Dispatches from the Front Lines: an Interview with Israel Diaz, Founder & CEO of Sunday+Night

This time, we’re speaking with Israel Diaz, Founder and CEO of Sunday+Night. Israel is a 20+ year creative professional and business leader. He started his career as a Designer/Art Director and steadily moved up the ranks to Chief Creative Officer to lead some of the most renowned and awarded Advertising Agencies: Y&R, David&Goliath, Leo Burnett, Lowe Roche, Cossette, GJP and Bozell. Most recently, he was Chief Creative and Design Officer at Jackman Reinvents, a hybrid Management Consulting and Design Firm. In the summer of 2017, Israel launched Sunday+Night – a timely answer to the modern C-Suite dilemma of how to respond to the changing rules of business. In this new world order, success is no longer a case of the big fish eating the small fish, but the fast fish eating the slow fish. 

Sunday+Night believes that organizations rarely die from moving too fast. Specializing in Hyper-Ideation and Innovation Swarms, Sunday+Night partners with committed, action-oriented leaders, teams and organizations to uncover and deliver solutions to compelling business problems in an impossibly fast 16 hours while the competition sleeps. Literally. Powered by a “secret society” of Solutionists – unattainable, highly skilled and divergent thinking free agents – Sunday+Night assembles 3 teams of 5 Solutionists to collaborate and “compete” to deliver actionable solutions to a panel of Client judges. Part Fight Club, part Mission:Impossible, part Black Ops, Sunday+Night fuses the best of art, science, commerce and philosophy. Born in Toronto, Sunday+Night is currently launching in Los Angeles and Berlin with aspirations to expand in major global markets over the next couple years.

Tell us more about Sunday+Night.

Coming out of the agency world, I saw that clients were not getting what they needed from agencies and agencies couldn’t service their clients fast enough because they didn’t have the right kind of people in place. Time and again the agencies I worked for were forced to put the wrong people into the wrong sorts of projects and it caused a lot of confusion. Internally, we knew that was the wrong thing to do, but we had no choice because these were the only people who were available. I noticed the quality of work was going down and the agencies were wondering why they were losing clients. 

At Sunday+Night, we are delivering solutions quickly by matching the right kind of people to the problem we’re trying to solve. Sometimes clients come to agencies asking them to solve a particular problem but no one ever asks whether that’s really the issue that needs solving. We’ve crafted proprietary tools to help us define the problem we’re trying to solve for, including two major workshops that we run with clients. The first one is called “Whystorming” where we diagnose our client’s problem. It’s loosely based off of the 5 Whys model. Once we’ve defined the problem, we go into our “Truthstorming” workshop, which is where we get all the stakeholders aligned on the problem to be solved and to agree on the DNA of the company, the customers we’re going after, the business objectives, what the brand stands for, and what it’s going to be in future. The blueprint that emerges from those two workshops is the most important document we generate because it defines everything and creates a really tight brief for us. 

One of our biggest differentiators is how we actually solution for our clients’ problems. We’re called Sunday+Night for a reason—because we actually do our solutioning on Sundays. We have a secret society we call upon on Sundays because, at that time, everyone’s a free agent. We call these sessions “Sunday Swarms” and they’re usually made up of three teams of five people from different disciplines—lawyers, scientists, engineers, whatever we need. It’s all anonymous—we codename everyone and make sure that no one talks about what they do 9-5, Monday-to-Friday. They solution together and come up with the best idea or ideas they can. We control the entire experience. It’s moderated and facilitated and there’s a lot of play involved. It’s not work, per se. It’s actually a fun way for people to exercise and unleash their creativity in a safe environment. Because we have 16 hours to work with a super-tight brief, and because we have very senior people working together to solve the problem, it’s really easy to come up with many solutions and, as a result, the solutions we get out are very innovative. 

When they’re working together on a problem, is the lawyer, for example, wearing a lawyer hat?

Not necessarily. We ask everyone not to talk about what they do for work. We tell people not to brag about being a CEO or a CFO or anything like that. Once you actually put that label on yourself, people begin to think about you in a certain way. The idea here is to not limit anyone from participating. Of course, people should weigh in with their expertise—that’s what we brought them in for—but respect the fact that there’s going to be people with many different backgrounds and points of view in each Swarm. 

What kind of companies do you typically work with?

