Brandon Green

The Hard Way

In 2000, Brandon Green had been working a sales job for a couple years when he saw what would become a life-changing opportunity. He’d never thought about buying property before but saw an infomercial about buying real estate for no money down, and Brandon was intrigued. “I thought, maybe I could do that,” remembers Brandon. “I bought the course and studied it. My roommate at the time thought I was crazy, sitting at the dining room table going through all these cassettes and manuals.”

Brandon ended up buying a property on Capitol Hill for $100,000 with only $1,000 down and a good credit score. Even the $1,000 was borrowed from a friend. “It was a bank owned property, and I bought it using a 203(k) government renovation loan. I renovated it and ended up selling for a profit of $40,000, and I thought I was the bomb,” laughs Brandon. “Of course, what I know now is, I was lucky. I had no idea what I was doing!”

Risky though the venture was, it had paid off in spades, and Brandon’s interest in real estate was piqued. As he worked at flipping his first property, he began looking into working as a real estate agent, and right away found he had a knack for the work. Within a couple of years, Brandon was clearing $200,000 a year and posting a remarkable number of sales. A few years after that, in 2006, he and four partners launched a brokerage, Keller Williams Capital Properties (KWCP), which took off and expanded to several locations across the DC area.

“Launching KWCP made me change my thinking, from individual sales producer to a business owner. I started to map out the things I needed to change and the skills I needed to learn to grow the company,” explains Brandon. “I did not go to business school, I had a year or so of community college, and I was just operating on pure work ethic and personality. I realized pretty quickly that there’s only so far you can get with work ethic and personality, something new has to emerge eventually.”

He attributes his compassion for others to his father noting that, “As early as possible, he had us visiting nursing homes and care facilities, spending time with people who really enjoyed and needed the company.”

Brandon is self-made in every sense of the word, and what he’s learned, he notes he learned “the hard way.” But Brandon has managed to meet every setback and challenge with his trademark grit, determination, and willingness to learn; and KWCP not only survived, it continued to thrive and expand. At the age of 41, he was able to bring on new hires to manage day-to-day operations of the brokerage and stepped away to begin working on new projects, including Chapter 2 Ventures.

Chapter 2 Ventures combines Brandon’s hard-won expertise with his passion for growing businesses and his large professional network. Chapter 2 is a network of real estate professionals who invest in impact-oriented small businesses with a focus on diverse and underrepresented founders. “A demographic of entrepreneurs I connect with because of my personal journey are people who are not equipped with traditional resources that come from networks developed by people who take more traditionally successful professional paths. Let’s face it, men, particularly white men who graduate from Ivy League institutions bring with them a network that includes contacts and capital that people without those credentials do not have,” notes Brandon.

“There is a compelling argument to invest in these businesses. Not only does increasing diversity in successful founders help our society, research is showing these companies typically outperform other companies by a variety of financial metrics – which translates into less capital and higher returns.”

“The challenge is finding scalable businesses, but when we do, we make the investment, and provide a menu of services to help the business grow to the next level.” Brandon goes on, “We are not projecting a capital event at the end of five years for these businesses; rather, we like community-based businesses, with owners who plan to keep and grow the enterprise.”

The investors in Chapter 2 come from Brandon’s many years in real estate; in his field, he’s made hundreds of connections with other agents and brokers, all of whom encounter small business owners frequently in their work. “Someone will approach me and say, I just sold a house to so-and-so, they own a business and they’re looking to scale, they could be a candidate for Chapter 2,” explains Brandon. “Chapter 2 brings together the capital from my network, and that network helps find the business opportunities for vetting.”

Chapter 2 is still new, and therefore, its operations are still being refined. Vetting, for example, is an area that as of now is done carefully on a case-by-case basis. Brandon knows, however, that to grow, certain hard-and-fast criteria will need to be agreed upon. Similarly, Chapter 2’s service offerings are open-ended at the moment, but generally comprise three major areas of concern—back-end financial and operational management, sales and marketing, and risk management. “One of our challenges at the moment is, if we’re going to be providing, for example, the accounting and bookkeeping services, and the sales and marketing services, how do we do that at scale with this type of business investment? We’ve identified buckets where small business owners need expertise. Our next step is figuring out how we advance those buckets efficiently.”

