On the occasion of our nation’s 250th birthday, I am sharing the first two chapters of my personal stories from my upcoming book: “Owning, Leasing, Selling, and Buying Commercial Properties – Advice from a Time-Tested Investor, Strategist, and Broker”. Here is Chapter 2, following Chapter 1 that I shared previously.
– To Watch the 18-min video
– To Listen to the podcast
The high salary during those years working for defense contractors had allowed me to begin investing early. When I left the corporate world, I converted my company 401(k) into a self-directed Roth IRA and invested the proceeds in stocks and real estate. After losing all my 401(k) in the stock market during the 2000 to 2002 dot-com bust, I started dipping my toes into residential and eventually commercial real estate.
I bought and flipped properties while still working in technology, which later gave me enough knowledge and financial stability to take time off and eventually transition into a commercial real estate career full time.
For the first time in my adult life, I took an entire year off to reflect on what I truly wanted.
As time went by, I came to realize that even though I am analytical and great with numbers, something was missing deep inside when I was working solely as a software engineer. I started missing the part of my life that constitutes who and what I am: I am a people person, naturally talented at and drawn to people-oriented work. Persuasion and relationship-building had always come to me naturally.
I consider my people skills to be the core strengths behind my success in commercial real estate. People often tell me they feel comfortable around me the first time we meet, or almost immediately after.
Growing up, family members often asked me to speak with younger relatives because of my influence and persuasion skills. I once talked my niece, who refused to eat vegetables, into trying broccoli. My sister was amazed at how easily I influenced my niece. Family members often relied on me to communicate with their children or to help navigate difficult conversations because I could make people feel comfortable and understood.
Real estate is fundamentally a people business, and authentic connection matters. Above all, I care deeply about outcomes and helping clients succeed financially.
In contrast to the highly structured, corporate, and secretive nature of defense work, the human-centered world of commercial real estate advisory and brokerage combines people skills, financial knowledge, and personal connection in ways engineering never could. It allowed me to be fully me.
During my sabbatical, I concluded that being a real estate advisor offered the freedom, flexibility, and financial independence I had been searching for.
I got into CRE during the 2000 dot-com bust, which hit Silicon Valley and the I-880 corridor hard, with significant vacancy in R&D and flex space as dot-com and telecom tenants folded. Since I was just beginning to switch to real estate, the market downturn hardly affected my career transition. In fact, that downturn is a natural backdrop for early-career lessons in negotiation and structuring deals through a distressed market.
During the boom before the dot-com bust, FOMO was prevalent and loan approval was fast and loose; but during the bust, underwriting guidelines tightened, and lenders scrutinized more with banks’ own appraisers. Ensuring a deal made financial sense forced me to run scenario analysis, number crunching, and extra due diligence to prove the fundamentals – which made me a better agent from analyzing the deals the hard but correct way.
The first years in real estate were financially challenging. The Ivy Group startup was bootstrapped using profits from my own real estate investments. My curiosity led to first becoming an appraiser, then joining a residential brokerage firm as a sales agent. I earned only about $19,000 for the first two years, a dramatic contrast to the nearly $200,000, in 1990s money, I had been earning in technology and defense companies.
Nonetheless, I was undeterred since I believed that I could eventually build greater wealth, independence, and long-term opportunity through my own efforts, investments, and skills.
Over time, I discovered that commercial real estate was where my technical abilities, analytical mindset, and entrepreneurial drive intersected to provide the best fit.
After surviving the dot-com bust in 2000, I felt empowered and applied all my prior training, skills, and experience, such as analytical thinking, data systemization, and engineering principles, to CRE investment advisory and brokerage, and to the creation of my own systems and processes for analyzing and tracking sales, purchases, and leases.
Rejections: Perhaps the hardest part of my transition to this new career was the rejections every agent had to endure. I learned to deal with it as an “occupational hazard” that strengthened mental resilience.
Being Bypassed: Unfortunately in real estate, I learned from costly mistakes in earlier years that it is common for people to take advantage of brokers, especially those who naively share too much information.
“Elevator pitch”: In the beginning of my real estate career, doing the “30-second elevator pitch” at networking events was quite daunting since an engineer hardly needed this skill. Over time, with lots of practice, it became easier. Now when someone asks what I do, I respond in less than 5 seconds: “I solve people’s challenges using commercial real estate.” I learned to ask follow-up questions and listen better.
Stomach failures: Not every deal I invested in was successful. There were times when I had to face the reality that making money and losing money are part of real estate investment, regardless of how good I am at CRE. There are factors outside my control. I learn from my mistakes, avoid repeating them, and move on.
Mental resilience: Yes, I was knocked down, backstabbed, used, and rejected, but I always overcame them. The mental resilience I have developed over 26 years in CRE and prior experience has carried me through good times and downturns. You know what, the more I rebound, the tougher I get. I never let any bad situation permanently dim my optimism. I have learned what kind of people are worth my time and expertise.
While in the corporate world, I was also a real estate investor, from 2001 to 2004.
The five years, 2004-2009, I used the profits from my own real estate investments and personal savings to fund The Ivy Group.
The first big break came from one client in 2005. I was first hired to provide advisory services, and it snowballed into a well-paid portfolio management contract. I first met the client from a cold marketing letter – without introduction or connections. He called me, and we started a business relationship. He introduced me to the trustees of his living trust. I was the advisor to his trustees. I managed and advised his portfolio from 2005 until 2012, eventually liquidating it per the requests of the trustees, and disbursing the proceeds to his beneficiaries.
Even though the management contract paid well, I knew I needed to learn the ropes of handling CRE transactions when the portfolio management came to an end.
