Jon Brody – CEO and Co-founder of Ladder

Evaluate every decision against the litmus test of whether this helps us achieve our mission, either directly or indirectly, and prune task lists accordingly. It’s critical to invest in decisions that indirectly serve your mission to balance short-term needs with long-term realities.

Jon Brody is the CEO and co-founder of Ladder, a growth solutions company that combines machine learning and a recommendation engine to execute ROI-driven strategy for businesses.

A serial entrepreneur and a former professional poker player with two exits behind him (Velocity Chess and FullGlass), Jon is focused on building the world’s largest data set for performance marketing to remove the guesswork from growth and make ROI-driven strategy accessible to everyone.

Ladder’s technology and services work across every marketing channel and funnel stage to increase ROI when launching and growing businesses.

Where did the idea for Ladder come from?

The idea behind Ladder wasn’t truly new, but it wasn’t being applied much in practice, let alone in an accessible way. As the adage goes, there are two ways to make money: bundling and unbundling to-succeed-in-business-by-bundling-and-unbundling). With the shift to digital — and advanced technologies lowering barriers to entry — marketing has been undergoing a huge unbundling event that’s left the landscape confusing and difficult to navigate.

The success of cross-functional “growth” teams springing up in Silicon Valley was evidence to us that the siloed approach (i.e., having a pay-per-click agency, a retargeting vendor, a conversion rate optimization consultant, social media marketers, etc.) was dying. The right approach became obvious: Bundle all growth channels into one service that’s able to prioritize the right tactics based on expected cost versus benefit. The challenges involved in providing this solution are what led to the technology platform we’ve built, which includes a tactic database, a recommendation engine, a marketing planner, and automated full-funnel reporting.

What does your typical day look like, and how do you make it productive?

I wake up between 7:30 and 8:30 a.m., drink a lot of water, and down vitamins and a protein shake; days can get long and unhealthy, so I try to start out with a solid foundation. My first hour involves sifting through Gmail and Slack and realigning my task lists, if necessary. I’ll then block off time in my calendar to focus on the shortest list of projects or tasks I consider most vital. I get to the office between 9 and 10 a.m. and spend my next hour floating around a bit, checking in on members of the team or diving in and out of projects to throw people an assist and stay abreast. I also try to tackle any small but annoying “need to get done” admin tasks popping up. The rest of my day is a combination of working on high-priority projects as part of a monthly or quarterly plan and reviewing or assisting the efforts of the leaders behind what I view as the four pillars of the company: technology, marketing, sales, and services.

How do you bring ideas to life?

I’ve actually developed an innate dislike for a lot of ideas being floated. There’s a dangerous correlation between the number of ideas a team can generate and the number they actually execute. When I like one of my own or a team member’s, I try to answer these questions ASAP:

If the idea works, what’s the point or actual benefit?
If it does work, would the impact be considered low, medium, or high?
What’s the minimal amount of resources required, and what’s the fastest way to deploy said resources?
If one, two, and three check out, what’s the earliest date we can ship?

Fundamentally, we ship at Ladder, so in our culture, not shipping is the cardinal sin.

What’s one trend that really excites you?

Growth hacking. It wasn’t until the arrival of the internet that the “Mad Men” had enough data to start turning into “Math Men” (and women!). With further advancements in machine learning, beacons, drones, payments, and Internet of Things devices, even offline marketing is only going to get more measurable. At the same time, the rise of growth hacking is turning marketing into an engineering discipline. We feel like we are on the right side of this trend and pushing the envelope on tech and services solutions that embrace it.

What is one habit of yours that makes you more productive as a CEO and co-founder?

Regular exercise. It’s super important to have time each day where you can think strategically about things, unbundled from the dozens of problems, decisions, and mirages that whip your way on an almost daily basis. Exercise refocuses my mind and helps block out noise during the act of exercise itself — and in the aftermath of the workout.

What was the worst job you ever had, and what did you learn from it?

