Q4 is here, which means it’s time to start planning for 2026. I plan early so I can be proactive and launch into the new year with a clear game plan. January 1st hits hard and fast after the holidays.

Every year, I review what worked and what didn’t. I look at the big market shifts and ask myself: how should I adapt? 

When I evaluate my progress, I focus on two areas:

• Entrepreneurial Journey: Where I’m making money as an entrepreneur
• Investing Thesis: How I deploy that capital—my strategic framework for where and how to invest based on market conditions, expertise, and risk tolerance

Let me walk you through my journey—not just the wins, but the lessons that shaped how I think about investing today.

Rates started rising in 2022, signaling a major market shift. I’ve learned from experience to pivot when markets change, so I began adjusting both my investing strategy and entrepreneurial focus. Since real estate moves slowly, that pivot is still ongoing. I’m sharing these lessons to help you navigate your own transitions, whether as an investor, entrepreneur, or both.

Watch the YouTube Video https://youtu.be/98D_dY6YAOo Phase 1: The Entrepreneurial Beginning (2002-2009)

I was a sophomore at Virginia Tech when the entrepreneurial bug bit me hard. That launched me into an early tech and online marketing business that did incredibly well.

I learned how to run a business, developed money-making skills, and generated significant active income. But I made critical mistakes:

• I reinvested too much back into the business instead of diversifying into non-correlated assets
• I had lifestyle inflation and spent way more than I needed to
• When I did have money to invest, I focused on day trading stocks and foreign currency exchange

Like most people who try day trading, I was not successful at it. I didn’t lose money, but I didn’t make any money either. Worse, I realized it was basically a job—my money wasn’t working hard unless I was actively working. I wasn’t really investing. After a couple of years, all I had to show for it was worse eyesight from staring at computer monitors.

Like many entrepreneurs, Rich Dad Poor Dad was my first business book. That’s what put real estate on my radar as the path to building wealth. It was time to make that pivot.

Phase 2: The Transition Years (2009-2011)

The Great Financial Crisis hit, and even though I wasn’t in real estate, my business felt the ripple effects. Several factors converged:

• Industry headwinds hit us hard
• Business partnership issues emerged
• The broader economic crisis created challenges

All of this led to my income starting to fall. We had momentum and high profit margins, but not anymore.

That’s when I learned my next key lesson: every business opportunity, every investment opportunity has a life cycle or a sweet spot for where you are in the cycle. Every opportunity eventually ends, so ride it well while it’s great and move on when it’s time. My big mistake was taking too long to pivot.

I was doing a full pivot, creating my new investing thesis and entrepreneurial journey—both in real estate.

In 2010, I started looking for my first deal. In January 2011, I bought my first house hack—a foreclosure at one-third of the peak price with creative financing: zero down, 5% fixed rate over 15 years.

The success of that first deal gave me the belief that I could really excel in real estate. I knew the next real estate cycle was about to begin. In the stock market, you can’t make anything happen – you’re never a part of it, you’re just reacting to news. In real estate, I could take a leading role and actually make deals happen.

So I went all-in on real estate.

Phase 3: Building the Rental Portfolio (2011-2019)

My gut said the next market cycle was beginning. Prices dropped so much that they only had one way to go—UP.

My investing thesis was simple: buy rentals. I was buying rentals, doing cash-out refis, and doing 1031 exchanges to scale my portfolio.

As an entrepreneur, I launched my brokerage, Envision Advisors. I had figured out how to buy rentals and scale my portfolio—now I helped other investors do the same thing.

Both as an investor and entrepreneur, I rode Denver and Colorado’s amazing growth wave. Prices and rents were growing at a fast pace.

Here’s the crucial difference from my early career: In my first business, I made money but invested poorly. This time, I made money AND invested wisely. This created my next “good problem”—significant net worth growth with high concentration in Denver metro residential real estate.

Phase 4: Real Estate Diversification (2019-2022)

By the late 2010s, I had built significant net worth concentrated in Denver residential real estate. But several factors converged that made me rethink my strategy:

• Numbers were getting harder to make work in Denver
• My life was getting busier as an entrepreneur with a growing young family
• I was no longer getting amazing returns on my active hustle

My first focus for diversification was geographic—outside of Colorado.

