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The Graduate: Mark Smukler

“Find the intersection of what you’re passionate about and what you’re good at, find an opportunity that fits that intersection – and then pursue it. And don’t give up.” – Mark Smukler

The Oppy is reconnecting with some prominent NYU Stern alumni with our ‘Graduate’ series. Each month, we’ll interview notable alumni that have made an impact on their community and industry.

This month, The Oppy is featuring Mark Smukler (‘12), CEO and founder of Flow, a location-based app that makes it easy to discover and access the best coworking spaces, gyms, spas, and experiences around you. Mark and I sat down, virtually, to talk about his journey from finance to entrepreneurship, proptech, future of work and the challenges of building a marketplace business.

This interview has been edited for length and clarity.

Provide an overview of your background and your career journey thus far.

My name is Mark Smukler, I am currently the founder and CEO at a company called Flow, which develops an app that makes it easy for individuals to discover and access the best coworking spaces, gyms, spas and experiences around them. Prior to founding Flow, I was the founder and CEO at a real estate technology company called Bixby. At Bixby, we built software that helped property managers of apartment communities streamline their operations and deliver a better resident experience. We founded that business in 2015 and then sold it in 2019 to another real estate technology company called Hello Alfred, where I spent the next two years leading product development. Prior to founding Bixby, I graduated from NYU in 2012 and started my career in finance as an investment banking analyst at a boutique bank in Little Rock, Arkansas called Stephens Inc.. I worked in their New York office covering consumer and retail M&A, and then I did a hard career pivot and became a freelance software engineer. That kicked off my next 10 years as a technology entrepreneur.

Wow, we covered a lot of ground there. It’s pretty fascinating that you went from investment banking to software engineering. Can you provide some more insight into that decision?

When I graduated from Stern I knew that I wanted to run a business one day. I thought finance would be a great place to begin my career and learn how to start, grow and operate a company. Even though I was learning a lot about how to advise businesses on their strategic alternatives like mergers, acquisitions, and raising capital, I wasn’t really learning much about how to operate a business. Knowing that’s what I wanted to do one day, and feeling that the longer I stayed in finance, the harder it would be to leave, I decided to make that jump sooner rather than later. I was fortunate because I had a couple friends that were a little further in their careers and were starting their own businesses. They needed somebody who was young and hungry to help build financial models, do early marketing strategy work, help build out their pitch deck and help them raise money. I raised my hand and said that I could help, but in return I wanted a back seat to see what it was like to start a business from scratch.

I started a one-man consulting company through which I could operate and ended up working mostly with three different companies. I did a bunch of random things, primarily revolving around financial modeling and capital raising. I didn’t know VCs or angel investors but I knew how to build a model and I definitely knew how to build a deck. It was a great experience to dive into the early-stage company journey and see what that was like. During that time I realized that I had a really meaningful skill gap on the technology side of things. I had always been interested in programming and I’d kind of taught myself how to code here and there, but I could never really put all the pieces together.

I knew that no matter what business I would build one day, it would have some technology component. I didn’t necessarily want to be a software engineer, but I wanted to speak the language. I went to one of those web development bootcamps, in my case at General Assembly, and did a three-month immersive program where I learned how to code full stack applications. When I left that program I realized that I still needed a lot of reps. A program like General Assembly does a great job of teaching you a lot of very practical skills necessary to build an application, but you can only learn so much in three months. 

The best way to learn how to code is through projects. I pivoted my little consulting company to a software development agency and I started to bring on clients. Specifically, I worked for real estate companies in New York and I would build really basic websites for them. I found this niche where a lot of the old school second generation, third generation landlords in New York either didn’t have a website or had a really old 1990s Web 1.0 website. Most of them don’t really know very many engineers, and so I built one website and then was referred to other clients. All of a sudden, I became the local New York web developer for real estate owner/operators. 

That’s how I learned about the real estate industry. I started to learn a lot about the inefficiencies. I learned about how it was one of the largest asset classes in the world and the oldest asset class in the world, but a real laggard when it came to the adoption of technology. I created a company called Bixby and built a really simple platform that allowed property managers to communicate with their tenants, process maintenance issues and collect rent payments. Eventually, we added on functionality like reserving amenity space, getting package notifications, and authorizing visitors or unlocking the front door. We scaled that business to about 150,000 apartments across the US and then ended up exiting the business and selling to another VC-backed real estate technology company called Hello Alfred.

Around the same time that I created Bixby, the very first real estate technology focused VC fund launched. Now there are probably over 100 of them. Funding into the sector has grown tremendously over the last decade, into what’s now known as PropTech.

Wow, so it sounds like you just fell into the PropTech world.

I definitely did. I didn’t leave Stern thinking that I would work in real estate; in fact, one of my last courses at Stern was a real estate finance class and I found it really challenging.  At the time, I thought that real estate probably wasn’t something for me, but it’s funny how things turn out sometimes. I ended up getting into the real estate industry, but from a different side of things.

So, after selling Bixby to Alfred, you worked there for a while. Then you decided to leave and start a new business. What led you to that decision?

After selling the business to Alfred, I immediately knew that I wasn’t going to be there forever. After about six years of the grind in investment banking and building Bixby, I very much welcomed being part of a larger business and not always having to take that home with me. I had a great time there. I worked very closely with the CTO at Alfred who was one of the first engineers at Tumblr and a lead engineer at Uber Eats. I’d never really worked with an engineer with that much experience, so I learned a ton about software development and the software development process.

