Investor Retires Early by Creating Multiple Revenue Streams
Sam Dogen, founder of Financial Samurai and author of “Buy This, Not That,” left his investment banking career at 34 after building a portfolio generating $80,000 annually. This decision in 2012 marked the beginning of his journey into early retirement, with his wife following suit in 2015.
However, life had other plans. As their family grew with two children, born in 2017 and 2019, so did their financial needs. Dogen, now 46, expanded his passive income streams to an impressive $380,000 per year before taxes, comfortably supporting his family’s lifestyle in San Francisco. Recently, Dogen made a significant financial decision that altered his retirement status. He sold a portion of his stock and bond holdings to purchase a multimillion-dollar house in cash. This move, while aligning with his family’s goals, reduced his income-producing assets. “By swapping income-producing assets for a house, I basically have a lot more dead money now,” Dogen explains. The result? His passive income no longer covers his family budget, necessitating a return to work. To learn more about his journey, you can read about the early retiree who had $380,000 a year in passive income and heads back to work.
A Calculated Risk
Dogen’s decision to relinquish financial independence was not impulsive but part of a broader family strategy. After his youngest child was born, he committed to being a stay-at-home dad for five years. With his daughter starting full-time school this September, Dogen sees it as an opportune time to pivot.

“I believe the best time to own the nicest home you can afford is when your kids are at home,” he states, explaining the rationale behind the house purchase.
The financial impact is significant. Dogen estimates his nonworking income for 2024 will be around $230,000, sourced from rental properties, investment distributions, and book royalties. This leaves him with a $113,000 shortfall based on his projected expenses for a “realistic and comfortable” lifestyle.
Rebuilding Financial Independence
To bridge this gap, Dogen is pursuing a consulting role, aiming for a 20-hour work week with an estimated salary of $145,000. This arrangement would cover his current shortfall while allowing ample family time.
Looking ahead, Dogen plans to rebuild his passive income streams. He’s considering selling the family’s previous home but is waiting for more favorable market conditions in San Francisco. “We’re past the bottom of the San Francisco real estate downturn,” he observes. “We’re going to pick up over the next several years because of artificial intelligence and technology.” In the interim, renting out the property could yield a net profit of around $40,000 annually, funds that would contribute to rebuilding his investment portfolio. For those exploring additional income opportunities, there are numerous side hustle ideas available that could help supplement earnings.
Lessons in Financial Flexibility
Dogen’s experience underscores the importance of diverse revenue streams in maintaining financial independence. His journey from relying solely on investment income to exploring real estate, writing, and online content creation demonstrates the value of income diversification. This strategy provides a safety net against market fluctuations and changing life circumstances. For those aspiring to financial independence, Dogen’s story offers valuable insights:
1. Diversify income sources beyond traditional investments.
2. Remain flexible and open to adjusting financial strategies as life evolves.
3. Consider the long-term implications of major financial decisions, such as property purchases.
4. Be prepared to re-enter the workforce strategically if circumstances change.
Embracing New Chapters
As Dogen transitions from full-time parenting to seeking new professional opportunities, he remains optimistic. “The more you invest in something, like being a stay-at-home parent, the more you have to fill this void of emptiness once they go to school full-time,” he reflects. This outlook embodies the essence of financial independence – the freedom to make choices aligned with personal and family values, even if it means temporarily stepping away from traditional retirement.
Dogen’s journey reminds us that financial independence is not a fixed destination but a dynamic state requiring continuous reassessment and adaptation. By maintaining diverse income streams, staying flexible, and embracing new opportunities, individuals can navigate life’s changes while working towards long-term financial security and personal fulfillment. For more insights on creating passive income, check out this discussion on Reddit about investing for passive income.

Additionally, for those interested in learning more about effective side hustles, consider watching this informative video that outlines various strategies for generating extra income.
Frequently Asked Questions
How did Sam Dogen achieve early retirement?
Sam Dogen retired early at 34 by building a portfolio that generated $80,000 annually. He expanded his passive income streams significantly over the years to support his family’s lifestyle.
What financial challenges did Dogen face after starting a family?
After having two children, Dogen’s financial needs increased, prompting him to expand his income streams further to $380,000 per year before taxes to comfortably support his family.
Why did Dogen sell part of his investment portfolio?
Dogen sold a portion of his stock and bond holdings to purchase a multimillion-dollar house in cash, which aligned with his family’s goals but reduced his income-producing assets.
What was the impact of Dogen’s house purchase on his finances?
The house purchase led to a shortfall in passive income, meaning Dogen’s passive income no longer covered the family’s budget, requiring him to return to work.
What is Dogen’s plan to address his financial shortfall?
To bridge the $113,000 shortfall, Dogen is pursuing a consulting role aimed at a 20-hour work week, which would provide him an estimated salary of $145,000.
How does Dogen plan to rebuild his passive income streams?
Dogen is considering selling his previous home when market conditions improve and is also looking at renting it out for a net profit of around $40,000 annually to help rebuild his investment portfolio.
What lessons about financial flexibility does Dogen’s experience highlight?
Dogen’s experience emphasizes the importance of diversifying income sources, remaining flexible with financial strategies, considering long-term implications of financial decisions, and being prepared to re-enter the workforce if necessary.
What are some strategies for maintaining financial independence?
Key strategies include diversifying income sources beyond traditional investments, adjusting financial strategies to life changes, and reassessing major financial decisions regularly.
How does Dogen view the transition from full-time parenting to work?
Dogen remains optimistic about transitioning from full-time parenting to professional opportunities, recognizing the emotional void that may arise and the importance of investing in family and personal fulfillment.
What is the essence of financial independence according to Dogen?
Dogen believes financial independence is not a fixed destination but a dynamic state that requires continuous reassessment and adaptation, allowing individuals to make choices aligned with their values.