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“5 Things I Wish Someone Told Me Before I Became CEO of TapCap,” With Zachariah Rosenberg

Take extra measures to make those around you feel important — relay a compliment, write a note, ask for advice. As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Zachariah Rosenberg. Zachariah is Founder and CEO of TapCap, the real estate industry’s first fully digital […]

Take extra measures to make those around you feel important — relay a compliment, write a note, ask for advice.


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Zachariah Rosenberg.

Zachariah is Founder and CEO of TapCap, the real estate industry’s first fully digital nationwide multifamily lending company. TapCap thrusts the stale, outdated commercial lending model into the future by introducing a cutting-edge digital approach to the multifamily loan process that is simple, transparent and secure. Through TapCap’s digital platform and multifamily loan app, borrowers have access to real-time and fully transparent financing options at their fingertips.

Prior to founding TapCap, Zachariah was Director of Greystone Labs, an innovation hub that married lending and technology. In that role, he spearheaded the lab designs and crafted technologies that automated loan processes and delivered a more seamless customer experience.

Previously, Zachariah led business development, marketing and app development at start-ups in various industries, including legal and virtual reality.

Zachariah attended the Australian National University and University of Maryland’s Robert H. Smith School of Business. He dropped out to pursue his first start up.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

Myentire family is in multifamily finance, so I grew up with the expectation of joining the industry. The problem is, I didn’t love it — I was a computer geek through and through. I was a terrible student since I was always ditching class — but not to go hang out somewhere. I’d ditch class to study computers in the library. I was just this geeky rebel.

To save some money for a tech startup I wanted to pursue, I took an internship with Greystone on a new project they were working on. This was in 2012 and the bond markets were in a strange position — which left open an interesting arbitrage opportunity involving municipal bonds.

Greystone wanted us to comb through 15,000 municipal bonds, searching for ones that fit this arbitrage play. They expected it would take a team of analysts’ 3 months to go through all of them, working 12 hours, 6 days.

Instead of going through the bonds one by one, I found a way with code to preprogram our evaluation criteria and stream the bond information through the model. Instead of taking ~10,000 aggregate hours for a team to go through the universe of Muni bonds, the algorithm took less than 3 hours.

After handing in the results, I realized one, that was powerful and two, that was exhilarating! I need more of that in my life!

After pursuing several tech startups, I came back to commercial real estate finance. The commercial real estate industry has so much opportunity for us “engineering geeks,” since much of their processes are quite antiquated. I’m now focused on leveraging my zeal for technology and data science to achieve one overarching goal — making multifamily financing efficient, transparent, and accessible to all.

Can you tell us a story about the hard times that you faced when you first started your journey?

This one still stings. Our first client facing app launch at Greystone Labs. We thought we did everything we were supposed to — we interviewed key clients, held focus groups with users and key stakeholders. Everything they tell you to do when designing a product, we did. We had people try out prototypes and sign off that this exact version would supercharge their day. We set an incredibly ambitious release date for just after the new year, so there was zero holiday for the team. But everyone was riding such a high — we were going to be the first of kind and everyone was echoing how they just couldn’t wait to get their hands on the finished product.

We made sure the app’s design was sealed up and functioning perfectly. We were ready for the bandwidth, the traffic, and all of the sweet fanfare. I was nervous, but exuberant. Every kind of thought was rushing through my head when I hit deploy…

And then nothing. No users. No loans. No activity. No one used it. One day went by, one week, one month…

And when the parent company started prodding and pushing for people to start using it, the backlash really hit. “Who were we to tell them how to do their job?” Whereas before my inbox was filled with kind wishes, I now started receiving angry “hate mail.”

How could we have gotten it so wrong?

It still hurts today — but looking back at it, I think my error was really wanting to believe that everything was alright and not seeing the groupthink. No one interviewed wanted to raise their hand, no one wants to be the naysayer. At the same time, we didn’t fully appreciate the incentive structure — we made assumptions that everyone would prefer to be online, but when you look at the incentives, change can feel more like a burden.

I learned that if everyone around the table is nodding their heads, perhaps it’s a sign that you need to take a closer look.

Where did you get the drive to continue even though things were so hard?

This is the problem with innovators — you kind of have to have this irrational perseverance. Perseverance typically has a positive connotation, but in another context, it’s just being stubborn.

