Serendipitous Moments, Serendipitous Connections

By Erica Ormiston

Missed the latest episode of A New Wave of Entrepreneurship? Listen now.


What if being a generalist could get you ahead? 

Having had various roles, including being the Director of Portfolio Operations at a fast-growing cannabis company, leading a Canadian venture capital firm with investments worldwide, and Director of Strategy and Operations at an agricultural grain marketplace made Mark ( a specialist at growth and a generalist in pretty much every operational aspect of a startup. 

Mark Dhillon, 2016 Fellow Alumni, On Deck Fellow, and Co-Founder Stealth Co, shared his motivations to not pursue engineering after completing a Masters in to do something he was passionate about, his mindset of building, not climbing, how it’s critical to network in the start and tech world and most importantly, how to authentically build those relationships that are going to get ahead. Catch the recap of his conversation with VFC’s Founder and CEO, Scott Stirrett.

Four Thoughts On Growth:

Scott: What do you think are some of the unique skill sets required in an executive in that high growth?

  •  Your education It’s not only about what you learn, but how you learn, how you apply that knowledge and connect the dots between the opportunities. Mark completed his undergraduate degree and thought that he needed to go a bit more niche. After grad school, he realized designing skateparks was ultimately not what he wanted to do. Coming from a family of engineers, he decided to learn more about business through an MBA. From his, MBA Mark was introduced to the tech world, VFC, and the path he is on. 
  • Learn from other people who’ve done it, seen it, and experienced it. One thing Mark hears about in Canada is a lack of people who have, in essence, a high-growth skill set. There’s a shortage of executives who can lead companies; let’s say it’s at 100 million dollar revenue, and they want to be a billion-dollar company. We can look internationally at folks who are doing this to learn how to do it, not just try to go at it alone. 
  • A fundamental thing for every company is attracting and hiring really great people that never stop. Ever. Do this while creating a place that signals is safe for others to learn to be growing, to be vulnerable. Mark thinks that’s where many companies are bad, setting the three or five-year horizon with a culture of vulnerability and experimentation. 
  • Set up a high-level goal for the year that is audacious. It should be a big hairy audacious goal. And from there, it’s like, okay, figure out how you will get there. Think about it cross-functionally, get the votes of the people leading those different charges from marketing to product. From there, see if it is viable. Suppose the goal is viable, cool! Put together and an operational plan and a timeline to see what this makes it looks like.

Four Tips on Community Success 

Scott: Can you describe what is the Operators Guild. And yeah, what are some of the things that you’ve learned from being a part of the community?

  • Figure out how to always be giving back to your community. The Operators Guild is solving how to IPO a company or how to scale like a COO (Chief Operating Officer). This is an invitation-only space for operations leaders. There are approximately 600 or 700 members now across North America.
  • When you want to meet like-minded people, put out the ask. If you’re looking to meet people who are designers because you’re passionate about design, ask to connect and give a reason, “I have no idea what I’m doing, and I’d like to learn from you.” Want to meet a venture capitalist because you want to learn how to fundraise? Put out these asks, and people will actually come to you, and at the same time put yourself out there too. If you find someone being curious, reach out to them for a 15-20 minute coffee.
  • If you don’t have a specific ask, have a beer or a coffee. Mark has seen people ask to network, who feel very uncomfortable, and it doesn’t make sense. He was introverted, and that’s fine, but he figured out that made the most sense to him. And that is, just having genuine conversations. 
  • Don’t base your outreach on credentials. You don’t know people’s stories and how they for there. .Get to know people. Look for friendships. That has been Mark’s compass the entire time. 

Four Pieces of Advice for an Entrepreneurial Start:

Scott: You’re, you’re launching a new venture now, and you worked in venture capital in the past. How is your VC experience helping you in your current entrepreneurial experience?

  • There’s like a quick split. It’s builders versus climber, so you want to be a builder, don’t be a climber. It’s also essential to approach relationships to think about what value you can provide the other person. Be genuine and transparent. 
  • Understand the tactical side and the stress side. Understanding what others have to go through daily is critical. For example, Mark thinks that understanding an investor’s psychology has been helpful for him because he can speak to them on a different level. In contrast, other startups pitch like, “I’m the most important thing in the world. My company is the best thing ever!” You have to find common ground.
  • Understand who you’re talking to and who is in the room. Particularly for investments and raising capital. If you’re talking to an analyst or talking to a principal understand precisely what they want to achieve in their career. Have they hit home runs? if you go on their website, you can see what they invested in, is this you? No need to waste time with the wrong people.
  • Stary Curious. And try being a generalist. There’s so much, and when you think of the matter of knowledge in the world that exists. From odd to inspiring, there’s so much to learn. Take Mark’s dad’s advice: keep learning, keep being curious, and you’ll be fine.

On Mark’s Bookshelf: