Healthy Business
May 4, 2022

How To Start A Business And Become An Entrepreneur

Paul Wakim, the Founder and CEO of TwnSqr, shares his journey of starting his business and becoming an entrepreneur.

Paul Wakim, entrepreneur and founder of TwnSqr, joins us on the podcast to discuss what it takes to start your own business and become an entrepreneur. We cover whether you should start a business in the first place, what that looks like if you do, support systems for the process, and what the overall entrepreneur mentality is. Join Paul and I as we discuss his personal journey of starting his own business and how he got into entrepreneurship in the first place.

Paul got started in the real estate industry in 2016 right out of college when he and his then girlfriend Shannon (now wife), started a real estate photography business with a drone that she had bought Paul as a graduation gift. In 2018, Paul taught himself how to code in Python to create an algorithm to predict who was going to sell their home next by identifying people who showed signs of those 5 or 6 common selling traits. Later, he met his great friend and TwnSqr co-founder, Mitch Tracy while rock climbing. In mid 2019 Mitch quit his job to come work on TwnSqr full-time to refine and drastically improve the algorithm.







The decision and process of whether or not to start a business and how to do it are some of the most pressing questions entrepreneurs face. Everyone wants financial freedom. And one of the easiest ways to achieve that is by starting your own business. Join Paul Wakim and me as we discuss his journey of starting his own business to become an entrepreneur, and his current project, TwnSqr.

How To Start A Business And Become An Entrepreneur

In this episode, I have Paul Wakim on the show with me. Paul is from the real estate industry. He got into it around 2016 with his wife, Shannon. They started in the real estate photography business and built up this amazing photography business but now have a startup called TwnSqr. He's helping real estate investors sell their properties with their software.

Paul dives into the good and the bad of the startup industry, what he, his wife, and his partner, Mitch have all gone through. Also, pivoting and trying to figure out what's working and what's not working. He dives into the hardships of building a startup and the successes that he's had as well. He and his wife are traveling to Airbnb all over the nation, trying to figure out where they want to land and live. He has been in Oregon and he's going to Lake Tahoe. He has a very interesting life. He's a young guy. He has this startup, TwnSqr, which is going well for real estate investors. It's a great tool for your tool belt.

Before I introduce you to Paul Wakim, I want to share that we are busy behind the scenes developing the community of Iron Deep. We're developing the retreats for 2023. We're going to be doing two Men's Awakening Retreats. We're figuring out what the locations are on those. We're going to be doing a Soulmate Retreat. You want to check that out here soon. It's going to be in Palm Springs, California. We're also going to be doing a homecoming for the men that have already been to an awakening. We're going to come home again at our Men's Homecoming in 2023.

Go to our YouTube channel and check out these episode videos and our videos that come out each month about something to do with the men, faith work, our passions, our legacy, and our purpose. Check that out on our YouTube channel, Iron Deep. I want to introduce you guys to Paul Wakim.


In this episode, we got Paul Wakim with us. What's going on, Paul?

Not much, Brett. Thanks for having me. I'm excited to be talking to you. It's been a long time coming.

I'm looking forward to this interview. You're a very unique person. Reading over your journey, you and your wife are doing your business TwnSqr remotely, staying in different Airbnb. Not just any type of Airbnb but you're staying in cool places. You guys are in Oregon. You're getting ready to go to Lake Tahoe. That's awesome.

We’re chasing the mountains. Thank you. We're trying to chase the beauty that the Americas have to offer.

I can't wait to dig into that. I love talking about these unique types of passions and your life as an entrepreneur. Let's start this. Who is Paul Wakim?

I graduated from the University of Pittsburgh in 2016. Before I went to college, while I was in high school, my entire life, I was an aspiring entrepreneur. I started a landscaping business. In college, I bought and sold sneakers. I'll never forget the story that I got a pair of sneakers that a guy offered me in person. He was going to buy them for $12,000 if you can believe that. It was a $250 pair of sneakers. I showed up to the meetup in a public place. He offered me his Cadillac CTS that he drove up in instead of the $12,000 in the middle of Oakland, a little city outside of Pittsburgh where the University of Pittsburgh is. I've always been entrepreneurial.

