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How Pierre Calzadilla Is Redefining Real Estate Finance with Upfront
In an industry known for its steep barriers and outdated systems, Upfront is flipping the script—and COO and Co-Founder Pierre Calzadilla is at the center of it. A startup veteran and real estate insider, Pierre has spent nearly two decades building growth teams at companies like Trulia, RealScout, and Local Logic. Now, with Upfront, he’s leading a new wave of innovation aimed at empowering real estate agents with the tools they need to thrive.
Upfront’s core mission is clear: deliver seamless, equitable financial solutions for real estate professionals. For independent agents and brokerages alike, cash flow has long been one of the biggest hurdles—delayed commissions, inconsistent income, and limited access to benefits have historically made it difficult for agents to build sustainable careers. Upfront changes that.
With programs like Pipeline Protection—which allows agents to access up to 90% of their commission before a deal closes—Upfront helps agents gain control over their finances. For brokers, Upfront provides white-label services that integrate financial disbursement and healthcare benefits directly into their operations, creating a win-win across the board. Their flat-fee structure, quick access to capital, and tax-deductible services are attracting attention for all the right reasons.
Pierre’s leadership has been instrumental in this shift. Drawing on his experience scaling teams from 0 to $10M in revenue, he’s helped shape a culture at Upfront that values clarity, accessibility, and agent-first thinking. It’s not just about providing services—it’s about rebuilding trust in the financial systems that support the real estate workforce.
Upfront’s work recently gained even more visibility through its inclusion in the NAHREP REACH Labs Innovation Showcase hosted by the Hispanic Wealth Project (HWP).
Upfront’s core mission is clear: deliver seamless, equitable financial solutions for real estate professionals. For independent agents and brokerages alike, cash flow has long been one of the biggest hurdles—delayed commissions, inconsistent income, and limited access to benefits have historically made it difficult for agents to build sustainable careers. Upfront changes that.
With programs like Pipeline Protection—which allows agents to access up to 90% of their commission before a deal closes—Upfront helps agents gain control over their finances. For brokers, Upfront provides white-label services that integrate financial disbursement and healthcare benefits directly into their operations, creating a win-win across the board. Their flat-fee structure, quick access to capital, and tax-deductible services are attracting attention for all the right reasons.
Pierre’s leadership has been instrumental in this shift. Drawing on his experience scaling teams from 0 to $10M in revenue, he’s helped shape a culture at Upfront that values clarity, accessibility, and agent-first thinking. It’s not just about providing services—it’s about rebuilding trust in the financial systems that support the real estate workforce.
Upfront’s work recently gained even more visibility through its inclusion in the NAHREP REACH Labs Innovation Showcase hosted by the Hispanic Wealth Project (HWP).
Q&A with Pierre Calzadilla
What motivated you to launch Upfront, and how does your experience in prop-tech influence its mission?
Pierre: Relationships. My co-founder Muk and I met when I was introduced to him as an advisor for a previous brokerage he started in Boston while at Harvard. Over the years, we became friends and would share ideas for companies we wanted to start. In 2023, he called me with the original idea for Upfront. It made perfect sense—was a real problem with the disconnect between work, and when you get paid in real estate. I saw a few ways we could really make something special based on my experience in prop-tech and the real estate industry in general. I was exposed to these financial issues from both the brokerage and agent side over the years, as was Muk when he was a broker in Boston. He believed in me, and I believe in him, so we set out together, and so far, we've been proven right.
How is Upfront helping to close financial gaps for real estate agents, especially within underrepresented communities?
Pierre: For one, we are not predatory. Most companies in the space are "commission advance" companies. A term which may as well be known as a "pay-day lender." They are terribly costly and prey on people in need. They charge exorbitant fees, not because of risk, but because they can get away with it. To put it simply, we operate very differently. First, we partner within the brokerage—it's an actual in-house benefit and agents can't use our service outside of our brokerage partners. Second, our fees are the lowest in the industry, with among the friendliest terms. We have no hidden fees, we transfer deals at no cost, and more. We built this from the ground up for the real estate industry and the unique challenges they face.
What lessons from your time scaling startups like Trulia and RealScout are helping you build Upfront differently?
