September 29, 2021

Asymmetric Advantage: Jason Van der Schyff

Focus, consistency, and imperfections, the list of attributes needed for the leader of a startup to succeed is shorter than you may think. Clear focus will help you stay on track and consistency, mindset, and follow-through is crucial but it’s the ability to forgo perfection when needed that is what separates the prosperous leaders from their peers. The courage to take a risk when the potential payoff is right no matter what others in your shoes would do. This is how your company grows by leaps and bounds. If you want to lead the pack, you have to understand what makes you unique. An asymmetric advantage, business transformation expert, Jason van Der Schyff reveals the mindset you need to make an impact as a startup leader.

This is the Author Hour podcast. I’m your host, Benji Block. Today, I’m honored to be joined by Jason van der Schyff. He is the author of a new book titled, Asymmetric Advantage: How Startup Leaders Can Get Comfortable Being Uncomfortable. Jason, thrilled to have you joining us here on Author Hour today.

Jason van der Schyff: Yeah, pleased to be here with you, Benji. A pleasure.

Benji Block: Awesome! For those that may be unfamiliar with some of your work, Jason, can you give us just a brief overview? Tell us a bit about yourself and your background.

Jason van der Schyff: Yeah, absolutely. I’ve been doing startups for probably the better part of the last decade. I got sick and tired of working inside big companies, being a cog in the machine, and really wanted to do some real value creation. In the process of that, I’ve also done a whole bunch of consulting and mentoring for the other early-stage companies. I really just observed a lot of patterns and thought, “Hey! Wouldn’t this be great to stick in a book?”

Benji Block: That’s awesome. What was your main goal in writing this book and then why was right now the right time?

Jason van der Schyff: It’s an interesting thing to pick up on because I’d originally planned this to be kind of like a workshop, like maybe a subset of lectures that could be given, whether it’s like in a business school or even in a startup environment. And then COVID happened and kind of put a nix on the idea of doing a little traveling roadshow to go and talk to people about. I’ve really gone to, “Hey! Wouldn’t this be great to keep the momentum going while it was sort of fresh in my mind and bubbling around, to put it in a book?” Really, it was just this idea of – a lot of people get overwhelmed by, “Hey! I need to do all of these things in my startup,” to try and stay on track. They read lots of books. It was really about trying to find a niche for the experiences that I had and how I could help those people that are trying to navigate that. Maybe it’s their first startup, maybe it’s their tenth startup. I think it’s still useful information. 

Benji Block: Yes. Speak a little bit more to that. Who are you imagining when you’re writing this book? Who’s your ideal reader?

Jason van der Schyff: Yes. We pitch it up as the startup leader, if you like, whether that’s co-founder, CEO, or something like that. But I think it actually has application really throughout that stack. Maybe you’re a new manager, you’ve been put in a new leadership role— whether that’s actually in a startup or kind of anywhere— and really try to navigate, “all of these new things that I have to deal with”, whether it’s like people, or growing a team, or raising money or having to deal with all of the events that kind of happen in a startup. I really wanted to give the lens of someone who’s kind of in the trenches still. I’m still very actively involved in startups and I wanted to really give that perspective of not– from the same view that I guess you see in a lot of business books, which is either where this is [the person’s] end of career swan song and it’s the culmination of 20 years of experience, which are great. Those books are super helpful, but they sometimes miss the mark of relevance for today.

Then I think the other categories, you got the wildly successful entrepreneur, did one thing, became a unicorn, they cashed out. That’s really kind of in the out-lies theory of what that looks like. This was, “Hey! I’ve not cashed out. I’m still in the fight,” but these are all the things that I’ve seen and learn from both success and failure, and that whole lens of you don’t have to get it right the first time and you have to be able to evolve with the times. Trying to give that perspective in the book, this is very much written in 2021. This is not based on 50-year tenure at General Electric.

The Danger of the Copy-And-Paste Approach

Benji Block: Right. At the top of the book, you talked about how with great intention, business leaders in small to medium-sized companies look at these big tech giants for best practices and they go, “Let’s just take this copy and paste approach.” You see a big-time problem with that and part of that seems to be the inspiration behind the book. Is that right?