But by this time I’d really caught the entrepreneurial bug and I wanted to continue to build. Before Bixby, I had no idea what I wanted to build and so I was kind of waiting for that thing to hit me again. When Covid hit, I moved to London because Alfred was expanding operations to the UK and I was setting up our office here. I was starting to get an understanding of the landscape and the players, and starting to make our first hires. That’s what brought me to London, but I stayed because I met a girl here. Fast forward 18 months later and I’m still here.

During Covid I found myself thinking a ton about the future of work and its impact on commercial real estate. All that I was thinking about or talking to people about were things like, ‘Do you think people are going to go back to the office? And if not, what does that mean for how consumers will interact with physical spaces? What does that mean for commercial real estate?’ Ultimately, I came to believe that people would go back to the office, but probably not the way that they used to, and that some form of location flexibility and distributed work was going to stick around post pandemic. That represented a pretty meaningful consumer shift in my mind.

I found myself thinking about that way more than I thought about our work at Alfred. That’s when I knew that it was probably time for me to go and pursue the opportunity and that’s when I left to build Flow. Flow is really a solution that embraces flexibility and makes it easier for individuals to find and access the places they need when they want them. For example, every time I flew to London for Alfred I would find I found myself working in cafes and I really had trouble accessing a convenient workspace that wouldn’t require me to sign up for a membership or make some sort of long-term commitment. On the back of remote work policies, I felt that a lot more people, beyond just business travelers, would exhibit that kind of consumer behavior and generate demand for a flexible access solution. I also noticed that coworking spaces and gyms started to offer a more flexible product – whereas before they would only do memberships and maybe, at best, they would do month-to-month contracts, they all started to sell day passes. That was an indication to me that they were seeing consumer demand for that kind of product and trying to accommodate it for the first time. My research revealed that accessing a space to work like a coworking space or exercise at a gym or fitness studio was a pretty broken transaction experience and so I decided to create a marketplace that made it very easy for somebody to find, access, and pay for any nearby space in a very seamless and frictionless way. At this point we’ve been working on the business for about six months. We have about 70 locations across London that we work with. Forty of those are coworking spaces, 20 of them are gyms and 10 of them are spas, as well as hotel pools and amenities. We focus on three core verticals: places to work, places to sweat or exercise, and places to rest or relax. Now we have about 500 users and we’re just trying to keep up with the growth and go from here. Our goal is to get to 1,000 active users here in London and then bring the solution to New York. Hopefully we’ll be in over one hundred of the biggest cities in the world in the next 10 years.

What’s the most challenging thing about building Flow?

Well, they say that things get easier the second time around when you’re building a business, and I’d say that certainly is true in some ways, but it’s still really hard. What’s been most difficult in this business is that as a marketplace, our supply, our location partners are really the product. Flow is just a mechanism for connecting the supply and the demand in a seamless way. If you don’t have great locations that people can go to, there’s no value to the user.

When we started the business the assumption we made was that acquiring these location partners would be really easy, especially coming out of Covid. It hasn’t been tremendously difficult, but it has also taken much longer than we expected. Part of that is it just takes time to get to the right person and communicate the value versus other similar services. What we wanted to do as a marketplaces was to frontload the supply acquisition, so that we could really focus on the user acquisition after. What we have found ourselves doing to a certain extent is juggling both. As we acquire more supply, we acquire more demand, and then we get supply constrained, meaning that we don’t have enough places for our users to go. So we then hustle to acquire more partners. That’s the most challenging.

It sounds like you can’t really avoid juggling the two.

Exactly. It’s the chicken or the egg problem.

Ok, now we are going to move on to the rapid fire questions:

What’s one word that describes you? Ambitious but humble
Favorite professor at Stern? Professor Foudy
First job?  Picking and packing at an electronics factory in Dover, New Jersey
What are you reading right now? Almanack of Naval Ravikant, a book about the founder at AngelList who has a very unique perspective on life and growing businesses
Finish this sentence: At 7am you can find me… running.
What is a cause you’re passionate about? Mental health
What do you do for fun? Play soccer or tennis
What’s your favorite movie, TV show or podcast? Favorite movie, The Big Lebowski
What’s one thing you can’t do that you want to learn? Build applications on blockchain

Ok, just a couple more quick questions before we wrap!

How do you think your time at Stern influenced where you are today?

Stern influenced me by introducing me and also pushing me into the world of finance – but giving me the room to think beyond that industry.

What advice would you give to fellow Sternies who aspire to start their own businesses?

Find the intersection of what you’re passionate about and what you’re good at, find an opportunity that fits that intersection – and then pursue it. And don’t give up.

Wait! One last thing – are you still with the girl?

I am still with the girl. We were dating long distance for about two months and then I moved in with her when I moved out here before Covid. Things moved fast, but we’re still together so it’s working out.

Nice. I felt like it was very important to close the loop on that human interest element. Thanks so much for sharing your story with us, Mark!

Sternies, you can find Mark on LinkedIn or on twitter by following @smukleberry. If you want to learn more about Flow, follow them @flowplaces or visit the company’s website at www.flowplaces.co.

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