Table of Contents
Two entrepreneurs who made millions in their 30s reveal the unexpected emotional toll of stepping away from work, the anxiety of living off investments, and why money can't replace the purpose you get from building something meaningful.
Timeline Overview
- 03:30–08:13 — How Ryan and Jeff Made Their Money: Ryan's journey from side-hustle app development to $30M exit, Jeff's series of $5M businesses and investment epiphany
- 08:13–11:25 — Why They Decided to Step Away: The "lottery winner" mentality, realizing investments outperformed work income, and choosing freedom over more money
- 11:25–16:50 — The Feeling of Loss: Identity crisis after selling, grief over losing purpose and community, missing the grind and addiction to building
- 16:50–18:45 — Facing the "What's Next" Pressure: External expectations from friends and family, the athlete analogy, and learning to ignore score-keeping mentality
- 18:45–21:50 — Finding New Passion and Purpose: Ryan's "job to make life awesome" philosophy, creating experiences, and Jeff's passion projects providing fulfillment
- 21:50–26:25 — Ryan's Financial Advisory Approach: 60/40 portfolio strategy, importance of boring investments, and psychological burden of managing large sums
- 26:25–30:19 — Stock Market Anxiety Reality: The negative feelings of losses vs. gains, complexity-induced stress, and why simple index funds win
- 30:19–end — Future Work Considerations: Whether retirement is permanent, the freedom to return, and balancing spending now vs. saving for later
Key Takeaways
- Early retirement often triggers an identity crisis and grief period lasting 6-8 months as your self-worth was tied to work output and hustle mentality
- The loss of community and purpose can be as significant as losing income - you're no longer invited to entrepreneur dinners or needed by teams
- External pressure to "do something next" creates unnecessary stress - retirement should be about freedom, including freedom from others' expectations
- Managing large investment portfolios becomes surprisingly stressful and time-consuming, making simple 80/20 index fund approaches more psychologically sustainable
- The anxiety from investment losses often outweighs the joy from gains, creating constant portfolio-checking and market obsession that reduces quality of life
- Having enough money to retire early requires a shift from "making money" to "making life awesome" - actively designing experiences and relationships
- Early retirees often relocate to areas with more schedule flexibility since most peers are still working traditional careers
- Retirement doesn't have to be permanent - you can return to work if you find something truly compelling or miss the building process
- The "enough" number is deeply personal, but many find $10-20M provides sufficient security while allowing meaningful spending without fear
- Successful early retirement requires intentional planning for what life looks like when your calendar only has one call on it
The Identity Crisis Nobody Warns You About
When Ryan sold his company for over $30 million, he expected to feel relief and freedom. Instead, he felt like he was grieving. For the first six to eight months after stepping away, he struggled with what he calls "the loss period" - a psychological adjustment that caught him completely off guard.
The problem wasn't financial. With $20 million after taxes and other obligations, Ryan had achieved what most people would consider the ultimate goal: financial independence in his early 30s. The issue was deeper and more fundamental - his entire sense of self-worth had been built around how hard he worked.
"My self-worth was based in how hard I worked on something, like how many hours I put into something, how many times I think about it, how many podcasts I listened to," Ryan explains. "I didn't have that anymore and I was searching for that next kind of grind or addiction to work on something."
This identity crisis is common among high-achieving entrepreneurs who retire early. The personality traits that enable someone to build a business worth tens of millions - intense drive, action orientation, ambitious goal-setting - don't simply disappear when you no longer need to work. Instead, they can turn inward and create anxiety about whether you're still the same person without the external validation that work provides.
Jeff experienced something similar when he sold his family business years earlier. "It was the weirdest experience," he recalls. "You go from literally being the center of attention, everybody needing you, wanting you, your phone blowing up, all this attention on you, and then you sign papers and you just walk away."
The transition feels especially jarring because successful entrepreneurs often sacrifice other aspects of their lives - relationships, hobbies, health, community involvement - to focus intensively on building their companies. When that central organizing principle disappears, there's suddenly a void where structure and purpose used to be.