I’m not a fan of out-of-state investing. I had seen too many people get chewed up by out-of-state deals. They were either hands-off and got their butts kicked, or they regularly traveled to those markets (vacation, business, family) and built insider knowledge. I couldn’t replicate my Denver knowledge and network elsewhere. I had no desire or connections to travel to markets where the rental numbers made sense. Syndications gave me the geographic diversification I needed without the out-of-state landlord headaches.

In 2019, I made my first LP investment in a multifamily syndication. I gradually increased my allocation to passive deals—primarily multifamily and debt funds in Denver and the Midwest—while continuing to buy select rentals in Denver.

Phase 5: Pivot and Global Portfolio Diversification (2022-2025)

Rates started rising in 2022 and I knew it was time to pivot again. Before I tell you what I did, there are two key principles I focused on:

Principle #1: Ride the Big F***ing Trends

If I could only have one investment principle, it would be this: ride the big f***ing trends.

Looking back at my career, my biggest wins came when I aligned with massive growth waves:

• Early internet boom (Phase 1): My first business generated significant revenue riding this trend
• Denver rental explosion (Phase 3): Built wealth as both investor and entrepreneur

Those periods generated the most revenue, with the least friction, and were frankly the most fun. When you’re paddling downstream with the current, everything moves faster and easier.

The flip side? When I’ve fought trends or ignored market shifts, I’ve struggled. I’ve learned the hard way: growth is your friend, and fighting the current is exhausting.

In 2022, commercial real estate was heading for a crash. Rate increases would pressure residential prices, but commercial was going to feel real pain—their 2008 moment. Distressed assets create the best buying opportunities. I had capital to deploy, strong connections in the space, and the perfect vehicle to access these deals: passive LP investments. The pain was just beginning.

How I Changed My Investing Thesis

Applying this principle, I made a fundamental shift: I stopped buying rentals, started investing in passive deals, and began selling some of my rentals.

This transition delivered exactly what I hoped for:

• Increased Cash Flow: Despite selling properties, my overall cash flow increased through passive investments
• Freed Up Bandwidth: Even with property managers, I still needed to manage the managers and handle asset management. Now I had that mental bandwidth back
• Simplified Operations: Just this year I closed down 3 LLCs and eliminated multiple bookkeeping headaches
• Access to Better Deals: I kept seeing syndication opportunities and thinking “there’s no way I can do that on my own.” Now I could participate

Was it perfect? Nope. I caught a couple of “falling knives” as the commercial market turned. But I’m in a far better position than if I’d kept those rentals. In hindsight, I should have sold everything and held more cash before deploying. At the time, it felt scary—plenty of people thought I was crazy for selling rentals with sub-4% debt. But the transition worked.

The investing pivot worked. But Envision Advisors helped investors buy rentals, and I wasn’t buying rentals anymore—I was investing passively because that was the next big f***ing trend. I needed a new business model that stacked with my new investing thesis: Property Llama Capital.

Principle #2: The Stacking Philosophy

Identifying the trend is step one. Step two is stacking everything around it.

Here’s my core theory: find the best investment opportunities, then build a business around that same trend. When you align market trends with your skills, interests, and business opportunities, you create exponential effects. That’s the 1+1+1 = 9 result.

You may or may not be an entrepreneur looking to build a business, but you have opportunities, skills, connections, and resources that allow you to stack. Whether you’re W2 or self-employed, I encourage you to identify how you can create your own stack based on your unique situation.

Phase 3 was perfect stacking: I was buying rentals (investing), running Envision Advisors (business), and the Denver rental market was booming (trend). Everything aligned. It generated revenue with minimal friction, was genuinely fun and we helped hundreds of clients buy rentals for their financial success. 

Phase 5 is stacking again (2022-Present): Here’s how it comes together in the current market shift:

• The Trend: Commercial real estate distress + growing demand for passive investing opportunities. Direct ownership of these larger commercial assets is much harder than residential due to price points—many are in the 7 or 8 figures+—making passive investing an easier way to access them. Plus, regulatory frameworks have received significant clarity as the market has matured.
• My Skills: 15+ years of real estate investing, deal structuring, investor education, marketplace building, and a strong network of operators and investors
• The Business: Envision Advisors was the right business for investors buying directly-owned rental properties, but not for passive investing. To help investors access these opportunities, we created Property Llama Capital to connect them with vetted passive deals they couldn’t access on their own.

