This interview is with Richard Maize, Investor at Richard Maize Enterprises.

Richard Maize, Investor, Richard Maize Enterprises

Can you tell us about your background in investing, startups, and real estate? What experiences have shaped your expertise in these areas?

I made my first real estate investment in my mid-20s, an apartment building. By 30, I owned over 1,000 apartment units, and now I own property in 20 states! While real estate investing was my first passion, in the last couple of decades I have begun to focus on angel investing for various startups: a PR company, a food truck, and the latest venture, a K-Pop music festival! I like to keep things varied; it makes life interesting. I think over the years I have learned not to put all of your eggs in one basket. If one industry crashes for whatever reason, you still have the others to fall back on.

How did you transition from your early real estate investments to becoming a successful investor across multiple domains? What were some pivotal moments in your career?

My transition from real estate to multi-industry investing wasn’t a sudden pivot; it was a natural evolution. I started in real estate because it gave me control. I could see the asset, run the numbers, and understand the risks. But over time, I realized that the same principles apply across many industries.

One pivotal moment was during a real estate downturn early in my career. I saw investors panic and pull out, but I leaned in. I acquired undervalued properties when others were sitting on the sidelines. That move not only accelerated my growth, it taught me to stay calm when markets shift. That mindset has served me in every investment since.

As my portfolio grew, opportunities started coming from other industries: media, PR, hospitality. I didn’t jump at everything, but I asked myself: Does this align with how I operate? Does the founder have passion and drive? That’s how I got involved in businesses like Richeeze Melts, and how I’ve continued to grow across different spaces without chasing trends.

Success, for me, has always come down to two things: trusting my instincts and never getting complacent. I keep learning, I stay curious, and I only invest where I believe in the people behind the idea.

You’ve mentioned taking calculated risks, like purchasing an apartment building in your 20s. Can you share another instance where you took a significant risk in investing or startups that paid off?

Absolutely. Richeeze Melts, a Los Angeles-based food truck, was one of my first investments outside of real estate, and it had thrived for many reasons, but largely due to the chef and founder who I took a risk on. I saw that he was motivated, hungry, and talented, and I wanted to help his big dream become a reality, and it has!

In your experience, how do the challenges of investing in startups differ from those in real estate? What strategies have you found effective in mitigating risks in each area?

Real estate and startups are two very different animals when it comes to risk. In real estate, you’re dealing with tangible assets: buildings, land, leases. The variables are more predictable. You can underwrite a deal, run comps, and forecast based on historical data. If the numbers work and the location makes sense, you can usually control the outcome.

Startups, on the other hand, are all about intangibles: vision, timing, execution, and most of all, people. You can have a brilliant product and still fail if the team can’t deliver. You can have a great market fit but no runway. The risk profile is much higher, and the margin for error is razor-thin.

My strategy in real estate is to stress-test every deal. I ask: What happens if rent drops, if interest rates rise, if there’s a vacancy spike? I always plan for the worst-case scenario, and if the deal still holds, I move forward.

With startups, my approach is more personal. I invest in people first. I look for founders who are not just smart, but scrappy, adaptable, and honest. I don’t just want to hear the pitch; I want to understand how they handle failure. I also look at burn rate, traction, and whether they truly understand their customer. And if I can’t bring value beyond capital, I usually pass.

The common thread in both? Don’t fall in love with the potential. Be willing to walk away if the fundamentals don’t add up. That mindset has protected me more times than I can count.

You’ve used the 1031 exchange strategy in real estate. Are there similar tax-efficient strategies you’ve employed in startup investing? How do you balance tax considerations with growth potential?

The 1031 exchange is one of the most powerful tools in real estate; it lets you grow your portfolio without getting hit with capital gains each time you sell. Unfortunately, there’s no exact equivalent in startup investing, but there are strategies I use to stay tax-efficient.

For example, I make use of the Qualified Small Business Stock exclusion under Section 1202 of the tax code. If the company qualifies and I hold the stock for at least five years, I can potentially exclude up to $10 million in capital gains. That’s one of the rare startup benefits that rivals a 1031 in terms of tax efficiency.

