It's becoming wild again in venture capital: A tiny AI startup wants investors to pay $100 to book a meeting with its founder.

  • Dan Siroker, a founder of the startup Rewind AI, is telling investors to pay if they want to meet.

  • He's charging $100 for bookings to conserve his most precious resource: time.

  • It's a sign that the AI startup market is getting frothy.

The venture-capital industry has mostly been a tale of woe in the past year, with thousands of startups struggling to raise money and many shutting down.

For some lucky founders, though, the market is as frothy as ever.

A couple of days ago, Dan Siroker, a cofounder and the CEO of Rewind AI, set his sights on meeting new investors. He anticipated so many VCs clamoring to meet that the entrepreneur decided to whittle down the field and make some money for charity while doing it.

"We can't meet with everyone so to make sure you are serious and it's a good use of our time, we are requiring a $100 payment to meet. First come, first served," he posted to X on Friday.

Over a thousand investors

Not all founders can do this. Based on how his previous fundraise went, Siroker was already bracing for a deluge of Zoom calls.

Last spring, the founder shared a link to the pitch for his startup and a form so anyone could make an offer to invest. After a few weeks, over a thousand investors had expressed interest.

Siroker closed the process with 170 bids to sift through. He raised $12 million for Rewind AI at a valuation of $350 million.

Siroker told Business Insider this week that he isn't actively fundraising. He said Rewind AI has enough cash in the bank from that last round to grow and operate for another four years.

Instead, he's meeting with investors to build relationships over time.

"This company is my life's work," he said in a direct message. "That means I'll be working with these investors for at least a decade or more. I want to make sure it's the right long-term fit, and so getting to know them over more than just one or two meetings is important to me."

Rewind's digital assistant records everything a person does on their computer, makes it searchable, and stores the recordings locally on users' computers to mitigate privacy concerns. The service has a free tier and a $19 monthly subscription that unlocks more robust features.

Rewind AI came out of stealth in late 2022 with millions from Andreessen Horowitz, First Round Capital, and others. Siroker said his startup now has 22 employees.

The hottest companies are getting funded while the rest fight for scraps

VCs falling over themselves to meet startup founders — and paying for the privilege — is a sign that at least some parts of the startup-funding environment are back to boom times.

But charging investors may be at odds with building healthy, long-lasting partnerships with them.

Siroker said that while he's asking for cash as "an efficient way to know who was serious and who wasn't," the experiment has a domino effect of weeding out self-important investors.

"I also want investors who don't have such a big ego and believe in our company so much that they'd be willing to swallow a bit of their ego and would be happy to pay to meet," he said. "Most investors think entrepreneurs should kiss their ring. This selects for the ones without ego."

This is just one example of Silicon Valley's extreme divide between haves and have-nots.

A large number of startups staved off death during the past two years by cutting costs and head counts. But as pools of cheap money these startups raised early in the pandemic run dry, many will have to go to market for capital this year.

They won't all succeed. The same scarcity of capital for startups is hurting funds. Last year, the industry notched 474 funds closed, the lowest count since the tech-bull run began in 2013, PitchBook data shows. The cash raised fell to about $70 billion from $173 billion in 2022.

A photo illustration shows the Perplexity logo on a mobile phone.
Perplexity is raising additional funding months after it closed $74 million from investors.Pavlo Gonchar/Getty Images

Investors have told BI they're seeing more binary outcomes as they spread much less capital to fewer companies.

"When deals get hot, there is extreme interest," Ben Lerer, a managing partner of Lerer Hippeau, an early-stage venture firm, told BI's Ben Bergman late last year. "But if you are on the wrong side of it, there's not a cent."

Investors are still swooning over artificial intelligence-powered software, apps, and infrastructure, part of the reason for the growing divide, Dick Costolo, the former chief executive of Twitter and now a managing partner at the newer early-stage firm 01 Advisors, said.

This week, BI reported that Perplexity, a startup that's taking on Google with a smarter search engine, is raising additional funding at a considerably higher valuation just months after closing $74 million from investors.

The funding bonanza in artificial intelligence shows no sign of slowing down. Anthropic and OpenAI closed new rounds at face-melting valuations last month. Google, Nvidia, and OpenAI employees are striking out on their own and raising gobs of cash for new startups.

"Even if you're going to be investing in early growth, you need to see them when they're just getting started and get to know the team and have them get to know you — because these things get preempted," Costolo said. "If you're not there long before the raising, you're not part of the conversation."

Siroker is counting on investors to do so. By Friday afternoon, he said he'd collected $900 from nine investors willing to pay to meet.

Though one person replying to Siroker's tweet suggested he mark the proceeds from meetings as revenue for his business, Siroker told BI he plans to donate the money to the Boys & Girls Clubs and Build, a nonprofit that teaches students how to be entrepreneurs.

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