August 30, 2026
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It’s been four and a half years since I transitioned from my CEO role at Classy (after 15 years)…
Three years since we sold the company to GoFundMe…
And one and a half since the Classy name was retired (now called GoFundMe Pro).
The other day I ran into someone I hadn’t seen in a while. An old Classy angel investor from back in the day.
“So, what are you up to now?” he asked.
I get this a lot, but never have a great answer.
“A lot of random stuff,” I said.
I walked away thinking that was kind of lame. I wasn’t trying to be cute or anything. My world just looks totally different than it did five years ago. It’s hard to explain. And it does feel random, if not lost at times.
Around 2021, I went through a big mental shift. For the last two decades I had been maniacally focused on one company. That was the right move. And it paid off.
But for the second half of my life I wanted to push myself into new terrain. New companies, new industries, new investments. I wanted to build a portfolio of companies I could contribute to and hold for decades. Some we’d build ourselves. Some we’d invest in heavily. Some we’d take on more of a minor role. This sounded fun to me, and still does, with a few asterisks.
*1 — The biggest gift my dad ever gave Sean and me was presence. He traded what could have been a more lucrative career for never missing a practice. I already took this lesson seriously, but still, I could always be better. Anything I took on moving forward could not screw this up.
*2 — Both sets of parents are still happily married after 45 and 50 years. This feels rare and we both know it doesn’t come cheap. Carrie and I have a lot of things we want to do as a family, and together, once the kids are off to college (holy shit, it’s happening fast!). Classy took priority over family more times than I’d like to admit. That can’t be the case moving forward.
So what am I up to now (in 2026)?
Yes, a lot of random stuff. But this time I want to answer, for real. Maybe you’re interested in the learnings. Maybe there’s even a way to work together.
I won’t do this type of post often. Maybe once a year. But let’s dive in…
* * *
IN 2022, ONE of Classy’s earliest investors, Howard Deshong, asked if I would consider coaching one of his portfolio CEOs. Ben had a service company that was transitioning into SaaS / AI. Right up my alley. I was hesitant though, just to protect my time, but I took it on anyways. It went well. I think I helped Ben (and continue to do so), but oddly enough, the biggest learnings were inward. First, I realized that coaching is a totally different animal than leading a company. Second, I realized I had a lot left to give to other founders.
So I started to write online about my experience leading Classy. I had all but abandoned posting from my personal accounts (even deleting my old Twitter account with over 100k followers, to the absolute horror of my head of PR). So I was essentially starting from scratch in 2023, and let me tell you, it was humbling. I built this big company, so of course people should listen to me, right? Wrong. Holy shit guys, let me tell you, my earliest social media posts were truly cringeworthy.
Around that same time I brought on Jael Johnson to help me not be an idiot on social media. Since then we’ve built a collective audience of over 350,000 people across channels.
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In the beginning I was very focused on writing for social (one quality carousel would take 2-4 hours). These still perform well, even against all the AI slop out there. But nowadays I focus mainly on longer form content — newsletters, website articles, business frameworks. Then Jael cuts them up into shorter-form content (which helps keep me off social media, for the most part – thanks Jael!).
But what to do with all of this content? This is where the idea for Highland came from. That and my CEO coaching gig with Ben. What if I could take all of these lessons and frameworks and turn them into a structured curriculum that other founders could go through. An academy that helped develop you into a top tier CEO. This started with me live teaching every Wednesday morning to a group of ten CEOs, and has since grown into a self-paced program with thousands of students. I still do live teaching too (through our premium track we call Highland Society) and even do annual events at my place in Whitefish. You can visit this link to start the self-paced program, or apply here for the live coaching side of things.
Highland Academy member portal
It’s a tiny team (we added Fletcher Struye after Jael), but I think Highland has massive potential. Over the next year we’ll transform again from a purely educational business to education + product, all in the name of helping founders become better leaders. Our goal is to get this company to $10M in revenue with five or less people. Stay tuned.
* * *
WHEN WE FIRST got to Whitefish in 2020, my high school buddy, Craig McViney, asked me about possibly investing in a project he was working on in the cannabis & hemp space. Craig was a master grower already and things were going recreation legal in Montana. So we did both. The hemp business failed miserably (story for another day), but the upscale Cannabis Counter is still a thriving cash-flowing business. Talk about random. Nonprofit software to cannabis. It’s now entirely run by Craig and his all-star #2, Tony Traina. There’s a lot of dog shit cannabis companies out there. So we try to do the exact opposite, and it seems to be working.
The biggest surprise of the Cannabis Counter story was the birth of Haskill Creek, our wellness store that now sells everything from premium supplements, to skin care, to healthy lifestyle products. At first we had the two concepts wound together, but quickly realized Haskill Creek had its own potential as a separate company. We see it as a healthy alternative to a Walgreens or a CVS.
Interior of Haskill Creek Wellness Boutique in downtown Whitefish, Montana.
In 2023 we made a major bet on a new 3,500-square-foot retail space in downtown Whitefish that brought the business to the brink. Two years later, it’s thriving, complete with a new healthy cafe that serves A+ smoothies, coffee & matcha and a budding food menu. Much of the credit goes to my wife Carrie, and our GM, Colette Stroia, who transformed the experience into what it is today. Stop by if you’re ever visiting Whitefish (we’re next to Markus Foods), and look out for online sales in the future!