You had these sneakers that you’re trying to sell and he gave you a car for your sneakers.

He tried to. I said, “No deal. I don't want your 120,000-mile Cadillac CTS in a back alley.” It's always one I like to tell. We bought the sneakers. We got lucky that we got them for $250 and then met that guy. I say we, my friend and I. We went in together on them. We ended up selling them on eBay for something crazy, like $10,000. It was a whole game we were involved in. I've always been chasing the entrepreneurial spirit that I have inside of me.

When I graduated college, my girlfriend at the time, now my wife, her name is Shannon, bought me a drone. I used that drone as a hobby for a couple of weeks. We decided, “Let's try and take some real estate photos.” A friend of ours who we were also in business with at the time doing some social media marketing said, “My wife is a real estate agent. Can you take aerial photos with your drone?” Drones were becoming a hot thing in 2016. I said, “Sure. I'll give it a shot.”

We went out, took some photos of a listing that she had, and the rest was history. I drove down the street and met another real estate agent who happened to be one of the largest real estate agents in the Pittsburgh, Pennsylvania market. We've grown a full-service real estate photography and real estate media business into one of the largest real estate photography companies on the East Coast based in Pittsburgh.

My wife runs that company. That's how I cut my teeth in the real estate industry. That's where I got my start and exposure to high-level agents and investors mainly. I then got interested in real estate. That's how I got my start in the world of real business, talking to accountants, not selling sneakers in a back alley for a Cadillac CTS.

We have very similar stories. You're a lot younger than me. When you said eBay, it brought me back because that's how I first started. I get introduced to entrepreneurship through eBay, buying and selling whatever I could get my hands on, and going to thrift stores, whether it's stereos or equipment. We used to buy and sell DVDs on eBay back when people bought DVDs in my day.

Time flies. It wasn't that long ago. It's crazy but I love it. I have a lot of real estate investors on this show because I'm in real estate. I love it because you have found the niche that's not necessarily flipping houses or buying rental properties but servicing real estate investors and real estate agents. With photography, you found a niche.

You had this drone. What does that look like? You take these very high professional pictures and taught yourself how to do that. That's a pretty big deal when you're scrolling through real estate listings. The pictures speak louder. You're staying in Airbnb and it's funny how I'll scroll through Airbnb. If something doesn't have good pictures, it's like, “This place is pretty crappy,” but it might not be.

At the time in 2015 and 2016, a lot of agents were taking photos with their cell phones because cell phones were getting better cameras. It has always been a little bit of a challenge to convince people sometimes that they do need photos from a professional camera. That first house that I ever took photos of with the drone, I drove down the street and met that real estate agent, who happened to be one of the biggest in Pennsylvania. She said, “I want you to take aerial photos with your drone and interior photos. You have a camera. You're a professional photographer?” I said, “Yes, I am.”

I got in my car. I called a photographer friend of mine. I'll never forget it. I met him for a beer and said, “I need to borrow your widest-angle lens possible because I need to make a real estate interior portfolio.” The next day after that, I got his lens. I went out and took photos of my friends who had nice houses. I took photos of their houses, the worst real estate photos possible. I took those Airbnb pictures you're talking about. I put together a portfolio and showed it to this agent. She said, “Sure.”

In that year, we photographed 450 listings for her and she referred us to everybody. Everything has taken off word of mouth since then. To say that I got lucky is an understatement. There’s a lot of hard work in there. To walk down the street and stumble upon the biggest agent in Pennsylvania at the time is nothing else but luck.

You put the puzzle together. It's like, “She needed something.” You're like, “I don't have that but I know someone who does.” It was that wide-angle lens, which is honestly what I used to use. I remember when I used to be the one taking pictures of my vacant houses. I put the wide-angle and the flash on. They wouldn't be that good but they'd be better than everybody else's.

