Canada's Entrepreneur Podcast Transcript

Introduction

Phil Bliss: Welcome to Canada's Entrepreneur, where we talk to the entrepreneurs who are making it happen across Canada and deliver the news, trends, knowledge and opinions from entrepreneurs and business influences across the country. Hi everyone, I'm Phil Bliss, founder and CEO of Canada's Entrepreneur, coming to you from Toronto today.

Today we're going to be with Dan Swayze, who's a seasoned executive leader with over 20 years of experience driving growth innovation and transformation in high tech companies. He's renowned for executing technical strategies that enable cloud migration, automation and data-driven decision-making. He's very adept at aligning business and technology goals to deliver scalable, secure and high-performing solutions. As a strategic thinker, with a collaborative approach, he has led award-winning engineering teams. He's very passionate about mentoring talent and fostering the culture of innovation. He thrives at the intersection of technology and strategy and drives measurable results and sustained business success. Welcome to Canada's Entrepreneur, Dan.

Dan, great to see you. Why don't we start by you telling us a little bit more about your entrepreneurial experiences? Let's say over the last decade anyway. Why you become an entrepreneur? That's always an important first thing anyway.

Early Entrepreneurial Journey

Dan Swayze: That's a great question, Phil, thanks for asking. I guess to understand that I personally was born with the entrepreneurial spirit. I had it at an early age. I actually as a teenager, I started my first company. From that, I learned a lot of pitfalls. I learned about how to do some business, how to go to market and things like contracting. I didn't understand the corporate side of it. It was just an early education. The sense was I want to work and do something I love. That was what drove me.

Moving forward, transitioning to adult life, I ended up working in corporations to see how that went because I was able to sell the business that I had, made a little bit of money, and then I knew that I didn't have the education. I had to figure out what was next. I got involved with another entrepreneur who was older than me. They were more established in the business world to learn about what it took to be able to do that side of things. That was my first experience in the corporate world. He taught me a lot. It was actually a wonderful mentor. From there, he gave me some guidance into where to go with my journey.

Technical Background and Early Mistakes

Moving forward, I ended up, that's when I started to get my education a little bit more formal. Then I had another role in corporate to get a little bit more experience. I had another great mentor, but then I had these ideas. How do I take these ideas and run with them? Do something with them? As a technical person, because my journey, my skillset was highly technical at the time. I was like, how do I leverage this into something?

Which is a story that I hear a lot these days from entrepreneurs. There's technical people who really say, I've got this great idea. I want to build this product that I just want to take to market. Well, I made all the mistakes that they made, which was like, I didn't even understand what does a go-to-market strategy look like? How do I figure out what I need to bring to the market to align what I'm doing with market need to know that there's actually a need? Things like that. Also, is this patentable? That's an interesting consideration.

First Major Company Launch

In the early 2000s, I actually had launched a company right around the time of 9/11. I had been working with a company who had lost funding because of that. There were some folks who remember that very well. For me, it was kind of an opportunity to say, okay, what am I doing now? I had been working on some side things and it was a CMS content management system. That was novel at the time because I had this idea that people needed to edit their websites.

Then I got in touch with another entrepreneur who had another vision related to email marketing. How the future was going to be email marketing. We were put together by a person who was president of the local ISP and so they were all right, leading technologies at the time. Everything was super exciting back then. We know about the dot-com boom and everything. That was my first experience to actually have a corporation that was actually bringing real product solution to the world. My business partner was handling more of the business end of things and I handled the technical operations. We actually grew that successfully.

Consulting Journey

I had my exit later on and decided I wanted to do consulting. That would have been around about 2011-2012 and that's when I decided let's do some consulting. At that point, I was still along the lines of, okay, I started understanding business a little bit better, pitfalls, technology, and that kind of thing. That consultancy was related to delivery of technical solutions. I still hadn't really gotten my legs on strategy and understanding the go-to-market aspects. That's where I had to develop my business sense during that engagement.

I grew that to a point where I was able to sell that business as well, to another MSP that was acquiring companies in that type of space. Moving forward, I said, "What do I do next?" At that point, I was like, "Do I start another company?" I didn't have any ideas in the hopper and then I actually got involved with another corporation. I had a really interesting proposition. They wanted to bring, they had an amazing engineering team and they were struggling with how to productize their product, which I'm finding actually in my consultancy now, that's another key issue is product alignment with the market to figure out how to position it and get the monetization aligned.

Media Broadcast and EdTech Experience

That was in the media broadcast technology industry. That went extremely well. We were able to scale that to some of the largest media broadcast companies in the world. That was an award-winning team, like technical award-winning team.

I moved from there, finished that engagement and then moved on to another organization that was related to technical delivery for ed tech in the education space. They had similar problems and they needed work related to their portfolio, understanding a lot of things. They had to do an audit with regards to the team and the delivery and the processes and the technology stacks for revenue generating products. There's a lot of work that kind of work, so a realignment.

Current Consulting Practice

Then, I decided that with all of these types of skills, it would make a lot more sense if I would be able to bring this to the world, like to help other entrepreneurs in their journeys, to be able to avoid these pitfalls that I've had over my 30-year career. With that, I partnered with other consultants that have worked for some of the majors, the big three. Now, we've gathered that practice so we can come into an organization that is struggling with that go-to-market, struggling with making sure that their product is being launched in a way that's ROI-positive and structured from a strategy perspective.

