Upticks: A Financial Planning & Investment Podcast

Hosted by Jake Falcon

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413

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Aug 2026

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About the show

Welcome to Upticks, your podcast for financial insights. Hosted by Jake Falcon, CRPC® and Cory Bittner, CRPC®, who discuss the philosophy of wealth management, exploring tailored retirement plans, tax strategies, and timely market topics. Join us for concise, understandable discussions that empower your financial literacy. Disclaimer: Securities offered through HighTower Securities, LLC. Member FINRA/SIPC, HighTower Advisors, LLC is a SEC registered investment Adviser

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August 19, 2026Episode 40937 min

Socialism, the Fed, and the Hidden Costs of Real Estate Investing

Can the economics of socialism be discussed without becoming partisan? Should the Federal Reserve hold interest rates steady? And does residential real estate offer the returns many investors assume? In this episode of Upticks, Jake and Cory discuss why affordability has made simple political promises more appealing, how monetary policy and consumer behavior interact, and why real estate returns should be evaluated after accounting for leverage, expenses, taxes, concentration, and limited liquidity. --------------- Get your complimentary guide to retirement https://falconwealthadvisors.com/retiring-right-e-book.html?utm_source=libsyn&utm_medium=podcast&utm_campaign=rr_ebook Get Jake's weekly blog https://falconwealthadvisors.com/notes-from-jake.html?utm_source=libsyn&utm_medium=podcast&utm_campaign=notes_from_jake Question for Jake and Cory? Email Luke → luke@falconwealthadvisors.com Watch clips of this episode on YouTube https://youtube.com/@uptickspodcast?si=H2Nj_aq7Jdh9AIc4 Follow Jake and Cory https://www.instagram.com/jake_falcon_crpc/?hl=en https://www.instagram.com/corybittnerkc/ #economics #interestrates #realestateinvesting #financialliteracy #uptickspodcast

August 13, 2026Episode 40827 min

401(k) Rollovers, Private Equity, and Roth Conversions

What should you do with a 401(k) after leaving an employer? Should private equity be included in workplace retirement plans? And when does a Roth conversion deserve consideration? In this episode of Upticks, Jake and Cory discuss three financial decisions that are often treated as automatic answers. They explain why each choice should instead be evaluated within the context of an individual financial plan, including investment strategy, access to retirement funds, taxes, liquidity, and long-term goals. --------------- Get your complimentary guide to retirement https://falconwealthadvisors.com/retiring-right-e-book.html?utm_source=libsyn&utm_medium=podcast&utm_campaign=rr_ebook Get Jake's weekly blog https://falconwealthadvisors.com/notes-from-jake.html?utm_source=libsyn&utm_medium=podcast&utm_campaign=notes_from_jake Question for Jake and Cory? Email Luke → luke@falconwealthadvisors.com Watch clips of this episode on YouTube https://youtube.com/@uptickspodcast?si=H2Nj_aq7Jdh9AIc4 Follow Jake and Cory https://www.instagram.com/jake_falcon_crpc/?hl=en https://www.instagram.com/corybittnerkc/ #401k #retirementplanning #rothconversion #privateequity #uptickspodcast

August 7, 2026Episode 40732 min

Leverage, Concentrated Stock, and Is Early Retirement Overrated?

What happens when leverage, confidence, and speculation collide? Jake and Cory begin this episode by discussing a highly leveraged hedge fund and the risks of investing with borrowed money. They also explain how options strategies may help executives manage concentrated company stock before turning to a deeper question: Is retiring as early as possible really the right goal? The conversation explores the difference between financial independence and leaving work, why purpose remains important in retirement, and why a complete retirement plan should address what you are retiring to—not only whether you can afford to stop working. --------------- Get your complimentary guide to retirement https://falconwealthadvisors.com/jake-falcon-book-signup.html?utm_source=podcast&utm_medium=content&utm_campaign=rr_ebook Get Jake's weekly blog https://falconwealthadvisors.com/index.html?utm_source=youtube&utm_medium=video&utm_campaign=upticks#ID2GUSO1Sj8Upy1QWdqVxHOM Question for Jake and Cory? Email Luke → luke@falconwealthadvisors.com Watch clips of this episode on YouTube https://youtube.com/@uptickspodcast?si=H2Nj_aq7Jdh9AIc4 Follow Jake and Cory https://www.instagram.com/jake_falcon_crpc/?hl=en https://www.instagram.com/corybittnerkc/ #retirementplanning #financialindependence #investing #stockoptions #uptickspodcast