Technology has changed so much since then. We are photographers if you can believe it. Whenever the photographer takes a photo of a kitchen, they set their tripod down. At the time, I was taking photos with my hands on this crappy $100 camera. The lens was a $800 lens at the time. Nonetheless, our photographers now, for every composition of a kitchen, take four photos. 1 that has a flash and then 3 that are of varying exposure levels. Our editors blend all of those together to make a final image that is then edited. If you see good photos, it's because somebody's taking a lot of time to doctor up that image and give you the sense that you're in the room with all that crazy editing.

IDP 100 | Become An Entrepreneur
Become An Entrepreneur: If you see good photos, it's because somebody's taking a lot of time to doctor up that image and give you the sense that you're in the room with all that crazy editing.

People are doing a lot of 3D images. I'll go on Airbnb and I can walk through the house. That technology, which used to be expensive, is coming to the surface. It isn't as expensive as it used to be. You took this and ran with it. Luck was involved but you've been in the entrepreneurial world for several years.

You have this new organization, TwnSqr. We're always looking for who can we help build our team as a real estate investor. It doesn't always have to be someone we're hiring directly or an employee or a contractor. I'm looking for other services that we can put into our team, whether it's an insurance company that can insure all of our properties or another software that helps us be more productive, or whether it's TwnSqr, which can help us sell our properties. Can you dive into that? How did that get started? Tell us about TwnSqr a little bit.

I learned a lot from the professional real estate agents and professional real estate investors that I was taking photos for. I was the only photographer for the first 2.5 years taking photos of up to 12 houses in a single day. Lots of them were flips. We had a fast turnaround. You know how investors can be like, “I need photos now so I can put it on the market tomorrow.” Agents are the same way sometimes. We got a name for ourselves because we were able to turn around the photos quickly.

I had this amazing epiphany in 2018 and 2019 that there is no real estate without a seller. I thought, “If I could predict who was going to sell their house next with technology, then I could fuel my real estate investments,” which I was getting into at the time. “I could fuel my colleagues and real estate agent careers.” I looked at things like ListSource and MLS. At the time, there was a lot of well-structured data in Allegheny County around Pittsburgh, Pennsylvania provided by Carnegie Mellon University and the county.

With all of that data, I said, “I know why people sell their houses.” I talked to homeowners all day long. “I can build an algorithm to predict who's going to sell their house next.” In late 2018 or early 2019, I started learning how to code in Python early in the morning. I hired a coach overseas on Upwork to tell me how to write code and build this very rudimentary, essentially list-stacking algorithm to predict who was going to sell their house.

Through some mutual friends, I was rock climbing and met my co-founder, Mitch. I said, “Mitch, look at this cool thing I'm building.” He said, “That's not an algorithm. That's some crappy Python code.” TwnSqr, as it exists, was built out of Mitch and I becoming friends, rock climbing. At the time we were watching A Game of Thrones. We bonded over that. Mitch ended up quitting his job and building a better version of that algorithm. There's a whole story behind that that we can go into but it all started with me wanting to learn how to code so I can improve my real estate businesses and predict who was going to sell their house next.

We're always trying to figure out who we're going to market to and who needs to sell their house fast so we can help them with their problem. TwnSqr is built. You have this algorithm. You started this way but TwnSqr has transformed into more of a software and a website that we, real estate investors or wholesalers, can use to sell our properties.

We built that prediction algorithm. It was accurate, much to the credit of the CMU undergrads that were structuring the data for us to use. They didn't know that we were using it but we built that algorithm. It was 95% accurate or something crazy like that a couple of weeks before COVID hit. When COVID hit, we realized, “The data isn't going to work for us to predict who's going to sell.”

We had our first pivot in 2020, right as COVID was hitting and right as the business became remote, which is where I am, traveling around and trying to figure out where I want to live. We decided to pivot and help retail sellers, people that wanted to sell on the market with real estate agents. We decided to help them connect with top real estate agents. We did that for about a year or so based on the core technology of a marketplace.

Much to real estate agents’ credit, everybody has a good real estate agent. The homeowners didn't want to work with a software platform to find a real estate agent because they already had a good agent in their pocket. We pivoted back to our real estate investing world in Halloween of 2021. Pivots are not fun. Pivots are brutally difficult. We can talk more about that if we want to. We have been doing TwnSqr as it is for real estate investors to support their businesses and build tools for their businesses after all those different pivots and trying to figure out how to be tech startup entrepreneurs.

