Arguing for Both Sides with Daniel Debow

portrait of Daniel Debow
Daniel Debow Daniel Debow is a VP, Product at Shopify. Previously, Daniel was a co-founder of Helpful (acquired by Shopify), Rypple (acquired by Salesforce), and Workbrain (acquired by Infor). Daniel is an angel investor in 85+ companies including Wealthsimple, Clio, Ada, ClearCo, Xanadu, and Ritual. In 2015 he was recognized as Canada’s “Angel Investor of the Year”.

What law school can teach you about being an entrepreneur and founder.

  • You don’t need a degree to be an entrepreneur. It doesn’t have to be instrumental, or a means to an end.  However, the benefit of Business School, is that it provides you a toolkit of how to do a DCF, and what does cost of capital needs, and how different participants work in the business market. Things you can learn online. 
  • It’s a really powerful skill as an entrepreneur to be able to think about both sides of things, equally at the same time. Understand that it’s not about just one answer it’s sometimes about unpacking both sides of it,  really thinking things through.
  • You should start thinking about risk and understanding risk. Risk is not something to run away from, but something to manage. Sometimes you want to take risks because there are these asymmetrical upsides. 
  • The most important lesson that you can get as an entrepreneur as a young person, which is, how to figure out things on your own. Developing the mindset of not needing someone to teach you skillsets.

Building relationships with the decision-makers.

  • The identity process I think just comes naturally if you’re in a space and you’re competing with somebody else. You’re going to see these big companies or adjacent companies, or people you co-sell within deals. 
  • The second thing to think about is how you can add value to that equation,  it might be learning how to co-sell on a deal together. Learning how to build a prototype integration of the technology. The third part about getting to know folks is that you should not feel shy to reach out and ask to get to know them.

What does self-actualization look like in your own personal context?

It’s about having fun and getting to work on fun projects. Getting to learn new things all the time, having a sense of an impact on the world. Creating or inventing new products. There’s something exciting about working on an idea that then becomes a real product or product category that people use in a different way.

It’s also about human beings creating something that other people get to build and grow upon. It’s incredibly self-actualization if you through your actions can help other people.