When we first started Sunday+Night we went after traditional brands like P&G, big corporations, and companies that we thought needed help. What we’ve found in the year and a half that we’ve been doing this is that we’re actually most effective with start-ups—they’re well-funded and they have money to get things going, but they often need help to define who they are and where they want to go. We work with them to build a really strong foundation so they have a great blueprint to move forward with. When they have that, things begin to happen really quickly. For example, we started working with one particular client and after eight months, everything was set up—their stores, brand, website, you name it, everything was up and running. That couldn’t have happened if they didn’t have the blueprint in place. The clients were involved every step of the way and nothing was a surprise to them. They were happy to see the business grow that quickly and get to market faster. Now, they’re making money faster than their competition. 

This is not your standard business. What gave you the confidence to take the leap?

I’ve always loved creative problem-solving and I saw there was a hole in the market that no one was filling. There are agencies that are very creative-focused, but they ignore the business side of the equation—strategy and ROI etc. Then you have management consulting firms who are very much about strategy, but don’t necessarily respect the output and what that means to consumers. I believed there was a better way to do things, a process in which we create the strategy and the solution and get there even faster.

You were an agency veteran and you moved into the role of an entrepreneur. How was that different for you?

It was huge and scary, obviously. Nothing can really prepare you for it. In the corporate world, you’re typically hired for a particular role and you’re often working with a team but when you start your own business, all of a sudden you’re thrust into a position where you’ve got to figure everything out on your own. It’s a huge learning curve because there’s so much to do and so little time and you feel like your day is going so fast. To be honest, I wasn’t prepared for the angst that came with it. You start to wonder if you can really do this, whether you’re built for this—you start doubting everything. When we start pitching the idea to other people, no one wanted to be the first person to buy because it was so new. That was hard to take because everyone got what we were trying to do and they wanted to be a part of it but because it was so new they didn’t want to take the risk. Everyone wanted to see case studies, they wanted proof, and that was hard in the beginning. 

It all starts with your mindset. I realized early on that this is a mental game

What is the most powerful lesson you’ve learned so far as an entrepreneur?

The most powerful lesson is that it all starts with your mindset. I realized early on that this is a mental game. I was spiralling in the beginning because I got into “do-mode”. I felt like I had to do get everything done and I was getting frustrated with myself because I wasn’t going fast enough. In reality, I was going so fast that I finally had to stop and say “hold on, let me get my shit together mentally first”. I slowed myself down and started meditating and reading all about mindset and different belief systems. That helped me to stabilize how I process everything because it allowed me to feel calmer. From there, I got into a rhythm and pace that was more manageable but I was also seeing better results because I went back to the basics of fixing myself first. if I was to give advice to people starting their own business, I would say figure yourself out first, Understand why you’re doing this and what your purpose is. We tell our clients all the time that you’ve got to go back to your DNA, you’ve got to figure out your purpose, but it’s important to take a second and figure out how you do that for yourself as well. I think doing that work is key. All you have is your mind and without a solid foundation, that’s where people crack. 

I don’t even worry about money now, quite honestly, because I did a lot of work around getting that angst out of me. It was a very limiting belief. As soon as I did that, the first client came and everything started flowing. I wanted to create a company culture and an ethos that doesn’t feel like a trap or somewhere we’re trying to escape. I wanted to create a business that I don’t want to sell.

If I was to give advice to people starting their own business, I would say figure yourself out first, Understand why you’re doing this and what your purpose is.

You mentioned meditation and mindset, is there anything you read that sticks out to you or is there any tool in particular that you use regularly?

I read a few books by Michael A. Singer, The Untethered Soul and The Surrender Experiment, that were about letting go and letting the universe take care of things as much as possible. The less you worry about things, the fewer things eat away at you. It’s something we’ve been incorporating into our practice, especially in dealing with clients. We even start client meetings with meditation. Just recently, we ran our workshops with a client and because they work in a space that has to do with the outdoors, we figured we shouldn’t run them in the city. So we went to a cottage where we could use the outdoors as part of our workshopping. We started the day with yoga, we took meditation breaks, we did breathing exercises, and went for a hike. We actually used the hike as part of the solution for some of our strategic concepts. We use lots of different tools to integrate mind-body-soul into our day-to-day work.

Where did you learn how to meditate?  

I didn’t learn from anywhere specific. I read books on Buddhism and Taoism and I’m a big fan of Alan Watts. You can find great clips on YouTube, but a lot of it is just quieting your mind. The simplest way is to just focus on your breathing or focus on each of your senses, one at a time. It doesn’t take long. If you start your day off with a 15-minute meditation before and do another 15-minutes at the end of the day, it’s enough to quiet your mind so that you can start to listen to yourself. I found that my intuition is heightened in the morning because of meditation and sometimes answers for nagging problems come to me in those sessions because it’s so quiet.