Professional poker player, when I focused temporarily on tournaments. After hundreds of hours of tournament play — and nothing to show for it but a series of soul-wrenching bad breaks — I thought I must be the unluckiest person in the world…until I ran my actual history through probability simulators. I found that, while I had indeed been unlucky, I was just experiencing the equivalent of a mathematical blip of bad variance. I learned that everyone always underestimates “the long run,” and feelings of bad luck are usually rooted in easily corrected naiveté.

If you were to start again, what would you do differently?

True to our nature, we’re obsessed with growth here. So I would have begun building out our own cutting-edge marketing and sales funnels — in particular, our content marketing arm — from the very start. I prioritized too many things early on, when everything seemed so critical.

As a CEO and co-founder, what is the one thing you do over and over and recommend everyone else do?

Evaluate every decision against the litmus test of whether this helps us achieve our mission, either directly or indirectly, and prune task lists accordingly. It’s critical to invest in decisions that indirectly serve your mission to balance short-term needs with long-term realities.

What is one strategy that has helped you grow your business? Please explain how.

Embracing and leveraging the very thing we sell. Too often, I see companies be the worst offenders of the very problems their services or products are solving: design agencies with poorly optimized websites; development studios with webpages not built according to best practices; digital marketing agencies that have never launched a PPC campaign for themselves; and BI companies that struggle with their own reporting. Our commitment to living what we preach was a bet we made that using our methodology and tech truly is the best way to grow and that it works for every type of digital business. Our rapid growth is the result of running tactics from our own database and launching and analyzing marketing tests in the same way we do for our clients. We believe every company needs more growth, and we truly prioritize growth at Ladder — not just in words, but through our actions in the form of drinking the very medicine we’re selling.

What is one failure you had as a CEO and co-founder, and how did you overcome it?

Underestimating how quickly we needed to define a company culture to help employees understand why key decisions are made in pursuit of moving the needle on the future we want to build for ourselves. A strong culture helps new members and positions thrive from day one. Drilling this in during the hiring process itself sets the right tone and expectations for how to be successful at Ladder. Other members of the team shouldn’t have to think about 95 percent of the things I need to make decisions on — but the other 5 percent that really matters to the core of Ladder should be easily relatable and understood by every single person on the team.

What is one business idea that you’re willing to give away to our readers?

I think there’s a big opportunity in attribution. We’re not well-funded enough to pursue this ourselves, but we’d happily pay a lot of money for it (as would any other data-driven marketer). Although marketing is getting more measurable, even the biggest players in the market struggle to make sense of that data in terms of which marketing channels drove what activity on the site. There are advanced machine learning models that the big brands use, but they’re out of reach for small businesses, which don’t have enough data to make those models work. Something simpler and more heuristic would be a great happy medium.

What is the best $100 you recently spent? What and why?

A Blockspring for Enterprise account, which helps us connect apps to Excel. This means we can build pseudo product features around reporting and automation of processes without having to actually write code and bake it into our development cycles. We use Blockspring to build, iterate, and validate that the feature is actually as useful as we thought it would be in the real world.

What software and web services do you use? What do you love about them?

As an agency that works with all types of businesses, we adapt our marketing software stack based on the type of client we’re working for. Generally, we use Unbounce to build quick and premium landing pages; Sumo to install exit-intent modals, email capture bars, and social sharing buttons; and Optimizely to run CRO tests. For analytics purposes, we mostly use Google Analytics, though we’ve started implementing Mode Analytics and Mixpanel. And the backbone that allows us to use all these tools at once is Google Tag Manager, which makes it easy to install tags on our clients’ websites in just a few seconds. Beyond that, it all depends on the goal of the client. For e-commerce clients, for example, we build online stores using Shopify.

What is one book that you recommend the IdeaMensch community should read? Why?

In “Sources of Power: How People Make Decisions”, Gary Klein talks about how people in high-stakes environments (e.g., firefighters, nurses, etc.) actually make decisions. It’s an indictment of the rational, big data-fueled decision-making approach that most economists and business gurus sell as the “right” way to make decisions. Incredibly influential, particularly if you run a small business and need to make decisions with small amounts of data marketing-metrics/).

Which people have influenced your thinking and might be of interest to others?

Bryan Balfour )
Nassim Taleb (


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