Why 90% of Startups Screw Up Their Taxes (And How the Smart 10% Get Rich)

Aug 27

AUGUST 27, 2025 | 00:33 | Episode 84

Pablo Martell, founder & CEO Alpine Mar

Pablo Martell is a Fort Lauderdale–based CPA and the founder and CEO of Alpine Mar, a tax strategy firm that focuses on using technology and experience to deliver industry-leading results, service, and guidance to individuals and businesses of all sizes. With experience at global powerhouses like EY and Goldman Sachs, Pablo set out to redefine the accounting industry, bringing Big Four–level expertise with the personalized service of a boutique firm. Pablo is also a real estate investor and host of the Roads & Riches podcast, where he explores the future of business, entrepreneurship, and personal development. A devoted family man, Pablo enjoys spending time with his two young daughters and unwinding on the golf course.

ABOUT THIS EPISODE

Intro

The conversation with Pablo Martel illuminates the myriad complexities that startups face, particularly concerning tax strategies and financial structuring. At the outset, Martel, a CPA and fractional CFO, emphasizes the critical importance of avoiding common pitfalls that can jeopardize a startup's equity value. He elucidates the often-overlooked significance of the 83B election, a document that can profoundly influence a founder's tax obligations and potential financial success. Throughout our dialogue, we explore the various ways in which startups can secure their financial future by adopting prudent tax strategies and ensuring their legal structures are sound from inception. This episode serves as an essential guide for budding entrepreneurs, equipping them with the knowledge necessary to navigate the treacherous waters of startup finance effectively.

Conversation

The dialogue between Jothy Rosenberg and Pablo Martel elucidates the myriad of challenges that startups encounter, particularly emphasizing the often-overlooked tax implications that can prove detrimental to emerging businesses. Martel, a seasoned CPA and fractional CFO, highlights the critical nature of establishing a robust legal and tax framework from the inception of a startup. He elaborates on the importance of the 83B election, a strategic maneuver that can significantly affect equity compensation and tax liabilities for co-founders and early employees. By prioritizing these elements, startups position themselves to avoid common pitfalls that can jeopardize their financial viability and long-term success. Furthermore, Martel discusses the nuances of qualified small business stock (QSBS) and its tax benefits, urging founders to seek informed guidance to navigate these complex considerations effectively. Through this conversation, we glean invaluable insights into the foundational steps necessary for fostering sustainable growth within the competitive landscape of entrepreneurship.

Takeaways

Startups must prioritize establishing a robust legal and tax structure from the outset, as decisions made during initial stages profoundly influence future operations.
Understanding and correctly implementing 83B elections is critical for founders and early employees to optimize their tax advantages when granting equity.
R&D tax credits represent a significant opportunity for startups, allowing them to offset payroll taxes during periods of financial loss and encouraging innovation.
It is essential for founders to maintain a constant awareness of their cash burn and available runway, as these metrics are vital for the sustainability of their venture.
Engaging with qualified professionals, such as CPAs and attorneys, early in the startup journey can prevent costly mistakes and facilitate informed decision-making.
Founders should be aware of the nuances of QSBS qualification, as it can provide substantial tax benefits upon eventual sale or exit of the business.

Links

Pablo Martell:

LinkedIn https://www.linkedin.com/in/pablo-martell/

Twitter (X) https://x.com/PabloMartell_?ref_src=twsrc^google|twcamp^serp|twgr^author

Alpine Mar:

Website https://alpinemar.com/

Instagram https://www.instagram.com/alpinemarhq/?hl=en

LinkedIn https://www.linkedin.com/company/alpine-mar-cpa-advisors/about/

Twitter (X) https://x.com/alpinemarhq

Please leave us a review: https://podchaser.com/DesigningSuccessfulStartups

Tech Startup Toolkit (book): https://www.manning.com/books/tech-startup-toolkit

Jothy’s website: https://jothyrosenberg.com

Who Says I Can’t Foundation: https://whosaysicant.org

Jothy’s TEDx talk: https://www.youtube.com/watch?v=PNtOawXAx5A

Chapters

00:04 - Introducing a New Guest

00:36 - Introduction to Startup Success

11:49 - Navigating Tax Implications for Startups

15:23 - Understanding QSBS and 83B Elections in Startups

26:54 - Understanding R&D Tax Credits for Startups

28:20 - Understanding Economic Nexus in Startups

WATCH THE YOUTUBE EPISODE

WATCH THE MAGIC CLIPS (<1 min each)

Pausing for financial review

83b elections for key employees

Jothy Rosenberg