Collaboration Rule #1: Bet on the Jockey, and Not on the Horse


Tom Nassr is CEO and Cofounder of Checkmate Digital (New Haven, Connecticut),  a design and development agency that works with startups and company subject matter experts to build marketable digital products these startups can use to solve specific problems and generate income. These projects range in size from a single piece of software to complex, integrated systems.


Before working with a company, Tom conducts candid, in-depth validation discussions to determine the likelihood of project success and whether he wants to work with a client:

  1. Is the problem real and not client-specific? (Do other people “feel the pain”?)
  2. What is the client’s background/expertise? Does the client possess the resilience to deal with setbacks and the collaborative and executive decision-making skills to drive the project forward?


Tom knows that projects may morph over time as problems and their desired solutions become better defined . . . and that success more often depends on a CEO’s ability to adapt to these changes, so, Tom says,  “Bet on the jockey, not on the horse.”


Once Tom knows a project is feasible, his team meets with company representatives to explore issues in-depth, refine the objective, flowchart business processes, identify primary and peripheral stakeholders and impacts, and brainstorm strategy. The $5k charge for this “discovery process” recognizes the value of the project design “product,” engages only those clients serious enough to make that expenditure (no tire-kickers), and ensures that, even if the client goes elsewhere to have the work done, Tom’s team gets paid for delivering what can be the most important part of any project . . . a blueprint which, if followed, will ensure the right things get done for the right reasons.  


Tom is excited about the future of Blockchain technology and  notes that Blockchain is not just about cryptocurrency—it has the potential to give users full control, access. and ownership over all of the their content and data . . . instead of “centralizing power in the corporation.” With blockchain technology “Smart Contracts,” the entire contract and its logistical system could be integrated with the application, so that work completed would automatically trigger payment, vastly improving privacy and security.


Tom can be reached by email at, or yon his website at: No .com or .co on the end of that one . . .

ROB: Welcome to the Marketing Agency Leadership Podcast. I’m your host, Rob Kischuk, and I am joined today by Tom Nassr, CEO and Cofounder of Checkmate Digital based in New Haven, Connecticut. Welcome, Tom.


TOM: Hey, how are you doing?


ROB: Hey, good to have you here. Why don’t you start off by telling us a little bit about Checkmate Digital and about what makes Checkmate great?


TOM: Checkmate Digital is a design and development agency in New Haven, Connecticut. We end up working a lot with startups and subject matter experts, and we end up bringing digital expertise to the conversation. These subject matter experts really understand the problems that plague their industry, and then we come in and help them solve those problems with a piece of tech.


ROB: Very cool. That seems like a very interesting and nascent customer segment. How do you find these people, or how do they find you? And perhaps what’s an interesting example of something you’ve been working on lately?


TOM: These people end up finding us in a whole bunch of different ways. More often than not it’s people in our network and people that we’ve known for a while, or a friend of a friend, something like that. We meet them in one scenario or another and then realize there’s this iceberg effect of problems in their own network that they need to solve.


One example of a company that we’re working with right now that’s really solid is an insurance tech company in Hartford. If you didn’t know, about 80% of the insurance industry is done by independent insurance brokers. Those insurance brokers don’t have the type of digital connectivity that a Geico or Progressive would have.


So our client is coming out with an application to give those independent insurance brokers the firepower and digital presence that some of these other bigger insurance companies have.


ROB: Got it. It sounds like you’re building apps and products more than let’s say just a WordPress website build. What’s the range and mix of what you do?


TOM: Absolutely, it’s a lot more product focused. WordPress sites are good on the marketing end of things and able to get content up and out very effectively and very quickly and cheaply, but that’s really not where we sit.


We end up building custom applications from the ground up. We’re writing the first line of code and the last line of code. These are digital products that are the main revenue source for companies. Without this digital product, there is no company. That’s how we operate and why our tagline is “we build digital companies.” It ends up being a piece of software, but more often than not it’s a complex system that helps the startup generate revenue to sustain itself and solve a really specific problem.


ROB: I think one interesting challenge, then, within the business that you’re in is—let  ’s say someone is buying pay-per-click ads on behalf of their client. That’s a very good recurring client, oftentimes whether or not they’re successful in what they’re doing.


