A Million-Dollar Lessons on Wealth & Grit | Dan Pascone with Cody Hall | Ep #24

Cody Hall is the founder and CEO of Telehelping, a company that provides virtual and remote support staff across multiple industries. He also hosts a podcast. He describes growing up in what he calls a "very high class of trailer park," feeling like he came into the world owing it something. He joined the military, worked his way up in the Marine Corps into its special operations group, and says that's where opportunity opened up.

After the military, he became the first person in his family to graduate college, earning a management degree at UNC Charlotte. He studied full-time, taking 15 to 18 credit hours, while working 40+ hours a week at Apple, first in sales and then in HR for its data centers.

After 4 years at Apple, Amazon offered Cody 2 jobs: operations manager or HR manager. He says they paid the same on paper, but the HR role was hourly, so it came with overtime, and he was told "you always get overtime at Amazon." He took it, moved to California, and says he hated it. He worked 3 shifts of 12 hours a week at Amazon and spent his days off working with startups, which is how he got into tech and eventually into executive and CEO roles.

The lesson in that story: 2 offers can look equal on paper while the structure of the pay makes them very different. Compare how pay works, not just the headline number.

Cody's first big equity event came at a pharma company valued at about $300 million, where he joined as VP of HR. About 6 months in, the company was acquired. He says he held about 30,000 shares, the acquisition vested everything instantly, and his shares were bought out. He also says getting paid meant first seeing the company through post-acquisition layoffs. He used that time to line up his next role, since being jobless is something he never wants to experience.

He put the proceeds, along with the sale of a firearms manufacturing side business he started in college (which he says he sold to Palmetto [VERIFY: company name]), into rental real estate. He describes a technique of using a VA loan, refinancing the property into a non-VA loan, then using the VA loan again for the next property. VA loans come with rules, including generally requiring you to occupy the home as your primary residence, so confirm any strategy like this with a VA-approved lender. For the tax side of rentals, see our piece on the real estate tax benefits high earners misunderstand.

Cody's next job was at an HR tech startup in Los Angeles that took a $50 million investment and grew from 500 clients to about 5,000. He says the hours wore him down. After a year, he walked out one morning after vesting and went to the doctor, who told him, in his words, that he had the blood pressure of a 70-year-old man with hypertension. He left the job.

He says it was the job plus his personal life. His income was high and so was his spending, including $20,000 vacations to the Maldives. Even the rental income got spent. He was "high income, low cash in the bank" and constantly stressed that he should have more. For a framework on spending well without sabotaging your future, see our 70/20/10 rule.

He traces the pattern to his earliest memory of money: the school book fair, where he had no money to buy even 1 book. That planted a belief that "there's never enough," which showed up as hoarding. Pairing that with a spouse whose default was spending created friction, which he says contributed to that relationship ending. Now, as a dad, he is "huge on reserves."

Cody organizes his money by time horizon:

• Long-term: Real estate and his company. Telehelping also makes strategic private investments in some clients' businesses, including legal, accounting and AI startups.

• Mid-term (5–10 years): Bourbon holdings and blue-chip art, including fractional shares of Picassos held through an LLC. He doesn't plan to hold them forever, just long enough for a good gain.

• Short-term: An equities trading company he started with his former CMO, using half of his CEO exit, where they day trade indices and equities. He calls it the riskiest bucket, and says it sits on a stable foundation, so if it goes to zero, his life is still okay.

The structure is the useful part: reserves and long-term assets first, risk on top. The risk itself is not a model to copy. Day trading, fractional art and private investments can be illiquid, hard to value and can lose most or all of the money invested. We cover the trade-offs in our piece on private equity and alternative investments.

Telehelping grew out of Cody's earlier role as CEO of Octiva, a healthcare company focused on chronically ill patients. It employed about 40 Spanish-speaking nurses in the Philippines. He found he could hire native Spanish speakers in Mexico for about 40% less, so he and his now-wife started Telehelping to move those roles and free up cash flow.

When he left Octiva, whose board had 7 members, due diligence raised the question of whether Telehelping, a related company serving his own company, was at arm's length. He says his contract promised a very large payday, but between resigning early and the Telehelping question, the amount was negotiated down to a smaller, but still substantial, seven-figure payout. He says there was some tax planning involved, which he described as "83(b)-style elections" [VERIFY: an 83(b) election is generally made within 30 days of receiving restricted stock, so this description needs confirming].

