How to Buy Companies That Aren't Profita...

Matt Arsenault, VP of Corporate Development & Strategic Alliances at Jamf

Venture-backed companies are priced at their future state, not their current revenue. When growth stalls and another fundraising round stops making sense, the gap between VC valuation and what a strategic buyer will pay becomes the hardest conversation in any deal process. Matt Arsenault, VP of Corporate Development & Strategic Alliances at Jamf, has run this play across hundreds of targets. His work starts before the deal does, with the founder relationship, the cap table, and a clear-eyed conversation about risk tolerance that most corp dev teams never have. 

What You'll Learn

• Why a $25M offer today can beat a $125M VC exit three years out
• How AI is shrinking the moat of wrapper-product startups and changing target screening
• The seven stakeholder groups in any acquisition and why most founders miss them
• How liquidation preferences and cap table structure change the math behind any offer
• Why VC relationships matter as much as founder relationships before a deal starts
• How to structure deals for underwater targets without losing the team
• What entrepreneurs should know about VC terms before taking their first check

If you're working a deal where the founder's VC valuation is the first thing they said and the last thing they'll let go of, DealPilot, powered by M&A Science, gives you the guidance to close the gap without overpaying.

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Episode Chapters

[00:01:14] Introduction and Kison's overview

[00:03:32] Matt Arsenault's background and path into M&A

[00:05:17] How VCs actually value companies: the two major components

[00:06:52] Where VC and strategic buyer valuations diverge, and why

[00:09:29] The current market for VC-backed acquisition targets

[00:10:39] Rule of 40, profitable growth, and what AI is changing

[00:25:01] The liquidation preference math: $25M today vs. $125M later

[00:31:38] Cap table dynamics, voting power, and co-founder alignment

[00:33:10] How to have the valuation conversation with a founder

[00:35:35] How to structure deals when a company is underwater

[00:36:45] Stakeholder management: severance, retention, and employee equity

[00:44:03] Structural tools for bridging valuation gaps

[00:49:21] What entrepreneurs should know before taking their first VC check

[00:51:03] Due diligence war stories: what a code scan revealed