in La Jolla. 

I had no idea what the meeting was about. 

They wanted me out as CEO after nearly ten years running the company. 

I had missed two quarters and lost their confidence. 

That was enough. 

But they weren’t wrong, I wasn’t yet a great CEO. 

While they tried to push me out, I studied the role like a maniac. 

Determined to be better than anyone that could replace me. 

Ultimately, it worked and the company 5x’d in valuation. 

Now I teach everything I learned through Highland Academy. 

If you’re a founder working to become a great CEO, this is for you.

I'll drop a link in the comments if you want to apply.

Or shoot me a dm.

Don't screw up your annual company kick-off!

Most CEOs don't realize how high-stakes their company kick-off really is. They waste the moment. Why? 

Because they don’t realize how high-stakes it is. They think B- work is ok. Check the box. Get back to the “real work”. I mean, you do have lots of shit going on. Carving out a half-day for a company kick off can feel like a waste of time.

I've been on both sides of this. As a founder, I learned the hard way that the leaders who put their heads down and "get back to work" in January are making one of the costliest mistakes of the year. The annual kick-off isn't a distraction from the real work. It IS the real work.

Andy Grove called this "managerial leverage" in High Output Management. The idea is simple: what you put in is nothing compared to what you get out. A few hours of intentional effort in January can shape the behavior of your entire company for months, if not years. Skip it and you put your team at an information disadvantage you'll be fighting all year long.

The truth is, your kick-off is the highest-leverage meeting of the entire year.
Get it right and your team has the clarity to do their best work all year long. Get it wrong, and you're playing catch-up on culture and alignment for months.

I've worked with hundreds of CEOs on this. The ones who treat their kick-off like the Super Bowl moment it is? They never say die. They show up prepared, energetic, and locked in, and their teams follow suit. The ones who phone it in? They spend the rest of the year wondering why nothing is sticking.

I wrote a guide to follow in a recent newsletter. It includes the one thing your team needs from their leader going into the new year: Purpose, Direction & Progress.

link in the comments to go in depth on this topic 👍

How to speak like the top CEOs on the planet:

Most people communicate: 
- nervousness
- indecision
- selfishness

When they should be conveying: 
- conviction
- thoughtfulness
- partnership

Not all CEOs get it either, but the best certainly do. 

Here’s how 👇 

1/ Keep it clear & simple: Avoid jargon. Use plain English. Be yourself. Don’t over-share or talk in circles. Focus on nailing one main point but never exceed three. Don’t assume understanding. Ask the person if they get it.

2/ Speak with energy: Show enthusiasm & belief in what you say. Avoid fidgeting or whispering. Makes you look nervous. Stay solution-oriented. Don’t be a negative Nancy. You’ll demotivate everyone. Use storytelling to inspire & provide tangible examples.

3/ Talk like a partner: Say “we,” not “I”. Stay relatable to every level of the organization. Create a sense of shared ownership. Ask people: “What do you think?” Take people’s feedback seriously. Even if you make the final call.

4/ Communicate the ‘why’: Tie things back to mission & vision. Always explain reasoning behind major decisions. Help people understand company's progress. Create a sense of urgency when you fall behind. Say “because” more to force yourself to provide context to the team.

5/ Control your emotions: Never let feelings override the message. Stay composed under pressure. Don’t over-share and freak everyone out. But don’t sugarcoat things either. Be realistic & communicate a plan.

6/ Ask the right questions: Don’t pretend to have every answer. Find solutions through thoughtful questions. The best CEOs see themselves as detectives. Practice ‘5 whys’ asking why five times to find root causes.

7/ Guide, don’t dictate: Be a facilitator, not a dictator. Orchestrate debate & discussion. Pre-plan exercises that get people collaborating. Keep the room on track and constructive. Shape the discussion, don’t dominate it.


📌 ps if you want me to teach you how to do this at your company, check out Highland Academy: https://lnkd.in/eAVA5ekz

📌 📌 pps. if you enjoy my content, you'll love my free newsletter. Subscribe here: https://lnkd.in/e6ak5dbP

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Helping leaders of all shapes and sizes grow their teams and themselves. 

Every week I tackle management, operations & startup topics that are helping 200,000+ people become better leaders.

Scot’s Newsletter

Highland is a leadership accelerator & community for early-stage founders (seed, series A/B) to develop into world-class CEOs. If you're a founder/CEO, hit me up!

Founder & Chief Professor

A family office with wholly owned businesses, private investments, and property. Ripple, Hubble, FanDuel, CaseText and more.

Managing Director & Founder

After the merger of Classy and GoFundMe, I’ve taken on a strategic advisory role to the CEO & executive team. I remain a large shareholder in GoFundMe and a big believer in our joint vision.

Strategic Advisor, GoFundMe

Haskill Creek is a new type of self-care store. Imagine a healthier & modernized version of a Walgreens or CVS. Family owned business.

Co-Founder

Albion Soccer Club is one of the top youth soccer franchises in the United States with over 10,000 players and hundreds of teams across the country.

Co-Owner

Skills: Agriculture · Food Systems · Board of Directors

Board Member

Save Farmland is a nonprofit organization with a mission to protect and promote small farms in Flathead Valley, Montana, and beyond.

Founder & Chairman

Skills: Nonprofit Technology · Start-ups · Management · Product Management · SaaS · Leadership · Fundraising · Entrepreneurship · Startups · Product Development · Social Entrepreneurship · Software as a Service (SaaS) Founder & Strategic Advisor (Acq. by GoFundMe, 2022)

Founder & Strategic Advisor (Acq. by GoFundMe, 2022)

Classy is a SaaS giving platform that powers the fundraising of over 10,000 nonprofit organizations. Classy is a certified B-Corp, has a team of 300+ people and has raised over $5 billion for social good since 2011. CEO & Founder

CEO & Founder

In Classy’s earliest days, we hosted large scale fundraising events with the goal of connecting millennials with local nonprofits in the San Diego area. CEO & Founder (pre tech company)

CEO & Founder (pre tech company)

Since 1951, The Nature Conservancy has worked to protect the lands and waters on which all life depends. Grounded in science, TNC supports innovation, leadership, and communication for conservation success throughout the world.

Leadership Council Advisory Board

Street Soccer USA is a nonprofit who's mission is to improve health, education, and employment outcomes for the most disadvantaged Americans by using sports to transfer the skills necessary so that they can achieve these outcomes for themselves.

National Board of Directors

Team Rubicon unites the skills and experiences of military veterans with medical professionals to deploy vanguard teams that bridge the gap in disaster response.

For more than 100 years, military, government, and business leaders have turned to Booz Allen Hamilton to solve their most complex problems. As a consulting firm with experts in analytics, digital, engineering, and cyber, Booz Allen helps organizations transform.

Senior Consultant

Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland • Avoid most advice, including my own.

EOS and OKRs broke at scale. 

Here’s what replaced them.

I spent over a decade building Classy from a scrappy idea into a $100M+ company that processed billions in donations before we sold to GoFundMe.

As we scaled, one problem kept surfacing:
No operating system held up past ~$5M in revenue.

We tried OKRs. The product team loved them. But across the company they became too complex. Too many objectives, too many key results, quarterly resets, confusing grading. The system meant to create focus became a recurring distraction.

We looked at EOS. It was cleaner, but too prescriptive. And I didn’t agree with the idea that the founder should hand off operations to a “professional operator.” 

My belief is simple: The CEO must own the operating system.

There was also a deeper issue.

Classy was an impact company. Our mission wasn’t a slogan on a wall. It was the reason people showed up. We needed an operating system that connected purpose all the way down to daily execution, and not just tactical documentation.

So I built one.

It’s called the Northstar OS.

📌ps. If you want to dive into the Northstar OS framework, check out this article I wrote that breaks it down: https://lnkd.in/eDeRw6D2

pps. Sign up for my free newsletter here: https://lnkd.in/gXCsenmP

"Don't worry, you're gonna do great."

I was frozen in the green room at TEDx San Diego. My body felt like 1,000 pounds. I've only been a founder for a couple of years. Why am I giving a TED talk? People are going to laugh me out of this theatre.

An old man in the corner spoke up. That nudge got my legs working again.

I gave my talk. Came back dripping sweat.

"See, I told you you'd do great. You should be proud."

Then he walked on stage to give his own talk.

⁂

Years later, an advisor sent me a book that changed everything about how I manage people.

The One Minute Manager.

I googled the author. Ken Blanchard.

His face stared back at me.

The old man from my TED talk.

Here was one of the most successful business writers of all time, about to give one of his best talks ever, and he was focused on me.

That night I wrote Ken a thank you. He responded with equal grace.

⁂

The book became required reading for every manager at my company. Here are the 3 lessons that changed how I manage people forever:

1/ Great leadership is a side-by-side relationship. Not top-down. It's a partnership. When the organization wins, the people should win. Get this right and your people start managing themselves.

2/ Catch people doing something right. Positive recognition isn't soft, it's smart. People repeat what's recognized.

3/ Correct the behavior, not the person. Address mistakes quickly and specifically. End with reaffirmation. Every 1×1 becomes an opportunity to help people stay on track.

That night, Ken was demonstrating everything he'd later teach me through his book.

True leadership is the smallest acts of support, delivered at the right moment.

Full story + breakdown here: https://lnkd.in/eXTwa8eH

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Scot Chisholm

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The Battle

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Scot Chisholm

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