Knowing many companies like I do, a lot of times Checkmate could deliver the exact thing that that your client wanted, and they could still be wrong about what the market needed. Then it’s hard for them to be a repeat customer, if they’re wrong about what the market needed and their product may not thrive in the market through no fault of yours.


I may be mischaracterizing; your clients may have all figured it out. But how have you managed to grow well with a client that may have a higher likelihood of dying than a lot of other people’s clients?


TOM: That’s a great question, because it is a pretty delicate space when you’re talking about, “Is this going to be successful or not?” To be able to have those candid conversations with a client is really essential.


We try to weed out as many projects as possible from the beginning. It starts with our process with onboarding—and I have a feeling we’re going to talk about process a lot today. Our process is validating whether or not this is a client that we actually want to work with.


It focuses on two things. The problem that they’re trying to address—is it real? Does it affect other people every day? Can other people outside of our potential client validate that this is a real problem? A hyper-focus on what the problem is and how it manifests in the day to day is key to the first part of “is this customer someone that we want to work with?”


The second part is the person. What is this person’s background? What’s their expertise? Are they collaborative? Can they take critical feedback? These are all things that end up inevitably happening throughout the process, and we want to know from the onset, is this person going to be able to take hard news, make difficult decisions in a timely manner, and be able to move the ball across the goal line here regardless of if we’re going to be working on the project?


So between people and problem, those are the two key aspects that we look at to try to help mitigate the long-term success of these endeavors.


At the end of the day we’re really betting on the jockey. We’re not betting on the horse. We’ve seen products morph and twist and change as we go through the process of talking to users—as any startup does. They morph. It’s not always the same project that you started out with.


The best people, the best CEOs or jockeys or cofounders that we’ve worked with, are able to adapt and move and grow because of that type of adversity.


ROB: I like that about what you’re saying, to bet on the jockey. The companies that I’ve worked in—the ones I haven’t worked at, the ones that have thrived the longest have been the ones where the CEO or the founder has been able to evolve and really sell the vision time and again, both to the team and to investors.


Your validation process sounds potentially quite time-consuming. How do you ensure that that validation process isn’t a big money loser for you?


TOM: A couple ways. I think you’d be surprised at how candid the process is. A lot of times it ends up being a coffee or a beer or a game of pool or something like that—really just connecting with the person behind the company, for the person side of that.


And then the problem side, we turn that into our strategy session. The first thing that we validate is the person, that yes, this is someone that we want to work with. We’ve had several conversations with them, taken them out for dinner or something like that, really gotten to know them as people.


Then, when we’re really trying to analyze the problem, that’s when we’ll have a strategy session. We’ll bring in a handful of members from our team. We’ll charge a flat $5K to dive in deep with the problems that they are articulating, and understanding the industry and all of the tangential players involved and impacted by the problem. We turn that into a whole day strategy session with the client and the client’s team.


Usually after that we have a lot better understanding of what’s going on. That is obviously a very low financial hurdle to begin with, but it really helps weed out who’s serious. They end up walking away with a lot more content that they didn’t know that they needed—things like a specification sheet, user flow or user stories.


These are all things that a client needs to hire a design, development and strategist team to actually build the digital product, and a lot of times they don’t know where to start, but they really understand the problem. That’s what we’re trying to get out of the day.


ROB: I love it. You’ve basically taken this discovery process that needs to happen no matter what—and you were mentioning process. You have turned the discovery process into a product itself that has deliverables that are valuable, whether or not they go with you to actually execute on the project. Is that right?


TOM: Correct. That’s by far the type of attitude that we try to instill, like, whether or not you choose us to begin with, we’re going to try to give you as much value as quickly as possible. That type of attitude and relationship-building we’ve seen to be very fruitful.


We’ve also seen a lot of spontaneous connections happen years down the road. Checkmate is 3-½ years old; we just got a call last week from a client that we were talking to in Year 1, when they had their project and their own set of things going on. We just didn’t line up at the time, but we did a number of things for them and give them a lot of value. Two years later, they raise a couple million bucks and they come back and knock on the door.


So what we’ve found is to give as much value as quickly as possible is the best way to start engaging and building trust, really, between two parties that don’t quite know each other yet. So it’s worked out well.