I also use tax-loss harvesting when early-stage bets don’t work out—writing off losses strategically to offset gains elsewhere. It’s not glamorous, but it’s part of being disciplined. I’m not just focused on how much I make; I’m focused on how much I keep.

That said, I never let the tax tail wag the investment dog. If something has real potential, or if the right founder is at the table, I won’t pass just because it’s not tax-sheltered. For me, it’s always a balance: minimize friction, but never at the expense of long-term upside.

You’ve emphasized the importance of investing in people. Can you share a specific example of when trusting your gut about an entrepreneur or startup team led to a successful investment, despite perhaps unconventional data?

Definitely, with Richeeze Melts that was mainly a gut-instinct investment. At the time, The Grilled Cheese Truck was the big sandwich truck in Los Angeles; they had a huge cult following, and even though our menu was quite different from theirs, I knew there would be significant comparisons made. If people were going to choose Richeeze instead, we would have to really bring something great to the table: great food and upbeat and friendly customer service. The stakes were quite high. But I trusted my gut because I knew Severin (the co-founder and managing partner) had what it takes; something just felt right about it.

Real estate markets can vary greatly by location. How do you approach identifying promising markets for investment, both in real estate and in choosing locations for startup investments?

In real estate, a ‘promising’ market isn’t always the hottest one on paper; it’s the one that’s about to tip. That’s what I’m always looking for. I pay close attention to migration trends, job growth, infrastructure plans, and city-level politics. Are people moving in? Are businesses expanding here? Are there barriers to entry that protect value long-term? I’ve made great returns in markets other people overlooked just because I was paying attention to what was starting to move, not what had already peaked.

Whether it’s property or product, I ask: what’s this area hungry for, and who’s about to meet that need first? If you can spot that alignment early before everyone else sees it, you’re already ahead of the game.

Given your experience across different investment areas, how do you structure your portfolio to balance stability from real estate with the potential high growth from startups?

For me, portfolio structure is all about balance between growth and stability. Real estate is my foundation. It provides steady income, long-term appreciation, and predictable returns. That’s the part of my portfolio that lets me sleep at night.

Startups, on the other hand, are where I take calculated risks. I don’t expect every one to succeed, but I know that one or two big wins can outperform ten traditional deals. The key is to never let your high-risk bets outweigh your long-term anchors. I treat startup investing like a venture fund would: I diversify across industries, stages, and founders, and I assume not all of them will hit.

Structurally, I allocate the majority of my capital to real estate, roughly 70%, because that’s where I have the deepest experience and control. The remaining portion goes to startups and opportunistic plays. I revisit the balance regularly, especially when markets shift or liquidity opens up.

Looking ahead, what emerging trends or technologies do you see as game-changers in the worlds of investing, startups, or real estate? How are you positioning yourself to capitalize on these opportunities?

One of the biggest shifts I see across all sectors is the integration of AI and automation into decision-making and operations. It’s not just about cutting costs; it’s about speeding up insight. In real estate, AI is already helping investors analyze deals faster, model risk scenarios, and predict tenant behavior. That’s only going to accelerate.

In the startup world, AI is leveling the playing field. A solo founder today can do what used to take a 10-person team. That’s changing the types of businesses that are viable and how fast they can scale. I’m paying close attention to founders who know how to use these tools to their advantage.

Another game-changer I’m watching: fractional ownership and tokenization of real assets. The idea that someone can invest in a slice of a building or a revenue-producing asset, without a traditional fund or REIT, is going to reshape accessibility. It’s early but the infrastructure is coming.

How am I positioning myself? By staying open. I’ve been in this long enough to know that you can’t wait until something’s “proven” before you get curious. I spend a lot of time with founders, technologists, and other investors who are working on what’s next. And I always ask myself: what problem are they solving, and what behavior are they betting on? That’s where the opportunity is.

Thanks for sharing your knowledge and expertise. Is there anything else you’d like to add?

That’s all for me! Thank you for the great interview.