Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money cover art

Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money

Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money

By: Matt Smith
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About this listen

 Sidebar with a CFP®” is your space for candid conversations about life inside BigLaw—the real stuff they don’t teach in law school or show in recruiter brochures. Hosted by Matt Smith, CFP® and founder of Concert Financial Planning, this show pulls back the curtain on what it actually feels like to climb the ranks, navigate transitions, and make big decisions in a high-stakes career. You’ll hear from Partners, Associates, and experts across law and finance—each sharing stories, surprises, and strategies for building a life (and career) that works for you.Matt Smith Economics
Episodes
  • Tax Planning for Big Law Attorneys During Tax Season with Brian Leben

    Tax Planning for Big Law Attorneys During Tax Season with Brian Leben
    Apr 2 2026

    Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money with Matt Smith, Episode 7

    In this episode of the Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money, Matt Smith speaks with tax advisor Brian Leben, partner of Lulloff, Leben & Taylor, LLC, a tax advisory firm.

    Tune in to the episode to hear about:

    * Tax planning considerations for big law attorneys during tax season

    * Avoiding steep underpayment penalties

    * Common gaps among high earners, including not maximizing pre-tax 401(k) and HSA contributions

    * Backdoor and “mega” backdoor Roth strategies, allowing after-tax contributions and in-service rollovers

    * A caution to popular social-media tax strategies (heavy vehicle deductions, conservation easements, intangible drilling costs, and the Augusta rule) are often inapplicable, complex, or not worth the hassle

    * Practical opportunities including properly applying composite/PTE state tax payments


    Learn more about Brian Leben:

    * Connect with Brian on LinkedIn: https://www.linkedin.com/in/brian-leben-mba-cpa-pmp-pfs-cfp-r-7b29045

    * Visit Lulloff, Leben & Taylor, LLC’s website: https://www.lltcpas.com

    * Email Brian: bleben@lltcpas.com


    ***********************************

    About “Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money”:

    You bill in 6-minute increments. Let’s get you some of that time back. “Sidebar with a CFP®” is your space for candid conversations about life inside BigLaw—the real stuff they don’t teach in law school or show in recruiter brochures.


    Hosted by Matt Smith, CFP® and founder of Concert Financial Planning, this show pulls back the curtain on what it actually feels like to climb the ranks, navigate transitions, and make big decisions in a high-stakes career.

    You’ll hear from Partners, Associates, and experts across law and finance—each sharing stories, surprises, and strategies for building a life (and career) that works for you.

    This isn’t a money podcast. It’s a life-in-BigLaw podcast—with a CFP® in the host chair.


    Watch or listen to more episodes of Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money:

    * YouTube: https://www.youtube.com/@concertfinplan

    * Apple: https://podcasts.apple.com/us/podcast/sidebar-with-a-cfp-pierce-the-veil-on-biglaw/id1847658694

    * Amazon: https://music.amazon.com/podcasts/f6d90e4a-7817-4390-b944-091fac616a7c

    * Spotify: https://open.spotify.com/show/2au3zmrNf0hb3BNgZid8aX

    * iHeart Radio: https://www.iheart.com/podcast/269-sidebar-with-a-cfpr-pierce-298226554


    Connect and learn more from your host, Matt Smith and Concert Financial Planning:

    * Connect with Matt on LinkedIn: https://www.linkedin.com/in/matthewcharlessmith

    * Follow Concert Financial Planning on LinkedIn: https://www.linkedin.com/company/concertfinplan

    * Follow Concert Financial Planning on Facebook: https://www.facebook.com/ConcertFinPlan

    * Follow Concert Financial Planning on Instagram: https://www.instagram.com/concertfinplan
    Show More Show Less
    42 mins
  • Building Wealth Through Real Estate Investment with Luke Sanders