Like the entrepreneurs he aims to help, Brandon did not attend business school nor follow a traditional path, and, as a gay man, he faced his own challenges growing up Mormon in Rock Springs, Wyoming. As a kid, he knew he was “different”, noting that he preferred to befriend girls over boys, disliked organized sports, and began to develop a passion for music. Still, in many ways, Rock Springs was an ideal setting for a childhood filled with exploration and wonder. “We grew up in a wonderful neighborhood,” recalls Brandon. “I would spend all my time in the desert riding my bike. I remember leaving the house on my bike at 9:00 AM, and my mom would say, ‘Just be home by dinner.’ I’d go out, who knows where, and absolutely loved it.”

Brandon spent most of his time with his favorite cousin, Kristen, and his younger sister Amber, and often saw the rest of his extended family, all of whom lived nearby. His father was the Principal of an elementary school just down the road, and his mother alternated between staying at home and working as the school’s secretary. As a kid, Brandon enjoyed going to the Mormon church, where his father was the bishop, and the family would spend 3 or 4 hours there every Sunday. Rock Springs was a mining town, with a population of 19,000—a small town that to a small boy seemed huge.

During those first 12 years of his life in Wyoming, the only major shadow on the family’s life was the death of Brandon’s uncle Jeff at the hands of a high-profile criminal, Mark Hopkinson. After taking a job with the man’s family, Jeff slowly became involved in organized crime as Mark asked him to take on more and more work. Ultimately, Jeff tried to break free of Mark’s grasp, testifying against him in court, but Mark’s criminal network found and killed him in retaliation. For years, the entire Green family received threats from Mark even though he was in prison awaiting execution. It kept the whole family on edge. “I think my childhood was very peaceful and traditional in many senses of the word,” acknowledges Brandon. “But from time to time, this tension would appear. We even had police protection a couple of times, as Mark came up for execution by the state of Wyoming.”

Brandon’s father, Jeff’s brother, had found refuge from his rough upbringing through education, and although he had a good job as Principal, was set on becoming a Superintendent of schools. To do so, he’d need a PhD, and the Green family relocated to Ames, Iowa for this purpose. His father made the decision not to work while he was pursuing the degree, so the Greens had to survive on savings. Brandon was 12, just entering adolescence, and the move was a hard one. “We went from a 3,000 square foot house, to a 14 x 17 trailer,” he remembers. “It was a shocking experience for me. All of a sudden, nobody knew me, and my family didn’t seem to have the resources it used to have.”

Brandon made few friends other than the son of his piano teacher. He’d begun taking piano lessons before leaving Wyoming, and he threw himself into singing and piano wholeheartedly. Music became a refuge as he endured his confusing middle school years, more aware than ever that something set him apart, but still unsure what that was. And when his father finished his PhD program, things hardly calmed down; in fact, that was when, in Brandon’s words, “All hell broke loose.”

“It was the beginning of me seeing my real self.” Brandon won the election and became Senior Class President. Finally, he felt he belonged.

The Green family decided to move to Eagle Point, Oregon, where Brandon’s father had been offered an Assistant Superintendent position. Along with being the new kid all over again, Brandon had another big change to deal with—his parents’ adoption of his two younger sisters, Tina and Mandi. Brandon, by this time, was about 14. Tina and Mandi were 2- and 3-year-old half-sisters who had been fostered by family friends at church. Brandon’s mother heard that the state wanted to keep the sisters together but could not find a home for them and would likely have to separate them. “That really bothered my mom,” recalls Brandon. “She said, well, I think we can take them on.”

The two young girls were suffering from physical and psychological problems, and it didn’t help that the whole family relocated to Oregon immediately after adopting them. It was an adjustment period for everyone, and Brandon began acting out as well. No one was enjoying the time in Eagle Point; even his father’s job turned out to be a bad fit. “I only had one friend in Oregon,” recalls Brandon. “This girl Bonnie, who wanted to be my girlfriend, and I had no interest in being her boyfriend- so that was confusing to me.” Academically, things weren’t all bad—along with his focus on music, Brandon remembers two great middle school teachers who encouraged his passion for speech and debate.

After only one year in Oregon, the family returned to Iowa, this time to a suburb of Des Moines called Urbandale, where Brandon’s father accepted an elementary school Principal position. Despite all the investment in his PhD and the upheaval it had caused the family, he was back at square one, which was tough on him.