Jason van der Schyff: Yeah, absolutely. There’s sort of one example in particular where I was doing a consulting job that I got brought in by their lead investor. They said, “Hey! Can you just give a different perspective to what’s going on here?” I walked in and it was like buzzword bingo. It was, “all we do standups, and we do retros and we have all of these things.” It was all of the learnings from Netflix, and Facebook, and Google, and amazing companies. But they were trying to translate those things that work with a whole lot of structure in those big organizations into like a really unstructured, grungy, gritty startup. I think missing the point that we look at these big companies and it always looks like a swan, right? It’s just calm and kind of moving across the top of the water. 

What you can’t see is that there’s all of this activity furiously happening beneath the surface. That’s true of inside a big company as well. So you go, retros are a great idea, but what you don’t see is the 15 years of battling that those organizations had to get through before they had this great revelation that we should do this activity where we get everyone together. Really, it was trying to bring that lens of, bring your own perspective and your own culture to those activities. Maybe it morally works well. Hey, let’s get the whole team together but you might not be able to do that in a single place and you might not be able to tie that to an activity as if it were in a single place.

I think I use the example where it worked really well while everyone was in the same office in Europe and then they ended up with a group of folks in California. What started off as this; it’s Friday afternoon, we wrap up, we all talk a little bit, everyone maybe opens a couple of drinks. Now, you’ve got half of the team who— it’s 7:30-8:00 AM. Yeah, it doesn’t translate. It’s just about not going copy and paste, “This is a great idea, let’s use it over here.” It’s, “Hey! You’re actually going to have to think about this a little bit more and try to navigate where those things work.” Of course, use all of those things as inspiration. We don’t have to recreate the wheel here, but just be really cognizant of the fact that regardless of what you’re doing, you’re not one of those big companies.

Also, try to remember that if you’re doing a startup, you’re quite likely to be the only person trying to do that for the first time. That is the beauty of startups, is no one has done what you’re doing at that moment in time. It’s just you and your team that try to navigate that. So in a way, you look at what everyone’s doing, but really trying to forge your own path and work at how it does translate into what you’re doing. That was like a big thing for me, I guess, was trying to shine a light on that and say, also, it’s okay if it’s not perfect, right? That’s like a huge pace.

Addressing Universal Pain Points: People, Money, and Experience

Benji Block: Yeah, expecting it to be perfect is going to be a disadvantage in the long run, because it’s going to slow you down significantly if you think your plan needs to be perfect. I think you hit that perfectly in this book; to give people sort of that grace that’s needed to move and to do what’s necessary for your team. In the book, you have three pain points. You talk about how in a business, basically all the problems that we encounter could boil into three categories. You talked about people, money, and experience and how those things could be– you look at them and go, “Man, this is our disadvantage that we have.” How do you turn maybe those disadvantages, speak to those disadvantages into an asymmetric advantage?

Jason van der Schyff: Yeah, great question. I think these are definitely universal pain points of people whether it’s, “we don’t have enough people, we don’t have the right people, we can’t hire the right people.” The thing that’s really interesting for me around companies is that companies are all about people. Yeah, they spit out products, or services, or any of these things, but it really is all about people. Quite often, we try to go and hire folks with very specific resumes, like “I need someone who’s just come out of an Ivy League business school program. Just did computer science at Stanford.” We kind of bias ourselves that way because it’s seen as those people are the most successful. I think really, it was about looking at, “Hey! If you get a good group of people who are motivated, who are smart— they don’t have to have gone to the best schools, they don’t have to have had the education, but you bring them in and you listen to what they have to say.” 

You can actually do really incredible things, and the thing that I’ve seen in my own sort of journey is having people from very different backgrounds come in and do roles that maybe they weren’t experts at. Maybe that’s not actually where their education is, and then letting them apply themselves into the parts of the business where they have a real interest. You just end up with these phenomenal growth stories. I’ve seen it so many times where people come in and they’re just given the opportunity to sort of spread their wings. And what they are able to do when they really believe in the problem you’re trying to solve, or the product or the service and you allow them that freedom to really make it what they want of it. 