I started a partnership joint venture under an LLC in 2007, and we bought a 31-acre lot with the potential of building 31 single-family residential homes in Placerville, CA. After obtaining the county entitlement, before we could sell it, the market turned. We were unable to sell it high enough to recoup all the acquisition costs and the “soft” costs of engineering, soil studies, consultants, and permit fees. None of the partners wanted to continue to throw good money into a depreciating asset, so we all decided the best route was to default on the mortgage and allow it to be foreclosed on. My partners and I all lost money.
The 2008 Global Financial Crisis cratered the real estate market. Years of loose lending and securitization of subprime mortgages inflated a housing bubble. Commercial real estate got hit hard. Financing dried up, property values dropped, and many deals collapsed or had to be restructured.
I was fortunately protected in 2008 by the portfolio advisor and management job. At the same time, I was learning the ropes of brokering CRE deals. After the dust settled, I was well prepared to handle CRE sales and leases.
Had I known there was going to be a financial crisis that would tank the real estate market, would I still consider a career change in 2004? Probably yes. Since it was too late to go back to the corporate world, 2008 made me decide to get better at CRE: I was determined to stand out among the crowd by pursuing CCIM (Certified Commercial Investment Member, equivalent to a master’s degree) and SIOR (Senior Industrial Office REALTORS®, equivalent to a PhD degree) designations.
It took me 10 years to finish all the requirements to earn the CCIM designation, and six more years to qualify for SIOR.
Both the dot-com bust and the 2008 crisis have blessed me with valuable lessons and trained me to start on a solid footing in both my personal investment and strategic advisory for my clients.
In January 2020, I was mentally prepared for something catastrophic, with Covid looming. My second daughter was 3 months old. Even though my deals dried up for 6-8 months, financially, my wife’s earnings as the owner of an independent retail pharmacy carried our family through the lockdown period. When the times had been good on the real estate side, we had the foresight to plan for rainy days by purchasing a pharmacy and turning it into a stable source of income. That proved to be a sound decision when COVID-19 hit.
The lockdown period gave me a lot of time to reflect, plan, and prepare.
At the same time, I remained active in the community: I pledged to run 1,000 miles to raise money for the Rotary Club o Fremont. I finished the year 2020 exceeding my goal by running 1,186 miles. I enjoyed making an impact on my community and letting people remember me by my actions.
COVID-19 was a disruption that re-oriented my priority in life – to take care of my growing family and to further pursue SIOR in order to bolster my CRE leadership.
Through disciplined planning, 2021 turned out to be my best year ever: After I sharpened my skills, while the accumulated CRE deals from the year before started to emerge, I was ready.
I do believe that opportunities, or “luck,” favor the prepared. All the time I spent in my life getting the education, skills, and expertise led to opportunities later. I am proud that I take the road less traveled. This is the key to my success in life and career.
In 2000, I founded a boutique CRE brokerage firm, The Ivy Group. I then eventually earned the two highest designations of SIOR and CCIM in the commercial real estate industry.
I had always dreamed of owning a great company. The Ivy Group has grown from a one-person company into one of the top boutique CRE firms in Fremont and Silicon Valley. It is because of our passion for treating our clients with respect and handling their projects with integrity, transparency, and consistency. Our motto is “Above and Beyond.”
A couple of large commercial real estate brokerage firms have approached me to join them, and several residential brokerages have asked me to start their commercial department, but my entrepreneurial bug has always gotten the better of me.
I credit these three macroeconomic downturns, the 2000 dot-com bust, the 2008 financial crisis, and 2020 COVID-19, for instilling in me the disciplined habits for deal structuring, relationship building, and negotiation skills. I learned to creatively hold deals together even when capital disappears. Instead of chasing the hot market and quitting the downturn, I developed the “deals that last” and win-win themes to protect clients at every turn.
The analytical thinking and problem-solving skills honed from prior work were critical for evaluating all kinds of investment scenarios and during negotiations.
To me, leadership means using influence ethically. Even if I was in a different sector, leadership and people skills would still matter in both work and life. It’s how I relate to my kids, my wife, people I know, clients, organizations — all of it.
I also believe that leadership requires practice, development, and intentional use. It is an important responsibility for taking care of others and the community. With service and trust-building, over the past 26 years I gradually grew into leadership positions such as:
Now you know where I came from, why I do what I do, and my passion for helping others become financially successful. You know my setbacks and vision for the future.
I must say that the most humbling, challenging, and joyful work, on a daily basis, is striving to be the best father and husband I could possibly be.
Looking back at my life so far, again, I am so grateful for America, for the opportunities bestowed upon me both to receive my blessings and to give back. Whoever you are, whatever you do, this country offers the best foundation for us to build our future and legacy.
Additionally, here are some more “idiosyncratic traits”:
I hope you get a full picture of me from these two chapters before I dive into the next 11 chapters about various aspects of commercial real estate investment.
Live and learn. My American dream is still unfolding. So is yours!
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The Ivy Group specializes in commercial sales, leasing, and investment advisory across Fremont, Silicon Valley, and the Greater Bay Area. With over 100 years of combined experience, expertise, and designations including SIOR and CCIM, The Ivy Group provides strategic guidance for complex transactions in commercial real estate. When you need to sell, buy, or lease, The Ivy Group is ready to help you reach your goals. Contact us with your next real estate needs.
All information shared here in this article, and in all blogs, case studies, and courses offered by The Ivy Group are for general education only, not tax, legal, or investment advice. Please seek professional advice from tax, accounting, legal, and other professionals.
Copyright © 2026 by Tim Vi Tran, SIOR, CCIM. All rights reserved.
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