Brandon looks back on those times now and admires all his parents were able to do for the family. He attributes his compassion for others to his father noting that, “As early as possible, he had us visiting nursing homes and care facilities, spending time with people who really enjoyed and needed the company.” And from his mother, Brandon feels he inherited “stick-to-it-iveness.” “Sometimes it’s stubbornness,” admits Brandon, “but for the most part it’s focus around the objective, getting things done no matter the obstacles that might come into the path. My mom has an amazing ability to set a vision and achieve it, no matter what.”

Back in Iowa, things began to turn around for Brandon. Academically, he had always done well, and musically, he was more committed than ever. Junior year arrived and he decided to run for Class President even though he knew winning was a long shot. “It was a crazy idea; I was not a popular kid. My campaign slogan was, ‘The Grass is Greener’, and my friends hung posters all over the school,” laughs Brandon. “I knew the one shot I had was when all of the candidates had an opportunity to give a speech. I practiced that speech so much that when I gave it, it was an out of body experience. In that moment I could see, not only did I transform in front of all my peers, I also saw myself as someone different. It was the beginning of me seeing my real self.” Brandon won the election and became Senior Class President. Finally, he felt he belonged.

That same year, Brandon had the transformative experience of going to see a show called “Up With People”, a musical performance put on by kids ages 18-23, who travelled the country and the world together. Immediately, Brandon knew what he wanted to do: bypass his parents plans for him of going on a mission trip and then onto college. Instead, he wanted to join the travelling performers. The only hiccup was the $15,000 tuition he’d have to come up with. Fortunately, Brandon was scrappy; from selling chocolate Santa Clauses, to pitching sponsors on donations, Brandon single-handedly raised the money.

For six months, Brandon travelled with Up With People across the U.S., visiting Colorado, Utah, Oregon, Washington, Idaho, Wyoming, Nebraska, the Dakotas, Minnesota, Iowa, Illinois, and Ohio. Students with the group did everything from scenery design to costumes, lighting, and sound; but Brandon was one of the performers, singing and dancing every night for new crowds. Then, after a holiday break, the troupe went overseas for another six months, flying to Finland, then travelling to Sweden, Norway, the Netherlands and Russia. Everywhere the group went, they performed at local community centers and schools, and stayed with host families. The experience was absolutely transformational, and Brandon made lifelong friends.

But a year later, his high high was followed by a low low when he returned home and lived in his parents’ basement as he tried community college. It was depressing, and it was also right around this time that Brandon realized he was gay. Quite suddenly, driving home from the gym one night, he had an epiphany. Not long after that, his father confronted him about his sexuality. “He just came downstairs and said, ‘Son, are you a homosexual?’ I was shocked. I’d never even heard that word,” remembers Brandon. “I knew by then that I was gay, but I wasn’t planning on telling my parents anytime soon.” Coming out wasn’t all smooth sailing; his father cried, his mother screamed, and his parents had to do a lot of work to reconcile this new reality with their long-held religious convictions. However, his parents never disowned him, and they quickly reassured him that they’d love him no matter what. “For a long time, we didn’t talk about it. They had their own journey they needed to go on,” explains Brandon. “I was not as patient as I could’ve been with them. Now, our relationship is great.”

Fortunately, he soon got a call from Up With People asking him to return, this time as an advance staffer, visiting locations to secure venues for the troupe. Brandon happily accepted and spent another year travelling, before returning to the U.S. and moving to Baltimore, Maryland.

“I found that the ratio was about 100:1. For every 100 doors I knocked, 1 person invited me in for a conversation. For every 2 conversations, I got one client who would actually hire me to sell their property.”

In Baltimore, Brandon knew nobody and had no job. But he was quickly hired at an IT Staffing sales company, and before long his appetite for the sales business was impressing his bosses. He learned that a huge part of sales is work ethic. If you make 100 calls, you’ll get 5 meetings, and you’ll close 2 deals. He kept those ratios at the forefront of his mind and was always hustling. The first year, he made about $70,000. By his second, he hit almost $100,000. Leaving the work to go back to school made no sense to him; instead, he buckled down and honed his craft.