They end up being so much better at that job than if you had gone and hired the “expert,” right? Because quite often with expertise, we also introduce bias. We come in and say, “Yeah, but that’s not how everybody else does it.” And, “Yeah, great. What we’re doing, nobody else is doing.” We don’t want to do it like everybody else does. I think that’s like a really interesting lens from a people perspective. I think money is— it’s interesting how companies use money, how they raise money, both good and bad. I see a lot of companies that get a little bit of money— and I think this is particularly true for young founders— if you’re in your early 20s or something like that and you’ve given a couple of million dollars or $5 million from an investment perspective, that’s like a phenomenal amount of money compared to the experiences that you’ve probably had in your life, right? 

Then what ends up happening is, quite often, we forget all of these good budgeting techniques and rules that we tried to learn over time. I use the example of the Aeron chair. Nothing against Aeron chairs, I’m sitting on one right now. But you’ll see startups go and buy $1,400 for everyone in the company. If they went on Craigslist, for example, you get that same chair for pretty much $350. The only difference is, it used to be at someone else’s startup that didn’t work out and they had to sell their chairs.

Benji Block: Probably because they spent too much on chairs.

Jason van der Schyff: Exactly. It’s kind of like, it’s a weird joke that you can play out but you see all over the place and at massive, a vary of scales. Suddenly you get founders who are flying private or flying business class or all of these sorts of things. It was really about trying to draw focus to [the fact] that money is not the reason that we should be doing the startups. It’s the ultimate payback for maybe having to do something for 10 years. That’s a grind where you don’t get remunerated in the same way as everyone else. But again, not looking at big companies and— when they start at say, one of these big tech companies, they’re given a box full of swag and they get like Patagonia vest, and they’re given a brand-new MacBook and $800 to spend on a home office. Those things are all really, really great, but you don’t need to do them at the beginning. You just need to get that initial team of people really believing in what you’re doing. The money sort of comes afterward.

The flipside to that is, people are also taking in way more money way too early in the business than they need to, because they have aspirations of, “We’re going to scale crazy quickly and we’re going to hire 500.” “We need to raise $75 million” when they realistically maybe need to hire hundred people and they could probably do that with $25 million bucks. The difference is, if you show a little bit of restraint, maybe a little bit frugal in the way that you operate the business, you’re generally creating more shareholder value and you’re just wasting less money.

Benji Block: Not even wasting, like there’s an element of creativity that comes in when you know you don’t just have an endless amount of money to spend on everything. 

Jason van der Schyff: Yeah, absolutely. Necessity is the mother of invention, right? It’s that whole idea of being able to look at what you can do without these massive amounts of money. There are great examples of this notion of— it’s probably an old tagline now of capital kills. But you can see how it goes horribly wrong and we don’t need to name and shame people, but there’s plenty of examples wherein recent history, companies have taken in way too much money. They’ve ended up paying almost the ultimate price of having to shut down. I think it happens across the spectrum, right? Really small companies, really big companies.

Then also, the other part of it is, sometimes it’s really hard to get money. Also looking at, if you’re in one of those startups, not judging yourself based on, if the people next door to me in my co-working space just raised X amount of money for this startup. Why can’t I do that? But being able to say, “Actually, maybe this will make my product better because I’ll have to work out how to convince those investors to really come in and participate with me. When they do, they’ll really believe.” 

My experience of that is, an investor who really believes will get you to the end. An investor who just has money and is just trying to diversify their portfolio to satisfy their investors, they’re not going to help you. They’re just trying to cash it on a fashion bandwagon. Sometimes not taking money for a long period of time can actually be really beneficial.

Then to the third pain point of experience, both of those people in and money play into the experience saying – and where you see founders and you see early leaders saying, “Well, I’ve never done this before. I don’t really know what I’m doing. I’m at a huge disadvantage because I’ve never raised money before or I’ve never scaled a team past 10 people,” or whatever it is. Really, what we try to address in the book here was saying, that’s okay. A. this is going to be the best educational experience you’ll ever get, even when you find yourself in a situation that’s really horrible. You’re going to learn so much more than you would have being in a big company or going through a lot of education. And then it will all come together and the piece of it also for people to really understand is, there is no prescriptive formula to all of this. 

