Retirement doesn’t follow a script – it rewrites itself in real time. In this episode, Jason and Eric unpack why the classic “phases” of retirement actually overlap and how that feels day to day. They dig into the challenges of switching from super-saver to intentional spender, using side income (like options trading or creative work) to fund experiences without derailing the plan, and how travel has changed for them. No matter where you are on the FIRE path, there’s something here for you.
How does it feel when you haven’t yet found your purpose after retiring early? In this episode, Retired Early and Feeling Lost. What’s Next?, Jason talks with Eric about the first three years years exploring his post-FIRE purpose. They discuss the phases of retirement, seeking out meaningful projects, lessons learned along the way, and much more.
Drawdown is a favorite topic of ours and one we’ve come back to time and time again. For practical help with modeling your own safe withdrawal rate plan, don’t miss our very popular multi-part tutorial series on the SWR Toolbox. You can find them all here.
How can a hobby turn into a second career and lead to financial independence before 40? In this episode, Jason talks with David Sun, an electrical engineer who stumbled into options trading after hearing about it from a fellow grad student. Only ten years later he launched his first hedge fund.
The topic of cash positions and how we manage them has been a regularly occurring topic on 2SFI. Get all the details here, including episodes devoted to the topic.
In this episode, Jason mentions his “IPS” or Investment Policy Statement. Chasing short term market conditions adds a lot of risk to reaching your long term investing goals. In “Is This a Part of Your FIRE Plan?”, we talk about how an IPS can help ensure you stick to your strategy, and avoid market timing and other investing pitfalls.
Why has ProjectionLab quickly become one of the most popular early retirement planning tools? In this episode, learn why PL is an essential software package for both Eric and Jason. Topics covered include how to get started, best practices, and powerful new features.
Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.
Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.
Do you want to avoid the biggest retirement risk? This simple to use tool will let you model your safe withdrawal rate and help ensure you don’t run out of money. In this walkthrough video, we teach you how to use this powerful, flexible, and FREE tool created by Karsten Jeske. Using the SWR Toolbox, you can ensure that you have a personalized plan that works with your own financial situation.
Part 2: Eric + Jason discuss how they’re using the SWR Toolbox and how Jason is struggling to spendas much as he can safely doin early retirement
How much money can you safely spend in retirement? In part two of this series on safe withdrawal rates, we discuss the #1 tool we’ve found to help you answer that question. Topics covered include the SWR Toolbox, our thoughts on Social Security, the challenges of spending in retirement, and how to get comfortable with increasing your withdrawal rate.
Part 3: Walkthrough of the CAPE-Based Rule tab in the SWR Toolbox
Do you like the idea of a portfolio withdrawal strategy that can’t run out of money? This walkthrough video is the third part in our Safe Withdrawal Rate (SWR) series, and teaches you how to model a variable withdrawal strategy based on the CAPE ratio. Using this powerful and FREE tool created by Karsten Jeske, you can design a personalized plan that works with your own financial situation.
Part 4: How Jason builds his retirement paycheck using the SWR Toolbox
How do you plan to set up your retirement paycheck to avoid running out of money? In this episode, Jason talks with Eric about how he uses a free online tool to manage his finances in early retirement. Topics covered include his variable withdrawal strategy, managing cash, portfolio rebalancing, and much more.
Part 5: Answering your questions about using CAPE-adjusted strategies
In Part 5 of our SWR Toolbox series, we answer your questions about our CAPE-based withdrawal strategy, how it compares to a fixed safe withdrawal rate approach, and much more. See the link below for all of our toolbox videos including tutorials and a host of supportive content in the show notes.
Show Notes
Download the Safe Withdrawal Rate (SWR) Toolbox
The Safe Withdrawal Rate Toolbox is available via Karsten Jeske’s Early Retirement Now blog. The current version can be downloaded via Part 28 of the SWR series. This is also the post where the revisions to the calculator are described. To see the history of this tool, you’ll need to go back to Part 7. We found reading both posts to be essential to really understand how the tool works. Please ensure you follow the directions in the video to make your own copy of the tool. There’s no need to email Karsten to request edit rights!