This self-education would prove invaluable as, after his first property purchase, he moved on to real estate sales. “I started knocking on doors,” Brandon says. “I gridded out the neighborhood, and I went door-to-door, and I found that the ratio was about 100:1. For every 100 doors I knocked, 1 person invited me in for a conversation. For every 2 conversations, I got one client who would actually hire me to sell their property. And I quickly realized my colleagues were not doing this. That’s how my real estate career started out so quickly.”

By 2004, a mere four years after his first real estate purchase, he was making $200,000 annually. But Brandon had his sights set higher. He realized that a brokerage firm was more leverageable, and thus, a path to greater success. KWCP was, therefore, born in 2006 while Brandon still maintained his sales team.

Unfortunately, there were some setbacks. The first major one was when Brandon’s CPA informed him that he hadn’t been keeping up with his tax payments, and Brandon realized he was in tax debt. Although he had been making great money for years, he’d never learned much about money management, and the experience was the start of a new relationship with money. The friend who had loaned him a thousand dollars to buy his first property gave Brandon some unforgettable advice. “He told me, ‘I don’t know any billionaires who talk about money the way you do,’” remembers Brandon. He advised, ‘You can’t say you’re good with people but not with numbers and expect to make the money you want to make.’ “It was one of those nuggets of advice that happens at just the right moment, when you’re open enough to hear it. It completely changed how I took responsibility for money. To me, that’s one of the guiding principles to how I do business—if I don’t understand it, I won’t get involved.”

By 2011, KWCP had opened four offices across the city, and on top of that, Brandon was flipping homes, working with his sales team, buying property to keep longer term, and starting to explore other companies such as title, mortgage and insurance. “By then I’d been in sales ten years, and I was a bit burned out,” admits Brandon. “So, I hired someone to run the sales team and began to turn more of my focus to the brokerage side and apply my skills to launch more offices.”

While Brandon took over day-to-day operations of KWCP, one of his other partners handled a new real estate development project, which Brandon invested in. Over the next several years, KWCP was firing on all cylinders. And from 2016 through 2018, the business opened four additional branches. After the branches launched successfully, Brandon made the decision to hand over the reins to a COO he hired and step back from day-to-day operations.

In 2013, Brandon married his long-time partner Christian. The two met working together back in 2004, when Brandon hired Christian as his first assistant, and quickly began dating shortly thereafter. “He’s entirely different from me,” Brandon reflects, affectionately. “He’s very creative, he owns an interior design and home staging business. What I get from him is the reminder to slow down, to appreciate the little things, the simpler moments, to relax and enjoy, and rest. He’s quick to remind me to calm down; it’s a great counterbalance.”

Still, Brandon can’t relax for long. Along with his work on Chapter 2 Ventures, Brandon has been writing a memoir, and he’s fortunate to have decades worth of journals to reference as he reflects on his journey. In fact, Brandon considers the journals to be his prize possession, an invaluable record of all he’s gone through. Along with the memoir, he’s taken up speaking engagements, aiming to give 1-2 keynotes each month, with themes around leadership and entrepreneurism.

“A couple things I’ve learned about leadership are underappreciated,” Brandon asserts. “One is the power of vision. The degree to which the vision is clear is crucial. The second thing that I really believe in is listening to and paying very close attention to our people. To me leadership from behind is the way to lead, empower and elevate others.”

To young people looking to launch their career, he advises patience. “For ambitious, motivated kids, there’s this, you think you’ve got to have it all figured out at 22, 23. You don’t, and you’re not going to! So, you may as well just stop it. Don’t be in a rush, you have time.”

Brandon’s career is a living example of this reality. “I learned the lessons, and I learned them the hard way,” reflects Brandon. “That’s part of why I identify so much with these hustle entrepreneurs. I didn’t learn any of these lessons in business school, I learned them losing money, losing relationships, by messing up, by going back to zero and being frustrated by that, by acknowledging when I didn’t have the skill set and figuring out how to improve that. These lessons are part of my lifelong journey, not a destination point, but a road I’ve chosen to go down.”

Brandon Green

Gordon J Bernhardt


President and founder of Bernhardt Wealth Management and author of Profiles in Success: Inspiration from Executive Leaders in the Washington D.C. Area. Gordon provides financial planning and wealth management services to affluent individuals, families and business owners throughout the Washington, DC area. Since establishing his firm in 1994, he and his team have been focused on providing high quality service and independent financial advice to help clients make informed decisions about their money.

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