It’s this idea of imperfection, right? As long as you focus and as long as you’re consistent, and you don’t get hung up on trying to make it perfect, those are the things that will ultimately get you to the end and make it successful. 

Success is subjective, but just that whole idea of gaining the experience rather than having this desire to have had the experience before you embark on this. The thing that I really wanted to head off and try to get people to dive into the whole process is that I see a number of entrepreneurs who go, “I’ve got this great idea and I want to do it, but I need to go and do my MBA at Stanford first. I need to go and be part of another startup, so then I have credibility and I need to do all of these other bits and pieces.” It was just about saying, you can go and do all of those things, yeah. You can do those things and there’s nothing wrong with that approach, but what’s wrong with just trying to hustle it out? Make this your side hustle. See if you can get it going.

There are so many great examples of stories that have happened like that. The pandemic really brought a focus on that where, suddenly, people had all of this time at home and they actually said, “Hey! You know what? I’m going to do this thing.” For me, this book was that. I’ve spoken about it and almost had to say to myself, why do you keep talking about this? Just go off and do it. 

Turning Your Disadvantage Into An Advantage

Benji Block: That’s great. Yeah, I think it’s so easy to say we want to have an adventurous life even, right? But we’d rather study adventures than actually go on one. How true is that within – even in people’s ideas, and what they could do. It’s so much easier to talk about the idea than actually operate and start doing. I love that idea, focus, consistency, and then imperfection. There’s actually a real level of optimism that you bring to this conversation. It’s very tangible and in the book, it’s very tangible as well. How have you personally grown that mentality in yourself? Do you feel like you were born with some of that or were there some things that you went through that caused you to go, “Okay. What some people may look at as imperfection or my disadvantage is now my advantage”? What started that in you?

Jason van der Schyff: I think the starting point for me was, I never felt like things were bound for me. I never felt as though I was put in a place where I was told, “No, you can’t go and do that.” Even if it was a crazy idea, right? The starting point for me was I had this whole notion of starting the student newspaper. It was a high school thing and I took that from our single school, pretty much went and— I joked that I raised my first money at 16 years old, because I went to a bunch of other schools, met with the headteacher of the schools and said, “Hey! We’re going to do this multi-school newspaper. You need to give me three kids and $2,500 bucks. We’re going to print them and bring them around.” We went to like 14 schools and we signed 10 or 11 of them up, something like that. We ended up with this crazy 45-person editorial staff of 15, 16-year-olds and we made a newspaper. We printed it out on a news press and all of these things. It looked like a real newspaper. 

That was all bound by probably an experience that I have with my parents where they said, “Maybe think a little bit bigger than just the thousand kids that are at your school.” Then also, being in an environment where we definitely had schools that say, “We don’t want to participate.” But no one was sitting there saying, “No, you can’t actually do that.” That was probably the catalyst for me to think like that. 

Then along the way, we’re very much making a view of sometimes stuff works and sometimes stuff doesn’t work, and kind of roll through that process. I moved to the US with two suitcases and no job right and very much pretty optimistic that that would work out. But it was based on, I had a fallback plan and I roughly knew what I wanted to do. Maybe it’s not fair to say I didn’t have a job, but I knew that I was going to start something. That had positive chapters and negative chapters. But in each iteration, looking at it and saying, maybe with some optimism of what could possibly go wrong. But then, even through the down slopes of, these are really tough times being able to take that perspective and look back and go, Yeah, that sucked. I ended up in a lawsuit. That was really horrible, but I learned so much in that 11-month period that I would never have been exposed to in any other way.

Just taking all of those little experiences and saying okay. That’s maybe a little bit of a guiding direction into— you really enjoyed that part of that process. Even if it was a negative process, what’s the more positive side of that? That’s now led to, I take an active role in our business, in what our legals look like, and how we structure the business and how those things work,” which could have been a really horrible experience of being involved in a lawsuit and having to be deposed and all of those types of things. To actually, that’s the type of business that I’m going to be in, not because I’m going to actively seek lawsuits out. But if you run a business, you’re going to end up getting legal letters. You’re going to end up working with lawyers, and accountants, and bankers, and all of these types of things. 