    Building Wealth Through Real Estate Investment with Luke Sanders
    Mar 5 2026
    Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money with Matt Smith, Episode 6In this episode of the Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money, Matt Smith, speaks with Luke Sanders, owner of River City Screen Printing and Embroidery in San Marcos, Texas, which was founded by his parents in 1978 and grown to 85+ employees across multiple buildings.Tune in to the episode to hear about: * How Luke first built wealth through acquiring and expanding commercial real estate for his operating business, including buying adjacent buildings and leasing one to a pawn shop tenant * Entering short-term rentals in 2019, including a large river house in New Braunfels/Green and multiple Fredericksburg properties * How COVID initially created cancellation risk but later produced a major demand surge (e.g., $80,000 revenue in one month) followed by market oversaturation * Regulatory and licensing uncertainty (city council efforts to restrict or sunset short-term rental permits) * Commercial loan structures with five-year rate resets that can turn cash flow negative * Reliance on local market knowledge and specialized realtors * Frequent maintenance/replacement costs from guest wear-and-tear * Using property management companies (typically 20–30% of revenue) to avoid 24/7 operational issues * Rising insurance costs (e.g., from $3,000 to $15,000 annually) * FEMA floodway rezoning that can eliminate short-term rental use * Why short-term rentals are risky for anyone depending on slim monthly margins * Why Luke’s best, least stressful results have been in commercial buildings with stable tenantsLearn more about Luke Sanders: * Connect with Luke Sanders on LinkedIn: https://www.linkedin.com/in/luke-sanders-b2b4711a * Visit RiverCity Screenprinting & Embroidery’s website: https://welogoit.com * Follow RiverCity Screenprinting & Embroidery on Facebook: https://www.facebook.com/RivercityScreenprinting * Follow RiverCity Screenprinting & Embroidery on Instagram: https://www.instagram.com/rivercityscreenprinting***********************************About “Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money”:You bill in 6-minute increments. Let’s get you some of that time back. “Sidebar with a CFP®” is your space for candid conversations about life inside BigLaw—the real stuff they don’t teach in law school or show in recruiter brochures.Hosted by Matt Smith, CFP® and founder of Concert Financial Planning, this show pulls back the curtain on what it actually feels like to climb the ranks, navigate transitions, and make big decisions in a high-stakes career.You’ll hear from Partners, Associates, and experts across law and finance—each sharing stories, surprises, and strategies for building a life (and career) that works for you.This isn’t a money podcast. It’s a life-in-BigLaw podcast—with a CFP® in the host chair.Watch or listen to more episodes of Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money: * YouTube: https://www.youtube.com/@concertfinplan * Apple: https://podcasts.apple.com/us/podcast/sidebar-with-a-cfp-pierce-the-veil-on-biglaw/id1847658694 * Amazon: https://music.amazon.com/podcasts/f6d90e4a-7817-4390-b944-091fac616a7c * Spotify: https://open.spotify.com/show/2au3zmrNf0hb3BNgZid8aX * iHeart Radio: https://www.iheart.com/podcast/269-sidebar-with-a-cfpr-pierce-298226554Connect and learn more from your host, Matt Smith and Concert Financial Planning: * Connect with Matt on LinkedIn: https://www.linkedin.com/in/matthewcharlessmith * Follow Concert Financial Planning on LinkedIn: https://www.linkedin.com/company/concertfinplan * Follow Concert Financial Planning on Facebook: https://www.facebook.com/ConcertFinPlan * Follow Concert Financial Planning on Instagram: https://www.instagram.com/concertfinplan
    Show More Show Less
    42 mins
  • The Financial Realities of Becoming an Equity Partner

    The Financial Realities of Becoming an Equity Partner
    Feb 11 2026

    Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money with Matt Smith, Episode 5

    In this episode of the Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money, Matt Smith speaks about the challenges and changes associated with transitioning from associate to equity partner with an aim to prepare attorneys for the financial realities that come with that career transition.

    Tune in to hear about:

    * Equity buy-in

    * Changes in compensation structure

    * Mandatory retirement savings

    * Increased benefit costs

    * Complex taxation requirements

    * Enhanced lending opportunities

    * The importance of advance planning

    * Understanding financial responsibilities

    * The necessity of working with specialized tax advisors

    ***********************************

    About “Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money”:

    You bill in 6-minute increments. Let’s get you some of that time back. “Sidebar with a CFP®” is your space for candid conversations about life inside BigLaw—the real stuff they don’t teach in law school or show in recruiter brochures.

    Hosted by Matt Smith, CFP® and founder of Concert Financial Planning, this show pulls back the curtain on what it actually feels like to climb the ranks, navigate transitions, and make big decisions in a high-stakes career.

    You’ll hear from Partners, Associates, and experts across law and finance—each sharing stories, surprises, and strategies for building a life (and career) that works for you.

    This isn’t a money podcast. It’s a life-in-BigLaw podcast—with a CFP® in the host chair.

    Watch or listen to more episodes of Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money:

    * YouTube: https://www.youtube.com/@concertfinplan

    * Apple: https://podcasts.apple.com/us/podcast/sidebar-with-a-cfp-pierce-the-veil-on-biglaw/id1847658694

    * Amazon: https://music.amazon.com/podcasts/f6d90e4a-7817-4390-b944-091fac616a7c

    * Spotify: https://open.spotify.com/show/2au3zmrNf0hb3BNgZid8aX

    * iHeart Radio: https://www.iheart.com/podcast/269-sidebar-with-a-cfpr-pierce-298226554

    Connect and learn more from your host, Matt Smith and Concert Financial Planning:

    * Connect with Matt on LinkedIn: https://www.linkedin.com/in/matthewcharlessmith

    * Follow Concert Financial Planning on LinkedIn: https://www.linkedin.com/company/concertfinplan

    * Follow Concert Financial Planning on Facebook: https://www.facebook.com/ConcertFinPlan

    * Follow Concert Financial Planning on Instagram: https://www.instagram.com/concertfinplan
    Show More Show Less
    44 mins
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