ROB: That’s exciting, Tom. If we rewind a little bit—you mentioned Year 1—what led you to start Checkmate in the first place?


TOM: [laughs] I had four successful failures, I call them. I define it as successful failures because one led into another, and each one really taught me something interesting about how digital products and teams and startups fundamentally work.


Checkmate Digital and the whole agency model, we decided to go after because we were trying to do it from the individual product level before. Me, a frontend developer, and an incredible interactive digital designer had our own startup ideas for building individual product. We were pursuing those products, and it continually did not work out. We spent quite a bit of money that we had won through college competitions or through business plan competitions and stuff like that, and it just didn’t work out.


The agency side was a desperate last attempt by me and my partners. They actually said to me after we folded up the last company, “Hey, look. If you can find us something to build, we’ll build it. We don’t want to work with anyone else. We just need to get paid at some point, and we need to build some stuff that’s mildly interesting.”


Obviously one website led to another, led to another, led to an app, and then we hired people that are much more talented than I am at these types of digital aspects.


But it really started out with just a desperation to continue to be able to work together as a team. That was really the nucleus of how this thing got started.


ROB: That’s a trend I have seen with many people who want to work on products. They don’t necessarily need to be 100% bought into the product, but they want to work on something interesting, and they want to get paid, and they would like to not worry about the whole thing falling apart.


I think it’s neat that you were able to find—it sounds like these were people you knew—you started off knowing them in school? Is that where you first met your partners?


TOM: Sort of. I met one on Craigslist, I met one at a graduation party, and between the two of them we really put one foot in front of the other and just kept things moving.


ROB: What were you asking for on Craigslist when you found this person you’ve now probably known for a little while?


TOM: [laughs] Yeah, I’ve known him for about 6 years now. Interviewed him on a couch in my house. It’s kind of funny. [laughs] I think the ad was for just a frontend developer.


But I’ve actually had quite good success with Craigslist. I found a techie accountant—no, it was “a tech-minded accountant.” My most successful Craigslist ad, I would have to say, the title was “a versatile human.” That was an attempt to find somebody who would be a Jack or Jane of all trades and would be accompanying me and the management team for some time, doing miscellaneous tasks.


They’ve really found their home here over the last year and really made themselves irreplaceable. It’s funny how it all ends up working out.


ROB: That sounds like someone in the mold of an executive assistant and operations manager, somewhere along those lines?


TOM: Exactly, and that’s the transition she’s going through right now, actually. Going from an executive assistant to an operations manager. Nailed it.


ROB: So she likes checklists, she likes knowing that things are being done the right way. [laughs]


TOM: Yeah. And a broader point, she understands the same definition of “done” that I do, which is very difficult.


ROB: What is done?


TOM: It’s this really soft thing, right? It can’t be put in a box, because these products are continually growing, updating, changing. You could have something that’s done, but what if it has a bug? Or what if the color is a little off, or someone wants to change the way somebody navigates through the application or change the menu item order or whatever?


There’s a million things that could be done at any given point, but at the end of the day shipping is always better than perfect. She understands that and is on the same wavelength as me when it comes to those types of things.


So yeah, it’s been amazing to see that specific growth—and really the transition from being a special education teacher. My background is in philosophy; my CTO went to school for English. People are coming all out of the woodwork in terms of their backgrounds and focus now towards whatever it is they want to actually do.


I’ve found the best combinations of people are diverse backgrounds and diversity of thought and approach when it comes to these types of problems that can be solved with digital.


ROB: Got it. I think that makes a good and sensible transition. What are some things you’ve learned while building Checkmate Digital that you would do differently if you were starting over again?


TOM: That’s a good question. Probably the biggest focus that I would have from the beginning is the use and consistency of tools, a variety of tools. If we started Day 1 with a CRM, we would have a much larger Rolodex because no one would fall through the cracks. So that’s definitely a big one.


Another one is the acknowledgment and acceptance that an agency’s process is the only asset besides the people. That’s the thing that I think we’ve learned the hard way. The process and the way that we approach different problems and address certain circumstances, the process that we have instilled to do that, is so essential. It’s really the most valuable aspect of an agency besides the people working inside of it.


