Steven Bartlett - Harley Finkelstein

1) The Shopify president, Harley Finkelstein discusses how the perception of entrepreneurship being costly and requiring specific knowledge has changed over time. According to him, anyone can start a business now and the cost of failure is as close to zero as it has ever been. The catalysts for starting a business, according to him, are passion and being desperate, not necessarily self-confidence. He also highlights the role of passion in entrepreneurial success, stating that one has to like what they are doing to be able to succeed in the long run.

2) Harley discusses the benefits of therapy for entrepreneurs and the importance of finding the right fit. Finkelstein believes that entrepreneurs need to be self-aware, and therapy can be a hack to get there faster. He states that if you have the means to go to therapy, you should because someone whose job is to make you better is of great help. Finkelstein revealed that his relationship with his therapist has helped him acknowledge the fight and criticisms as a man in the arena but still pursue what he believes in. He also explained that the more successes an entrepreneur has, the easier it is for them to fail as they feel like they've had nine out of ten things successful.

3) Harley shares insights on the topic of failure and the importance of separating oneself as a failure from the project. To by,founder of Shopify, inspired the President with his perspective that failure is an opportunity to learn and discover things that didn't work. As a company, Shopify puts out a lot of products and features, and not all of them may be successful. The President later shared his own experience with taking on a role that wasn't the right fit, but had a hard time admitting it due to ego and insecurity. He eventually learned the importance of self-awareness and now holds a more meaningful role where his storytelling skills shine through.

4) The spiky point refers to the specific area in which you have a passion and in which you excel. Shopify's president says that companies often turn their employees into River Stones by insisting that they have to be better at everything, rather than allowing them to go deep on one thing and be so good at it. He mentions that some people, like Pete, prefer to become excellent senior independent contributors rather than managers. The t-shaped model, where a person can go broad on multiple things but go deep on one thing, is better as it allows employees to find their spiky points.‍

5) Harley discusses the concept of “skill stacking” and how it can help entrepreneurs become more successful. He emphasizes the importance of finding complementary skills that are unique and unobvious to most people, and using them to gain an advantage in entrepreneurship. He suggests that instead of trying to be the best at one thing, entrepreneurs should aim to be in the top 10 of six complementary skills to become the best in a particular industry. Furthermore, he shares his personal experience of going to law school to become a better entrepreneur and highlights the value of critical thinking, negotiating, and writing skills that he acquired from his education.

6) Harley discusses why it is a bad idea to start a company with people who are similar to you and the importance of building partnerships with people who have complementary skill sets. He shares his experience of being a DJ and how he has utilized the skills he learned through that hobby in running a large public company. The President also emphasizes the importance of having hobbies and interests outside of the area that you are building in, which allows you to see the bigger picture and create something unique.

7) Harley shares how his hobby of trying various business ideas has positively influenced his leadership skills. He mentions his experience starting a tea business with David Brailsford called Firebelly and how it helped him understand every feature and functionality of Shopify. Finkelstein advises entrepreneurs to remove expectations of huge success and start small with their hobbies. He explains that the cost of failure is as close to zero as it has ever been, and entrepreneurs can start a business with the price of a Starbucks coffee. Finkelstein also provides examples of successful businesses that started as a hobby.

8) Harley recounts the story of how the company was founded. Tobias Lütke, a German immigrant who moved to Canada to be with the girl he loved, started a snowboard store and wrote a piece of software to sells nowboards since he couldn't afford the expensive options available for selling products online. This software soon became the company's flagship product, Shopify. Though there were already established and capitalized companies in the same space, Shopify's team focused on doing it better and enabling customers to build customized online stores.

9) Harley discusses how the company values their small business customers and aims to make their journey less challenging through the use of software and technology. Even if a small business fails, Shopify hopes to keep them on their platform with the goal of providing a practical approach to every single feature and considering the implications of AI. Shopify is also anti-fragile, inviting challenges and pain in order to come out stronger, and they hope to handle an iconic Supreme flash sale to pull them into a new category of resiliency and performance.

10) The narrative of the early days is examined, and while there is romanticism surrounding the start of a company, the idea of building a company for entrepreneurs, built by entrepreneurs, is compelling. The life cycles of companies and their phases - cult, growth, and enterprise - are discussed, and it is believed that a company’s mission should deeply reflect one’s own life’s mission for maximum engagement.

11) Harley focuses on verticals and give someone a call that I think does a really good job in parenting three or four people. He told you about a mentor that convinced me to go to law school, and another that helped me cultivate a special relationship with my wife. These mentors are not the same people, and I'm able to derive different things from each of them and then create my own version of it. A lot of people call him for advice on parenting, but most people are not interested because they think he's not successful in business or other aspects of life. So he recommends finding different mentors for different aspects of your life and replacing them as you evolve.

12) Jimmy did with Beast Burgers, Feastables, Mr. Beast Mr. Pizza, feasible, and I would definitely put one of those millions of dollars into the hands of a Creator who's on the precipice of figuring out what exactly does my audience like and then creating a better version of that. He thinks someone who does something very nichy, like James Purse, would be a good fit for the three million dollars that you're giving me metaphorically. James Purse makes the most beautiful ping pong table on the planet.

13) Harley looking for people that grab the surfboard, are optimistic, hard working, and have high character. If you find someone like that, you should cherish that anyone who's watching that has found that thing. He diarize everything, and I stick to it. He thinks it's easier for me to prioritize what's important in my life, both professionally and personally, than most people who they try to fit in.

14) Harley thinks it was the pandemic, but he also feltlonely and he wasn't making time. He ended up hiring a lot of people and he was always by myself. He wasn't present for my team or at home, and He didn't replace the time with mentors that I meet in person with virtual coffees. He felt like he was simply trying to tread water and wasn't making time. Shopify has tours of duty, and for the most part, he was doing the same thing up until this most recent one. He finally settled into do what he loves, storytelling, and he thinks he has a much more valuable member of our team.

15) Every time he has ran the experiment of vulnerability, he felt closer to people, and it's like the antidote for loneliness in many respects. And there's another really important thing to say, because we often confuse this idea of being alone with loneliness. Going back to your point earlier, having more people around you on the journey with you, even if they're on their own Journeys but they're sort of tangential to your journey, can make it a little bit less lonely.

16) Every solution, every ounce has a downside. Office centricity has a downside of clear one: If your manager really likes the idea of being in person, you may be in person more often. A lot of companies have gone the opposite way, and the ones that will get it right longer term are the ones that are most introspective about this.

17) Technology is robbing us of community and in-person connection, but the society we live in is optimizing against our innate fundamental maslovian or psychological needs. The reason why diversity is successful and a lot of the things we've done have really worked well is because we created a sense of connection for people. You know everyone, and you know more people than I like. Everyone is working on their own business.

18) Harley says he doesn't think he's a great father, but he wants to be one. He worries that his kids will be too old and it will be too late to be a great father. The mission of what great father looks like is maybe not fitting the great father that you are, potentially. So it goes back to being enough of a father, but I don't know exactly the right path to get there. He has never met someone that says I am a greatfather, but I think I am one because my children are able to be truly independent and I am only as happy as my least happy child.