This adjustment period isn't just about missing work itself. It's about missing the version of yourself that work enabled you to be: decisive, important, constantly learning and growing, surrounded by people who depended on your judgment. Without that framework, many early retirees report feeling lost, soft, or like they're wasting their potential.
The Community You Lose When You Stop Playing the Game
Beyond the personal identity crisis, early retirement also means losing access to communities and social circles that were built around shared professional experiences. This social isolation can be particularly difficult for entrepreneurs who are used to being surrounded by other ambitious, driven people.
Jeff notices this immediately: "While I go to a lot of events, I'm no longer invited to those same dinners and groups that other business owners and entrepreneurs go to." When you're not actively building something, you lose your ticket to the conversations and gatherings where people discuss challenges, celebrate wins, and support each other through difficult decisions.
This exclusion isn't necessarily intentional or malicious. It's natural that working entrepreneurs want to spend time with others who understand their current struggles and can offer relevant advice. But for someone who has stepped away, it can feel like being removed from a community that had become central to their social identity.
The timing compounds this challenge. People who retire in their 30s or early 40s are typically much younger than traditional retirees, but also out of phase with their age-matched peers who are still in the thick of building their careers. This creates a unique form of social displacement where you're too young for retirement communities but no longer aligned with the professional communities of your generation.
Jeff has found that location becomes crucial: "I think there are only a few places that one can exist with such freedom and not get a little sad, where you can live in a town or environment with people that have schedule flexibility." Major metropolitan areas like New York tend to have more people with non-traditional schedules - freelancers, entrepreneurs, investors, creatives - who can meet for lunch on a Tuesday or take spontaneous trips.
The solution often requires actively building new types of relationships and finding communities organized around interests rather than professional status. But this transition takes time and intentional effort, adding another layer of work to what was supposed to be a period of freedom.
The External Pressure of "What's Next?"
One of the most persistent challenges early retirees face is the constant question from friends, family, and professional contacts: "What's next?" This seemingly innocent inquiry can create significant psychological pressure, especially when it comes from people you respect who assume you must be planning another venture.
The pressure mirrors what happens to successful athletes after winning championships or ending their careers. Within days or weeks of achieving their ultimate goal, they're immediately asked about their next challenge. For entrepreneurs, this creates an implicit expectation that stepping away from work is temporary, that you should be planning your comeback or next big idea.
Ryan has learned to reframe this pressure: "I try to default to they're just asking to be nice or they're just trying to make conversation." But he acknowledges that it can feel like people only value you for what you're building next, rather than appreciating that stepping away might be a conscious choice worth respecting.
The external pressure becomes particularly problematic when it causes people to start new ventures for the wrong reasons. "Some people like 'I'm just going to start another company because I don't know, I don't have anything else to do and I'm good at it,'" Ryan observes. "There's no reason they're doing this - they're just doing it because they maybe haven't sat long enough with the uncomfortable feeling of what else could there be."
This rush back into entrepreneurship often stems from avoiding the discomfort of not having a clear next step. Society has trained us to think of life as a scoreboard where efficiency in reaching the next milestone matters. But early retirement should provide freedom from that scoreboard mentality, including the freedom to take years figuring out what genuinely interests you rather than defaulting to what you're already good at.
The healthiest approach seems to be explicitly rejecting the pressure while remaining open to future opportunities. Jeff puts it well: "If I find something that really really bothers me or that I feel I can add an extreme amount of value, where people are begging me to do this, where it makes sense to run it as a business, then yeah I wouldn't be opposed to it." The key is waiting for genuine inspiration rather than manufactured urgency.
Designing a Life Worth Living
Successfully transitioning to early retirement requires more than just having enough money - it requires actively designing a life that provides meaning, connection, and growth. Both Ryan and Jeff have put significant effort into creating fulfilling post-work lives, treating the design of their daily experiences as seriously as they once treated building their businesses.
Ryan has embraced what he calls making his life "awesome" as his new job. This isn't about unlimited leisure or self-indulgence, but about intentionally creating experiences and memories that wouldn't have been possible during his work-focused years. "We went to Antarctica last year, looking at Kenya this year," he shares. "We hosted our whole family - there was like 30 or so people. We had people set up tables and brought in food and like had all these activities, rented out a pickleball court, took everybody for surf lessons."