Essential Blog Posts
Safe Withdrawal Rate series: This is the landing page for the 61-partSWR series (it will surely continue to grow) for which Karsten is best known. Be sure to start with the guidance he provides on how to navigate this great but expansive content. Many essential topics are covered in the series and not all of them involve deep dives into math! While we think all of his posts are interesting, you’ll find guidance below about the specific articles we think are most important to the topic of this video – in addition to Parts 28 and 7 listed above.
Sequence Risk is more important than your average return rate. Surprised? Be sure to check out Part 15: More Thoughts on Sequence of Return Risk. As mentioned in the video, SWR is overwhelmingly determined by the first 10-15 years of portfolio drawdown.
Are you the kind of person who wants all the gory details about the math underlying the SWR Toolbox? If so, you won’t want to miss Part 8: Technical Appendix. It’s got all the information you need to fully understand how Karsten’s approach works. There are also some good references at the bottom of the post on related material found elsewhere.
Did you know we’ve spoken to Karsten twice before?“What the FIRE Community Gets Wrong” was the first time he came on Two Sides of FI. We covered a lot of ground in this episode about safe withdrawal strategies – so much so that we also released a follow-up video called “Karsten Spoke, We Listened. Here’s What We Learned”. These two episodes are popular with our audience for a good reason and are definitely worth viewing for anyone interested in SWR strategies.
Our second conversation with Karsten also featured Fritz Gilbert (from The Retirement Manifesto), in a continuation of their debate about the merits of bucket strategies. In “What’s Wrong with This Popular Retirement Strategy?” we covered a lot of ground that you won’t want to miss!
Other Show Notes
We get a lot of questions about portfolio rebalancing. Would you like a free tool to help you rebalance your portfolio using the same approach we do? This calculator provides a convenient mechanism to enter and track your asset allocation, flag when any assets exceed your allocation targets, and model any rebalancing that may be needed. It’s really easy to use as you’ll see in our introductory video.
In Part 4, Jason mentions his “IPS” or Investment Policy Statement. Chasing short term market conditions adds a lot of risk to reaching your long term investing goals. In “Is This a Part of Your FIRE Plan?”, we talk about how an IPS can help ensure you stick to your strategy, and avoid market timing and other investing pitfalls. Topics covered include defining portfolio makeup + objectives, the mechanics of cash generation + rebalancing, and why you might consider implementing an IPS yourself
cFIREsim (or Crowdsourced Financial Independence and Retire Early Simulator) is a very popular and powerful FIRE calculator created by Lauren. We found a lot of value in this tool throughout our FIRE journey, and clearly many others do as well. In the developer’s words, “What can cFIREsim do? At its core, you can enter information in the a few simple inputs and return the basic simulation. At its most complicated, it can determine your portfolio success based on 80 individual portfolio adjustments, multiple types of inflation, multiple types of market returns, and graphically show you the results. There are many options to choose from outside of the ‘Basic Inputs’ “, including a number of variable withdrawal strategies under “Spending Plan”.
Variable Percentage Withdrawal (VPW) is another method besides CAPE-adjusted WR for allowing market conditions to influence the amount you take out of your portfolio in drawdown. As mentioned in parts 2 and 4, VPW is popular among some adherents the Bogleheads approach to investing. As you’ll read at this link, this method “adapts adjustments to portfolio withdrawal amounts to the retiree’s retirement horizon, asset allocation, and portfolio returns during retirement… to allow the retiree to spend most of the portfolio using return-adjusted withdrawals. By adapting withdrawals to market returns, VPW will never prematurely deplete the portfolio.”
stickK is the app Eric mentioned in Part 2 to help track adherence to a goal – like keeping to spending your planned withdrawal rate. Created from a behavioral economics framework, stickK allows you to create “Commitment Contracts, [which are] a binding agreement you sign with yourself to ensure that you follow through with your intentions—and it does this by utilizing the psychological power of loss aversion and accountability to drive behavior change.” We’ve not tried this yet but this is a pretty appealing (an a little scary) idea!
