02: Unlocking the Second Bite: Maximizing Business Exits with Todd Taskey
Todd Taskey, M&A Advisor and Angel Investor
In this episode of From Angel to Exit, host Bruce Eckfeldt sits down with Todd Taskey, an experienced M&A advisor and angel investor, to break down the strategic considerations founders must weigh when selling their businesses. Taskey shares his journey from financial advisor to M&A expert, detailing how he helps entrepreneurs structure deals that balance immediate liquidity with long-term upside.
A central theme of the conversation is the "second bite of the apple"—a strategy where sellers retain equity in their business post-acquisition, allowing them to participate in future growth and potentially reap greater financial rewards. Taskey illustrates this with real-world examples, including Digital Impulse’s strategic partnership and Social SEO’s private equity-backed expansion. He explains how earnouts, equity rolls, and debt structuring play into maximizing a founder’s post-sale value.
The discussion also covers key pitfalls founders should avoid, such as overestimating future projections, failing to align with the right buyers, and misunderstanding how private equity firms operate. Taskey stresses the importance of partnering with financial groups that align with long-term goals and leveraging their resources to scale effectively.
This episode is essential for founders considering an exit, offering expert advice on navigating M&A, structuring favorable deals, and ensuring a sale sets the stage for continued success.
Key Takeaways:
Founders should distinguish between exiting a business and using a sale to accelerate growth.
The best deals balance cash, equity, and earnout structures to optimize long-term returns.
Private equity partnerships can provide strategic advantages, but founders must ensure transparency in equity and debt arrangements.
Overstating future projections can backfire, making it crucial to present realistic financial expectations.
Retaining equity in a larger company can be a lucrative strategy for entrepreneurs who want to stay involved post-sale.
The right buyer fit—culturally and strategically—is just as important as financial terms.
Business owners should have GAP-compliant financials and proper accounting structures in place before seeking a sale.
Understanding different private equity models helps founders negotiate better terms and avoid common pitfalls.
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