Don't Just Ask for Feedback: A Conversation with Kris Palucki

Kris Palucki once sat down with his future co-founders, months after ChatGPT launched, and talked himself out of building what became Lovable. That story tells you almost everything about the lesson he wants founders to hear.

Kris has done the full loop most people in tech only dream about. He started as an analyst and rose to investment director at OTB Ventures, one of the region's leading VCs. Then he left to become an operator, spending three years as a product manager at Contractbook, a Google Ventures-backed contract-management platform. Then he co-founded Owlright, an AI agent that learns SaaS products and writes their documentation. And now he's back at OTB as an investment director, having seen the whole thing from every seat: investor, operator, founder, investor again.

The idea he dropped that became Lovable

Half a year before founding Owlright, Kris and the same team sat down just after ChatGPT's release and considered building something bigger than the Wix and Webflow frontend code generators: a tool that generates whole full-stack products. They didn't have an engineer in the room, so they went and asked engineers what they thought, and every single one said LLMs would never have enough context to generate full products. So they dropped it. Fast forward a few months, and that was exactly what Lovable did.

The lesson he wants every founder to carry: don't just ask for feedback, test things out. Asking around and backing down when people are skeptical is a giant warning sign, because the people you ask often can't see the future. It's the Notion story, people couldn't see the point when Google Docs existed. And it means finding co-founders committed to making it work, who look for ways through rather than reasons it'll fail or fears that "OpenAI will build it soon." Even if a giant does, how will you compete? Competition breeds the ingenuity that finds your edge.

The real scaling problem is misaligned agendas

Coming from VC, Kris thought he understood the problems of scaling: more people, harder to communicate the vision, harder to keep coherence. What actually hit him as an operator was different. The biggest problem when scaling is that you have more and more people with their own personal agendas. Everyone's in the same boat rowing in the same direction, but everyone also has a career, and they're doing what's best for the company and what's best for themselves at once. Aligning those interests while growing fast is brutally hard.

That's what finally made "company culture," a buzzword to him as a VC, mean something: building an organization where people are genuinely incentivized for the whole company to succeed. ESOP is a great tool for it, but not everyone wants equity, and in a still-immature ecosystem where few people have gotten rich from VC-backed shares, many fear or don't understand it. His deeper point, echoing the Netflix "we're a sports team, not a family" idea, is that when people have skin in the game they stop just closing deals and start caring whether the customer is the right one that will actually retain.

Building infrastructure people don't love, but need

Contractbook is a CLM platform, legal ops and contract workflows, not a sexy consumer product. Kris's answer was to try to be loved anyway: they designed for delight, so signing a contract felt like relief and success. The principle is to be pragmatic and cater to a user's needs exactly when they need them, to know your user so well you suggest a feature three seconds before they realize they need it. That's the "holy crap, they know me" moment that makes people fall in love with infrastructure.

Idea versus execution, and the model that killed his company

It's mostly about execution, but Kris learned something the hard way at Owlright: not all ideas go with all business models. He wanted to build a product-led-growth company badly, and was sure he could combine that with his idea. He was wrong. The market dynamics meant the product had to be sold sales-led, and that mismatch is a big part of why he decided to shut it down. His view on PLG versus sales-led: you can decide by design and commit early, or build and see what works. He prefers PLG, but there's nothing wrong with sales-led, it's just a different motion leaning on salespeople, warm intros, and partnerships. Long-term, a big company should be both; start where your skillset gives you an edge.

The craft of the growth PM

Moving from PM to growth PM is about numbers going up, but there's real craft to it. First you decide which metric you're growing, acquisition, onboarding, retention, or monetization, then you define the activation moment and design the product to push users toward it. His favorite example: a product might monetize best with three users but get acquired best through one person for a single use case (in Contractbook's case, just signature). So you engineer the product to motivate that one person to invite others. He looks for growth PMs who are strong with data, ideally with growth experience, and notes that marketers often become great ones because acquisition is exactly where the handoff between growth marketing and growth PM happens.