July 30, 2026Episode 40617 min

20 Years of Retirement Planning Taught Me These 5 Things

What separates a successful retirement plan from one that's simply invested? In this solo episode of Upticks, Jake shares five practical lessons he's learned from more than 20 years of helping clients prepare for retirement. He explains why financial organization, tax planning, flexibility, and aligning your investments with your personal goals often matter more than chasing market performance. Whether you're approaching retirement or simply looking to improve your financial plan, this episode offers practical ideas you can apply today. --------------- Get your complimentary guide to retirement https://falconwealthadvisors.com/jake-falcon-book-signup.html?utm_source=podcast&utm_medium=content&utm_campaign=rr_ebook Get Jake's weekly blog https://falconwealthadvisors.com/index.html?utm_source=youtube&utm_medium=video&utm_campaign=upticks#ID2GUSO1Sj8Upy1QWdqVxHOM Question for Jake and Cory? Email Luke → luke@falconwealthadvisors.com Watch clips of this episode on YouTube https://youtube.com/@uptickspodcast?si=H2Nj_aq7Jdh9AIc4 Follow Jake https://www.instagram.com/jake_falcon_crpc/?hl=en #retirementplanning #financialplanning #retirement #investing #uptickspodcast

July 24, 2026Episode 40539 min

When Money Stops Changing Your Life

In this episode, Jake and Cory begin by revisiting the growing conversation around private investments inside 401(k) plans and why they remain skeptical of the trend. They also discuss the rise of index investing and understanding what you own. They debate whether high earners should own vacation homes, when renting may make more sense than buying, and ways lifestyle decisions can have a bigger impact than financial projections alone. Finally, at what point does money stop changing your life? Drawing from years of client experience, they discuss the differences between financial security, purpose, cash flow, and happiness. --------------- Get your complimentary guide to retirement https://falconwealthadvisors.com/jake-falcon-book-signup.html?utm_source=podcast&utm_medium=content&utm_campaign=rr_ebook Get Jake's weekly blog https://falconwealthadvisors.com/index.html?utm_source=youtube&utm_medium=video&utm_campaign=upticks#ID2GUSO1Sj8Upy1QWdqVxHOM Question for Jake and Cory? Email Luke → luke@falconwealthadvisors.com Watch clips of this episode on YouTube https://youtube.com/@uptickspodcast?si=H2Nj_aq7Jdh9AIc4 Follow Jake and Cory https://www.instagram.com/jake_falcon_crpc/?hl=en https://www.instagram.com/corybittnerkc/ #retirementplanning #networth #401k #financialindependence #wealthmanagement

July 17, 2026Episode 40431 min

What Can Really Put Retirement at Risk?

In this episode, Jake and Cory react to a listener-submitted article about proposed 401(k) changes that could make private equity and other alternative investments more accessible. They explain why they believe retirement plans should stay simple and discuss the risks of adding complexity to long-term investing. The conversation then turns to retirement planning, including a debate on the biggest risks retirees face, the challenge of "golden handcuffs," and why decisions about retirement can often involve more than just money. They wrap up with a discussion on mega backdoor Roth contributions and when they may—or may not—make sense. --------------- Get your complimentary guide to retirement https://falconwealthadvisors.com/jake-falcon-book-signup.html?utm_source=podcast&utm_medium=content&utm_campaign=rr_ebook Get Jake's weekly blog https://falconwealthadvisors.com/index.html?utm_source=youtube&utm_medium=video&utm_campaign=upticks#ID2GUSO1Sj8Upy1QWdqVxHOM Question for Jake and Cory? Email Luke → luke@falconwealthadvisors.com Watch clips of this episode on YouTube https://youtube.com/@uptickspodcast?si=H2Nj_aq7Jdh9AIc4 Follow Jake and Cory https://www.instagram.com/jake_falcon_crpc/?hl=en https://www.instagram.com/corybittnerkc/ #retirementplanning #goldenhandcuffs #401k #rothira #financialfreedom

July 10, 2026Episode 40338 min

Smart People Can Make Terrible Investment Decisions

In this episode, Jake and Cory dig into reasons smart, successful people still make bad investment decisions. Pointing to recency bias, overconfidence, and financial media that markets fear and greed instead of sound strategy. They break down their belief of compound interest (not stock picking) being a better path to retirement, and ways "save first, spend second" can solve more money problems than people realize. The conversation wraps with a candid look at money in relationships. Reasons joint vs. separate accounts matter less than actually talking about finances, and ways couples can get aligned instead of avoiding the conversation altogether. --------------- Get your complimentary guide to retirement https://falconwealthadvisors.com/jake-falcon-book-signup.html?utm_source=podcast&utm_medium=content&utm_campaign=rr_ebook Get Jake's weekly blog https://falconwealthadvisors.com/index.html?utm_source=youtube&utm_medium=video&utm_campaign=upticks#ID2GUSO1Sj8Upy1QWdqVxHOM Question for Jake and Cory? Email Luke → luke@falconwealthadvisors.com Watch clips of this episode on YouTube https://youtube.com/@uptickspodcast?si=H2Nj_aq7Jdh9AIc4 Follow Jake and Cory https://www.instagram.com/jake_falcon_crpc/?hl=en https://www.instagram.com/corybittnerkc/ #investingwisely #wealthbuilding #financialfreedom #retiresooner #smartmoneymoves