Pierre: It’s two sets of lessons really. What to do, and what mistakes to avoid, I wrote this post - maybe best to just repost it:
What motivated you to launch Upfront, and how does your experience in prop-tech influence its mission?
Pierre: Relationships. My co-founder Muk and I met when I was introduced to him as an advisor for a previous brokerage he started in Boston while at Harvard. Over the years, we became friends and would share ideas for companies we wanted to start. In 2023, he called me with the original idea for Upfront. It made perfect sense—was a real problem with the disconnect between work, and when you get paid in real estate. I saw a few ways we could really make something special based on my experience in prop-tech and the real estate industry in general. I was exposed to these financial issues from both the brokerage and agent side over the years, as was Muk when he was a broker in Boston. He believed in me, and I believe in him, so we set out together, and so far, we've been proven right.
How is Upfront helping to close financial gaps for real estate agents, especially within underrepresented communities?
Pierre: For one, we are not predatory. Most companies in the space are "commission advance" companies. A term which may as well be known as a "pay-day lender." They are terribly costly and prey on people in need. They charge exorbitant fees, not because of risk, but because they can get away with it. To put it simply, we operate very differently. First, we partner within the brokerage—it's an actual in-house benefit and agents can't use our service outside of our brokerage partners. Second, our fees are the lowest in the industry, with among the friendliest terms. We have no hidden fees, we transfer deals at no cost, and more. We built this from the ground up for the real estate industry and the unique challenges they face.
What lessons from your time scaling startups like Trulia and RealScout are helping you build Upfront differently?
Pierre: It’s two sets of lessons really. What to do, and what mistakes to avoid, I wrote this post - maybe best to just repost it:
Laser focus. This phrase was stated by Pete Flint, and all the leaders at Trulia for many years. There is always so much opportunity, and you have to keep your eyes fixed on where you are going, and the key outcomes you are pursuing. This requires clear communication, vision, and alignment—paired with transparency and shoulder to shoulder leadership. Sami, Heather, Sean, and Kelly, are the core team that hired me at Trulia.
Create the problem. Too often ideas can die before they are born. How? Well people bring up all the problems, and “ifs” that could happen. It’s such a nuanced thing, because some of those problems only come from mass adoption, or success metrics—like actual usage and paying customers. Don’t kill ideas that have potential, based on fear. Fear is never a good decision factor, ask yourself instead, “what’s the worst that can happen?” And work from that vantage point. Often, only by driving the idea forward, to its worst outcome, can you see around corners that you were blind to. Arthur, Andrew, Russel, and Michael.
Do what you said you would do. Never fall short of promises. Over communicate. How do you avoid this trap? Under promise and over deliver. Clients will remember, and I’m grateful that many of my partners have been with me—for every company I’ve brought to market. That’s not by accident. It’s a result of integrity. Vincent-Charles Hodder, Gabriel Damant-Sirois, my friend Audrey Whittington, and truly something all of my leaders have displayed.
Clear vision, culture, mission. Every company I’ve tenured at has had an early culture, vision, and mission. From BOFFI, and IMPACT, to Eat, Hustle, Play or Love as a culture foundation—and my favorite now, Joy. Choose the culture you want to build. It’s a fragile thing that evolves, but if you don’t nurture it, it can go badly. Tracy Lawrence and Sami stand out to me, Tracy now coaches leaders and Sami built another Unicorn with strong culture—no surprise!
Find your people—you’re not alone. Each company had core people that didn’t complain, moan, or talk negatively about what we were building. They were all in, and could see past the startup challenges, they had grit, hustle and stuck in when it got hard. These are the ones that will be there, through the churn, and into the future. You know who you are! Today, my cofounders Ishtyaq and Mukund are my rocks.
Create the problem. Too often ideas can die before they are born. How? Well people bring up all the problems, and “ifs” that could happen. It’s such a nuanced thing, because some of those problems only come from mass adoption, or success metrics—like actual usage and paying customers. Don’t kill ideas that have potential, based on fear. Fear is never a good decision factor, ask yourself instead, “what’s the worst that can happen?” And work from that vantage point. Often, only by driving the idea forward, to its worst outcome, can you see around corners that you were blind to. Arthur, Andrew, Russel, and Michael.