What are some of the tools that you provide for investors?

You can think of TwnSqr as that marketplace. It's the core technology we built in late 2020. That core technology is a marketplace. We decided to build tools on top of that marketplace for real estate investors. Everybody in the real estate investing space market the properties that they have for sale, usually through email, text message, and word of mouth like phone calls to their buyer's list.

There's no technology that has been built that is specifically for real estate investors on the email side. We've decided to, on top of that marketplace, build some high-quality email texts so that whenever you have a property for sale, you post it to the marketplace on TwnSqr and then you can use our email technology to send that deal or that post as we call it out to your buyers. The jewel in our crown at TwnSqr is that after you send it to the marketplace and you send your deal to your buyers, you can take that same post and find another investor.

This is a super important thing to me, the connection between investors. How I've been able to become successful is connecting with more professional people. On TwnSqr, you can take your post and then find another investor in your market, connect with them, and ask them, “Can we work together? Can we joint venture on this property? Can I leverage the buyers, that you have that I don't, to market this property?” It all happens in the real world, as you know, Brett.

IDP 100 | Become An Entrepreneur
Become An Entrepreneur: How I've been able to become successful is connecting with more professional people.

I'm sure you guys have people come to you all the time that want to joint venture with you because you're a formidable company in the Indianapolis markets but it's never been done online correctly. That's what we allow users to do, market their deals to the marketplace, send their deals to their buyers, and then connect with other investors in their market to sell their deals to those other users, buyers, or contacts. That's called post-sharing. It's the thing that we're most excited about with TwnSqr.

We have a lot of real estate investors following this show. I would encourage you to have more tools that you can have to help out our business. TwnSqr is a great tool to help, especially with some of the shakiness and shiftiness in the market, and having that extra tool to help sell the properties. It used to be easy to sell properties but it's starting to become a little bit more difficult. Getting more tools on the dispositions is super important.

I want to shift this up a little bit and ask about your experience. Everyone who's probably read this has had that experience with a tech startup. You've mentioned a couple of pivots in that. What your experience has been like with a startup industry and going through some of that? You're raising capital and trying to figure out what are we, who are we, and what are we doing. Talk to us about the first couple of years of this.

It has been a wild ride, to say the least. Mitch, my cofounder, and I decided that we were going to go down this path of being a true tech startup, whatever that exactly means but we defined it as raising money, talking to venture capital firms, talking to family offices, and selling large pieces of equity in the business to achieve hypergrowth. It is how I would classify a traditional tech startup.

Whenever we decided to go down this path, our primary advisor on a Zoom call in the middle of COVID has sold a bunch of companies. He's taken them public. He started them from nothing to go to the highest heights and ring the bell of the New York Stock Exchange. He said, “Are you sure you want to do this? You don't know what you're getting yourself into.”

Mitch and I always laugh about that conversation because we're like, “He told us.” It has been 14 hours a day and with no over exaggeration, 6 or 7 days a week for the last few years not making any money, trying to weed through the waters of this world of startups and find what they call product-market fit. It's been difficult. Raising money is no small feat.

What I've learned from raising money is that you're either in money-raising mode or you're not. You're either balls-to-the-walls running the business as fast and efficiently as you can or you're trying to do that maybe 80% and the other 20% of your time is dedicated with the same level of focus raising money. We've raised a little over $500,000. We're going to go out and raise hopefully a couple of million dollars from the venture capital firms that we have relationships with. It's been a lot of work. Pivots are not very fun. It's starting from scratch but with a lot of pressure.

I love what you said. You're either in that raising money or you're not. It's almost like, “I'm in the same boat.” We raise a lot of money for our real estate. You're either in that mindset or you let that slip. It sounds like you guys are getting ready to transition into that again. You've had a couple of pivots. What are those conversations like?

Even from my experience, you start to do something and get in the groove with that. A lot of people continue doing that even though it might not be working but you're like, “I put so much time and energy into this. We need to keep going and figure it out.” Instead, you said, “That's probably not going to work. Let's take a step back and go a different direction.” What is that conversation? What is that like for you to have that with Mitch, your partner? What did that look like?

