Episode Summary

In this episode of Million Dollar Flip Flops, Rodric sits down with Van Carlson for a deep and eye-opening conversation about risk management, business resilience, and a little-known strategy that could change how entrepreneurs protect their companies.

Van shares his journey into the world of risk management and explains how most business owners are unknowingly exposed to risks that traditional insurance simply doesn’t cover. From third-party business interruption to cyber threats and supply chain disruptions, the conversation highlights how fragile modern businesses can be — especially in an increasingly digital world.

They dive into the 831(b) tax code, a powerful and often overlooked tool that allows business owners to set aside pre-tax dollars to self-insure against risks, build a financial “war chest,” and create long-term flexibility. Van breaks down how the strategy works, who it’s for, and why it’s becoming more relevant as insurance becomes more expensive and less reliable.

This episode is a must-listen for business owners who want to stay in control, protect what they’ve built, and think more strategically about risk in an unpredictable world.

In This Episode, You’ll Learn

What risk management actually means for modern business owners
Why traditional insurance is covering less while costing more
How the 831(b) tax code allows businesses to self-insure with pre-tax dollars
The concept of building a “war chest” for unexpected disruptions
Why third-party business interruption (like cloud or CRM outages) is a growing threat
How business owners can use surplus funds for investments, loans, or future growth
The difference between risk-first strategies vs. tax-first strategies
Why small and mid-sized businesses often carry more risk than large corporations

Highlights & Timestamps

[00:00] The hidden risk of third-party business interruption

Van opens with a powerful example of businesses being locked out of their CRM systems — and having zero coverage for it.

[01:00] Who is Van Carlson?

Van introduces his background in risk management and his work helping business owners across the country.

[02:00] What is risk management, really?

A breakdown of identifying, mitigating, and planning for risks beyond traditional insurance.

[03:00] The 831(b) strategy explained simply

Van explains how business owners can set aside pre-tax dollars to self-insure and build financial reserves.

[04:00] Lessons from 2008 and financial risk exposure

How the Great Recession exposed how vulnerable business owners really are.

[05:00] Why traditional insurance is getting worse

Rising costs, shrinking coverage, and increasing deductibles are shifting more risk onto business owners.

[06:00] How the “war chest” works

Building tax-deferred reserves that can be used for claims, investments, or future flexibility.

[07:00] Investment options and liquidity considerations

How funds can be managed, invested, and accessed when needed.

[08:00] Who this strategy is actually for

Why this works best for established businesses with meaningful revenue and risk exposure.

[09:00] Using funds for growth and leverage

How business owners use surplus funds to invest, acquire assets, or support operations.

[10:00] The reality of self-insuring vs. traditional coverage

Why more businesses are choosing to take on risk themselves.

[11:00] Why risk management is often ignored

Entrepreneurs tend to focus on growth — not protection — until it’s too late.

[12:00] The rise of cyber and digital dependency risks

Cloud systems, CRMs, and tech failures are becoming major blind spots.

[13:00] Why this strategy is gaining momentum now

Insurance market shifts are driving more awareness and adoption.

[14:00] Where to learn more about 831(b)

Van shares how listeners can explore the strategy further.

Notable Quotes

“There’s literally no coverage for third-party business interruption — and it’s a serious issue.” – Van Carlson

“We’re going to be paying more and getting less from insurance for the foreseeable future.” – Van Carlson

“If we can just take a little bit off the top during the good years, we can survive the bad ones.” – Van Carlson

“Risk first, tax strategy second — not the other way around.” – Van Carlson

“At the end of the day, we’re just helping business owners protect what they’ve built.” – Van Carlson

Connect with Van Carlson

🌐 Website: https://831b.com

📧 Email: van@831b.com

LinkedIn (Van Carlson): https://www.linkedin.com/in/vancarlson/
LinkedIn (Company): https://www.linkedin.com/company/sra-831b/

Connect with Rodric

🎙 Million Dollar Flip Flops Podcast

📖 Million Dollar Flip Flops

🌍 Send a Student Leader Abroad (SASLA)

If this episode opened your eyes to hidden risks in your business, share it with another entrepreneur who needs to hear it.

Resources:

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