Episode 280

Exit Strategy or Identity Crisis? Why Most Founders Sell to the Wrong Buyer (and How to Fix It)

Selling your business isn’t just a financial transaction; it’s a marathon that many founders start without training. In a recent episode of the Flippa podcast, Alex Seydel, a former M&A attorney turned business exit strategist at Ripple’s Edge Advisors, sat down with Steve McGarry to pull back the curtain on the “dissatisfaction gap” post-close.

Whether you are two years or ten years away from an exit, Seydel’s insights provide a roadmap for building a business that is not just profitable, but transferable.

The “Two-Year” Rule: Why You Should Build Backwards

Most founders wait until they are burnt out to look for an exit. By that point, revenue trends might be stalling, and the owner is often too “in the trenches” to be attractive to a high-tier buyer.

Seydel suggests building backwards from a 2-to-5-year vision. * Define Your “Post-Exit” Life: Do you want to stay on as a consultant? Do you want to walk away entirely? Your desired lifestyle dictates which buyer pathways you should pursue today.

  • The “Europe Test”: If you went to Europe for two weeks without your phone, what would break? If the answer is “everything,” you don’t have a transferable asset; you have a high-paying job.

Maximizing Your Multiple: The Gap Between 6x and 8x

In industries like SaaS, multiples often fall within a specific range (e.g., 6x to 8x). But what moves the needle from the bottom of that range to the top? According to Seydel, it isn’t just your EBITDA—it’s what’s under the hood.

Levers for a Higher Valuation:

  1. Low Customer Concentration: If one client accounts for 40% of your revenue, you represent a massive risk to a buyer.
  2. Executive Leadership: Buyers want to see a strong “right-hand” team that can operate the firm once the founder transitions out.
  3. Clean Systems: A “shiny” business has documented processes that a buyer can step into and scale immediately.

Deal Structure: The Golden Rule of Cash at Close

One of the biggest pitfalls founders face is the allure of the “10x future.” Buyers often pitch complex structures involving earn-outs and rollover equity, promising that the business will explode in value post-acquisition.

Seydel’s advice is blunt: Maximize cash at close.

“You do not know what’s going to happen with the earn-out… maximize cash at close. Seeing it go poorly so many times, that is my advice to sellers almost always.”

While earn-outs can be useful for bridging valuation gaps—especially when based on new revenue streams—they shouldn’t be the foundation of your financial security.

The Gender Gap at the Deal Table

As a female founder and advisor, Seydel notes that the M&A world is still heavily male-dominated. She highlights the “napkin test” vs. “strategic readiness”—the idea that male founders often pitch on a whim while female founders wait until they are 90% “ready.”

Her message to women in the space? Trust your gut. If the buyer feels off during the Letter of Intent (LOI) phase, or if the 20-person legal call feels misaligned with your values, don’t let “sunk cost fallacy” push you into a deal you’ll regret.

Key Takeaways for Flippa Sellers

  • Don’t wait for burnout: Sell when your numbers are strong and you still have the energy to navigate the grueling M&A process.
  • Know your incentives: Understand what your broker, banker, and attorney are incentivized by before you get deep into negotiations.
  • Focus on Transferability: The more the business can run without you, the higher the multiple you can demand.

About Alex Seydel

Alex Seydel is an M&A attorney turned business exit strategist and the co-founder of Ripple’s Edge Advisors, where she helps founders grow with the exit in mind by maximizing value, attractiveness, and readiness long before a deal is on the table. Drawing on years of experience working across complex transactions, Alex partners with business owners to reduce risk, increase transferability, and position their companies for higher-quality exits at stronger multiples. A former Division I soccer player at the University of Iowa, she brings a competitive, disciplined mindset to every engagement—and when she’s not talking exits, you can usually find her discussing sports, Lane 8, or hanging out with her Golden Retriever, Thumper.


LinkedIn – https://www.linkedin.com/in/alexandria-seydel/

Website – https://www.ripplesedgeadvisors.com/

YOUR HOST

Steve McGarry

An entrepreneur, content creator, and investor based in sunny Tampa, Florida. In 2015, while living in San Francisco, Steve sold his first fintech startup LendLayer to Max Levchin’s (founder of PayPal) consumer finance company Affirm.

You May Also Like