So far Property Llama Capital has helped over 100 investors access these opportunities—a huge privilege that also validates this approach.

I’m investing alongside my investors in deals I’m excited about. They get access to vetted deals they couldn’t find on their own, and because we’re writing 7 or 8 figure checks as a group, we get better economics. When you stack trends, skills, interests, and business opportunities, it’s more fun AND more profitable.

Present Day: The Next Evolution (2025 and Beyond)

The pivot is working—both as an investor and entrepreneur. The direction is set, the trends are validated, and the results confirm I’m on the right path. Now it’s about the next evolution of my investing thesis: diversifying beyond real estate.

I’m currently about 75-80% real estate across all my investments. Plus, my businesses are built around real estate—Property Llama and Property Llama Capital. That’s a lot of concentration risk. Time for a global portfolio rebalance.

Here’s how I’m rebalancing:

My Portfolio Allocation Strategy

Real Estate (55% Allocation):

The biggest rebalance I want to do within real estate is capital stack diversification.

The capital stack is your position in a deal—are you an equity owner or a lender? When I was buying rentals and investing in syndications, the vast majority had been on the equity side.

A few years ago, I started investing in debt funds to be on the lender side. This checks all the boxes for what I’m looking for:

• Double-digit cash flow – debt funds are paying 10%+ returns, which is the best cash flow in the current market cycle
• Fully passive – no operational headaches like direct ownership
• Diversified risk – my investment spreads across 50-100+ loans, not one deal
• Senior debt protection – first position means lower risk of capital loss
• Market cycle advantage – in distressed markets, lenders have the upper hand

I’m about 85% equity right now and 15% debt funds. I want to shift to 50% equity and 50% debt. Why? To maximize cash flow and preserve capital. Early in wealth building, you chase upside. Later, you protect what you’ve built while generating income. I still want growth, but I want better balance—think of it like a 50/50 stocks and bonds allocation, but in real estate.

This 50/50 rebalance will take 3-5 years. The rentals I still own have great debt and cash flow, but it’s a horrible time to sell—I’m not leaving money on the table. Many of my syndication investments need to go full term before I can recycle that capital. In the meantime, the new money I’m deploying today goes primarily toward debt funds.

The Contrarian Play: Denver is Back on My Radar

There’s a lot of pain in Denver real estate right now. Everyone has negative sentiment, myself included. But that reminds me of the Buffett quote: “Be fearful when others are greedy and be greedy when others are fearful.”

The previous market cycle saw double-digit annual price and rent growth in Denver. That pace wasn’t sustainable. Growth has slowed or reversed. Meanwhile, property taxes jumped, insurance costs doubled, operating expenses climbed, and new legislation made it tougher and more expensive to operate rentals.

But this is where opportunities show up.

Case in point: a friend just bought a 10-unit building in Congress Park for around $95,000 a door. That’s 2018 pricing! At these prices, I see a lot more upside than downside.

I recently partnered with a hard money lender expanding into Denver. For the first time, I’m underwriting deals as the lender instead of the borrower. The lender’s perspective reveals the real numbers, the actual distress, and where the opportunities are. It gave me even more confidence in the lending side and reignited my interest in Denver, along with the distressed multifamily. 

I’ve been actively investing on the lending side, but haven’t made equity investments in Denver recently. That may be changing. Pain equals opportunity.

Public Markets (35% Allocation):

I’m shifting significant capital to public markets for three reasons: ride the Big F***ing Trends outside of real estate, reduce real estate concentration risk, and increase liquidity.

Why the liquidity focus? The 2008 Great Financial Crisis taught me the importance of liquid reserves. I’ve maintained that discipline, but like most real estate investors and entrepreneurs, the last few years have reduced my liquidity. I’m building it back up, specifically in non-retirement accounts for better liquidity. Plus, I love that stocks hit my checking account within days.

I’ve traditionally followed Warren Buffett’s approach. Warren Buffett recommends 90% S&P 500 and 10% cash. I’ve been around 90% S&P, 2-3% cash, and the rest some fun money. That’s changing.

My new allocation:

• 60% broad market (S&P 500, total market funds)
• 40% trend plays (sectors below)

Remember my Principle #1: ride the Big F***ing Trends? The biggest trends outside of real estate right now are AI, crypto, and blockchain.

But I don’t have the insider knowledge and connections in these spaces like I do in real estate. Key lesson from private investing: when you lack deep expertise and strong networks, invest through public markets instead of trying to pick private deals.