I'll never forget this conversation either or at least I hope I don't ever forget it because it was one of the most pivotal conversations of my life. In Halloween 2021, we were running the retail seller business where we were helping retail sellers connect with retail agents. We helped about 77, I think it was the number of retail sellers who connect with retail agents in the Pittsburgh, Pennsylvania market only.

Everybody has a good solid agent in their pocket, especially in Pittsburgh where everybody knows each other. We looked at each other. We looked at our KPIs and said, “It straight up isn't working. We're not going to be able to raise money to sustain this.” Something about Mitch and I and our relationship work out well where we say, “We're going to do this now.” It was when COVID hit and we have that prediction algorithm.

It was a product of having these ideas formulated prior to the pivot but saying, “That would be cool.” Mitch and I always have these long-drawn-out 1.5-hour or 2-hour-long coffee-fueled phone calls or in-person meetings where we brainstorm what we call our pie-in-the-sky ideas. The idea that we pivoted was one of those pie-in-the-sky coffee-fueled ideas. We didn't decide to pull the trigger on it until we looked at the KPIs and said, “This thing isn't growing 20% month over month.”

For us, it needs to raise true venture capital. The customers are happy but it's hard for us to find motivated sellers that don't already have an investor in their ear or an agent in their pocket. We looked at the KPIs and tried to take the most logical and emotionless approach possible. We decided to make the switch because it was either we give up, which neither of us was willing to do or we make this pivot into a world that we knew well, which is the real estate investing world.

How has that been since you've made that pivot? Was that a good move for you? It's hard at the time but looking back, you're like, “That was the right move.”

It was. We had over 800 people sign up for TwnSqr since we launched the new version of the platform in the middle of July 2022. We're making some good revenue. Things are going well. I am thankful to say that I have a lot of venture capital interest from firms that we've already talked to that have expressed interest in the larger goal of the business. Things are going well but it's everyday nose on the grindstone, trying to keep at it. Things are going better than they were whenever we made the pivot.

It's interesting how a little bit of success feels like, “Somebody has signed up. Somebody has paid.” How different that feels than we've given things away for free for a year like we used to do. Having somebody pay for the platform and give us their money and that confidence that we're going to do good for them is a terrifying but good feeling.

It means you're bringing value. I am super excited to see where TwnSqr goes. You're part of a couple of Masterminds with some guys that I know with Collective Genius. You're also in Investor Fuel and meeting some great investors there. I want to ask about your personal life. You met Mitch rock climbing a little bit. You're staying in Airbnb with your wife, Shannon. It sounds like she's pretty busy doing still the photography business. You guys are a young married couple. You talked about working fourteen-hour days for the last few years. What's that been like with your wife and your relationship? You guys are both in entrepreneurship. Can you talk to us about that dynamic?

That whole dynamic is fueled by a lust for freedom. I've always been entrepreneurial and Shannon has always been making her path in her life and trying to go against the grain a little bit. We related in that way whenever we first met. All of that culminates in. We both want to be free and be able to travel around the country and find out what part of the Mountain West we want to live in. All of the hardships that we go through business-wise are fueled by that lust for freedom and being able to say, “No, I'm going to do this. You can't tell me what to do.”

Relationship-wise and family-wise, it was a learning experience and still is a learning experience and a half. I have found the things that make the biggest impact on our relationship in a positive way and I'm sure everybody says this but it's so true. It is being super intentional with my time. I'm in Oregon so between 2:00 and 3:00 PM Pacific, no matter what, I drop everything and we go walk our dogs Monday through Friday. Every single Saturday and Sunday, we have breakfast. We're out of the house usually by 9:30 to 10:30, somewhere in there. We're out walking our dogs or going for a hike. That always involves nature.

Getting to the point where we know this is what makes us feel good, this is what supports our relationship, being super intentional with that time, and then going back to work, it was a hard path to get there but being super intentional with, “I'm done working. I can get a phone call. No problem,” but I'm not at my desk hunched over looking at the computer for at least 45 minutes or so Monday through Friday. That has been the biggest thing that has had an impact on our relationship and becoming closer. One of the biggest things there is being in nature.

