The Tom Dupree Show

Why Tobacco Stocks and Alternative Investments Are Shaking Up Kentucky Retirement Planning Strategies
In this episode of The Financial Hour, Kentucky retirement planning strategists Tom Dupree and Mike Johnson discuss controversial investment strategies that are delivering strong returns for their clients. From tobacco stock investment opportunities to the hidden risks of alternative investments in 401 (k) plans, this discussion reveals why contrarian investing and local financial advisor expertise often outperform Wall Street’s mass-market approach.
Tobacco Stocks Investment: The Contrarian’s Cash CowDespite years of negative sentiment, tobacco stocks continue generating impressive returns through strategic dividend investing. As Tom explains,
“We do have some investments in tobacco stocks. And for years, we’ve been told the category is going away. Don’t touch it. Stay out. But if you looked at the financials of the companies, they were incredibly profitable.”
Why Tobacco Companies Are Evolving Beyond CombustiblesThe tobacco industry is rapidly transforming into diversified nicotine companies, moving away from traditional cigarettes toward:
- Vape products and nicotine pouches
- Heated tobacco alternatives
- Reduced-risk product lines
Key Financial Metrics:
- $8 billion in free cash flow
- $5.5 billion allocated to dividends
- 4-5% volume decline in combustibles offset by growth in alternatives
“The delivery of nicotine is over the long term, almost certainly moving away from what they call combustibles… to vape and pouches,” notes the discussion, highlighting the industry’s strategic pivot.
Market Commentary: Alcohol vs. Nicotine StocksThe discussion reveals fascinating market dynamics between vice stocks:
Declining Alcohol Consumption:
- 56% of US adults reduced alcohol consumption
- Bourbon collectors are facing declining values
- Major distilleries are experiencing significant stock declines
Rising Nicotine Investment Appeal:
- Tariff protection for domestic production
- Strong cash flow generation
- Successful product diversification
Trump’s recent executive order allowing alternative investments in 401k plans creates both opportunities and significant risks for retirement savers. The legislation permits plan sponsors to include:
- Private equity funds
- Cryptocurrency options
- Real estate investment trusts
- Other alternative asset classes
The team identifies critical concerns with private equity in 401k plans:
Major Risk Factors:
- Lack of daily liquidity
- High fee structures
- Limited transparency
- No switching between funds
“The problem with private equity is the lack of liquidity and fees,” Tom emphasizes. “You cannot do switching between a private equity fund and another private equity fund, because they don’t price it daily.”
TIAA Traditional Annuity: The Hidden Retirement TrapFor educators and institutional employees, TIAA Traditional annuities present significant challenges that many don’t discover until retirement.
The 10-Year Walkout Problem- Transfer Payout Annuity: 10 payments over 9 years
- Limited liquidity during the accumulation phase
- Missed growth opportunities compared to CREF funds
“Those were sold for years to educators like it was the safe way to go. And it has cost a lot of people, a lot of appreciation.”
Action Steps for TIAA Traditional Holders:
- Stop new contributions immediately
- Begin the transfer payout annuity process while still employed
- Redirect future contributions to more flexible options
- Plan a liquidity strategy before retirement
The episode contrasts personalized portfolio management with mass-market investment approaches, highlighting key advantages of working with local financial advisors:
Dupree Financial Group’s Investment PhilosophyCore Principles:
- Contrarian investing in undervalued sectors
- Focus on dividend-paying, cash-generating businesses
- Regional expertise in Kentucky-specific planning needs
- Direct access to portfolio managers
“We’ve kind of crafted the portfolio to do dividends and moderate to medium growth. But in order to do that, you have to buy things that people are sometimes pitching out the door,” Tom explains.
Fee-Based Retirement Planning AdvantagesUnlike commission-based advisors, fee-based retirement planning provides:
- Transparent cost structure
- Aligned interests between advisor and client
- Comprehensive portfolio analysis
- Ongoing investment management
Don’t let hidden investment risks derail your retirement plans. Whether you’re dealing with TIAA Traditional complications, exploring alternative investments, or seeking better returns through contrarian strategies, Dupree Financial Group provides the local expertise Kentucky residents need.
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