The big trends I’m targeting:

• AI Infrastructure – data centers, semiconductors, cloud services
• Energy and Nuclear – demand explosion from AI and manufacturing onshoring
• Cryptocurrency – Bitcoin (90% of crypto allocation) through Fidelity’s ETF (FBTC), small positions in Ethereum and Solana
• Blockchain Technology and Infrastructure – separate from pure crypto plays
• Tech – larger established players (Google, Microsoft, etc.) and large and medium cap tech-heavy ETFs
• Gold – I never owned gold before this year, but I’m glad I started buying positions.

Most positions are through sector ETFs with select individual stocks.

Cash (5% Allocation):

Operating reserves, portfolio rebalancing cushion, and dry powder for opportunistic deals. This isn’t personal emergency savings—it’s investment capital sitting in checking accounts, high-yield savings, and short-term Treasury bills. Safe and liquid, ready to deploy (or cover rental properties!)

Opportunistic Investments (5% Allocation):

Unique opportunities across different asset classes—businesses, alternative investments, and deals that come through my network and expertise.

This is a combo of fun money and “invest to learn” capital. If there’s something I’m interested in, I only really pay attention when I have real money invested. It’s how I learn about new asset classes, test operators, and explore opportunities outside my core strategy. Some work out, some don’t, but overall I make money and get a great education. Oftentimes I’m reminded to stay focused on my core strategies!

Maximizing Tax-Advantaged Savings: My Solo 401k Strategy

In 2021, I opened a self-directed Solo 401k and have contributed money and rolled over IRA funds. This has become a crucial part of my investment strategy—allowing me to invest in real estate deals with tax-deferred or tax-free growth.

When I was buying rental properties, I looked at the numbers as both a rental property owner and a broker. The numbers weren’t great for buying rentals in self-directed accounts. Plus, there were stipulations around investing in rental properties through self-directed accounts that made it hard to make it worthwhile.

But I’ve learned there are two biggest opportunities in Solo 401ks or self-directed IRAs:

1. Real Estate Partnerships and Syndications: You can invest in real estate partnerships, syndications, and passive funds without all the restrictions and harder debt requirements (non-recourse loans, higher rates). This includes debt funds, apartment syndications, and alternative assets. All the benefits of real estate investing with none of the rental property restrictions.

2. Private Lending: Rather than using the IRA to buy a property, successful investors I know use their IRA to lend money to flippers and projects—making individual notes and earning consistent returns. Reflecting on the past market cycle, while I couldn’t make buying rentals through my 401k make sense, I wish I had lent money instead.

I’m focused on number one. While I love private lending, I’m doing that through investing in real estate debt funds rather than lending directly myself. I like debt funds for the diversification and added due diligence they provide—my investment spreads across 50-100+ loans rather than lending to one borrower.

A key shift in my strategy: A couple years ago, I started contributing as Roth instead of traditional pre-tax contributions. I’m paying taxes today for tax-free growth later. My thoughts? I can consistently generate 10%+ returns in these accounts, which makes paying taxes upfront worth it. Plus, I expect tax brackets will be higher when I retire—combination of hopefully more personal success and the government raising tax rates.

I’d highly encourage you to explore self-directed IRAs or Solo 401ks if you’re self-employed or have side business income. The ability to invest in passive real estate deals with tax advantages is a game-changer.

Who, Not How

One of my biggest mindset shifts has been moving from “How do I do this?” to “Who can do this better than me?”

In my first business, everything was about how. How do I build this? How do I scale it? How do I fix it? I was hands-on with everything.

When I got into real estate, I focused on a combination of both. I figured out the HOW—where I brought exceptional, high dollar-per-hour value. Then I found the WHO’s for everything else.

I encourage everyone to ask this question: What’s worthwhile in your portfolio and business that you should handle yourself versus finding the right WHO? Focus on your unique value. Delegate or partner on the rest.

I’m always open to new connections, opportunities, and collaboration. Reach out if there’s a way we can work together.

Want to dive deeper into this concept? Read Dan Sullivan’s book “Who Not How.”

Closing Thoughts

Every year, I go through this exercise. What worked? What didn’t? Where’s the market heading? Then I focus on optimizing my portfolio accordingly and updating my investing thesis.

I encourage you to do the same.