Then, with that, we often uncover through discovery that, "Oh, we don't have a product process in place." The technical stack and understanding of how the delivery happens. What's the support structure look like? How does all of this tie back to the monetization of your strategy so that you're able to be profitable, align with your stakeholder interests, as well as perhaps prepare for different rounds of funding. So creating that story is an important element of what we do now.

Advice for Early-Stage Companies

Phil: So really, as an entrepreneur, you've really built your entrepreneurship on two layers. One is actually innovating and building and delivering the product. And the other way is being what I would call the outside guy and doing the same thing, but advising others on how to make some of the steps as successful as possible, is that correct?

Dan: It is one of the key areas that I find companies struggle with, especially early stage post-bootstrap, perhaps at seed or just post-seed funding at those stages. Oftentimes, the founders are like, I've got an idea. I've got something ready for market. I really need to get to growth. And now I've all of a sudden got money. I need to hire some people.

But this is where I would caution. Instead of going directly and hiring, for example, what is called the individual contributor CTO to say, I need to have someone who's going to give me strategy and build my product completely from the ground up. Those are mutually exclusive skill sets, and so, I would caution those folks to consider bringing a specialist from a strategy perspective first, align what your best practices would be, how you would be able to prepare for scale and everything by starting with strategy first, and then making sure you have a good product process in place.

Then, it makes really great sense to have the individual contributors come in to deliver those things. So, you're getting ROI immediately and not having to dilute, for example, through bringing in a new partner or technical partner and things like that. So, it gives you that opportunity to really spend more on moving your business forward, rather than trying to fill a role that you think you need to fill.

AI and Technology Trends

Phil: What have you seen technology has changed in that sort of growth phase companies, from marketing, from a management, from tech side of it, all of those things. What is AI? How has it changed the game for startup, early stage companies?

Dan: Great question. Aside from internal facing tools, which AI can help businesses with streamlining certain aspects of their day to day, as we've all seen with ChatGPT and things like that, when we're considering it from a product side or a revenue-generating side of things, I think it's very important to not say, oh, my app needs to have AI and look at it from that perspective.

It's more of understanding, it's back to the fundamental of the business, regardless of the technology you use, it's all about what problem am I solving, who am I solving it for, and how do I get there, right? Then you determine what technologies would be best to fit that space. Oftentimes, keeping up with trends such as using cloud computing to reduce overhead and costs and doing that in a cloud-native way is an important consideration because that structures and determines the skill sets you need within your organization, as well as what you're responsible for and costs, especially in an early business.

Second part of that, when it comes to AI, it's what value will the AI bring specifically or is my idea completely based on AI and how would I leverage that? So this is the point of consideration of where that fits in the puzzle. VCs are looking for not specifically an AI product or digital product or things like that, they look specifically for, are you leveraging the appropriate modern technologies in your solution that makes sense moving forward, or is it road mapped as part of your solution if it's not an inherent AI type of solution?

Phil: As a consultant advisor, isn't AI working you out of a job?

Dan: I would definitely say it's not working me out of a job. I actually saw a presentation recently from the Nobel Laureate who was a grandfather of AI at U of T recently. At the end of the day, the discussion that followed, the understanding is, AI is definitely not there to the point where it can completely replace us.

What I can definitely tell you that AI is good for is making what they call "a sea of same." By using AI to figure out things like your strategies, will you get marketing strategy, for example, that will work? Sure, but it's going to work and it delivers at a baseline. For anything that's going to be exceptional, that still requires people like you and me who have these years of experience who understand spaces, who can actually apply that creativity, because if you've ever used AI to really try and create something creative, that's where it falls flat. It's really great with processing information, but terrible at novel creativity.

Key Advice for Entrepreneurs

Phil: What advice would you give an entrepreneur thinking about stepping into the entrepreneurial risk environment from where they are in corporate world today?

Dan: Most important advice relates to the first steps you need to do, and that is your market research, understand your unique value proposition for your product, then check to make sure that someone is willing to pay X dollars and figure out how much it's going to cost you to deliver, if it still makes sense, and you're able to raise interest to be able to fund that to get to a proof of concept, that is a great pathway, but only figure out what your minimum is before really investing heavily into something, and if you need help, don't be afraid to ask, there's no shame in asking for help.

Personal Philosophy

Phil: If you had to use one word to describe yourself, what would it be? Why would you choose it?

Dan: I would choose Tenacious, and reason being is because I can tell you definitely in this journey, as an entrepreneur, it's not for the lighthearted or for those who want to give up quickly. You need to be able to get through the times of famine to get to the times of feast and the tenacity and the ability to adjust so that you can roll with the punches, as they say. I think that's one of the key driving factors of why I've been able to succeed in my life. And that's how I describe it, and I would recommend that being an important principle for folks who want to get into business.

Phil: Last question. What's keeping you up at night these days?

Dan: Right now, the main thing that keeps me up is actually excitement. I am super excited about some of the projects that I'm working on to be able to make a difference in their lives, and their journeys and their businesses, because when I meet these founders, it's not just a business transaction. There's that personal relationship that comes there. And as I mentioned, the jelly beans and the trust jar, it's all about that. And you start to form these strong bonds, and really want to see them succeed.

So I don't work with huge companies like a McKinsey or Deloitte or Boston Consulting Group, that kind of thing. I work more with the small to medium enterprise. And so that gives me that blessing and that opportunity to really forge those relationships. And so when working towards a goal to help somebody succeed, that really excites me. So I don't have any major worries that keep me up at night, but it's definitely, I'm just so excited for the next day to come that I can't get to sleep.