The other thing to come out of this journey was Save Farmland, our nonprofit that exists to protect local farmland and food. I can’t remember which came first, the mural on the side of our original store, or our first land purchase. Either way, we bought 40 acres right across the street to protect it from development. This was easily the hastiest decision I’ve ever made.
Save Farmland mural painted on the side of our first store in Whitefish.
Since then, we turned that one purchase into a 501(c)(3) nonprofit, and have been working on the strategy of the organization ever since (truly a circular process). At first we thought incubating new farmers was the way to go. But new farmers don’t grow on trees these days. And there were concerns about flooding the market (from existing farmers). So we pivoted to supporting a handful of amazing local nonprofits that were already working to increase food access to lower-income families and schools. Land to Hand and the North Valley Food Bank are two of them. We now see Save Farmland as a platform for existing programs to expand. Step 1: Purchase or receive donated land. Step 2: Partner with nonprofits to increase healthy food production and education in Flathead Valley.
* * *
AROUND 2024 I started talking to my longtime colleague and friend, Chris Himes, about Highland. The initial idea was to raise a fund to invest in companies in the Highland program – specifically sleepy software companies that could be rebooted with AI. But we soured on the idea when every private equity firm in the country started saying the same thing. So we shifted our thinking towards unsexy service industries.
One day Chris called me up with an idea along these lines. Help property owners manage their insurance. Not as a broker, but when damage actually happens. He had personally gotten screwed by the insurance company on two of his properties in the past. So he hired a little-known specialist in the insurance space called a public adjuster, who refiled his claim and got him what was rightfully owed under the policy.
This idea eventually became JustClaims – a modern public adjusting firm that helps owners and contractors get what’s rightfully theirs under their insurance policy.
The guy who helped Chris out, Taylor Bezek, joined the company as our GM of Public Adjusting and now has a team under him. Then we brought on Omid Borjian (also from Classy) as our founding CTO to build an AI-native platform that maximizes claim handling and outcomes for Taylor and the team. My brother, Sean (another 10+ year vet of Classy), also joined to lead strategy and operations. I not only invested, I helped found the company with Chris, and became a Board Director. We’re under a year old, but the sky’s the limit on this one. I’ll write a separate post sometime in the near future.
* * *
TEN YEARS AGO, when my son Roen was five, we signed him up for ALBION Soccer Club in San Diego. Little did I know at the time that the CEO, Noah Gins, had been using Classy to raise money for ALBION’s foundation (providing scholarships to kids). We finally met and Noah asked if I would be open to advising, and possibly investing behind his goal of building the top youth soccer club in the nation. I said yes. Fast forward to today and ALBION is largely recognized as the #1 youth soccer club in the United States, with hubs in 30+ markets. I remain Noah’s main partner and Board Director of ALBION National. But credit goes to Noah and team. They’ve navigated a very complicated market with high standards and our players at the forefront of everything.
ALBION Leadership Summit | Whitefish, MT 2026
This past June I was honored to host nearly 100 ALBION leaders from around the country at our place in Whitefish. The goal was to get the broader leadership team together, share lessons across the network and align on the future. It was a massive success. The picture above is the barn on our farm that doubles as an event venue. Roen even joined part of it in a full-circle-moment that still gives me chills writing this. But as a die hard Liverpool fan, the highlight for me had to be when Adam from ALBION Dallas (formerly part of the Liverpool academy) sang You’ll Never Walk Alone to everyone at dinner. That also gave me chills.
* * *
A FEW YEARS after starting Classy, I was having a glass of scotch with my father-in-law, Joe (yes, I did drink scotch before my tequila obsession). Joe had a long and successful career at Booz Allen Hamilton before retiring in 2011. He made an investment in Classy around that time, and was thinking about investing in more startups as part of his portfolio. This led to the idea of a small family fund, that he would initially capitalize, but I would run on the side. Over time I could earn a bigger stake as the portfolio succeeded. This was an incredible opportunity he gave me. I’m just glad I didn’t fuck it up.
That doesn’t mean we haven’t had failed investments. That graveyard is heavily populated. But I learned not to expect perfection when you’re angel investing. We were aiming for about 20% to hit. 30% to return capital-ish. 50% to fail outright. Our most successful investments (outside of Classy) have been Ripple, Casetext (acquired for $650M), and of course, ALBION Soccer Club. More recently we’ve made investments in Hubble, Boost, and JustClaims (listed above), bringing our total portfolio to about 15 companies (that are still alive and well).
Tall Timbers is now our family investment vehicle behind several (but not all) of the projects mentioned above. I don’t think we’ll ever be one of those firms doing 20+ investments per year. We’re more methodical these days. We’re either looking for large opportunities where we can invest and be totally passive, or unique opportunities where I can be more involved from an advisory or board perspective (and use Highland as an asset).
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“A lot of random stuff.”
Told ya so. But after writing it all down, maybe it’s a hold-forever portfolio of great companies.
I like that better.
If there’s anything that strikes a chord, feel free to reach out. Or follow the links in each section to explore the projects!
Till next time,
Never say die 🏴☠️
Scot
Every week I tackle management, operations & startup topics that are helping 300,000+ people become better leaders.
Written Weekly by Scot Chisholm
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