These aren't just expensive vacations - they're investments in relationships and shared experiences that create lasting value. Ryan has also started a blog called "After the Exit" where he shares his experiences and connects with others going through similar transitions. This provides both creative outlet and community connection while helping others navigate their own post-exit journeys.
Jeff has found fulfillment through passion projects that, while successful, aren't primarily motivated by financial returns. When contacted for this interview, he was at an amusement park taco truck at 11 AM on a Tuesday - exactly the kind of spontaneous freedom that early retirement should enable. His passion projects have been successful enough to provide additional income and, more importantly, a sense of purpose and achievement outside the traditional business framework.
The key insight from both experiences is that successful early retirement requires replacing the structure, community, and sense of progress that work provided. This doesn't happen automatically - it requires the same intentionality and effort that building a business requires, just directed toward different goals.
The Psychology of Living Off Investments
One of the most surprising challenges both Ryan and Jeff faced was the psychological burden of managing large investment portfolios. When your entire lifestyle depends on investment returns rather than earned income, even rational portfolio management becomes emotionally fraught.
Ryan describes feeling like the money was "a burden for a little bit" after his exit. "It was like oh my gosh, I can't lose this." This anxiety is common among people who suddenly have large sums to protect rather than continuing to generate new income. The fear of losing what you've worked so hard to build can become paralyzing.
The solution for Ryan involved working with financial advisors, despite acknowledging that "the internet really shits on financial advisers." He found value not in complex investment strategies, but in having professionals help him think rationally about portfolio allocation and withdrawal rates. His current strategy is deliberately boring: 60% equities (simple ETFs) and 40% fixed income, generating roughly 3% annual income after taxes.
This conservative approach reflects a crucial insight about early retirement: once you have enough, preservation becomes more important than growth. Ryan's $20 million generates about $50,000 monthly in investment income, while his spending is $25-30,000 monthly. This gives him a significant cushion and peace of mind that aggressive growth strategies couldn't provide.
Jeff learned a similar lesson through painful experience. During periods when his net worth was highest, he was also most anxious because he was constantly checking portfolio performance. "You're just refreshing and you're checking and you're looking at the stock." The psychological toll of daily wealth fluctuations often outweighed any financial benefits of more complex strategies.
Both discovered that simplicity reduces anxiety. Jack, another early retiree mentioned in the episode, invested in "much too much different stuff" which caused "extreme amounts of anxiety to administer" including tax complications and address changes. His advice in hindsight: "Keep it much more concentrated, probably most of my money in an ETF like a Vanguard ETF."
The Spending Down Dilemma
Perhaps the most philosophically challenging aspect of early retirement is deciding how much money to actually enjoy versus preserve for the future. Many early retirees find themselves trapped in a mindset where they continue accumulating wealth they'll never realistically spend, missing opportunities to enjoy their money while they're young and healthy.
Jeff has been wrestling with this question directly: "I've actually been thinking about trying to spend down my money and not being afraid to say hey, what would my life be like if I wanted to spend a million dollars this year and not be afraid to... There's something sad about that a little bit that I'm going to save all this money for when I'm like 70 years old and that's when I'm going to start to enjoy it versus now I'm like man I can do anything, my body works great, I have awesome friends."
This touches on a fundamental tension in financial planning. Traditional advice focuses on preservation and compound growth, but if you've already achieved financial independence in your 30s, optimizing for maximum wealth at death might mean missing the best years to actually enjoy that wealth.
Jeff's approach is to maintain a $10 million "backstop" while being more willing to spend the excess. This provides psychological security while enabling meaningful experiences during his peak physical and social years. He's not talking about reckless spending - when flying to New York, he still chooses coach - but rather being willing to invest in experiences and relationships that money can uniquely enable.
The math supports this approach for people with substantial wealth. If you have $20 million and spend $1 million per year, you'd need to live 20 more years to exhaust your principal, ignoring any investment returns. For someone in their 30s or 40s, this provides enormous flexibility to front-load experiences and enjoyment rather than optimizing for maximum estate value.
