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Tim Milazzo Tells Us How StackSource is Navigating Challenges in Commercial Real Estate Fintech

kokou adzo



Tim Milazzo StackSource

First of all, how are you and your family doing in these COVID-19 times? 

Tim Milazzo: My wife was pregnant when the pandemic grew, and the lockdown started, which was cause for concern. We didn’t know if our local hospital would be overrun with COVID patients or whether I would be allowed in to accompany her through labor. Thankfully, by the time she gave birth in July, there were no more COVID cases at the hospital, and we stayed together through the birth of two healthy twins! ( me holding them in the hospital).

Tim Milazzo StackSource1

Tell us about you, your career, how you founded StackSource.

Tim Milazzo: I grew up in a “real estate family,” studied finance, and interned for big real estate and finance companies. But I was in love with the idea of tech companies and innovation. So when I received a job offer from Google coming out of college, I jumped at it. For a few years, I worked my way around and up through the advertising technology departments at Google and later at Facebook, which was an invaluable experience surrounded by awesome people.

Somewhere down the line, though, I realized two things:

1. I wanted to build something and learn from the attempt to build something innovative.

2. Real estate tech (now typically referred to as “proptech) was a huge opportunity. 

How does StackSource innovate? 

Tim Milazzo: I talked with 100 people in the commercial real estate industry before we really shaped our project and called it StackSource. We found that of the 50,000+ commercial real estate owners across the country, the big real estate finance firms really only focused on the top sliver of the market, and there was a wide cut of the market that needed transparency into commercial financing options. So we have built and continue to build tech that simplifies the process of shopping for commercial property loans and makes it much more transparent.

How the coronavirus pandemic affects your business, and how are you coping?

Tim Milazzo: At the beginning of the lockdowns, it was painful. Real estate lending nearly shut down across the board for a while in Q2, and we lost hundreds of thousands in revenue. 

But as the lockdowns dragged on and the capital markets remain choppy, it’s now turning into a tailwind because these real estate investor clients are having even more trouble finding financing through traditional channels, and no one is meeting their next lender at a big conference.

Did you have to make difficult choices, and what are the lessons learned?

Tim Milazzo: Absolutely. Leaving a stable job and a nice salary to put your own money and savings on the line with a startup is a huge leap. I would caution other entrepreneurs that they better be sure about diving into the deep end with a startup because there might not be a financial lifeline. There were times when I had credit card debt and wasn’t sure how to make payroll. 

How do you deal with stress and anxiety? How do you project yourself and StackSource in the future?

Tim Milazzo: If you find your entire identity and self-worth is tied up in how your company is doing or in your finances, then speculating with a startup can definitely mess with your head. There’s a reason that depression and mental illness trend higher with entrepreneurs. 

I find that self-care is essential. For me, that means I need to seek spiritual, physical, and emotional balance. On the spiritual side, for me, it’s prioritizing time for prayer, reading Scripture, and spiritual reflection. On the physical side, it’s exercise and diet. On the emotional side, it’s investing in the most important relationships. Doing all these things well necessarily takes time away from the business, make no mistake. There may be times when the scales tip. If you want to go fast, you can cut all of these out for a time. But if you want to go far, you won’t make it without striking a healthy balance, and you’ll be miserable trying.

Who are your competitors? And how do you plan to stay in the game?

Tim Milazzo: Most of our competitors are old-school brokers. They have relationships and knowledge, but there’s very little transparency to their process for the client, and they are quite inefficient. Our strategy is to give our own Capital Advisors an advantage through our tech platform and give our clients the ease and transparency they want out of the financing process.

Your final thoughts?

Tim Milazzo: So we’re working on something brand new as well. It’s a browser extension that allows real estate investors to overlay investment and financial analysis on property listings on the fly. An investor would be on a commercial property listing site, browsing through different properties they may want to buy. Instead of opening up a separate window to do the math about whether it’s a decent investment given certain assumptions, they can overlay that right on the property listing, pull in live financing rates, and share the results without ever leaving the browser tab.

Your website? for our tech-enabled financing service for the recent announcement about the browser extension.

Kokou Adzo is the editor and author of He is passionate about business and tech, and brings you the latest Startup news and information. He graduated from university of Siena (Italy) and Rennes (France) in Communications and Political Science with a Master's Degree. He manages the editorial operations at

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