Winning Together: Jordan Suber and Chris Ragland of Deep Spring On How Strategic Partnerships Can Unlock New Sales Opportunities
An Interview With Chad Silverstein
A strategic partnership is what happens when trust meets complementary capability. When you have both, you can move faster, go deeper, and deliver outcomes that neither party could have achieved on their own.
Strategic partnerships have the potential to unlock growth and create new opportunities in ways that businesses can’t achieve alone. To explore this important topic, we had the pleasure to interview Jordan Suber and Chris Ragland.
As a part of our series, we had the pleasure to interview Jordan Suber and Chris Ragland.
Jordan Suber is the co-founder of Deep Spring, a commercial real estate advisory firm based in Austin, Texas. A dynamic deal maker and sales leader, Jordan previously built one of the most successful real estate teams in the country, growing it to over 100 agents and closing more than $1.6 billion in transactions, making him one of the top-producing agents in the entire United States. At Deep Spring, Jordan leads business development and client experience, bringing his marketing instincts, people-first approach, and relentless drive to every deal. Chris Ragland is the co-founder of Deep Spring. With over two decades of experience spanning private equity, venture capital, and commercial real estate, Chris has closed billions in transactions and built deep relationships with family offices and large institutional investors across the country. He brings a strategic, trust-driven approach to every partnership and every deal, and co-founded Deep Spring to deliver a truly full-service advisory experience to CRE investors across the Sunbelt and beyond.
Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
Jordan: My path into real estate started with a genuine love for people and a competitive drive to win. I got into residential real estate and quickly realized I had a real talent for building teams, creating systems, and generating volume. Over time I scaled my team to over 100 agents and closed more than $1.6 billion in deals, which put me in a position where I was working with some of the most successful investors in the country. That naturally pulled me toward commercial real estate, where the deals are bigger and the relationships go even deeper. When the opportunity to build Deep Spring with Chris came along, it felt like the next logical evolution of everything I had been working toward.
Chris: For me it was less of a straight line and more of a thread I kept following. I spent the better part of two decades moving across private equity, venture capital, and real estate investment, and what I kept finding is that every sector ultimately comes back to the same thing: the right relationships, combined with the right timing and the right knowledge, create outsized outcomes for everyone involved. Working closely with family offices and institutional investors showed me there was a real gap in the market for someone who could bridge the capital side with the deal side. That insight is what ultimately led to Deep Spring.
Can you share the most interesting story that happened to you since you began working with partnerships or collaborations?
Jordan: The most meaningful partnership story I can share is the one that gave birth to Deep Spring itself, and it started at Barton Springs Pool here in Austin. I had been swimming there with a group of friends, and my now wife, and got to know Chris over time since he was part of that same group. We were the only two guys there, and both was already in real estate, so to keep our minds of the mornings in cold water,we talked about business, real estate, and life. And since then, over six years those conversations got deeper. We started doing deals together informally, referring things to each other, bouncing ideas around. Slowly we both realized our backgrounds were almost perfectly complementary. I had the marketing, sales, and team-building side. Chris had the institutional relationships, the CRE depth, experience and knowledge, and the private equity background. Eventually we asked ourselves why we were doing this informally when we could build something real together. That is when Deep Spring was born. The name is a direct nod to Barton Springs, a reminder that the best things often start in the most unexpected places.
Chris: What I would add is that the partnership with Jordan is the clearest proof I have that the best deals are not found, they are built. We did not sit down one day and decide to start a company. It grew out of years of genuine friendship and mutual respect. And now that foundation is the thing our clients feel when they work with us. It shows up in how we operate, how we communicate, and how hard we fight for their outcomes.
You are a successful leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Jordan: The first is relentlessness. I do not stop until the job is done and done right. When I was growing my real estate team, there were plenty of moments where it would have been easy to plateau. Instead I kept pushing, kept recruiting, kept building systems. That mindset is what got us to $1.6 billion in closed volume. The second is genuine care for people. I have always believed that if you truly care about your client’s outcome more than your commission, everything else takes care of itself. Clients feel that. They refer you. They come back. The third is adaptability. Going from residential to commercial required a real evolution in how I operate, and I leaned into it fully because I knew it was where I needed to go. They are two completely different industries despite both being in the “real estate” sectors.
