Lionmaker Consulting · Notes

Notes for founders considering what's next.

Strategy, stewardship, and exit. From the side of the desk that has been a founder, not the side that has only consulted to one.

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Why Tim Cook's 'Perfect' Succession Will Sink Most Private Companies

Success magazine is calling Tim Cook's succession a masterclass. They're wrong. The Apple playbook will destroy most founder-led businesses because it confuses performance theater with actual transition strategy.

June 11, 20267 min read
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The Real Founder Trap: Why 'Irreplaceable' Owners Get Punished

The Business Transition Academy says buyers only pay for businesses that can operate without the founder. That's precisely backwards. Here's what buyers really value.

June 9, 20265 min read
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The Real Reason Founder Transitions Fail (It's Not What You Think)

Everyone blames founders for botched handovers. But the real culprit is incoming leaders who mistake stewardship for ownership from day one.

June 2, 20265 min read
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The Small SaaS Valuation Trap Everyone Missed

QuantPillar documents the SaaS multiple collapse, but the real story isn't AI disruption. It's that small founders are pricing for a market that no longer exists.

May 28, 202610 min read
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QSBS Planning Has Become a Founder Tax Trap

While tax professionals celebrate QSBS's expanded exclusion limits and new tiers, the real winner isn't founders—it's the advisory industrial complex that profits from overcomplicated planning.

May 26, 20269 min read
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The Problem Isn't Exit Prep — It's Exit Avoidance

Everyone's talking about founders being unprepared for exit. But the real issue is deeper: most founders spend years avoiding the only conversation that matters.

May 21, 20267 min read
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The Add-On Addiction: Why 73% of PE Deals Signal a Broken Market

Calder Group's Q2 data shows 59% of sub-$50M PE deals are add-ons. This isn't market efficiency—it's systematic founder dependency and broken exit readiness across middle market.

May 19, 20269 min read
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The QSBS Timing Trap: Why the New OBBBA Rules Are a Strategic Mistake

OBBBA's new 3-year QSBS holding periods look generous, but they're a founder's trap. The real cost of early exit isn't the exclusion percentage—it's the strategic damage.

May 14, 20269 min read
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The Exit Regret Myth—Why Warrillow's 74% Statistic Misses the Point

Warrillow's PREScore promises to fix exit regret through better psychological preparation. The uncomfortable truth: most disappointed sellers built lifestyle businesses, not assets.

May 7, 20268 min read
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MSP Owners Aren't Ready for What 2026 Actually Demands

The MSP valuation conversation has become a distraction from the real work. While everyone chases multiples, the market is demanding something far more fundamental—and most owners aren't ready.

May 6, 20269 min read