How This Wealth Advisor Invests His Own Money
By Luke Sullivan on October 16, 2025
This week, Jake is flying solo in our new Upticks SoloCast series! While our regular Upticks episodes with Jake and Cory are still running strong, we’re rolling out fresh content formats to give you even more insights. Ever wondered how a wealth advisor invests their own money? In this episode, Jake Falcon pulls back the curtain on his personal investment strategies—covering financial planning, cash flow, retirement accounts, and more.
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Read an overview of the episode below
Start with a Living Financial Plan
Jake’s approach begins with a plan that guides decisions without boxing him in. He describes it as dynamic, something to revisit as life and markets evolve. “First off, it all starts with a financial plan,” he says. “In my opinion, no one should be investing any capital without first having a well‑thought‑out, constructed financial plan.” For him, that plan orients every dollar toward what matters most.
He organizes the plan around three pillars: tax planning, retirement goals, and near‑term life objectives. On taxes, the aim is to manage investments in ways that help limit unnecessary drag. On retirement, he targets financial independence with clear savings milestones. And for lifestyle, he maps one‑, three‑, and five‑year goals—home projects, travel, even a potential car—so cash and investments line up with timing and purpose. “It’s something to reflect back on, adjust, pivot, and keep you focused on what’s important to you.”
Cash Flow First: Checking + High‑Yield Savings
Because Jake’s income hits quarterly, he prioritizes liquidity and predictability in his cash flow system. “I only get paid four times a year—January, April, July, and October—so I’ve got to make sure I’ve got enough cash in this checking account to bridge the gap in between payments.” He keeps bill‑pay money in a simple checking account (interest is not the point here) and moves the surplus into a high‑yield savings account to help the idle cash earn more while it waits to be used.
This two‑bucket setup also supports short‑ and intermediate‑term goals. For expenses likely within one to three years, he prefers high‑yield savings, so funds remain accessible and comparatively steady. “I toggle money back and forth between those accounts,” he explains, using the high‑yield option for months he won’t need immediately. The objective is straightforward: keep spending money liquid and let near‑term money work a bit harder—without taking market risk he doesn’t need for short horizons.
The Flexible Middle: A Brokerage Reserve
Beyond cash, Jake maintains a taxable brokerage account as a flexible reserve. He holds a mix that leans toward blue‑chip companies—often with dividends—and may include bonds or other relatively stable positions. “Within my brokerage account, I like to lean towards more blue‑chip stocks that typically pay dividends. I might even have some bonds or something that’s relatively more stable than a high volatile stock.” He views this pool as available for emergencies, business opportunities, or major purchases.
He likes that there are no IRS pre‑retirement withdrawal rules in this account, though he’s clear about the trade‑off: market risk. He also notes that borrowing on margin exists but carries risk and requires caution. Importantly, Jake invests in individual stocks, not funds or annuities, because he prefers direct ownership and fee transparency, supported by Falcon Wealth Advisors’ investment team. “I’m not using any products in my own accounts… no mutual funds, no index funds, and no annuities.”
Long‑Term Growth: Retirement Accounts
For retirement, Jake contributes to a SIMPLE IRA at work and invests with a long runway in mind. “I max that out according to the IRS limits every year… My financial plan says that I’m going to retire at age 70, so at 44 years old, I’ve got plenty of time for the market to fluctuate in that account.” That horizon supports broadly diversified stock exposure, where compounding over decades may help drive growth.
He keeps prior workplace savings in a rollover IRA—separate from current contributions—to keep goals and tracking clean. He and his wife also fund Roth IRAs, favoring growth‑oriented companies (still without speculation). “I do typically lean towards more growth assets… I’m not looking for bonds. I’m not looking for dividends as much.” The appeal is the Roth structure’s tax‑free growth and qualified tax‑free withdrawals later, which can help diversify future tax outcomes.
Triple‑Tax Advantage: Health Savings Account (HSA)
When eligible under a high‑deductible health plan, Jake sees the HSA as a powerful, tax‑efficient tool. “Health Savings Accounts are very powerful. They’re a triple tax benefit,” he says—tax‑deductible contributions, tax‑deferred growth, and tax‑free distributions for qualified medical expenses. He’s building the account and carefully tracking receipts with an eye toward future reimbursement flexibility.
The administrative habit matters here. By saving and organizing qualified medical receipts, retirees may later draw from the HSA tax‑free to offset those past expenses. Jake summarizes the idea with a hypothetical: “If we’ve built up $100,000 in the account and we have $100,000 worth of saved receipts; we’re going to be able to pull all that… and it’ll come out tax free.” Recordkeeping may help unlock that benefit down the road.
Charitable Giving: Donor‑Advised Fund (DAF)
Jake and his wife recently opened a donor‑advised fund to add timing flexibility and potentially improve tax outcomes for their giving. He notes that changes in the tax landscape can affect how deductions work in a given year. “What my plan is, is I’m going to fund a donor advised fund and get more of that deduction this year… so then in [a later year], when the rules change, when we want to make a charitable donation, we can just pull it from our donor advised fund.”
This approach lets them “front‑load” contributions in a year that fits their plan, then recommend grants to charities over time. Jake is careful to add context: if someone is retired with lower adjusted gross income, the calculus may differ. The broader point holds: aligning giving strategy with the financial plan and tax picture may help donations go further for both the donor and the causes they care about.
Looking Ahead: Education and Additional Diversifiers
Jake is considering a 529 plan for future education needs. He notes you can open one before having children, though he prefers to wait until the timing is clearer. The attraction is earmarking dollars for education with potential tax advantages, while keeping the broader plan coherent.
He’s also exploring other diversifiers—private equity, land, or real estate—but remains grounded in simplicity and compounding. “In the meantime, I keep it simple. I let compounding take over for me and my wife, and we revisit that financial plan at least two to four times a year.” Periodic check‑ins help the plan and the portfolio adapt to life changes without overreacting to noise.
Why Alignment Matters
A thread runs through Jake’s choices: alignment between accounts, time horizons, taxes, and goals. He favors direct ownership and clarity on fees, backed by a professional investment team, and avoids products he doesn’t personally use. “If I’m going to sit here and advise my clients, I don’t know how I could… say to buy a product… if me, myself, is not doing the same thing.”
The takeaway isn’t that everyone should mirror Jake’s allocations. It’s that building a coherent system—from checking to HSAs and retirement accounts—may help your money serve your life on purpose. Start with a living plan, choose tools that fit your timeline, and review regularly.
Ready to take control of your financial future? We are here to help you see the difference a well-crafted plan can make. For more insights, resources, and exclusive content, subscribe to Upticks and stay ahead on your path to wealth!
Thank you for tuning in, we hope you have a great week!