Chris: For me the first is trust, and I mean that in every direction. I have walked away from financially attractive deals because I did not fully trust the people on the other side of the table, and even killed a $20M deal that Jordan and I were working on a few years ago because of it. It cost us in the short term. But the reputation I built by being selective and honest has returned far more than any single deal ever could. The second is patience. Real estate, private equity, partnership-building, none of it moves quickly if you are doing it right. Patience is not passive. It is disciplined. The third is adaptability. The market I entered twenty years ago looks nothing like the market today, and I have had to reinvent my approach more than once. What has not changed is the commitment to delivering real value. Everything else is adjustable.
What does a “strategic partnership” mean to you, and why do you think it’s such an essential part of sales growth today?
Jordan: To me a strategic partnership is an alignment of strengths toward a shared outcome. It is not transactional. It is not one party extracting value from another. It is two people or two companies, or even a group that are genuinely better together than they are apart. In today’s market, especially in CRE, the deals are too complex and the clients are too sophisticated for anyone to go it alone. The advisors, operators, and capital sources who are figuring out how to collaborate deeply are the ones capturing the best opportunities.
Chris: I would put it this way. A strategic partnership is what happens when trust meets complementary capability. You need both. Trust without capability is just a good friendship. Capability without trust is just a vendor relationship. When you have both, you can move faster, go deeper, and deliver outcomes that neither party could have achieved on their own. That is what drives real sales growth, not just for one deal, but over time.
How do you go about identifying potential partners that align with your business goals? Are there specific qualities or traits you look for in a partnership?
Jordan: I look for people who are serious about their craft and serious about their clients. Do they follow through? Do they communicate proactively? Do they treat every relationship like it matters, not just the ones that are immediately profitable? Those things tell you a lot very quickly. I also look for people whose strengths fill in my gaps. I do not want a partner who does exactly what I do. I want someone who makes the whole stronger.
Chris: I look for three things almost immediately: values alignment, complementary strengths, and transparency. Values alignment sounds soft until you are in the middle of a difficult negotiation or a deal going sideways. That is when you find out whether your partner is playing the long game with you or just protecting their own position. Complementary strengths matter because if we have the same skills and the same perspective, we are not really partners, we are just duplicating effort. And transparency, the willingness to say here is what I am good at, here is where I need help, here is what I want out of this, that is what separates productive partnerships from ones that quietly fall apart.
What steps do you take to build trust and ensure that a partnership will be mutually beneficial for both sides?
Jordan: I lead with value before I ever ask for anything. Early in any partnership I am focused on what I can bring, whether that is an introduction, a resource, or a piece of market knowledge, without expecting anything back right away. That sets a tone. It also reveals a lot about the other person. Do they acknowledge it? Do they reciprocate? Or do they just move on? And I always make sure expectations are spelled out clearly from the start. Ambiguity is one of the fastest ways to damage a good partnership. For example, I never really asked Chris for anything for those 6 years prior other than time to chat and talk about business and life.
Chris: The first thing I do is slow down. There is always pressure to move fast, especially when a deal is on the table. But trust cannot be rushed. I want to understand how someone handles a difficult conversation before I am in one with them. I also make sure we are explicit about roles, decisions, and how we will handle disagreements. Knowing how you will navigate conflict before you are in conflict is the difference between a partnership that survives hard moments and one that does not. Most of the people I’ve worked with at a high level I knew for a very long time first.
Can you share a specific example of a strategic partnership you were involved in? How did it come about, and what impact did it have on your business?
Jordan: One that stands out happened right here in Austin. We were working with a client who is one of the most respected physicians in the state of Texas, a highly accomplished person who had been successful in medicine for decades but was newer to commercial real estate as an investment vehicle. He trusted us to guide him through the entire process, from identifying the right asset to negotiating the deal.
We handled everything: underwriting, property tours, pro-formas, connecting him with the right vendors for due diligence. When it came time to negotiate, we secured the property at 14% below asking price. And when the property appraised, he was sitting on $500,000 in instant equity. That is not luck. That is what happens when you put deep expertise and real relationships behind a client’s goals and treat the deal like it is your own money on the line.
Chris: What that example captures for me is what Deep Spring is really about. We were not just brokers collecting a fee. We were advisors, advocates, and operators all at once. That full-service approach is what sets us apart, and stories like that one are why clients refer us to the people they trust most.