I read a book called The Nature Fix. I can't recommend it enough. It's like the science behind what impact nature has on your well-being. It sounds like a whole bunch of woo-woo. They tell you to look at trees, the fractal patterns, and all of that stuff. On a high level, everything that the book talks about is 100% true. My wife and I have a successful relationship because we're intentional with our time but that time that we spend is not spent looking at the TV or our phones. We're out in nature, walking, getting our heart rates up, spending time together, finding conversation, talking about anything that we can, and getting away. That's how we have been able to be successful. It's always a work in progress but that's how we've been able to find success in our relationship.

IDP 100 | Become An Entrepreneur
The Nature Fix: Why Nature Makes us Happier, Healthier, and More Creative

I'll have to check out that book. There is something about nature. You met your partner, Mitch, at a rock climbing. I know the mountains are a part of you. You're traveling around from Airbnb trying to figure out, “Where do we want to be? Where do we want to land?” You're in Oregon and then you're going to Lake Tahoe. What has traveling around different Airbnb been like? Is that exhilarating to you? You're choosing nature places to put yourself in.

It's interesting but the most interesting thing is that every single town in the Mountain West looks the same. At least with the structures, town, and people, Boulder, Colorado looks identical to Durango, Colorado, Salt Lake City, Park City, and Bend, Oregon where I'm at. The homogenization of American cities is interesting. There are some interesting big business moves there that I like to study and understand.

Broadly, traveling around, being out in these beautiful places, getting to stand up from my desk for an hour or so a day, going to the grocery store, walking out of the grocery store, and seeing these 200-foot-tall pine trees in the parking lot of the grocery store is beautiful. We're fortunate to have these experiences. Exhilarating is a great word for it. It's a privilege. I'm super lucky that I've stumbled into something fortunate in my life.

I am super thankful to have you on the show, Paul. It's been awesome with your so much success with TwnSqr.

Thank you.

I want to encourage those that are reading. It sounds like you are still trying to figure out business-wise but also life-wise where are you supposed to be. You're trying different things, taking some risks, and going on a little adventure, which is awesome. I love that. With Iron Deep, we're always interested in getting into these types of places. If you find a place, you're like, “This is amazing.”

We’re trying to immerse ourselves in nature and getting undistracted because as business owners, you're right. We're behind screens all the time, talking on Zoom calls, and always talking on our phones. Needing that undistracted time is so important. I want to give you one last opportunity. Where does someone go if they're interested in TwnSqr? As real estate investors, where do they go?

One quick comment. If you guys are looking for something for Iron Deep, Iron Deep is awesome. I'm so excited for everything that you've built there. You're the perfect person to run it, Brett. You've been such an influence on our business and I can't thank you enough for that, making the introductions that you've made. What you have going with Iron Deep is amazing.

Thank you.

If you're looking for a place that is equally as cool as what you're doing in Iron Deep, you got to check out Bend, Oregon. Bend, Oregon is like adult Disneyland. There's everything from outdoors to good restaurants. It's awesome. As far as TwnSqr, you can check us out at You can contact me directly if you have any questions, want to get onboarded onto the platform, or just connect with me in general. You can send me an email at

I don't use social media too much. I enjoy face-to-face interactions like this and getting on podcasts more than I enjoy Instagram, TikTok, or anything like that. If you want to connect with me somewhere online that isn't through email, you can find me on LinkedIn. You can find TwnSqr on Instagram and those various places. TwnSqr is the name of the company. I'd welcome anybody who's in the real estate investing space to come to check us out. It's $150 a month. It’s super inexpensive compared to other things in the industry. Brett, thank you for everything. Thank you so much for all the support that you've given us.

It's been a blast, Paul. Thank you so much for being on the show. I wish you so much success with your life and TwnSqr.

Same to you. Thank you, Brett. I wish you all the success with Iron Deep and everything that you're doing. I can't thank you enough. Thanks for having me.

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