If people really were homo-economicus, totally rational individuals, then better ideas might persevere. But that isn’t always reality. People’s habits, opinions, emotions, all get mixed and can create this friction/inertia to new ideas that is difficult to overcome. We often get stuck in “local minima” and it’s hard to push people out of those comfortable spots.

It takes a bit of this irrational perseverance to push people out of this zone (or just really tick them off).

Churchill’s quote comes to mind here:

“Success consists of going from failure to failure without loss of enthusiasm”

So, how are things going today? How did grit and resilience lead to your eventual success?

There are times where you get a chance to pause and reflect — but most of the time I think it always seems like the mountain is ahead of you. Maybe eventual success means summiting, but I’m not so sure — there’s always a higher summit. I think what is meant by eventual success is learning to love the ascent. If you can embrace the ascent, grit and resilience become familiar companions.

And how is it going? I’m still trying to convince myself of the above.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

This was bad. We were developing our email notification system for our loan app, which at the time, had approximately $1 billion in loans being processed — so a handful of current borrowers. As is typical, we built out the new feature in a development “sandbox” which only uses fake data in order to test out the feature.

Somehow this email feature was accidentally briefly connected to our production version, and the terrifying thing about code is how much can happen in a second. The email feature went into a “loop” and sent tens of thousands of these “test” emails to all of our clients in just 2 short seconds.

When I realized that we just super-spammed every client, current and previous I felt this overwhelming desire to burn my phone, delete my email account and set up shop in a nearby forest.

What do you think makes your company stand out? Can you share a story?

I think what makes us stand out is, we aren’t in this commercial real estate finance game because we love it — kind of the opposite. We’re driven by how terrible we’ve found the industry can be.

No one likes bullies, but I really have a strong distaste for them. I think parts of this industry attracts these types, people who profit off of keeping their clients in the dark.

So we’re a company that isn’t just driven on the opportunity of economic profit — there is a more fundamental force driving us. Having a strong mission that goes toward being honest and caring, especially in an industry that is (in theory) cold and calculating certainly makes us stand out.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

I don’t necessarily like this answer, but I have yet to find a more fitting one. This one (paraphrased) from Musk:

“I think it’s very difficult to start companies, it’s quite painful. It’s really, really painful. It’s like eating glass and staring into the abyss. If you are wired to do it, then only do it, but not otherwise. If you need inspiring words, don’t do it.”

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I believe I’m just a sum of all the past interactions I’ve had and there are so many people who have had significant influence on the trajectory.

Certainly so, the individual who has had the greatest impact on my course, without question, is and continues to be my father. That man is the pillar in many, many lives — and he certainly continues to hold up my world.

I believe the biggest lesson I’ve gathered from him is how to scrutinize a concept and break it into its individual components. Many people tend to gloss over the details and just assume that all of the ingredients are necessary or fine. It’s those that take a deeper look, hold each piece and turn it around in their hand, question it and don’t put it down until they understand how it fits, those are the people who can appreciate what is and imagine what could be.

How have you used your success to bring goodness to the world?

I hope in several capacities. As an individual, my family has a practice of giving until the point that the last bit hurts — both with time and money. As a company, we try to go above just being fair and honest and try to be radically transparent. We actively seek to educate our clients on products, even if those products are less profitable to us. I believe it is a corporate responsibility to ensure that clients are well equipped to make educated decisions.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

1. Make sure to understand why a certain practice is in place before seeking to change it.

2. Winning the argument may cost the relationship.

3. Write your plan/hypothesis/theory down. Have another set of eyes review it — we’re our own echo chamber.

4. Do not take too many steps without testing your position. Crave evidence.

5. Take extra measures to make those around you feel important — relay a compliment, write a note, ask for advice.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

There are so many wonderful causes — here’s a simple one. Borrowing from my answer above, make it a goal to make one person every day feel like they were important that day. I think most of the conflicts today in some part stem from people feeling ignored, unwanted, unimportant.

How can our readers follow you on social media?

I’m a bit of a social media hermit, but I do have a LinkedIn (https://www.linkedin.com/in/zrosenberg/) and you can follow TapCap on Facebook (https://www.facebook.com/tapcapCRE/) and LinkedIn (https://www.linkedin.com/company/tapcap/).

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