You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.
Are FIRE content creators being honest about their numbers? YouTuber Duane isn’t so sure. In this episode, Eric and Jason share detailed insights about their own FIRE numbers, portfolios, withdrawal rates, and what it actually means to be “retired.” They also explain why context matters more than a single number, and get honest about how content creation fits into their financial picture. If you’ve ever wondered how real people make FIRE work, this one’s for you.
While this episode contains the best summary of all of our FIRE numbers, it’s certainly not the first time we’ve tackled “THE number”, on which so many in the community focus. In “So, What’s Your Financial Independence (FI) Number?” we went through all the details of how to calculate your own FIRE number. But the number is only the beginning. In “Discussing our FI Numbers : Changing our minds, talking to family“, we discussed moving beyond the math of financial independence to discuss the psychological aspects, including important conversations with family and friends
Once again, the idea of safe withdrawal rates and Big ERN’s Safe Withdrawal Rate Toolbox came up in this conversation. For practical help with modeling your own safe withdrawal rate plan, don’t miss our very popular multi-part tutorial series on the SWR Toolbox. You can find them all here.
Certainly in the US, one of the most common fears about retirement is healthcare. Did you know we’ve tackled this topic at least three times before? Check out these show notes for links to all of them. There, you’ll find the episodes and a host of associated content on the topic.
Don’t think that our FIRE journeys were devoid of errors! We discussed just how far from mistake-free our journeys were in Don’t Make These Financial Mistakes on the Path to FIRE! (Part 1) and (Part 2).
The FI journey is far from a solo one for most people, particularly those with long term partners or spouses. Particularly for the kinds of weighty decisions that we discussed in this episode, it’s essential to be on the same page regarding one’s FI path.Many seem to agree that our two-part series where we discuss our FIRE paths with our spouses, Lorri and Laura, is essential Two Sides of FI content. Check it out here: Part 1 and Part 2!
We’ve released a number of milestones-related episodes, charting our FIRE journeys, a number of which are among our most popular content. These are a great way to get caught up on our backgrounds. Here’s the list of all of them.
Empower (formerly Personal Capital) is a commonly used free tool for tracking your various investment accounts, understanding your asset allocation + rebalancing opportunities, and monitoring your net worth. PC has simple to use account linking to make it a more automated experience. Give it a try risk-free!
Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.
Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.
What’s the scariest part of retiring early? For many, it’s not just about money—it’s the unknowns that come after leaving work behind. In this candid conversation, Eric and Jason unpack the biggest fears they and others faced on the path to FIRE, from financial worries and healthcare to identity shifts and societal judgment. Whether you’re planning your own early retirement or already there, this episode will help you feel less alone and more prepared.
Once again, the idea of safe withdrawal rates and Big ERN’s Safe Withdrawal Rate Toolbox came up in this conversation. For practical help with modeling your own safe withdrawal rate plan, don’t miss our very popular multi-part tutorial series on the SWR Toolbox. You can find them all here.
How Do I Know When I’m Ready to Retire? This episode was referenced a few times, and for good reason. Most on the FIRE path focus on the financial elements because in essence, they’re the easiest part of the equation. But many people struggle with the emotional elements of the decision. For more on the retirement personas we highlighted via the slides shown in the current video, check out the episode!
Underspending is a very common stumbling block for those transitioning from saving to drawing down from their portfolio i.e. spending. In “How much money can you safely spend in retirement?“ we tackle this head-on.
Certainly in the US, one of the most common fears about retirement is healthcare. Did you know we’ve tackled this topic at least three times before? Check out these show notes for links to all of them. There, you’ll find the episodes and a host of associated content on the topic.
