AI on Both Sides of the Table

Don Butler | News | Aug 26, 2025

How founders use AI to pitch and update—and how investors are using the same tools to judge them

On the pitch call, nobody knows it’s your AI doing the talking.

Alastair Goldfisher

Aug 26, 2025

What’s Inside

  • AI is reshaping the founder–VC dynamic
  • Why some investors see a red flag if founders aren’t using AI
  • Where trust, tone and human judgment still matter most

On the pitch call, nobody knows it’s your AI doing the talking.

AI has become more than a tool for Silicon Valley. It’s now a gatekeeper shaping interactions between founders and VCs.

Marina Davidova, co-founder and managing partner at Davidovs Venture Collective (DVC), says her team has replaced much of the traditional analyst layer with AI agents. Instead of junior staff spending a day pulling data and drafting a memo, an agent can do it in minutes, and at a fraction of the cost.

The firm has backed more than 120 early-stage AI startups, and Davidova says those same systems parse founder updates across the portfolio and flag which investors or operators could help with hiring, sales or partnerships.

The approach even extends to Series A strategy: DVC’s algorithms monitor seed companies, predict when they’re about to raise and let the firm offer a cap table slot before the round becomes oversubscribed.

“AI isn’t just a tool for us, it’s the backbone of our operations,” Davidova told me.

Venture firms using AI like this is nothing new. AI-powered processes for sector analysis and conducting due diligence run throughout venture firms, and increasingly on the founder side, too.

It’s well documented that entrepreneurs are using AI to stay lean, keep their costs down and then communicate their updates to investors. Some task their agents to handle first-contact emails, portfolio updates or polish their pitch decks. Others rely on them to prepare data rooms and market comps that previously took weeks.

Are VCs okay with this shift? It depends on who you ask.

AI Is Now Table Stakes for Founders

For Navin Chaddha at Mayfield, his answer is not just yes. He expects it. In his view, if a founder isn’t using AI, then that’s a warning sign.

“It’s a red flag if they’re not taking advantage of these tools,” he said.

Founders don’t get extra credit for using AI, but increasingly, not using these tools at all can raise questions.

What Chaddha is watching for is whether founders show judgment. He’s fine with AI-polished decks or agent-drafted updates, but the entrepreneur working with an investor still has to edit, contextualize and own the output. Sending untouched AI prose undermines confidence, Chaddha said.

Chaddha has also embraced AI as a workflow accelerant. His team runs AI comparisons of updated decks, uses agents to summarize key points, and surfaces signals about which founders are most active in open source or who’s vesting out of big tech.

But he draws a line. A board-level investor, in his words, still has to read the material. AI can speed the prep work, but it can’t substitute for conviction.

For him, the question isn’t whether AI belongs in founder–VC communications, it’s how skillfully founders use it as part of their process.

How VCs Use AI Inside Their Firms

Don Butler at Thomvest has been on a similar path, but with a twist: he’s learning what AI means for the venture firm itself.

His team uses Gemini inside Google Sheets to condense notes from founder meetings into highlight reels. He called it useful, but said it required iteration.

“When we asked Gemini to summarize the way a reporter would, every company suddenly looked tremendous, even if they were behind plan,” he said.

Tone, it turns out, is tricky to nail down.

With more firms like DVC and Thomvest using AI tools to analyze company data, what happens to the role of the analyst?

Butler sees a parallel between analysts in venture today and coders a decade ago. Both roles, he suggests, are being augmented by AI at first, then potentially replaced.

“We could soon see vibe coding for spreadsheets,” he said.

It’s not just founders who are under pressure to use agents smartly. Firms are, too, a shift that may reshape who works in them and how they scale.

Will AI Kill the Startup Pitch Deck?

And if AI can generate polished decks with a click, does the pitch deck still matter? Patrick Mebus, co-founder of techtrust.ai, an investor platform that uses AI to streamline diligence and portfolio support, believes the pitch deck itself is on the way out.

