Timing Is Everything: Why Founders Who Wait Lose Millions

Timing is everything

In the latest episode of This Is M&A, Ben Boissevain, Founder and Managing Partner at Ascento Capital Invest, joins host Steven Monterroso to discuss why waiting for โ€œperfectโ€ market conditions could be the most expensive mistake a founder ever makes.

โ€œFounders love to talk multiples, but 2021 was an anomaly,โ€ says Boissevain. โ€œThose valuations are gone, and what matters now is timing and readiness.โ€

Itโ€™s a sobering truth many dealmakers have learned the hard way. The deals closing today didnโ€™t start yesterdayโ€”they were set in motion six months ago, when market signals looked very different. By the time most founders decide the timing feels โ€œright,โ€ the window has already begun to close.

Why Readiness Beats Timing

Boissevain has spent decades advising growth-stage tech companies on M&A strategy, fundraising, and exits. His message is clear: the best founders donโ€™t wait for the stars to align โ€” they prepare continuously.

โ€œThe best founders treat deal preparation like product development โ€” ongoing and strategic,โ€ Boissevain explains. โ€œKnow your top acquirers, benchmark your sector, and stay ready.โ€

That readiness mindset can mean millions in difference at exit. In competitive markets, the first movers often secure premium valuations โ€” while those who follow the crowd see their multiples cut in half.

The Clock Is Always Ticking

Deals rarely collapse because of bad fundamentals; more often, they die from delays, indecision, or lack of preparation.

As Boissevain reminds listeners, โ€œTime kills deals.โ€

For founders eyeing a liquidity event in 2026 or beyond, now is the time to tighten diligence materials, keep financials audit-ready, and understand who your likely buyers are. Because when the market turns, opportunity favors those already in motion.

๐ŸŽง Listen to the full episode of This Is M&A: โ€œTiming Is Everything: Why Founders Who Wait Lose Millions.โ€

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