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Why Bad Bunny's dating "playbook" is bad for fundraising - and other actionable insights to help you crush the rollup game

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Mar 5, 2026

Why Bad Bunny's dating "playbook" is bad for fundraising - and other actionable insights to help you crush the rollup game

Wisdom of 20+ investors in serial acquirers vs. dating tips from a Latin trap superstar

Alex Prokofjev
Alex Prokofjev
The Rollup of Tomorrow Vol. 13: Don’t worry about Constellation Software, it’ll be fine! A portfolio manager talks growth, customer focus & AI

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Feb 27, 2026

The Rollup of Tomorrow Vol. 13: Don’t worry about Constellation Software, it’ll be fine! A portfolio manager talks growth, customer focus & AI

Kanchan Java rapidly rose through the ranks after more than doubling revenue and profits at Charter, a 48-year old dealership VMS. Curious how she did it? PLUS: NYC Conference on March 31!

Pavel Prokofiev
Pavel Prokofiev
Are “HoldCos of HoldCos” Houses of Cards - or really clever capital allocators?

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Feb 20, 2026

Are “HoldCos of HoldCos” Houses of Cards - or really clever capital allocators?

Creative new ways to stretch the M&A dollar and to align buyer/seller incentives - by Constellation Software, Chapters Group and Röko

Alex Prokofjev
Alex Prokofjev
Eventbrite, Vimeo, Brightcove... Who’s next - and can you build a merger arb business out of Bending Spoons’ U.S. take-private rampage?

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Feb 12, 2026

Eventbrite, Vimeo, Brightcove... Who’s next - and can you build a merger arb business out of Bending Spoons’ U.S. take-private rampage?

Software investors are freaking out. Bending Spoons is cashed up. We’ve no idea what’s on their shopping list - so we asked AI!

Alex Prokofjev
Alex Prokofjev
The Rollup of Tomorrow Vol 12. 98% rejection rate & positively paranoid: meet Opera, a tenacious backer of Europe’s Independent Sponsors

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Feb 5, 2026

The Rollup of Tomorrow Vol 12. 98% rejection rate & positively paranoid: meet Opera, a tenacious backer of Europe’s Independent Sponsors

"We never discuss why a company is great because we see a lot of great companies. What we really focus on are the risks and what could kill a deal"

Alex Prokofjev
Alex Prokofjev
“AI-enabled rollups” are booming. How to pick the winners?

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Feb 2, 2026

“AI-enabled rollups” are booming. How to pick the winners?

The 3 types of rollups, and the skillsets required to run each one

Alex Prokofjev
Patrick Ryan
Alex Prokofjev, +1
Rollups from Hell Vol.4. Embracer: keeping game face on after 160+ acquisitions, a three-way split, and a 90%+ share price drop

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Jan 31, 2026

Rollups from Hell Vol.4. Embracer: keeping game face on after 160+ acquisitions, a three-way split, and a 90%+ share price drop

Lars Wingefors’ journey: flogging second-hand comics -> rollup billionaire -> a gaming industry’s bête noire

Alex Prokofjev
Dima Kovalchak
Alex Prokofjev, +1
The Rollup of Tomorrow Vol 11. Aspira Partners: The journey from an employee to a Fund GP - in 5 years & with an Independent Sponsor adventure in between

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Jan 22, 2026

The Rollup of Tomorrow Vol 11. Aspira Partners: The journey from an employee to a Fund GP - in 5 years & with an Independent Sponsor adventure in between

Who said the Nordics are too competitive? "If it's not a 4x MOIC, it's not a case for Aspira" - Andreas Bruzelius, Aspira CEO

Alex Prokofjev
Alex Prokofjev
Strange bedfellows or a match made in heaven? VC & “Trad PE” money is pouring into HoldCos: why and on what terms?

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Jan 15, 2026

Strange bedfellows or a match made in heaven? VC & “Trad PE” money is pouring into HoldCos: why and on what terms?

INSIDE: Deep-dives on Venmark and Raptor - new kids on the block backed by atypical investors. PLUS: How General Catalyst prices AI rollups.

Alex Prokofjev
Alex Prokofjev
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