Why Matt Tripp Is Doubling Down on Betr After Losing the $400M PointsBet Battle

Betr Entertainment (ASX: BBT) lost the brutal battle for PointsBet in September 2025, with Japan’s MIXI securing 51.86% control through a superior cash offer. But instead of retreating, founder Matt Tripp appears to be doubling down. Reports from August 2025 indicate Tripp held meetings with Entain executives in London to discuss acquiring their Australian operations, Ladbrokes and Neds, in what could be a transformative deal for the $315 million company. For investors, this raises an intriguing question: is backing Tripp at current prices around $0.27 one of the best asymmetric bets on the ASX?

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The Jockey Worth Backing: Tripp’s Proven $338M Track Record

When evaluating early-stage wagering companies, backing the operator often matters more than the current financials. Matt Tripp’s track record speaks volumes:

• Sportsbet: Bought for $250,000 in 2005, sold to Paddy Power for $338 million by 2011 – a 1,350x return over six years
• BetEasy: Built from scratch, sold his final stake to The Stars Group (now Flutter) for a reported $151 million
• Betr commitment: Still holds 19.9% of PointsBet despite losing the takeover battle, signalling continued conviction

These aren’t the actions of someone who’s given up. Tripp has built and exited two major wagering businesses successfully. The pattern suggests he sees material upside ahead, and his willingness to stay invested in PointsBet even after defeat indicates strategic patience rather than desperation.

The Entain Prize: Instant Scale in a Consolidating Market

The potential Entain acquisition could transform Betr overnight. Entain’s Australian division, Ladbrokes and Neds, holds approximately 17% market share and generated £257 million ($500M AUD) in revenue during H1 2025. Acquiring these established brands would instantly elevate Betr from a 5% market share challenger to a major player with potentially 20%+ combined share.
The strategic logic is compelling. Rather than spending years grinding for market share organically, Betr could leapfrog competitors by acquiring proven operations with existing customer bases, regulatory approvals, and established technology infrastructure. The August 2025 London meetings between Tripp, Betr CEO Andrew Menz, and Entain executives suggest serious discussions are underway, though no formal offer has been announced.
Entain may be motivated to sell following AUSTRAC’s December 2024 legal action over alleged anti-money laundering failures, which could result in substantial fines exceeding $100 million.

The Investor’s Takeaway

At current prices around $0.27, Betr trades well below analyst targets of $0.44-0.47, implying 60%+ upside if Tripp executes successfully. The $315 million market cap creates significant room for rerating if an Entain deal materialises or organic growth accelerates through the PointsBet stake.
However, investors must recognise the risks. The PointsBet loss demonstrates that even Tripp’s vision doesn’t guarantee victory; MIXI’s $1.25 cash offer proved more attractive than Betr’s $1.22 scrip proposal despite lower total value. An Entain acquisition would require substantial capital, likely involving dilutive equity raises or debt that could pressure margins.

The key question: can Matt Tripp do it again? His track record of turning $250K into $338M with Sportsbet, then successfully building and exiting BetEasy, suggests yes. For growth investors comfortable with execution risk and capital dilution, backing Tripp’s third major wagering venture at current valuations could prove rewarding if his pattern of building and exiting successfully repeats. The jockey has proven he knows how to win this race.