Every entrepreneur has strengths and weaknesses. What parts of running a business do you find the most challenging?

I have a lot of weaknesses. I come from a creative field and even though I was awesome at math in high school, for some reason I’m terrible with numbers now. My eyes glaze over when I look at numbers. My solution was to surround myself with good people that can help with that. I have a great operations person and she’s awesome with all that stuff. I try not to shy away from it, I try to learn it, but I also don’t want to waste valuable time on it if someone else can do it better.

If you could remove one task or responsibility from your day to day what would be?

I like dealing with clients but I don’t like the account management side of things. I’m not an in-the-weeds kind of person so I hire people who are specialists in that area.

What are some of the more specific pain points you experience when it comes to your operations and how do you tackle those?

Staffing is a huge one for us because of how we’ve chosen to structure the business. It’s a very fluid model in that it shrinks and grows depending on what we’re working on. For instance, today we have 10 people working in our six-person office. Sometimes it goes up to 20 and sometimes there are only three people in there. It all depends on the project and what stage we’re at. On top of that, it’s about finding the right people at the time when they’re available. We’re really trying to take advantage of the gig economy and freelancers—there are a lot of amazing freelancers out there. Sometimes you have talent in mind that you want to bring in on certain projects, but the timing doesn’t work. It’s not a perfect model because of the challenges that it imposes from a staffing standpoint, but it’s the most flexible model and clients love it because they’re only paying for people when they need them. Luckily, we’ve had a 90-95% hit rate in terms of getting the timing right. Fingers crossed that continues!

There’s also a challenge around getting the right people together not just from a talent perspective, but from a fit perspective. Being able to align values and belief systems is huge. It took me a while to get the right combination of people together from a personality standpoint because not everyone can work in a start-up scenario. Some people get freaked out because it’s project-based and we may not have this client in two months time. They would prefer a full-time gig with more security. Then there are people that can roll with it really easily. It’s partly finding people with the right attitude and partly aligning with the right belief systems because we’re trying to create a different kind of environment here. 

The greatest enjoyment I’ve had has been around building the culture and making sure it’s something that everyone can get behind. A lot of our philosophy is work, rest, and play in equal measure.

What is the best part of being an entrepreneur for you?

Having control of my time and being able to decide where to invest my energy. Also, the greatest enjoyment I’ve had has been around building the culture and making sure it’s something that everyone can get behind. A lot of our philosophy is work, rest, and play in equal measure. In the morning and the afternoon, we have a 15-minute recess where we tell people to take a break or go for a walk, whatever you like, just get the hell out of here and get some air. Our Head of Design and Wellness lives in Winnipeg but every day at 10 am he leads us in meditation over the phone. He’s also a Reiki Master. We try to practice what we preach to our clients in a big way. It’s helped us a lot because everyone that has worked with us so far has said it’s been their best experience working with an agency because it’s so unlike anything else. Everything gets done, but in a chill way. Everyone feels like they’re contributing to something and it doesn’t feel like anyone’s that stressed out. I’d love to keep that as part of our culture move forward. As we get bigger, it’ll be about protecting that.  

What are some of the tools you rely on to make your job easier?

We talked a lot about mindfulness and self-help and I think those are major tools for any founder. Outside of that, we experiment with a bunch of tools—right now we’re very Slack happy. Because there are so many different people outside of the office working on the same project, we have to find tools that allow us to be in constant communication. Project management tools are also very important—right now we’re using Monday.com.

Keeping our clients up to date with how things are going is getting more complex and we’re starting to outgrow some of our current tools. We’re still in start-up mode and we haven’t had the money to reinvest back into things like our website or sales software. As we get into more retainer-based arrangements with some of our clients, we’re able to budget for the growth of the company and invest in tools and partnerships that will help us be more efficient.

Do you have any favourite books or podcasts?

I mentioned some books already and I listen to random podcasts that are recommended to me by friends, but apart from that, I’m trying not to pollute my brain with other things right now. I’m trying to use my intuition and consciously try to build something different. I don’t know if that’s foolish—maybe in a year I’ll find it was the stupidest thing to do, but we’ll see. As of right now, I think it’s working for us. Everyone’s working to help the company grow but we’re doing in our own way. We’re not actively pitching the business. In the agency world, it was always pitch, pitch, pitch. Every weekend you’re pitching a job and when you win that you move onto the next one. For us, it’s very much about taking care of one client at time really well and seeing how we can grow together from there. 

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Connect with Israel on LinkedIn and learn more about Sunday+Night on their website http://www.sundayandnight.global

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