What a gaming industry veteran wants founders to know before they pitch

Benjie Cherniak spent more than a decade as Managing Director of Don Best Sports, growing the company from a data terminal business into what he describes as the first in-play trading floor for North American sports—selling proprietary live betting lines to operators across Europe, Asia, and the Americas before US regulation turned their data into a must-have product. Scientific Games acquired Don Best in 2018; Cherniak stayed on through the transition before leaving in 2020.

Since then, he's been writing angel checks and advising, including for companies such as OddsJam, which sold to Gambling.com for up to $160M, and ZeroFlucs, an Australian trading technology company acquired by Caesars in 2024.

In a recent AMA session hosted by the Defy the Odds community, Cherniak spent an hour fielding questions from early-stage founders across the real-money gaming space. Here’s a few key themes that came up during the talk:

On what makes operators care about new products: Cherniak's short answer is proof of concept. Operators aren't going to commit resources to something unproven—they're weighing every inbound product pitch against a list of 100 other priorities, and your product is sitting somewhere on that list. The catch-22 he described is familiar to most B2B founders: you need traction to get operator attention, but you need operator distribution to get traction. His framing on integration complexity is worth noting too; the harder a product is to integrate, the more committed an operator has to be before they'll even start. "The greater the complexity, the more committed an operator will need to be to really wanting to see whatever that new product is through," he said.

On what makes him stop reading a deck: Two red flags that come up repeatedly are overpriced rounds and founders who don't know their own numbers. On valuation, Cherniak's view is that locking in a specific number too early, especially in a frothy market, can kill a deal before it starts. "As soon as you come out and pigeonhole with a specific valuation… that can become a red flag," he said. His preference is for founders to come in with the capital ask and the ideal partnership profile, and leave room for the investor to shape the structure. The second flag is simpler: if a founder can't answer basic questions about their own business such as revenue, projections, unit economics, that’s a problem.

On AI pitches specifically: His advice to anyone pitching an AI-powered product in gaming: go narrow before you go wide. He pointed to one company in his current portfolio, InsightPlay.ai, as an example of a team that initially approached him with a broad AI-for-everything-in-gaming thesis, got passed on, came back eight months later with a focused thesis and early traction in a specific area, and got his attention the second time. "Start narrow and get good at something," he said. "Show specifically what problem you're solving that operators need solved today."

On reaching investors cold: Cherniak made sure to clarify that while he will “write some angel checks,” he’s not a VC. Instead, he invokes Lloyd Danzig, managing partner of Sharp Alpha Advisors, as an example. He says Danzig won't take cold outreach at all, on the theory that if you can't find a warm intro to an investor, you probably can't solve the harder problems that come with building a company. Cherniak says he doesn't fully subscribe to that view, but sees truth in it. His own take is that warm introductions go further, and if you have to go cold, make it personal—reference something specific the investor said publicly so it's clear you've done homework. On channel, LinkedIn beats unsolicited email.

On conferences: Cherniak's main advice as an exhibitor is not to wait for walk-by traffic. Book meetings in advance, seek out the targets you already know you want, and get off your phone when you're at the stand. The Startup Zone draws investors and operator R&D teams on purpose—that foot traffic is qualified, so engage it. The broader point is that conferences compound. "Each instance and each touch point is a building block," he said. In a slow B2B sales cycle, showing up repeatedly is how you become someone people trust.