He took over Telehelping, shifted it from healthcare toward legal, accounting, finance and other professional services, and now calls his team "acclimation consultants." They teach remote staff how to work for U.S. companies and teach founders how to onboard, delegate and train. His podcast started as a way for his team to understand clients as people. It is now 70+ episodes in, with a focus on understanding entrepreneurs as humans.

Dan closes with quick questions. Cody's answers:

• Coffee or tea: Coffee.
• One meal for life: A burger.
• Tech he can't live without: Firearms, which he says he loves [VERIFY: confirm you want this answer included].
• Favorite quote: "Don't be limited by what other people have said or done," which he attributes to Albert Einstein [VERIFY: attribution].
• Favorite book: The Checklist Manifesto by Atul Gawande.
• Personal hack: "Just get over it." Whatever it is, get over it and move.
• Bucket list item: Being a liquid millionaire. He says he logged in and refreshed his account over and over to make sure the number was still there.
• Challenge that shaped him: Being obsessed with growth. He now focuses on impact, on whose lives his company affects, instead of growth charts.
• Financial milestone: "Never go broke." He says he researches toys like dirt bikes and cars with maybe a 0.01% chance of buying, yet bought a meaningful condo in historic Mexico within days, which he sees as an appreciating asset and an emotional one.
• Advice to his younger self: A joke about marrying fewer times, followed by a sincere note that those relationships, even the hard ones, shaped him.

Cody's story is a case study in 3 things executives often learn the hard way:

• Income is not wealth: A large paycheck can leave you "high income, low cash." What you keep and what you build matters more than what you earn.
• Foundation first, risk second: Cody takes real risks, but from reserves and long-term assets. Decide what you can't afford to lose before you decide what to chase.
• Plan the windfall before it lands: An acquisition can accelerate vesting and put a large taxable event into a single year. The decisions about taxes, reserves, concentration and goals are easier before the money arrives than after.

This is a hypothetical with assumed figures, for illustration only. It is not a projection, a recommendation or a client case, and it does not reflect Cody's numbers.

Say a 45-year-old executive's company is acquired and her unvested equity accelerates: 20,000 shares at an assumed $45 per share, or $900,000 gross. Assume combined federal, state and payroll taxes of 40%, or $360,000, leaving $540,000 net. Before spending a dollar, she assigns it a job:

• Foundation: $180,000 (about 33%) for 12 months of expenses at an assumed $15,000 a month.
• Near-term goals: $120,000 (about 22%) for goals in the next 3–5 years.
• Long-term investments: $180,000 (about 33%), diversified and invested for 10+ years.
• Opportunity sleeve: $60,000 (about 11%), the most she's willing to put into higher-risk ideas, because she can afford to lose it without changing her plan.

Real life adds timing, withholding that may not match the final tax bill, state rules and AMT. Confirm the tax treatment with your CPA before you act.

Cody's time-horizon thinking mirrors how we build portfolios. Life Driven Investing (LDI), our approach to building a portfolio backward from life, organizes your assets into the Four Liquidity Bands: 0–2 years (current needs), 3–5 years (short-term), 6–10 years (mid-term) and 10+ years (long-term). Reserves and near-term needs get funded first, so a rough stretch in the long-term bucket is less likely to force a sale. Enjoying your money is part of the plan too, which we cover in our video on how to enjoy life now without hurting your future.

For executives facing an acquisition, accelerated vesting or a large equity payout, our Equity Compensation Playbook, our structured rules for equity decisions, lays out the tax, concentration and timing questions before the deal closes. Our Quarterly Strategy Rhythm, our ongoing plan updates and decision reviews, keeps the plan current as life changes. We discuss Telehelping here because it is Cody's company. This is education, not an endorsement of any company, product or strategy.

This conversation is for corporate executives and senior leaders in their 40s and 50s, with household income of $500,000 or more and complex compensation such as RSUs, stock options and acquisition payouts, who want to turn a high income into lasting wealth instead of a high lifestyle.

If an acquisition, vesting event or large payout is on your horizon, the planning is easier before the money arrives. A free Wealth Strategy Call is a low-pressure conversation about your equity, tax and cash flow picture. Book a free Wealth Strategy Call.