When to take VC money, and when not to

If you can build a profitable business from day one, bootstrap it, like ElevenLabs, who only took money for marketing. Plenty of businesses genuinely need venture capital to start, but don't rush it. Kris had inbound VC offers as a founder and turned them all down, because he didn't yet know what he'd do with the money beyond paying himself for a year, and it would have saddled him with the responsibility of answering to investors. His rule: verify your most important assumptions first, can you build the product, find a niche where you're the best, and sell it the way you intend. Just because you can take money doesn't mean you should, and the first round is usually raised on your own contacts, which means it's your friends' money and a huge responsibility.

Coming back to VC a completely different investor

Returning to OTB after operating and founding changed absolutely everything about how Kris evaluates investments. He understands founders, their problems, and their pressure. He can assess teams better and help them more, because he's seen many org structures, some that align everyone and some that explode into internal politics, and he can read that from an org chart. He understands go-to-market fit between sales-led and product-led models. As for pitch decks, he barely looks at them now: a wall of Silicon Valley catchphrases is a soft red flag (though after two years of everything being "AI," you can't treat it as fully disqualifying), and he'd rather spend 30 minutes on a call assessing whether a founder can survive, whether they'll pick themselves up the tenth time they fall.

Key takeaways

Don't just ask for feedback, test. Backing down because skeptics can't see the future is how you talk yourself out of the next Lovable.

The scaling problem is misaligned agendas. Everyone rows the same direction while pursuing their own career. Aligning those interests, often via real skin in the game, is the hard part.

Match the idea to the business model. Kris wanted PLG so badly he ignored that his idea had to be sold sales-led. That mismatch helped sink the company.

Don't rush VC money. If you can bootstrap profitably, do. Otherwise verify your key assumptions first, because you can't un-take the responsibility.

Operating makes you a better investor. Having founded and shipped, he reads teams, org structures, and GTM fit in ways he never could from the VC seat alone.

Frameworks worth stealing

Verify assumptions before you raise

Before taking money, list your most critical unknowns, can you build the product, is there a niche where you'd be the best, can you sell it the way you intend, and go verify those first. Inbound term sheets are tempting, but money you don't yet know how to deploy just buys you a year of salary and a lifetime of answering to investors.

Feedback from doers, not naysayers

When you're pre-product-market-fit and have no users, be very deliberate about where feedback comes from. Seek it from people who could actually help, doers and problem-solvers, not the crowd that will hand you a million reasons you'll fail. Then test rather than take the skepticism as a verdict.

Quotes worth keeping

The lines I wrote down.

Every engineer told us LLMs would never generate full products. We dropped it. Fast forward a few months: that was Lovable.

The biggest problem when scaling isn't communication. It's that everyone has their own personal agenda.

Just because you can take the money doesn't mean you should.

Rapid fire round

Same questions every guest. Quick questions, quick answers.

Best advice you've ever received? Do it. Don't overthink it.

Advice you ignored and wish you'd listened to? Someone once told him to take a deep look at a specific startup, and he dismissed it as not very interesting. It turned out to be very interesting.

What would you tell your younger self? Always be on the lookout for opportunities, don't be lazy, and always look under the rock.

Ongoing challenge that keeps you up at night? Market dynamics: 2% of companies gather 98% of the money, and the best companies choose their investors rather than the other way around. Getting into those deals is the challenge.

Favorite spot? Lasagna. He lived in Rome and had it once a week.

Tool you can't live without? ChatGPT, mostly because it takes the boring, tedious tasks he doesn't like off his plate.

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Kris Palucki is an investment director at OTB Ventures. He previously spent three years as a product manager at Contractbook, a Google Ventures-backed CLM platform, and co-founded Owlright, an AI agent that writes documentation for SaaS products. Find him on LinkedIn.