What role does communication play in maintaining a strong, long-lasting partnership? Are there particular practices or tools you use to keep everyone aligned and engaged?
Jordan: Communication is everything. Most partnerships do not fall apart because of a bad strategy. They fall apart because of unspoken expectations and slow-building frustration over things that could have been resolved in a single honest conversation. My rule is simple: say it early. If something is not working, bring it up before it becomes a problem. That applies to client relationships just as much as it does to business partnerships.
Chris: Early on, Jordan and I had to have a direct conversation about who owns what inside Deep Spring. It was not a perfectly comfortable conversation. There was real back and forth. But we worked through it by being honest about our strengths and what would actually serve the business best. Coming out the other side with that clarity made us faster and more decisive as a company. That is the thing about good communication. It is not always easy, but it is always worth it.
Let’s now focus on actionable strategies. Based on your experience, can you share “5 Steps to Create Strategic Partnerships That Drive Sales Growth”?
1. Start with the relationship, not the deal
Before you ever talk numbers or terms, invest time in genuinely getting to know someone. Understand their goals, their pressure points, their standards. The deal will come. The trust has to come first. Jordan and I talked for years before we ever formalized anything, and that foundation is exactly why Deep Spring works.
2. Be crystal clear about what each party brings to the table
A partnership where both people think they are doing most of the work is a partnership on its way to failing. Get specific early about responsibilities, decision rights, and how each side defines success. The more explicit, the better.
3. Give before you ask
Early generosity signals that you are here to build something together, not to extract value. It is also one of the fastest ways to learn whether someone operates the same way you do. People who receive without reciprocating show you who they are very quickly.
4. Treat conflict as a feature, not a bug
Every strong partnership will face a moment of tension. The question is not whether conflict will happen, it is whether you have the communication habits and mutual respect to navigate it. Partners who can disagree openly and still move forward together are the ones who build something lasting.
5. Evaluate the partnership regularly, not just at the beginning
Markets shift, goals evolve, and roles change. Build in honest check-ins on the partnership itself, not just on deal flow. Ask whether it is still working for both of you and whether anything should be adjusted. That kind of ongoing honesty keeps good partnerships from quietly drifting into bad ones.
What advice would you give to smaller companies or startups that may not have the resources or networks of larger businesses but want to start building strategic partnerships?
Jordan: Stop waiting until you feel ready or resourced enough. That day may never come if you are sitting around waiting for it. Figure out what you are genuinely great at and go find people who need exactly that. You do not need a massive network to be useful to someone. You need to understand their problem and have something real to offer. Start there, show up consistently, and treat every small partnership like it is the foundation of something much bigger, because often it is.
Chris: Smaller companies have an advantage that often goes unappreciated: agility. You can move faster, customize more, and give more personal attention than any large firm can. Lead with that. The right partners will see it and value it. Do not try to compete with bigger players on their terms. Compete on yours.
How do you handle challenges or conflicts that may arise in a partnership to ensure that the relationship stays strong and productive?
Jordan: I address things directly and quickly. Conflict that gets avoided tends to grow. Something that could have been resolved in one honest conversation becomes a serious fracture if it sits long enough. My approach is to separate the issue from the relationship. We can disagree on a strategy or a decision without it being a statement about the partnership itself.
Chris: I go into hard conversations curious rather than defensive. What is driving the other person’s perspective? What am I not seeing? When I approach it that way, we usually find a resolution faster than either of us expected. The goal is never to win the argument. The goal is to come out the other side with a stronger working relationship than you had going in. It’s always about us vs the problem, and not you vs me.
Can you share a surprising or unexpected lesson you learned from a past partnership?
Jordan: The biggest one for me is how much role clarity actually matters. I used to think two motivated people would naturally figure out who does what as they go. What actually happens is that both people start operating in the same lanes, stepping on each other’s decisions, and quietly building frustration about work that is not getting done. My wife Melanie and I prior to having our son Alexander ran our real estate business together, and we had the same skills, so we learned early on how to give roles. I took over sales, and she was more marketing and backend. That helped with what we’re building now with at Deep Spring. When Chris and I got explicit about who owns what inside Deep Spring, it changed everything. Now there is no ambiguity, and that makes us faster and more effective every single day.