July 2, 2026Episode 40234 min

Reasons People Can Go Broke Trying to Look Rich

What does financial freedom really look like? Are we chasing wealth or just the appearance of it? In this episode, Jake and Cory dive into the psychology behind money decisions, from homeownership and lifestyle inflation to raising financially independent children and resisting the urge to keep up with the Joneses. The conversation also tackles a question many parents wrestle with: when does helping your children become enabling them? Jake and Cory share perspectives on teaching financial responsibility, setting healthy boundaries, and preparing the next generation for independence. Plus, they examine why some multimillionaires still feel broke, how consumer culture influences spending habits, and reasons your most valuable asset may not be your money but your time. --------------- 📘 Get Jake's bestselling book — Retiring Right https://falconwealthadvisors.com/jake-falcon-book-signup.html?utm_source=podcast&utm_medium=content&utm_campaign=rr_ebook 📩 Have a question for Jake and Cory? Email Luke directly → luke@falconwealthadvisors.com --------------- Upticks is your podcast for financial planning insights. Hosted by Jake Falcon, CRPC™ and Cory Bittner, CRPC™, who discuss the philosophy of wealth management, exploring tailored retirement plans, tax planning, and timely industry topics. Join us for concise, understandable discussions that help empower your financial literacy. --------------- Connect with Jake Falcon, CRPC™ https://www.facebook.com/jake.falcon.524 https://www.instagram.com/jake_falcon_crpc/?hl=en https://twitter.com/jakefalconcrpc https://www.linkedin.com/in/jakefalconfalconwealthadvisors #financialplanning #retirementplanning #personalfinance #wealthbuilding #financialfreedom #moneymindset #investing #financialeducation #moneymanagement #uptickspodcast

June 26, 2026Episode 40142 min

Does Spending Drop in Retirement? Here's What We Found

Are Roth conversions a smart tax strategy or one of the most overhyped ideas in retirement planning? Should retirees stay invested aggressively? Do most people really need an annuity? And when is the right time to claim Social Security? In this episode of Upticks, Jake and Cory tackle some of the biggest debates in retirement and financial planning. Drawing from decades of combined experience working with retirees, they break down popular financial strategies and explain reasons the right answer often depends on your personal goals, cash flow needs, and long-term plan. The discussion covers the pros and cons of Roth conversions, the myth that age should determine your investment allocation, reasons annuities remain controversial, and key factors to consider when deciding when to start Social Security benefits. Jake and Cory also explore a topic that affects nearly every retiree: spending habits. They discuss why retirement spending doesn't always decrease as expected Whether you're preparing for retirement, already retired, or simply looking to make more intentional financial decisions, this episode offers practical insights designed to help you think differently about your money. --------------- 📘 Get Jake's bestselling book — Retiring Right https://falconwealthadvisors.com/jake-falcon-book-signup.html?utm_source=podcast&utm_medium=content&utm_campaign=rr_ebook 📩 Have a question for Jake and Cory? Email Luke directly → luke@falconwealthadvisors.com --------------- Upticks is your podcast for financial planning insights. Hosted by Jake Falcon, CRPC™ and Cory Bittner, CRPC™, who discuss the philosophy of wealth management, exploring tailored retirement plans, tax planning, and timely industry topics. Join us for concise, understandable discussions that help empower your financial literacy. --------------- Connect with Jake Falcon, CRPC™ https://www.facebook.com/jake.falcon.524 https://www.instagram.com/jake_falcon_crpc/?hl=en https://twitter.com/jakefalconcrpc https://www.linkedin.com/in/jakefalconfalconwealthadvisors #retirementplanning #financialplanning #rothconversions #socialsecurity #investmentstrategy #wealthmanagement #taxplanning #retirementincome #personalfinance #falconwealthadvisors

June 18, 2026Episode 40037 min

SpaceX, OpenAI, Anthropic: Will They Crash the Market?

In this milestone 400th episode of Upticks, Jake and Cory celebrate how far the show has come and dive straight into what matters most: answering listener-driven questions shaping today's financial landscape. This episode is packed with sharp insights on one of the biggest themes in investing right now: the surge of AI-related IPOs. With companies like SpaceX, OpenAI, and Anthropic dominating headlines, Jake and Cory go beyond the hype to help investors explore whether these record-breaking debuts could actually move the market or simply fuel speculation. They tackle the growing "democratization" of IPO investing, questioning whether easier access is empowering investors or exposing them to unnecessary risk. From market concentration and index inclusion to the realities of profitability versus excitement, this discussion is grounded in experience-based perspective. --------------- 📘 Get Jake's bestselling book — Retiring Right https://falconwealthadvisors.com/jake-falcon-book-signup.html?utm_source=podcast&utm_medium=content&utm_campaign=rr_ebook 📩 Have a question for Jake and Cory? Email Luke directly → luke@falconwealthadvisors.com