I interviewed Scot Chisholm, a four-time founder who built a portfolio of companies worth over a billion dollars. Scot unveils insights from his entrepreneurial journey, which began with selling pizzas. Inspired by his mother's battle with cancer, Scot founded the non-profit fundraising platform Classy, which he sold to GoFundMe in 2022 for over a hundred million dollars. Now, he is focused on building Haskill Creek, a self-care retail business, and coaching CEOs at Highland, his private accelerator.

Would a professional athlete go onto the field and play a game after spending five hours in a bar drinking? No, of course not. They'd be hungover and play like crap. Founders often treat themselves like this, burning the candle at both ends, but are still expected to perform at an A-plus capacity. You need to find balance and take care of yourself if you want to perform at your best. – Scot Chisholm

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Topics we discussed

* How to keep each other accountable when working with friends.

* Scot's journey from selling pizza to building a billion-dollar portfolio.

* Importance of having a strong goal system and operating system in a company.

* Scot's early life, values, and the impact of his mother's cancer.

* The evolution of Classy from a pub crawl event to a SaaS company.

* How to identify and focus on target customers.

* Importance of sticking to the original vision while being open to iteration.

* Pricing strategy in the beginning stages.

* How Scot dealt with limited funds and managed initial hires at Classy.

* Navigating around competitors and their strengths.

* Insight into early competitors and inspirations like Kiva and Movember.

* The significance of hiring the right initial executive team.

* How to have effective 1-on-1s and provide feedback.

* Structuring personal goals and aligning them with company goals.

* Scot's approach to time management and structuring his day.

* Common blind spots among CEOs.

* Managing work-life balance and avoiding burnout.

* How Scot's perspective on life and business has evolved over time.

* Scot's recommended books for every founder.

* How to deal with feedback you don’t agree with.

Insights from Scot

* "You have to be able to separate the business and the performance conversation from the 'let's go get a beer together' conversation." – Scot Chisholm

* "Fundamentally, I think you need a really, really strong goal system and an operating system around the company." – Scot Chisholm

* "You need to figure out what you can specifically be best in the world at." – Scot Chisholm

* "It's the ones that get up and just say, 'Hey, what did we learn here?' and then move to the next round that succeed at the end of the day." – Scot Chisholm

* "Focus is so essential because if you do too many things, you spread yourself thinner and you actually become more fragile." – Scot Chisholm

* "Your values are an embodiment of the characteristics of your team." – Scot Chisholm

* "Price is a tool. You’re never going to win the market just solely based on price. If you and your competitor are priced the same, why would someone choose you? It’s crucial to focus on what makes you different and better. This could be superior customer service, unique features, better user experience, stronger brand reputation, or a deeper understanding of your customers' needs. Price can attract customers, but it’s the added value you offer that will keep them loyal and willing to choose you over the competition." – Scot Chisholm

* "You have to treat yourself more like a professional athlete. It doesn't mean you can't have fun, but you have to factor that in. This is a marathon, not a sprint." – Scot Chisholm

* "It's really important to not come down on them. The dynamic here is I'm your coach. I'm here to help you." – Scot Chisholm

* "Building a leadership team is extraordinarily hard as a founder. When you get it right, it creates just absolute breakthroughs within the organization." – Scot Chisholm

* "Execution is about how you manage and steward the team on a day-to-day basis so that you get the output that you want." – Scot Chisholm

* "I want to work with people that I like, and even if that means a little bit of pain in the accountability department, that's okay with me because you spend all this time with them." – Scot Chisholm

People mentioned

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