Chris: Mine is related. The most dangerous thing in any partnership is the assumption that the other person sees things the same way you do. They almost never do, not exactly. And that is actually fine. The problem is when you never surface those differences. The partnerships that have taught me the most are the ones that forced me to get specific about my own expectations and then actually listen to someone else’s. I remember telling Jordan one day about me seeing a board room and thinking, everyone “looked” the same, and I thought to myself, “we’re dead…” You need to have a team full of different kinds of people, backgrounds, skills, and outlooks to have something truly great.
What trends or changes are you seeing in how businesses approach strategic partnerships, and how do you think this will evolve in the coming years?
Jordan: I am seeing a real shift toward intention. Businesses are becoming more selective about who they partner with and why. The days of loose referral arrangements and handshake deals are giving way to more structured, values-aligned collaborations where both parties have skin in the game. I think that trend will continue and accelerate, especially as markets get more competitive and clients get more sophisticated.
Chris: In CRE specifically, I am seeing more collaboration between operators, capital providers, and advisors than I did even five years ago. The complexity of today’s market, the interest rate environment, the geographic shifts, the evolving asset classes, is forcing people to work together rather than compete on every front. The firms that figure out how to build genuine, trust-based ecosystems around their clients will be the ones that win at scale over the next decade.
In your opinion, how do strategic partnerships impact not just sales, but a company’s reputation, relationships, and long-term growth?
Jordan: Your reputation is built on who you associate with and how you treat people through every deal. The best partnerships do not just add revenue. They add credibility, access, and they signal to the market what kind of company you are. At Deep Spring we are very deliberate about who we work with, on both the client side and the partner side. That selectivity is part of our brand, and it compounds over time. It also goes back to being patient. You have to really vet the people you work with and make sure their characters hold up over time. This is a big lesson I learned from Chris, and would see a lot. I feel like a lot of people want to rush things, and then they partner or work with someone who takes advantage of them down the line, so it’s so key to really make sure there is a long term viability there.
Chris: A company’s long-term growth is largely a function of the depth of its relationships. Revenue follows trust. The businesses that prioritize building genuine, durable relationships over short-term transactional wins are the ones that look completely different ten years from now. That is the model we are building at Deep Spring, and it is the bet we are making on ourselves.
You are a person of great influence. If you could start a movement that would inspire more companies to embrace collaboration and partnerships, what would that be? You never know what your idea can trigger. 🙂
Jordan: I would call it Win Together. The idea is simple: what if businesses competed on the quality of their outcomes rather than on how much they could keep for themselves? What if the standard across every industry was honest dealing, radical transparency, and an explicit commitment to making sure everyone at the table leaves better off than they came in? In real estate there is a lot of transactional thinking. People focus on their fee, their margin, their position. I would love to see a shift toward deal-first, people-first thinking, where the measure of success is not just what you closed but the quality of the relationships you built along the way.
Chris: I would build on that by adding the idea of playing a longer game than everyone else in the room. Most people optimize for the next deal. The movement I would want to start is one where businesses optimize for the next decade of deals. That requires trust, patience, and the willingness to put your partner’s outcome ahead of your own short-term interest sometimes. It sounds counterintuitive. It is actually the highest-return strategy I have ever found. A great example of this is a $93.5M deal that we’re working on right now, and most people try to rush deals, but for this size, we are really aiming to make every party work together as a team instead of just us vs them. At this level this behavior sets the pace for the deals to come in the next decade together.
How can our readers further follow you online?
You can find us on Linkedin at Jordan Suber, and/or Chris Ragland, and also on YouTube. We are both very active there.
Jordan’s https://www.linkedin.com/in/jordan-suber-9614a3264/ and YouTube: https://www.youtube.com/@JordanSuber-real-estate
Chris’s https://www.linkedin.com/in/christopherragland/
This was great. Thank you so much for the time you spent sharing with us.
About The Interviewer: Chad Silverstein is a seasoned entrepreneur with 25+ years of experience as a Founder and CEO. While attending Ohio State University, he launched his first company, Choice Recovery, Inc., a nationally recognized healthcare collection agency — twice ranked the #1 workplace in Ohio. In 2013, he founded [re]start, helping thousands of people find meaningful career opportunities. After selling both companies, Chad shifted his focus to his true passion — leadership. Today, he coaches founders and CEOs at Built to Lead, advises Authority Magazine’s Thought Leader Incubator.
Winning Together: Jordan Suber and Chris Ragland of Deep Spring On How Strategic Partnerships Can… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.