This philosophy requires overcoming deeply ingrained habits of accumulation and delayed gratification that were necessary during the wealth-building phase. But as Jeff points out, the whole purpose of building wealth was to enable freedom and choice - if you never exercise that freedom, the accumulation becomes an end in itself rather than a means to a better life.
The Question of Returning to Work
Neither Ryan nor Jeff views retirement as necessarily permanent, which provides psychological flexibility and reduces the pressure to "get retirement right" on the first try. This approach treats early retirement as one phase of life rather than a final destination, removing some of the weight from the decision to step away.
Ryan is considering eventually returning to entrepreneurship, though with different parameters: "I couldn't imagine really managing a team right now, I'm still a little toasty from it, but maybe I may do it a little differently." He's thinking about smaller, cash-flowing businesses rather than high-growth ventures requiring intensive management and team building.
Jeff is even more selective about potential returns: "If I find something that really really bothers me or that I feel that I can add an extreme amount of value, where people are begging me to do this, where it makes sense to run it as a business, then yeah I wouldn't be opposed to it." This sets a high bar - not just "I'm good at this" but "this problem needs solving and I'm uniquely positioned to solve it."
This flexibility is psychologically valuable because it removes the permanence that makes retirement decisions feel so weighty. If you know you can always go back to work, the stakes of trying retirement feel lower. You're not making an irreversible life choice, just experimenting with a different way of living.
The approach also acknowledges that interests, energy levels, and life circumstances change over time. Jeff explicitly recognizes that his current lifestyle depends partly on being single: "The freedom and flexibility that I have and that I value so highly right now, it is largely indicative of the fact that I know that that will go away once I have a family and a relationship."
This perspective treats early retirement as an opportunity to experience a type of freedom that may not be available later in life, rather than as an escape from work forever. It's about timing different life experiences optimally rather than making absolute commitments about never working again.
"My self-worth was based in how hard I worked on something... I didn't have that anymore and I was searching for that next grind or addiction to work on something. That's that loss period."
"There's something sad about saving all this money for when I'm like 70 years old and that's when I'm going to start to enjoy it versus now when my body works great and I have awesome friends."
"I wrote this post where it's like I feel like your job can be to make your life awesome. It doesn't need to be what you thought of what a job is - that is the job now."
Conclusion
The reality of early retirement after achieving significant wealth is far more complex than the simple narrative of "make money, stop working, enjoy life." Both Ryan and Jeff discovered that stepping away from successful careers triggers a profound identity crisis that can last months, along with the loss of professional communities and social structures that had provided meaning and connection.
The psychological burden of managing large investment portfolios, combined with external pressure to "do something next," creates new forms of stress that money alone doesn't solve. However, both have found that intentionally designing a fulfilling post-work life - treating the creation of experiences and relationships as seriously as they once treated building businesses - can lead to genuine satisfaction. Perhaps most importantly, their approach of viewing retirement as flexible rather than permanent removes much of the pressure from the decision to step away, allowing them to experiment with different ways of living without feeling trapped by irreversible choices.
The key insight is that early retirement isn't about escaping work forever, but about having the freedom to choose what work means to you and when to engage with it on your own terms.
Practical Implications
- Plan for 6-8 months of identity adjustment - Expect to feel lost or grieving after exiting, as your self-worth was likely tied to work output and professional achievement
- Design your post-work life intentionally - Treat creating fulfilling experiences and relationships as seriously as you once treated building businesses
- Keep investments simple and boring - 80% index funds, 20% bonds reduces anxiety more than complex strategies that require constant monitoring
- Use the 3% withdrawal rule as a starting point - This provides sustainable income while maintaining principal, giving psychological security about never running out
- Consider relocating to areas with schedule flexibility - Major metropolitan areas have more people with non-traditional schedules who can provide social connection
- Reject external pressure about "what's next" - Life isn't a scoreboard requiring immediate efficiency in reaching the next milestone
- Maintain a financial backstop but spend meaningfully - Keep enough for security (often $10M+) but don't optimize for maximum wealth at death if you're already financially independent
- View retirement as flexible, not permanent - This reduces pressure and allows experimentation with different life phases without feeling trapped by irreversible decisions
