Tim Milazzo is the co-founder & CEO of StackSource. He identified the market opportunity for a tech-enabled commercial real estate financing platform, recruited Nathan as a co-founder, and built the company. StackSource is now one of the fastest-growing commercial financing companies in the country. Prior to StackSource, Tim worked for tech giants Facebook and Google where he helped expand B2B marketplaces in ad tech. Years ago, he interned at a top NYC real estate company before the current real estate tech wave. He comes from a family with a history in real estate.
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Table of Contents
Let’s learn a little about you and really get to experience what makes us tick – starting at our beginnings. Where did your story begin?
Tim Milazzo: I grew up in NJ in the long shadow of New York City, where my dad commuted to lease-up office buildings as a commercial real estate broker. I studied finance and interned in the real estate industry, but my passion for technology led me to work for big tech companies, including Google and Facebook, in advertising technology.
I reconnected with real estate when I visited a real estate technology meetup with a couple of friends. It was there that my eyes were opened to the intersection of real estate and software, and what it could do for the industry. Ultimately that led me down the path to discovering a huge pain point for real estate investors – there was no easy or transparent way to find the optimal financing for their property investments.
Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up?
Tim Milazzo: Oh man, multiple times. There was a time, early on, when we thought we had a funding round coming together, but then it fell through, right before Christmas. I had to make some hard calls to our team letting them know we were about to run out of money.
But instead of giving up, we all looked at what StackSource could still become if we could persevere and reach the next milestone. For three months, we kept working full time, even though nobody got paid. At that point, not only was our company out of money, but so was I, and I had a wife and kids at home. We were invited to an international startup pitch competition, and had to beg the competition to pay for our hotel. But we prepared like crazy and were able to launch the next version of our platform live on stage. Our problems didn’t instantly go away, and we didn’t even get investment from anyone at the event, but the product launch was a success and we were able to raise more angel capital before revenue started picking up over the coming months.
What are the most common mistakes you see entrepreneurs make and what would you suggest they do?
Tim Milazzo: Well, these are mistakes I made personally, so I know them well:
- Unless you’re a repeat entrepreneur in a hot market segment, don’t build VC-led funding round into your base plan. If you want to pitch VCs and shoot for the moon, go for it. But don’t stake your business on that coming through at a particular moment, or you could be burned. You need a base plan that you can execute, gather data, and other ways to fund and grow.
- Learn as much as you can about someone, and work with them over a period of time, before putting them in a leadership role. You can use your Advisory Board for this, or hire someone as an individual contributor first, and give them really clear goals about what success looks like and how that will translate into leadership. If they don’t hit those goals, fine, you’ve avoided a problem about giving someone too high a title or more responsibility than they can handle.
Resilience is critical in critical times like the ones we are going through now. How would you define resilience?
Tim Milazzo: Of course resilience is a mindset. But it doesn’t happen in a vacuum. It happens in a community with the right support. That’s been really hard over the last year with a pandemic and massive societal changes, but you need to find your tribe and be accountable to people.
What is most important to your organization—mission, vision, or values?
Tim Milazzo: Many entrepreneurs are extremely vision-driven, and I’m one of them. But I think Values are actually more important. I think the most mature leaders are people whose core values are so deeply ingrained that, if you took them and placed them in some alien planet where the culture and opportunities are entirely different, they still have values that define the way they’ll operate, and that will serve them well.
You are a successful business leader. Which three character traits do you think were most instrumental to your success?
Tim Milazzo: I certainly hope I’m on my way there. One character trait that has been necessary for our journey, which I’ve heard from many other entrepreneurs, is perseverance, or grit. Another important one is decisiveness – the ability to bet on the right direction when you have imperfect information and data. Finally, I would not say I’m an expert, but I would say I’m focusing on continuing to develop more empathy in the way I communicate, especially for important but difficult conversations that often define relationships.
What have you learned about personal branding that you wish you had known earlier in your career?
Tim Milazzo: In this day and age, the more transparent you can be, the better. I think younger people that are less advanced in their careers may have a tendency to hold back or even hide what’s really going on, instead of sharing their real thoughts, struggles, and personal development. I have found in recent years that the more “real” you can be in your professional life or online, the more you’ll resonate with people anyway. I regularly share content about a topic I’ve learned, or something I need to learn, and that resonates with people.
How would you define “leadership”?
Tim Milazzo: Leadership is all about creating a path for people to progress toward a common goal. So as a leader, you need to make sure they understand the goal, feel confident in the path, and understand their progress.
Do you think entrepreneurship is something that you’re born with or something that you can learn along the way?
Tim Milazzo: You can absolutely learn entrepreneurship! I would recommend getting closer to it if you don’t have that natural entrepreneurial edge. You can get closer to it by meeting successful (and struggling) entrepreneurs, working closely with them, and reading great books.
What’s your favorite “business” quote and how has it affected your business decisions?
Tim Milazzo: OK, so this applies more broadly than just business, it’s more of a life lesson thing, but especially important in a business setting. So often as people with limited lifespans, we want to skip levels and lessons and get to the end results we desire. But the best indicator of future success is past success. If you don’t have the job you want now, yes, you can say “Screw this” and go and start your own company. But it’s really, really hard, and all but the very few will still have to rely on other people to get anything accomplished in the business world. Instead, take the opportunity in your current context, whatever it is, to do a GREAT job. You’re a janitor? Be a GREAT janitor. You’re an intern? Be the best intern the company has ever seen.
Jed Morley, VIP Contributor to ValiantCEO and the host of this interview would like to thank Tim Milazzo for taking the time to do this interview and share his knowledge and experience with our readers.
If you would like to get in touch with Tim Milazzo or his company, you can do it through his – Linkedin Page
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