Many, if not most early retirees will eventually struggle with the question of working “just one more year”. We’ve tackled that essential topic a few times, most recently in Do I Wish I’d Worked One More Year? In this episode, we discuss the reasons you might consider that option, what Jason would have missed out on if he had worked longer, and the value he found in retiring when he did.
Empower (formerly Personal Capital) is a commonly used free tool for tracking your various investment accounts, understanding your asset allocation + rebalancing opportunities, and monitoring your net worth. PC has simple to use account linking to make it a more automated experience. Give it a try risk-free!
Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.
Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.
After five years of early retirement and 100 episodes of Two Sides of FI, what have we learned? A lot—and we’re sharing it all. To mark this milestone, Eric and Jason sit down for an honest, wide-ranging AMA based on questions from our community. We cover everything from money and mindset shifts to healthcare, travel, and even music choices. Whether you’re already on your FIRE path or just curious what life really looks like on the other side, this conversation is for you.
We’ve done a number of milestones-related episodes, charting our FIRE journeys, a number of which are among our most popular content. Here’s the list of all of them!
As expected we got a few questions on healthcare. Did you know we’ve tackled this topic at least three times before? Check out these show notes for links to all of them.
Rebalancing is natural counterpart to any conversation about asset allocation and it’s a key aspect to generating cash to fund your life post-RE. Are you interested in afree copy of the rebalancing tool that we use? That link will take you to it, as well as the episode in which it was discussed, Stock Market on FIRE: What We’re Doing in a Downturn.
Empower (formerly Personal Capital) is a commonly used free tool for tracking your various investment accounts, understanding your asset allocation + rebalancing opportunities, and monitoring your net worth. PC has simple to use account linking to make it a more automated experience. Give it a try risk-free!
Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.
Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.
With markets down at one point nearly 20% in 2025, is this the sequence risk moment we feared? In this episode, we reflect on recent market volatility, how it’s impacted our early retirement finances, and whether our original FIRE strategy can still hold up. We also catch up post-Liberation Day and share how our thinking has evolved after real-world stress testing our withdrawal plan. If you’re navigating FIRE in 2025—or just wondering what a 20% portfolio loss feels like—this one’s for you.
If you haven’t seen our most recent episode, What Should We Do With Bonds and Cash in a Crazy Market?, it’s a natural pairing with this video. In it, Eric talks with Jason about an unexpected opportunity to update his early retirement portfolio.
In the subsequent episode, My Plan to Retire Early is ON HOLD, Eric talked with Jason about pushing back his FI date, whether BaristaFIRE could be the answer, the possibility of redefining work, and advice for others in a similar position.
Once again, the idea of safe withdrawal rates and Big ERN’s Safe Withdrawal Rate Toolbox came up in this conversation. For practical help with modeling your own safe withdrawal rate plan, don’t miss our very popular multi-part tutorial series on the SWR Toolbox. You can find them all here.
Buying Stock in a Down Marketis a part of show guest, Fritz Gilbert’s, post-FIRE strategy, which he discussed in a recent conversation with us. In this episode highlight, we discuss how he felt during the 2020 market decline and learn about his approach to continue buying in order to take advantage of low equity prices.
Empower (formerly Personal Capital) is a commonly used free tool for tracking your various investment accounts, understanding your asset allocation + rebalancing opportunities, and monitoring your net worth. PC has simple to use account linking to make it a more automated experience. Give it a try risk-free!
Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.
Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.
How should you respond to market conditions to ensure financial stability? Like the famous Mike Tyson quote says, “Everyone has a plan until they get punched in the mouth”. In this episode, Eric talks with Jason about an unexpected opportunity to update his early retirement portfolio. Topics discussed include bond and cash allocations, asset location, and what they’re doing to manage extreme market volatility.
Relating to asset allocation, rebalancing, and several other topics we hit on in this episode, Jason and Eric talked about the former’s Investment Policy Statement (IPS) in Is This a Part of Your FIRE Plan?
