Learn, and then be bold. Learn as much as you can, have an 80/20 approach to data, but don’t be afraid to make gut decisions and go hard. Indecision or trying multiple things can prevent an acceleration.
In many large cities in the US, there is a crisis caused by a shortage of affordable housing options. This has led to a host of social challenges. In this series called “How We Are Helping To Make Housing More Affordable” we are talking to successful business leaders, real estate leaders, and builders, who share the initiatives they are undertaking to create more affordable housing options in the US.
As a part of this series, we had the pleasure of interviewing Tyler Baldwin.
Tyler Baldwin is Chief Executive Officer at Reali. Since 2018, Tyler has served as Reali’s Chief Revenue Officer and Chief Operating Officer where he led the sales, marketing, and operations teams with a focus on building Reali’s rapidly expanding operations. Prior to joining Reali, Tyler worked for McKinsey & Company and LinkedIn. Tyler holds a Master of Business Administration from Northwestern University and currently resides in the Bay Area with his family.
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory?” What led you to this particular career path?
I began my career in management consulting with Monitor Deloitte and McKinsey advising fortune 500 companies on their growth strategy. Later I joined LinkedIn, where I helped launch two new business lines, holding strategy, operations and sales leadership roles. The theme throughout most of my career has been solving hard problems and launching new businesses.
I have had the fortune of being able to buy a home, sell it and then buy a new one. In each of these three transactions, I had great agents who supported me and my wife throughout; however, I was very surprised at how stressful, expensive and archaic the process was. Several years later, I met Reali co-founder Amit Haller, and he shared with me the vision of Reali transforming real estate to make it simple, stress-free and affordable for the consumer. That really resonated with me and I saw that my professional background solving really complex problems and bringing new products to market could help solve the problem I had personally experienced as a consumer.
Can you share the most interesting story that happened to you since you began your career?
I joined LinkedIn in 2011 to help launch the Sales Navigator business line (a tool for Sales Reps to help them prospect). I joined the team as its fifth hire in an operations and strategy role. I helped scale the business to hundreds of people and to nine digits in revenue in just several years. Now roll the clock forward a decade later to 2021 and sales has been fundamentally changed. Gone are the days of a sales rep making a cold call. Practically every top sales rep in the B2B world is using this tool. I’m proud to see that the foundation I helped build transformed an entire industry.
Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?
I’ve been fortunate in my career where I’ve had the opportunity to work in really good companies and have had great managers. I spent my early career in consulting and corporate strategy, expanding my skill set, learning to be a good problem solver and gaining exposure to many different industries and functions. After about ten years, I reached a point where I wanted to specialize — I felt I could only be a generalist for so long. I looked to identify a role that I wanted and ultimately set my sights on becoming a General Manager with P&L responsibility. Once I had my north star, my focus shifted to what that skill set required in relation to where I was.
I was very deliberate in my process and realized that I actually had a pretty big gap in my resume. I was strong on strategy and operations, but lacked sales leadership, which is vital as a GM because they own the revenue number. In order to go forward, I realized I needed to take a couple steps back to invest in a new skill set. I went from managing a global function to leading a small team of just six sales reps because I realized that in order to get where I wanted to go, I needed to broaden the base of my pyramid, acquire a new skill set and develop it. Three years later, I had a much more well-rounded skill set and was eligible for senior executive and general manager roles because I was no longer just a strategy or operations guy.
My advice is to be deliberate about where you want to go. Focus on the skills that are necessary and be patient and be willing to invest in yourself.
None of us are able to achieve success without some help along the way. Is there a particular person to whom you are grateful who helped get you to where you are? Can you share a story about that?
Mike Derezin at LinkedIn had a profound influence on my career. He was the Head of Sales when I was the head of operations and strategy for the Sales Navigator business at LinkedIn. He is a brilliant strategic thinker and entrepreneur; however, where he excels (and what I personally try to emulate) is he thinks about strategy with both heart and mind — it’s not a pure business strategy, but also a people strategy. He was very conscientious about building culture, values and purpose. Because people were so passionate about what we were doing and how we were going about it (living our values and culture), they worked harder than many other teams I’ve been a part of in the past. And, we had fun in process and truly transformed an industry with what we brought to market under Mike’s leadership.
Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?
Endurance by Alfred Lansing. This is a story about Ernest Shackleton who led a failed expedition to Antarctica. In 1915 Shackleton led a voyage to cross Antarctica and within days of reaching the continent, their ship was frozen in the ice until it was crushed by the ice, leaving 28 men stranded with only three lifeboats. For twenty months Shackleton and his crew fought for survival and struggled to get rescued. Eventually they were, and not a single man was lost, despite incredible adversity. What inspired me about Shackleton’s approach was his strategy — he knew the key to survival and rescue was not physical (e.g. surviving the cold, getting food, etc.). It was mental. He was incredibly deliberate about building the morale of the crew and spent more time thinking about their mental well-being than anything else.
This resonates with me because in my experience building startups, I’ve found that developing culture, values, and helping every employee feel part of our mission is absolutely foundational to the success of a company.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
We have all heard the adage, “The grass is always greener on the other side.” Well, I like to modify that to “If the grass is greener on the other side, water the grass underneath your feet.” It’s very easy to compare and feel that someone else is doing better than you or maybe a different job or another company would be better. But I would much rather spend my time and effort trying to make my current situation better and watering the grass underneath my feet rather than worrying about what the grass looks like elsewhere.