“Once AI makes it trivial to generate 20 polished slides, the real interaction will happen elsewhere,” he told me.

Declaring the death of pitch decks is provocative, but it points to a deeper change. Format and medium are no longer fixed. Founders can send a memo, a deck, a Loom video or task an agent to create the first draft of all three. The information matters less than the process.

Where Chaddha sees AI as table stakes and Butler frames it as analyst augmentation, Mebus sees structures dissolving. To Mebus, AI’s rise may render the classic pitch deck as outdated as a faxed executive summary.

How Founders Use AI to Run Lean and Talk to VCs

For founders themselves, AI is less about revolution and more about survival.

Lucas Dickey, co-founder of Deepcast, a startup building a platform for podcast discoverability and engagement, told me that running lean isn’t optional at the early stage, it’s a must.

AI and automation are part of that reality. They’re tools to move faster and stretch scarce bandwidth.

But when it comes to working with VCs, the tools don’t change the fundamentals.

“What matters is clarity and alignment,” Dickey said. A polished deck is fine, but if the story doesn’t match the way the company is actually building, investors will pick up on it.

For Dickey, AI-aided communications don’t replace the hard work of building trust. No matter how polished the materials, misalignment between a company’s narrative and its substance is quickly exposed.

“Tech can help you ship faster or polish materials, but what matters is that investors know where you’re headed and why,” Dickey told me in a recent podcast conversation that will be published shortly.

His view sharpens the debate. Founders may lean on agents, but inauthentic updates backfire.

Some Investors Are Skeptical of AI-Written Updates

That sentiment resonates with Hunter Walk at Homebrew. He’s seeing more AI-polished updates, but too many seem generic.

“They’re easy to ignore,” he responded to me in an email.

That doesn’t mean he dismisses AI outright. He admits decks now come with MBA-grade industry charts, and investor updates are cleaner thanks to summarization tools. But he insists the “last mile” still belongs to the founder and without judgment polish won’t help.

He’s also recalibrating what he expects from technical founders. With AI accelerating product development, he assumes founders can ship a minimum viable product faster than ever.

“If you’re waiting for a fundraise to start vibe-coding your MVP, that’s a warning sign,” he said. The hard problems — of distribution and hiring — remain squarely in human hands.

AI Pitches Are Flooding VCs

Charles Hudson at Precursor Ventures has noticed the flood, too. The rise of AI outreach hasn’t necessarily improved quality.

“It’s more voluminous,” he said, even if it’s not much better than the cold emails that came before.

What worries him is sameness. There are 10 teams chasing the same problem with the same models and the same AI-generated pitch. “Sometimes the only difference is the names of the founders,” Hudson told me.

He also recognizes the pressure running top-down, as venture-backed CEOs are having to answer to their board demands to know “all the things that they’re doing with AI to save the company money.”

For Hudson, it isn’t whether founders use AI, but how much of their story is built on it, and whether any differentiation remains.

Trust Still Seals the Deal

Taken together, these perspectives sketch the outlines of a new dynamic that is continuing to evolve.

Whereas some investors see the use of AI by founders as table stakes, Mebus believes it will ultimately dissolve the pitch deck. Meanwhile, more venture firms are incorporating AI inside their own operations, and as Butler said, that could reduce the role of analysts and associates, who are typically the first contact for startup founders.

I’ve heard from investors, similar to Walk and Hudson, who are receiving a lot of generic AI-generated spam in their inboxes.

And speaking on behalf of founders, Dickey reminds us that trust is still the coin of the realm.

As Davidova put it, AI isn’t just a thought experiment. She’s convinced founders will keep leaning on agents to cut costs and move faster. But she also knows that no matter how many memos an AI tool can draft, conviction and trust still come from people.

“AI isn’t a side tool anymore. It’s the operating system for how venture gets done,” she said.

In other words, founders can have their AI do the talking.

But what investors really want to hear is the founder’s own voice.

Follow us on LinkedIn for updates, invites to events, and original research