So, how do you then make sure that you’re sort of equipped for all of those experiences, and really turn maybe a lack of formal education in those areas into a different way of thinking? Being able to say, Okay. How do I make these work for me, instead of against me?

Benji Block: That’s good. Fear can often keep us from growth. If someone’s listening to this and they’re going, “Jason, that’s great for you. I’m glad you had these experiences. I would love to get more comfortable being uncomfortable?” Any tips, anything you would say, is a good way to try to just grow the skill?

Jason van der Schyff: I think starting small. It’s not about making these huge quantum shifts in our life, because now we want to go and do something. Like, Hey, I really got to get myself uncomfortable. I’m going to sell all my earthly possessions and go and live in a van. If you want to do that, cool, but it can just be little pieces. It can be about saying, “Hey! I want to get more comfortable speaking to people.” Okay, cool. Maybe that’s just something about upping your game when you’re on a Zoom call or you’re chatting to someone. Maybe explore whether there’s some free training or free videos that you can look on the internet, YouTube, or Udemy or one of these things that say, “I’m going to give you some context on this thing that really sort of bothers you.”

Just try really little things and I think what you end up with is, you start to realize, that thing— that whatever it was— I was fearful of or I felt really disorganized by. I’m just overwhelmed by it. I’m going to try these little bits and pieces and also be able to say, You know what? I can see that that works really well for that person. That doesn’t work well for me, but what else can I try? Through that iteration is back to this idea of not everything you’re going to try is going to be perfect. Try little things and acknowledge when they’re failing and be able to walk away. I think this is one of the things that people sometimes challenge with, which is, no, this has to be the way that it’s done and I’m going to grind out until that converges for me.

I think there’s a lot to say, I need to call it. This is not working. I need to try something else. I need to pivot or I need to go in a different direction. Just doing that and not judging yourself based on my experiences, right? Then have very, very different experiences. I can say that a lot of these activities and my approach to how I look at running a business or helping people in their business is also stuff ten years ago, was super uncomfortable for me. It was really not the type of thing that I wanted to do until it was just actually identifying those things off of, you know what? Actually, I’m pretty good at this piece over here.

When you get that signal of, This is something that I’m good at. It makes me feel good. I think I’m contributing. Then pursue those things. When you feel the things that are sort of roadblocks, be able to say, “Okay. How can I maybe attack this problem from a different direction?”

Benji Block: That’s good. You don’t know until you try. You can read all the books that you want on it or look into the concept, but you got to start. Just dip in your toes in the water of doing things that you’re a little scared to do. I totally agree. I think those small steps are so crucial. That’s great, Jason. Thank you for that. As we start to wrap up here, someone picks up Asymmetric Advantage, they’re reading through it. What’s one to two things you hope that readers take away from this book?

Jason van der Schyff: Focus on what it is that you’re trying to do. Don’t get caught up by all of the noise, which is what other people are raising money for, how other people are running their business. Focus on what it is that you’re doing. Forgo perfection. You’re not going to find it anyway. Even if you think it’s perfect everywhere, it’s not. And really, the mindset to follow through and just keep on that goal that you have until it either works or it doesn’t. And knowing that both outcomes are perfectly acceptable because even if it doesn’t work, you can just roll into the next thing. We get lots of opportunities to do things in life and some of them, even if they don’t work, we can still take a shot at something else.

Benji Block: That’s great. For those that are wanting to connect with you further Jason, what’s some ways to connect with you? Whether that’s online, how can people reach out?

Jason van der Schyff: Yeah. Best place to find me is going to be online, either LinkedIn or Twitter. I’m happy to connect with any readers or anyone that’s interested in general.

Benji Block: Awesome. Well, Jason, it’s been an honor to discuss your book today. Great work. I know it’s a massive undertaking, so congratulations on the release of this book, and hope it helps so many as this resource gets out into the world.

Jason van der Schyff: Pleasure to be here, Benji. Thanks a lot.