Do what you said you would do. Never fall short of promises. Over communicate. How do you avoid this trap? Under promise and over deliver. Clients will remember, and I’m grateful that many of my partners have been with me—for every company I’ve brought to market. That’s not by accident. It’s a result of integrity. Vincent-Charles Hodder, Gabriel Damant-Sirois, my friend Audrey Whittington, and truly something all of my leaders have displayed.
Clear vision, culture, mission. Every company I’ve tenured at has had an early culture, vision, and mission. From BOFFI, and IMPACT, to Eat, Hustle, Play or Love as a culture foundation—and my favorite now, Joy. Choose the culture you want to build. It’s a fragile thing that evolves, but if you don’t nurture it, it can go badly. Tracy Lawrence and Sami stand out to me, Tracy now coaches leaders and Sami built another Unicorn with strong culture—no surprise!
Find your people—you’re not alone. Each company had core people that didn’t complain, moan, or talk negatively about what we were building. They were all in, and could see past the startup challenges, they had grit, hustle and stuck in when it got hard. These are the ones that will be there, through the churn, and into the future. You know who you are! Today, my cofounders Ishtyaq and Mukund are my rocks.
These are some highlights, there are many layers to them. It’s also about how you measure and create the guardrails for your team to flourish. Feel free to ask me any questions via DM or right here. Would love to hear your thoughts on this or your own reflections.
What’s one key challenge you’ve faced while launching Upfront, and how did you overcome it?
Pierre: We are still in it. Upfront is on the right trajectory, we are still scaling, still learning. We still have to overcome the stigma that typical commission advance companies have brought to the space (which makes sense since they have pretty horrible terms). We chose to really focus on the "why" these services are needed, and "how" we are a completely different product. We further try to separate ourselves by focusing on what we do, "early commission access" vs. the loaded "commission advance." In our opinion, the commissions we pay are earned. The default rate is 0%, because we have strict underwriting rules—but also because of how we work when a deal does fall through. That has happened, but we transfer the deal with our Pipeline Protection product and save the agent any negative fees.
What advice would you give to other Latino entrepreneurs building in fintech or prop-tech today?
Pierre: Relationships. Don't gate-keep, open your calendar to meet with others, and share your network. Connect with people that are in your sphere and learn together. It's tough being a solo founder, I could not imagine it. So, if you are, create a group of fellow founders - even in different verticals—to share the joys and burdens. You can't do it alone.
Upfront’s presence at the NAHREP Innovation Showcase was a natural fit, underscoring the company’s commitment to elevating industry standards through inclusion and scalable solutions.
Founders looking to follow in Pierre’s footsteps can apply to the HWP Accelerator Program, which supports early-stage entrepreneurs with virtual workshops, investor showcases, and a focus on business growth and personal wellbeing.
What’s one key challenge you’ve faced while launching Upfront, and how did you overcome it?
Pierre: We are still in it. Upfront is on the right trajectory, we are still scaling, still learning. We still have to overcome the stigma that typical commission advance companies have brought to the space (which makes sense since they have pretty horrible terms). We chose to really focus on the "why" these services are needed, and "how" we are a completely different product. We further try to separate ourselves by focusing on what we do, "early commission access" vs. the loaded "commission advance." In our opinion, the commissions we pay are earned. The default rate is 0%, because we have strict underwriting rules—but also because of how we work when a deal does fall through. That has happened, but we transfer the deal with our Pipeline Protection product and save the agent any negative fees.
What advice would you give to other Latino entrepreneurs building in fintech or prop-tech today?
Pierre: Relationships. Don't gate-keep, open your calendar to meet with others, and share your network. Connect with people that are in your sphere and learn together. It's tough being a solo founder, I could not imagine it. So, if you are, create a group of fellow founders - even in different verticals—to share the joys and burdens. You can't do it alone.
Upfront’s presence at the NAHREP Innovation Showcase was a natural fit, underscoring the company’s commitment to elevating industry standards through inclusion and scalable solutions.
Founders looking to follow in Pierre’s footsteps can apply to the HWP Accelerator Program, which supports early-stage entrepreneurs with virtual workshops, investor showcases, and a focus on business growth and personal wellbeing.
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