ROB: I think that’s a very neat lesson to take away, because having a process and being able to articulate it the way that it sounds like you have, with this viability report on next steps on the product somebody wants to build, keeps you from being an order taker. You’re not selling hours. You’re not selling something that could be outsourced overseas.


You are selling a product in expertise and you’re selling an outcome. That, from conversations we’ve had, seems to turn out a lot better than trying to just be an order taker.


TOM: Absolutely. That has been the battle from the beginning. “Your hourly rate is what? I can ship it to X location and get it done for half that.” Well, you know what? Not all hourly rates are equal, nor is the number of hours that you’re spending going to be equal.


There’s a qualitative difference here, and when you plug someone into a process versus taking their order—I’ve seen more times than I can count our job becoming “let me help you not hurt yourself.” I’m sure that’s true across any agency, because the sheer number of problems that we see and address on a weekly/monthly/yearly basis is just more than someone approaching one problem. We’ve just seen it more times, so we’re better at it.


That’s the type of thing that I get really excited about and can see moving forward in a really strong way.


ROB: You mentioned tools and CRM. Have you found a CRM that you think is a pretty good fit, and what is it? And what other tools are helping you operate well now?


TOM: I haven’t found a CRM that we’re super happy with. We are shopping, so any of your listeners here, I would love some recommendations for a CRM. I’m trying not to spend a ton of money on it, but of course there’s a ton of value. So any great CRM recommendations, I would love to hear and talk to you about.


But on the general tools side, we do use a number of tools that are essential for our business, one of which I think would probably be unique on this podcast—a thing called Lucidchart. Lucidchart is a flowcharting software that really helps (at least me) map out processes for the business. So not working in the business, but working on the business.


Lucidchart has been essential for seeing all the moving parts and connecting them together. If we’re building a product, how does it actually go through the pipes? That first R&D discovery strategy session process that I talked about a couple of minutes ago, how does that plug into everything else? Lucidchart was the initial piece of software that we laid out that flow into to build the deck around it, to bill around it, to communicate that in an effective way to a prospective client. Lucidchart helps us cut out a lot of fat.


ROB: Very cool. I will mention at this point for the podcast, we have just launched a survey for agency owners who are on the podcast and also listening, asking about what tools are working well for them and what tools they need recommendations on. We just launched that this past week with our previous guest. It’s at


If folks who are listening want to go there and specifically share some CRM recommendations for Tom, that would be a great outcome here today. But in general, we’re just asking about what tools you’re looking for.


In a lot of cases we find that a lot of agencies are looking to partner with other agencies on things that they’re stronger or weaker on. That’s why we put it together. We’re just trying to help the community. We get no kickbacks from anyone we recommend together; we’re just trying to connect people.


TOM: Appreciate that. That’s how this community gets built.


ROB: It’s hard because you don’t always talk to people about this sort of thing when you do talk to them, so we just wanted to create some feedback loops.


I think next quarter we’ll probably do something around lead generation and where people are spending their biz dev time. That seems to be another question that keeps coming up when people are sitting in their own company and not talking to someone else who’s also running an agency.


TOM: On the biz dev side, the best stuff that I’ve seen has been from people that you already know. So often, we just overlook the people already in our own network. There’s a ton of business sitting in your phone or in your LinkedIn right now that just don’t know what you’re doing or don’t know that you can help solve one of the problems they already have.


When I started the company, the first thing I did was I literally called every single contact in my phone that had anything to do with business. I just said, “Hey, this is what I’m doing now. Can I build you a portfolio piece?” [laughs] It was like that.


There’s definitely waves and days that I go through my LinkedIn and I’m like, all right, let’s do an outreach of 20-30 people that I already know, that I’ve already talked to. It’s always easier going back to one of those folks.


ROB: That’s right. A lot of times the best source of business is people you already know and people you’re already working with. Someone I know who I respect a lot, every quarter he’ll go through his LinkedIn and he’ll filter out the people that aren’t really relevant to his business right now, and then he’ll just make sure he pings each of them. If they’re local and his relationship is better, he’ll maybe see about grabbing coffee with them.


It’s really effective. We all too easily forget about who’s in our network. It’s nothing personal; it’s not that they’ve decided that they don’t want to build their product with Checkmate. They just may not have thought about it this week.