Ok super. Let’s now shift to the main part of our discussion about the shortage of affordable housing. Lack of affordable housing has been a problem for a long time in the United States. But it seems that it has gotten a lot worse over the past five years, particularly in the large cities. I know this is a huge topic, but for the benefit of our readers can you briefly explain to our readers what brought us to this place? Where did this crisis come from?
Although Reali is only focused on the housing market within California, the same factors have impacted most of the country in the same way. Since the end of the Great Recession there has been an appetite for housing where demand has greatly outpaced supply. This, paired with historically low inventory and loan interest rates, have combined to cause pricing to skyrocket over the past five years. These increases in pricing have had a significant impact in larger cities where consumers are forced to be perpetual renters, live in multi-generational households or move further away where affordable housing is more likely. Initially, many thought COVID would be a catalyst that would certainly slow down the price momentum given its impact to the economy. However, in California alone, we’ve seen the median sales price in the state surpass the 800,000 dollars level when in 2018 it was still under 600,000 dollars. Unfortunately, this has led to an increasing number of consumers’ purchasing power eroding before their eyes, pushing the American Dream further out of reach.
Can you describe to our readers how your work is making an impact to address this crisis? Can you share some of the initiatives you are leading to help correct this issue?
Although we can’t impact housing prices directly, we have addressed more affordable options for buying and selling homes through our various pricing structures and cash rebate offers for home buyers. For buyers, we offer a cash rebate of up to 1% of the price of the home if they work with a Reali agent. For sellers, we have low priced listing options of 1 to 2% compared to the traditional listing fee. We’ve also introduced Cash Offer and Trade-In programs that provide more opportunities for success in competing against all-cash buyers and investors. Other initiatives that we’re currently exploring are discounts on the bundling of certain services like real estate and loans.
Can you share something about your work that makes you most proud? Is there a particular story or incident that you found most uplifting?
What’s made me most proud at Reali is the manifestation of our vision and our mission. Our mission is delighting homeowners at every stage of their lives. Several weeks ago, one of our agents shared a video of her clients — a husband and wife — who she’d been working with for over a year to get a home. In this market, just winning a home is almost impossible. After numerous offers, their offer had been accepted. In the video, the husband tells his wife they won the house and they both broke down in tears. The amount of joy that they felt for winning a home was so moving. We’re not just building a widget to make someone three percent more productive. We are helping our clients and their families to find a home. It’s amazingly gratifying that what Reali is doing is not just about making money, we’re impacting people’s lives in a very personal way.
In your opinion, what should other home builders and residential real estate companies do to further address these problems?
As an industry, real estate professionals at the local, state and national level need to continue focusing on programs and initiatives that create more affordable housing opportunities. The National Association of Realtors has significant influence in Washington D.C. and should continue to lobby for legislation that encourages more innovative policies on creating affordable housing. They have even acknowledged that the “state of America’s housing stock is dire” and ‘’a once in a generation” response is needed to address the decades of underinvestment and underbuilding in the housing market.
Can you share three things that the community and society can do to help you address the root of this crisis? Can you give some examples?
First, communities need to prioritize the development of homeless shelters and other similar tiny home developments/ADU’s for those displaced from financial hardship. Second, we need to get behind petitions and other lobbying of local and state politicians to prioritize measures that directly support more affordable housing, such as pushing for an increase in the % of BMR (below market rate) units that a developer is required to offer to the public. A third idea is that communities should support strong neighborhood initiatives that push for affordable housing such as “Habitat for Humanity.”
If you had the power to influence legislation, are there laws which you would like to see introduced that might help you in your work?
We should consider zoning changes to certain questionable neighborhood districts (where blight and other challenges exist) that require developers to offer more incentives toward investment, such as “opportunity zones” similar to what was established in New Orleans after Hurricane Katrina and other natural disasters. Those hard-hit wildfire areas along the West Coast need as much federal aid as possible to help bring back communities where insurance claims fall short for rebuilding.
What are your “3 things I wish someone told me when I first started leading my company” and why? Please share a story or example for each.
- Learn, and then be bold. Learn as much as you can, have an 80/20 approach to data, but don’t be afraid to make gut decisions and go hard. Indecision or trying multiple things can prevent an acceleration.
- Focus on fewer things. Many startups that die don’t die because of a lack of a good idea. They die because there are too many ideas. Focus on the two or three things that are going to move the needle and do them really well.
- Listen. In a leadership role, listen first and speak last. Rather than providing direction and waiting for people to confirm it, take all ideas on the table into consideration and make an informed decision.
You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
Let’s start a movement called “pronoia.” It’s the opposite of paranoia. You have to assume people are saying positive things behind your back, rather than negative. The world would be a very, very different place and companies and their cultures would be more successful if everyone just assumed positive intent versus negative. One of our core values at Reali is to be compassionate. The foundation of compassion is empathy, listening and again assuming positive intent. I want people to be “pronoid” instead of paranoid, if that’s a word.
Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂
I would love to speak with Laszlo Bock, who is Google’s former Senior Vice President of People Operations. What’s interesting to me about him is that Google not only disrupted search (and many other industries) from a technology perspective, but with their innovative approaches to attracting and retaining talent, they disrupted human resources policies and approaches that are now foundational to Silicon Valley culture. How many companies think about culture now came from a lot of the things that Google and Laszlo were doing. I would love to sit down and ask him how he did what he did and what lessons he learned along the way.
How can our readers further follow your work online?
Please visit Reali.com.
This was very meaningful, thank you so much, and we wish you only continued success.