Times like there are good opportunities for stress testing your plan and considering alternate scenarios. We both find ProjectionLab an essential and easy-to-use software package to support this important practice. You can get your own free trial here.
Unsurprisingly, the Safe Withdrawal Rate Toolbox came up in this conversation. For practical help with modeling your own safe withdrawal rate plan, don’t miss our very popular multi-part tutorial series on the SWR Toolbox. You can find them all here.
A Bond Tent strategy is one of the common approaches used by the FIRE community to mitigate both Retirement Date + Sequence of Returns Risks. As is often the case, Michael Kitces has a great article on the topic. We couldn’t cover sufficient depth on this important topic in our episode, but this post has all the details you need.
How To Build A Retirement Paycheck: This is the first of three great Retirement Manifesto posts on author Fritz Gilbert’s implementation of the Bucket Strategy, which we have touched on in several episodes to date. Here you’ll find guidance on how to determine the asset allocation you’ll want to have in place by the time you retire early. The other two articles in the series are linked here as well.
Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.
Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.
Do some find it hard to retire because they don’t know how to stop working? In today’s episode, Eric talks with Jason about the challenges he’s experienced after achieving FI, finding it hard to ramp down his business. Are we just wired to work hard or is there more to it? We discuss why Eric can’t stop working, how it affects his spouse, and what Jason has learned in his five years of RE.
Show Notes
Essential Background:
How Do I Know When I’m Ready to Retire? Most on the FIRE path focus on the financial elements because in essence, they’re the easiest part of the equation. But many people struggle with the emotional elements of the decision. We tackle it head-on here.
Retirement Is Nothing Like I Thought It Would Be – We all daydream about what retirement will be like, but will reality live up to expectations? In this episode, Eric and Jason were joined by Fritz Gilbert, who blogs at The Retirement Manifesto. Our discussion went well beyond the numbers, covering topics including finding your purpose, working “one more year”, determining your FIRE timing, and the keys to success in retirement.
One of the ways many early retirees stay busy is to take on some time of part-time “fun job”. But have you truly retired if you continue to do any work for money? In Financially Independent, Recreationally Employed (FIRE), Eric and Jason talk about their respective journeys, why the latter has a part-time job after retiring, the internet retirement police, and much more.
How would you feel if you worked hard to retire early and later realized you hated being retired? In Does Retirement = Happiness?, we address the reality that some people who achieve FIRE are disappointed, bored, or otherwise unhappy in retirement.
Did you see our recent episodes regarding Eric’s spouse, Laura’s, decision to retire from her career as a scientist? If not, you’ll definitely want to view:
The story begins with One Step Closer to FI/RE – Giving Notice. In this episode, Eric and Laura discuss their preparations as they near their FI number and Laura prepares to notify her employer that she’s leaving. Recorded in the fall of 2023, this behind-the-scenes discussion was prepared for publication the week Laura submitted her resignation notice.
Next we published Unexpected Reactions to My Early Retirement, Contempt, concern, surprise, envy, admiration, and support; just a few of the reactions Laura received when she announced she was retiring early, closing her biomedical research laboratory, and beginning a new phase of life beyond work. Some reactions were expected and some surprised her. In this episode, Eric and Laura unpack these interactions and chart their next steps as they prepare to leave work and step into early retirement.
What’s it really like to be 5 days away from early retirement? The last chapter (so far) in this story is Retiring (Early) in 5 Days. Am I Ready? Whether you’re questioning if early retirement is worth leaving a dream job, wrestling with your professional identity, or wondering how it feels when that last paycheck stops, Laura’s story offers inspiration and real-time insights about one of life’s biggest transitions.
Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.
Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.
What are the critical financial elements to track and review each year pre- and post-FI? In this episode, Eric and Jason share their processes and learnings from their 2024 annual review. Topics covered include tracking net worth and withdrawal rate, portfolio management, taxes, and much more.