TOM: Absolutely. It just takes time and a lot of patience.


ROB: Tom, what are you excited about that’s coming up for Checkmate, or perhaps for marketing and technology in general?


TOM: There’s quite a bit going on in the whole sphere right now. I’m probably going to have to go with a lot of the buzz and the hype around the blockchain stuff.


I’m going to asterisk and caveat that with one really important grounding aspect. To the philosophical level of what the technology actually can do, it’s pretty incredible in terms of shifting power from—you look at companies like Facebook or any of these other companies that have built an entire business off of mining and owning your data. If it’s a free product, you’re the product, as a general rule of thumb.


Blockchain is a technology that, if architected in an application the right way, could give you, the user, full control, access and ownership over all of your own content and data. When we talk about what the world’s going to look like in 50 years—or even double the age of the internet, another 30 years ahead of time—what does the actual landscape look like?


In order for this thing to be sustainable, you’re going to need to own your own stuff. And if you own it, then how do those mechanisms actually work to engage in all of these aspects of commerce, of research, of surfing the internet, whatever?


That’s the thing that I’m really excited about, to actually be building some of these applications that are leveraging blockchain technology to give the power back to the user instead of centralizing power in the corporation.


That’s what I see as really a new frontier, and where the entire industry is going to have to go from a philosophical point of view, and from a logistical point of view if we’re going to start to have these universal systems that everyone in the world has the ability to engage in.


ROB: If people are out there and they’ve heard about blockchain—they may not know what it is, they may know what it is, who knows—if someone’s coming to you with an idea and they’re trying to figure out if blockchain is important to what they’re doing, if it’s viable to what they’re doing, or if they can wait a little bit and should invest in it later on their roadmap of what they’re doing, how do you think through that process?


TOM: That’s a great question. The vast majority of applications should not be on the blockchain, for one. In a huge way, the vast majority are improperly putting blockchain in their roadmap or in their name to try to get funding because it’s hot right now. That’s just kind of disappointing and a total caveat, but I think it should probably be said.


The other thing is that it’s not just cryptocurrency. Cryptocurrency is just one aspect of the blockchain. More like blockchain is a tool and cryptocurrency just happened to be something that you could make with that tool.


If you’re looking at an application of your own and trying to figure out if blockchain should be implemented in your own application in some way, shape or form, a really simple way to think about it is if your application is replacing something in the middle between two parties. There’s a way that trust is needed to be instilled in both parties at the same time.


Blockchain lets you code something called Smart Contracts. If you’ve ever engaged in a contract, it’s, “I’m going to do some work for you and then you’re going to pay me for it.” That’s the very basic contract, right? Blockchain allows that entire contract and that entire logistical system to be put into an application so that when X work gets done, you can prove that X work is done, and those funds can be automatically released because that’s what the entire system is designed to do.


So the Smart Contract aspect of it, being able to automate and trust that an application is going to do what every party agrees that it should do, those are the best types of applications for blockchain. Privacy is involved. It’s very strong cryptographically and from a security standpoint. Blockchain is the best.


ROB: Excellent. Very interesting stuff to think about, Tom. When someone wants to reach you and Checkmate Digital, how should they find you?


TOM: You could reach out either to my email directly, which is, or you could go to No .com or .co or any of that stuff; it’s just Those are the best avenues. Shoot me an email or you can reach out through our website.


But we are going through quite a renovation across the board right now, so it’s going to be great. I’m really excited to release some of the stuff that we have brewing under the surface right now.


ROB: That’s super exciting. Thank you for your time, Tom. Great to get to know more about you and Checkmate Digital.


A special thanks today to Bobby Palmieri of Lilo Social for this introduction. We wouldn’t have great guests without great introductions, so thank you, Bobby. Best wishes to you as well, Tom. Thanks.


TOM: Thank you so much, Rob. I’m super excited to hear about it. Thanks.


ROB: Awesome. Take care.


TOM: Bye.


ROB: Thank you for listening. The Marketing Agency Leadership Podcast is presented by Converge. Converge helps digital marketing agencies and brands automate their reporting so they can be more profitable, accurate, and responsive. To learn more about how Converge can automate your marketing reporting, email, or visit us on the web at

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