Square vs QuickBooks 2025 Showdown: Who Wins for SMBs?

Square and QuickBooks are both powerful tools for managing business finances. Check out my breakdown of their similarities and differences.

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Y Combinator-backed Rulebase wants to be the AI coworker for fintech

Y Combinator-alum Rulebase is betting that the next wave of automation in financial services will be the unglamorous tasks.

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Kayak co-founder takes on Calendly with new Supercal scheduling platform

The entrepreneur has launched Supercal, a free scheduling platform that’s designed to make booking meetings more efficient and simple.

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Trump’s willingness to let TikTok go dark motivated China to make deal, says Bessent

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Meta Connect 2025: AI-powered smart glasses take center stage

Analysts and investors will be watching how the public responds to Meta’s big bet on smart glasses during its Connect event.

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Amazon to host Prime Big Deals Day sales event on October 7 and 8

Amazon is hosting its Prime Big Deals Day sales event in October again.

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Entain details new sportsbook features to enhance customer experience

Entain has unveiled a range of new features as part of its ‘product innovation strategy’ to enhance its betting offerings across the United States, the United Kingdom, and Brazil.
The tools, aimed at improving the customer experience, include faster withdrawals, new BetBuilder technology, live same-game parlays, app improvements, and localized features for specific markets.
Entain has detailed that the developments further evidence the company’s commitment to delivering the best betting experience for players through engaging, seamless, and localized interfaces. 
The fresh launch for the parent company of BetMGM, Ladbrokes, and Coral comes just weeks after it confirmed positive half-year results, with 7% year-on-year growth, reaching £2.63 billion ($3.59b). 
Despite the uplift, Entain will need to set aside around $100 million due to pending fines from the Australian watchdog AUSTRAC.
Key enhancements to Entain’s betting products 
Beyond the headings of what the international betting operator is improving, the company has provided specifics on how customers will receive a better experience. 
It states that 90% of withdrawals are now processed within a minute, delivering a frictionless service. 
Its gaming offering continues to expand with around 150 new titles launched monthly and 20% of those available on early-access, while roughly 40 million coins have been redeemed on the rewards system.
Other key highlights include BetMGM’s partnership with Angstrom to deliver live same-game parlays for MLB and NFL, with NBA to follow in due course. This has allowed for real-time bet tracking on Apple devices for added functionality.
Entain’s proprietary soccer BetBuilder is said to have driven an 80% increase in pre-game turnover and doubled its share of turnover to 12% in markets where it’s available. Similarly, localized features in Brazil have unlocked an enhanced soccer betting experience through Fantasy Markets, AccaBoost, in-play soccer BetBuilder, and Stats Pro. 
On the Ladbrokes and Coral brands, the Quacca Bar has provided a seamless option to place various wagers, including BetBuilders, without leaving the app or changing menus. It has been popular with users.
Entain Chief Technology Officer, Satty Bhens, stated:
“Our Sportsbook product has never been stronger. We’ve closed the gap and are now pivoting from catching up to going beyond. 
“From live single-game parlays in the US to in-play BetBuilders in Europe and Brazil, we’re upgrading player experiences while modernising our trading back office. This is just the beginning of what we can achieve as we continue to lead the industry in product innovation.”
Image credit: Entain
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Sports company Better Collective launches AI-powered auto-built bet tool ‘Playbook’

The digital sports media group Better Collective has launched ‘Playbook,’ which it describes as an AI-powered betting solution that will change how fans place bets.
The launch comes after the company issued a press release in February, which shared details of a pilot-like program run in New Orleans. The pilot program has now been scaled into the full product.
“At its core, Playbook is built to make betting seamless and more engaging for fans. Playbook enhances the user experience by delivering an actionable link – utilising bet slip image recognition built on AI and smart deeplinks – from betting content and tips that opens directly into a sportsbook app or website with the bet pre-loaded,” the company explains.

In a how-to video, the Playbook replies to people on the X platform (formerly Twitter) with pre-built bet slips. It shows the official account sharing a parlay and then suggests people can reply to the post with their sportsbook of choice.
From there, Playbook is supposed to rely in seconds with an auto-built bet slip. Six sportsbooks are currently compatible with the platform.
Playbook launches ahead of NFL season, with more markets in the pipeline
The video ends with the following statement: “Manual bets are dead, auto-built slips are the future.”
Jesper Søgaard, Co-Founder and CEO of Better Collective, said: “Playbook reflects our ambition to lead in delivering unique, and engaging sports betting experiences for sports fans and bettors while driving strong retention value for our partners.
“This positions Better Collective uniquely within the global sports betting ecosystem, where sports fans wager more than 1.5 trillion EUR annually.”
The gambling-related tool has launched ahead of the NFL season, but Better Collective states that additional key markets are in the pipeline. The company also plans to build out a broader AI suite of tools and betting assistants.
Featured Image: Screenshot via The Action Network/Playbook YouTube video
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Robinhood files lawsuit against Massachusetts Gaming Commission and Attorney General

The financial-services company Robinhood has filed a lawsuit in Massachusetts against the area’s Attorney General and the Massachusetts Gaming Commission.
It was filed on Monday (September 15), with Robinhood asking a judge to award it an injunction against the state bodies to prevent them “from enforcing preempted Massachusetts law against Robinhood for its facilitation of transactions involving sports-related event contracts.”
In the filing, the company points to Kalshi a few times. This comes after the state of Massachusetts filed a lawsuit against the prediction market platform for allegedly offering unlicensed sports gambling.

BREAKING: Robinhood has filed a lawsuit in Mass. federal court against the @MassAGO and @MassGamingComm to block the two state agencies “from enforcing preempted Massachusetts law against Robinhood for its facilitation of transactions involving sports-related event contracts.” pic.twitter.com/l0m1SFekqm
— Daniel Wallach (@WALLACHLEGAL) September 15, 2025

The lawsuit was filed last Friday (September 12) and it claims that Kalshi uses an online exchange to offer sports wagering, under the guise of event contracts. The Attorney General’s Office alleges that “these ‘event contracts’ closely resemble sports wagers offered by licensed operators.”
A press release was published by the State Attorney General Andrea Joy Campbell in which she states: “Sports wagering comes with significant risk of addiction and financial loss and must be strictly regulated to mitigate public health consequences.
“This lawsuit will ensure that if Kalshi wants to be in the sports gaming business in Massachusetts, they must obtain a license and follow our laws. I am grateful for the ongoing partnership with the Gaming Commission.”
Robinhood refers to Kalshi in its Massachusetts lawsuit
Robinhood refers to the new state court lawsuit against Kalshi and states there is a “real and imminent threat that Massachusetts will file a similar complaint and motion against Robinhood” as the company intermediates its customers’ event contract trades, including sports-related event contract trades, on Kalshi’s exchange.
“While Robinhood facilitates the placement and liquidation of event contracts for its customers, the contracts themselves trade on KalshiEx LLC’s (“Kalshi”) Commodity Futures Trading Commission (“CFTC”)-designated exchange,” the filing also states.
After explaining the reasoning for going ahead with the lawsuit, the company summed it up with the following: “Robinhood therefore had no choice but to file this lawsuit to protect its customers and its business. Robinhood respectfully requests that this Court enjoin Defendants from enforcing preempted MA law against Robinhood for its facilitation of sports-related event contracts.”
Featured Image: AI-generated via Ideogram
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Matthew Prince Wants AI Companies to Pay for Their Sins

The Cloudflare CEO joined The Big Interview to talk about standing up to content scraping, the internet’s potential futures, and his company’s relationship to Trump.

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