For more details of how we complete our annual reviews, check out Our Net Worth Is Up! Sharing Our Financial Review Process. In this episode, Eric and Jason share their simple pre- and post-FI review processes for net worth tracking, portfolio review, setting savings and budget goals, and more.
Jason mentioned staying below his safe withdrawal rate ceiling in this episode. For all the details (and more), you’ll want to see our page dedicated to the Safe Withdrawal Rate Toolbox.If you’re familiar with Karsten Jeske, you’ll definitely want to check this out. It has all the information you need including all the videos in our series, including walkthroughs of the tool and the CAPE-based strategy that Jason referenced here.
In this video, we talked about how much we’re enjoying using Projection Lab for financial modeling including What-If scenarios. Stay tuned for an upcoming episode with lots more details! In the meantime, you can try out Projection Lab for yourself, free.
Jason mentioned that he still uses the software called YNAB to budget. What is YNAB? You Need a Budget is a popular budgeting tool for many in the FIRE community. If manual spreadsheets aren’t your thing or you’ve struggled with budgeting in the past, this may be a good solution. YNAB has a generous, free 34-day trialso you can see how well it works to help you understand and control spending.
Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.
Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, which started even before Two Sides of FI began. Get more information on those archived posts here.
How can a hobby turn into a second career and lead to financial independence before 40? In this episode, Jason talks with David Sun, an electrical engineer who stumbled into options trading after hearing about it from a fellow grad student. Only ten years later he launched his first hedge fund. Now in his mid-30s, David shares the keys to his success, as well as his thoughts on the role of options trading in a FIRE portfolio. Be sure to check out the show notes linked below for all the key resources shared in this conversation.
Show Notes
Are you completely new to options trading? The seemingly endless vocabulary can be a big barrier to entry for newcomers. Don’t miss our options glossary which you can find on the show notes page for Jason’s chat with Karsten. There’s a ton of useful information linked on that page so be sure to check it out.
A reminder that neither we at Two Sides or FI, nor David Sun, are providing individual investment advice. Each of us has our own circumstances, risk tolerance, and risk capacity. Options trading, while potentially lucrative, is also potentially risky given the regular use of leverage, and is therefore best suited for experienced investors. We strongly recommend the use of simulated or “paper trading” accounts (you can create one free at Interactive Brokers and Charles Schwab, among others) to learn and test strategies. You may also benefit from consultation with financial professionals.
Among our most popular episodes to date were our chat with Karsten about his Safe Withdrawal Toolbox, and our own four-part series on how we use this essential retirement planning tool. You can find all of these and much more at our SWR landing page, including a link to Big ERN’s options posts.
David has also spoken with Karsten. Jason enjoyed this Trade Busters episode, titled “From FIRE to PCR w/Karsten Jeske aka Big ERN”. It’s an important element of understanding how Karsten’s own options trading strategy has evolved over time.
David Sun’s Trade Busters landing page is a great starting point to dive into all the valuable content he has produced. To contact him or request access to his Discord, you’ll want to head here. The Trade Busters podcast is also an excellent resource. Be sure to check out Episode 48, “Where do I Start?”. You can also follow David on Twitter.
In our conversation, David mentioned several good resources for getting started with an education in options trading. The Options Alpha courses, and Options Playbook are one he found particularly useful in his own path to success.
Have you checked out the Two Sides of FI Discord server? If you’re not familiar, this is an instant messaging social network. Ours is meant to be a community for viewers of our show, as well as a space to discuss all things relation to FIRE. It’s totally open, free of charge, and is anonymous as you’d like. This makes it a safe space to talk about financial topics you might otherwise be sensitive about sharing. Come check it out and see if it fits your interests! There are both desktop and mobile apps available.
Did you know Jason resumed blogging? To be notified of his future posts, please consider subscribing here. He’s also archived his old blog, which documents the first two years after he retired from his career, and started even before Two Sides of FI began. Get more information on those archived posts here.
You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.
